WELCOME 11th International Symposium on the Chemistry of Natural Compounds (SCNC 2015) will be held on October 1-4 in Antalya, Turkey. This symposium series has been organized jointly by Anadolu University and Institute of Chemistry of Plant Substances (ICPS) of the Uzbekistan Academy of Sciences biennially since 1994 in Uzbekistan and Turkey. Only the 9th SCNC was held in 2011 at Urumqi, XinjiangUyghur Autonomous State in P.R. China. Since 2011, Xinjiang Technical Institute of Physics and Chemistry of the Academy of Sciences of People’s Republic of China became one of the organizers of this scientific forum and the 9th International Symposium on the Chemistry of Natural Compounds was held in 2011 at Urumqi, Xinjiang - Uygur Autonomous Region of China. SCNC deals with a number of relevant topics presented by most reputed scientists in the field. In addition, the symposium is open for your highly relevant contributions covering chemical, pharmacological, biological activity related aspects of natural products to be presented either orally or as poster. Previous SCNC symposia were organized in Turkey in Eskisehir (1996, 2009), Ankara (2005) and Isparta (2001). Antalya, with her natural beauties blended with history and culture will be the venue of the 11th SCNC which is expected to be the meeting place of scientists from all over the World dealing with all aspects of medicinal and aromatic plants and natural products. We are ready to welcome you 1-4 of October of 2015 year to get together with fellow scientists in this global event in Antalya, Turkey. Co-President Prof. Dr. K. Husnu Can Baser (Turkey) Prof. Dr. Shomansur Sh. Sagdullaev (Uzbekistan) Prof. Haji Akber Aisa (PR China)
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COMMITTEES OF SCNC 2015 Co-Presidents Prof. Dr. K. Husnu Can Baser, Turkey Prof. Dr. Shomansur Sh. Sagdullaev, Uzbekistan Prof. Haji Akber Aisa, PR China
Secretary Prof. Dr. Fatih Demirci, Turkey
Members of the Local Organizing Committee Prof. Dr. K. Husnu Can Baser, President Prof. Dr. Fatih Demirci, Secretary Prof. Dr. Neşe Kırımer, Member
Members of the Scientific Committee Acad. AS Ruz Takhir F. Aripov, Uzbekistan
Prof. Jing-Shan Shen, PR China
Prof. Dr. Nasrulla D. Abdullaev, Uzbekistan
Prof. Dr. Neşe Kırımer, Turkey
Prof. Shakhnoza S. Azimova, Uzbekistan
Prof. Dr. Temel Özek, Turkey
Prof. Khusnutdin M. Shakhidoyatov, Uzbekistan
Prof. Dr. Betül Demirci, Turkey
Prof. Vladimir N. Syrov, Uzbekistan
Prof. Dr. Müberra Koşar, Turkey
Prof. Abbaskhan S. Turaev, Uzbekistan
Assoc. Prof. Dr. Mine Kürkçüoğlu, Turkey
Prof. Yang Ye, PR China
Assoc. Prof. Dr. Gülmira Özek, Turkey
Prof. Xiao-Jiang Hao, PR China
Assoc. Prof. Dr. Ayhan Altıntaş, Turkey
Prof. Zeper Abliz, PR China
Assoc. Prof. Dr. Gökalp İşcan, Turkey
Prof. Ren-Xiang Tan, PR China
Assoc. Prof. Dr. Nilgün Öztürk,Turkey
Prof. Xin-Miao Liang, PR China
SYMPOSIUM TOPICS Symposium topics cover a wide area concerning natural products ranging from chemistry, pharmacology, biological activity and technology aspects of extracts, essential oils, isolated constituents and their synthetic derivatives. After the symposium peer-reviewed papers will be published in the official journal of ICPS, the Chemistry of Natural Compounds, an SCI-indexed Springer journal.
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SPONSORS Organizing Institutions Anadolu University (http://www.anadolu.edu.tr/)
Supporting Institutions Turkish Cooperation and Development Agency (TIKA) (http://www.tika.gov.tr) International Council for Medicinal and Aromatic Plants (ICMAP) (http://www.icmap.org/) Phytochemical Society of Europe (PSE) (http://phytochemicalsociety.org/ ) Phytochemical Society of Asia (PSA) (http://phytochemsoc-asia.com/)
Sponsors Awe Cemre (http://www.awecemre.com/) BadeBio (http://www.badebio.com/) Talya (http://www.talyabitkisel.com/) Association of All Pharmacist Cooperatives (TEKB) (http://www.tekb.org.tr/) SEM Lab (http://www.semlab.com.tr/en/)
Symposium Organizing Company Bilkon Turizm www.bilkonturizm.com.tr e-mail:
[email protected] Addr: Cinnah Cad. Gelibolu Sk. No:3/11 06680 Kavaklıdere / ANKARA Tel: 0090 312 466 1 466
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SCIENTIFIC PROGRAMME 30th September 2015, Wednesday 16.00-19.00 Registration – (Lobby) 1st October 2015, Thursday 08.00-12.30 Registration – (Symposium hall foyer) Opening Ceremony • Welcome Speech 09.30-09.45 - Prof. Dr. K. Hüsnü Can BAŞER - President, Local Organization - Prof. Dr. Shomansur Sh. Sagdullaev- President (Uzbekistan) - Prof. Haji Akber Aisa - President (PR China) 09.45-10.00 Classical Turkish Music 10.00-10.30 Session Break – Tea & Coffee Hall A Chair persons: K. Hüsnü Can Başer, Shomansur Sh. Sagdullaev, Haji Akber Session 1 Aisa PL 1: Medicinal preparations based on diterpenoid alkaloids isolated from the Central 10.30-11.00 Shomansur Sh. Sagdullaev Asian plants PL2: Study on the active compounds of ethnic medicine and rupestonic acid 11.00-11.30 Haji Akber Aisa derivatives 11.30-12.00 PL3: Essential oils of Achillea species of Turkey K. Hüsnü Can Başer 12.00-14.00 Lunch Break Session 2 Hall A: Essential oils Chair persons: Gerhard Franz, V. N. Syrov 14.00-14.15 OP 1: Essential oils of plants of Central Asia Svetlana Zhigzhigzhapova OP 2: Chemical composition of essential oils from savory under different extraction methods: Conventional distillation, an innovative technique steam Abdollah Ghasemi Pirbalouti 14.15-14.30 distillation, microwave-assisted steam hydro-diffusion, and microwaveassisted hydro-diffusion methods OP 3: Chemical composition and biological activity of essential oil of Chaerophyllum Ali Şen 14.30-14.45 aromaticum from Turkey 14.45-15.00 OP 4: Lipids and essential oils of Arischrada bucharica and Ziziphora pedicellata leaves Daniya Asilbekova 15.00-15.30 Session Break – Tea & Coffee Session 2 Hall B: Essential oils Chair persons: Neşe Kırımer, Sh. S. Azimova OP 5: Development of the technolgy of krostopidin preparation production from the 14.00-14.15 Alimdjan Sadikov aerial part of Capparis spinosa OP 6: Heavy metal contamination of soil and plants in the vicinity of blacksmith 14.15-14.30 Idris Aminu workshop in Kazaure Town, Nigeria OP 7: Perspectives of the development of local hepatoprotectors based on 14.30-14.45 Natalya Tursunova phytocomposition with phospholipids OP 8: Toxicity analysis of polychlorinated dibenzofurans using global and local 14.45-15.00 Ablikim Kerim aromaticity indices 15.00-15.30 Session Break – Tea & Coffee
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1st October 2015, Thursday Session 3 Hall A: Phytochemistry Chair persons: İhsan Çalış, N.V. Tursunova 15.30-15.45 OP 9: Monoterpene esters of aromatic acids from the roots of Ferula calcarea Serkerov Sirajeddin OP 10: New coumarin derivatives with isopropyl group at C-8 of Peucedanum 15.45-16.00 Gultekin Gasumova ruthenicum OP 11: The structure and the biological activity of Seseli campestre angular 16.00-16.15 Nigar Mikailova pyranocoumarins OP 12: New Metabolites from the Algae-derived fungi Penicillium thomii and 16.15-16.30 Olesya Zhuravleva Penicillium lividum 16.30-16.45 OP 13: Investigations natural products from medicinal plants of Kazakhstan Janar Jenis OP 14: On a facile method for enhanced throughput in isolation of lupeol from 16.45-17.00 John Anyam Maranthes polyandra 17.00-18.30 Poster Session I (Numbers 1-100) Session 3 Hall B: Phytochemistry Chair persons: Erdal Bedir, B. Zh. Elmuradov OP 15: Beneficial effects of clove on oxidative stress and pro-inflammatory cytokines 15.30-15.45 (interleukin-1, 6 and TNF-α) produced by adipose tissue in rats fed a high-cholesterol Krouf Djamil diet OP 16: Bioassay-guided isolation of sesquiterpene coumarins from Ferula narthex: A Mahboob Alam 15.45-16.00 new anticancer agent 16.00-16.15 OP 17: Pharmacology of succinate-containing aminothiols Shabanov Petr 16.15-16.30 OP 18: The cytotoxic activity guided fractionation of Arum italicum rhizomes Hale Gamze Ağalar OP 19: Anti-cancer effect of Curcuma longa rhizome extract against Daudi and Jurkat Farah Jabbar 16.30-16.45 cell lines evaluated by MTT assay and apoptosis activity 16.45-17.00 OP 20: The molecular mechanism of inhibition of cyclooxygenase by flavonoids Nasrulla Abdullaev 17.00-18.30 Poster Session I (Numbers 1-100) 19.30 Welcome reception 2nd October 2015, Friday Session 4 Hall A Chair persons: Fatih Demirci, K.A. Eshbakova PL4: Chemistry and biological tests of complex natural products from medicinal 08.30-09.00 Jianming Yue plants 09.00-09.30 PL 5: The untapped potential of the African Herbal Pharmacopoeia Ameenah GuribFakim 09.30-10.00 PL 6: Phytochemistry of liverworts: Bio-and chemical diversity and biological activity Yoshinori Asakawa 10.00-10.30 PL 7: Microbial biotransformation studies on Astragalus cycloartanes Erdal Bedir 10.30-11.00 Session Break – Tea & Coffee Session 5 Hall A Chair persons: Ameenah Gurib-Fakim, Jianming Yue 11.00-11.30 PL 8: Form natural tetrahydroprotoberberines (THPBs) to novel drug candidates Jingshan Shen PL 9: Deuterium exchange of α-methylene group protons in the tricyclic quinazolin11.30-12.00 Mikhail Levkovich 4-ones and -4-thiones 12.00-12:30 PL 10: Polyphenolic compounds from various plant species growing wild in Turkey Hasan Kırmızıbekmez 12.30-14.15 Lunch Break Session 6 Hall A: Phytochemistry Chair persons: Mahboob Alam, N. Levlovich OP 21: Biologically active coumarins and chromones of roots, flowers and leaves of Hilal Imanli 14.15-14.30 Visnaga daucoides OP 22: Novel sesquiterpene coumarin ethers from the dichloromethane extract of the 14.30-14.45 Mahmut Miski roots of Heptaptera cilicica 14.45-15.00 OP 23: The active constituents of yacon leaves De-Qiang Dou 15.00-15.15 OP 24: Purification of soybean lecithin from phosphatidic concentrate Salohiddin Aminov 15.15-15.30 OP 25: A new sesquiterpene coumarin from Ferula ovina Komila Eshbakova 15.30-16.00 Session Break – Tea & Coffee SCNC 2015 Abstracts
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2nd October 2015, Friday Session 6 Hall B: Pharmacology Chair persons: Mahmoud ElSohly, N.Z. Mamadalieva OP 26: Contribution of different molecular and physiological mechanisms in the 14.15-14.30 Firuza Tursunkhodjaeva development of analgesic effects of diterpenoid alkaloids 14.30-14.45 OP 27: Derivatives of cyloorbicoside A and their biological activity Manzura Agzamova 14.45-15.00 OP 28: Pharmacological activities of selected Algerian medicinal plants Djebbar Atmani 15.00-15.15 OP 29: Secondaty metabolites of Geranium genus plants and their biological activity Doniyor Siddikov OP 30: Botanicals risk assessment in the Mediterranean Area (BRAMA)- A 15.15-15.30 Hanem Awad toxicological study 15.30-16.00 Session Break – Tea & Coffee Session 7 Hall A: Phytochemistry Chair persons: Hasan Kırmızıbekmez, S.D. Gusakova OP 31: Sesquiterpene lactones of Artemisia species of Uzbek flora assigned to 16.00-16.15 I.D. Shamy’anov medicine 16.15-16.30 OP 32: A new ent-kaurane type diterpene diglucosidefrom Pulicaria uliginosa Komila Eshbakova 16.30-16.45 OP 33: Investigation of alkaloids of Catharanthus roseus cultivated in Uzbekistan Madina Mirzaeva 16.45-17.00 OP 34: Method for isolation of the sum of iridoids from Phlomoides species Durbek Usmanov 17.00-17.15 OP 35: Phytoecdysteroids from Phlomoides ostrowskiana species Ugiloy Yusupova 17.15-17.30 OP 36: Extraction of esters from the aerial part of Ferula tenuisecta Ravshan Khalilov Session 7 Hall B: Pharmacology Chair persons: Mahmut Miski, A.Z. Sadikov OP 37: Properties, structure and biological activity of polysaccharides from seeds of 16.00-16.15 Rano Rakhmanberdieva local species of Gleditsia and Crotalaria OP 38: Toxicity of C-10 massoialactone towards red blood, vero and fibroblast cells in 16.15-16.30 Triana Hertiani vitro 16.30-16.45 OP 39: Expectorant syrup based on a combination of local herbs Dilfuza Mirakilova OP 40: Antibiofilm drug discovery: New topics in antimicrobial adjuvants for 16.45-17.00 Juan Bueno antibiofilm improvement OP 41: Study of low molecular proteins from soluble protein fraction of wheat 17.00-17.15 Nadejda Korablyova cultivated in Uzbekistan OP 42: Isolation and identification of polypeptides composition in seeds of the 17.15-17.30 Abulimiti Yili Chickpea after sprouting 17.30-18.30 Poster Session II (from number 101 on) 20.00 Symposium Dinner
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3rd October 2015, Saturday Session 8 Chair persons: Nurhayat Tabanca, V.P. Bruskov PL 11: Research into chemistry and biological activities of Nepeta and Scutellaria 08.30-09.00 Nilufar Mamadelieva (Lamiaceae) species of Uzbekistan PL 12: Cycloartane-type triterpenoid glycosides of astragalus species from the flora 09.00-09.30 İhsan Çalış of Turkey 09.30-10.00 PL 13: Cannabis based product development activities at Ole Miss Mahmoud A Elsohny 10.00-10.30 Session Break – Tea & Coffee Session 9 Chair persons: Yoshinori Asakawa, Jiangshan Shen 10.30-11.00 PL 14: Cytotoxic activity of biological activity substances Shakhnoz Azimova 11.00-11.30 PL 15: Essential oils as natural mosquito agents Nurhayat Tabanca PL 16: New quality monographs on TCM herbal drugs for the European 11.30-12.00 Gerhard Franz Pharmacopoeia PL 17: Synthesis and modifications of the deoxyvasicinone and mackinazolinone 12.00-12.30 Burkhon Zh. Elmuradov derivatives 12.30-13.30 Lunch Break Session 10 Hall A: Phytochemistry & Pharmacology Chair persons: Temel Özek, Firuza Tursunkhodjaeva 13.30-13.45 OP 43: The drug ekdinox as a new effective anthelmintic medicine J.I. Islamova 13.45-14.00 OP 44: Study of alkaloids of vincamine fraction of Vinca erecta Madina Mirzaeva 14.00-14.15 OP 45: Hybrid state of nitrogen in indoline alkaloids and their salt formation Bakhodir Tashkhodjaev 14.15-14.30 OP 46: Reaction of songorine with O-Nitrophenylisocyanate Nuridin Mukarramov 14.30-15.00 Session Break – Tea & Coffee 15.00-16.00 Closing ceremony Session 10 Hall B: Phytochemistry Chair persons: Gülmira Özek, R. Mukhamatkhanova OP 47: Sub-Milligram scale secondary metabolite hunting by NMR Spectroscopy; a Mahmut Miski 13.30-13.45 new dimeric spirooumarin from Neocryptodiscus papillaris OP 48: A fast and automatic determination of total polyphenols in plants using flow 13.45-14.00 Turghun Muhammad Injection analysis based on fiber optic detection 14.00-14.15 OP 49: LC-MS/MS Phenolic compound characterization of Salvia palestina from Turkey Fatih Göger OP 50: Assesment of cytotoxic and genotoxic potential of isolated compounds from 14.15-14.30 Didem Şöhretoğlu Geranium psilostemon 14.45-15.00 Session Break – Tea & Coffee 15.00-16.00 Closing ceremony 4th October 2015, Sunday 08.30-12.00 Sightseeing tour 1 12.00-14.00 Lunch at symposium hotel 14.00-18.00 Sightseeing tour 2
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TABLE OF CONTENTS PLENARY LECTURES PL-01 MEDICINAL PREPARATIONS BASED ON DITERPENOID ALKALOIDS ISOLATED FROM THE CENTRAL ASIAN PLANTS PL-02 Study on the Active Compounds of Ethnic Medicine and Rupestonic Acid Derivatives PL-03 ESSENTIAL OILS OF ACHILLEA SPECIES OF TURKEY PL-04 Chemistry and Biological Tests of Complex Natural Products from Medicinal Plants PL-05 The untapped potential of the African Herbal Pharmacopoeia PL-06 Phytochemistry of Liverworts: Bio-and Chemical Diversity and Biological Activity PL-07 MICROBIAL BIOTRANSFORMATION STUDIES ON ASTRAGALUS CYCLOARTANES PL-08 FrOm natural Tetrahydroprotoberberines (THPBs) to novel drug candidates PL-09 deuterium exchange OF α-METHYLENE GROUP PROTONS IN THE TRICYCLIC QUINAZOLIN4-ONES AND -4-THIONES PL-10 Polyphenolic compounds from various plant species growing wild in Turkey PL-11 RESEARCH INTO CHEMISTRY AND BIOLOGICAL ACTIVITIES OF NEPETA AND SCUTELLARIA (LAMIACEAE) SPECIES OF UZBEKISTAN PL-12 CYCLOARTANE-TYPE TRITERPENOID GLYCOSIDES OF ASTRAGALUS SPECIES FROM THE FLORA OF TURKEY PL-13 Cannabis Based Product Development Activities at Ole Miss PL-14 CYTOTOXIC ACTIVITY OF BIOLOGICAL ACTIVITY SUBSTANCES PL-15 Essential Oils As Natural Mosquito Agents PL-16 New Quality Monographs on Traditional Chinese Medicine (TCM) Herbal Drugs for the European Pharmacopoeia PL-17 SYNTHESIS AND MODIFICATIONS OF THE DEOXYVASICINONE AND MACKINAZOLINONE DERIVATIVES
2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18
oral presentatıons OP-01 ESSENTIAL OILS OF plantS OF CENTRAL ASIA OP-02 Chemıcal composıtıon of essentıal oıls from savory under dıfferent extractıon methods: Conventıonal dıstıllatıon, an ınnovatıve technıque steam dıstıllatıon, mıcrowave-assısted steam hydro-dıffusıon, and mıcrowaveassısted hydro-dıffusıon methods OP-03 Chemical composition and biological activity of essential oil of Chaerophyllum aromaticum L. from Turkey. OP-04 Lipids and Essential Oils of Arischrada bucharica (M.Pop.) Pobed. and Ziziphora pedicellata Pazij et Vved. Leaves OP-05 DEVELOPMENT OF THE TECHNOLOGY OF KROSTOPIDIN PREPARATION PRODUCTION FROM THE AERIAL PART OF CAPPARIS SPINOSA PLANT OP-06 Heavy Metal Contamination of Soil and Plants In The Vicinity of Blacksmith Workshop in Kazaure Town, Nigeria OP-07 PERSPECTIVES OF THE DEVELOPMENT OF LOCAL HEPATOPROTECTORS BASED ON PHYTOCOMPOSITION WITH PHOSPHOLIPIDS
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20 21
22 23 24 25 26
OP-08 Toxicity Analysis of Polychlorinated Dibenzofurans Using Global and Local Aromaticity Indices OP-09 Monoterpene esters of aromatic acids from the roots of Ferula calcarea OP-10 New coumarin derivatives with isopropyl group at C-8 of Peucedanum ruthenicum Bieb. OP-11 The structure and the biological activity of Seseli campestre angular pyranocoumarins OP-12 New Metabolites from the AlgaE-Derived Fungi Penicillium thomii Maire and Penicillium lividum Westling OP-13 InvestigationS OF natural productS from medicinal plantS of Kazakhstan OP-14 ON A FACILE METHOD FOR ENHANCED THROUGHPUT IN ISOLATION OF LUPEOL FROM MARANTHES POLYANDRA OP-15 Beneficial effects of clove on oxidative stress and pro-inflammatory cytokines (interleukin-1, 6 and TNF-α) produced by adipose tissue, in rats fed a high-cholesterol diet OP-16 Bioassay-guided isolation of sesquiterpene coumarins from Ferula narthex BoIss. A new anticancer agent OP-17 Pharmacology of succinate-containing aminothiols OP-18 The cytotoxic activity guided fractionation of Arum italicum Miller rhizomes OP-19 Anti-cancer effect of Curcuma longa rhizomes extract against Daudi and Jurkat cell lines evaluated by MTT assay and apoptosis activity OP-20 THE MOLECULAR MECHANISM OF INHIBITION OF CYCLOOXYGENASE BY FLAVONOIDS OP-21 Biologically active coumarins and chromones of roots, flowers and leaves of the Visnaga daucoides OP-22 NOVEL SESQUITERPENE COUMARIN ETHERS FROM THE DICHLOROMETHANE EXTRACT OF THE ROOTS OF HEPTAPTERA CILICICA OP-23 The Quality Evaluation of Ginseng Cultivated under Mountainous Forest OP-24 Purification of soybean lecithin from phosphatidic concentrate OP-25 A NEW SESQUITERPENE COUMARIN FROM FERULA OVINA OP-26 Contribution of different molecular and physiological mechanisms in the development of analgesic effects of diterpenoid alkaloids OP-27 DERIVATIVES OF CYCLOORBICOSIDE A, THEIR BIOLOGICAL ACTIVITY OP-28 Pharmacological activities of selected Algerian medicinal plants OP-29 SECONDARY METABOLITES OF Geranium PLANTS AND THEIR BIOLOGICAL ACTIVITY OP-30 Botanicals Risk Assessment in the Mediterranean Area (BRAMA): A Toxicological Study. OP-31 SESQUITERPENE LACTONES OF Artemisia L. GENUS OF THE UZBEK FLORA ASSIGNED TO MEDICINE OP-32 A NEW ENT-KAURANE TYPE DITERPENE DIGLUCOSIDE FROM PULICARIA ULIGINOSA OP-33 Investigation of alkaloids of Catharanthus roseus cultivated in Uzbekistan OP-34 Method for isolation iridoids from Phlomoides sp OP-35 PHYTOECDYSTEROIDS FROM PHLOMOIDES OSTROWSKIANA OP-36 EXTRACTION OF ESTERS FROM THE AERIAL PARTS OF FERULA TENUISECTA OP-37 Properties, structure and biological activity of polysaccharides from seeds of local species of Gleditsia and Crotalaria OP-38 Toxicity of C-10 massoialactone towards red blood, vero and fibroblasT cells in vitro OP-39 EXPECTORANT SYRUP BASED ON A COMBINATION OF LOCAL HERBS
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27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58
OP-40 Antimicrobial strategies in novel drug delivery systems, applications in the treatment of skin and soft tissue infections OP-41 STUDY OF LOW MOLECULAR PROTEINS FROM SOLUBLE PROTEIN FRACTION OF THE WHEAT CULTIVATED IN UZBEKISTAN OP-42 Isolation and identification of polypeptides composition in seeds of the Chickpea after sprouting OP-43 THE DRUG EKDINOX AS A NEW EFFECTIVE ANTHELMINTIC MEDICINE OP-44 Study of alkaloids of vincamine fraction of Vinca erecta OP-45 HYBRID STATE OF NITROGEN IN INDOLINE ALKALOIDS AND THEIR SALT FORMATION OP-46 REACTION OF SONGORINE WITH O-NITROPHENYLISOCYANATE OP-47 SUB-MILLIGRAM SCALE SECONDARY METABOLITE HUNTING BY NMR SPECTROSCOPY; A NEW DIMERIC SPIROCOUMARIN FROM NEOCRYPTODISCUS PAPILLARIS OP-48 A fast and Automatic Determination of Total Polyphenols in Plants Using Flow Injection Analysis Based on Fiber Optic Detection OP-49 Phenolic compound characterization of Salvia palestina Bentham from Turkey BY LC-MS/MS OP-50 Assesment of Cytotoxic and Genotoxic Potential of Isolated Compounds from Geranium psilostemon
59 60 61 62 63 64 65 66 67 68 69
poster presentatıons PP-01 Pharmacological properties of menthyl esters with inhibitory amino acids PP-02 Profiling of atractyligenin glucosides in the raw Arabica green coffee beans by UHPLC-TOF-MS/MS measurements PP-03 Composition of the Essential Oil of Endemic Centaurea dursunbeyensis Uysal & Kose From Turkey PP-04 ANTIBACTERIAL EFFECT OF ALKALOIDS AND POLYPHENOLS OF ALGERIAN MEDICINAL PLANT: HAPLOPHYLLUM TUBERCULATUM (FORSSK.) A.JUSS. PP-05 BIOACTIVE SUBSTANCES OF CEPHALARIA SYRIACA GROWING IN AZERBAIJAN PP-06 ANTIMICROBIAL ACTIVITIES OF ESSENTIAL OILS FROM 10 MEDICINAL AND AROMATIC PLANTS FROM ADAMAWA STATE, NIGERIA PP-07 IR SPECTROSCOPIC RESEARCH OF ENTEROSORBENT ZEROTOX PP-08 Biomimetic oxIdatIon-cyclIzatIon of E,E-germacranolIde hanphIllIne PP-09 ELECTROPHILIC CATALITIC ADDITION OF DITHIOLS TO (+)-CAMPHENE PP-10 VOLATILE COMPOUNDS of CYPERUS ROTUNDUS L. RHIZOMES from TURKEY PP-11 NEW SESQUITERPENES FROM THE MARINE-DERIVED FUNGUS PENICILLIUM THOMII PP-12 STUDY OF ACUTE TOXICITY OF INDOMETHACIN LIPOSOMAL OINTMENT PP-13 Essential oil composition and biological activities of Tanacetum haussknechtii (Bornm.) Grierson PP-14 Isolation of three new butyrolactone derivatives, toxins from Dendrobium nobile PP-15 Three New Clerodane Diterpenoids from the Roots of Polyalthia laui Merr PP-16 A Phytochemical Investigation of Homalium paniculiflorum PP-17 Study of the trimeric proanthocyanidins from the seed of Fraxinus americana PP-18 BIOACTIVE COMPONENTS OF CAMEL’S MILK PP-19 THE IN VITRO DIABETIC WOUND HEALING EFFECTS OF CRUDE extractS fROM Kazakhstan medIcInal plantS
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71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89
PP-20 CHOLINESTERASE AND α-AMYLASE INHIBITORY, ANTIOXIDANT AND ANTIMICROBIAL EFFECTS of Artemisia kotuchovii Kupr., AN ENDEMIC SPECIES FROM ALTAI REGION OF KAZAKHSTAN PP-21 THE IN VITRO CHARACTERIZATION OF BIOLOGICAL ACTIVITIES OF Artemisia sogdiana Bunge., AN ENDEMIC SPECIES FROM UZBEKISTAN PP-22 Chemical composition of lipids and essential oil of Ferula kuhistanica Korovin from Uzbekistan PP-23 CHEMICAL CHARACTERIZATION of Astrantia maxima Pallas. subsp. maxima VOLATILES PP-24 DEVELOPMENT OF AN OINTMENT WITH CHAMOMILE EXTRACT PP-25 PHARMACOGNOSTIC CHARACTERISTICS OF SOME SPECIES OF THE ARTEMISIA L. FROM BURYATIAN FLORA (RUSSIA) PP-26 Essential oil and fatty acid composition and biological activities of Achillea sivasica Çelik & Akpulat (Asteraceae) PP-27 Chemical Composition and Antimicrobial Activity of the Essential oil of Seseli salsuginea A. Duran et M. Çelik PP-28 STRUCTURE-ANTIBACTERIAL ACTIVITY RELATIONSHIP STUDY OF FLAVONES PP-29 Synthesis of ester derivatives of anacardic acid as antibacterial agent PP-30 A flavonoid with high antioxidant effect from Centaurea acaulis L. PP-31 IDENTIFICATION OF SECONDARY METABOLITES IN PHYSOSPERUM ACTAEFOLIUM USING THE COMBINED SYSTEMS HPLC-TOF/MS AND NMR PP-32 ANTIBACTERIAL POTENTIAL OF LEPIDIUM DRABA FROM ALGERIA PP-33 Chemistry, antioxidant and anticholinesterase activity of the essential oil of Hippomarathrum libanotis Koch. PP-34 Chemical Composition and Biological Activities of Comandra umbellata (L.) Nutt. PP-35 The Quality Evaluation of Ginseng Cultivated under Mountainous Forest PP-36 A new glycoside from marine-derived endophytic fungi PP-37 AngiogenIC MEDIATOR vascular endothelial growth factor in ischemic stroke PP-38 Research INTO antibacterial and antifungal activities of the basil (Ocimum basilicum L.) from Northeast of Algeria PP-39 REACTION OF SONGORINE WITH O-NITROPHENYLISOCYANATE PP-40 Cell culture of AJUGA TURKESTANICA (RGL.) BRIQ. AND IT’S biosynthetic activity PP-41 APPLICATION OF GROWTH REGULATOR OF UCHKUN ON COTTON TO ENHANCE RESISTANCE TO DISEASES PP-42 in vitro evaluation of INHIBITING AND GROWTH STIMULATING ACTIvitIES of the 2,5-disubstituted-1,3,4-OxaDIAZOLes PP-43 GROWTH-REGULATORY ACTIVITY OF RETKIL PP-44 ALKYLATION of p-CRESOL BY POLYPRENOLS PP-45 POLYISOPRENOIDS OF THE LEAVES OF NOVEL COTTON GRADES PP-46 THE INFLUENCE OF UCHKUN PREPARATION ON WHEAT YIELD PP-47 DEVELOPMENT OF THE METHOD FOR DETERMINATION OF THE MAIN COMPONENTS IN EXTRACTS OF LEONURUS TURKESTANICUS AND LEONURUS PANZERIOIDES BY 1H NMR SPECTROSCOPY PP-48 1H NMR SPECTROSCOPY METHODS FOR THE QUANTITATIVE CONTROL OF AGRICULTURAL AND PHARMACEUTICAL PREPARATIONS PP-49 Instant Granules as an Antithrombocytopenia using Phyllantus niruri L. Extract PP-50 ALKALOIDS OF SECURINEGA SUFFRUTICOSA INTRODUCED AT THE TASHKENT BOTANICAL GARDEN
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90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120
PP-51 The spatial structure of N- (3-bromo-4-hydroxy)-, (3-bromo-4-hydroxy-5methoxy)-, (2-bromo-3-hydroxy-4-methoxybenzyl)cytisines PP-52 COMPARISON OF THE CRYSTAL STRUCTURE OF VINERINE WITH MAJDINE AND ISOMAJDINE PP-53 CHEMICAL COMPONENTS OF PULICARIA GNAPHALOIDES PP-54 THE SURFACE TENSION OF SOLUTIONS BIOSURFACTANS PP-55 INTERACTION OF Α FORMYL-2,3-TETRAMETHYLENE-3,4-DIHYDROQUINAZOLIN-4-ONE TO AMINES PP-56 SYNTHESIS OF amides, imides and ISOQUINOLINEs ON THE BASE OF HOMOVERATRYLAMINE AND natural ACIDs PP-57 PLANTS OF THE GENUS GLEDITSIA ARE SOURCE OF TRIAKANTIN PP-58 THE SURFACE TENSION OF SOLUTIONS BIOSURFACTANS PP-59 TECHNOLOGY AND STANDARDIZATION OF CAPSULATED FORM BASED ON THE DRY EXTRACT OF HYPERICUM SCABRUM PP-60 DEVELOPMENT OF TECHNOLOGY AND STANDARDIZATION FOR TABLETS BASED ON THE DRY EXTRACT OF HYPERICUM SCABRUM PP-61 Effects of some diterpenoid alkaloids on the animal cognitive functions disturbed by nicotine PP-62 Influence of 2,3-pentamethylenе-3,4-dihydroquinazolon-4-one (pentazolon) on central adreno - and 5HT-receptors PP-63 Acaricidal activity of drugs based on the local flora PP-64 THYMOSTENIC ACTIVITY OF CYCLOSEVERSIOSIDE F IN THE PHYSIOLOGICAL EXPERIMENTS PP-65 DETERMINATION OF THE OPTIMAL PRESSING REGIMEN FOR AXARITMIN TABLETS PP-66 SELECTION OF EXCIPIENTS IN DEVELOPMENT OF AXARITMIN TABLET CORE PP-67 Mathematical planning of the extraction process of glacembrin from the raw material PP-68 STORAGE CONDITIONS OF GLACEMBRIN TABLETS PP-69 CHEMICAL COMPONENTS OF TOXIC FUNGUS STACHYBOTRYS HARTARUM PP-70 LOW MOLECULAR METABOLITES OF CRAMBE SPECIES PP-71 CRYSTAL STRUCTURE OF N-(ETHYL, ALLYLCARBAMOYL) СONVOLVINE PP-72 Alkaloids of Haplophyllum ramosissimum. the structure OF ramamidine PP-73 CUTICULAR LIPIDS OF THE PEEL OF LYCOPERSICUM ESCULENTUM PP-74 DEVELOPMENT OF TECHNOLOGY FOR OBTAINING TABLETS OF BIDENS TRIPARTITA DRY EXTRACT PP-75 DEVELOPMENT TECHNOLOGY OF CINAROSIDE TABLET PP-76 Polyprenol compounds of betula pendula and populus tremula and their analgesic activity PP-77 Phenolic Compound Determination of Chaerophyllum byzantinum Boiss by LCMS/MS. PP-78 PHYTOCHEMICAL AND TLC BIOAUTOGRAPHIC ANALYSIS OF STEREOSPERMUM KUNTHIANUM CHAM. LEAVES (BIGNONIACEAE) PP-79 ON PHARMACOLOGY OF DITERPENE ALKALOIDS BROUNIINE, ACETYLBROUNIINE, BENZOYLBROUNIINE PP-80 PHENOLIC COMPOUNDS OF THE LEAVES OF Pistacia vera PP-81 PHENOLIC SUBSTANCES FROM THE AERIAL PART OF Geranium charlesii PP-82 UnsaponifiED substances FROM FREE lipids OF Lagochilus inebrians seeds PP-83 METABOLITES OF THE AERIAL PART OF Anaphalis racemifera
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121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153
PP-84 AntiBACTERIAL Activity of the Essential Oils of Centaurea lycopifolia Boiss. et Kotschy and C. cheirolopha (Fenzl) Wagenitz From Turkey PP-85 PHYTOCHEMICAL CONSTITUENTS FROM ACACIA NILOTICA DELILE WITH KINASE INHIBITORY ACTIVITY PP-86 «Glycythrinat» new antiulcer drugs PP-87 QUANTITATIVE DETERMINATION OF THE MAJOR SUBSTANCE IN THE PREPARATION ALPEK PP-88 PURIFIcatıon technology of GLYCERIN FROM TECHNICAL RAW MATERIALS of OIL INDUSTRY PP-89 PURIFICATION TECHNOLOGY OF TECHNICAL IBUPROFEN PP-90 DEVELOPMENT OF PURIFICATION TECHNOLOGY OF TECHNICAL NIMESULIDE PP-91 A new stereoisomeric monoterpene glycoside of the Leaves of Clematis heracleifolIa PP-92 Study on the fatty acid composition of Vernonia anthelmintica (L.) Willd. seed oil extracted by supercritiCal CO2 fluid PP-93 COMPARABLE EVALUATION OF THE CYCLOSIVERSIOZIDE F AND CURANTYLUM EFFECTS ON THE BLOOD COAGULATION SYSTEM PP-94 Polysaccharides of Ferula kuhistanica and their biological activity PP-95 ANTI-DIABETIC COMPOSITION ON THE BASIS OF LOCAL HERBS PP-96 THE EFFECTS OF MINERAL FERTILIZERS ON ARTEMISININ CONTENT IN THE SAMPLES OF THE CULTIVATED Artemisia annua L. PP-98 PHARMACOLOGICAL CORRECTION OF THE DISTURB ADAPTIVE PROCESSES IN STRESSED ANIMALS BY PHYTOECDYSTEROIDS, CYCLOARTANE GLYCOSIDES AND FLAVONOIDS PP-99 Study of biotechnological properties of wheat quality PP-100 ANTHELMINTIC ACTIVITY IN THE RANKS OF NATURAL COMPOUNDS OF STEROID AND POLYPHENOLIC STRUCTURE PP-101 GAS CHROMATOGRAPHY/MASS-SPECTRAL STUDIES OF SCUTELLARIA COMOSA PP-102 A NEW ACYLATED AND OLEANANE-TYPE TRITERPENOID SAPONIN FROM GYPSOPHILA ARROSTII ROOTS PP-103 GROWTH-REGULATORY ACTIVITY OF RETKIL PP-104 PHENOLIC SUBSTANCES OF THE AERIAL PART OF Alhagi canescens PP-105 COMPONENTS OF POLYGONUM CORIARIUM PP-106 Chemical study of plants of Kazakhstan on content of sesquiterpene lactones PP-107 Composition of the essential oil of a monotypic plant Glaucosciadium cordifolium (Boiss.) Burtt et Davis from Turkey PP-108 PHYTOCHEMIAL SCREENING, ANTI-MICROBIAL AND MINERAL DETERMINATION OF BYRSOCARPUS COCCINEUS ROOT PP-109 PHYTOCHEMIAL SCREENING, ANTIMICROBIAL AND MINERALS DETERMINATION OF Leptadenia hastata Extracts PP-110 CYTOTOXIC ACTIVITY OF THE 1-ARyLTETRAHYDROISOQUINOLINE DERIVATIVES PP-111 PHYTOCHEMICAL STUDY AND BOINSECTICIDAL EFFECT OF THE CRUDE ETHaNOLIC EXTRACT OF THE PLANT ARTEMISIA JUDAICA (ASTERACEAE) AGAINST APHIS FABAE PP-112 HYPOGLYCEMIC AND HYPOLIPIDEMIC ACTIVITY OF THE TOTAL EXTRACTIVE PREPARATIONS FROM THE CENTRAL ASIAN PLANTS IN EXPERIMENTAL DIABETES PP-113 1, 1-DIPHENYL-2-PICRYLHYDRAZYL FREE RADICAL SCAVENGING EFFECT OF Combretum platypetalum LEAF EXTRACTS PP-114 In vitro Evaluation of Cytotoxic and Antimicrobial Potentials of the Saudi Traditional Plant Alhagi graecorum Boiss.
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154 155 156 157 158 159 160 161 162 163 164 165 166 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184
PP-115 Secondary metabolites and antioxidant activity of Limonium duriusculum (de Girard) Kuntze PP-116 SYNTHESIS OF ETHER ANALOGUES OF MANSONONE G AS ANTIBACTERIAL AGENTS PP-117 TRIBULUS TERRESTRIS GROWING IN GEORGIA: A RICH SOURCE OF STEROIDAL AND FLAVONOID GLYCOSIDES PP-118 Studies on the Production Technologys and Biological Activities of Abnormal Phlegm Munziq And Mushil PP-119 CRYSTAL AND MOLECULAR STRUCTURE OF SAWARANIN PP-120 Chemical constituents in fruits of Lycium barbarum (Goji) cultivated in Konya, Turkey PP-121 The relationships between phenolic contents and antimicrobial activity in propolis pp-122 Study of biotechnological properties of wheat quality PP-123 Hepatoprotective activities of Fraxinus angustifolia and Pistacia lentiscus extracts in mice intoxicated by aluminium. PP-124 Nebuloside B a triterpenoidal saponin as promising green corrosion inhibitor of aluminium in NaOH, H2SO4, NaCI solutions PP-125 CHEMICAL COMPOSITION OF THE T. cherlerioides var. isauricus Jalas ESSENTIAL OIL, FROM TURKEY PP-126 ANTIBACTERIAL ACTIVITY AND ESSENTIAL OIL COMPOSITION OF THE Achillea wilhelmsii C. Koch, FROM TURKEY PP-127 IMPROVEMENT OF TECHNOLOGY OF EXTRACTION OF SAFFLOWER OIL PP-128 WHEAT GERMS – VALUABLE RAW MATERIALS FOR EXTRACTION OF TOCOPHEROLS PP-129 BASIC CHARACTERISTICS OF EMULSIFIERS USED IN the PRODUCTION OF MARGARINE PP-130 THE ANALYSIS AND ESTIMATION OF FUNCTIONAL COMPOUNDS OF THE PHYTOGENESIS PP-131 SAFETY OF FUNCTIONAL COMPOUNDS OF THE PHYTOGENESIS PP-132 ABOUT SUPERFICIAL ACTIVITY OF FOOD EMULSIFIERS PP-133 FIRM SOAPS, SUPERFICIAL TENSION OF SOAP SOLUTIONS PP-134 Bio-active potential of ethnomedicinal plants of Kashmir Himalaya PP-135 AN ADVANCED WAY IN CREATING EFFECTIVE ANTIVIRALs PP-136 NEW LABDANE DITERPENOIDS AND THEIR ANTIMICROBIAL EVALUATION FROM MARRUBIUM VULGARE PP-137 POLYSACCHARIDE ANIONIC COMPOUNDS AS A SOLUTION agaınst BACTERIAL RESISTANCE PP-138 Synthesis and in Vitro anticancer activity of natural product analogs of 1,2,4-oxadiazoline and pyrazoline derivatives containing acridinyl against Cdc25B PP-139 HOMOGENOUS SULFATION AS A SAFE METHOD FOR THE PREPARATION OF SODIUM CELLULOSE SULFATES PP-140 Extraction and Analysis of Moss Secondary Metabolites PP-141 Evaluation of allicin and alliin content in Iranian garlic (Allium sativum L.) ecotypes PP-142 Study on the extraction of polyphenolic compounds in Xinjiang grape seeds and their antioxidant activity PP-143 NANOSTRUCTURED BIODEFENSIVES BASED ON ENCAPSULATION OF ESSENTIAL OILS PP-144 Phytochemical composition of the essential oil of different populations of two Mentha species PP-145 Efficiency of the essential oil of Rosemary against seven bacterial strains.
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185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215
PP-146 Quantification of rutin and chlorogenic acid in the extracts of leaves and fruits from three endemic Prangos species PP-147 Isolation and identification of β-sitosterol-3-O-β-D-glucopyranoside from leaf parts of Centaurea derderiifolia and its anticancer and antioxidant activities PP-148 Bioassay Guided Fractionation of the Chloroform Extract from Centaurea derderiifolia PP-149 A comparative study on antioxidant potentials of the various extracts from different parts of Euphorbia chamaesyce L. PP-150 Phenolic Compounds and Fatty Acid Composition of Euphorbia chamaesyce L. PP-151 ESSENTIAL OIL COMPOSITION AND ANTIOXIDANT PROPERTIES OF CENTAUREA CARIENSIS SUBSP. MACULICEPS (O. SCHWARZ) WAGENITZ PP-152 Simultaneous Determination of β–acetoxyisovaleryalkannin by HPLC in Arnebiae Radix PP-153 CHOLINESTERASE INHIBITORY ACTIVITY OF ORIGANUM VULGARE L. SUBSP. HIRTUM AND ITS CONSTITUENTS PP-154 Flavones from Endemic Centaurea kilaea Boiss. PP-155 Two sesquiterpenoides from Vernonia anthelmintica (L.) Willd. PP-156 Supercritical CO2 extraction of Nitraria sibirica Pall. seed oil and its fatty acid composition analysis PP-157 Determination and antıbacterıal actıvıty of polyphenols from pomegranate peel by LC-MS and quantitative analysis of major compounds PP-158 Antihypertensive activity of Ziziphora clinopodioides Lam. PP-159 Chemical Composition of Saussurea involucrata Seeds PP-160 CHEMICAL STUDY OF LEAVES OF Lycium barbarum PP-161 New alkaloids isolated from Fritillaria pallidiflora PP-162 Antioxidants from Ziziphora clinopodioides Lam. by combination of chromatographic techniques PP-163 INVESTIGATIONS INTO THE CHEMICAL PROFILE OF PRUNUS DULCIS NUTS PP-164 Anti-inflammatory effect of the pomegranate peel extract in RAW264.7 cells by suppression of NF-κB and MAPK signalLing PP-165 Structure-activity Relationships and NMR Features of Diterpenoid Alkaloids from Xinjiang Local Plants PP-166 C19-DITERPENOID ALKALOIDS FROM ACONITUM SOONGARICUM VAR. PUBESCENS PP-167 Characterization and identification of chemical components in Rosa rugosa Flowers by liquid chromatography-electrospray ionization quadrupole time-offlight tandem mass spectrometry PP-168 The Essential Oil Composition and Antimicrobial Activity of Nepeta cilicica Boiss. ex Benth. PP-169 Affinity material for esculin based on imprinted βETA-cyclodextrin polymers prepared in ionic liquid PP-170 CHEMICAL CONSTITUENTS OF EUPHORBIA SOONGARICA BOISS. PP-171 Study on Anti-Vitiligo activity of Kaliziri flavonoids PP-172 Identification of chemical components in the low-polarity part of Vernonia anthelmintica extract by HPLC-MS/MS PP-173 Chemical Constituents of Silene arenarioides Desf. And its Biological Activity PP-174 Separation of oleanolic acid from natural plant extracts using new type of molecularly imprinted polymers
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216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244
PP-175 PHENOLIC COMPOUNDS OF CAMPANULA BETULIFOLIA C. KOCH (ENDEMIC) FROM TURKEY PP-176 Comparison and Characterization of Sideritis caesarea (SC) Duman, Aytac & Baser Essential Oil Constituents Collected from Different Localities and in Periods PP-177 Antimicrobial, Antioxidant and Composition of the Essential Oils from Leaves and Aerial parts of Artemisia lehmaniana Growing in Iran PP-178 CHEMICAL CONSTITUENTS OF THE ROOTS OF ANACYCLUS PYRETHRUM (L) DC. PP-179 FAME COMPOSITION OF FOUR ORNITHOGALUM L. SPECIES GROWN IN TURKEY PP-180 Volatile Compounds of Roots, Aerial Parts and Flowers of Ferulago pachyloba (Fenzl) Boiss. (Apiaceae) Growing in Turkey and Determination of Their Antimicrobial Activities via Bioautography Method PP-181 Composition of the essential oil of endemic Stachys sericantha from Turkey PP-182 The GC-MS Analysis of Xinjiang Almond oil based on Fatty Acids PP-183 Pollen analysis and antimicrobial activity of Algerian honey against pathogenic microorganisms PP-184 Crop protection and preservation of environment: IN VIVO evaluation in vivo of bisacylhydrazine ecdysteroid mimics (RH-5849 and RH-5992) on pupae of Ephestia kuehniella PP-185 Spectrum-effect Relationship in Protein Tyrosine Phosphatase (PTP1B) Inhibition Effect of Carthamus tinctorius L. PP-186 Antioxidant, antimicrobial and cytotoxicity of extracts from Curtisia dentata (Burm.f) C.A. Sm. PP-187 Chemıcal Composıtıon oF Helianthemum sessiliflorum PP-188 THE INFLUENCE OF SALVIFOLIN ON ATP-DEPENDENT POTASSIUM CHANNEL IN RAT LIVER MITOCHONDRIA IN STREPTOZOTOCIN-INDUCED DIABETES PP-189 EFFECTs OF FLAVONOID cHRYSOERIOL ON CONTRACTILE ACTIVITY OF SMOOTH MUSCLE CELLS OF RAT AORTA PP-190 Research into Chemical Constituents and Pharmacological Effects of Euphorbia humifusa PP-191 Chemical composition and antifungal activity of essential oils of Artemisia herba alba Asso grown wild in Ouenza (Tebessa -Algeria) PP-192 Analysis of the Chemical Compositions from Subgenus Grammosciadium DC; G. confertum Hub.-Mor. & Lamond, G. cornutum (Nábělek) C.C.Towns., G. macrodon Boiss. and G. daucoides DC., growing in Turkey PP-193 NEW INTRODUCED COTTON SORT “BUKHARA-9” DOESN’T CONTAINING GOSSYPOL PP-194 Synergistic Effects Between the Essential Oil of Thymus numidicus Poir. and Amphotericin B PP-195 Histopathological effects of mixtures of insecticide in the hepatopancreas of terrestrial gastropod Helix aspersa PP-196 MICROBIAL BIOTRANSFORMATION OF OLEIC ACID AND THE CYTOTOXICITY OF BIOTRANSFORMATION MIXTURES PP-197 Herbal medicine in diabetics Ethnobotanical survey, phytochemical analysis and evaluation of the antioxidant activity of five medicinal plants PP-198 Isolation of secondary metabolites of Persicaria maculosa extract with GIRK channel-modulatory activity PP-199 Biological activities of Juniperus phonicea Tar, growing wild in Bechar region, south west of Algeria. PP-200 Alkaloids of Haplophyllum griffitianum
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XVI
245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 268 269 270
PP-201 Synthesis and Anti-Influenza Activity of Rupestonic Acid Derivatives PP-202 Pinus mugo Turra. essential oil, its fractions and selective antimicrobial drug combinations against resistant pathogens PP-203 On-line screening and identification of antioxidant phenolic compounds of Salvia aegyptiaca L. PP-204 Comparative studies on antisickling properties of brown and green leaves of Carica papaya Linn. (Caricaceae) PP-205 Bimolecular compounds on the basis of guaianolides and their biological activity PP-206 Chemical composition and biological activity of Artemisia essential oils
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271 272 273 275 276 277
PLENARY LECTURES
PL-01 MEDICINAL PREPARATIONS BASED ON DITERPENOID ALKALOIDS ISOLATED FROM THE CENTRAL ASIAN PLANTS Sh.Sh. Sagdullaev, B.T. Salimov, A.Z. Sadykov, F.M. Tursunkhodjaeva, F.N. Dzakhangirov
Acad. S.Yu.Yunusov Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent, Uzbekistan
Introduction Chemical investigations on alkaloid-containing plants of Aconitum leucostomum Vorosh., A.soongoricum Stapf., A.zeravshanicum Steinb., Delphinium rotundifolium Afan., D.semibarbatum Bienert. (Ranunculaceae family) widespread in the Central Asia have started at the end of 50s – start of 60s of XX century in Tashkent is an initial point of the complex investigation of Aconitum L. and Delphinium L. plants. Materials and Methods Modern phytochemical, chemical, instrumental and technological techniques have been used in the investigation. Results and Discussion More than 180 alkaloids have been isolated from the investigated plants of Aconitum L. and Consolida species, 100 of them are new. New alkaloids were 8 types of C20-diterpenoid, 2 types of C19-norditerpenoid, 2 types of C18-bisnorditerpenoid alkaloids. Extraordinary denudatine alkaloids containing saturated 15,16,17-trihydroxyor 15-hydroxy-16,17-methylenedioxygroups in D ring, the first representatives of lycoctonine bases with С(16)oxygroup or С(3),С(4)-epoxygroup are included in this class. Data on biogenesis of diterpenoid alkaloids referring to the chemosystematics of Ranunculaceae and Papaveraceae families have been obtained. Investigation of the structure-activity relationship among the isolated alkaloids and their derivatives led to the discovery of potent substances with antiarrhythmic, analgesic, curare-like, local anaestetic or spasmolytic activity. The correlation between antiarrhythmic, curare-like, spasmolytic activities of diterpenoid alkaloids and their derivatives and their structure types, nature and positional relationship of oxygen functional groups will be discussed. It was discovered that ester alkaloids 14-O-benzoyltalatisamine, lappaconitine, N-desacetyllappaconitine and 6-O-benzoylheteratisine were high effective antiarrhythmic substances. It was established that C20-diterpenoid alkaloids 1-O-benzoylnapelline, zeravshanisine and dihydroatisine displayed high antiarrhythmic, local anaestetic and analgesic activity. Antiarrhythmic preparations allapinin, antiarhytmin and dihydroatisine hydrochloride had been developed on the base of lappaconitine, N-desacetyllappaconitine and dihydroatisine alkaloids accordingly. The technology for obtaining antiarrhythmic preparations allapinin, axaritmin, antiarhytmin, aklezin and dihydroatisine hydrochloride had been developed. Technology for obtaining the drug substance of new preparation antiarhytmin from the wastes of allapinin manufacture had been created. A number of high active substances with antiarrhythmic, analgesic, curare-like, local anaestetic and spasmolytic activity are used as chemical instruments for medical and biological investigations.
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PL-02 Study on the Active Compounds of Ethnic Medicine and Rupestonic Acid Derivatives Haji Akber Aisa, Jiang-yu Zhao, Qiao-ying Lv
Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Science; Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi, Xinjiang 830011, PR China
Medicinal plants distributed in the Central Asia and Xinjiang of China provides abundant and precious medicinal resources for the Traditional Uyghur Medicine in treating diseases. Euphorbia sororia A. Schrenk, an annual herb, has been used to cure abdominal pain, abdominal distention, skin disease and paralysis. [1] Until now, phytochemical investigations on fruits of E. sororia A. Schrenk and the whole plant of E. macrorrhiza C. A. Mey yielded 38 jatrophane diterpenoids, 25 of which are new compounds. The multidrugresistance reversal activity was also tested on KBv200 cells and compound ES2 (3μM) displayed strong multidrug resistance reversal activity, outperforming the positive control-Verapamil at 10μM. [2,3] Artemisia rupestris L. is known to be effective as antiviral, antiallergic, antitumour, antiinflammatory, antibacterial agents. Sesquiterpenoids, flavonoids and alkaloids compounds are the main ingredients.[4] Rupestonic acid as a sesquiterpene with multifunctional groups is its active ingredient. The activity screening showed that it exhibits certain inhibition against influenza B virus with IC50 value 115.7 μM. To improve biological activity of rupestonic acid, more than 300 rupestonic acid derivatives with modification of carboxyl group and carbonyl group have been synthesized in our laboratory and the activity against influenza has been evaluated.[5-8] In vivo experiments of four active compounds is under way. References 1. Huang Y, Aisa HA. Jatrophane diterpenoids from Fructus Euphorbia sororia. Phytochem Lett . 2010, 3:176-80. 2. Huang Y, Aisa HA. Three new diterpenoids from Euphorbia sororia L. Helv Chim Acta 2010, 93: 1156-61. 3. Dongli Lu, Yongqiang Liu, Haji Akber Aisa, Jatrophane diterpenoid esters from Euphorbia sororia serving as multidrug resistance reversal agents. Fitoterapia, 2014, 92: 244-251. 4. Y. Liu, W. Liu, Pharmacography of Uighur, Part I, Xinjiang People’s Publishing House, Urumqi, 1986, 3-4. 5. Jian-ping Yong, Qiao-ying Lv and Haji Akber Aisa.*Acrylic Acid (Rupestonic Acid) Amide Derivatives and in vitro Inhibitive Activities against Influenza A3,B and Herpes Simplex Type 1 and 2 Virus. Bull. Korean Chem. Soc. 2009, Vol. 30, No. 2 435 6. Y. W. He, C. Z. Dong, J. Y. Zhao, L. L. Ma, Y. H. Li, H.A. Aisa, 1,2,3-Triazole-containing derivatives of rupestonic acid: Click chemical synthesis and antiviral activities against influenza viruses, European Journal of Medicinal Chemistry, 2014, 76: 245-255. 7. J. Y. Zhao, H.A. Aisa, Synthesis and anti-influenza activity of aminoalkyl rupestonates, Bioorganic & Medicinal Chemistry Letters, 2012, 22: 2321–2325; c). J.Y. Zhao, H.A. Aisa, Synthesis of novel isoxazole contained rupestonic acid derivatives and in vitro inhibitory activity against influenza viruses A and B, Chinese Journal of Organic Chemistry, 2012, 32(2): 333-337. 8. J. P. Yong, H.A. Aisa, L. F. Nie, Synthesis of rupestonic acid benzyl ester derivatives and in vitro anti influenza virus and herpes simplex type I and viruses, Chinese Journal of Organic Chemistry, 2009, 29(10): 1640-1644.
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PL-03 ESSENTIAL OILS OF ACHILLEA SPECIES OF TURKEY K. Husnu Can BASER1,2 1 2
Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470 Eskişehir, Turkey King Saud University, College of Science, Botany and Microbiology Department, P.O. BOX 2455, Riyadh 11451, Saudi Arabia
The genus Achillea (Asteraceae) is represented by 115 species in the Northern Hemisphere. In the flora of Turkey, 50 species and altogether 58 taxa have been recorded, 31 being endemic. So far, 27 Achillea taxa growing wild in Turkey have been studied for their essential oils. Most have been characterized by the occurrence of camphor and 1,8-cineole as main constituents in their oils. This paper will review the essential oil compositions of A. aleppica subsp. aleppica, A. biebersteinii, A. biserrata, A. cappadocica, A. cretica, A. coarctata, A. cucullata, A. falcata, A. filipendulina, A. formosa subsp. amanica, A. goniocephala, A. ketenoglui, A. lycaonica, A. magnifica, A. millefolium subsp. millefolium, A. multifida, A. nobilis subsp. neilreichii, A. phrygia, A. pseudoaleppica, A. salicifolia subsp. salicifolia, A. schischkinii, A. sieheana, A. tenuifolia, A. teretifolia, A. vermicularis, A. wilhelmsii.
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PL-04 Chemistry and Biological Tests of Complex Natural Products from Medicinal Plants Jian-Min Yue
State Key Laboratory of Drug Research, Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zhuchongzhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203 P. R. China
Chemical studies on a large number of Chinese medicinal plants (including TCM) have led to the identification of a big array of structurally interesting and/or bioactive components (1−8), e.g. anticancer, antiHIV and immunosuppressive agents [1,2]. Some compounds have been selected as lead structures for our drug development program, and over one hundred of modified chemical entities with significantly improved activities were also obtained; biological evaluation showed that some of the compounds exhibited remarkable anticancer (both cytotoxic and antiangiogenesis), immunosuppressive and antiHIV activities; several groups of bioactive compounds showed very clear structure activity relationships; A few of structurally interesting and biologically important compounds have been synthesized [2]. Our studies have provided good scientific background for drug development and understanding of the function and toxicity of the involved medicinal plants.
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References 1. For reviews on structurally diverse and biologically active natural compounds, see a) Hua Zhang, Hong-Bing Liu, and JianMin Yue, Chem. Rev., 2014, 114, 883. b) Sheng-Ping Yang, Jian-Min Yue, Acta Pharm. Sin., 2012, 33, 1147. c) Shang-Gao Liao, Hua-Dong Chen and Jian-Min Yue, Chem. Rev., 2009, 109, 1092. 2. a) Jin-Biao Xu, Hua Zhang, Li-She Gan, Ying-Shan Han, Mark A Wainberg, and Jian-Min Yue, J. Am. Chem. Soc., 2014, 136, 7631. b) Hua Zhang, Chuan-Rui Zhang, Kong-Kai Zhu, An-Hui Gao, Cheng Luo, Jia Li, and Jian-Min Yue, Org. Lett., 2013, 15, 120. c) Bo Zhang, Yao Wang, Sheng-Ping Yang, Yu Zhou, Wen-Bin Wu, Tang Wei, Jian-Ping Zuo, Ying Li and Jian-Min Yue, J. Am. Chem. Soc., 2012, 134, 20605. d) Yao Wang, Quan-Fang Liu, Ji-Jun Xue, Yu Zhou, Huang-Chao Yu, Sheng-Ping Yang, Bo Zhang, Jian-Ping Zuo, Ying Li, and Jian-Min Yue Org. Lett., 2014, 16, 2062-2065. e) Jia Liu, Xiu-Feng He, Gai-Hong Wang, Emilio F. Merino, Sheng-Ping Yang, Rong-Xiu Zhu, Li-She Gan, Hua Zhang, Maria B. Cassera, He-Yao Wang, David G. I. Kingston, and JianMin Yue, J. Org. Chem., 2014, 79, 599-607. f) Sheng-Ping Yang, Xiao-Wei Zhang, Jing Ai, Jin-Biao Xu, Bo Zhang, Zu-Shang Su, Ying Wang, Lu Wang, Jian Ding, Mei-Yu Geng, and Jian-Min Yue, J. Med. Chem., 2012, 55, 8183-8187.
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PL-05 The untapped potential of the African Herbal Pharmacopoeia Ameenah Gurib-Fakim
CIDP R & I, BioPark Mauritius, Socota Phoenicia, Mauritius
[email protected]
The Association of African Medicinal Plants Standards (AAMPS) has already showed the way by highlighting the importance of plant standards through the publication of the ‘African Herbal Pharmacopoeia’ (AfHP) in 2010. To date, AfHP has regrouped 51 important African medicinal plants. With thousands of important medicinal plants growing on the continent and whose true value has not yet been assessed, the potential for discovering new products both for human or animal welfare is enormous. Subsequent to the publication of this pharmacopoeia, a major effort has been undertaken to develop standards for African medicinal plants and among the most important ones are: Good Agricultural Practices, Good Collection practices amongst others. The elaboration of these standards with ARSO (African Standards Office in collaboration with the TBT Program of the ACP group, is a good step forward into ensuring future intra-continental trade on this commodity and at the same time ensure the sustainability of this important resource. This presentation will report on the African Herbal Pharmacopoeia, the outcome of the elaboration of African Plant Standards and the work being carried out at the present at the CIDP Research and Innovation on adding value to this important resource. At CIDP R & I, attention is being given to their cosmetic, nutrition and pharma potential. The importance of being in conformity with the international prevailing regulations (such as the Chinese List of Authorized Plants) will also be discussed.
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PL-06 Phytochemistry of Liverworts: Bio-and Chemical Diversity and Biological Activity Yoshinori Asakawa
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan
[email protected]
Over several hundred new organic compounds have been isolated from the liverworts (Figs. 1 and 2) and more than 40 new carbon skeletal terpenoids and aromatic compounds found in this class. Most of liverworts elaborate characteristic odiferous, pungent and bitter tasting compounds many of which show, antimicrobial, antifungal, antiviral, allergenic contact dermatitis, cytotoxic, insecticidal, anti-HIV, superoxide anion radical release, plant growth regulatory, neurotrophic, NO production inhibitory, muscle relaxing, antiobesity, piscicidal and nematocidal activity .
Fig. 1. Marchantia polymorpha
Fig. 2. Plagiochila ovalifolia
Marchantins [Marchantin A (1),C (2)], riccardin [riccardin C (3,4)], isoplagiochin (5,6) and perrottetin (7,8) series and the other bis-bibenzyls which are isolated from the liverworts, (Fig. 1,2) and M. paleacea var. diptera, Riccardia, Reboulia, and Radula species showed cytotoxic, anti-HIV and anti-influenza, antitumor activity and muscle relaxing activity [1-3]. The present paper concerns with the biologically active terpenoids and bis-bibenzyls from liverworts. OH
OH
R1
O
OH
O
OR1
OH
O
R2
R3 R O OH
R2 1: Marchantin A: R1=OH; R2=R3=H 2: Marchantin C: R1=R2=R3=H
RO 3: Riccardin A: R=Me 4: Riccardin C: R=H
OH
O HO
HO 5: Isoplagochin A: R=H 6: Isoplagiochin B: R=OH
HO
7: Perrottetin E: R1=R2=H 8: Perrottettin F: R1=H; R2=OH
REFERENCES 1. Asakawa,Y. (1982)Progress in the Chemistry of Organic Natural Products. 42, 1-285. 2. Asakawa,Y. (1995) Progress in the Chemistry of Organic Natural Products. 65, 1-618. 3. Asakawa, Y., Ludwiczuk,A., Nagashima,F. (2013) Progress in the Chemistry of Organic Natural Products. 95, 1-796.
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PL-07 MICROBIAL BIOTRANSFORMATION STUDIES ON ASTRAGALUS CYCLOARTANES Erdal Bedir
Ege University, Engineering Faculty, Department of Bioengineering, Bornova, 35100-Izmir, Turkey
[email protected]
Biotransformation is the chemical modifications that occur when enzymes or whole cell systems are used as catalysts. This is an alternative tool with great potential, especially for the development of sustainable technologies for the production of chemicals and drugs. Biotransformation is a useful method for production of new potent molecules, overcoming the problems associated with chemical sysnthesis reactions/enhancement of the productivity and providing the basic information needed to elucidate the biosynthetic pathways. Producing large amounts of biomass and having great enzyme diversity with chemo-, regio- and enantio-selective catalytic abilities make microbial systems logical choice for biotransformation studies (1,2). Saponins are generally high-molecular weight secondary metabolites. They are utilized in cosmetic to pharmaceutic, beverage to sugar industries. These compounds have received considerable attention in drug discovery studies due to their wide range of bioactivities including cytotoxic, antiinflamatory, vasoprotective, hypocholesterolemic, immunomodulatory, hypoglycemic, molluscicidal, antifungal, antiparasitic, antimutagenic, antiviral, anti-HIV, analgesic. Saponins can be divided into two main classes, the triterpenoid and the steroid saponins. There has been extensive search on steroidal saponins, considered as one of the most marketed pharmaceutical products. Besides being an important starting material for the production of steroidal hormones, there are many steroidal compounds as active pharmaceutical ingredients available in the market (antiinflammatory, antitumor, antimicrobial, antiviral, anticonvulsant, antiallergic). From a bioactivity perspective, the most important triterpenoid structures are recognized as oleanane, ursane, lupane, and dammarane carbon skeletons, which are also commercially available for further semi-synthesis and biotransformation studies (3). Since drug-discovery programs on the triterpenoids have mainly focused on these skeletons providing extensive bioactivity data, the less common miscellaneous aglycones such as cycloartanes, lanostanes and hopanes have been disregarded for long time. The cycloartanes, unique triterpenoids with a characteristic 9,19-cyclopropane ring, occupy a special position among low molecular bioregulators since cycloartenol is a key intermediate in the biosynthesis of different phytosterols. For this reason, cycloartenol and its weakly polar derivatives are widespread in the plant kingdom. The plants of Astragalus genera are the richest source of this class of compounds. Cycloastragenol (CA), is the main sapogenol of many cycloartane-type glycosides found in the Astragalus genus. Recently CA, 20(R),24(S)-epoxy-3β,6α,16β,25-tetrahydroxycycloartane, has attracted attention due to its unique bioactivity, viz., telomerase activation (4). Taking into account, the results of our comprehensive studies and preliminary screenings in addition to recent progress in the literature, our research group has decided to focus on Astragalus cyloartanes to form a compound library for advance bioactivity studies such as anti-cancer, anti-aging and anti-inflammatory. Therefore the microbial transformation studies were conducted on 3 cycloartane-type sapogenols (Cycloastragenol, astragenol and cyclocanthogenol) with the bacteria Nocardia sp. NRRL 5646, Mycobacterium sp. NRRL 3683 and Mycobacterium sp. NRRL 3805, and the fungi Cunninghamella blakesleeana NRRL 1369 and Glomerella fusarioides ATCC 9552, commonly used microorganisms for the biotransformation of natural products particularly for saponins. The unique enzyme system of the microorganisms resulted hydroxylation, cyclization, glycosidation, dehydrogenation and oxidation reactions. Structures of the new metabolites were elucidated by 1-D (1H, 13C, NOESY), 2-D NMR (DQF-COSY, HMBC, HMQC, NOESY) and HR-MS analyses. Based on these results it was evident that both fungi had extensive ability to modify cycloartane nucleus compared to the bacteria. Details of our biotransformation studies will be presented.
References 1. Borges, K.B., Borges, W.S., Duran-Patron, R., Pupo, M.T., Bonato, P.S., Collado, I.G. 2009. Stereoselective biotransformations using fungi as biocatalysts. Tetrahedron: Asymmetry, 20: 385–397. 2. Leresche, J.E., Meyer, H-P. 2006. Chemocatalysis and Biocatalysis (Biotransformation): Some Thoughts of a Chemist and of a Biotechnologist. Organic Process Research & Development, 10: 572-580. 3. Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, M., Biedermann, D., 2006. Pharmacological activities of natural triterpenoids and their therapeutic implications. Natural Product Reports, 23: 394-411. 4. Harley, C.B., Khar, S.P., Ramaseshan, M., Ramiya, P., Pirot, Z.Z., Fauce, S., Lin, T. Compositions and Methods for Increasing Telomerase Activity, US Patent 20100292197 A1, Nov. 18 2010.
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PL-08 FrOm natural Tetrahydroprotoberberines (THPBs) to novel drug candidates Jingshan Shen
Shanghai Institute of Materia Medica, Chinese Academy of Sciences,Shanghai, PR China
Traditional Chinese medicines indicate hug clues for the potential clinical efficacy in treatment of a wide range of symptoms. Here is a story again that the drug candidates in the therapeutic field of central nerves system (CNS) are inspired from the analysis, identification, modification, and bioactivity evaluation of the ingredients of Chinese herbs of Yan-Hu-Suo (Corydalis yanhusuo W. T. Wang ex Z. Y. Su et C. Y. Wu) and Qian-Jin-Teng (Stephania japonica (Thunb.) Miers).
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PL-09 deuterium exchange OF α-METHYLENE GROUP PROTONS IN THE TRICYCLIC QUINAZOLIN-4-ONES AND -4-THIONES М. G. Levkovich,1 B.Zh. Elmuradov,1 Kh. М. Shakhidoyatov,1 N.D. Abdullayev1
Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Mirzo-Ulugbek str., 77. , Tashkent, Uzbekistan
[email protected]
1
Introduction The hydrogen atoms of α-methylene groups of the alkaloids deoxyvasicinone (2,3-trimethylene-3,4– dihydroquinazolin-4-one, 1), mackinazolinone (2,3 - tetramethylene-3,4- dihydroquinazolin-4-one, 2), their thioanalogues - deoxyvasicinethione (2,3-trimethylene-3,4-dihydroquinazolin-4-thione, 5), mackinazolinethione (2,3-tetramethylene3,4-dihydroquinazolin-4-thione, 6), and also their homologs (3, 4, 7) are capable of substitution reactions by various electrophilic particles (Shakhidoyatov Kh. M., 1998; Shakhidoyatov Kh. M. et al., 2014). During the obtaining of these derivatives and research into process regularities an unusual property of the called systems was revealed. α-Protons of the methylene group in a series of compounds 1-7 in the deuterated solvents are exchanged in deuterium: X 5 7
3
N
( )n
1
9
1-7
H H (D) (D)
N
1-4, X=O, n=1-4 5-7, X=S, n=1-3
Materials and Methods Deoxyvasicinone, mackinazolinone, deoxyvasicinethione, mackinazolinethione, deuterium exchange, methods of NMR1H- spectroscopy. Results and Discussion In this work, deuterium exchange rate of α-methylene group hydrogen atoms of the compounds 1-7 in the neutral, alkaline and acid conditions was studied. It was found, that exchange rate depends on methylene group quantity of polymethylene chains and conditions of reaction environment. The faster D-exchange takes place for mackinazolinone 2 and more slowly or even at all doesnot take place for its homologues 3, 4 and 7. Exchange rate increases by increasing the basicity as well as acidity of an environment. In the neutral conditions (CD3OD) deuterium exchange was observed only for mackinazolinone. In present work modelled and estimated some possible mechanisms of deuterium exchange and connection of this process on molecule’s structure and environment conditions. Acknowledgments We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (Project FA-F7-T207). REFERENCES 1. Shakhidoyatov, Kh. M., 1988. Quinazol-4-ones and their biological activity, FAN, Tashkent, 58-81. 2. Shakhidoyatov, Kh. M., Elmuradov, B. Zh., 2014. Tricyclic quinazoline alkaloids: isolation, synthesis, chemical modification and biological activity. Chemistry of Natural Compounds, 50: 781-800.
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PL-10 Polyphenolic compounds from various plant species growing wild in Turkey H. Kırmızıbekmez
Department of Pharmacognosy, Faculty of Pharmacy, Yeditepe University, 34755, Kayışdağı, Istanbul, Turkey
[email protected]
Secondary metabolites are produced by plants for different purposes such as protecting the plants against insects and herbivores, adaptation to environmental challenges as well as pollination and seed dispersal. Plant secondary metabolites have long been excellent sources for searching new drug candidates, food additives and cosmetics. Polyphenolic compounds constitute the second largest group of secondary metabolites after terpenoids and steroids. There is a growing interest on phenylethanoid glycosides due to their interesting biological activities and chemotaxonomic significance. Flavonoids are usually regarded as universal plant pigments, which are widely distributed in higher plants. Isoflavonoids, on the contrary, have limited distribution in plant kingdom, which are particularly confined to Fabaceae family. Chemical and structural variations are plentiful in both flavonoid and isoflavonoid type natural products. Turkey has a rich flora due to its geographical location as well as its climatic conditions. Given the richness in biodiversity of plants and their folkloric use, Turkey provides a tremendous source for scientists to obtain new bioactive metabolites on the way to discover new drug leads. In this presentation, it is aimed to report the recent results on the isolation and structure elucidation of new polyphenolic compounds belonging to phenylethanoid glycosides, flavonoids, isoflavonoids and phenolic acid chemical classes. The compounds were obtained from different species, mainly of the genera Digitalis, Glycyrrhiza, Asperula and Vitex collected from their natural habitat in Turkey. The isolation and purification of the compounds were carried out by using various chromatographic techniques including C18-MPLC, SiO2 and Sephadex LH20 column chromatography. The structures were determined by extensive 1D and 2D NMR experiments as well as MS analyses. This presentation will particularly focus on the structure elucidation of rare and new polyphenolic compounds.
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PL-11 RESEARCH INTO CHEMISTRY AND BIOLOGICAL ACTIVITIES OF NEPETA AND SCUTELLARIA (LAMIACEAE) SPECIES OF UZBEKISTAN Nilufar Z. Mamadalieva
Institute of the Chemistry of Plant Substances AS RUz, Tashkent 100170, Mirzo Ulugbek Str 77, Uzbekistan
[email protected]
Introduction The Lamiaceae, is of considerable economic importance, containing herbs or shrubs of various sizes, rarely trees. Many species of this family have horticultural value; many used as culinary herbs, or in perfumery and many are used medicinally. The main centre of diversity is the Mediterranean region to Central Asia. About 40 genera with ± 220 species of Lamiaceae occur in the Uzbekistan. The genus Nepeta is represented by 18 species and number of the species of the genus Scutellaria in Uzbek flora is 32 (Vvedenskiy, 1961). Materials and methods We have analyzed essential oils of aerial parts of the following species: Nepeta alatavica Lipsky, N. nuda L., N. olgae Regel, Scutellaria immaculata Nevski ex Juz., S. schachristanica Juz. and S. ramosissima M. Pop. The oils were analyzed by GC and GC-MS. GC-, LC-, EI-MS and PTLC analysis were performed as discussed in our previous publications (Mamadalieva et al., 2014). Antimicrobial activity was studied in vitro against a range of bacteria and fungi using diffusion and microdilution methods. Cytotoxic activity of the samples was assessed using MTT. The antioxidant activity of the individual compounds and extracts were evaluated using DPPH* test. Results and discussion GC-MS analysis allowed identification of 43, 49 and 31 components in N. alatavica, N. nuda and N. olgae, which made up 99.98, 99.94 and 87.34% of the total oil composition. The major components of the essential oils of Nepeta species were nepetalactone, acetylcyclohexene, cineole, germacrene D, trans-caryophyllene. In Scutellaria the major compounds were acetophenone, eugenol, thymol, linalool, β-terpineol. Overall, individually 38, 30 and 29 constituents were identified in the aerial parts of S. immaculata, S. schachristanica and S. ramosissima essential oils representing 98.92, 99.95 and 99.03% of the total, respectively. The major components of the nonpolar fraction of S. ramosissima were determined as heneicosane (12.18%), palmitic acid (11.79%), acetovanillone (6.28%), 5,6-dihydroxy-7,8-dimethoxyflavone (31.87%), (9Z)-octadecenoic (oleic) acid (8.21%), stigmasterol (2.68%), β-sitosterol (2.65%) and 5,2’-dihydroxy-6,7,8,6’-tetramethoxyflavone (2.13%) using GC-, LC-, and EI-MS. In addition, 5,6-dihydroxy-7,8-dimethoxyflavone was isolated from the same fraction by PTLC. Extracts and individual compounds from the species were subjected to tests for antibacterial, anticancer and antioxidant activities. The chloroform extract of S. ramosissima has antimicrobial activity against Streptococcus pyogenes (MIC = 0.03 mg/ ml). The CHCl3 extract of S. ramosissima inhibited the cell growth of HeLa, HepG-2 and MCF-7 cells with IC50 values of 9.25, 12.83 and 17.29 µg/ml, respectively. Among the tested samples the essential oils of N. alatavica and water extracts of Scutellaria species exhibited pronounced antioxidant activity. Acknowledgement Financial support by DAAD and UNESCO-L’ORÉAL foundation is gratefully acknowledged. ReferenceS 1. Mamadalieva, N.Z., Sharopov, F., Girault, J-P., Wink, M., Lafont, R. 2014. Phytochemical analysis and bioactivity of the aerial parts of Abutilon theophrasti (Malvaceae), a medicinal weed. Natural Product Research, 28(20): 1777-1779. 2. Vvedenskiy, A. 1961. Flora of Uzbekistan. АS RUz Publ. Fan, Tashkent, pp. 270–292.
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PL-12 CYCLOARTANE-TYPE TRITERPENOID GLYCOSIDES OF ASTRAGALUS SPECIES FROM THE FLORA OF TURKEY İhsan Çalış
Near East University, Faculty of Pharmacy, Department of Pharmacognosy, Lefkoşa, T.R.N.C.
[email protected]
The largest genus in the Angiosperms is Astragalus L. (milkvetch, locoweed; Turkish names: Geven, kitre). It comprises more than 2200 species distributed mainly in the North and South America, North Africa, Sahara, and Asia. The flora of Turkey exhibiting more than 425 Astragalus species is one of the richest one in the world. Astragalus species have been a valuable rural crop yielding gum tragacanth for many years not only in Turkey, but also in Iran. The roots of Astragalus species are well-known in traditional Chinese and Japanese medicine for the treatment of nephritis, diabetes, leukemia, uterine cancer and also are used as an antiperspirant, vasodilator, analgesic, sedative, hepatoprotective and diuretic. Astragalus species are known to be rich in two major classes of biologically active compounds, polysaccharides and saponins. The isolation of cycloartanes was firstly reported from A. sieversianus (Svechnikova et al., 1981). For us, decisive basis for the studies of the phytochemical and activity has been upon an observation in the usage of the roots of an unknown Astragalus species against leukemia in South East Anatolia in 1996. The glycosides having a novel cycloartane skeleton were isolated as major components of this unknown plant material. The existence of the same compounds in the roots of A. oleifolius were reported later (Çalış et al., 1996) confirming the proposal. Further investigations on the Astragalus species led us to show their additional traditional uses such as wound healing and tonic activities in Turkey. As one of the earlier studies, eight cycloartane glycosides isolated from the roots of A. melanophrurius were evaluated in a number of biological test systems. They were relatively inert in a variety of assay systems relevant to cancer chemopreventation. However, each compound tested was able to stimulate human lymphocyte proliferation in the concentration range of 0.01 -10µg/ml. At higher concentrations (100 or 200 µg/mI), inhibition of thymidine incorporation was observed. The immunomodulatory activity of cycloartanes was found relatively potent and thereby deserved further attention (Çalış et al., 1997). Thus, in addition to A. oleifolius and A. melanophrurius, we have further studied some Astragalus species, including A. microcephalus, A. trojanus, A. cephalotes, A. vulneraria, A. zahlbruckneri, A. prusianus, A. lucitanicus, A. baibutensis, A. macrocephalus, A. elongatus, A. campylosema and A. isaricus. These studies resulted in the isolation of about 60 cycloartane-type glycosides. Furthermore, we have studied some additional biological activities of the cycloartane-type compounds isolated from the Astragalus species. The results were very promising subject in terms of drug discovery studies. The richness in structural diversity of cycloartanes and as well the vast number of Astragalus species have provided ample motives for scientific investigation. References 1. Svechnikova, A.N., Umarova, R.U., Gorovits, M.B., Seitanidi, K.L., Rashkes, Y.V., Yagudaev, M.R., Abubakirov, N.K. (1981). Triterpene Glycosides of Astragalus and their genins. II. Structure of Cyclosieversigenin. Khim. Prir. Soedin., No 1, 67-76. 2. Çalış, I., Zor, M., Saraçoğlu, I., Isimer, A., Ruegger, H., 1996. Four novel cycloartane glycosides from Astragalus oleifolius, Journal of Natural Products 59: 1019-1023. 3. Çalış, İ., Yürüker, A., Tasdemir, D., Wright, A.D., Sticher, O., Luo, Y.-D., Pezzuto, J.M., 1997. Cycloartane Triterpene Glycosides from the Roots of Astragalus melanophrurius. Planta Med. 63: 183-186.
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PL-13 Cannabis Based Product Development Activities at Ole Miss Mahmoud A. ElSohly
Research Professor, National Center for Natural Products Research Professor of Pharmaceutics and Drug Delivery, School of Pharmacy University of Mississippi, Oxford, MS (USA)
The cannabis plant Cannabis Sativa is one of the oldest medicinal plants known to man. The plant and products thereof have been reported for the treatment of many disease conditions, and extracts of cannabis have been part of several pharmacopeias including the USP until 1937 where cannabis preparations were classified as Schedule I drugs, indicating no recognized medicinal values, but with high abuse potential. Renewed interest in the use of cannabis derived preparations reemerged in the 1960’s when the structure of the active compounds in cannabis (Δ9 tetrahydrocannabinol or THC) was determined in 1964. The drug is currently approved for the treatment of nausea and vomiting in cancer patients receiving chemotherapy and for appetite stimulation in AIDS patients with the Wasting Syndrome, formulated in sesame seed oil as soft gelatin capsules for oral administration. Because of issues associated with oral THC, we have embarked on the development of other dosage forms. These include suppositories and transmucosal delivery systems for indications requiring systems use and eye drops for topical application in the treatment of glaucoma. Because of the poor bioavailability (or lack of) of THC from such preparations, prodrugs of THC were prepared for that purpose with successful results. These preparations will be discussed. Furthermore, more recently cannabidiol (CBD) has emerged as an important cannabinoid for the treatment of a variety of disease conditions, most notably for intractable pediatric epilepsy. Efforts in that area will also be discussed.
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PL-14 CYTOTOXIC ACTIVITY OF BIOLOGICAL ACTIVITY SUBSTANCES Azimova Sh.S, Teomashko N.N, Khashimova Z.S., Terenteva E.O.
Institute of Chemistry of Plant Substances of AS RUz, Tashkent, Uzbekistan
Introduction At the Institute of Chemistry of Plant Substances of the Academy of Sciences of Uzbekistan for many years, a systematic study of the various classes of plant substances (BAS) and the study of their biological activity have been carried out. The Laboratory of Molecular Genetics screened alkaloids and their derivatives, glycosides, flavonoids and phytoecdysteroids and plants and fungi extracts for the cytotoxic activity. Materials and Methods Cytotoxic activity of the extracts and individual substances were measured by using verified cultures of cancer cells - carcinoma of the cervix (HeLa), larynx (HEp-2) and breast (HBL-100) obtained from the Bank of cell cultures at the Institute of Cytology RAS (Saint-Petersburg, Russia), and primary culture of hepatocytes and fibroblasts, by using of MTT and neutral red assay. Results and Discussion From the extracts of endophytic fungi associated with Vinca plants cytotoxic activity practically the same activity of the extract of Vinca rosea was observed. Moreover, extracts of plants of Convolvulus krauseanus, Arundo donax and Vinca major also revealed cytotoxic activity at low concentration. Among the individual substances – derivatives of 1-aryltetrahydroisoquinolines, convolvines, norfluorokurarine, phenyl- and phenoxy acetic acids identified three inhibitors only of cancer cells HEp-2 with low cytotoxicity to normal cells - N-benzyl konvolvin (IC50 = 12,3 mmol / l), n-Cl-phenoxyacetic acid (IC50 = 5,2 mM / L ) and phenylhydrazine yodmetilat norfluorocurarine (IC50 = 19,1 mmol / l). At the same time other substances such phenylhydrazine hydrochloride norfluorocurarine (IC50 = 24 mM / l) and n-Cl-acetylfenyl uksusnaya acid (IC50 = 4,7 mM / l) had cytotoxic activity to all investigated cancer cells and practically have no cytotoxic activity to normal cells. Investigation of the cytotoxic activity of plants and fungi extracts and chemical derivations of alkaloids and synthetic substances allowed us to select active compounds for further investigations.
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PL-15 Essential Oils As Natural Mosquito Agents Nurhayat Tabanca1,4*, Betul Demirci2, Ulrich R. Bernier3, Jeffrey R. Bloomquist4, Abbas Ali1, Eugene K. Blythe5, Temel Ozek2, Ikhlas A. Khan1, K. Husnu Can Baser2
National Center for Natural Products Research, The University of Mississippi, University, MS 38677 USA Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470, Eskisehir, Turkey 3 USDA-ARS, Center for Medical, Agricultural and Veterinary Entomology, Gainesville, FL 32608 USA 4 Department of Entomology and Nematology, Emerging Pathogens Institute, University of Florida, Gainesville, FL 32610 USA 5 Coastal Research and Extension Center, Mississippi State University, South Mississippi Branch Experiment Station, Poplarville, MS 39470 USA *
[email protected] 1 2
Introduction Aedes aegypti (L.) (Diptera: Culicidae) transmits viral pathogens to humans, including yellow fever and dengue fever, both of which can cause severe human morbidity and mortality. Vaccines are not available for many diseases transmitted by biting insects, so personal protection and control of the larval and/or adult stages are primary tools to reduce humanvector contact. However, the repeated use of synthetic insecticides can induce resistance concern and undesirable effects on human and non-target organisms (1). Therefore, there is an urgent need for the development of alternative insecticides and repellents to manage populations and protection of human being from the bites of these important disease vectors. Plant-derived products including essential oils may offer alternative and effective sources of insecticides and insect repellents. Materials and Methods In this research program aimed at identifying natural repellents and insecticides, different essential oils have been evaluated as topical repellents against Aedes aegypti using a “cloth patch assay” and larvicidal activity against 1st instar Ae. aegypti larvae. Results and Discussion Based on the screening results, five Agastache cultivars showed promising repellent or larvicidal activity and bioassay guided isolation procedures were followed. The comparable study on the chemical composition of German, Roman chamomile and Juhua essential oils were completed by GC-FID and GC-MS analysis. The chemical differences of these chamomile essential oils exhibited a variable degree of repellent activity in cloth patch assays. Consequently, essential oils encouraged the investigation as a natural repellent for medical and veterinary importance arthropods and could also lead to a new molecular based approach to l investigation of essential oils for pest control. Acknowledgements This study was supported in part by DWFP grant funded by the U.S. DoD through the AFPM and grant from the Mississippi Agricultural and Forestry Experiment Station. Reference 1. Tabanca, N., Bernier, U.R., Ali, A., Wang, M., Demirci, B., Blythe, E.K., Khan, S.K., Baser, K.H.C., Khan, I.A. 2013. BioassayGuided Investigation of Two Monarda Essential Oils as Repellents of Yellow Fever Mosquito Aedes aegypti. Journal of Agricultural and Food Chemistry, 61:8573-8580.
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PL-16 New Quality Monographs on Traditional Chinese Medicine (TCM) Herbal Drugs for the European Pharmacopoeia Gerhard Franz
Chairman of the TCM - Working Party of the European Pharmacopoeia University of Regensburg, Department of Pharmacy D-93040 Regensburg/Germany
[email protected]
Monographs on herbal drug materials including those of Chinese Materia Medica (CMM) have been subject to considerable improvement in recent years. Due to the actual rapid development in Science in general and in many fields of Pharmacognosy in special, important improvement of analytical methods is obvious and urgently needed to implement high quality standards for all herbals in the actual European Pharmacopoeia (PhEur) Monographs. Priority should be given to unambiguous definitions and identification of the TCM herbal drug material by macroscopic and microscopic examinations followed by chromatographic techniques such as high performance thin layer chromatography (HPTLC) fingerprinting. A key feature, in the elaboration of any new TCM herbal drug monograph is, the availability of a statistically relevant number of samples to be critically examined. In many cases it has been difficult in the past to obtain such a large variety of samples mostly from the European Market. It may be questioned that those samples commercially available in Europe have been specially prepared for the Western market and may be of different quality compared to CMMs used in China. It further is difficult to obtain authenticated reference samples for the botanically identified herbal drugs of Chinese origin. Consequently, a continuous cooperation with specialists of the ChPh is essential in that they can assist in the provision of authenticated herbal drugs and reference samples and in the elaboration of new TCM-monographs for the PhEur. Besides the unambiguous identification of the herbal drug material, the quantification of marker substances in herbal drugs in general and often in TCM is still a major problem and not easy to be resolved. For many CMM still no constituents with known therapeutic activity are documented in the relevant literature. In these cases plant specific natural substances have to be selected as the so-called analytical markers which have to be quantified accordingly. It can be questioned, if such assays for analytical markers, newly included in a monograph, which often are rather expensive, may thus be the reason for the low degree of acceptance in pharmaceutical practice and consequently are not used much by the European shareholders. Alternatives have to be elaborated and validated such as semi-quantitative HPTLC methods which in some cases might replace the classical HPLC assay. Consequently, one of the future goals for the TCM WP of the European Pharmacopoeia is the elaboration of a policy paper where the criteria for the elaboration and implementation of an assay should be determined. For the moment, it is still a case by case decision,, if an assay and which type of assay has to be included in a new TCM herbal drug monograph of the PhEur.
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PL-17 SYNTHESIS AND MODIFICATIONS OF THE DEOXYVASICINONE AND MACKINAZOLINONE DERIVATIVES B. Zh. Elmuradov,*1 A. O. Nasrullayev1
Institute of the Chemistry of Plant Substances, Academy of Sciences, Republic of Uzbekistan, 100170, Tashkent, Mirzo-Ulugbek str., 77.
[email protected]
1
Introduction Chemical modification of tricyclic quinazoline alkaloids and their derivatives may open very interesting direction in the field of fundamental science as well as for development efficient preparations for agriculture and medicine. During 3540 years at the Institute of the Chemistry of Plant Substances (ICPS) chemistry and biological activity of the quinazoline alkaloids are studied and among of them many biological active compounds are found. For example, deoxypeganine hydrochloride (R=R1=R3=R4=H, X=H2, n=1) is used in medicine as anticholinesterase preparation (Johns et al., 1965; Shakhidoyatov, 1988). There are some reactive centers: activated methylene group, C=N bond, carbonyl C=O group and benzene ring in molecules of deoxyvasicinone and mackinazolinone, which were isolated from plants Peganum harmala L. and Mackinlaya subulata Philipson (Johns et al., 1965; Shakhidoyatov et al., 2014). These centers can react with different electrophilic and nucleophilic reagents to give new derivatives with various activities. Materials and Methods 6Н (Substituted)-, 6,8-disubstituted-deoxyvasicinones, mackinazolinones, 4-thiones, α-yliden derivatives, fine organic synthesis, methods of IR-, NMR1H- spectroscopy, mass-spectrometry, X-ray analysis, thin-layer chromatography. Results and Discussion Interaction of deoxyvasicinone, mackinazolinone and their derivatives with various electrophilic reagents (aliphatic and aromatic aldehydes and ketones, acid chlorides, formylating agents and etc.) have been studied. It was determined that depending on substituents in benzene ring and quantity of methylene group reaction goes in different directions: X R
N N R1
( )n R3
R4
R: R1: R2: R3,R4: R3+R4: R5: X: n:
H, Br, NO2, NH2, NHCOR2 H, Br, NO2, NH2 Me, Et, Pr H, Br =CH-R5 OH, Cl, NH2, SeH H2, O, S 1,2
In this work the obtained results on synthesis, modification and biological activity of tricyclic quinazoline alkaloids and their derivatives, and factors influencing to reactions direction will be discussed. Acknowledgments We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (Projects FA-F7-T207 and FA-A9-T200). References 1. Johns, S. R., Lamberton, J. A., 1965. Alkaloids of Mackinlaya Species (Family Araliaceae), Chemical Communication, 267270. 2. Shakhidoyatov, Kh. M., 1988. Quinazol-4-ones and their biological activity, FAN, Tashkent, pp 99-104. 3. Shakhidoyatov, Kh. M., Elmuradov, B. Zh., 2014. Tricyclic quinazoline alkaloids: isolation, synthesis, chemical modification and biological activity. Chemistry of Natural Compounds, 50: 781-800.
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oral presentatıons
OP-01 ESSENTIAL OILS OF plantS OF CENTRAL ASIA S.V. Zhigzhitzhapova*1,2, T.E.Randalova2, L.D. Radnaeva1,2
1 Baikal institute of Nature Management Siberian Branch Russian Academy of Sciences, Ulan-Ude 670047 Republic of Buryatia, Russian Federation 2 Buryat State University, Ulan-Ude, Republic of Buryatia, Russian Federation corresponding author
[email protected]
Introduction The territory of Buryatia represents a classic variant of the buffer territory and is located at intersection of ecosystems of North and Central Asia. There are 2128 species and subspecies of the 127 plant families at a rather small territory. Plants of the genus Thymus L. and Artemisia L. have interested researchers as promising sources of herbal medicinal products. The Baikal region is one of the centers of origin of Artemisia in Euroasia (Namzalov, 1994). Materials and Methods The essential oils were isolated by hydrodistillation from air-dried raw materials. Chemical composition of essential oils were analyzed by GC-MS. Essential oil constituents were identified by the comparison of their mass spectra with those from the National Institute of Standards and Technology (NIST, 2007), and by the comparison of the mass spectra and calculated linear retention indices (RI) with values in the literature (Tkachev, 2008). Retention indices were obtained by co-injection with a mixture of linear hydrocarbons C8–C20 (Sigma, USA) according to the work (Tkachev, 2008). Relative percentage amounts of individual components of the oil were expressed as a percent peak area relatively to the total peak area from the GС-MS analyses of the oils. The data related to composition of essential oil was subjected to multivariate statistics using principal component analysis (PCA) which is available in the Sirius 6.0 package (Kvalheim and Karstang, 1987). Results and Discussion Essential oils of Thymus baicalensis Serg. are phenolic chemotype, namely carvacrol chemotype. Essential oils of Artemisia jacutica contains a large amount of chamazulene. Oils of both species may find application as a source of new medicines and dietary supplements, has antiseptic, anti-inflammatory and antimicrobial properties. Comparison of own and literature data shows that the direction of the biosynthesis of essential oil components persist regardless of the locus of the year and collecting plants. Principal component analysis (PCA) identified three chemotypes of compounds of essentials oils of Artemisia vulgaris L.: chemotype I – essential oil of plant from humid areas; chemotype II – essential oil of plant from semihumid areas; chemotype III – essential oil of plant from semiarid and arids areas. In arid areas there is an increase of the total content and the structural diversity of sesquiterpene compounds. On arid areas, for example plants of Buryatia have shown that, in ecotope with more affluent moisture, plants accumulate the greatest amount of sesquiterpenes. Lack of moisture helps to increase the share of monoterpenes and their oxygenated derivatives in the summer. Components of essential oils are very interesting for the synthetic and theoretical chemistry because of their high reactivity and availability as synthons in the preparation of practically useful compounds. Components of essential oils have allelopathic activity, so research will shed light on some questions of interaction in phytocenoses and the role of secondary metabolism in plant adaptation. Acknowledgments This research was supported by the Ministry of education and science of the Russian Federation (State task № 19.1168.2014/К), programs of basic scientific researches of State academies of sciences (project V.46.5.2) and Russian Foundation for Basic Research (grant № 15-44-042330). We thank Elena Dylenova, assistant of pharmacy department (Buryat State University) for language editing work of this manuscript.
References 1. Namzalov, B.B. 1994. The steppes of southern Siberia [in Russian]. BSC SB RAS, Novosibirk, Ulan-Ude. pp1-309. 2. Tkachev, A.V. 2008. Investigation of plant volatiles [in Russian]. Novosibirsk. pp1-969. 3. Kvalheim, O. M., Karstang, T. V., 1987. A general purpose program for multivariate data analysis. Chemometrics and Intelligent Laboratory Systems. 2, 235-237.
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OP-02 Chemıcal composıtıon of essentıal oıls from savory under dıfferent extractıon methods: Conventıonal dıstıllatıon, an ınnovatıve technıque steam dıstıllatıon, mıcrowave-assısted steam hydro-dıffusıon, and mıcrowave-assısted hydro-dıffusıon methods Abdollah Ghasemi Pirbalouti1*, Sayadeh Mansoreh Memarzadeh 2 , Behzad Hamedi1
Shahrekord Branch, Islamic Azad University, Research Center for Medicinal Plants & Ethno–veterinary, Department of Medicinal Plants, P O Box: 166, Shahrekord, Iran 2 Flavarjan Branch, Islamic Azad University, Department of Essential oil Chemistry, Isfahan, Iran
[email protected] 1
Introduction Satureja bachtiarica Bunge. (Lamiaceae; local name: “Marzeh-e-Koohi”) is a well-known aromatic plant which is frequently used as spice and as traditional medicinal herb in Iran. Bakhtiari savory is a perennial aromatic herb, which it distributed in Zagros mountain range, southwestern Iran (Ghasemi-Pirbalouti et al., 2013a). The conventional methods for the essential oil extraction of herb materials, including hydrodistillation and steam distillation have some disadvantages. Losses of some volatile compounds, low extraction efficiency, degradation of unsaturated or ester compounds through thermal or hydrolytic effects and toxic solvent residue in the extract may be encountered using these extraction methods (Périno-Issartier et al., 2013). In this study, we present a comparative study of the ability of a number of different methods to extract the essential oils from Bakhtiari savory in order to find the most advantageous in term of extraction kinetics, essential oil quality, and quantity. Materials and Methods Conventional methods [hydrodistillation by two Clevenger-type apparatus: British Pharmacopoeia (HDBP) and Research Institute of Forests and Rangelands, Iran (HDRIFR), and traditional steam and water distillation (TSWD)], an innovative technique steam distillation (SDinnov), microwave-assisted steam hydro-diffusion (MSHD 400 and 800 W), and microwave-assisted hydro-diffusion (MHD 400 and 800 W) were used to extract essential oil from the aerial parts of savory and their results were compared. The essential oils of all samples were analyzed using GC-FID, GC/MS, and for comparison, a sample was analyzed using head space solid-phase microextraction (HS-SPME). Results and Discussion The highest essential oil yields were obtained from two methods, including HDBP, and MSHD 400 W. Significant differences occurred among the major constituents in essential oils from extraction methods, including thymol, carvacrol, ρ-cymene, and γ-terpinene. The highest amounts of thymol and carvacrol were obtained from MHD (800 W) method in comparison other methods. The highest content of monoterpene hydrocarbons was obtained from HS-SPME, whereas the highest percentage of oxygenated monoterpenes was achieved from MHD (800 W) method. In conclusion, extraction of the essential oil from Bakhtiari savory with microwave-assisted hydro-diffusion (MHD) was better in terms of energy saving, extraction time, oxygenated fraction (thymol and carvacrol), and product quality. References 1. Ghasemi Pirbalouti, A., Oraie, M., Pouriamehrc, M., Solaymani Babadi, E. 2013. Effects of drying methods on qualitative and quantitative of the essential oil of Bakhtiari savory (Satureja bachtiarica Bunge.). Industrial Crops & Products, 46: 324–327. 2. Périno-Issartier, S., Ginies, C., Cravotto, G., Chemat, F. 2013. A comparison of essential oils obtained from lavandin via different extraction processes: ultrasound, microwave, turbo hydrodistillation, steam and hydrodistillation. Journal of Chromatography A, 1305: 41-47.
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OP-03 Chemical composition and biological activity of essential oil of Chaerophyllum aromaticum L. from Turkey Mine Kürkçüoğlu1, Ali Şen2*, Leyla Bitiş2, Seher Birteksoz Tan3, Ahmet Doğan4, Kemal Hüsnü Can Başer1,5
Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, Eskişehir, Turkey. 2Marmara University, Faculty of Pharmacy, Department of Pharmacognosy, İstanbul, Turkey. 3Istanbul University, Faculty of Pharmacy, Department of Pharmaceutical Microbiology, Istanbul Turkey. 4Marmara University, Faculty of Pharmacy, Department of Pharmacetical Botany, Istanbul, Turkey. 5King Saud University, College of Science, Department of Botany and Microbiology, Riyadh, Saudi Arabia. *
[email protected] 1
Introduction The purpose of this study was to investigate chemical composition along with antimicrobial, antioxidant activity of essential oil of Chaerophyllum aromaticum L. The oil was analyzed by capillary GC and GC/MS using a Agilent GCMSD system. Antioxidant activitiy and total phenolic content were estimated by DPPH and Folin Ciocalteu methods, respectively. Antimicrobial activity against eight microbial species were determined by the microbroth dilution technique using the Clinical Laboratory Standards Institute (CLSI) recommendations. The yield of light yellow-coloured essential oil obtained from aerial parts of C. aromaticum is about 1.1% and Sabinene (28.1%), Terpinolene (16.7%) and γ-Terpinene (16.1%) were found as the main compounds in the oil. C.aromaticum essential oil at a concentration of 20 mg/ml inhibited DPPH radical by 2,06%. Its total phenolic content was 2,19±0,18 mg GAE / g oil. Oil presented moderate antimicrobial activity against Staphylococcus aureus ATCC 29213 (MIC: 156 µg/ml) and Staphylococcus epidermidis ATCC 12228 (MIC: 625 µg/ml). Materials and Methods Chaerophyllum aromaticum was collected from around Riva Çayağız brook of Istanbul in 2014. Voucher specimens are kept at the Herbarium of the Faculty of Pharmacy, Marmara University (MARE No: 17271). Aerial parts of Chaerophyllum aromaticum were water-distilled for 3h using Clevenger apparatus. The essential oils were stored at 4°C in the dark until analyzed. The oil was analyzed by capillary GC and GC/MS using a Agilent GC-MSD system. Free radical scavenging capacity of oil was evaluated according to the previously reported procedure using the stable DPPH (Ozsoy et al., 2008). Total phenolic content of oil was measured using Folin–Ciocalteau reagent (Gao et al., 2000). Antimicrobial activity against eight microorganisms were determined by the microbroth dilutions technique using the Clinical Laboratory Standards Institute (CLSI) recommendations. Results and Discussion In our present study, we examined chemical composition along with antimicrobial, antioxidant activity of essential oil obtained from aerial parts of C.aromaticum. Nineteen compounds were identified in oil of the aerial parts representing 99.2 % of the C. aromaticum oil. The main components of the C. aromaticum oil were sabinene (28.1%), terpinolene (16.7%) and γ-terpinene (16.1%). While essential oil of C. aromaticum at concentration of 20 mg/ml inhibited DPPH radical by 2,06 % ; BHT, synthetic antioxidant, inhibited DPPH radical by 83 % at ten times lower concentration (2 mg/ml; IC50 for BHT: 0,84±0,02 mg/ml ). The total phenolic content of essential oil was found to be low (2,19±0,18 mg GAE / g oil). The oil exhibited moderate activity against Staphylococcus aureus ATCC 29213 (MIC: 156 µg/ml) and Staphylococcus epidermidis ATCC 12228 (MIC: 625 µg/ml). The oil did not show any activity against other microorganisms. References 1. Gao, X., Ohlander, M., Jeppsson, N., Björk, L., Trajkovski, V. 2000. Changes in Antioxidant Effects and Their Relationship to Phytonutrients in Fruits of Sea Buckthorn (Hippophae rhamnoides L.) during Maturation. Journal of Agricultural and Food Chemistry ,48: 1485-90. 2. Ozsoy, N., Can, A., Yanardag, R., Akev, N. 2008. Antioxidant activity of Smilax excelsa L. leaf extracts. Food Chemistry, 110: 571-83.
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OP-04 Lipids and Essential Oils of Arischrada bucharica (M.Pop.) Pobed. and Ziziphora pedicellata Pazij et Vved. Leaves D.T. Asilbekova1,*, Kh.M. Bobakulov1, Gulmira Özek2, Temel Özek2, N.D. Abdullaev1, Sh.Sh.Sagdullaev1, K. Husnu Can Başer2,3
Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of 100170 Tashkent, Uzbekistan, 2 Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470 Eskisehir, Turkey 3 Botany and Microbiology Department, College of Science, King Saud University, 11451, Riyadh, Saudi Arabia
[email protected] 1
The lipids and essential oils isolated from leaves of Arischrada bucharica (M.Pop.) Pobed. and Ziziphora pedicellata Pazij et Vved. (Lamiaceae), growing in Uzbekistan have been studied. Total lipids (TL) from plant materials were isolated with chloroform - methanol (2:1, v/v) by Folch method, purified and fractionized on neutral lipids (NL), glycolipids (GL) and phospholipids (PhL). Essential oils (EO) of plants were obtained by hydrodistillation in a Clevenger type apparatus. Unsaponifiable substances (US) and fatty acids were obtained after hydrolysis of TL (10% KOH/MeOH, 1-2 hr). Fatty acids were converted to methyl esters using diazomethane. All the volatiles and fatty acid methyl esters were analyzed by GC/FID and GC/MS techniques. Yields of the lipids and essential oils from both species are given in the Table. The present work is the first detailed contribution into the chemistry of lipids A. bucharica leaves.
Table. Yields of essential oils and lipids from A. bucharica and Z. pedicellata leaves EO TL NL GL PhL US % dry wt of leaves % mass of total lipids A. bucharica 0.8 1.8 63.7 32.8 3.5 14.4 Z. pedicellata 1.4 3.8 47.2 48.0 4.8 15.9 The essential oil of A. bucharica leaves consisted of 1,8-cineole (19.1%), α-humulene (9.6%), β-caryophyllene (8.4%), β-bourbonene (5.4%), δ-cadinene (4.1%), δ-terpineol (3.6%), camphor (3.3%), bicyclogermacrene (3.1%) as main constituents. Pulegone (60.4%), isomenthone (15.6%), p-menth-3-en-8-ol (7.9%) and isomenthol (4.5%) were found to be the main components in essential oil from Z. pedicellata leaves. In previously reported papers by Gusakova et al. and Dembitskii et al. [1,2] the oil of Z. pedicellata was said to be rich in pulegone (62.0%), isomenthone (11.5%) and menthol (9.2%). However, in this study menthol was found in trace amount. In previous studies, p-menth-3-en-8-ol was not reported in the oil. Plant material
Fatty acid compositions of TL from A. bucharica and Z. pedicellata leaves were following: 12:0 – trace and 0.4%; 14:0 – 1.0% and 1.9%; 15:0 – trace and 0.4%; 16:0 – 19.7% and 19.4%; 17:0 – trace and 0.5%; 18:0 – 3.9% and 3.8%; 20:0 – 1.3% and 1.6%; 22:0 – 0.7% and 1.3%; 16:1 – 1.2% and 1.1%; 18:2 – 5.3% and 17.6%; 18:3 (main)+18:1 – 67.2% and 52.0%. references 1. Gusakova, S.D., Khomova, T.V., Lipids of Ziziphora pedicellata, Chem. Nat.Comp., 33, 633 (1997). 2. Dembitskii, A.D., Bergaliev, E.Sh., Kyazimov, I.M., Chemical composition of the essential oils of Ziziphora growing under various ecological conditions, Chem. Nat.Comp., 30(6), 673-675 (1994).
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OP-05 DEVELOPMENT OF THE TECHNOLOGY OF KROSTOPIDIN PREPARATION PRODUCTION FROM THE AERIAL PART OF CAPPARIS SPINOSA PLANT A.Z. Sadikov, Sh.Sh. Sagdullaev, R.A. Botirov, V.N. Ahmedov, D.K. Mutalova, M.E. Tursunov S. Yu. Yunusov Institute of the Chemistry of Plant Substances,Tashkent, Uzbekistan Academy of Sciences Republic of Uzbekistan
[email protected]
Introduction Capparis spinosa is a medicinal plant widespread in the territory of the Central Asia. This plant can be collected by hundreds of tons per year without damage to the natural resources. At present, the fruits of this plant as a foodstuff have been consumed by the local population in many countries. Materials and Methods As reported in literature, Capparis spinosa aerial part contains more than 2% of alkaloids. Stachydrine, choline and a few unidentified alkaloids were founded in its chemical composition, stachydrine alkaloid is the main alkaloid, its’ content is approximately 50% of the total alkaloids. Researches carried out in the Pharmacology and Toxicology Department of our Institute led to development of the preparation Krostopidin with haemostatic, hypotensive, sedative and anti-inflammatory properties on the base of stachydrine alkaloid. Results and Discussion In order to develop the technology of Krostopidin preparation based on stachydrine alkaloid the physical and chemical properties of stachydrine were investigated. It was found that the alkaloid is a very soluble in water, but not in organic solvents, so aqueous of alcohol was selected as extragent. The technology of Krostopidin manufacture using of ethanol solution as an extragent was developed. This technology was used for providing of sufficient amounts of the preparation for preclinical pharmacological and toxicological researches and for the development of regulatory and technical documents for clinical trials. The quality and quantity of the preparation was tested by thin layer chromatography, chromato-spectro-photometry and other instrumental methods.
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OP-06 Heavy Metal Contamination of Soil and Plants In The Vicinity of Blacksmith Workshop in Kazaure Town, Nigeria Idris Aminu*, Muhammad Salis Suleiman and Kamaluddeen Muhammad Bayero University, Kano, Nigeria. e-mail address:
[email protected]
Introduction Plants growing on metal contaminated soils accumulate some heavy metals at high levels (Xiong, 1998). These plants are considered to be phytoaccumulators and may contribute serious health hazards if they are consumed, because of the toxicity of some of the metals to human being and animals (Knasmuller et al; 1998; Micita and Murin, 1998). In this work, the concentrations of heavy metals (Fe, Cr, Zn, Ni, Pb and Cd) were determined for two different plant species (Cassia tora and Cassia occidentalis) which grow as shrubs in the vicinity of blacksmith workshop but used by local people as medicine. Experiment was also conducted on samples of the same plants in an area free of blacksmith activities. Soil samples in the vicinity of the blacksmith workshop were also tested for heavy metals to know the bioaccumulation of these elements in the plants. Material and Methods Dry ashing procedure was used for the digestion of the samples. All the prepared solutions (blank, standard and sample) were analyzed using the atomic absorption spectrophotometer (model: VGP 210) for measuring the metals concentrations. Results and Discussion Table 1: Concentration of Heavy Metals in the Sampling Areas
Metals Zn Pb Fe Cr Ni Cd
Sampling Area A C. Tora C. Occidentalis Conc. (mg/kg) Conc. (mg/kg) 20.83 22.92 9.09 13.64 12.96 11.11 10.87 15.22 25 17.86 10.53 18.42
Sampling Area B C. Tora C. Occidentalis Conc. (mg/kg) Conc. (mg/kg) 18.75 18.75 11.36 11.36 16.67 14.81 13.04 13.04 17.86 21.43 15.79 13.16
The heavy metal concentrations (mg/kg) of the studied plants ranged from 11.11 to 14.81 for Fe, 13.04 to 15.22 for Cr, 18.75 to 22.92 for Zn, 17.86 to 25.00 for Ni, 9.09 to 13.64 for Pb and 10.53 to 18.42 for Cd. Generally, the levels of Cr, Ni, Pb and Cd present in the leaves of Cassia occidentalis were found to be significantly higher than the permissible limits given by the FAO and WHO. In Cassia tora, the concentrations of Cr, Ni and Cd were above the WHO’s permissible limit. Concentrations of all the metals were lower in plants samples from an area unaffected by the blacksmith activities. For both plant samples, concentration of the metals were found to be higher when compared with concentration of the metals in the respective soil except for iron and zinc which were observed to be higher in the soil sample than in plant leaf for both C. tora and C. occidentalis plants. References 1. Knasmuller, B.J. 1998. Ecophysiology of metal uptake by tolerant plants; in: Heavy Metals Tolerance in Plants Evolutionary Aspects (Ed.: A.J. Shaw). CRC, Press Boca Raton, FL pp.155-178. 2. Micita, J. Murin, B.K. 1998. Heavy metals in green vegetables and soil from Vegetable gardens in Dar-es Salaam, Tanzania. Tanzania Journal of Science 27:37-48. 3. Xion, C.K. Chen, T.B. and Wong J.W.C 1998. Assessment of trace metal distribution and contamination in surface soil of Hong Kong. 98 (1): 61-68.
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OP-07 PERSPECTIVES OF THE DEVELOPMENT OF LOCAL HEPATOPROTECTORS BASED ON PHYTOCOMPOSITION WITH PHOSPHOLIPIDS Tursunova N.V.*, Syrov V.N., Gusakova S.D., Sagdullaev Sh.Sh., Hushbaktova Z.A.
Acad. S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Uzbekistan
[email protected]
Introduction The preparations containing phospholipids on the base of plant lecithin (phosphatidylcholine) are widely used for the treatment of the hepatobiliary system diseases. Now a day the therapeutic efficiency of phospholipids is enhanced by the addition of amino acid, macroergic substances, antioxidants, minerals and other metabolic compounds. Carotenoids, which have important functions in the body, are promising as such additives. Acyclic carotenoid lycopene is the strongest plant lipophilic antioxidant [Nguyen M.L., Schwartz S.L. 1999]. Therefore, we have developed a compositions based on soy lecithin and an extract from tomato peel with high content of carotenoids, especially lycopene. We made an experimental assessment of hepatoprotective properties of different variants of the new composition on hepatitis and stress models. Materials and methods For the preparation of these compositions commercial food soy lecithin was purified till reaching of pharmaceutical quality, sunflower oil and carotenoid extract of peel tomato fruits of the local species were added. Several compositions of lecithin and carotenoid extract with different contents of lycopene were obtained. The compositions were administered per os to laboratory animals (mice of 20-25 g and rats of 200-220 g) once and several times in preventive and therapeutical medical mode against the background of paracetamol, heliotrine and in the case of acute stress reaction obtained by hanging by neck fold. The main indexes of basal metabolism were determined after development of mentioned pathologies. Results and discussion Experiments have shown that the compositions with lycopene content 36-50 mg% (extract) were most effective. A single administration of these compositions in different doses (2.5 to 5 μg/kg of lycopene) led to reduction of all manifestations of stress response and normalized hepatic metabolism: kept glycogen, reduced severity of lipid peroxidation, cytolysis and cholestasis, restored cholesterol and creatine phosphate. It was founded the expressed hepatoprotective action of these compositions at a dose of lycopene of 5 μg/kg after 5-7 days of administration in terms of established hepatitis: intensification of protein synthesis and antioxidant protection of cells, optimization of lipid and carbohydrate metabolism, as well as the recovery of the biliary excretion. In these tests hepatoprotective effect of compositions was more pronounced than the one in the animals treated with the phosphogliv and karsil as reference drugs. Thus, the obtained result showed that the development of a new local hepatoprotective phytocomplex on the basis of phospholipids and lipophilic antioxidants is promising. Reference 1. Nguyen M.L., Schwartz S.L. 1999. Lycopene: chemical and biological properties. Food Technology, 53: 38-45
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OP-08 Toxicity Analysis of Polychlorinated Dibenzofurans Using Global and Local Aromaticity Indices Ablikim Kerim
School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China
[email protected]
Introduction As is well known, dioxin is a highly toxic compound and also a main source of pollution in atmosphere. Depending upon the number and position(s) of chlorine-substitution(s), polychlorinated dibenzofurans (PCDFs) have 25 possible structures[1]. Their chemical structure and atomic numbering scheme are shown in Fig. 1. The half maximal inhibitory concentration (IC50) is a measure of the effectiveness of a substance in inhibiting a specific biological or biochemical function. In the present work, the global aromaticity of 25 kinds of PCDF isomers were examined using the TRE (topological resonance energy) and the MRE (magnetic resonance energy) methods[2,3]. Their local aromaticity was studied using the BRE (bond resonance energy) and the CRE (circuit resonance energy) methods[2,3].The effect of the number and positions of substituted chlorine atoms on the global and local aromaticities of PCDFs is discussed. Our TRE and MRE results show that the global aromaticity of PCDFs decreases with an increase in the degree of chlorination. BRE and CRE results show that within the same molecule, those six-membered rings into which chlorine atoms have been substituted show lower local aromaticity compared with six-membered rings into which no chlorine atoms have been substituted. Finally, the relationships between aromaticity indices and some biological activity (IC50) were examined. We have found that the experimental biological activities (pIC50) of PCDFs are well correlated with their aromaticity indices. We believe that the aromaticity indices in this work can serve as useful theoretical tools with which to study the toxicity of dioxin-like compounds.
X14
X15
X 21
11 12
X16
10
1
7 9
8
X17
13
O
X20
6 2
5 4 3
X19
X18
Fig.1. The structure of polychlorinated dibenzofurans and its atomic numbering scheme Acknowledgments This work was financially supported by the Natural Science Foundation of China (No. 21262037) . References 1. C.L. Waller, J.D. McKinney, Chem. Res., Toxicol. 1995, 8, 847-858. 2. J. Aihara, J. Am. Chem. Soc., 2006, 128(9), 2873-2879. 3. A.Kerim, New J. Chem., 2014, 38, 3783
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OP-09 Monoterpene esters of aromatic acids from the roots of Ferula calcarea I.G. Heydarov, S.V. Serkerov*
Institute of Botany of Azerbaijan NAS, Badamdar ave. 40, Baku AZ1073, Azerbaijan
[email protected]
Members of the genus Ferula contain substances belonging to different groups of natural compounds. Some of them contain sesquiterpene lactones, which have anti-inflammatory, anti-burn, amnestic and other healing properties (Serkerov, 2005). Some of them (Ferula pangifolia, F. seratophylla, F. tschimganica, F. pallida etc.) contain terpenoid esters, terpenoid coumarins etc. (Khasanov et al., 1972; Kadyrov et al., 1972; Saidkhodjaev, 1979). Therefore, the study of the chemical composition of plants of this genus has particular interest. We researched the roots of Ferula calcarea, collected from mountain Beshbarmak during flowering. From the sum of extractives obtained by extracting crushed, dried roots of acetone, by column chromatography was isolated two substances: C17H22O3, m.p. 167-168⁰C (1), C18H24O4, m.p. 84-85⁰C (2). The 1H NMR spectrum of compound 1 appears signals: 0.80 (s., CH3–C–), 0.81 (s., CH3–C–), 0.92 (s., CH3–C–), 4.96 (d., J=9.19 Hz, HC–O–), 6.89 (d., J=7.85 Hz, 2CH=), 7.84 (d., J=7.85 Hz, 2CH=) and 10.31 ppm (s., HO–C=). The 1H NMR spectrum of the substance 2 detected signals: 0.79 (s., CH3–C–), 0.87 (s., CH3–C–), 0.96 (s., CH3–C–), 3.84 (s., CH3–O–), 4.96 (d., J=9.19 Hz, HC–O–), 6.89 (d., J=7.85 Hz, –CH=), 7.45 (c., CH=), 7.53 (d., J=7.85 Hz, CH=) and 9.92 ppm (s., HO–C=). Hydrolysis of compounds 1 and 2 with alkalis leads to e-borneol (C7H6O3, m.p. 204-205⁰C) and p-hydroxybenzoic acid (C7H6O3, m.p. 210-212⁰C), and e-borneol and vanillic acid (C8H8O4, m.p. 206-207⁰C), respectively. Based on the data obtained in the interpretation of the 13C NMR spectrum of the compound 1 (13.80; 19.13; 20.34; 27.37; 28.34; 37.06; 40.20; 45.05; 47.60; 49.17; 79.44; 115.77 (2C); 121.35; 132.00 (2C); 162.76; 165.91 ppm) and 13C (13.88; 19.02; 19.87; 27.38; 28.10; 36.95; 39.33; 36.60; 39.88; 40.16; 40.44; 44.78; 47.83; 49.05; 55.96; 79.49; 112.95; 115.60; 121.47; 123.67; 147.83; 151.97, 166.10 ppm), Dept 135 (13.88; 19.02; 19.02; 19.87; 27.38; 28.10; 36.95; 44.78; 55.96; 79.49; 112.95; 115.60; 123.47 ppm) and Dept 90 (44.78; 79.49; 112.95; 115.60; 123.67 ppm) spectra of compound 2 along with 1H NMR spectra proved that the compound 1 and 2 have structures identical to L-chimgin and L-chimganin, respectively. H CH
3
H
O
H
CH
C
H C
OH
C
H
3
H
3
H
H H
H
H
O
H
R
1. R= H 2. R= OCH
3
\s
References
1. Saidkhodjaev, A.I. 1979. Sesquiterpene derivatives of Ferula genus. Chem. Nat. Comp., 437-466 (in Russian). 2. Serkerov, S.V. 2005. Terpenoids and phenolic derivatives of plants of the families Asteraceae and Apiaceae. CBS polygraphic production, Baku, pp. 1-312 (in Russian). 3. Hasanov, T.H., Saidkhodjaev, A.I., Nikonov, G.K. 1972. The components of roots of the Ferula pallida. Chem. Nat. Comp., 807-808 (in Russian). 4. Kadyrov, A.S., Khasanov, T.H., Saidkhodjaev, A.I., Nikonov, G.K. 1972. New phenolic compounds of roots of the Ferula tschimganica. Chem. Nat. Comp., 808-809 (in Russian). SCNC 2015 Abstracts
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OP-10 New coumarin derivatives with isopropyl group at C-8 of Peucedanum ruthenicum Bieb. S.V. Serkerov * 1, G.K. Kasumova2
Institute of Botany of Azerbaijan National Academy of Sciences, Badamdar ave. 40, Baku AZ1073, Azerbaijan, Ganja State University, H.Aliyev str. 187, AZ2000 Ganja, Azerbaijan
[email protected] 1 2
Members of the genus Peucedanum L. (Apiaceae) contain a biologically active coumarin-derivatives belonging to different groups of coumarin compounds (Abyshev et al., 2003). Basically they are found as furocoumarin derivatives - peucedanin (P. officinalis L., P. morissoni Bess., P. tauricum M.B., P. ruthenicum M.B.), oroselol (P. oroselinum (L.) Moench.) and dihydrofurocoumarin derivatives - nodakenetin (P. decursivum Maxim.), marmesin (P. terebinthaeum Fisch.), columbianidin oxide, isopeulustrin (P. palustre (L.) Moench.) (Kuznetsov, 1967). Some species (P. praeruptorum Dunn.) contains pyranocoumarins: ±praeruptorin A and ±praeruptorin B having a specific activity against human gastric cancer (Liang et al., 2010; Gao et al., 2004; Song et al., 2015). From the roots of resin of the P. ruthenicum M.B. except furocoumarin peucedanin having antitumor activity (Serkerov and Gasumova, 2013) is isolated two new coumarin-derivatives called us as peuceruten (C14H16O4, m.p. 138.0-139.0⁰C (1)) and peucerutin (C16H14O6, m.p. 145.0-146.0⁰C (2)). According to the data of 1H NMR spectrum molecule of peuceruten contains 2 methoxy- (s., 3.90 and 4.14 ppm) and isopropyl groups (d., 1.20, J=6.00 Hz, 2CH3– and 3.20 ppm., –CH–). Based on these data, along with the signals from the aromatic protons (d., 6.35, J=10.00 Hz, 3 H; 8.00, J=10.00 Hz, H-4; s., 7.55 ppm, H-5), and data of 13C NMR Dept 135, Dept 90 and COSY spectra to peuceruten is offered the structure (1). In the 1H NMR spectra of peucerutenin (2) revealed signals (CH3)2–CH– (s., 0.80, 1.00, m., 2.15 ppm), CH3O– (s., 4.00 ppm), 6.40 m .d. (d., J=10.00 Hz, H-3), 7.80 (s., 2 H), 8.00 (d., J=10.00 Hz, H-4), 8.10 (s., –COOH), which taking into account the data of 13C NMR spectra have allowed to establish a structure of peucerutenin as (2). Thus, based on the data obtained by decoding the IR-, NMR 1H, 13C, Dept 135 spectra to these compounds has been offered the structures (1) and (2), respectively: H
H
H 3 OC
OCH
HOOC
H
3
H
H
H 3 OC
O
O
O
O CH
CH H C 3
O
CH
3
(1)
H C 3
CH
3
(2)
References 1. Abyshev, A.Z., Agayev, E.M., Kerimov, Y.B. 2003. Chemistry and Pharmacology of Natural Coumarins. Baku, pp. 1-112. 2. Liang, T., Yue, W., Li, Q. 2010. Chemopreventive effects of Peucedanum praeoruptorum Dunn. and its major constituents on SGC7901 gastric cancer cells. Molecules, 15: 8060-8071. 3. Gao, Y-L., Wang, W-J., Rao, G-X., Sun, H-D. 2004. The chemical constituents of Ligusticum calophlebicum. Acta Botanica Yunnanica, 26 (2): 234-236. 4. Song, Y., Wanghui, J., Ru, Y., Yitao, W. 2015. Research progress of the studies on the roots of Peucedanum praeruptorum Dunn. (Peucedani radix). Pak. J. Pharm. Sci., 28 (1): 71-81. 5. Serkerov, S.V., Gasumova, G.К. Method of obtaining and anticancer compound. Patent No а2011 00 85, 05.06.2013.
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OP-11 The structure and the biological activity of Seseli campestre angular pyranocoumarins N.Kh. Mikailova, S.V. Serkerov*
Institute of Botany, Azerbaijan National Academy of Sciences, Badamdar ave. 40, Baku AZ1073, Azerbaijan,
[email protected]
The plants of the genus Seseli L. (Apiaceae) characterized by the presence of kellactone group pyranocoumarins. Among the acylated kellactone derivatives found in different parts of plants of this genus antispasmolytic activity of pterixin, expressed hypotensive, P-adrenoblocking and antiarrhythmic activity of campestrol, campestrinol et al. (Abyshev et al., 2003) has been established. Recent reports of T.Liang et al. (2010) on the specific activity of ±praeruptorin A and of ±praeruptorin B isolated from Peucedanum praeruptorum Dunn. against human gastric cancer cells also suggests prospects of study of pyranocoumarins of the Seseli genus plants. At the present study of acetone extract of the Seseli campestre Bess. roots by column chromatography are received four individual pyranocoumarins: C14H14O5, m.p. 190.5191.5⁰C (1), C19H20O6, m.p. 122.0-123.0⁰C (2), C19H20O6, colorless resin, C24H26O7, m.p. 176.0-177.0⁰C (4). Presence in 1Н NMR spectra the signals of 1.34 (s., 3Н, СН3–2’’), 1.40 (s., 3Н, СН3–2’), 5.30 (d., J=4.94 Hz, Н-3’), 5.60 (d., J=4.94 Hz, Н-4’) in compound 1; 1.80 (s., 3Н, СН3–С=), 1.85 (d., J=7.00 Hz, СН3–СН=), 6.10 (m., –СН=, Н-3’, 2Н), 5.10 ppm (d., J=6.43 Hz, Н-4’) и 1.50 ppm (s., 6Н, 2 СН3–2’) in compound 2; 1.85 (s., СН3–С=), 2.10 (s., СН3–С=), 4.70 (d., J=6.45 Hz, Н-3’), 5.70 (s.,–СН=), 6.05 (d., J=6.45 Hz, Н-4’), 1.35 (s., СН3–2’ и 1.40 ppm (s., СН3–2’) in compound 3; 1.75 (s., СН3–С=), 1.80 (s., СН3–С=), 1.85 (d., J=7.00 Hz, СН3–С=), 1.90 (d., J=7.00 Hz, СН3–СН=) и 1.40 ppm (s., 2 СН3–2’) in compound 4 allow to ascribe to them structures of cis-kellactone (1), 3’α-angeloiloxy-3’,4’-dihydroseselin (2), 3’α-oxy4’β-senecioiloxy-3’,4’-dihydroseselin (3) and 3’,4’-diangeloiloxy-3’,4’-dihydroseselin (4) (Mikailova, Serkerov 2014 ). H
H
H
H C
O
3
3'
H C 3
H
R1
R4
4'
R3
O
O
1. R1=R4=OH R2=R3=H 2. R1=R3=H R2=Angeloyloxy; R4=OH 3. R1=R3=H R2=OH; R4=Senecioyloxy 4. R1=R4=Angeloyloxy R2=R3=H
R2
References 1. Abyshev, A.Z., Agayev, E.M., Kerimov, Y.B. 2003. Chemistry and Pharmacology of Natural Boumarins. Baku, pp. 1-112. 2. Liang, T., Yue, W., Li, Q. 2010. Chemopreventive effects of Peucedanum praeruptorum Dunn. and its major constituents on SGC7901 gastric cancer cells. Molecules, 15: 8060-8071. 3. Mikailova, N.Kh., Serkerov, S.V. 2014. Diangelat kellactone - a new component of the Seseli campestre Bess. roots. Pharmacom, 2: 27-29.
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OP-12 New Metabolites from the AlgaE-Derived Fungi Penicillium thomii Maire and Penicillium lividum Westling Olesya I. Zhuravleva*,1,2, Maria P. Sobolevskaya2, Shamil Sh. Afiyatullov2, Natalya N. Kirichuk2
Far Eastern Federal University, Suhanova 8, Vladivostok 690950, Russian Federation G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, Prospect 100-let Vladivostoku 159, Vladivostok 690022, Russian Federation
[email protected]
1 2
Introduction Fungi isolated from the surface of marine algae have received great attention as a prolific source of chemically diverse bioactive metabolites. In our search for fungal secondary metabolites with novel chemical structures and/or cytotoxic activity we have investigated the strains Penicillium thomii KMM 4645 and P. lividum KMM 4663 associated with the marine brown alga Sargassum miyabei. Eleven new austalide meroterpenoids, seven new 6,6-spiroketals, sargassopenillines A–G and three new derivatives of furan-2-carboxylic acid were isolated from these marine fungi. Some of them are shown in Figure 1. Materials and Methods The fungi were cultured for 21 days on rice medium. The EtOAc extracts of the mycelium were purified by a combination of Si gel column chromatography and RP HPLC to yield individual compounds. The structures of the isolated compounds were determined based on spectroscopic methods. The absolute configurations of some of the metabolites were assigned by the modified Mosher’s method and CD data. Results and Discussion Austalide H acid, austalide H acid butyl ester, 13-O-deacetylaustalide I, 13-deacetoxyaustalide I and sargassopenilline C were able to inhibit AP-1-dependent transcriptional activity in JB6 Cl41 cell lines at non-cytotoxic concentrations. Also austalides exhibited significant inhibitory activity against endo-1,3-β-D-glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis. Sargassopenillines D and F and 5-(2’, 4’-dihydroxy-6’ -methylphenyl)-3methylfuran-2-carboxylic acid at a non-toxic concentration (10 µM) inhibit the adhesion of macrophages (30%–40% of inhibition). Acknowledgments The study was supported by the grant Russian Science Foundation No. 14-14-00030. HO
24 13
25 26
O
14 15
O
H
17
O
27 11 21 C 20
H
19 18
1
D
O
E
O O
29
OH O
HO HO 15
5 4a 4 7
O
1 8a
3
O
14
OH
HO
12 9
OAc
3'
1' 5
5'
O
7'
3
2
4
7
2
6
OH
O
Figure 1. Structures of 13-deacetoxyaustalide I (1), sargassopenilline F (2) and 5-(2’, 4’-dihydroxy-6’ -methylphenyl)3-methylfuran-2-carboxylic acid (3).
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OP-13 InvestigationS OF natural productS from medicinal plantS of Kazakhstan Janar Jenis1, Nurshat Kaldybayeva1, Haji Akber Aisa2
Faculty of Chemistry and Chemical Technology, Al-Farabi Kazakh National University, Almaty, 050038, Al-Farabi ave.71, Kazakhstan 2 Xinjiang Technical Institute of Physics and Chemistry, Central Asian of Drug Discovery and Development, Chinese Academy of Sciences, Urumchi, 830011, Beijing road 40-1, R. P. China,
[email protected] 1
Introduction Present time, the natural product chemistry will again be of great interest to research scientists and scholars working in the exciting field of new drug discovery. In Kazakhstan, over six thousand kinds of plants in which more than 6000 species of highest vascular plants, about 5000 species of mushrooms, 4851 species of lichen, more than 2000 species of seaweed are registered. 1,2 Meanwhile the plant resources have been efficiently used in the treatments of different kinds of diseases such as bronchitis, bronchial asthma, hepatitis, urethritis, chronic rheumatoid arthritis, nephritis, urolithiasis, pharyngitis, periodontitis, stomach pain, hyperacidity, diarrhea, hemostasia, metrorrhagia, snakebite, and cancer in Kazakh traditional medicine. Materials and methods We focused our attention on study of the bioactive chemical constituents of some Kazakh medicinal plants such as Dracocephalum nutans, Atriplex tatarica, Juniperus sabina and Bergenia crassifolia etc. All crude plant extracts were partitioned with n-hexane, chloroform, and n-butanol. Biological activities of the resulting extracts were screened. Then the extracts underwent bioassay-guided fractionation to ultimately isolating the active natural products as well as structures elucidation to discover the novel lead compounds and also to modify or develop the natural products. Results and Discussion The extracts of medicinal plants showed significant cytotoxic effects on several human cancer cell lines (HL-60, MCF7, and HepG2), together with antimicrobial and vasorelaxation activities. The active principles are responsible for the activity of the plant extracts which were identified as sesquiterpenes, diterpenes, triterpenes, lignans, flavonoids and alkaloids. As the results, six new bioactive diterpenoids have already been isolated from aerial parts of J. Sabina, galloylbergenin and phenolic compounds isolated from B. crassifolia which showed significant anti-lipid accumulation and vasorelaxant activities also four flavonoids, two triterpenoids isolated from D. nutans and their structures were elucidated based by 1H- and 13C-NMR spectra together with 1H-1H COSY, HSQC and HMBC spectra.3,4 Acknowledgments This research was partially supported by the Chinese Academy of Sciences Visiting Fellowship for Researchers from Developing Countries (Grant No. 2013FFGB0003). References 1. Xu, X., etal. 2009. The Kazakh Materia Medica, The Ethnic Press: Beijing. 1: 357. 2. Baytenov, M. C. 1963. Flora of Kazakhstan, Almaty,1: 71. 3. Jenis, J., Nugroho, A.E., Wong, Ch. P., Hirasawa, Y., Kaneda, T., Osamu, Sh., Hiroshi M. 2012. Sabiperones A-F, new diterpenoids from Juniperus Sabina, Chem. Pharm. Bull., 60(1): 154-159. 4. Jenis, J., Hirasawa, Y., Wong, Ch. P., Kaneda, T., Burasheva, G.Sh., Abilov, Zh.A., Morita H. 2012. New galloylbergenin from Bergenia crassifolia with anti-lipid droplet accumulation activity, Heterocycles, 86(2): 1591-1595.
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OP-14 ON A FACILE METHOD FOR ENHANCED THROUGHPUT IN ISOLATION OF LUPEOL FROM MARANTHES POLYANDRA J. V. Anyam*, I. S. Okoro, T. A. Tor-Anyiin, S. T. Asar, J. N. Anyam Department of Chemistry, University of Agriculture Makurdi, Nigeria
[email protected]
Introduction World Health Organization predicts that 84 million people would have died of cancer between 2005 and this year (2015). Needless to say, cancer a leading cause of death around the world. Lupeol and its derivatives possess anticancer properties; this along with a host of other medicinal activities is formidably documented (Gallo and Sarachine, 2009; Saleem, 2009; Wal et al., 2011) Materials and Methods Microwave Assisted Extraction was used for the extraction. Vacuum Liquid Chromatography was used for purification. The isolated Lupeol was characterized using 13C and 1H NMR. Method is suitable for extraction and purification of Lupeol from Lupeol-rich sources. Results and Discussion Here we report isolation of Lupeol from the stembark of Maranthes polyandra (Benth.) Prance (Chrysobalanaceae) for the first time and demonstrate a simple method for rapidly isolating this important medicinal compound in significant amounts (0.2 % w/w); an amount unprecedented (Anandjiwala et al., 2007; Laghari et al., 2011). References 1. Anandjiwala, S., Srinivasa, H., & Rajani, M. (2007). Isolation and TLC Densitometric Quantification of Gallicin, Gallic Acid, Lupeol and β-Sitosterol from Bergia suffruticosa, a Hitherto Unexplored Plant. Chromatographia, 66(9-10), 725–734. doi:10.1365/s10337-007-0389-1 2. Gallo, M., & Sarachine, M. (2009). Biological activities of lupeol. Int J Biomed Pharm Sci. Retrieved from http://www. globalsciencebooks.info/JournalsSup/images/0906/IJBPS_3(SI1)46-66o.pdf 3. Laghari, A., Memon, S., Nelofar, A., & Khan, K. (2011). Alhagi maurorum: a convenient source of lupeol. Industrial Crops and Products. Retrieved from http://www.sciencedirect.com/science/article/pii/S0926669011001087 4. Saleem, M. (2009). Lupeol, a novel anti-inflammatory and anti-cancer dietary triterpene. Cancer Letters. Retrieved from http://www.sciencedirect.com/science/article/pii/S0304383509003000 5. Wal, P., Wal, A., Sharma, G., & Rai, A. (2011). Biological activities of lupeol. Systematic Reviews in …. Retrieved from http:// www.sysrevpharm.org/article.asp?issn=0975-8453;year=2011;volume=2;issue=2;spage=96;epage=103;aulast=Wal
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OP-15 Beneficial effects of clove on oxidative stress and proinflammatory cytokines (interleukin-1, 6 and TNF-α) produced by adipose tissue, in rats fed a high-cholesterol diet A. Guenzet, & D. Krouf*
Laboratory of Clinical and Metabolic Nutrition, Faculty of Natural Sciences and Life University of Oran 1, Algeria
INTRODUCTION The present study was designed to investigate the possible effect of Clove (Syzygium aromaticum) lyophilized aqueous extract on oxidative stress and anti-inflammatory markers, in rats fed a high-cholesterol diet. Materials and Methods Three groups of rats were given a 20% casein diet enriched with 1% cholesterol + 0.5% cholic acid, for 6 weeks. The untreated group only received the high cholesterol diet (HC), whereas the other two groups received a diet supplemented with Syzygium aromaticum (HC-Sa) (2 g/kg bw) or Atorvastatin (40 mg/kg bw) (HC-ATS) by gavage. Control group was fed a standard diet during the experiment. Blood pressure is measured in the tail of rat using tail cuff System (Kent Scientific Corporation, USA). Tumor necrosis factor-alpha (TNF-alpha), interleukin (IL-1), IL-6 and prostaglandin I2 (PGI2) were assessed using enzyme immunoassays (Cayman Chemical’s ACETM EIA kit). A histological study was carried out to evaluate changes in adipose tissue and intuit the presence of inflammatory cells. Results and Discussion After 6 weeks, the hypercholesterolemic group displayed higher systolic and diastolic blood pressure (151/100 mmHg), plasma lipids and decreases in LCAT activity related to increased levels of oxidative stress markers (8-isoprostane, Lipid hydroperoxide generation, TBARS and impaired antioxidant defense systems, followed by pro-inflammatory state as described by an increase of TNF-alpha, IL-1, IL-6 and prostaglandin I2 (PGI2) (p succinatic acid. Exogenous succinic acid possessed only slight antihypoxic properties because of bad penetration into the cell. Succinate did not have effect practically on antihypoxic activity of amthizol, significantly decreasing antihypoxic action of gutimine [3]. The reason of this phenomenon was the physical and chemical properties of gutimine as a drug with рКа=5.9 [1]. The chemical bound of gutimine with succinate seemed to hydrolyse slightly in water solutions and tissues as well. That led to decrease of gutimine succinate penetration to cells compared to gutimine itself and, as a result, to loss of antihypoxic activity. Amthizol had рКа EC/SEE > EC/STA > EC/STE > EC/STM > EC/STC> EC/SEC. The highest DPPH radical scavenging effect was detected in the seed methanol extract. Some extracts of the species showed significant metal chelating capacity. It could be suggested that the seed methanol extract may be used a potential source of natural antioxidant in food and pharmacy industries. REFERENCES 1. Aruoma, O.I., Nutrition and health aspects of free radicals and antioxidants. Food Chem Toxic, 1994, 32: 671-683. 2. Yang, C.S., Landau, J.M., Huang, M.T., and Newmark, H.L., Inhibition of carcinogenesis by dietary polyphenolic compounds. Ann Rev Nutr, 2001, 21: 386-406.
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PP-150 Phenolic Compounds and Fatty Acid Composition of Euphorbia chamaesyce L. Feyza Oke-Altuntas1*, Ibrahim Demirtas2, Fatma Bulut2, Lutfi Behcet3
Department of Biology, Faculty of Science, Gazi University, 06500 Ankara, Turkey Department of Chemistry, Faculty of Science, Cankiri Karatekin University, 18100 Cankiri, Turkey 3 Department of Biology, Faculty of Science and Art, Bingöl University, 12000, Bingöl, Turkey 1 2
Introduction Euphorbia is one of the largest genus which belongs to Euphorbiaceae family and represented by 105 species in Turkey. Euphorbia species are named as “Sütleğen” (Baytop, 1994). The aim of this study was to investigate the detailed phytochemical analysis of Euphorbia chamaesyce L. Material and Methods E. chamaesyce (EC) was collected from Bingol, Turkey. Dried and powdered stem (ST) and seed (SE) parts of C E. chamaesyce were cut into small pieces. The crushed parts were dissolved in hexane(H), chloroform (C), ethyl acetate (E), acetone(A) and methanol (M) in a week time of each solvent for three times at room temperature. The extracts were filtered and evaporated. Phenolic contents of the extracts were determined qualitatively and quantitatively by high performance liquid chromatography/time of flight-mass spectrometry (HPLC/TOF-MS). Fatty acid composition of the hexane extracts was performed by GC-MS. Results and Discussion Gallic acid, rutin, ferulic acid, chicoric acid, caffeic acid, p-coumaric acid, quercetin, kaempferol, cinnamic acid, gentisic acid, vanillic acid, protocatechuic acid, 4-hydroxybenzoic acid were found in the extracts. The major constituents of the fatty acids obtained from the seed and stem hexane extract were determined as linoleic acid (C18:2 ) (32.6%, 21.9%, respectively), linolelaidic acid (C18:3) (13.8%, 13.7%, respectively), and palmitic acid (C16:0)(10.4%, 9.15%, respectively). This study provides first report on the detailed phytochemical screening of E. chamaesyce. References 1. Baytop T. 1994. Türkçe Bitki Adları Sözlüğü [Dictionary of Vernacular Names of Wild Plants of Turkey]. Ankara: Türk Tarih Kurumu Basımevi, 385 pp 2. Oztekin M. 2012. Euphorbia L. In: Güner A, Aslan S, Ekim T, Vural M, Babac MT, editors. A checklist of the flora of Turkey (vascular plants). Istanbul: Nezahat Gökyiğit Botanic Garden (NGBB), ANG Foundation and Flora Research Society; p. 414 –424.
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PP-151 ESSENTIAL OIL COMPOSITION AND ANTIOXIDANT PROPERTIES OF CENTAUREA CARIENSIS SUBSP. MACULICEPS (O. SCHWARZ) WAGENITZ Ayhan Altıntaş*1, 2,Fatih Göger1, Elif Dündar3, Betül Demirci1
Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470 Eskişehir, TURKEY 2Anadolu University, Yunus Emre Vocational School, 26470, Eskişehir, TURKEY 3 Anadolu University, Graduate School of Health Sciences, Department of Pharmacognosy, 26470 Eskişehir, TURKEY
[email protected] 1
Introduction The genus Centaurea (Asteraceae) is represented in the world aproximatelly by 600 species, 222 of which are represented in Flora of Turkey with % 67 endemism rate. Turkey is the main gene center of the genus (Bona, 2015). Several members of this genus are used in Anatolian folk medicine. Materials and Methods In the present study, Centaurea cariensis subsp. maculiceps was subjected to hydrodistillation for 3 h using Clevenger type apparatus and the oil trapped in hexane was analysed by GC-MS. Identification of the essential oil components was carried out by comparison of their relative retention times with those of authentic samples or by comparison of their relative retention index (RRI) to the series of n-alkanes. Computer matching against commercial (Wiley GC/MS Library, Adams Library, MassFinder 2.1 Library), and in-house “Baser Library of Essential Oil Constituents” built up by genuine compounds and components of known oils, as well as MS literature data, were used for the identification. Deodorized water extract of plant material obtained from the marc after clevenger distilation was freze dried and used for antioxidant activity tests. Deodorized water extract of Centaurea cariensis subsp. maculiceps was tested for its free radical scavenging activity, using the the 1,1-Diphenyl-2-picrylhydrazyl (DPPH) screning assay (Kumarasamy et al.,2007). Total phenolics of the extract was determined according to the (Singletton et al., 1998) method. Results and Discussion Main components of the essential oil were found as hexadecanoic acid (28.6%), carvacrol (12.0%), dodecanoic acid (9.2%), caryophyllene oxide (6.1%), heptacosane (5.7%). Antioxidant capacity results were found as IC50 values of 0.143±0.051 mg/mL while positive control gallic acid showed IC50 value as 0.002 mg/ml. Total phenolic content was determined as 47.79±4.28 mg/GAE. References 1. Bona, M. 2015. Centaurea goksivriensis (Asteraceae), a new species from Turkey, Phytotaxa, 203 (1): 063–068. 2. Kumarasamy, Y., Byres, M., Cox, P.J., Jaspars, M., Nahar, L., Sarker S.D. 2007. Screening seeds of some Scottish plants for free-radical scavenging activity. Phytother Res., 21, 615-621. 3. Singleton, V. L.; Orthofer, R.; Lamuela-Ravento′s, R. M. Analysisof total phenols and other oxidation substrates and antioxidantsby means of Folin-Ciocalteu reagent. In Methods in Enzymology;Packer, L., Ed.; Academic Press: San Diego, CA, 1999; Vol. 299,pp 152–315.
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PP-152 Simultaneous Determination of β–acetoxyisovaleryalkannin by HPLC in Arnebiae Radix Haji Aikebaier Aisa3* , Abudureyimu Abudukerimu 1,Abudureyimu Miernisha1, Ting-xia Dong2, Jiang-yang Guo2, Wah-keung Karl Tsim2
Xinjiang Uyghur Medicine Hospital,wulumuqi; The Hong Kong University of Science and Technology Life Science Division & Center for Chinese Medicine R&D, Clear Water Bay, Kowloon, Hong Kong, SAR; 3 The Xinjiang Technical Institute of Physics and Chemistry, China Academy of Science, Wulumuqi, 830001)
[email protected] 1 2
Introduction Arnebia euchroma (Royle) Johnst. is one of the most commonly used uyghur traditional drugs,used for the treatment of Sores, eczema , burns and has antitoxic activity.Aim of this research is to establish fingerprints to assess the quality of Arnebiae Radix and to determine the contents of β-acetoxyisovaleryalkannin derived from Arnebia euchroma (Royle) Johnst. which is in order to provide the evidence for the quality control of Arnebiae Radix in new version of the Chinese Pharmacopoeia . Materials and Methods HPLC fingerprinting and content determination methods were applied to evaluate the quality of Arnebiae Radix.Ten batched of samples were detected by an ACE C18 column ( 4.6 mm x 250 mm, 5 µm) using acetonitrile-0.1 % formic acid with water Isocratic system as mobile phase. The wavelength of detection is 516 nm for fingerprinting and content determination of β-acetoxyisovaleryalkannin in Arnebiae Radix. Results and Discussion HPLC fingerprint of Arnebiae Radix was established and could be used for quality assessment of Arnebiae Radix. The results showed the characteristic HPLC fingerprints peaks of these ten batches in Arnebiae Radix. The contents of β-acetoxyisovaleryalkannin showed the differences from differenr sources of Arnebiae Radix. β-acetoxyisovaleryalkannin can be good chemical marker for the quality control of Arnebiae Radix. It has been used in Hong Kong Chinese Materia Medica Standards. Acknowledgments and References 1. The people’s Republic of China Pharmacopoeia,2010, The State Pharmacopoeia Commission, The medicine science and technology press of China, Vol 1, 230 2. Papageorgiou VP, Assimopoulou1 AN, Couladouros EA, et a.,1999,The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products[J]. Angewandte Chemie International Edition, 3 (38): 270-301. 3. Shen CC, Syu WJ, Li SY, et al. Antimicrobial activities of naphthazarins from Arnebia euchroma,2002,. J. Nat Prod, 65(12): 1 857-1862. 4. Sevimli-Gur C, Akgun IH, Deliloglu-Gurhan I, et al. Cytotoxic naphthoquinones from Alkanna cappadocica, 2010 , J Nat Prod, 73(5): 860-864.
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PP-153 CHOLINESTERASE INHIBITORY ACTIVITY OF ORIGANUM VULGARE L. SUBSP. HIRTUM AND ITS CONSTITUENTS Rümeysa Yücer*1 Burcu Çulhaoğlu2 Gülaçtı Topçu1
Bezmialem Vakıf University, Faculty of Pharmacy, Department of Pharmacognosy, 34093, Istanbul, Turkey Bezmialem Vakıf University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 34093, Istanbul. Turkey
[email protected]
1 2
Introduction Turkey is an important gene-centre for the family Lamiaceae (Labiatae). There are 41 Origanum species in the world. The Flora of Turkey has 22 species and 32 taxa of Origanum, 21 taxa being endemic to Turkey, and the ratio of endemism in the genus is 63%. Origanum species are used in traditional medicine all around the world, possessing antioxidant, anticholinesterase, antibacterial, antifungal and anti-inflammatory effects (Ozkan et al., 2011; Loizzo et al., 2009; Miller et al., 2015). Origanum vulgare L. subsp. hirtum known as “Istanbul kekiği” in Turkey and widely used as kekik in Marmara and Thrace regions (Esen et al., 2007). Materials and Methods Plant was dried at room temperature and ground to fine powder in a mechanic grinder. It was then successively extracted with dichloromethane, and subsequently methanol. Isolation studies were made on Si-gel columns and isolates were purified by preparative TLC, and HPLC used for polar compounds. Methanol and dichloromethane extracts of the aerial parts of Origanum vulgare L. subsp. hirtum were investigated against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes by modified Ellman method (Ellman et al., 1961). Results an Discussion Purification studies are continuing, and structure elucidation studies of pure compounds have been made based on namely 1D- and 2D NMR and mass spectroscopic techniques. Pure triterpenoids ursolic acid and oleanolic acid have yet been obtained. The anticholinesterase activity tests are still ongoing for the extracts and pure compounds. References 1. Esen,G., Azaz, A.D, Kurkcuoglu, M., Baser, KHC., Tinmaz, A. 2007. The essential oil and antimicrobial activity of wild and cultivated Origanum vulgare L. subsp. hirtum (Link) Ietswaart from Marmara region in Turkey. Flavour Fragr. J., 22: 371-376. 2. Ellman, G.L., Courtney, K.D., Andres, V., Featherston, R. M. 1961. Biochem. Pharmacol., 7, 88-95. 3. Loizzo, M.R., Menichini, F., Conforti, F., et al. 2009. Chemical analysis, antioxidant, anti inflammatory and anticholinesterase activities of Origanum ehrenbergii Boiss and Origanum syriacum L. essential oils. Food Chem, 117:174-180. 4. Miller, A.B., Cates, R.G., Lawrence, M., et al. 2015. The antibacterial and antifungal activity of essential oils extracted from Guatemalan medicinal plants. Pharm. Biology, 53: 548-554. 5. Ozkan, A., Erdoğan A. 2011. A comparative evaluation of antioxidant and anticancer activity of essential oil from Origanum onites (Lamiaceae) and its two major phenolic components. Turk J Biol, 35: 735-742.
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PP-154 Flavones from Endemic Centaurea kilaea Boiss. Ali Şen, Leyla Bitiş*
Marmara University, Faculty of Pharmacy, Department of Pharmacognosy, İstanbul, Turkey. *
[email protected]
Introduction The Centaurea L. genus of Asteraceae is represented with more than 205 taxa in Turkey. In previous phytochemistry studies on various Centaurea species the occurrence of secondary metabolites such as flavonoids, sesquiterpene lactones, triterpenes, alkaloids have been reported (Sen et al., 2014; Polatoglu et al., 2014). The purpose of the present study was to isolate and identify flavonoids from aerial parts of Centaurea kilaea Boiss. Materials and Methods Plant samples were collected in the flowering periods from the Catalca region of Istanbul in 2009 and identified by Dr. Gizem Bulut, a botanist at the Faculty of Pharmacy, University of Marmara. Voucher specimens were deposited in the Herbarium of the Faculty of Pharmacy, Marmara University (MARE No: 11712). Dried aerial parts of C. kilaea (1595 g) were separately extracted with n-heptane, chloroform and methanol using maceration method. The chloroform extract (20 g) was subjected to a silica gel column (800 g) and eluted by gradient elution (Hexane-CHCI3-CH3OH) to afford 20 fractions. Fractions were combined according to their TLC behaviour to yield CKCSI (F4-10), CKCSII (F11-14) and CKCSIII (F15-20). Compounds from CKCSII fraction have been isolated by repeated chromatography techniques (silica gel and sephadex LH-20 column chromatography, silica gel preparative TLC) Results and Discussion
Five known 5-hydroxyflavones; 5,7-dihydroxy-6,4’-dimethoxyflavone(Pectolinarigenin)(1), 5-hydroxy-6,7,3’,4’tetramethoxyflavone (6-hydroxyluteolin-6,7,3’,4’-tetramethyl ether)(2), 5-hydroxy-6,7,4’-trimethoxyflavone (Salvigenin) (3), 5,7,4’-trihydroxyflavone (Apigenin)(4), 3’,5-dihydroxy-6,7,4’-trimethoxyflavone (Eupatorin)(5) were isolated from aerial parts of Centaurea kilaea and the structures of compounds were elucidated by UV and 2D NMR spectral analysis. Compounds 1,2 and 3 have previously been found in C. kilaea (Salan et al., 2001). Compounds 4 and 5 were isolated from this species for the first time. Acknowledgments Authors are grateful to Dr. Gizem Bulut for identification of plant material. This study is a part of PhD thesis of Ali Sen entitled “Antiproliferative activity-guided isolation of active compounds from Endemic Centaurea kilaea” and was supported by the Research Fund of the University of Marmara, Project No. SAG-C-DRP-280214-0034. Ali Sen thanks to the Scientific and Technological Research Council of Turkey (TUBITAK) for Domestic PhD Scholarship intended for Priority Areas (Code: 2211-C). References 1. Sen,A., Gurbuz,B., Soyogul-Gurer,U., Bulut, G., Bitis,L. 2014. Flavonoids and biological activities of Centaurea stenolepis. Chemistry of Natural Compounds, 50: 128-129. 2. Polatoğlu, K., Şen, A., Bulut, G., Bitiş, L., Gören, N. 2014. Essential Oil Composition of Centaurea kilaea Boiss. and C. cuneifolia Sm. from Turkey. Natural Volatiles & Essential Oils, 1: 55-59. 3. Salan, Ü., Topçu, G., Öksüz, S. 2001. Flavonoids of Centaurea kilaea and C. Salonitana, Journal of Faculty of Pharmacy of Istanbul University, 34: 55-61.
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PP-155 Two sesquiterpenoides from Vernonia anthelmintica (L.) Willd. Ablajan Turak 1, 2, 3, Salamet Edirs 2, 3, Yongqiang Liu 1, 2, H. A Aisa 1, 2, *
Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, P. R. China 2 Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011 China 3 University of Chinese Academy of Sciences, Beijing 100039, P.R. China
[email protected] 1
Introduction Vernonia anthelmintica (L.) Willd, called Kaliziri in Xinjiang (North West of China), is a plant which only grows in highaltitude areas of southern Xinjiang and small regions in Pakistan and India, and is a famous medicine that used to cure vitiligo in traditional Uyghur medicine (TUM). V. anthelmintica belonging to Asteraceae have been shown to produce various types of sesquiterpene lactones, such as eudesmanolides, germacranolides, guaianolides, and elemanolides. Materials and Methods The air-dried seeds (15 Kg) of V. anthelmintica were extracted with petroleum ether (PE) (102 L) followed by extracting with PE: ether: MeOH (PEM) = 1:1:1 (104 L) and MeOH (136 L) successively. The PEM extract (457 g) was subjected to a silica gel column (100-200 mesh; PE/ EtOAc, 1:0 0:1, v/v) to produce 10 major fractions (F1 – F10), monitored by TLC. Fractions F3 was chromatographed on silica gel, ODS and sephadex LH columns and then purified by preparative HPLC to yield two sesquiterpenoids cynaropicrin (1) and deltoidealactone (2). Their structures elucidated by 1D and 2D NMR data are shown in Fig.1. O O
H HO
H O
OH O
O H
H
H O
O O 1
OH
O 2
Fig.1 Structures of compounds 1 and 2. Results and Discussion Two sesquiterpenoids named cynaropicrin (1) and deltoidealactone (2) were isolated from the PEM extract of V. anthelmintica. These substances were isolated from the genus Vernonia for the first time. Acknowledgments This work was financially supported by the Funds for International Cooperation and Exchange of the National Natural Science Foundation of China (Grant No. 31110103908). References 1. Marco, J. A. 1989. Sesquiterpene lactones from Artemisia herba-alba subsp. Herba-alba. Phytochemistry, 28: 3121-3126. 2. Bardon, A., Catalan, C. A. N. Gutierrez, A. B., Herz, W. 1988. Guaianolides and other constituents from Vernonia nitidula. Phytochemistry, 27: 2691-2694. 3. Ganjian, I.; Kubo, I., Fludzinski, P. 1983. Insect antifeedant elemanolide lactones from Vernonia amygdalina. Phytochemistry, 22: 2525-2526. 4. Liu, Y. Q., Nugroho, A. E., Hirasawa, Y., Nakata, A., Kaneda, T., Uchiyama, N., Goda, Y., Shirota, O., Morita, H., Aisa, H. A. 2010. Vernodalidimers A and B, novel orthoester elemanolide dimers from seeds of Vernonia anthelmintica. Tetrahedron Lett., 51: 6584-6587. 5. Koul, J. L., Koul, S., Singh,C., Taneja, S. C., Shanmugavel, M., Kampasi, H., Saxena, A. K., Qazi, G. N. 2003. In Vitro Cytotoxic Elemanolides from Vernonia lasiopus. Planta Med., 69: 164-166. 6. Luo, X., Jiang, Y., Fronczek, F. R., Lin, C., Izevbigie, E. B., Lee, K. S. 2011. Isolation and structure determination of a sesquiterpene lactone (vernodalinol) from Vernonia amygdalina extracts. Pharm. Biol., 49: 464-470. 7. Cardona, L., Aleman, R. A., Garcia, B., Pedro, J. R. 1992. Sesquiterpenes, flavonoids and lignans from Onopordon acaulon. Phytochemistry, 31: 3630-3632.
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PP-156 Supercritical CO2 extraction of Nitraria sibirica Pall. seed oil and its fatty acid composition analysis Mahinur Bekri1, Abdumijit Abdukadir2, Junping Zhang1, H. A. Aisa1*,
The Key Laboratory of Plant Resources and Chemistry in Arid Regions and Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China 2 College of Pharmacy, XinjiangMedical University, Urumqi 830011, China
[email protected] 1
Introduction Nitraria sibirica Pall. belonging to the Zygophyllacea family, is one of the dominant species in Xinjiang, China. As a traditional Uyghur herb, the fruits and leaves of Nitraria sibirica Pall. are used to treat hypertension, menstrual disorders and gestroenterities (Liu,1999). Up to date the components of Nitraria sibirica seed oil have not been analyzed. Due to their ecological and medicinal values, seed oil was extracted by supercritical CO2 fluid and its fatty acid components were analyzed by GC MS, which provided the basic data for the further development of Nitraria resource. Materials and Methods The Nitraria sibirica seeds were smashed to powder with diameters about 4.0mm. 200g powder was weighed and extracted in the extraction pot. During the extraction process, the optimization conditions of this method were: CO2 fluids used in cycle at the flow rate 10 L/min; extraction pressure 40Mpa; extract in temperature 55; extract period 2 hours. The chemical structures of components were searched and identified by NIST08 databases. Results and Discussion Table1 Identified chemical components of Nitraria sibirica seed oil extracted by SFE- CO2 Peak No
Formula
Chemical constituent
Relative content（%）
1 2 3 4 5 6 7 8
C17 H34O2 C19H38O2 C19 H36O2 C19H36O2 C19H34O2 C19H34O2 C21 H42O2 C23H46O2
Methyl palmitate Methyl octadecanoate Methyl 9-octadecenoate 9-Octadecenoic acid, methyl ester Methyl linoleate Methyl linolenate Eicosanoic acid, methyl ester Docosanoic acid, methyl ester
4.166 2.317 25.747 0.473 65.671 0.977 0.327 0.322
Results given in table1 showed the component with high content (> 65%) of linoleic acid, oleic acid (25%) and linolenic acid (1%) which are the essential unsaturated fatty acid for human body. The study showed that the probability of coronary artery disease decreases linearly with the increase of quantities of the unsaturated fatty acids in food stuff (Gil-Villarino, 1997). Unsaturated fatty acids play an important role in human life for its anti-oxidative and health care properties. The seed oil of Nitraria sibirica has practical values. Acknowledgments This work was supported by West Light Foundation of Chinese Academy of Science (Grant No.XBBS201312).
References 1. Liu, Y.M.,Imam, Sawut. 1999.Pharmacography of Uyghur(volume one).Xinjiang people’s publishing house,Urumqi,pp.206-209. 2. Gil-Villarino,A.,Tortes MI.,Aafra.1997.Supplemantation of coconut oil from different sources to the diet induces cellular damage and rapid changes in fatty acid composition of chick liver and hepatic mitochondria. comparative biochemistry and physiolog,117c:243-250.
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PP-157 Determination of the polyphenols in the antibacterial extraction from pomegranate peel by LC-MS and quantitative analysis of major compounds Rahima Abdulla 1,2,3, Sanawar Mansur1,2,, Li Chunting1, Ablikim Ubul1 , Haji Akber Aisa 1* 1 Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China ; 2 Graduate University of the Chinese Academy of Sciences, Beijing 100049, China
[email protected]
Introduction Pomegranate peel, a by-product of the pomegranate juice and pomegranate wine industry. Its major class of phytochemicals is the polyphenols, including flavonoids, hydrolysable tannins and phenolic acids, which constitute approximately 10-20% of dry weight [1-4]. Our research group previously studied antibacterial, antioxidant and antitumor bioactivities of pomegranate polyphenols, and confirmed the optimized preparing techniques for standard polyphenol extraction with antibacterial activities [5-7]. Therefore, in order to better explain the active substances and mechanism, its chemical compositions were identified by HPLC-MS / MS in this study. Another significant goal of this study was to clarify the quantities of major polyphenol contents by HPLC. Materials and Methods The polyphenols extraction of pomegranate peel (PEPP, obtained by our research group) 50.1mg was dissolved in 10mL, 50% methanol before analysis. High performance liquid chromatography (HPLC) coupled to negative electrospray ionization (ESI) employing a timeof-flight tandem mass spectrometer (TOF-MS) was used to analyze components of polyphenols from the peel of Punica granatum L. by comparing the retention time, fragmentation behaviors at low and high collision energy. Results and Discussion A total of more than 49 compounds including ellagitannins and gallotannins, ellagic acid derivatives, flavonols were identified. Additionally, a rapid HPLC–UV method for qunantification of seven major polyphenols( punicalagin,punicalin, ellagic acid,gallic acid, corilagin, astralagin and gallocatechin ) was estabilished. The results showed that, punicalagin is one of the main compounds which constitutes 53.2% in this polyphenol extraction. References 1. Navindra, P. S., Risa, N.S., David H., 2006. Pomegranates: Ancient Roots to Modern Medicine,3-14. 2. Mavlyanov S.M., Islambekov S.Y., Karimdzhanov A.K., et al. 1997. Polyphenols of the fruits of some varieties of pomegranate growing in Uzbekistan. Chem. Nat. Compd., 33(1): 98-99. 3. Chauhan D., Chauhan J.S. 2001.Flavonoids diglycoside from Punica granatum. Pharm Bio., 39 (2):155 -157.
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PP-158 Antihypertensive activity of Ziziphora clinopodioides Lam. Guo Dan1,2,3, Maidinuer Aini1,2, Duolikun1,2, Lin Jianbo1,2, Zou Guoan1,2*
Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011, Urumqi, P. R. China, fax:+86 991 3835679, 2 Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences;P. R. China. 3 University of Chinese Academy of Sciences, 100049, Beijing, P. R. China.
[email protected]; 1
As a medicinal and edible plant, Ziziphora clinopodioides Lam. (Labiatae), mainly distributed in Xinjiang of China, Iran, Turkey, Mongolia, and Central Asia, is commonly used in traditional Uyghur medicine for the treatment of fever, edema, neurasthenic, insomnia, tracheitis, lung abscess, hemorrhoids, hypertension, angina pectoris, coronary artery disease and other cardiovascular diseases (1-4). Former phytochemical investigations on genus Ziziphora mainly focused on essential oil components, along with a few flavonoids, caffeoyl derivatives, fatty acids, phenolic acids, triterpenoids, and sterols (1). In the present study, antihypertensive activity of Z. clinopodioides was assayed using commonly adopted in vitro model of rat thoracic aortic rings (1), with the result that EtOAc fraction and CHCl2 fraction were active fractions, EC50 values of which were 0.34±0.03, and 0.59±0.02 g/L, together with Emax values of 94.35±3.59%, and 75.16±5.48%, respectively. Further bioassay-guided fractionation led to the isolation of 4 potential vasorelaxant principles, identified as apigenin, luteolin, methyl rosmarinate, and oleanolic acid. ACKNOWLEDGEMENT We gratefully acknowledge financial support from National Natural Science Foundation of China (81102891). REFERENCES 1. Committee of Flora Xinjiangensis. 2004. Flora Xinjiangensis. vol. 4. Xiangjiang Science & Technology Publishing House, Urumqi, pp 327. 2. Liu, Y. M., Liu, W. X., Yikemu, S., Zou, Y. 1999. Pharmacography of Uighur. vol. 1. Xinjiang Sci-Tech and Public Health Press, Urumqi, pp 446-449. 3. Senejoux, F., Demougeot, C., Kerram, P., Aisa, H. A., Berthelot, A., Bevalot, F., Girard-Thernier, C. 2012. Bioassay-guided isolation of vasorelaxant compounds from Ziziphora clinopodioides Lam. (Lamiaceae). Fitoterapia, 83: 377-382. 4. Ye, Y. H., Ba, H., Liu, Y. Q., Zou, G. A., Aisa, H. A. 2012. Chemical constituents of Ziziphora clinopodioides. Chem. Nat. Comp., 48: 681-682.
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PP-159 Chemical Composition of Saussurea involucrata Seeds Maira Seiilgazy1,2, Haji Akbar Aisa1,*
Key Laboratory of Plant Resources in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, CAS, Urumqi 830011, China 2 University of Chinese Academy of Sciences, Beijing 100039, P.R. China
[email protected] 1
Introduction The seeds of Saussurea involucrata can germinate at 0 °C and grow at 3 °C to 5 °C and the tender seedling can survive in 20 °C below zero. It will take five year for it to blossom but the actual growing time is only eight months. Saussurea involucrata has long been used under the herbal name “Snow louts” for the treatment of rheumatic arthritis, stomachache and gynopathy in traditional folk medicine. All these characters are very spectacular in biology. Not enough literature is available regarding the chemical composition of the seeds of Saussurea involucrata. Materials and Methods The air-dried and powdered seeds of S. involucrata (3 kg) were extracted in triplicate with 95% EtOH under the reflux at 60 °C temperatures. Solvent was evaporated and the dry residue was suspended in water, then treated with petroleum ether, chloroform and ethyl acetate. The chloroform fraction was subjected to column chromatography over silica gel (100–200 mesh) and eluted with a gradient CHCl3–MeOH to afford five fractions (A–E). Results and Discussion, The chloroform fraction was subjected to column chromatography over silica gel (100–200 mesh) and eluted with a gradient CHCl3–MeOH to afford five fractions (A–E). Fraction D (24g) was separated by silica gel column chromatography (200–300 mesh) eluted with a gradient mixture of Hexane: chloroform (30:1 - 0:100) - Chloroform and Chloroform: methanol (100:0- 0:100) to give five individual compounds Arctigenin (C21H24O6) (1), Arctiin C27H34O11 (2) and other compounds (3-5). Structures of compounds (3-5) have not been established yet. Structures of isolated compounds were established on the basis of physical and chemical properties and the analysis of their spectral data as IR, UV, 1H, 13C and 2D NMR. H3CO HO
3`
4`
2`
O
7`
8`
1`
O
8
6`
HO
9
7
5`
H3CO
9`
5``
1
6
OH
2 3
5 4
6``
OCH3
OCH3
Arctigenin (1) Acknowledgments
HO
O
O
3`
4`
2`
9`
O
8
6`
9
7
5`
1 2
1``
3
5
OH
8`
1`
6
3``
O
7`
OCH3
4
OCH3
Arctiin (2)
This work was supported by the Projects of CAS-TWAS president fellowship and Xinjiang Technical Institute of Physics and Chemistry the Central Asian Drug Discovery & Development Centre of Chinese Academy of Sciences. References 1. State Pharmacopoeia Committee of the People’s Republic of China, Pharmacopoeia of the People’s Republic of China, Part I (China Medical Science and Technology Press, Beijing, 2005). 2. Yi-Dong Liu, Haji Akber Aisa. 2010. Three new lignans from the seeds of Saussurea involucrate. Journal of Asian Natural Products Research Vol. 12, No. 10, October 2010, 828–833
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PP-160 CHEMICAL STUDY OF LEAVES OF Lycium barbarum Yan Wang 1,2 , H.A. Aisa 1,*
Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China 2 University of Chinese Academy of Sciences, Beijing 100039, PR China
[email protected] 1
Lycium barbarum L. is a Solanaceous defoliated shrubbery that is widely distributed in Northwestern China, Southeastern Europe and the Mediterranean areas (1). Fruits, rootbarks, and leaves of L. barbarum have been used in Traditional Chinese Medicine. The leaves, were called as “tianjingcao” and were recorded as nourishing the liver and enhancing eyesight in the Chinese medicinal monograph “ben cao gang mu”(2). We studied the leaves of L. barbarum, provided by Xinjiang Jinn’s Medlar BNP Industries Co., Ltd, China and identified by Prof. Guanmian Shen (Xinjiang Institute of Ecology and Geography, Chinese Academy of Sciences). Dried leaves (10.0 kg) were extracted with 70% EtOH(8L× 9) at room temperature. The combined EtOH extracts were evaporated to yield EtOH extracts. (1080g).The EtOH extracts was suspended in water and then extracted with petroleum ether, CHCl3, EtOAc, and n-BuOH successively. Evaporation of the respective solvents gave the petroleum ether (194 g), CHCl3 (22g), EtOAc (10 g), and n-BuOH (200 g) extracts. Both the CHCl3and EtOAc fractions were separated and purified by column chromatography on silica gel, Sephadex LH-20, ODS and RP HPLC. Thirteen compounds were isolated and identified as dehydrovomifoliol (1), loliolide (2),2,6,2’,6’-tetramethoxy-4,4’bis(2,3-epoxy-1-hydroxypropyl) biphenyl (3), ethyl-(4-hydroxyphenyl) acrylate 4), indole-3-carboxylic acid (5), caffeic acid ethyl ester (6), palmitic acid (7), dibutyl phthalate (8), rutin (9) , scopolin (10), p-Hydroxybenzoic acid (11), P-coumaric acid (12), feruic acid (13). Compounds 1-6 (Fig.1) were obtained from this genus for the first time. O
OMe MeO
H O O HO
O
O H
OH
HO
2
H
H
MeO
MeO
1
H H
H H
O
H
H
3 HO O
O HO
O
HO O
4
O
HO
5
6
Fig.1 Structures of compounds 1-6
REFERENCES 1. Jin, M.L., Huang, Q.s., Zhao, K., Shang, P. 2013. Biological activities and potential health benefit effects of polysaccharides isolated from Lycium barbarum L.. International Journal of Biological Macromolecules, 54:16-23. 2. Potterat, O. 2010. Goji (Lycium barbarum and L. chinense):Phytochemistry, Pharmacology and Safety in the Perspective of Traditional Uses and Recent Popularity. Planta Med, 76: 7-19.
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PP-161 New alkaloids isolated from Fritillaria pallidiflora Yan Li1, 3, A Yili1, 2*, H. A. Aisa1, 2*
Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, PR China 2 Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China 3 University of Chinese Academy of Sciences, Beijing 100039, PR China
[email protected],
[email protected] (H.A. Aisa). 1
The air-dried bulbs of Fritillaria pallidiflora Schrenk (20.0 kg) were extracted with CHCl3 after mixed with ammonium hydroxide. The extracts were combined, treated with HCl (5%), NH4OH, Na2CO3, NaOH and CHCl3. The solvent were concentrated under reduced pressure to give the brown residue (59.0 g). The extract was chromatographed on silica gel, Sephadex LH-20 and reversed-phase HPLC. Five new steroidal alkaloids, respectively yibeinone A (1), yibeinone B (2), yibeinone C (3), yibeinone D (4) and yibeinone E (5) (Fig.1) were isolated from them together with four known steroidal alkaloids Imperialine (6) (1), Imperialine-3β-D-glucoside (7) (1), Imperialine N-oxide (8) (2) and Dongbeinine (9) (3). Compounds 8, 9 were obtained from F. pallidiflora for the first time. R4
H
H
H
H H
HO
H HO
N
H H N
O
R3 OH H
H H
R2 2
H R1
H 3
H
O
4
R1
R2
OH
OH
H H
OH
OGlc OGlc H
OH
R3
H H N
R4
H H H
H
H
H
H HO
H
H
1
O
O H
O 5
Fig.1 Structures of compounds 1-5 Acknowledgments
Joint Funds of the National Natural Science Foundation of China and we are grateful to Professor Khayrulla
Bobakulov for his kind guidance in deducing the structure of new compounds. References
1. Huang, E.Y., Li, C.S., Xu, D.M. 1990. Studies on the alkaloid constituents of Fritillaria pallidiflora Schrenk. China Journal of Chinese Materia Medica, 15:39-41. 2. Zhang, A.J., Wang, H.Y., Tang, X.Y., Zheng, Y., Yi, X.H., Yu, K.B. 1998. Isolation and structure elucidation of alkaloids from the bulb of Fritillaria wabuensis. Original paper, 64:448-450. 3. Zhang, J.X., Lao, A.N., Xu, R.S. 1993. Two new steroidal alkaloids, dongbeinine and dongbeirine, from Fritillaria thunbergii Miq. Var. Chekiangensis. Chinese chemical letters, 4:321-322.
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PP-162 Antioxidants from Ziziphora clinopodioides Lam. by combination of chromatographic techniques Guo Dan1,2,3, Rahima Abdulla1,2,3, Luo Yuqin1,2, Zou Guoan1,2*
Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011, Urumqi, P. R. China, fax:+86 991 3835679, 2 Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, P.R. China 3) Graduate University of Chinese Academy of Sciences, 100049, Beijing, P. R. China.
[email protected]; 1
As a continuous research into the chemical constituents from Ziziphora clinopodioides Lam. (2), which was found to possess a significant antioxidant capacity in the present study. Bioassay-guided fractionation of antioxidants from the EtOAc fraction of Z clinopodioides, by combination of silica gel column chromatography (CC) with high-speed countercurrent chromatography (HSCCC), led to the isolation of 3 active components, methyl rosmarinate, caffeic acid, and luteolin, with IC50 values of 13.43±0.77, 15.19±0.81, and 16.65±0.92 μM, respectively. Their structures were identified by comprehensive analyses of mass spectroscopy, 1H, and 13C nuclear magnetic resonance spectroscopy. Silica gel CC separation was conducted with chloroform–methanol (1:0-0:1, v/v) in a gradient manner. HSCCC separation was performed with a two-phase solvent system composed of n-hexane–ethyl acetate–methanol–water (3:5:3:5, v/v) at a flow rate of 1.5 mL/min, which was successfully selected by thin layer chromatography analysis. The crude samples and fractions were analyzed by HPLC under the optimum analytical condition of acetonitrile–0.1% formic acid (5:95) to (60:40) in 60min, then to (100: 0) in 5 minutes. Antioxidant activity of EtOAc extract and compounds yielded from the active fraction was assayed by in vitro ABTS [2,2’-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) diamonium salt] radical cation decolorization assay (1) with VC as positive control. ACKNOWLEDGEMENT We gratefully acknowledge financial support from National Natural Science Foundation of China (81102891). REFERENCES 1. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C., 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol. Med. 26: 1231–1237. 2. Ye, Y. H., Ba, H., Liu, Y. Q., Zou, G. A., Aisa, H. A. 2012. Chemical constituents of Ziziphora clinopodioides. Chem. Nat. Comp., 48: 681-682.
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PP-163 INVESTIGATIONS INTO THE CHEMICAL PROFILE OF PRUNUS DULCIS NUTS Muhammad Nasimullah Qureshi1,2, Haji Akber Aisa1,*
Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. China. 2 Department of Chemistry, Abdul Wali Khan University Mardan, Mardan 23200, Pakistan.
[email protected] 1
Introduction Prunus dulcis has long been known as a source of nutrients in many traditional foods and healthy snacks. Presence of various biologically active compounds, such as phenolic compounds, falvonoids, phenolic acids, tannins etc and vitamin E, bases for their antioxidant and other health promoting activities. The present study is focused on the determination of total polyphenolic compounds, total flavonoids and phytochemical characterization of ethyl acetate fraction of 70% ethanol extract of almond nuts (Prunus dulcis) employing chromatographic isolation and purification, structural characterization employing 1H and 13C NMR, and mass spectrometric identification of various compounds. Materials and Methods The defatted nuts powder was extracted at room temperature with 70% ethanol and was further fractionated successively with hexane, chloroform and ethaylacetate. Folin-Ciocalteau method was used to determin the total polyphenolic compounds (1) while total flavonoids contents were quantified through Al-flavonoids complexation reaction employing UV-Visible spectrophotometer (2). The crude 70% ethanolic extract of the almond shelled seeds was analyzed through LC-MS/MS operated in negative ionization mode. Column chromatographic isolation of the ethylacetate fraction was performed over silica gel of mesh size 100-200. Elution was performed in a gradient starting with petroleum ether:ethyl acetate (9:1). Polarity of the eluent was gradually increased ending with methanol:water (4:1). Results and Discussion Total polyphenolic compounds determination experiment yielded in 0.342 mg/mL and amount of total flavonoids contents resulted were 0.026 mg/mL in the nuts extracts. Mass spectrometric analysis delivered identification of various derivatives of catechin, eriodictyol, quercetin, kaempferol and isorhamnetin including catechin dihexoside, caffeoyl-6’secologanoside and (epi)catechin-ethyl trimer were reported for the first time in almond. Isolation of stigmasitosterol3-O-β-D-glucoside and α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside was done for the first time in almond nuts. The published literature showed no such detailed study of the whole almond nuts as the main focus was on the brown almond skin. Acknowledgments This study was funded by the Projects of the International Cooperation and Exchange of the National Natural Science Foundation of China (NO. 31110103908) and the Central Asian Drug Discovery & Development Centre of Chinese Academy of Sciences. References 1. Qureshi,M.N., Stecher,G., Bonn,G.K. 2014. Determination of total polyphenolic compounds and flavonoids in Juglans regia leaves. Pakistan Journal of Pharmceutical Sciences, 27(4): 865-869. 2. Numonov,S.R., Qureshi,M.N., Aisa,H.A. 2015. Development of HPLC protocol and simultaneous quantification of four free flavonoids from Dracocephalum heterophyllum Benth. International Journal of Analytical Chemistry, doi: 10.1155/2015/503139.
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PP-164 Anti-inflammatory effect of the pomegranate peel extract in RAW264.7 cells by suppression of NF-κB and MAPK signalLing Hua Chen1,3, Xuelei Xin1,2, Hairong Ma2, H. A. Aisa1,2,*
Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences, Urumqi, Xinjiang, 830011, China2 Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences. Urumqi 830011, China 3 University of Chinese Academy of Sciences, Beijing, 100049, China.
[email protected] 1
Introduction Pomegranate, a high phenolic content fruit, belongs to the family of Punicaceae. So far, research into anti-inflammation, oxidation resistance and anti-tumor activity of the pomegranate peel have become a hot point of pharmaceutical field. However, the correlation between the pomegranate peel extract (PGE) and the anti-inflammatory properties of the dried peel of the pomegranate has not been investigated. Therefore, we attempted in this study to estimate the antiinflammatory activities of PGE in lipopolysaccharide (LPS)-stimulated RAW264.7 cells and to clarify the underlying mechanisms involved. Materials and Methods RAW264.7 cells were pre-treated with or without PGE and then stimulated with or without LPS. The effects of PGE on the cells viability were studied by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and their inhibitory activity against LPS-induced nitric oxide (NO) production screened by Griess test. The inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were measured by Western blotting and RT-PCR analysis. The productions of TNF-α, IL-6, IL-1β and MCP-1 were determined by ELISA. The activations of signaling molecules were detected by Western blotting using phosphorylation specific antibodies. Results and Discussion PGE have no significant effect on the viability of macrophages at 100 μg/ml after 24 h incubation. LPS-induced productions of TNF-α, IL-6, IL-1β, NO and MCP-1 were inhibited by PGE in a dose-dependent manner. PGE also suppressed the LPS-elevated expressions of iNOS and COX-2. Further investigations revealed that PGE inhibited LPS-induced nuclear factor-kappa B (NF-κB) activation via the prevention of inhibitory factor kappa B alpha (IκBα). We also found that PGE retains dephosphorylation of Akt and GSK-3β in response to LPS, and consequently suppressed the NF-κB activation. Additionally, PGE significantly suppressed the phosphorylation of ERK1/2, JNK and p38 in a dose-dependent manner in RAW264.7 cells. Our data suggested that PGE exerts anti-inflammatory action, at least in part, via suppressing LPSinduced activation of Akt-dependent NF-κB and MAPK signaling. Acknowledgments Thanks for financial support of Central Asian Drug Discovery and Development Center of Chinese Academy of Sciences. References 1. Negip,S., Jayaprakasha,G.K., Jena,B.S. 2003. Antioxidant and anti-mutagenic activities of pomegranate peel extracts. Food Chemistry, 80(3): 393-397.
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PP-165 Structure-activity Relationships and NMR Features of Diterpenoid Alkaloids from Xinjiang Local Plants Helimay Himit1, 4, Wetengul Kamil2, 4, Khayrulla Bobakulov3, B. Zhao2, H. Xueling1*
Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, P. R. China 2 Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, P.R. China 3 Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, 77, MirzoUlugbek str., 100170, Tashkent, Uzbekistan 4 University of Chinese Academy of Sciences, Beijing 100039, P.R. China
[email protected] 1
Introduction Diterpenoid alkaloids mainly exist in the Ranunculaceae plants of Delphinium, Aconitum and Consolida, and have very strong biological activities. Depending on the structure, diterpenoid alkaloids are classified into four categories: the C18-, C19-, C20- and double diterpenoid alkaloids. Here we report on research into diterpenoid alkaloids from three Xinjiang local plant. Materials and Methods Delphinium tianshanicum, Delphinium shawurense, Aconitum soongaricum, Varian VNMRS 600 NMR machine, Varian MR 400 NMR machine. Results and Discussion Diterpenoid alkaloids from three Xinjiang local plants Delphinium tianshanicum, Delphinium shawurense and Aconitum soongaricum were studied. Most of the isolated compounds were C19- diterpenoid alkaloids. Based on their 1 H-NMR and 13C-NMR data, the relationships of the structures and NMR data were studied: 1) for -OCH3 group, when it was attached to aliphatic carbon, the proton’s chemical shifts were in 3.0 ~ 3.4ppm, and if it was linked to the aromatic ring, the chemical shifts were changed to 3.85 ~ 3.95ppm;2) for -O-CH2-O group, two protons showed two single peaks or one broad singe peak between 4.1ppm to 5.2ppm depending on their chemical environment; and if 6-carbonyl group was exist, the chemical shifts of two single peaks were in 5.1ppm and 5.5ppm; 3) for -OCOCH3 group, chemical shifts of proton in acetate group are 1.9 ~ 2.1ppm; and if the 14-substituted group was aromatic ester, chemical shifts of the methyl group were 1.25 ~ 1.45 because of the benzene ring shielding effect. Antitumor activities of the isolated diterpenoid alkaloids showed that some compounds had good cytotoxicities against human cervical cancer HeLa cell lines and human lung adenocarcinoma A549 cell lines, and some compounds showed activities related to the relaxation of rat arteries. moreover furthThe structural characteristics of the active compounds will provide scientific basis for the future research of efficiency and low toxicity diterpenoid alkaloid compounds through structural modification. References 1. Wang F P, Chen Q H, Liu X Y. 2010.Diterpenoid alkaloids [J]. Natural Product Reports, 27: 529-570. 2. Bo Zhao, Slukhan Usmanove, Haji Akber Aisa.2014.Three new C19-diterpenoid alkaloids from Delphinium tianshanicum W. T. Wang. Phytochemistry Letters 10 189–192
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PP-166 C19-DITERPENOID ALKALOIDS FROM ACONITUM SOONGARICUM VAR. PUBESCENS Wetengul Kamil1,2,, B. Zhao1,, H. A. Aisa1*
Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China 2 University of Chinese Academy of Sciences, Beijing 100039, China
[email protected] 1
Introduction Aconitum soongaricum var. pubescens is widely distributed in Xinjiang province in China. It has been used as traditional folk medicine for the treatment of cough, rheumatism, fracture and neuralgia. During our further phytochemical investigation on this plant, three C19-diterpenoid alkaloids were isolated from the whole herb of Aconitum soongaricum var. pubescens. All of the three compounds were isolated for the first time from this plant. Materials and Methods The plant Aconitum soongaricum var. pubescens was collected from the Junggar Basin of Xinjiang, China, in August of 2011.The air-dried, ground whole plants of Aconitum soongaricum var. pubescens (10 kg) were crushed in a blender, and extracted with EtOAc. After evaporation, the crude extract was extracted exhaustively with 2 % aq. H2SO4. The filtrate was then alkalized with Na2CO3 to pH > 9 and extracted with EtOAc for each of 5 times to give the crude alkaloids (43 g) after the solvent had been evaporated. The total alkaloids (43 g) were separated using silica gel column chromatography and eluted with a gradient CHCl3–MeOH to afford eight fractions (A–H).,and three C19-diterpenoid alkaloids were obtained from its whole plants. Results and Discussion All of the three compounds Senbusine C (Fuziline) (C24H39NO7) (1), Neoline (C24H39NO6)[1] (2), and Chasmanine (C25H41NO6)[2] (3) were isolated from the Aconitum soongaricum var. pubescens ,and Their structures were identified by MS, 1D and 2D NMR techniques. OH 21
17 10
1
20
3
N 4
19
11
8 6
18
OH 15
9
5
H3CO
OCH3
16
13
7
OH 21
OH
20
3
OH
N 4
19
OCH3
SenbusineC (Fuziline)
17 10
1
H3CO
11
OH 15
9 8
6
OCH3
Neoline
7
10
1
20
3
OH
N 4
19
11
OH 15
9 8
5 6 18
H3CO
OCH3
16
13
OCH3 21
5
18
OCH3
16
13
7
OH
OCH3
Chasmanine
Acknowledgments This work was supported by the Projects of International Cooperation and Exchanges of the National Natural Science Foundation of China (Grant No. 31110103908). References 1. Tivadar K, Peter O, Szava B, et al. 2013. Identification of diterpene alkaloids from Aconitum napellus subsp. firmum and GIRK channel activities of some Aconitum alkaloids. Fitoterapia, 90:85-93. 2. Jesu s G. Dı az,* Juan Garcı a Ruiz, and Gabriel de la Fuente. 2000. Alkaloids from Delphinium staphisagria. J. Nat. Prod, 63: 1136-1139.
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PP-167 Characterization and identification of chemical components in Rosa rugosa Flowers by liquid chromatography-electrospray ionization quadrupole time-of-flight tandem mass spectrometry Sanawar Mansur1,3, Amatjan Ayubic2 ,Rahima Abdulla2 H. A. Aisa1,2*,
Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining 810008, P. R. China. 2 Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. China 3 University of Chinese Academy of Sciences, Beijing 100049, P. R. China 1
Introduction Rosa rugosa, belonging to Rosaceae family, is distributed in the temperates regions of eastern Asia including China, Japan and Korea. In Asia, it is a traditional herbal medicine for treating stomach ache, diabetes mellitus. Previously, phytochemichal studies led to the isolation of tannins, flavonoids. It is generally known that tannins and flavonoids have anti- oxidative activity. HPLC-ESI-MS/MS is now a well-established and powerful platform for rapid identification of known compounds as well as elucidation of unknown compounds in crude plant extracts, since it could give accurate mass and formulas for non-target compounds. Materials and Methods Acetonitrile (Fisher, U.S.A.) and formic acid (Merck, Germany) were used. Water used in the experiment was deionized and further purified by the Milli- Q Plus water purification system (Millipore Ltd., USA). Dried and finely powdered Rosa rugosa (5g) were extracted with 60% aqueous ethanol (100 mL) at room temperature under reflux 1 hour. The solution was filtered through a 0.22 mm filter before LC-MS analysis. Results and Discussion A total of 45 compounds including tannins, their related compounds and flavonoids were identified or partially characterised according to accurate mass and the characteristic fragments at low and high CE. This study established that the LC-ESI-QTOF- MS method is efficient for identifying, and could be the basis for the comprehensive quality control of Rosa rugosa. Acknowledgments and References This work was supported by the Key Deployment Projects of the Chinese Academy of Sciences (Grant No. KSZDEW-Z-004-04).
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PP-168 The Essential Oil Composition and Antimicrobial Activity of Nepeta cilicica Boiss. ex Benth. Gökalp İşcan1, 2, Yavuz Bülent Köse3, Fatih Göger1, Betül Demirci1
Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470 Eskisehir, Turkey Yunus Emre Vocational School, Anadolu University, 26470 Eskisehir, Turkey 3 Department of Pharmaceutical Botany, Faculty of Pharmacy, Anadolu University, 26470 Eskisehir, Turkey 1 2
The genus Nepeta (Lamiaceae) comprises 280 species distributed in Europe, Asia and Africa. It is represented in Turkey by 33 species and altogether 44 taxa, 22 of them are endemic [1, 2]. Some of these species are widely used in folk medicine for their medicinal properties such as diuretic, diaphoretic, antitussive, antispasmodic, anti-asthmatic, febrifuge, emmenagogue, sedative and stomachic. Biological effects are usually attributed to nepetalactones especially found in Nepeta oils [3]. Aerial parts of Nepeta cilicica Boiss. ex Benth. (Lamiaceae) collected from İçel province in June’2014 were hydrodistilled to obtain an essential oil that was then analysed simultaneously by GC-FID and GC/MS systems. Thirty compounds representing 92% of the oil were characterized. Caryophyllene oxide (28.2%), β-caryophyllene (8.9%), spathulenol (4.2%) were found as major components. Anticandidal and antibacterial effects of the oil and methanolic extract of aerial parts of N. cilicica were evaluated against 24 pathogenic Candida and bacteria strains by using CLSI M27-A2 and M7-A7 protocols respectively. The oil and the extract showed good inhibitory effects against C. tropicalis at the concentrations of 45 µg/ml. REFERENCES 1. İşcan, G., Köse, Y.B., Demirci, B., Başer, K.H.C., The Anticandidal Essential Oil of Nepeta transcaucasica Grossh., Chemistry and Biodiversity, 8 (11), 2144-2148, 2011. 2. Kordali S., Tazegül, A., Çakır, A., Phytotoxic Effects of Nepeta meyeri Benth. Extracts and Essential Oil on Seed Germinations and Seedling Growths of Four Weed Species, Rec. Nat. Prod. 9:3 404-418, 2015. 3. Başer, K.H.C., Kırımer, N., Kürkçüoğlu, M., Demirci, B., Essential Oils of Nepeta Species Growing in Turkey, Khim.Prir.Soedin, 4, 291-293 (2000). Chem.Nat.Prod., 36, 356-359 (2000). 4. CLSI (NCCLS) M7-A7, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard, Seventh Edition, 2006. 5. CLSI (NCCLS) M27-A2 Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard— Second Edition; 2002.
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PP-169 Affinity material for esculin based on imprinted βeta-cyclodextrin polymers prepared in ionic liquid Li Ma, Xiu-Yuan Li, Yan-Ping Huang, Zhao-Sheng Liu*
Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin 300070, China
[email protected]
Introduction Esculin (EN) is one of the main active components of the Chinese traditional medicine Cortex Fraxini, showing many kinds of biologic activities. However, to obtain esculin of high purity is a main challenge due to the high complexity of the natural product. Molecularly imprinted polymers (MIPs) have become increasing attractive in the separation and purification of active components. The aim of this study was to develop a novel MIPs suitable for recognizing EN in polar medium. β-cyclodextrin (β-CD) was chosen as functional monomer since unique host-guest complexes with hydrophobic molecules and polymers can be formed. Materials and Methods EN (≥98 %) was purchased from Xibao Co. Ltd. (China). β- CD and hexanethylene diisocyante were supplied by J&K, Chian. [BMIM]BF4 was the product of Chengjie Co. Ltd. (China). Other analytical reagents were from Jiangtian Chemical Reagent Co. Ltd. (China). General synthetic procedure of MIPs was as fellows. EN and β-CD were were firstly dissolved with 5 mL mixture of DMSO and [BMIM]BF4 (4:6, v/v) and then 2.5 mL HMDI crosslinker was added. The mixture was kept at 65C for 2 h. 0.20
MIP NIP
Qe (mmol/g)
0.15
Fig. 1 Absorption isotherms of EN on MIPs and NIPs in ethanol. V=2.0 mL, C0 = 0 - 10 mmol/L, t=24 h, 10 mg of the polymers.
0.10
0.05
0.00
0
1
2
3
4
5
6
7
Ce (mmol/L)
8
9
10
Results and Discussion The imprinting performance and binding property of EN-MIP was evaluated by equilibrium binding experiments in ethanol. When the molar ratio of EN to β-CD was 1:10, the resultant MIPs exhibited higher binding capacity for EN than nonimprinting polymers (NIPs) in ethanol with imprinting factor of 2.19 (Fig. 1). Scatchard analysis of MIPs suggests that there are two classes of binding sites during the MIP’s recognition of EN. Acknowledgments This work was supported by the Hundreds Talents Program of the Chinese Academy of Sciences and supported by the National Natural Science Foundation of China (grant No. U1303202). References 1. Sueyoshi, Y., Fukushima, C., Yoshikawa, M. 2010. Molecularly imprinted nanofiber membranes from aimed for chiral separation. Journal of Membrane Science, 357: 90-97.
cellulose acetate
2. Panahi, R., Vasheghani, E., Shojaosadati,SA. 2007. Separation of L-lysine from dilute aqueous solution using molecular imprinting technique. Biochemical Engineering Journal, 35: 352-356.
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PP-170 CHEMICAL CONSTITUENTS OF EUPHORBIA SOONGARICA BOISS. Jie Gao1,3, Qi-Bin Chen2,3, Ruxian Ruzimamat1,3, Haji Akber Aisa *,1,2
The Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China 2 State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China 3 University of Chinese Academy of Sciences, Beijing 100039, China
[email protected] 1
Introduction Euphorbia soongarica Boiss., a perennial herb plant of Euphorbiaceae family, is mainly distributed in northwestern China, central Asia, western Siberia and Mongolia. It has been widely used in folk of Xinjiang of China as purgative, apocenosis and discussive (Editorial Committee of Flora of China, 1997). There are only few reports concerning the chemical constituents of this plant (Lin et al., 2008; Shi et al., 2009), and the diterpenoid constituents of this plant have not been reported. Materials and Methods The whole plant of E. soongarica was collected in Jinghe, Xinjiang, P. R. China in 2013.The air-dried whole plant of E. soongarica (10 kg) was extracted with acetone at room temperature. The acetone extract (600 g) was suspended in cyclohexane and partitioned with CH3CN to yield the CH3CN soluble extract (140 g), which was then fractionated by silica gel column chromatography (CC, 100−200 mesh) with a petroleum ether−EtOAc gradient (100:1 to 0:1) to afford 11 fractions. Fraction 7 was subjected to silica gel and Sephadex LH-20 CC and semi-preparative HPLC to afford seven compounds. Results and Discussion One diterpene (helioscopinolide B), one sesquiterpene (litseachromolaevanes B), one chalcone (7,9,4’-trihydroxy-5methoxy-8-methylchalcone), two coumarins (isofraxidin and 5,6,7-trimethoxycoumarin ) and two phthalates (phthalic acid isodibutyl ester and phthalic acid dibutyl ester) were isolated from the whole plant of E. soongarica for the first time. Their structures are shown in Figure 1.
Figure 1. Structures of the compounds isolated from Euphorbia soongarica Boiss.
Acknowledgments This work was supported by the Projects of International Cooperation and Exchanges of the National Natural Science Foundation of China (Grant No. 31110103908), the Projects of International Science & Techology Cooperation of the Xinjiang Uyghur Autonomous Region (Grant No. 20126023), and the Central Asian Drug Discovery & Development Centre of Chinese Academy of Sciences.
References 1. Editorial Committee of Flora of China, Chinese Academy of Sciences, 1997. Flora of China. Science Press, Beijing, vol. 33, pp105. 2. Lin,J., An,N., Liu,C.Y., Xu,L.Z. 2008. Chemical constituents from roots of Euphorbia songarica. Chinese Traditional and Herbal Drugs, 39: 497–499. 3. Shi,X.H., Luo,J.G., Kong,L.Y. 2009. Coumarin glycosides from Euphorbia soongarica (Boiss). Journal of Asian Natural Products Research, 11: 49–53.
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240
PP-171 Study on Anti-Vitiligo activity of Kaliziri flavonoids A. Tuerxuntayi1, Maidina2, H. A. Aisa2*
School of Life Science, Xinjiang Normal University, Urumqi 830054, China The Key Laboratory of Chemistry of Plant Resources in Arid Regions, CAS Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, Xinjiang, China
1 2
ıntroductıon Vitiligo is an acquired, progressive, multifactorial, depigmentation disorder characterized by the appearance of circumscribed white macules in the skin caused by chronic, progressive loss of functional melanocytes in the epidermis. Kaliziri [Vernonia anthelmintica (L.)Willd. ] is a plant that only grows in high-altitude areas of southern Xinjiang. Kaliziri seeds are used as febrifuge for treating skin diseases like leukoderma (vitiligo) in traditional therapy. Our preliminary research results proven that melanin activity interesting extracts from Kaliziri. We obtained several fractions from extracts. Every fraction was tested for tyrosinase activity. We isolated butin, butein, isocarthamidin and liquirtigeninis from Kaliziri seeds and examined the cytoxicity of four flavonoids by MTT assay; investigated their effects on tyrosinase activity and melanin content on B16 melanoma cells. The results showed that: butin, butein and liquirtigeninis showed dose-dependent activity in B16 melanoma cells. Cooperativity may exist among these compounds. The continuing study is underway.
Acknowledgement Joint Funds of the National Natural Science Foundation of China (GrantNo. U1203203),Key Research Program of the Chinese Academy of Sciences (GrantNo. KSZD-EW-Z-004). REFERENCE 1. Corre, S., Galibert, M.D. Pigment Cell & Melanoma Research., 2005,18, 337–348.
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PP-172 Identification of chemical components in the low-polarity part of Vernonia anthelmintica extract by HPLC-MS/MS Ablikim Kerim1, Ablajan Turak
, Qiao-ying Lv 2, Rahima Abdulla 2,,3, H. A. Aisa 2, *
2, 3
School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China; State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China 3 University of Chinese Academy of Sciences, Beijing 100039, China *
[email protected] 1 2
Introduction In our previous research, the 40% ethanol extract part of Vernonia anthelmintica seeds was the effective part and showed significant tyrosinase activity. The constituents of the high-polarity part were identified according to standard compounds. HPLC-MS/MS was used to confirm the low-polarity chemical constituents of the active extract. Materials and Methods The air-dried seeds (10 g) of V. anthelmintica were extracted with 40% ethanol three times at 80°C. The extract was concentrated under reduced pressure and then suspended in water, and chromatographed on a HPD-300 macroporous resin column and eluted with water, 50% ethanol, and 95% ethanol. The 95% eluted part was analysed using a QSTAR Elite LC-MS/MS system. Results and Discussion According to precursor ion and product ion peaks in the TIC, ten compounds were identified (Fig. 1).
Fig.1 Total ion chromatogram in positive ESI mode
The ten compounds, including four sesquiterpenoids, four flavonoids, one coumarin and one caffeoylquinic acid are listed in Table 1. Table 1. Identification of chemical components in the low-polarity part of V. anthelmintica extract. No.
tR (min)
MW
Precursor ion (m/z)
Product ion (m/z)
Identification
1
6.75
352
353.0597
335.0749, 163.0398
caffeoylquinic acid
2
7.73
378
379.1335, 401.1136
277.1035
vernodalinol
3
9.16
272
273.0734
135.0382, 137.0190
butin
4
9.65
392
393.1492, 415.1285
291.1209
vernodalol
5
10.81
380
381.1867, 403.1672
279.1542
vernofultanin or isovernofultanin
6
12.14
406
407.1654
305.1367
vernodalol
7
12.54
288
289.0655
271.2572, 153.0136
eriodictyol
8
14.00
348
349.1548, 371.1391
183.1118, 165.0655
3,4,2′,4′,5′,α-hexahydroxy-6′methoxy -2′-methylchalcone
9
14.78
316
316.0613
166.9900
isorhamnetin
10
15.50
220
221.0714
163.0350, 152.0572
5,7-dimethoxy-4-methylcoumarin
Acknowledgment This work was financially supported by the Funds for International Cooperation and Exchange of the National Natural Science Foundation of China (Grant No. 31110103908).
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PP-173 Chemical Constituents of Silene arenarioides Desf. And its Biological Activity Lynda Golea1,2, Hamada Haba1, Cathrine Lavaud3, Mohammed Benkhaled1
Laboratoire de Chimie et Chimie de l ;Environnement (L.C.C.E), Département de Chimie, Faculté des Sciences, Université de Batna, Batna 05000,Algeria 2 Departement de science de la matière, université de khenchela, khenchela 40000, Algerie 3 UMR CNRS 6229, Institut de Chimie Moleculaire de Reims, BP 1039, 51097 Reims Cedex 2, France.
[email protected] 1
The genus Silene is the most representative of the caryophyllaceae family for their rich content in secondary metabolites; saponins, flavonoids and flavonoids glycosides, phytoecdysones, oligosaccharides have been isolated and identified. The Silene genus represented by about 700 species in the temperate region of the word, the main concentration of spcies is Europe, Asia and North Africa. Three known compounds 1-3 were isolated from the aerial parts of Silene arenarioides Desf. by using different chromatographic methods. The structures of the isolated compounds were determined as stigmasterolglycoside (1), Soyacerebroside (2), maltol glycoside (3). The structures of the isolated compounds were determined by using the NMR (1H-NMR, 13C-NMR, COSY, HSQC, and HMBC) techniques and mass spectroscopy. The antimicrobial and antioxydant activities of the different extracts and compound (3) have been reported. 5''
4'' 3''
6'' 1'' 7"
O 6'
HO HO 3'
4' 2'
HO
2''
19
O
O
O
H3C
3
5 OH
2
6'
4'
HO
6
O
7
1
H OH
1'
3
22
18 12
O 5'
2
5'
H
3'
H
H 2'
O
OH
O
H
8
4
5
24 23
17 13
9 10
3
1'
11
20
14
15
7 6
O
1'
1
16'
2'
NH O
O 1''
HO
1
OH
2
3
OH
4
8
5
9
2
OH
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26 25 27
16
OH
HO
29
28 21
18
PP-174 Separation of oleanolic acid from natural plant extracts using new type of molecularly imprinted polymers Chen Zhang, Xiu-Xiu Chen, Zhao-Sheng Liu*
Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin 300070, China
[email protected]
Introduction Oleanolic acid (OA) is an important triterpene possessing many important biological activities, such as antitumor, hepatoprotective and hypolipidemic effects (Somova et al. 2003)[1]. Difficult to be synthetized due to its complicate structure, OA is obtained mainly from plant extracts (Pollier et al. 2012)[2]. Because the conventional methods for OA separation are complex and time-consuming, it is necessary to develop an efficient approach for purification of OA. Molecularly imprinted polymers (MIPs) represent designing materials that possess the molecular recognition properties for targeted molecules (Whitcombe et al. 2014)[3], and are commonly used for solid-phase extraction (SPE) in the analysis of biological and environmental samples (Boyacı et al. 2015)[4]. The aim of this study was to develop a novel MIPs to purify OA from natural product. Materials and Methods Molecularly imprinted monolith was prepared in situ within the confines of a stainless-steel chromatographic column tube (100 mm×4.6 mm i.d.) using OA as template, 4-vinylpyridine as functional monomer, ethylene glycol dimethacrylate as crosslinker monomer, a ternary mixture of polymethylmethacrylate solution in chloroform, dimethyl sulfoxide and 1-butyl-3-methylimidazolium tetrafluoroborate as porogen. For application to SPE, 200 mg of MIPs was packed into a 3-mL polypropylene column. The MISPE column was conditioned with 10 mL of MeOH before use. After sample loading, the column was washed by 5mL MeOH/H2O (50/50, v/v) and MeOH/HAc (90/10, v/v), respectively. Results and Discussion The influence of template-monomer (T/M) molar ratio on the imprinting factor of the resultant MIP monoliths was studied and the optimum ratio of template/functional monomer was 1:8 (Fig. 1). In present imprinting system, 4-vinylpyridine was found to be the best functional monomer to achieve the greatest imprinting effect (Fig. 2). The imprinting factor of the resulting MIP monolith obtained was up to 2.97 (Fig. 3). The OA MIP can be used to as SPE to purify OA from natural plant extracts with mean recoveries of 72.32% (Fig. 4). Acknowledgments This work was supported by the National Natural Science Foundation of China (grant No. U1303202). References 1. Somova,L.O., Nadar,A., Rammanan,P., Shode,F.O. 2003. Cardiovascular, antihyperlipidemic and antioxidant effects of oleanolic and ursolic acids in experimental hypertension. Phytomedicine, 10: 115-121. 2. Pollier,J., Goossens,A. 2012. Oleanolic acid. Phytochemistry, 77: 10-15. 3. Whitcombe, M.J., Kirsch,N., Nicholls,I.A. 2014. Molecular imprinting science and technology: A survey of the literature for the years 2004–2011. Journal of Molecular Recognition, 27: 297-401. 4. Boyacı,E., Rodríguez-Lafuente,Á., Gorynski,K., Mirnaghi,F., Souza-Silva,É.A., Hein,D., Pawliszyn,J. 2015. Sample preparation with solid phase microextraction and exhaustive extraction approaches: Comparison for challenging cases. Analytica Chimica Acta. 873: 14-30.
IF
IF
2.4
0 8
MAA
4-VP
AM MIP NIP
6
k
0.8 0.0
2 1
1.6
8000
Fig.2
3
4
Solvent peak
6000
OA
4000 OA 2000
NIP
MIP
0
2
1:4 1:6 1:8 1:10 1:12 Template: Functional monomer (molar: molar)
Fig. 1 Imprinting factors of MIPs with the different ratio of template to functional monomer
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20000 Solvent peak
Fig.3
Absorbance (mV)
4
Fig.1
Absorbance (mV)
3.2
Fig.4
16000 OA
12000
After MISPE
8000
OA
Solvent peak
4000
Practical sample
0 MAA
4-VP
0
AM
10
15
20
25
30
Time (min)
Type of functional monomer
Fig. 2 Imprinting factors of MIPs with the different ratio of different type of functional monomer
5
Fig. 3 Chromatograms of the OA on imprinted monolith and non-imprinted monolith
244
0
5
10
15
Time (min)
Fig. 4 Chromatograms of the samples of olive extraction
PP-175 PHENOLIC COMPOUNDS OF CAMPANULA BETULIFOLIA C. KOCH (ENDEMIC) FROM TURKEY Nilgun Ozturk1, İIham Eroz Poyraz2, Fatih Gulbag3, Serdar Erken3, M. Ercan Ozzambak4
Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, Eskisehir TURKEY Anadolu University, Faculty of Pharmacy, Department of Pharmacetical Botany, Eskisehir TURKEY 3 Republic of Turkey Ministry of Food, Agriculture and Livestock-Atatürk Horticultural Central Research Institute Yalova TURKEY 4 Ege University, Faculty of Agriculture, Department of Horticulture Izmir TURKEY
[email protected] 1 2
The genus Campanula L. (Campanulaceae) is represented by 133 species (122 taxa, 65 endemic) in Turkey and 300 species in the World. Campanula (bell flower) are used mostly as ornamentals. However, a number of species have been used in folk medicine. They are used to treat epilepsy, nervous diseases, coughs, headache, rheumatism, and inflammation, in Russia and Italy (Duke 2002). Campanula betulifolia C.Koch is an endemic plant grown in Turkey (Davis 1978). In this study, the methanol extracts from aerial parts of Campanula betulifolia C. Koch, collected from Erzurum, Turkey, were screened for its phytochemical properties. The amount of total phenols were analyzed with the FolinCiocalteu reagent. Gallic acid was used as a standard compound and the total phenols were expressed as mg/g gallic acid equivalents (Singleton and Rossi (1965)). Soluble phenolic acids were extracted with methanol and a tentative quantification was performed by RP- HPLC. Chromatographic analysis of the extracts was carried out by a gradient elution (A: methanol:water:formic acid (10:88:2 v/v/v); B: methanol:water:formic acid (90:8:2 v/v/v) as it was reported elsewhere (Ozturk et al. 2007). To the best of our knowledge, this is the first study on C. betulifolia phenolics. tr-Cinnamic (10.88 mg/100 g plant), ferulic (4.66 mg/100 g plant), and vanillic (2.95 mg/100 g plant) acids were determined to be the major phenolics in the methanol extract. ACKNOWLEDGMENT This study has been supported by TUBITAK-Scientific and Technological Research Projects Funding Program (Project No: 112O060). REFERENCES 1. Davis,P.H., Mill,R.R., Tan,K. 1978. Flora of Turkey and the East Aegean Islands, 6, Edinburgh University Press, Edinburgh, UK 2. Duke, J., 2002. Handbook of Medicinal Plants, CRC Press LLC, p.67, USA. 3. Ozturk,N., Tuncel,M., Tuncel,N. 2007. Determination of phenolic acids by a modified HPLC: Its a application to various plant materials. Journal of Liquid Chromatography Related Technology, 30: 587-596. 4. Singleton,V.L., Rossi,J.A.Jr. 1965. Colorimetry of total Phenolics with phosphomolybdic-phosphotungstic acid reagents. American Journal of Enology and Viticulture, 16: 144-158.
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PP-176 Comparison and Characterization of Sideritis caesarea (SC) Duman, Aytac & Baser Essential Oil Constituents Collected from Different Localities and in Periods Tuğba Günbatan1, Betül Demirci2, İlhan Gürbüz1*, Ayşe Mine Gençler Özkan3
Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, 06330, Ankara, Turkey Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskişehir, Turkey 3 Department of Pharmaceutical Botany, Faculty of Pharmacy, Ankara University, 06100, Ankara, Turkey
[email protected] 1 2
Turkey possesses high number of Sideritis species (44 species), and it is widely used with different ethnopharmacological purposes (Duman et al., 2005; Gonzalez-Burgos et al., 2011). They mainly include diterpenes, flavonoids and essential oil (Ertan et al, 2001; Gonzalez-Burgos et al., 2011: Kırımer et al, 1999; Tuna al., 2004). In this study, essential oil content of Sideritis caesarea H. Duman, Aytaç & Başer collected in different dates and localities were investigated (Duman, Başer, Aytaç, 1998). Aerial parts of Sideritis caesarea H. Duman, Aytaç & Başer were collected form 3 different localities in Kayseri (Turkey); Dayıoluk Village [Sarız Town, in 04.07.2013 (A) and 07.07.2014 (B)], Kaynar Burg [Pınarbaşı Town, in 16.07.2013 (C)] and Şirvan Mountain [Pınarbaşı Town, in 16.07.2013 (D)]. Each samples were hydrodistilled for 3 hour using a Clevenger-type apparatus to produce a small amount of essential oil which was trapped in n-hexane. The essential oils obtained were analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS), simultaneously. Major components of essential oils obtained from four samples were determined to be the same but their ratios were different. Major volatile components of samples A and B were hexadecanoic acid (19.7% and 14.6 %, resp.), caryophyllene oxide (6.7% and 8.3%, resp.), β-caryophyllene (6.5% and 11.5%, resp.), spathulenol (3.4% and 4.2%, resp.). For samples C and D, caryophyllene oxide (13.7% and 20.2%, resp.), hexadecanoic acid (8.5% and 20.5%, resp.), spathulenol (6.1% and 3.9%, resp.) and β-caryophyllene (5.5% and 12.6%, resp.) were the major components of essential oils. Acknowledgements This study was financially supported by The Scientific and Technological Research Council of Turkey – TUBİTAK (Project no: SBAG-112S581). References 1. Duman, H., Kırımer, N., Ünal, F., Güvenç, A., Şahin, P. 2005. Türkiye Sideritis L. türlerinin revizyonu. TBAG-1853 (199T090). 2. Gonzalez-Burgos, E., Carretero, M.E., Gomez-Serranillos M.P. 2011. Sideritis spp.: Uses, chemical composition and pharmacological activities-A review. Journal of Ethnopharmacology, 135: 209–225. 3. Duman, H., Başer, K.H.C., Aytaç, Z. 1998. Two new species and a hybrid from Anatolia. Turkish Journal of Botany, 22: 51-55. 4. Kırımer, N., Tabanca, N., Tümen, G., Duman, H., Başer, K.H.C. 1999. Composition of the Essential Oils of Four Endemic Sideritis Species from Turkey, Flavour and Fragrance Journal, 14: 21-425. 5. Ertan, A., Azcan, N., Demirci, B., Başer, K.H.C. 2001. Fatty Acid Composition of Sideritis Species, Khimiya Prirodnykh Soedinenii, 4: 259-261. Chemistry of Natural Compounds 37: 301-303 (2001). 6. Tunalıer, Z., Koşar, M., Öztürk, N., Başer, K.H.C., Duman, H., Kırımer, N. 2004. Antioxidant properties and phenolic composition of Sideritis species, Chemistry of Natural Compounds 40:206-210.
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PP-177 Antimicrobial, Antioxidant and Composition of the Essential Oils from Leaves and Aerial parts of Artemisia lehmaniana Growing in Iran Fateme Aboee-Mehrizi1*, Abdolhossein Rustaiyan2, Ali Zare2,
Department of Medicine, Islamic Azad University, Yazd Branch, P.O. Box 89195-155, Yazd, Iran Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
[email protected]
1 2
The chemical composition of the essential oils obtained from aerial parts and leaves of the flowering stage of plants of Artemisia lehmaniana was analyzed by gas chromatography mass spectrometry (GC-MS); 97.95, and 95.88% compounds were identified in the aerial parts and leaf oils, respectively. The antimicrobial activities of essential oil of Artemisia lehmaniana were obtained from the aerial parts by screening against Gram-positive, Gram-negative bacteria, and fungi. The plant oil showed a mild antibacterial activity against the tested microorganisms. Among bacterial strains tested Escherichia coli was found more sensitive to essential oil (MIC of 32μg/mL). The antioxidant activities were evaluated by using 2,2 diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assays (IC50: 3.7 mg/mL). Essential oil of this plant showed high antioxidant activities. DPPH assay result was in good correlation with the total phenolic contents of the plant, measured by the Folin-Ciocalteau assay: (R2 = 0.920, p < 0.0001).
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PP-178 CHEMICAL CONSTITUENTS OF THE ROOTS OF ANACYCLUS PYRETHRUM (L) DC. Qi-Bin Chen1,2, Gulnar Kasim 1, H. A. Aisa *,1
The Key Laboratory of Plant Resources and Chemistry of Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. China 2 University of Chinese Academy of Sciences, Beijing 100039, P. R. China
[email protected] 1
Introduction Anacyclus pyrethrum (L) DC. belongs to the Asteraceae family. The roots of A. pyrethrum has been widely used as paralysis, hemiplegia, cephalalgia, epilepsy and rheumatism treating in Asian country (Prajapati et al., 2003). It has also been used as aphrodisiac in Uyghur traditional medicine. Although, the chemical constituents of the roots of A. pyrethrum are still rarely reported. In order to reveal the bioactive chemical substances and discover novel compounds, we conducted an investigation on the roots of A. pyrethrum. Materials and Methods The roots of A. pyrethrum was purchased from Pakistan in 2013. The powdered roots (2 Kg) was extracted with 70% EtOH at 85 oC to afford an EtOH extract (500 g). The EtOH extract was extract with petroleum ether and ethyl acetate respectively to give an EtOAc extract (24.5 g). The EtOAc extract was separated by silica gel column chromatography (100−200 mesh, 11×50cm, ) into 20 fractions using a petroleum ether−EtOAc gradient (50:1 to 0:1). Compound 1 and 2 were isolated from Fr.8 and Fr.13 by CC method, respectively. Compound 3, 4 and 5 were obtained from Fr.14 by further CC separation. Results and Discussion Two new quinoline alkaloids (3, 5) together with three known N-alkylamide alkaloids (1, 2, 4) (Sharma et al., 2013) were obtained from the roots of A. pyrethrum. Their structures are shown as follows.
References 1. Prajapati,N.D., Purohit,S.S., Sharma,A.K., Kumar,T., 2003. A Handbook of Medicinal Plants: A complete source book. Agrobios, India, pp. 43—44. 2. Sharma,V., Boonen,J., Spiegeleer,B.D., Dixit,V.K., 2013. Androgenic and spermatogenic activity of alkylamide-rich ethanol solution extract of Anacyclus pyrethrum DC. Phytotherapy Research, 27: 99—106.
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PP-179 FAME COMPOSITION OF FOUR ORNITHOGALUM L. SPECIES GROWN IN TURKEY G. Renda1*, G. Tosun2, B. Yaylı1, N. Yaylı1 1 Karadeniz Technical Univ., Faculty of Pharmacy, Department of Pharmacognosy, Trabzon, Turkey. 2 Karadeniz Technical Univ., Faculty of Arts and Sciences, Department of Chemistry, Trabzon, Turkey.
[email protected]
Introduction The genus Ornithogalum L. (Liliaceae) includes about 150 species distributed in the World and recorded by 34 species in Turkish flora (Davis et al., 1988). The bulbs of the plant have medical and economic values, also O. sigmoideum bulbs are consumed as food and sold in local markets in Turkey (Baytop, 1999). The aim of this work was to identify comparative fatty acid methyl esters (FAME) in the methanolic extracts of the bulbs and the aerial parts of four Ornithogalum species by a gas chromatographic and mass spectroscopic method. Materials and Methods The samples of the aerial parts and bulbs of Ornithogalum sigmoideum Freyn & Sint (OS), Ornithogalum orthophyllum Ten. (OO), Ornithogalum oligophyllum E.D.Clarke (OL) Ornithogalum umbellatum L. were collected from Trabzon and Ordu (in March, April, May and June 2013 respectively). Dried and powdered plant materials were extracted with methanol. All of the methanolic extracts were heated with 5% sodium hydroxide solution. Aqueous mixture was neutralized and extracted with hexane-diethyl ether (1:1 v/v). The organic layer was separated evaporated. Each sample dissolved in methanol and cooled in ice bath, BBr3 was added and extracted by hexane. The hexane layers were filtered. The organic solvent was removed under reduced pressure on a rotary evaporator to give fatty acids methyl esters (FAME) and other lipids (Dembitsky et al., 2010; Kılıç et al., 2011). Results and Discussion The major FAME of the aerial parts of O. orthophyllum, O.oligophyllum and O. umbellatum was hexadecanoic acid methyl ester (50.9%, 52.1% and 52.6% respectively). The main component of O. sigmoideum was 1,4 benzene dicarboxylic acid dimethyl ester (66.8%). The GC-FID-MS analysis of the bulbs of the all three species (O. oligophyllum, O.sigmoideum and O. umbellatum) allowed the identification of 4-oxo pentanoic acid methyl ester (57.7%, 32.1% and 35.3%, respectively) and hexadecanoic acid methyl ester for the bulbs of O. orthophyllum (57.6%) as the major component as well. Acknowledgments This research was supported by the Scientific Research Foundation of the Karadeniz Technical University (Project Number 8960). References 1. Baytop, T. 1999. Türkiye’de Bitkilerle Tedavi 2. Baskı, İstanbul: Nobel Tıp Kitabevi.
2. Davis, P.H., Mill, R.R. and Tan, K. 1988. Flora of Turkey and the East Aegean Islands, Vol.10 (supplement I).(s. 223). Edinburgh: Edinburgh University Press. 3. Dembitsky, V.M., Terent’ev, A.O., Levitsky, D. O. 2010. Amino and Fatty Acids of Wild Edible Mushrooms of the Genus Boletus. Rec. Nat. Prod. 4:4, 218-223. 4. Kılıç, C.S., Aslan, S., Kartal, M., Coskun, M. 2011. Fatty Acid Composition of Hibiscus trionum L. (Malvaceae). Rec. Nat. Prod. 51: 65-69.
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PP-180 Volatile Compounds of Roots, Aerial Parts and Flowers of Ferulago pachyloba (Fenzl) Boiss. (Apiaceae) Growing in Turkey and Determination of Their Antimicrobial Activities via Bioautography Method Karakaya S1, Kılıç C.S1, Demirci B2*, Demirci F2
Ankara University, Faculty of Pharmacy, Department of Pharmaceutical Botany, 06100 Tandoğan, Ankara, Turkey Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470, Tepebaşı, Eskişehir, Turkey
Ferulago W. Koch. (Apiaceae) genus is represented by approximately 50 taxa throughout the world (1). Ferulago species are known as “Çakşır” or “Çağşır” in Turkey and according to recent records, the genus is represented by 35 taxa in Turkey, 18 of which are endemics (2). Volatile components from roots, aerial parts and flowers of Ferulago pachyloba (Fenzl) Boiss., an endemic species (Apiaceae) were obtained by hydrodistillation and analyzed by GC and GC-MS and main components were found to be (Z)-β-ocimene (27.5), sabinene (25.8) for the flowers; hexadecanoic acid (15.4), (E)-2decenal (14.3) for the roots and sabinene (16.0), (Z)-β-ocimene (15.1) for the aerial parts. Antimicrobial activity study via bioautography method was performed against three different microorganisms, Pseudomonas aeruginosa ATCC 13388, Staphylococcus aureus ATCC BAA 1026 and Candida albicans ATCC 24433 and showed that volatile samples obtained from the herba and roots were active against Staphylococcus aureus ATCC BAA 1026 and showed good inhibition; however volatile components obtained from the flowers showed weak activity. The volatile sample obtained from the roots was also active against Candida albicans ATCC 24433, but its inhibition zone was less visible than the zone obtained for Staphylococcus aureus. However no volatile sample was active against Pseudomonas aeruginosa ATCC 13388. References 1. Troia A. et al. (2012). Morphological, karyological and taxonomic remarks on Ferulago nodosa (L.) Boiss. (Apiaceae). Plant Biosystems. 146: 330-337. 2. Güner A. (2012). Türkiye Bitkileri Listesi (Damarlı Bitkiler). 1. Baskı. İstanbul, Türkiye: Nezahat Gökyiğit Botanik Bahçesi Yayınları, Flora Dizisi 1.
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PP-181 Composition of the essential oil of endemic Stachys sericantha from Turkey Ayla Kaya 1*, Betül Demirci 2, Süleyman Doğu 3, Muhittin Dinç 3
Department of Pharmaceutical Botany, Faculty of Pharmacy, Anadolu University, 26470 Eskisehir, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470 Eskisehir, Turkey 3 Department of Biology, Ahmet Keleşoğlu Faculty of Education, Necmettin Erbakan University, 42090 Konya, Turkey *
[email protected] 1 2
Introduction The genus Stachys L., one of the largest genera of Lamiaceae, includes about 300 species of annuals and perennials occurs in all parts of the world, except for Australia and New Zealand (Bown, 1995). Stachys sericantha P.H. Davis, an endemic plant and Mediterranean element, is perennial 35-70 cm long, corolla purple-pink coloured, 13-16 mm. It grows on stone slopes, in Pinus brutia woods of southwest Anatolia and the flowering time is from June to July (Bhattacharjee, 1982). Plant is locally known as “dikenli çay” in the regions where it grows (Güner et al., 2012). Materials and Methods Plant was collected during the flowering period from Antalya province of Turkey. The voucher specimens are kept at the Herbarium of the Department of Biology, Necmettin Erbakan University, Konya, Turkey. The essential oil from aerial parts of S. sericantha was isolated by steam distillation and analysed by gas chromatography (GC) and gas chromatographymass spectrometry (GC-MS), simultaneously. Results and Discussion The yield of essential oil of S. sericantha is small amount. The major components were found as hexadecanoic acid 23.7%, dodecanoic acid 11.3%, caryophyllene oxide 10.7%, tetradecanoic acid 4.3% and β-caryophyllene 4.2%. The essential oil compositions of the Stachys genus have been well documented in the literatüre. The main components of the essential oil of the species were observed to be germacrene D, caryophyllenes, cadinene, spathuleneol and caryophyllene (Gören, 2014). References 1. Bhattacharjee, R. 1982. Stachys. In: Davis, PH et al. (eds), Flora of Turkey and the East Aegean Islands, Edinburgh University Press, Edinburgh,Vol 7, pp. 214-215. 2. Bown, D. 1995. The herb society of America encyclopedia of herbs and their uses, Dorling Kindersley, London. 3. Gören, A. C. 2014. Use of Stachys Species (Mountain Tea) as Herbal Tea and Food. Rec. Nat. Prod. 8(2):71-82. 4. Güner, A., Aslan, S., Ekim, T., Vural, M., Babaç, MT. 2012. Türkiye Bitkileri Listesi (Damarlı Bitkiler), Nezahat Gökyiğit Botanik Bahçesi ve Flora Araştırmaları Derneği Yayını, İstanbul.
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PP-182 The GC-MS Analysis of Xinjiang Almond oil based on Fatty Acids Ajigu Abudurexiti1, 2, Muhetaer Tuerhong 2, H. A. Aisa 1, 2 *
State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China 2 College of Chemistry and Environmental Science, Kashgar University, Kashgar 844006, China
[email protected] 1
Introduction Amygdalus communis L., distributes in Central Asia, West Asia, America California and South Xinjiang of China. The seeds of Almond, belonging to Rosaceae and Prunoideae, contain fatty oil, protein, starch, amino acids, flavonoid and polyphenols.The seeds of Almond have antioxidant activity, anticancer, reducing cholesterol, enhancing immune power and protecting liver. In the previous study, fats and oil from the seeds of Almond, based on the orthogonal experimental, was extracted by supercritical CO2 extraction technology. The fatty acids in the extracted oil were analyzed qualitatively by GC/MS in order to establish GC-MS fingerprints of seed oil of Xinjiang Almond. Materials and Methods The oil of Almond was extracted by supercritical CO2 extraction technology and their chemical constituents were analyzed by GC-MS (Agilent 7890A-5975C MSD).Similarity evaluation system for chromatographic fingerprint of traditional Chinese medicine (Version 2004 A) published by the State Pharmacopeia Committee of China was employed for the representative standard fingerprint. Results and Discussion Study results showed that the fatty acids were composed of 92.2% unsaturated fatty acids. Furthermore, oleic acid (78.45%) linoleic acid (13.72%)and palmitic acid (6.1%) were the main fatty acids in Almond seed oil. The method on GC-MS fingerprints of oils of Almond was established and the GC-MS fingerprinting of oils of Almonds showed 8 characteristic peaks. The similarity of the GC-MS fingerprints of 20 samples was over 0.97. The method of GCMS fingerprinting is simple, accurate with good reproducibility and can be used for the comprehensive quality evaluation of Almond. Acknowledgments This work was supported by the Projects of International Science & Techology Cooperation of the Xinjiang Uygur Autonomous Region and the Central Asian Drug Discovery and Development Center of Chinese Academy of Sciences. References 1. Mandalari G., Nueno-Palop C., Bisignano G., Wickham M. S.,Narbad A. 2008. Potential prebiotic properties of almond (Amygdalus communis L.) seeds. Journal of Appl Environ Microbiol, 74:4264-4270. 2. YADA S, LAPSLEY K, HUANG G W. 2011. A review of composition studies of cultivated almonds: Macronutrients and micronutrients. Journal of Food Composition and Analysis, 24: 469-480.
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PP-183 Pollen analysis and antimicrobial activity of Algerian honey against pathogenic microorganisms Messaouda Belaid *1, Salima Kebbouche-Gana 1, Fatma Acheuk1, Djamila Benaziza 2 & Farida Benzina 1
1. Département de Biologie, Faculté des Sciences, Université M’Hamed Bougara de Boumerdes. Avenue de l’Indépendance-35000Algérie. 2. Ecole Normale supérieure Kouba. Alger (Algérie).
[email protected]
The aim of this study was carried out to assess the antimicrobial activity of different Algeria honeys against pathogenic microorganisms in respect to floral nectar origin. Various honey types were collected from different areas of Algerian (Lavender, polyfloral, Citrus sp, Hedysarum coronarium). Pollen analysis was done according to Louveaux et al (1978). To test the antimicrobial activity, the agar well diffusion methods was employed. The microbial strains tested were Pseudomonas aeroginosae, Klebsiella pneumoniae, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Streptococcus faecalis, Candida albicans, Saccharomyces cerevisae, Aspergillus niger and Rhizopus stolonifer. The polyfloral honey inhibited growth of Pseudomonas aeroginosae and Staphylococcus aureus significantly as compared to other honey. Citrus and Hedysarum coronarium honey exhibited respectivly the highest inhibition against Klebsiella pneumoniae and Saccharomyces cerevisae. Candida albicans was the most sensitive to Lavender honey. Several factors may influence the microbial activity of honey. The botanical origin plays an important role in the variation of the microbial potential of honeys against pathogenic microorganisms.
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PP-184 Crop protection and preservation of environment: IN VIVO evaluation in vivo of bisacylhydrazine ecdysteroid mimics (RH-5849 and RH-5992) on pupae of Ephestia kuehniella Leila Kirane-Amrani*, Asma Tazir & Nadia Soltani-Mazouni
Department of Biology, Laboratory of Applied Animal Biology, Reproduction & Development Group, Faculty of Sciences,University Badji Mokhtar of Annaba 23000-Annaba, Algeria.
[email protected]
In recent years, the toxicity of insecticides to humans and wildlife has caused much public concern and led to the use of more target-specific chemicals. Because of secondary effects of conventional insecticides, the insect growth regulators (IGRs) are receiving more practical attention to provide for safer foods and a cleaner environment. Among these compounds the dibenzoylhydrazines or non-steroidal ecdysteroid agonists, have been developed. Such compounds are hormonally active and disrupt development of pest insects primarily by induction of a precocious and incomplete lethal moulting in several insect orders; they exert their toxicity by binding to the ecdysteroid receptor as does the natural insect moulting hormone. The Mediterranean flour moth, Ephestia kuehniella Zeller (Lepidoptera: Pyralidae), is a cosmopolitan pest of stored products. Two compounds of this class (RH-5992 and RH-8549) were tested in vivo by topical application on the development of Ephestia kuehniella Zeller (Lepidoptera: Pyralidae) using a gravimetrical method. The compounds were diluted in acetone and applied topically to newly emerged pupae. The effects of this molecules were studied,on the biochemical composition of the cuticle using a gravimetrical method. The treated pupaes showed a different profile from that of controls.The results obtained showed that the two non-steroidal agonists reduced the amount of cuticle chitin without any significant effect on the cuticular protein content. Tebufenozide (RH-5992) causes an acceleration of development, he is more active than is RH-5849.
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PP-185 Spectrum-effect Relationship in Protein Tyrosine Phosphatase (PTP1B) Inhibition Effect of Carthamus tinctorius L. Heting Wu 1,3, Sanawear Mansur2,3, Yanhua Gao 1 , Haiqing Zhao 2, Xuelei Xin 1,2*, H. A. Aisa1,2*
Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011, Urumqi, P. R. China; 2 Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011, Urumqi, P. R. China; 3 University of Chinese Academy of Sciences, 100049, Beijing, P. R. China;
[email protected],
[email protected] 1
Introduction Protein tyrosine phosphatase 1B (PTP1B), which dephosphorylates the tyrosine residues of insulin receptor proteins, is primarily responsible for insulin resistance in type 2 diabetes. Therefore,PTP1B inhibitors ameliorating the insulindependent signaling pathway are potential candidaes for the treatment and prevention of diabets. As part of our continuous research for the water extract of Carthamus tinctorius L. as potent PTP1B inhibitors, the correlation between chromatography fingerprint of Carthamus tinctorius L. and the PTP1B inhibition activity was elaborated and the most effective substances were indicated by this way. Methods The fingerprint of the water extracts of 9 different origin Carthamus tinctorius L. was finished by HPLC, and the data were analysed by “computer aided similarity evaluation” TCM 2004A software(Fig.1). PTP1B inhibition activity of different water extracts of Carthamus tinctorius L. were detected, the spectrum-effect relationship was finished by using the Grey system theory modeling software GTMS3.0. Results and Discussion The efficacy of PTP1B inhibition of the water extract part of Carthamus tinctorius L. resulted in its chemical compositions together(Tab.1). The contribution order for PTP1B inhibition effect was(number of peaks): P4>P6>P1>P5>P3>P7>P8>P2, in which the number of peak 4 was identified as 3-O-caffeoylquinic acid, peak of 6 was hydroxysafflor yellow A(Tab.2). These work also provide an efficacious way on elucidating the active ingredients of traditional medicine. Acknowledgments We gratefully acknowledge financial support from the Joint Funds of the National Natural Science Foundation of China (Grant No. U1203203),and National Science & Technology Pillar Program (2011BAI05B05). No.
1
2
3
4
5
6
7
8
9
10.4
8.7
11.8
18.7
19.7
20.6
11.9
9.9
18.4
Peak
1
2
3
4
5
6
7
8
G
0.783
0.515
0.702
0.904
0.777
0.850
0.634
0.569
IC50 Ug/ml
Tab.1 Effect of the water extracts of 9 samples on PTP1B inhibition activity Tab.2 Common peaks of the water extrct in HPLC spectrum from 9 samples and gray relation grades(G)
Fig.1 Hplc chromatogram of the water extract of Carthamus tinctorius L. (365nm)
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PP-186 Antioxidant, antimicrobial and cytotoxicity of extracts from Curtisia dentata (Burm.f) C.A. Sm. VO Fadipe1*, NI Mongalo2, AR Opoku3
University of Zululand, Department of Chemistry, Private Bag X1001, KwaDlangezwa, 3886, South Africa. University of South Africa, College of Agriculture and Environmental Sciences (CAES, Laboratories), Eureka Building, Private Bag X6, Florida, 0710, South Africa.3University of Zululand, Department of Biochemistry, Private Bag X1001, KwaDlangezwa, 3886, South Africa.
[email protected]
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Introduction Curtisia dentata is traditional used in the treatment of various infections, including sexually transmitted infections, diarrhea, stomach ache, aphrodisiac, purgative and as a blood purifier. The plant species is being threatened through bark harvesting and mostly restricted to Southern Africa (Yembaturova et al., 2009). The current work is our continued effort in finding the alternative antibiotics as the microbes are generally developing resistance to common antibiotics mostly used in developing countries. Materials and methods The leaves were collected from Buffelskloof Nature Reserve (Mpumalanga Province, South Africa), washed and then extracted with acetone, ethanol and ethyl acetate respectively. The ethanol extract was further subjected to column chromatography and resulted in isolation of lupeol, betulinic acid (BA), β-sitosterol and ursolic acid (UA) which was isolated for the first time from the plant species. The isolated compounds and the extracts were investigated for antimicrobial activity (Eloff, 1998) against the ATCC strains of Candida albicans , Mycoplasma hominis, and Proteus mirabilis and Moraxella catarrhalis isolated from HIV patient in KwaZulu-Natal Province. Isolated active principles were then investigated for cytotoxicity against Human hepatocellular carcinoma (HepG2) cell lines (Mosman et al., 1983). Antioxidant activity of acetone extract was assessed against 2, 2-diphenyl-1-picryhydrazyl (DPPH) as described by Mongalo et al (2012).
H
COOH
H
Figure1. Ursolic acid
H HO H
Results and Discussion BA revealed lowest MIC values of 0.008 mg/ml against C. albicans while acetone extract showed 0.01 mg/ml against similar organism. Generally, BA revealed MIC ranging from 0.008 to 1.25 against the selected organisms, hence broad spectrum. The compounds inhibited the hepG2 cells in a dose dependent manner. The compounds revealed LD50 of >300 µg/ml except lupeol which revealed 289.4 µg/ml, suggesting the compound exhibited some degree of toxicity to the cells. However, Sahranavard et al (2009) refers isolated compounds with the LD50 of 100 µg/ml as toxic. Acetone extract exhibited IC50 of 0.78 mg/100ml. References 1. Eloff, J.N. 1998. A sensitive and quick micro plate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta Medica,64: 711-713. 2. Mongalo, N.I., Opoku, AR.., Zobolo, A.M. 2012. Antibacterial and antioxidant activity of the extracts of Waltheria indica Linn. Collected from Capricorn District, Limpopo Province, South Africa. Journal of Medicinal Plants Research,6(43):5593-5598. 3. Mosmann, T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods,65:55-63. 4. Sahranavard, S., Naghibi, F., Mosaddegh, M., Esmaeili, S., Sarkhail, P., Taghvaei, M., Ghafari, S. 2009. Cytotoxic activities of selected medicinal plants from Iran and phytochemical evaluation of the most potent extract. Research Journal of Pharmaceutical Sciences,4(2): 133-137.
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PP-187 Chemıcal Composıtıon oF Helianthemum sessiliflorum Hamada Haba*1, Imane Benabdelaziz1, Catherine Lavaud2, Dominique Harakat2, Mohammed Benkhaled1 LCCE, Département de Chimie, Faculté des Sciences, Université de Batna, Batna 05000, Algérie Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, BP 1039, 51097 Reims Cedex 2, France
[email protected]
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Introduction Helianthemum is a genus of plants including around 110 species of evergreen and semi-evergreen shrubs and belongs to the Cistaceae family. This genus can be found in America, Europe and Northern Africa. However, the Mediterranean region is considered its center of diversity [1]. Helianthemum sessiliflorum Pers. is a perennial plant usually grows in arid and semi-arid areas in the Mediterranean region [2,3]. A previous biological study revealed that H. sessiliflorum had interesting biological activities as analgesic and anti-inflammatory [4]. Materials and Methods Dried aerial parts (1Kg) of the plant material were macerated with 70% EtOH (3 × 10 L) at room temperature. The EtOH extract was concentrated then diluted with H2O and partitioned successively with cyclohexane (3 × 150 mL), AcOEt (3 × 150 mL) and n-buthanol (3 × 150 mL). The AcOEt extract (3.2 g) was fractionated on VLC (SiO2) with the solvent system cyclohexane/AcOEt (100:0 to 0:100) then AcOEt/MeOH (100:0 to 0:100) to give four Fractions (1-4). Purification of these fractions using reversed and normal phases Silica gel, Polyamide SC-6 and Sephadex LH-20 column chromatographies eluting with different solvents (MeOH/H2O, toluene/MeOH, CHCl3/MeOH,….) and HPLC (MeCN/H2O) resulted in the isolation of 20 compounds. Results and Discussion The 70% EtOH extract of the aerial parts of H. sessiliflorum was partitioned into fractions soluble in cyclohexane, AcOEt and n-butanol. Repeated CC over silica gel (SiO2), reversed-phase (RP-18), Polyamide SC-6 and Sephadex LH20, and semi-prep. HPLC (RP-18) of the AcOEt extract afforded 20 compounds, the new furofuran lignan; 1-O-acetyl prinsepiol (1), along with 19 known ones named 1α-hydroxypinoresinol (2), (+)-cycloolivil (3), ( ̶ )-pinellic acid (4), benzoic acid (5), p-hydroxybenzoic acid (6), protocatechuic acid (7), vanillic acid (8), gallic acid (9), ( ̶ )-epicatechin (10), ( ̶ )-catechin (11), ( ̶ )-epigallocatechin (12), ( ̶ )-gallocatechin (13), astragalin (14), tiliroside (15), quercetrin (16), isoquercetrin (17), myricitrin (18), β-sitosterol (19) and daucosterol (20). References 1. Mabberly, D.J. 1997. The plant book. Cambridge university press, Cambridge. 2. Battandier, J.A. 1888. Flore de l’Algérie Dicotylédones. Librairie F. Savy, Paris. 3. Ozanda, P. 1991. Flore et végétation du Sahara. 3ème édition, CNRS, Paris, France. 4. Ermeli, N.B., Alsabri, S.G., Bensaber, S.M., Mohamed, B.S., Zetrini, A.A., Aburas, K.M., Fitouri, S.R., Jaeda, M.I., Mrema, I.A., Hermann, A., Gbaj, A.M. 2012. Screening of analgesic and anti-inflammatory activities for two Libyan medicinal plants: Helianthemum lippii and Launaea residifolia. Journal of Chemical and Pharmaceutical Research, 4:4201-4205.
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PP-188 THE INFLUENCE OF SALVIFOLIN ON ATP-DEPENDENT POTASSIUM CHANNEL IN RAT LIVER MITOCHONDRIA IN STREPTOZOTOCIN-INDUCED DIABETES M.K. Pozilov1, M.I. Asrarov1, K.A. Eshbakova2
A.S.Sadykov’s Institute of Bioorganic Chemistry, Uzbek Academy of Sciences,Tashkent, Uzbekistan S.Yu.Yunusov’s Institute of the Chemistry of Plant Substance, Uzbek Academy of Sciences, Tashkent, Uzbekistan
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Introduction The development of experimental diabetes also involves ATP-dependent potassium channel in the plasma membranelocalized β-cells of the pancreas are opened. Nowadays, inhibitors, activators and pharmacology of potassium channels are known. However, in the literature the function and status of ATP-dependent potassium channel of the mitochondria (mitoKATP–channel) in diabetes, as well as modulators of their data are available. Clerodane-type diterpenoid salvifolin isolated from the Pulicaria salviifolia possess a hypoglycemic effect, it normalizes the metabolic processes in the body at experimental diabetes (Tashmuhammedova et al., 1992 and Eshbakova, 2011). However, salvifolin influence on mitochondrial function is not investigated and therefore our aim was to study the effect of salvifolin on mitoKATP–channel in the rat liver mitochondria of streptozotocin-diabetic rats. Materials and Methods Experiments were performed on 90 white mongrel male rats weighing 180-200 g. The animals were divided into three groups: I group - intact, II group - the animals with experimental diabetes, which once were injected intraperitoneally with an streptozotocin (50 mg/kg body weight intraperitoneally in a 0,1 mol/L citrate buffer, pH 4,5) (control) and, III group - streptozotocin diabetes + salvifolin (intraperitoneally dose of 3,5 mg/kg body weight) for 8 days starting from 12 days after administration of streptozotocin and reaching a predetermined level of hyperglycemia. Blood glucose was determined using glucose oxidase method set «Glucose - enzymatic-colorimetric test» (Cypress diagnostic, Belgium). Mitochondria isolated from rat liver by differential centrifugation according to Schneider. Mitochondrial swelling induced activation mitoKATP–channel was recorded using a change in light scattering at a wavelength of 540 nm. Results and Discussion Our experimental results indicate that diabetes with streptozotocin seriously impairs the function mitoKATP–channel rat liver mitochondria. Experiments have shown that in the absence of ATP in the incubation medium, with STZ-diabetic activity mitoKATP–channel is increased up to 20%, as compared to that of an intact rat group. In the presence of ATP, in experimental diabetes mitoKATP–channel liver becomes more open state, i.e., the rate of swelling of mitochondria in rat liver group II up to 92,1% than the group intact mitochondria. In diabetes, liver mitoKATP–channel becomes more open state, i.e., the swelling rate of the rat liver mitochondrial group II 88,5% is higher than the control group mitochondria. Pharmacotherapy salvifolinom corrects pathological change in function mitoKATP–channel: where the rate of swelling of rat liver mitochondria group III was inhibited in the absence of ATP up to 9,4 ± 0,6% and in the presence of ATP up to 65,7% in comparison with swelling rate of mitochondrial group II. Thus, when STZ-diabetes occur mitoKATF opens channel, which leads to increased transport of K + ions into the mitochondrial matrix, changes in potassium homeostasis cytosol. Perhaps, we studied diterpenoid salvifolin also interaction with the regulatory region of the channel - mitoSUR, resulting in the channel is inhibited. References 1. Khushbaktova ZA, Tashmukhamedova MA, Syrov VN, Mirtalipov DT, Grunina II. 1992. Effect of salvifolin on the carbohydrate and lipid metabolism in the rat liver in alloxan diabetes. Ukr Biokhim J, 64(3): 86-91. 2. Eshbakova KA. 2011 Chemical constituents of Pulicaria gnaphalodes Boiss. Med. plants. – 3 (2): 161-163.
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PP-189 EFFECTs OF FLAVONOID cHRYSOERIOL ON CONTRACTILE ACTIVITY OF SMOOTH MUSCLE CELLS OF RAT AORTA S.Z. Omonturdiev1, Y.T. Mirzaeva1, P.B. Usmanov1, B.J. Komilov2, K.A. Eshbakova 2
Institute of Bioorganic Chemistry. A.S.Sadykova, Academy of Sciences, 100170, Tashkent, Republic of Uzbekistan. E-mail:
[email protected] 2 S.Yu.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Tashkent, Republic of Uzbekistan.
[email protected] 1
Introduction Biologically active compounds of plant origin have a unique feature specifically modify function of different Ca+2 conveying systems smooth muscle cells (SMC). These compounds are of particular interest in the prospect of the creation on their basis of effective antihypertensive agents. In this paper we studied the action chrysoeriol flavonoid isolated from the plant Inula caspica, on the contractile activity of SMC aortic white rats. Materials and Methods The studies were conducted on isolated preparations of rat aorta, aortic contractile activity was assessed in isometric mode using tension sensor Grass FT. 03. Drug perfusion was performed with saline and Krebs-ringer oxigenated solution carbogen (O2-95% CO2-5%) at 37° C. Results and Discussion Preliminary studies have shown that chrysoeriol dose dependently (3 - 15 microns) relaxes the aorta preparations, predsokraschennye potassium solution (50 mM KCl). Thus, at a concentration of 3 mkM chrysoeriol drug induced relaxation of aorta 10 ± 3,1%, and at a concentration of 15 mkM, its relaxing effect reached 96,9 ± 4,6% compared to control.. To further clarify the mechanism of action chrysoeriol experiments were performed with a specific Ca+2 channel blocker of L-type - verapamil. Since verapamil effectively relaxes rat aorta preparations pre-cut potassium solutions. The concentration ED50 - for verapamil was 0.1 mkM, which caused relaxation of aorta 50 ± 2,2% as compared control. In the presence of verapamil addition to the incubation medium chrysoeriol ED50 was 9.3 mkM and induce relaxation to 79,7 ± 5,9%. Thus, it is shown that the flavonoid chrysoeriol has a strong relaxant effect, which is based on its ability to modify the properties of the potential-dependent Ca+2 - channels SMS rat aorta.
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PP-190 Research into Chemical Constituents and Pharmacological Effects of Euphorbia humifusa Silafu Aibai1, Li Zhijian1, Gulina Dawuti2, Abudujilili Abuduaini1, Amina Abula3 Institute of Xinjiang Traditional Uyghur Medicine, Urumqi, China, 830049. Xinjiang Uyghur Medicine Hospital, Urumqi, China, 830049. 3 Xinjiang Medical University, Urumqi, China, 830011.
[email protected] 1 2
Euphorbia humifusa Willd. or E. maculata L. are plants of the family Euphorbiaceae. Being one of the most commonly used Uyghur medicinal herb, it is recorded in the Pharmacopoeia of the People’s Republic of China and the Compendium of Materia Medica. Its chemical ingredients are flavonoids (quercetin, kaempferide, isoquercitrin), sterols (β- sitosterol), terpenes (sesquiterpenes and triterpenes), lactones and coumarins (scopoletin, umbelliferone, ayapin), tannin and phenolic acids, alkaloids, and unsaturated fatty acids, vitamins and others. Studies of the research group have shown: (1) Euphorbia humifusa extract and its effective parts showed a significant antifungal effect, and its anti-fungal mechanism of action is interfering with fungal cell membrane ergosterol biosynthesis pathway. Its efficacy is equivalent to positive drug terbinafine, fluconazole, with obvious dose-dependent manner.(2) Euphorbia humifusa compound obviously inhibited the xylene induced swelling of mouse ear and pronghorn vegetable gum induced rat paw edema, and also inhibited the rat cotton ball granulation tissue hyperplasia, showing a strong antiinflammatory effect (3). It improved mice neutrophil phagocytosis of staphylococci in vitro, decreased variety of active oxygen produced when macrophages are stimulated, improved the activity of antioxidant enzymes of immune organs, restrained the immune organ lipid oxidative damage, showed obvious inhibition effect on PMN “respiratory burst”, and effectively removed the O2, H2O2, OH-, O2 and other active oxygen free radicals.(4) It also obviously inhibited the rat homologous passive cutaneous anaphylaxis, DNCB induced delayed type hypersensitivity reactions of mice, showed an obvious inhibitory effect on rat mast cells with antibody mediated degranulation and prevented the release of active mediators, showed a significant antagonistic effect on guinea pigs induced itch reaction caused by histamine phosphate and increased the itch threshold. In short, Euphorbia humifusa and its effective parts have antifungal, anti-bacterial, anti-inflammatory, antiallergic, antioxidant and immune regulation function, which provided strong scientific basis for the development of using Euphorbia humifusa resources. Acknowledgments Xinjiang Uyghur Autonomous Region High Technology Research and Development Program (201517111).
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PP-191 Chemical composition and antifungal activity of essential oils of Artemisia herba alba Asso grown wild in Ouenza (Tebessa -Algeria) M. Belleili*1, H. Bensisaid 1, Y. Hadef 1, A. Gouri 2
Laboratory of Analytical Chemistry, Department of Pharmacy, Faculty of Medicine, Badji Mokhtar Annaba University, Algeria. Laboratory of Biochemistry, EPH Ibn Zohor , Guelma , Algeria. e-mail:
[email protected]
1 2
Introduction Essential oils have found their place in aromatherapy, pharmacy, perfumery, cosmetics and food preservation. Their use is related to their broad spectrum of biological activities recognized. The aim of the present study was to evaluate the antifungal effect of A.herba alba Asso essential oils. Material and methods The essential oils were isolated by hydrodistillation from the aerial parts of Artemisia herba alba Asso and analyzed by Gas Chromatography-Mass Spectrometry (GC-MS). The minimal inhibitory concentration (MIC) was made in Sabouraud liquid medium by the serial dilution method. Results and discussion Essential oils yield ranged between 1.27 and 1.37 %. The main components were found to be camphor (48.5 %) , α - thujone (11.9 %) , chrysantone (6.3 %), eucalyptol (5.6 %) , pinocarvone (5.0 %) and camphene (4.8 %). The essential oils were tested for antifungal activity against Candida albicans, minimal inhibitory concentration (MIC) was made in Sabouraud liquid medium by the serial dilution method. The essential oil of Artemisia herba alba Asso presented a very good antifungal potency against Candida albicans with MIC value of 80 % = 5.04 mu.l / ml.
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PP-192 Analysis of the Chemical Compositions from Subgenus Grammosciadium DC; G. confertum Hub.-Mor. & Lamond, G. cornutum (Nábělek) C.C.Towns., G. macrodon Boiss. and G. daucoides DC., growing in Turkey Nurgün Küçükboyacı1, Betül Demirci2, Fatma Ayaz*1, Barış Bani3, Nezaket Adıgüzel4
Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey 3 Department of Biology, Faculty of Arts and Science, Kastamonu University,37200, Kastamonu,Turkey 4 Department of Biology, Faculty of Science, Gazi University, 06500 Ankara, Turkey *
[email protected] 1 2
Introduction The genus Grammosciadium DC. (Apiaceae) is distributed by 8 taxa in Turkey. The species were classified under 2 subgenera, namely Grammosciadium and Caropodium (Stapf & Wettst.) Tamamsch. & V.M.Vinogr. In Turkey, the subgenus Grammosciadium contains G. daucoides DC., G. macrodon Boiss., G. cornutum (Nábělek) C. C. Towns. and G. confertum Hub.-Mor. & Lamond. Among them, G. confertum is endemic to Turkey. All the species of the subgenus are Irano-Turanian element, except for G. confertum (Hedge and Lamond, 1972; Vinogradova, 1995; Pimenov and Leonov, 2004). Materials and Methods Essential oils obtained by hydrodistillation from aerial parts and fruits of four Grammosciadium DC. species belonging to subgenus Grammosciadium, collected from different locations in Turkey, were simultaneously analyzed by GC and GC/ MS systems. Results and Discussion The analysis revealed 124 constituents, accounting 71.1-99.8% of the oils. Major component of the essential oil samples from G. cornutum and G. confertum was found to be hexadecanoic acid (13.3-21.2% and 48.1-59.8%, respectively). Therefore, caryophyllene oxide (13.1-29.2%) was the major constituent in G. macrodon samples, as well as γ-terpinene (61.9%) and carvacrol (68.9%) in G. daucoides samples. To the best of our knowledge, we firstly defined the chemical characterization of the essential oil obtained from G. cornutum, G. macrodon and G. confertum growing in Turkey. Acknowledgments This study was supported by Gazi University-BAP (02/2012-24) and TUBİTAK (11Z094). References 1. Hedge, I.C. and Lamond,J.M. 1972. Grammosciadium DC. In: Davis,P.H. (ed) Flora of Turkey and East Aegean Islands, Vol. 4, University Press, Edinburgh, pp 318-321. 2. Pimenov, M.G. and Leonov, M.V. 2004. The Asian Umbelliferae biodiversity database (ASIUM) with particular reference to South-West Asian taxa. Turk. J. Bot., 28: 139-145. 3. Vinogradova, V.M. 1995. The new data on the genus Grammosciadium and the systematic position of Fuernrohria setifolia (Apiaceae). Bot. Zhurn., 80(1): 91-99.
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PP-193 NEW INTRODUCED COTTON SORT “BUKHARA-9” DOESN’T CONTAINING GOSSYPOL Kh.Sh.Nematov, Sh.Kh.Rakhimova*, L.G.Mejlumyan, Sh.Sh.Sagdullaev
Acad. S.Yu.Yunusov Institute of the Chemistry of Plant Substances, Tashkent, Uzbekistan
Introduction Cotton is the basic culture grown in Uzbekistan. Selectionists from the Bukhara Department of the Uzbek Scientificresearch Institute of Cotton developed the new cotton sorts of “Bukhara” series. Overall chemical investigation has been carried out in order to identify high-yielded, high resistant to diseases and pests sorts. “Bukhara-9” sort attracted a special interest because of lack of gossypol in its seeds. Materials and Methods We have identified high inhibitory lines represented high value for plant selection due to their morphological and practical properties: precious, high yield, yield and length of fiber, size of bolls, weight of 1000 seeds, oil content (Mejlumyan, 2008). Continuing the investigation of marker proteins of cotton seeds, we isolated and characterized the proteinase inhibitors from new introduced sorts “Bukhara-9”, UzFA 705 and Mirishkor containing not more than 1% of gossypol (Yuldasheva et al., 2014). Results and Discussion We isolated and purified the proteinase inhibitors from newly introduced cultivars “Bukhara-9”, UzFA 705 and Mirishkor containing not more than 1% of gossypol, and sort “Bukhara-9” doesn’t containing gossypol. Their inhibitory activity values were identified. It was established using electrophoresis, that the inhibitors from the seeds of investigated sorts consist of three protein components with molecular masses to be 50, 37, 20 kD. The comparative analyses of the activity of inhibitors isolated from new sorts “Bukhara-9”, UzFA 705 and Mirishkor carried out. It was found, that “Bukhara-9” and UzFA 705 sorts have the same value of inhibitory activity like previously introduced sort An-Bayaut-2, while inhibitory activity of Mirishkor sort was higher than the one in “Turon” sort grown in low water supply conditions. “Bukhara-9” sort contained mainly 20 kD protein component. Some differences have been observed in IR spectrum of this sort compare to other investigated sorts. In the amino acids composition of the proteinase inhibitors such amino acids as asparagine, glutamine, proline prevailed. It was established that Mirishkor sort proteins highly inhibited the growth of Fusarium oxisporum. References 1. L.G.Mejlumyan. Chem.Nat.Compd. (2008), No.1, p.43-45 2. N.K.Yuldasheva, L.G.Mejlumyan, Sh.Kh.Rakhimova, S.D.Gusakova, N.T.Ulchenko, Kh.Sh.Nematov, Sh.Sh.Sagdullaev. Uzbek Chem. J.(2014), No.4.
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PP-194 Synergistic Effects Between the Essential Oil of Thymus numidicus Poir. and Amphotericin B Youcef Hadef *(1,2) , Z’hor Gousami(1,2 , Samia Lakhel (1,2) , Mohamed Tahar Benmoussa(3) , Azeddine Chefrour(2)
Laboratoire de Chimie Analytique, Département de Pharmacie, Faculté de Médecine, Université Badji Mokhtar, BP 205, Annaba (23000), Algérie. 2 Laboratoire de développement et de contrôle des préparations pharmaceutiques hospitalières Département de Pharmacie, Faculté de Médecine, Université Badji Mokhtar, BP 205, Annaba (23000), Algérie. 3 Laboratoire de pharmacognosie, Département de pharmacie, Faculté de Médecine, Université Hadj Lakhdar, Batna, Algérie. 1
The development of fungal infections in patients receiving immunosuppressive therapy requires the search of new antifungal agents, especially as the available drugs such as Amphotericin B cause significant side effects during continuous use. As part of the study of antifungal properties of algerian flora, essential oil of Thymus numidicus Poir., an endemic from Numidia (north-eastern Algeria) used in traditional medicine in the Mediterranean area. The essential oil has a high antifungal activity (MIC 80% = 0,695 nL.mL-1, Kaff = 5,232 nL-1 mL ). GC-MS analysis show a high rate of thymol (57%) and its precursor, p-cymene (7,55 %). Thymol is well known for its antimicrobial properties. The concomitant use of this essential oil with Amphotericin B may be useful to decrease the side effects of this antifungal drug. This study reveals a synergy of action between the essential oil of Thymus numidicus Poir. and Amphotericin B for an essential oil concentration of 0,25 µL. mL-1. Such a combination would be advantageous as the basis of a less toxic antifungal therapy. The very small amount needed to obtain this synergy effect suggests that no toxic effects will be observed in vivo toxicity testing that must be conducted before every clinical trial. Indeed, acute oral toxicity studies of thymol, one of the main constiutants of the essential oil, reveal an LD50 value of 2000 mg/kg in rats. References 1. Hadef Y., Kaloustian J., Chefrour A., Mikail C., Abou L., Giordani R., Nicolay A., Portugal H. Chemical composition and variability of the essential oil of Thymus numidicus Poir. from Algeria. Acta Botanica Gallica, (2007), 154, 2 : 265-274 2. Adams RP. Identification of essential oil components by gas chromatography and mass spectroscopy. Carol Stream (IL): Allured; 1995. 3. Espinel-Ingroff A, Pfaller MA. Antifungal agents and susceptibility testing. In: Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken RH, editors. Manual of clinical microbiology. Washington DC: ASM Press; 1995. 4. Giordani R, Buc J, Regli P. Mycoses 2002;45:482.
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PP-195 Histopathological effects of mixtures of insecticide in the hepatopancreas of terrestrial gastropod Helix aspersa Smina Ait Hamlet 1, Samira Bensoltane 2, Mohamed Djekoun3 & Houria Berrebbah 1
Cellular Toxicology Laboratory, Department of Biology, Faculty of Sciences, Badji-Mokhtar University, Annaba, P.O. Box 12, 23000, Algeria 2 Faculty of Medicine, Badji-Mokhtar University, Annaba, 23000, Algeria 3 Department of Biology, Faculty of Sciences and the Universe, University of May 08th, 1945, Guelma, 24000, Algeria
[email protected] 1
Introduction In Algeria, the usage of insecticides and other phytosanitary products spreads more and more with the development of agriculture. So, the analyses of the residues of pesticides are not systematically made. Thus, in this context, we estimated with an experimental study, the effect of a mixture of two insecticides, on the terrestrial gastropod Helix aspersa. The first is the thiamethoxam (included in the neonicotinoids chemical family) which is used as a commercial preparation. This is an alkaloid of tobacco plant, used as irrigation since the 19th century. The second is the tefluthrin (included in the pyrethrinoïds chemical family). This insecticide is also used as a commercial preparation. It is synthesized from the Chrysanthemum flowers, acting by contact and ingestion on a very wide range of insects, in all cultures and at very low doses. They are widely used in the Algerian North-East region. Materials and Methods In this work, adult snails, Helix aspersa, which is one of the most abundant gastropod in north-east Algeria, were used to estimate the effect of four mixtures of thiamethoxam and tefluthrin on histological changes in the hepatopancreas of this gastropod after a treatment of six weeks. During this period, snails were exposed by ingestion and contact to fresh lettuce leaves which were soaked with an insecticide solution. They are used as a commercial preparation, which are lower or equal to the concentrations that are applied in the field. Results and Discussion The histological examination of the hepatopancreas of the treated snails showed alterations as a response to all the treatments, larger intertubular connective tissue and revealed the degeneration of the digestive tubules and the breakdown of the basement membrane. Indeed, the effects of the mixtures do not necessarily reflect the effects of substances taken individually. Possible interactions between the components of a mixture are quite complex and make the prediction of the overall effect very difficult. The histological changes on the hepatopancreas can be considered as a useful research tool to assess toxic effects of mixture’s insecticides in Helix aspersa. Acknowledgments We would like to thank the General Director of the Research of the Algerian Ministry of High Teaching and Scientific Research. References 1. Schwaiger, J., Wanke, R., Adam, S., Pawert, M., Honnen, W. and Triebskorn, R. (1997). The use of histopathological indicators to evaluate contaminant-related stress in fish. Journal of Aquatic Ecosystem Stress and Recovery, 6: 75-86. 2. Snyman, R.G., Reinecke, A.J. and Reinecke, S.A. (2005). Quantitative changes in the digestive gland cells of the snail Helix aspersa after exposure to the fungicide copper oxychloride. Ecotoxicology and environmental safety, 60: 47-52.
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PP-196 MICROBIAL BIOTRANSFORMATION OF OLEIC ACID AND THE CYTOTOXICITY OF BIOTRANSFORMATION MIXTURES Özge Özşen*, İsmail Kıran1, Özlem Atlı2 and Fatih Demirci3
Department of Chemistry, Faculty of Arts and Sciences, Eskişehir Osmangazi University, 26480, Eskişehir, Turkey Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Anadolu University, 26470, Eskişehir, Turkey 3 Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskişehir, Turkey
[email protected];
[email protected] 1,* 2
Introduction Oleic acid is a saturated fatty acid present in various vegetable oils such as hazelnut, sunflower and olive and found as glyceryl esters in animal fats by 30%. It is known that oxygenated fatty acids are effective against some cancer types (Bastida et al., 1999). Therefore derivatization of oleic acid is an important field of study. In this study, we aimed at obtaining derivatives of oleic acid using biotechnological methods and investigate their possible anticancer and cytotoxic activities. Materials and Methods Biotransformation studies Pre-biotransformation of oleic acid was carried out with 27 different microorganisms for 7 days at 25oC. α-medium was used for growth of microorganisms. Cytotoxicity tests Cytotoxicity tests were performed using A549 (human lung carcinoma cell line) and NIH3T3 (mouse embryonic fibroblast cell line) by XTT test, which measures mitochondrial activity. 105 cells/well were seeded and mixtures were prepared in DMSO (< 0.1%) at concentrations of 3,9-500 μg/ml in triplicates. Cisplatin was used as positive control. IC50 values were estimated by non-linear regression analysis according to OD480 and OD680 values (Altintop et al., 2012). Results and Discussion Extracts obtained from biotransformation of oleic acid with Alternaria alternata (M1) and Aspergillus terreus var. africanus (M2 and M3) were used for cytotoxic studies. Mixtures were found to have the highest cytotoxic activity against A549 cells with IC50 values of 62,5 (M1), 89,6 (M2) and 117,03 (M3) µg/ml, respectively. M1 and M3 were found to be selectively cytotoxic against A549 cell line by showing higher IC50 values against NIH3T3 cells. M1 showed similar anticancer activity against A549 cells with our positive control, cisplatin (IC50= 43,52 µg/ml). The anticancer potential of M1 was also found to be selective against A549 cells by showing lower cytotoxicity (IC50=122, 7 µg/ml) against healthy cells, NIH3T3. Further studies may be conducted to evaluate the anticancer activity of M1 mechanistically or in animal models. Acknowledgement We thank Eskişehir Osmangazi University for supporting our project (Project No: 2014-654). References 1. Bastida, J., de Andrés, C., Culleré, J., Busquets, M. ve Manresa, A. 1999. Biotransformation of oleic acid into 10-hydroxy-8Eoctadecenoic acid by Pseudomonas sp. 42A2, Biotechnology Letters, 21: 1031-1035. 2. Altıntop M.D., Özdemir A., Turan-Zitouni G., Ilgın S., Atlı Ö, İşcan G., Kaplancıklı Z.A. 2012. Synthesis and Biological Evaluation of Some Hydrazone Derivatives as New Anticandidal and Anticancer Agents, European Journal of Medicinal Chemistry, 58: 299-307.
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PP-197 Herbal medicine in diabetics Ethnobotanical survey, phytochemical analysis and evaluation of the antioxidant activity of five medicinal plants A. Lardjam, R. Mazid, N. Amara, Z.F. Sahraoui, M. Dif, L. Zemmour, W. Khitri The pharmacy department -faculty of medicine of Oran- Algeria
[email protected]
Diabetes is one of non communicable diseases which represents a major public health problem, despite the existence of a range of chemical synthetic medicines against this disease. Currently over more patients use complementary or alternative medicine and especially in phytotherapy. It is about ancient medicines suitable for a long time its substances to allopathic medicine and serving as a model for many synthetic medicines. Our work is part of the value of herbal medicine. For this, an ethnobotanical survey was conducted with 314 type 2 diabetics showed that 35.40% of the study population use medicinal plants of which 56 species were listed of 28 families. A composition identification of some herbal teas sold in our area for diabetics allowed us to reveal several forgeries, which explains a bad regulation of these products. A phytochemical analysis and an evaluation of antioxidant activity, which were carried on five plants, most reputed as antidiabetics: fenugreek, olive, white wormwood, berberis, oregano, show high total polyphenols levels, correspond with significant antioxidant activities (except in case of fenugreek where its antioxidant power is not attributed to total polyphenols).
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PP-198 Isolation of secondary metabolites of Persicaria maculosa extract with GIRK channel-modulatory activity Andrea Vasas, Ildikó Lajter, Peter Forgo, Judit Hohmann*
Department of Pharmacognosy, University of Szeged, Szeged, Hungary
[email protected]
Introduction Polygonum persicaria L. (syn. Persicaria maculosa Gray) is native to Europe and is widely distributed as a weed throughout temperate and tropical North and South America, Asia, North Africa and Australia. It is a morphologically extremely variable perennial plant. Previous phytochemical studies revealed the presence of stilbenes, flavones, flavonols, chalcones, flavanones and phenolic acids in this species. Our previous pharmacological study demonstrated the effect of the CHCl3 extract of P. persicaria extracts on the G protein-activated inwardly rectifying K+ (GIRK) channel, which was investigated by an automated patch clamp method (Lajter et al, 2013). The GIRK channels, novel targets for the development of new therapeutic agents, are activated by a large number of G protein-coupled receptors and regulate the electrical activity of neurones, cardiac atrial myocytes, and β-pancreatic cells. Abnormalities in GIRK channel function have been implicated in the pathophysiology of neuropathic pain, drug addiction, cardiac arrhythmias and other disorders. Materials and Methods The CHCl3 extract of P. persicaria was subjected to multistep chromatographic separations, including VLC, RP-MPLC, preparative RP-TLC and gelfiltration. The structure determination of the isolated compounds was performed by mass spectrometry and 1D and 2D NMR experiments (1H-1H COSY, 13C-NMR, NOESY, HSQC and HMBC). Results and Discussion From the CHCl3 extract 9 compounds, belonging to the flavanone, chalcone, carboxystilbene and ionon glycoside groups were isolated. 2’-Hydroxy-3’,4’,6’-trimethoxychalcone, pinostrobin-chalcone, 6-hydroxy-5,7-dimethoxyflavanone, onisyline, 5-hydroxy-7,8-dimethoxy-flavanone and (6R,9S)-3-oxo-α-jonon-β-D-glucopyranoside were identified for the first time from this plant species. Our results strengthen the chemotaxonomic observation that common occurrence of structurally related flavanones and chalcones are characteristic to the Polygonum genus (Smolarz, 2002). The isolated compounds, together with the known metabolites of this plant (persilben, 5-hydroxy-7,8-dimethoxyflavanone, pinostrobin and pinostrobin-chalcone) are planned to investigate for GIRK channel-inhibitory effect. Acknowledgments Financial support from the Hungarian Scientific Research Fund (OTKA K109846) is gratefully acknowledged. References 1. Lajter, I., Vasas, A., Orvos, P., Tálosi, L., Forgo, P., Béni, Z., Hohmann, J. 2013. Inhibition of GIRK channels by extract of Polygonum persicaria and isolation of new flavonoids. Planta Medica, 79: 1736-1741. 2. Smolarz, H.D. 2002. Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L. Acta Poloniae Pharmaceutica, 59: 145-148.
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PP-199 Biological activities of Juniperus phonicea Tar, growing wild in Bechar region, south west of Algeria. A.Makhloufi1, A.Boulanouar1, L.Mebarki2L.Benlarbi1, B.Tarfaya1,
Laboratory of valorization of vegetal Resource and Food Security in Semi Arid Areas, South West of Algeria, BP 417, University of Bechar, Algeria 2 Laboratoire des productions, valorisations végétales et microbiennes Université des sciences et de la technologie d’Oran Mohamed Boudiaf Algeria 1
Biological activities of medicinal plants have been recognized for a long time. In the present study, antioxidant and antimicrobial properties of Juniperus phonicea Tar, were investigated for their antimicrobial activities against six strains of fungi and six strains of bacteria. Its sensitiveness (Minimal Inhibition Concentration) to mentioned micro-organisms were as follows: Klebsiella pneumoniae (0.032 mg/ml), Staphylococcus aureus (0.05 mg/ml), Pseudomonas aeruginosa. Enterococcus faecalis, Escherichia coli, Listeria monocytogenes(0.1mg/ml). For fungi , and according to these results, the tar has great antifungal activity against all the investigated strains. The growth inhibition rate ranged from 0.006 to 0.1mg/ml with the highest inhibition values observed against Fusarium oxysporum f.sp albedinis (1)(0.006 mg/ml). The antioxidant capacity of the tar was evaluated using hydrogen peroxide scavenging, 1,1-diphenyl-2-picrylhydrazyl (DPPH), showed potent antioxidant ability ( EC50=(EC50= 1.45±0.16 mg ml-1) compared to the ascorbic acid used as positive control( EC50=2.19±0.12 mg ml-1) .
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PP-200 Alkaloids of Haplophyllum griffitianum D. R. Kodirova 1, Kh. A. Rasulova 1, A.Yili 2, H.A. Aisa 2
1. Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Tashkent, Uzbekistan, fax (99871) 120 64 75, 2. Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China.
[email protected]
Introduction Haplophyllum plants of the genus are presented by several species and wide spread on vast territories of Central and South Asia, in West and East Siberia up to step regions of Far East. This plant is rich in quinoline alkaloids and known as cytostatic and sedative compounds. some alkaloids increase locomotor activity and potentiate seizures caused by caffeine, pentetrazole and strychnine. Such compounds may be evaluated as potential psychostenic and antidepressive drugs. Studying alkaloids of Haplophyllum represents certain theoretical and practical value. Materials and Methods For the first time were investigated alkaloids from the aerial parts of Haplophyllum griffitianum collected in Surhandarya region. The plant was extracted with MeOH. From methanolic extracts have been obtained 0.45% and 0.6% (by weight of dry plants) mixture of alkaloids. By column chromatography from sum of total alkaloids were isolated known bases dictamnine (1), skimmianine (2), dubinidine (3), dubinine (4), dubamine (5), N-methilhaplofoline (6), new bases gerfitine (7), gerfitinine (8), grifitine (9) and sterens with mp 76-78o. Results and Discussion The known alkaloids (1-6) were identified by comparison with authentic samples and. Alkaloids dictamnine (1), skimmianine (2), dubinidine (3), dubinine(4), dubamine (5) and N-methilhaplofoline (6) were isolated from Haplophyllum griffitianum for the first time. The structure of a new alkaloids gerfitine (7), gerfitinine (8), grifitine (9) was elucidated by study spectral data (1H and 13C NMR spectra), as well as DEPT and HETCOR experiments. Acknowledgment This works was supported by The Xinjiang Uygur Autonomous Region science and technology project 2013721044 and Central Asia Center of Drug Discovery and Development of Chinese Academy of Sciences. OCH 3
R
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PP-201 Synthesis and Anti-Influenza Activity of Rupestonic Acid Derivatives Jiangyu Zhao1, Gen Li 1, H. A. Aisa *,1
The Key Laboratory of Plant Resources and Chemistry of Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. China
[email protected]
1
Introduction Artemisia rupestris L., a Traditional Chinese Medicine, had a long history as a folk medicine in Xinjiang of China. It is known to be effective as anti-virus, anti-tumor, anti-inflammatory, antibacterial and antidote agents[1]. Rupestonic acid is a sesquiterpene with multifunctional groups, isolated from the Artemisia rupestris L. In the previous research, more than 200 rupestonic acid derivatives have been synthesized and preliminarily assayed in vitro against influenza A (H1N1, H3N2) and B viruses[2-4]. Materials and Methods Dry Artemisia rupestris L. was extracted with 95% ethanol, the extract was evaporated under reduced pressure. Rupestonic acid was isolated by silica gel column chromatography using petroleum ether/ethyl acetate (10:1-1:1) as the eluent, followed by recrystallization from acetone. In order to continue our ongoing studies and examine the structure effect relationship of rupestonic acid deeply, ester, O-ketone oxime, ether, carboxyl, acetoxyl, halogen, hydroxyl, alkyl, aryl and heterocyclic were introduced into C(3) carbonyl and C(2) methylene of rupestonic acid by conventional chemical reactions. To determine the potential activity of compounds, they were preliminarily assayed in vitro against influenza A (H3N2, H1N1) and B viruses. Results and Discussion Thirty rupestonic acid analogues at C(3) and twenty rupestonic acid derivatives at C(2) have been synthesized. The activity results showed that most analogues showed better activity than parent compound against influenza virus A. The antiviral activity of the C(2) derivatives is being tested. Acknowledgments This work was financially supported by Xinjiang High-Tech R&D Program (No.201317101), National Natural Science Foundation of China (No. 81402808), Natural Science Foundation of Xinjiang, China (No.2014211A070) and West Light Foundation of The Chinese Academy of Sciences(No. XBBS201218). References 1. Ma, Y. M.; Aisa, H. A.; Liao, L. X.; Srapil, E. B.; Zhang, T. Y.; Ito, Y. J. Chromatogr., A. 2005, 1076, 198. 2. Y. W. He, C. Z. Dong, J. Y. Zhao, L. L. Ma, Y. H. Li, H.A. Aisa, European Journal of Medicinal Chemistry, 2014, 76: 245-255; 3. Zhao, J. Y.; Aisa, H. A. Bioorg. Med. Chem. Lett. 2012, 22, 2321-2325. 4. Yong, J. P.; Aisa, H. A. Bull. Korean Chem. Soc. 2011, 32(4): 1293-1297. 5. Yong, J. P.; Lv, Q. Y. and. Aisa, H. A. Bull. Korean Chem. Soc. 2009, 30(2): 435-440.
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PP-202 Pinus mugo Turra. essential oil, its fractions and selective antimicrobial drug combinations against resistant pathogens Gamze Göger*, Merve Baysal, Sinem Ilgın, Betül Demirci, Fatih Demirci
Graduate School of Health Sciences, Anadolu University, 26470-Eskişehir, Turkey Department of Pharmacognosy Faculty of Pharmacy, Anadolu University, 26470- Eskişehir Turkey Faculty of Pharmacy, Deparment of Pharmaceutical Toxicology, Anadolu University 26470-Eskişehir Graduate School of Health Sciences, Anadolu University 26470-Eskişehir *
[email protected]
Pinus mugo Turra. (Pinaceae) is known as dwarf mountain pine and grows in the mountainous regions of Central and Southern Europe. P. mugo essential oil is used as antiseptic, antimicrobial, antiinflammatory, antiviral among other uses (Reichling et al., 2011; Venditi et al., 2013). In this present study, commercial Pharmacopeia (PhEur) grade dwarf pine oil (Pini pumilionis aetheroleum) and its column chromatography fractions (n-hexane, diethly ether, dichloro methane, methanol) were combined with standard antimicrobial agents such as ampicilline, cefuroxime, tetracycline, fluconazole and nystatine, respectively. The chemical compositions of the essential oil and four fractions were determined both by GC/FID and GC/MS techniques. All combinations were evaluated in vitro against pathogenic standart and clinical resistant Escherichia coli, Staphylococcus aureus and Candida albicans by the CLSI microdilution and checkerboard methods. Resulting fractional inhibitory concentrations were calculated and interpreted as synergy, additive or indifferent. To determine the selectivity of the antimicrobial combinations the WS1 (human normal skin fibroblast) cell line were used for in vitro cytotoxicity testing. Inhibition % was calculated for each concentration of test samples where IC50 values were calculated by non-linear regression analysis. α-Pinene (18.4 %), δ-3-carene (18.4 %), β-phallendrene (15.2 %), β-pinene (10.5 %), limonene (9.0 %), mycene (6.7 %) and terpinolene (6.7 %) were the major identified compounds of the essential oil, respectivetly. P. mugo essential oil and fractions in combination with ampicilline, cefuroxime, tetracycline resulted as “synergistic” and “additive” against S. aureus rather than E. coli. Essential oil combination with fluconazole and nystatin resulted as “indefferent” particularly against resistant clinical Candida isolates. In vitro cytotoxicity of essential oil, hexan fraction, diethyl ether fraction, ampicilline, cefuroxime, tetracycline, fluconazole and nystatine IC50 values are 64.75, 116.73, 229.28, >500, 359.5, 383.64, > 500, 83.95, respectively. Acknowledgments This work is part of the PhD project of GG and was supported by the Anadolu University Research Funding (Project no: BAP-1301S005). References 1. Reichling, J., Schnitzler, P., Suschke, U., Saller, R., Essential oils of aromatic plants with antibacterial, antifungal, antiviral, and cytotoxic properties-an overview, Forsch. Komplementmed, 16 (2), 79 (2009). 2. Venditti, A., Serrilli, A. M., Vittori, S., Papa, F., Maggi, F., Di Cecco, M., Ciaschetti, G., Bruno, M., Rosselli, S., Bianco, A., Secondary metabolites from Pinus mugo Turra subsp. mugo Growing in the Majella National Park (Central Apennines, Italy), Chem. Biodivers., 10 (11), 2091-2100 (2013).
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PP-203 On-line screening and identification of antioxidant phenolic compounds of Salvia aegyptiaca L. Samir Benayache 1,*, Sabrina Mohamadi1, Minjie Zhao2, Amel Amrani1, Eric Marchioni2, Djamila, Fadila Benayache 1. Unité de recherche Valorisation des Ressources Naturelles, Molécules Bioactives et Analyses Physicochimiques et Biologiques. Université frères Mentouri, Constantine, Route de Ain El Bey, 25000, Constantine, Algérie. 2 Equipe de Chimie Analytique des Molécules Bioactives, Faculté de Pharmacie, 74, route du Rhin 67401, Illkirch, Cedex, France.
[email protected] 1
Introduction Currently there is an increasing interest in research and isolation of new sources of natural antioxidant which may provide safe antioxidant additives for food industry [Pokorni et al., 2001]. The antioxidant properties of plant extracts have been attributed mainly to their polyphenol contents. Salvia species constitute important sources of phenolic antioxidants [Harley et al., 2004]. We report the investigation of the polyphenolic contents of the extracts of Salvia aegyptiaca collected in the South west of Algeria Material and methods In this study, the chloroform, ethyl acetate and n-butanol extracts of Salvia aegyptiaca were evaluated for their free radical scavenging capacity by analytical methods : 2,-azino-di(3-ethyl-benzo thiazoline -6-sulfonic acid (ABTS.+) and 2,2’- diphenyl-1-picrylhydrazyl (DPPH.) free scavenging capacity assays. On-line HPLC-ABTS+ [Koleva et al., 2000] and subsequent fractionation followed by spectroscopic analysis (HRMS, UV, NMR: 1H, 13C, COSY, NOESY, HSQC and HMBC) were applied to screen and identify free radical scavengers in the extracts. Results and discussion Ten compounds were identified, caffeic acid 1, vanilic acid 2, syringic acid 3, Luteolin 7-O glucoside 4, apigenin 7-O-glucoside 5, diosmin 6, rosmarinic acid 7, Luteolin 8, methyl rosmarinate 9 and apigenin 10. These compounds were the dominant free radical scavengers in the species as expressed by their trolox equivalent antioxidant capacity (TEAC). Rosmarinic acid, methyl rosmarinate, luteolin and caffeic acid were the most active components (TEAC: 32. 9, 26.2, 11.9 and 31.93 μg/mL respectively), these results were validated by offline antioxidant DPPH assay . Compounds 2, 3, 6 and 9 are described for the first time in Salvia aegyptiaca . Aknowledgement This work was supported by DGRSDT and Tassili (Algeria-France cooperation) project ( 856/MDU/56). References 1. Harley, R.M., Atkins, S., Budantsev, A.L., Cantino, P.D., Conn, B.J., Grayer, R., Harley, M.M., de Kok, R., Krestovskaja, T., Morales, R., Paton, A.J., Ryding, O., Upson,T., 2004. Labiatae. In: Kadereit, J.W. (Ed.), The Families and Genera of VascularPlants, Lamiales, vol. VII. Springer, Berlin, pp. 167–282. 2. Koleva, I.I., Niederländer, H.A.G., and Van Beek, T.A., 2000. An on-line HPLC method for detection of radical scavenging compounds in complex mixtures, Anal. Chem. 72 (10), 2323-2328. 3. Pokorni, J., Yanishlieva N., Gordon, M., Antioxidant in food practical applications, CRC Press, Woodhead publishing Ltd, 2001.
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OH COOH
COOH
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Figure 1 : Polyphenolic compounds isolated from Salvia aegyptiaca L.
Figure 2: On-line HPLC-ABTS chromatogram of EtOAc Extract
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PP-204 Comparative studies on antisickling properties of brown and green leaves of Carica papaya Linn. (Caricaceae) GO Ajayi* and OM Ogun
Department of Pharmacognosy, Faculty of Pharmacy, University of Lagos, Lagos, Nigeria
[email protected]
Introduction Sickle Cell Anaemia (SCA) is characterised by non-covalent polymerisation of the haemoglobin under hypoxia conditions and this promotes red blood cell sickling. Inhibition of sickle cell haemoglobin polymerization is one of the areas of focus in the management of SCA. The present study is on the sickle cell haemoglobin polymerization of brown and green leaves of Carica papaya. The brown leaves are usually richer in phenolic constituents than the green leaves as the plant would have passed into the dying brown leaves certain unwanted metabolites which may be those required for medicinal purposes [1]. Materials and methods This study was aimed at comparing the antisickling properties of the crude aqueous extract, crude methanol extract and fractions of dead brown and fresh green leaves of C. papaya using n-phenylalanine and normal saline as positive and negative controls respectively. The method used was the sickle cell haemoglobin polymerization inhibition experiment measured with the UV spectrophotometer [2]. Results and Discussion The results obtained showed that crude aqueous extracts of both the green and brown leaves exhibited high level of inhibition of HbS polymerization of 97.76%, 93.25% and 95.89%; 97.93%, 97.89% and 95.84% at all concentrations - 200mg/ ml, 100mg/ml, 50mg/ml respectively which compared favourably and significantly (pChloroform>Ethyl acetate> water. The results obtained in this study showed that the extracts exhibited the potential of inhibiting polymerization of sickle cell haemoglobin thus they would be very beneficial in the management of sickle cell disease. References 1. Sofowora A. (2008) Medicinal Plants and Traditional Medicine in Africa. Spectrum Book, Ibadan Nigeria Ltd. 3rd Edn. p.91. 2. Noguchi, C.T. and Schechter, A.N. (1985). Sickle haemoglobin polymerization in solution and in cells. Ann. Rev. Biophyschem. 14: 239-246
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PP-205 Bimolecular compounds on the basis of guaianolides and their biological activity A.S. Kishkentaeva, B.A. Abdygalymova, R.B. Seydakhmetova, G.A. Atazhanova, S.M. Adekenov
JSC “International research and production holding “Phytochemistry”, Republic of Kazakhstan, Karaganda,
[email protected]
Introduction Among the most perspective directions of synthesis of nitrogen containing compounds on the basis of sesquiterpene lactones is the amination with primary and secondary amines via the aza-Michael reaction, which proceeds regio- and stereoselectively and only to the conjugate double bond of γ-lactone cycle. Sesquiterpene lactones containing a nitrogen atom show an antitumor effect and antibacterial activity. Materials and methods Thin-layer chromatography, physicochemical methods (IR, UV, 1Н, 13С NMR, two-dimensional NMR 1Н-1Н, 13С-1Н), elemental and X-ray analyses. Results and discussion Due to the fact that the molecules of sesquiterpene lactones of arglabin 1 and grosheimin 2 have a highly-reactive electrophilic center, exomethylene group in lactone cycle that is sensitive to the attack of nucleophiles, the amination reaction with a secondary alicyclic amine, alkaloid cytisine 3 possessing a high pharmacological activity, was carried out. As the result, new bimolecular derivatives 4, 5 on the basis of arglabin and grosheimin with good yields were obtained. The structure of the molecules of new obtained compounds 4, 5 was determined on the basis of physicochemical constants and spectral data. The stereochemistry of the crystalline structure 5 was studied by X-ray method (see figure 1).
H
O
O
OH
H
H
O
O
O
O N
N
4
O
O N
N
Figure 1 – Spatial structure of molecule 5
5
During the study of biological activity of obtained compounds it was revealed that the compound 4 has cytotoxic activity against larvae of the marine crustacean Artemia salina (Leach) and weak antibacterial activity against grampositive strain of Staphylococcus aureus, and also shows toxicity on different types of cell cultures (lamb kidneys, vero cells, lamb testicles). And the compound 5 shows moderately expressed antimicrobial activity against gram-positive strains of Staphylococcus aureus and Bacillus subtilis, and shows weak anti-inflammatory effects on a model of acute exudative reaction.
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PP-206 Chemical composition and biological activity of Artemisia essential oils G.А. Atazhanova
JSC “International research and production holding “Phytochemistry”, Republic of Kazakhstan, Karaganda,
[email protected]
Introduction The genus wormwood (Artemisia L.) prevails in all geographical and ecological zones and includes over 500 species. From 82 species of wormwood growing on the territory of the Republic of Kazakhstan, there are some valuable essential oil plants. In terms of searching for potential sources of biologically active compounds we studied the chemical composition of essential oils and their biological activity of 14 species of the genus Artemisia in the last three years. Materials and methods Hydrodistillation, supercritical carbon dioxide and microwave extraction, gas-liquid chromatography-mass spectrometry Results and discussion The chemical composition of essential oils isolated from aerial parts of 14 species of Artemisia from Kazakhstan – Artemisia abrotanum L., Artemisia aralensis Krasch., Artemisia arenaria DC, Artemisia ferganensis Krasch. ex. Poljak., Artemisia halophila Krasch., Artemisia heptopotamica Poljakov., Artemisia Кelleri Krasch., Artemisia marschalliana Spreng., Artemisia nitrosa Weber., Artemisia saissanica (Krasch.) Poljak ex Filat., Artemisia serotina Bunge, Artemisia terrae-albae Krasch., Artemisia turanica Krasch., Artemisia valida Krasch. et Poljak., was investigated by chromatographymass spectrometry. A total of 140 components were identified accounting for 71.0–98.8% of the oil composition. High contents of 1,8-cineole (21.8–42.6%) were found in Artemisia turanica Krasch. and Artemisia terrae-albae Krasch. оils. High contents of camphor (15.9–37.3%) were found in Artemisia ferganensis Krasch. ex. Poljak., Artemisia heptopotamica Poljakov, Artemisia saissanica (Krasch.) Poljak ex Filat., Artemisia terrae-albae Krasch., Artemisia turanica Krasch., Artemisia valida Krasch. et Poljak. oils. The contents of β-thujone (18.1 – 90.2%) were found in Artemisia ferganensis Krasch. ex. Poljak., Artemisia abrotanum L. The oil of Artemisia serotina Bunge was also characterized by a high content of oxygenated sesquiterpenes with a 5-ethenyltetrahydro-5-methyl-2-furanyl moiety, of which davanone (48.76%) was the main component identified. Artemisia halophila Krasch yielded an oil rich in β-mircene (10.7%) and 3-carene (19.0%). Artemisia aralensis Krasch oil was characterized by high amounts of trans-α-bisabolene (40.4%) Artemisia Кelleri Krasch. oil was characterized by high amounts of (Z)- β-ocimene (15.2%) and α-humulene (15.8%). Conclusion Furthermore biological screening of obtained essential oils, basic components and its derivatives was conducted in regard of antibacterial, anti-inflammatory, phagocytosis stimulating, analgesic, antiviral, cytotoxic activity. It was established that studied essential oils and its components have certain biological activity. Artemisia oils had inhibitory effects on the growth of bacteria (Escherichia coli, Staphylococcus aureus, and Staphylococcus epidermidis), yeast (Candida albicans), dermatophytes (Trichophyton rubrum, Microsporum canis) and Aspergillus niger.
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ADDENDUM
BIOACTIVE SECONDARY METABOLITES FROM THE SOIL AND MARINE-DERIVED FUNGI OF THE GENUS NEOSARTORYA Anake Kijjoa
Instituto de Ciências Biomédicas Abel Salazar and CIIMAR, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal; E-mail:
[email protected]
Higher fungi have been used not only as an alternative medicine remedy to promote health and longevity for people in many parts of the world since ancient times [1] but also as sources of antibiotics, immunosuppressive and antilipidemic drugs in modern medicine [2]. Nowadays there is an increasing public interest in the secondary metabolites of higher fungi for discovering new drugs or lead compounds. Besides traditional terrestrial fungi, scientists are now paying more attention to marine-derived fungi as sources of interesting bioactive compounds for pharmaceutical, neutraceutical and agricultural applications. So far, more than one thousand unique molecular structures have been discovered from marine-derived fungi. Several reviews on marine fungi have shown that a variety of secondary metabolites isolated from marine-derived fungi had not been found in terrestrial fungi, and these metabolites possibly act as a chemical defense, enabling marine-derived fungi to survive competition with native microorganisms. Thus, marine-derived fungi, which successfully fostered their armamentarium against bacterial competitors for millions of years, can be considered as a potential source of antibiotics [3]. One of the interesting fungal genera is Neosartorya which produces a variety of bioactive secondary metabolites. For these reasons we have investigated the secondary metabolites from the cultures of several species of the soil and marine-derived fungi of this genus in order to compare their chemical profiles as well as to evaluate their biological activities. Now we report the results of our chemical investigation of the culture of the soil-derived N. glabra, N. pseudofischeri [4], N. siamensis [5], N. fischeri, and the marine-derived N. paulistensis, N. laciniosa and N. tsunodae [6], well as the in vitro antitumor activity on human tumor cell lines, and the antibacterial and antibiofilm activities against the multi-drug resistant strains of the secondary metabolites isolated from these fungi. ACKNOWLEDGEMENTS This work was partially supported by the Project MARBIOTECH (reference NORTE-07-0124-FEDER-000047) within the SR&TD Integrated Program MARVALOR - Building research and innovation capacity for improved management and valorization of marine resources, supported by the Programa Operacional Regional do Norte (ON.2 – O Novo Norte). REFERENCES 1. Zhong JJ, Xiao JH. Adv Biochem Eng Biotechnol 2003; 113: 79-150. 2. Aly AH, Debbab A, Proksch P. Fungal Diversity 2001; 50: 3-19. 3. Fenical W, Jensen PR. Marine microorganisms: a new biomedical resource. In Marine Biotechnology; Attaway, D. H.; Zaborsky, O. R.; Eds.; Plenum Press, New York, 1993, Vol 1, pp 2419-2457. 4. Eamvijarn A, Kijjoa A, Bruyère C, Mathieu V, Manoch L, Lefranc F, Silva A, Kiss R, Herz W. Planta Medica 2012, 78: 1767-1776. 5. Buttachon S, Chandrapatya A, Manoch L, Silva A, Gales L, Bruyère C, Kiss R, Kijjoa A. Tetrahedron 2012, 68: 3253-3262. 6. Eamvijarn A, Gomes NM, Dethoup T, Buaraung J, Manoch L, Silva A, Pedro M, Marini I, Roussis V, Kijjoa A. Tetrahedron 2013, 69: 8583-8591.
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AUTHOR INDEX Abbaskhan T. . . . . . . . . . . . . . . . 205,207,209
Aoumar W.. . . . . . . . . . . . . . . . . . . . . . . . 181
Botirov E.Kh. . . . . . . . . . . . . . . . . . . . . 24,171
Abdellaoui K. . . . . . . . . . . . . . . . . . . . . . . 181
Aripova D.Sh.. . . . . . . . . . . . . . . . . . . . . . 140
Bouhaik S.. . . . . . . . . . . . . . . . . . . . . . . . . 181
Abdolhossein R.. . . . . . . . . . . . . . . . . . . . 247
Aripova S.F.. . . . . . . . . . . . . . . . . 139,140,141
Boulanouar A. . . . . . . . . . . . . . . . . . . . . . 269
Abdukhomidova F. . . . . . . . . . . . . . . . . . 152
Arslan A.M.. . . . . . . . . . . . . . . . . . . . . . . . 194
Bounar R. . . . . . . . . . . . . . . . . . . . . . . . . . 103
Abdukulov Z.U.. . . . . . . . . . . . . . . . . . . . . 116
Arslan I.. . . . . . . . . . . . . . . . . . . . 106,172,194
Brouard I.. . . . . . . . . . . . . . . . . . . . . . 100,185
Abdulkarim A.. . . . . . . . . . . . . . . . . . . . . . 155
Asilbekova D.T. . . . . . . . . . . . . . . . . . 23,91,92
Bulut F. . . . . . . . . . . . . . . . . 217,218,219,220
Abdulla R.. . . . . . . . . . . . . . 227,232,237,242
Aslım B.. . . . . . . . . . . . . . . . . . . . . . . . . . . 216
Cathrine L. . . . . . . . . . . . . . . . . . . . . . . . . 257
Abdullaev N.. . . . . . . . . . . . . . . . . . . . 117,118
Asrarov M.I. . . . . . . . . . . . . . . . . . . . . . . . 258
Celik A. . . . . . . . . . . . . . . . . . . . . . . . . . . . 172
Abdullaev N.D.. . . . . . 23,51,62,142,151,174
Atazhanova G.A.. . . . . . . . . . . . . 146,276,277
Chaher N.. . . . . . . . . . . . . . . . . . . . . . . . . 193
Abdullaeva R.Kh. . . . . . . . . . . . . . . . . . . . . 83
Atlı Ö. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 266
Chavasiri W. . . . . . . . . . . . . . . . . . . 98,99,186
Abdumijit A.. . . . . . . . . . . . . . . . . . . . . . . 226
Atmani D.. . . . . . . . . . . . . . . . . . . . . . . 47,193
Chefrour A.. . . . . . . . . . . . . . . . . . . . . . . . 264
Abdurahmonov B.A. . . . . . . . . . . . . . . . . 138
Ayad-Loucif W.. . . . . . . . . . . . . . . . . . . . . 191
Chelghoum M.. . . . . . . . . . . . . . . . . . . . . . 94
Abdurazakov A.Sh.. . . . . . . 157,158,159,160
Ayas F.. . . . . . . . . . . . . . . . . . . . . . . . . 195,196
Chen G.. . . . . . . . . . . . . . . . . . . . . . . 84,85,86
Abdurrahman A.. . . . . . . . . . . . . . . . . . . . 194
Ayaz F.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 262
Chen H.. . . . . . . . . . . . . . . . . . . . . . . . . . . 234
Abdygalymova B.A. . . . . . . . . . . . . . . . . . 276
Ayibieke A.. . . . . . . . . . . . . . . . . . . . . . . . . 87
Chen Q . . . . . . . . . . . . . . . . . . . . . . . . . . . 240
Abeuova S.B. . . . . . . . . . . . . . . . . . . . . . . . 78
Ayubic A.. . . . . . . . . . . . . . . . . . . . . . . . . . 237
Chen X.. . . . . . . . . . . . . . . . . . . . . . . . . . . 244
Ablajan T. . . . . . . . . . . . . . . . . . . . . . . . . . 225
Azamatov A.A.. . . . . . . . . . . . . . . . . . 132,134
Chenafa A. . . . . . . . . . . . . . . . . . . . . . . . . . 94
Ablikim K.. . . . . . . . . . . . . . . . . . . . . . . 27,242
Azevedo S.B.. . . . . . . . . . . . . . . . . . . . . . . 213
Chun W. . . . . . . . . . . . . . . . . . . . . . . . . . . 161
Ablikim U.. . . . . . . . . . . . . . . . . . . . . . . . . 227
Azib L.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 193
Chunting L.. . . . . . . . . . . . . . . . . . . . . . . . 227
Aboee-Mehrizi F.. . . . . . . . . . . . . . . . . . . 247
Azimov U.N.. . . . . . . . . . . . . . . . . . . . . . . 197
Çelik M.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 97
Abudujilili A.. . . . . . . . . . . . . . . . . . . . . . . 260
Azimova N.A. . . . . . . . . . . . . . . . . . . . . . . . 82
Çınar A.. . . . . . . . . . . . . . . . . . . . . . . . . . . 195
Abudukerimu A.. . . . . . . . . . . . . . . . . . . . 222
Azimova Sh.S.. . . . . . . . . . . . . . . . . . . . 15,180
Çulhaoğlu B.. . . . . . . . . . . . . . . . . . . . . . . 223
Abudurexiti A. . . . . . . . . . . . . . . . . . . . . . 252
Azizov U.M.. . . . . . . . . . . . . . . . . . . . . . 58,165
da Silva L.S. . . . . . . . . . . . . . . . . . . . . . . . 213
Abudureyimu M. . . . . . . . . . . . . . . . . . . . 222
Azizova M.A.. . . . . . . . . . . . . . . . . . . . 135,136
Daminov B.T. . . . . . . . . . . . . . . . . . . . . . . 107
Abula A. . . . . . . . . . . . . . . . . . . . . . . . . . . 260
Azzedine S.R. . . . . . . . . . . . . . . . . . . . . . . 185
Dan G.. . . . . . . . . . . . . . . . . . . . . . . . . 228,232
Acheuk F. . . . . . . . . . . . . . . . . . . . 74,181,253
Bachtiar A. . . . . . . . . . . . . . . . . . . . . . . . . 119
Dawuti G.. . . . . . . . . . . . . . . . . . . . . . . . . 260
Adam B. A.. . . . . . . . . . . . . . . . . . . . . . . . 179
Bani B.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 262
Debbache-Benaida N.. . . . . . . . . . . . . . . 193
Adaramoye O. . . . . . . . . . . . . . . . . . . . . . 183
Baser K.H.C..4,16,22,23,59,83,90,91,92,93,96,97,104,147
Demirci B..16,73,80,97,154,177,221,238,246,250,251,262,272
Adegun A. A. . . . . . . . . . . . . . . . . . . . . . . 148
Baysal M. . . . . . . . . . . . . . . . . . . . . . . . . . 272
Demirci F. . . . . . . . . . . . . . . . 59,250,266,272
Adekenov S.M.. . . . . . . . . . . . . . 146,176,276
Bazylak G.. . . . . . . . . . . . . . . . . . . . . . . . . . 72
Demirtas I. . . . . . . . . . 101,217,218,219,220
Adesegun, S. A. . . . . . . . . . . . . . . . . . . . . 148
Begimova D.I. . . . . . . . . . . . . . . . . . . 129,130
Denisenko V.A.. . . . . . . . . . . . . . . . . . . . . . 81
Adıgüzel N.. . . . . . . . . . . . . . . . . . . . . . . . 262
Behcet L.. . . . . . . . . . . . . . . 217,218,219,220
De-Qiang D. . . . . . . . . . . . . . . . . . . . . . 42,105
Adizov Sh.. . . . . . . . . . . . . . . . . . . . 52,64,122
Bekri M. . . . . . . . . . . . . . . . . . . . . . . . 162,226
Dina A.K.. . . . . . . . . . . . . . . . . . . . . . . . . . 193
Afiyatullov Sh.Sh. . . . . . . . . . . . . . . . . . 31,81
Belaid M.. . . . . . . . . . . . . . . . . . . . . . . . . . 253
Dinç M.. . . . . . . . . . . . . . . . . . . . . . . . . . . 251
Agzamova M.A. . . . . . . . . . . . . . . 46,134,163
Belkassam A. . . . . . . . . . . . . . . . . . . . . . . 103
Djouahra-Fahem D.. . . . . . . . . . . . . . . . . . 74
Ahmadu A.A. . . . . . . . . . . . . . . . . . . . . . . 155
Belleili M.. . . . . . . . . . . . . . . . . . . . . . . . . 261
Doğu S.. . . . . . . . . . . . . . . . . . . . . . . . . . . 251
Ahmedov V.N.. . . . . . . . . . . . . . . . . . . 24,163
Benabdelaziz I.. . . . . . . . . . . . . . . . . . . . . 257
dos Santos A.L.. . . . . . . . . . . . . . . . . . . . . 213
Aibai S. . . . . . . . . . . . . . . . . . . . . . . . . 188,260
Benayache F.. . . . . . . . . . . . 100,102,185,273
Duman H.. . . . . . . . . . . . . . . . . . . . . . . . . 216
Aini M. . . . . . . . . . . . . . . . . . . . . . . . . . . . 228
Benayache S. . . . . . . . . . . . 100,102,185,273
Duran A.. . . . . . . . . . . . . . . . . . . . . . . . . 93,97
Aisa H.A.. . 3,32,44,61,123,162,188,222,225,156,157
Benaziza D. . . . . . . . . . . . . . . . . . . . . . . . 253
Duru M.E.. . . . . . . . . . . . . . . . . . . . . . . . . 103
Akhmedova Kh. Kh.. . . . . . . . . . . . . . . . . 164
Benlarbi L.. . . . . . . . . . . . . . . . . . . . . . . . . 269
Dusmatova D.E. . . . . . . . . . . . . . . . . . 166,167
Ali Z. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 206
Benmekhebi L.. . . . . . . . . . . . . . . . . . . . . 102
Dündar E.. . . . . . . . . . . . . . . . . . . . . . . . . 221
Al-Massarani S.. . . . . . . . . . . . . . . . . . . . . 184
Benmoussa M.T.. . . . . . . . . . . . . . . . . . . . 264
Dzakhangirov F.N. . . . . . . . . . . . . 45,132,149
Altıntaş A.. . . . . . . . . . . . . . . . . . . . . . . . . 221
Bennadja S.. . . . . . . . . . . . . . . . . . . . . 108,215
Edirs S. . . . . . . . . . . . . . . . . . . . . . . . . . . . 225
Ameddah S. . . . . . . . . . . . . . . . . . . . . . . . 185
Bensisaid H. . . . . . . . . . . . . . . . . . . . . . . . 261
Egamova F.R. . . . . . . . . . . . . . . . . . . . . . . 168
Amel M. . . . . . . . . . . . . . . . . . . . . . . . . . . 108
Bentamene A.. . . . . . . . . . . . . . . . . . . . . . 100
El Dib R.. . . . . . . . . . . . . . . . . . . . . . . . . . . 184
Aminov S.D. . . . . . . . . . . . . . . . . . . . . . . . 156
Benzina F.. . . . . . . . . . . . . . . . . . . . . . . . . 253
Elgoutni D. . . . . . . . . . . . . . . . . . . . . . . . . . 94 Elmuradov B.Zh.. . . . . . . . . . . 10,18,125,132
Amira O.. . . . . . . . . . . . . . . . . . . . . . . 108,215
Bicha S.. . . . . . . . . . . . . . . . . . . . . . . . 100,102
Amiri S.. . . . . . . . . . . . . . . . . . . . . . . . . . . 181
Bielinska I.. . . . . . . . . . . . . . . . . . . . . . . . . . 72
Ergasheva M.J.. . . . . . . . . . . . . . . . . . . . . . 82
Amirsaidov T.E.. . . . . . . . . . . . . . . . . . . . . 203
Bitiş L.. . . . . . . . . . . . . . . . . . . . . . . . . . 22,224
Erken S.. . . . . . . . . . . . . . . . . . . . . . . . . . . 245
Amrani A.. . . . . . . . . . . . . . . . . . . . . . 100,273
Bobakulov Kh. . 23,65,109,115,117,118,142,151,153,174,175,235
Eshbakova K.A . . . . 44,51,123,124,128,258,259
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Eshimbetov A.G. . . . . . . . . . . . . . . . . . 62,157
Ismailova D.S.. . . . . . . . . . . . . . . . . . . . . . 112
Kirichuk N.N. . . . . . . . . . . . . . . . . . . . . . 31,81
Fadipe V.. . . . . . . . . . . . . . . . . . . . . . . . . . 256
Ismailova K.M.. . . . . . . . . . . . . . . . . . . . . 116
Kishkentaeva A.S. . . . . . . . . . . . . . . . . . . 276
Fazouane F.. . . . . . . . . . . . . . . . . . . . . . . . . 74
Ismailova M.G.. . . . . . . . . . . . . . . 77,129,130
Klavina L.. . . . . . . . . . . . . . . . . . . . . . . . . . 210
Flamini G.. . . . . . . . . . . . . . . . . . . . . . . . . 103
İbrahim D.. . . . . . . . . . . . . . 217,218,219,220
Klochkov V.V.. . . . . . . . . . . . . . . . . . . . . . . . 79
Forgo P.. . . . . . . . . . . . . . . . . . . . . . . . . . . 268
Jackob M.R. . . . . . . . . . . . . . . . . . . . . . . . 206
Kodirova D.R.. . . . . . . . . . . . . . . . . . . . . . 270
Fu Y.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85
Jalilov Kh.K.. . . . . . . . . . . . . . . . . . . . . 135,136
Komilov B.J. . . . . . . . . . . . . . . . . . . . . . 51,259
Gafurov D.A.. . . . . . . . . . . . . . . . . . . . 169,192
Jianbo L.. . . . . . . . . . . . . . . . . . . . . . . . . . 228
Kotukhov Y.. . . . . . . . . . . . . . . . . . . . . . . . . 90
Gafurova D.A.. . . . . . . . . . . . . . . . . . . 169,192
Jiang-yang G. . . . . . . . . . . . . . . . . . . . . . . 222
Köse Y.B.. . . . . . . . . . . . . . . . . 68,73,154,238
Galstyan A.S.. . . . . . . . . . . . . . . . . . . . . . . . 79
Jurakulov Sh.N.. . . . . . . . . . . . . . . . . . . . . 180
Kubmarawa D. . . . . . . . . . . . . . . . . . . . . . . 76
Gao J. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 240
Kaci K.A. . . . . . . . . . . . . . . . . . . . . . . . . . . . 74
Kuchkarova N.N.. . . . . . . . . . . . 113,133, 173
Gao Y. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 255
Kadirova D.B. . . . . . . . . . . . . . . . . . . . 139,141
Kurbanbaeva A.E. . . . . . . . . . . . . . . . 124,128
Ghadbane M.. . . . . . . . . . . . . . . . . . . . . . 103
Kamalov L.S.. . . . . . . . . . . . . . . . . . . . . . . 139
Kurbanov U.Kh. . . . . . . . . . . . . . . 65,109,120
Glushenkova A.I. . . . . . . . . . . . . . . . . . . . 152
Kamel M. . . . . . . . . . . . . . . . . . . . . . . . . . 101
Kurbanova E.R. . . . . . . . . . 112,113,133,173
Go A.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 275
Kamil W.. . . . . . . . . . . . . . . . . . . . . . . 235,236
Kushiev Kh.. . . . . . . . . . . . . . . . . . . . . . . . 116
Golparvar A.R. . . . . . . . . . . . . . . . . . . 211,214
Kara B.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 104
Kushnarenko S. . . . . . . . . . . . . . . . . . . . . . 90
Gousami Z.. . . . . . . . . . . . . . . . . . . . . . . . 264
Kara I. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 104
Kustova T.. . . . . . . . . . . . . . . . . . . . . . . . . . 89
Gouri A.. . . . . . . . . . . . . . . . . . . . . . . . . . . 261
Karakaya S.. . . . . . . . . . . . . . . . . . . . . . . . 250
Küçük S. . . . . . . . . . . . . . . . . . . . . . . . . . . . 80
Göger F.. . . 68,83,90,91,96,104,147,221,238
Karasholakova L.. . . . . . . . . . . . . . . . . . . . . 90
Küçükboyacı N.. . . . . . . . . . . . . . . . . . . . . 262
Göger G.. . . . . . . . . . . . . . . . . . . . . . . . 97,272
Karimov A.M. . . . . . . . . . . . . . . . . . . . . . . 171
Kwon Y.. . . . . . . . . . . . . . . . . . . . . . . . . . . 161
Gören A.C. . . . . . . . . . . . . . . . . . . . . . . . . 190
Karimov R.K.. . . . . . . . . . . . . . . . . . . . . . . . 62
Lajter I.. . . . . . . . . . . . . . . . . . . . . . . . . . . 268
Guoan Z.. . . . . . . . . . . . . . . . . . . . . . . 228,232
Karl T.W. . . . . . . . . . . . . . . . . . . . . . . . . . . 222
Lakhdar D.. . . . . . . . . . . . . . . . . . . . . . . . . 101
Gusakova S.D.. . . . . . . . . . . . . . . . . . . . 26,143
Karpenyuk T.. . . . . . . . . . . . . . . . . . . . . . . . 89
Lakhdari W.. . . . . . . . . . . . . . . . . . . . . . . . 181
Gülbağ F.. . . . . . . . . . . . . . . . . . . . . . . . . . 245
Kartal M.. . . . . . . . . . . . . . . . . . . . . . . . . . 216
Lakhel S.. . . . . . . . . . . . . . . . . . . . . . . . . . 264
Günbatan T. . . . . . . . . . . . . . . . . . . . . . . . 246
Kasim G.. . . . . . . . . . . . . . . . . . . . . . . . . . 248
Lardjam A. . . . . . . . . . . . . . . . . . . . . . . . . 267
Gürbüz I.. . . . . . . . . . . . . . . . . . . . . . . 246,279
Kasimova T.D.. . . . . . . . . . . . . . . . . . . 169,192
Leão L.A.S. . . . . . . . . . . . . . . . . . . . . . . . . 213
Hadef Y.. . . . . . . . . . . . . . . . . . . . . . . . 261,264
Kaya A. . . . . . . . . . . . . . . . . . . . . . . . . . . . 251
León F.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 185
Hadipanah A.. . . . . . . . . . . . . . . . . . . 211,214
Kebbouche-Gana S.. . . . . . . . . . . . . . . . . 253
Leshchenko E.V. . . . . . . . . . . . . . . . . . . . . . 81
Hafdi S.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 94
Kerkatou M.. . . . . . . . . . . . . . . . . . . . . . . 185
Levkovich M.. . . . . . . . . . . . . . . . . . . . 10,118
Hairani R. . . . . . . . . . . . . . . . . . . . . . . . . . 186
Khadjieva U.A. . . . . . . . . . . . . . . . . . . . . . 165
Li G.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271
Haliloğlu Y. . . . . . . . . . . . . . . . . . . . . . . . . . 96
Khajibaev T.A.. . . . . . . . . . . . . . . . . . . . . . 144
Li X.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 239
Hamada H.. . . . . . . . . . . . . . . . . . . . . 243,257
Khalilov R.M. . . . . . . . . . . . . . . . . 55,144,145
Li Y. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 231
Han C.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85
Khalmirzayeva A.I.. . . . . . . . . . . . . . . . . . 120
Liu Y. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 225
Hatipoğlu S.D.. . . . . . . . . . . . . . . . . . . . . . 190
Khan I.A.. . . . . . . . . . . . . . . . . . . . . . . . 16,206
Liu Z.. . . . . . . . . . . . . . . . . . . . . . . . . . 239,244
Hayder G.. . . . . . . . . . . . . . . . . . . . . . . . . 212
Khashimova Z.S.. . . . . . . . . . . . . . . . . . 15,180
Lodochnikova O.A.. . . . . . . . . . . . . . . . . . . 79
Heinze T.. . . . . . . . . . . . . . . . . . . . . . . . . . 209
Khelaf R.. . . . . . . . . . . . . . . . . . . . . . . . . . 102
Lynda G. . . . . . . . . . . . . . . . . . . . . . . . . . . 243
Helil S.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 208
Khidyrova N.K.. . . . . . . . . . 111,114,115,116
Ma H. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 234
Himit H.. . . . . . . . . . . . . . . . . . . . . . . . . . . 235
Khitri W. . . . . . . . . . . . . . . . . . . . . . . . . . . 267
Ma L.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 239
Hocine L.. . . . . . . . . . . . . . . . . . . . . . . . . . 101
Khodjaniyazov Kh.U. . . . . . . . . . . . . . . . . 114
Madjidova Y.N.. . . . . . . . . . . . . . . . . . . . . 107
Houria B.. . . . . . . . . . . . . . . . . . . . . . . . . . 265
Khujaev V.U. . . . . . . . . . . . . . . . . . . . . . . . 140
Madjitova D.U. . . . . . . . . . . . . . . . . . . . . 165
Huang Y. . . . . . . . . . . . . . . . . . . . . . . . . . . 239
Khushbaktova Z.A.. 39,62,163,164,168,170,182
Madrahimov Sh.N.. . . . . . . . . . . . . . . . . . 144
Ibragimov T.F.. . . . . . . . . . . . . . . . . . . 129,130
Khvan A.M.. . . . . . . . . . . . . . . . . . . . . 159,160
Madrakhimovа M.I.. . . . . . . . . . . . . . 138,145
Ibrahim, I. L.. . . . . . . . . . . . . . . . . . . . 178,179
Kılıç C.S.. . . . . . . . . . . . . . . . . . . . . . . . . . . 250
Magiatis P. . . . . . . . . . . . . . . . . . . . . . . . . 155 Mahfouf N.. . . . . . . . . . . . . . . . . . . . . . . . 215
Ibtissem B. . . . . . . . . . . . . . . . . . . . . . . . . 101
Kıran I.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 279
Ihara H.. . . . . . . . . . . . . . . . . . . . . . . . . . . 207
Kırımer N.. . . . . . . . . . . . . . . . . . . . . . . 37,147
Mahkamov H.M. . . . . . . . . . . . . . . . . . . . . 43
Ilgın S.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 272
Kidah M. I. . . . . . . . . . . . . . . . . . . . . . . . . . 76
Mahmud M.A. . . . . . . . . . . . . . . . . . . . . . 208
Inoyatova F.Kh.. . . . . . . . . . . . . . . . . . . . . 107
Kijjoa A,. . . . . . . . . . . . . . . . . . . . . . . . . . . 279
Majidov K.H.. . . . . 197,198,199,200,201,203
Isaev I.M. . . . . . . . . . . . . . . . . . . . . . . . 46,134 Iscan G.. . . . . . . . . . . . . . . . . . . . . 68,154,238 Iskandarov S.I. . . . . . . . . . . . . . . . . 58,78,165 Iskanderov A.N.. . . . . . . . . . . . . . . . . . . . . 78 Islamovа J.I. . . . . . . . . . . . . . . . . . . . . . . . 164
SCNC 2015 Abstracts
Kim H.P.. . . . . . . . . . . . . . . . . . . . . . . . . . . 161 Kim M.A.. . . . . . . . . . . . . . . . . . . . . . . 129,161 Kim M.J. . . . . . . . . . . . . . . . . . . . . . . . . . . 161 Kingkaew K. . . . . . . . . . . . . . . . . . . . . . . . . 98 Kirane-Amrani L. . . . . . . . . . . . . . . . . . . . 254
281
Majidova N.K.. . . . . . . . . . . . . . . . . . . . . . 201 Makhloufi A. . . . . . . . . . . . . . . . . . . . . . . 269 Makhmudov U.S.. . . . . . . . . . . . . . . . . . . 121 Makhmudova B.Sh. . . . . . . . . . . . . . . . . . 157 Makhmudova M.M.. . . . . . . . . . . . . . . . 53,54
Malik A.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 87
Ogun O.. . . . . . . . . . . . . . . . . . . . . . . . . . . 275
Samuel B.B. . . . . . . . . . . . . . . . . . . . . . . . 183
Malikova M.Kh. . . . . . . . . . . . . . . . . . . . . 164
Oke-Altuntas F.. . . . . . 216,217,218,219,220
Sanches E.A. . . . . . . . . . . . . . . . . . . . . . . 213
Malyer H. . . . . . . . . . . . . . . . . . . . . . . . . . 147
Okhunov I.I. . . . . . . . . . . . . . . . . . . . . . . . 140
Sanoev Z.I. . . . . . . . . . . . . . . . . . . . . . . . . 134
Mamadalieva N.. . . . . . . . . . . . . . . . . . 12,117
Okmanov R.Y.. . . . . . . . . . . . . . . . . . . . . . 141
Sarri D. . . . . . . . . . . . . . . . . . . . . . . . . . . . 185
Mamatkhanov A.U. . . . . . . . . . . . . . . . . . 137
Oltiev A.T.. . . . . . . . . . . . . . . . . . . . . . . . . 202
Satari A.H.. . . . . . . . . . . . . . . . . . . . . . . . . 204
Mamatkhanova M.A.. . . . . . . . . 137,145,164
Omarova A.T. . . . . . . . . . . . . . . . . . . . . . . . 78
Seidakhmetova R.B.. . . . . . . . . . . . . . . . . 146
Mamatkulova N.M. . . . . . . 113,115,116,173
Omonturdiev S.Z.. . . . . . . . . . . . . . . . . . . 259
Seiilgazy M.. . . . . . . . . . . . . . . . . . . . . . . . 229
Mamatov M.M. . . . . . . . . . . . . . . . . . . . . 203
Opoku A.R.. . . . . . . . . . . . . . . . . . . . . . . . 256
Shabier G.. . . . . . . . . . . . . . . . . . . . . . . . . 162
Mann A. . . . . . . . . . . . . . . . . . . . . . . . 178,179
Otmani K.. . . . . . . . . . . . . . . . . . . . . . . . . 102
Shagal M.H. . . . . . . . . . . . . . . . . . . . . . . . . 76
Mansur S. . . . . . . . . . . . . . . . . . . 227,237,255
Ouibrahim A. . . . . . . . . . . . . . . . . . . . 108,215
Shakhidoyatov Kh.M. . . . . . . . . . 10,114,115
Mar J.M.. . . . . . . . . . . . . . . . . . . . . . . . . . 213
Özek G.. . . . . . . . . 23,83,90,91,92,93,96,104
Shamy’anov I.D. .50,150,153,166,167,171,174,175,189
Marchioni E.. . . . . . . . . . . . . . . . . . . . . . . 273
Özek T.. . . . . . . . . . . . . . . . 16,23,90,91,92,96
Shevchenko L.I. . . . . . . . . . . . . . . . . . . . . 164
Marczak L.. . . . . . . . . . . . . . . . . . . . . . . . . . 72
Özkan A.M.G.. . . . . . . . . . . . . . . . . . . . . . 246
Siddikov D.R. . . . . . . . . . . . . . . . . 151,189,48
Masoodi M. . . . . . . . . . . . . . . . . . . . . . . . 206
Özkan E.E.. . . . . . . . . . . . . . . . . . . . . . . . . 190
Skaltsounis A.L . . . . . . . . . . . . . . . . . . . . 155
Mat A.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 190
Özşen Ö.. . . . . . . . . . . . . . . . . . . . . . . . . . 266
Smaili T.. . . . . . . . . . . . . . . . . . . . . . . . . . . 103
Mazid R.. . . . . . . . . . . . . . . . . . . . . . . . . . 267
Öztürk G.. . . . . . . . . . . . . . . . . . . . . . . . . . . 97
Smina A.H. . . . . . . . . . . . . . . . . . . . . . . . . 265
Mebarki L.. . . . . . . . . . . . . . . . . . . . . . . . . 269
Öztürk M.. . . . . . . . . . . . . . . . . . . . . . . . . 103
Sobirova N.N.. . . . . . . . . . . . . . . . . . . . . . 200
Mejlumyan L.G. . . . . . . . . . . . . . . . . . . 60,263
Öztürk N. . . . . . . . . . . . . . . . . . . . . . . . . . 245
Sobolkova G.N.. . . . . . . . . . . . . . . . . . . 31,110
Melikuziev F.A. . . . . . . . . . . . . . . . . . 150,166
Özzambak M.E. . . . . . . . . . . . . . . . . . . . . 245
Sokhibova N.B.. . . . . . . . . . . . . . . . . . 131,132
Menad A. . . . . . . . . . . . . . . . . . . . . . . . . . 185
Pezzopane I.. . . . . . . . . . . . . . . . . . . . . . . 213
Soltani-Mazouni N. . . . . . . . . . . . . . . . . . 254
Merkhatuly N. . . . . . . . . . . . . . . . . . . . . . . 78
Ping Z.J.. . . . . . . . . . . . . . . . . . . . . . . . . . . 205
Song X. . . . . . . . . . . . . . . . . . . . . . . . . . . 85,86
Mikhailov S. . . . . . . . . . . . . . . . . . . . . . . . 205
Pislyagin E.A. . . . . . . . . . . . . . . . . . . . . . . . 81
Sotimov G.B.. . . . . . . . . . . . . . . . . . . . 137,138
Mirzaahmedova K.T.. . . . . . . . . . . . . . . . . 156
Poyraz I.E.. . . . . . . . . . . . . . . . . . . . . . . 80,245
Souilah A.. . . . . . . . . . . . . . . . . . . . . . . . . 102
Mirzaev Yu.R.. . . . . . . . . . . . . . . . . . . . . . 134
Pozilov M.K.. . . . . . . . . . . . . . . . . . . . . . . 258
Springe G.. . . . . . . . . . . . . . . . . . . . . . . . . 210
Mirzaeva Y.T.. . . . . . . . . . . . . . . . . . . . . . . 259
Qureshi M.N. . . . . . . . . . . . . . . . . . . . . . . 233
Startseva V.A. . . . . . . . . . . . . . . . . . . . . . . 79
Mohamadi S. . . . . . . . . . . . . . . . . . . . . . . 273
Radnaeva L.D.. . . . . . . . . . . . . . . . . . . . . 20,95
Sulaymanova G.H.. . . . . . . . . . . . . . . 199,202
Mohamed D. . . . . . . . . . . . . . . . . . . . . . . 265
Rakhimov M.N. . . . . . . . . . 198,200,201,202
Sultan G.. . . . . . . . . . . . . . . . . . . . . . . . . . 208
Mohammed B. . . . . . . . . . . . . . . . . . 243,257
Rakhimov Sh.B. . . . . . . . . . . . . . . . . . 121,127
Susilawati Y. . . . . . . . . . . . . . . . . . . . . . . . 119
Mongalo N.. . . . . . . . . . . . . . . . . . . . . . . . 256
Rakhimova Sh.Kh. . . . . . . . . . . . . . . . . . . 263
Suyarov A.A. . . . . . . . . . . . . . . . . . . . . . . 144
Movsumov I.S.. . . . . . . . . . . . . . . . . . . . . . 75
Rakhmanberdyeva R.K.. . . . . . . . . . . . 56,164
Syrov V.N.. . . . . 26,62,163,164,168,170,182
Muhitdinov B.. . . . . . . . . . . . . . . . . . . . . . 209
Ran X. . . . . . . . . . . . . . . . . . . . . . . . . . . 42,105
Şen A.. . . . . . . . . . . . . . . . . . . . . . . . . . 22,224
Mukarramov N.I.. . . . . . . . . 65,109,120,141
Randalova T.E. . . . . . . . . . . . . . . . . . . . . 20,95
Tabassum N.. . . . . . . . . . . . . . . . . . . . . . . 204
Mukasheva F.T. . . . . . . . . . . . . . . . . . . . . 146
Rasulova Kh.A. . . . . . . . . . . . . . . 107,142,270
Tadeja A.. . . . . . . . . . . . . . . . . . . . . . . . . . . 72
Mukhamatkhanova R.F.. . . . . . . . 50,166,167
Rebbas K. . . . . . . . . . . . . . . . . . . . . . . 102,103
Tamsampaoloet K.. . . . . . . . . . . . . . . . . . . 99
Mukhamedjanova D.V. . . . . . . . . . . . . . . 127
Renda G. . . . . . . . . . . . . . . . . . . . . . . . . . 249
Tan E.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 194
Mukhamedov I. . . . . . . . . . . . . . . . . . . . . 207
Ross S.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 89
Tan S.B.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
Mukhtar Imerhasan M.. . . . . . . . . . . . . . 208
Ruzimamat R.. . . . . . . . . . . . . . . . . . . . . . 240
Tanriseven M.. . . . . . . . . . . . . . . . . . . 195,196
Murodov J.S.. . . . . . . . . . . . . . . . . . . . . . . 203
Sabrina A.. . . . . . . . . . . . . . . . . . . . . . . . . 108
Tarfaya B. . . . . . . . . . . . . . . . . . . . . . . . . . 269
Musin R.Z.. . . . . . . . . . . . . . . . . . . . . . . . . . 79
Sadikov T. . . . . . . . . . . . . . . 157,158,159,160
Tashkhodzhaev B. . 64,121,122,139,167,189
Najib S.Z.. . . . . . . . . . . . . . . . . . . . . . . . . . 119
Sadykov A.Z.. . . . . . . . . . . . . . . . . 24,135,136
Tazir A. . . . . . . . . . . . . . . . . . . . . . . . . . . . 254
Ndanaimi A.. . . . . . . . . . . . . . . . . . . . . . . 178
Sagdiev N.J.. . . . . . . . . . . . . . . . . . . . . . . . . 88
Tekin M. . . . . . . . . . . . . . . . . . . . . . . . . . 83,96
Nebieridze V. . . . . . . . . . . . . . . . . . . . . . . 187
Sagdullaev Sh.Sh.. . . . . . . . . . . . . . . . . . . . . .
Тerenteva Е.О.. . . . . . . . . . . . . . . . . . . . . . 15
Nedji N.. . . . . . . . . . . . . . . . . . . . . . . . . . . 191 Nematov Kh.Sh.. . . . . . . . . . . . . . . . . . . . 263 Nigmatullaev A. M. . . . . . . . . . . . . . . . . . . 92 Nigmatullaev O.M.. . . . . . . . . . . . . . . . . . 110 Nishanbaev S.Z.. 150,151,153,166,174,175189 Normakhamatov N.. . . . . . . . . . 205,207,209 Nosov A.M. . . . . . . . . . . . . . . . . . . . . . . . 110 Nuritdinov B.S.. . . . . . . . . . . . . . 198,200,201 Ogay D.K. . . . . . . . . . . . . . . . . . . . . . . . . . 164
SCNC 2015 Abstracts
2,23,24,26,52,62,91,92,135,136,138,143,145,157,158,159,160,263
Sahraoui Z.F.. . . . . . . . . . . . . . . . . . . . . . . 267 Saidov A. Sh.. . . . . . . . . . . . . . . . . . . . . . . 126 Saidvaliev S.S.. . . . . . . . . . . . . . . . . . . . . . 203 Saitmuratova O.Kh.. . . . . . . . . . . . . . . . . . 88 Salah A.. . . . . . . . . . . . . . . . . . . . . . . . . . . 101 Salima B.. . . . . . . . . . . . . . . . . . . . . . . 108,215 Salimov B.T. . . . . . . . . . . . . . . . . . . . . . . 2,149 Saltan N.. . . . . . . . . . . . . . . . . . . . . . . . . . 177 Samira B.. . . . . . . . . . . . . . . . . . . . . . . . . . 265
282
Ting-xia D.. . . . . . . . . . . . . . . . . . . . . . . . . 222 Topçu G.. . . . . . . . . . . . . . . . . . . . . . . . . . 223 Toplan G.G.. . . . . . . . . . . . . . . . . . . . . . . . 190 Toshmatov Z.O. . . . . . . . . . . . . . . . . . . . . 123 Tosun G. . . . . . . . . . . . . . . . . . . . . . 41,66,249 Tseomashko N.Е. . . . . . . . . . . . . . . . . . . . 180 Tuerhong M.. . . . . . . . . . . . . . . . . . . . . . . 252 Tuerxun X.. . . . . . . . . . . . . . . . . . . . . . . . . . 88 Tuerxuntayi A. . . . . . . . . . . . . . . . . . . . . . 241
Turayeva S.M.. . . . . . . . . . . . . . . . . . . 113,173
Zemlyanskaya N.R.. . . . . . . . . . . . . . . . . . 156
Turgunov K.K. . . . . . . . . . . . 51,120,167,189
Zemmour L. . . . . . . . . . . . . . . . . . . . . . . . 267
Turgunov Ye.T.. . . . . . . . . . . . . . . . . . . . . . . 78
Zhang C. . . . . . . . . . . . . . . . . . . . . . . . . . . 244
Tursunhodjaev P.M.. . . . . . . . . . . . . . 169,192
Zhang J.. . . . . . . . . . . . . . . . . . . . . . . . 162,226
Tursunkhodjaeva F.M.. . . . 2,45,131,132,149
Zhao B. . . . . . . . . . . . . . . . . . . . . . . . . 235,236
Türk M.. . . . . . . . . . . . . . . . . . . . . . . . . . 83,96
Zhao H.. . . . . . . . . . . . . . . . . . . . . . . . . . . 255
Ulchenko N.T.. . . . . . . . . . . . . . . . . . . . . . 143
Zhao J.. . . . . . . . . . . . . . . . . . . . . . . . . . . 3,271
Umoh S.D.. . . . . . . . . . . . . . . . . . . . . . . . . 183
Zhao M.. . . . . . . . . . . . . . . . . . . . . . . . . . . 273
Urakov B.A. . . . . . . . . . . . . . . . . . . . . . . . 133
Zheng C. . . . . . . . . . . . . . . . . . . . . . . . . . . . 84
Usman A. . . . . . . . . . . . . . . . . . . . . . . . . . 148
Zhigzhitzhapova S.V.. . . . . . . . . . . . . . . . 20,95
Usmanov D.A.. . . . . . . . . . . . . . . . . . . . . 53,54
Zhijian L.. . . . . . . . . . . . . . . . . . . . . . . . . . 260
Usmanov P.B.. . . . . . . . . . . . . . . . . . . . . . 259
Zhou J.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87
Utegenova G.. . . . . . . . . . . . . . . . . . . . . . . 90
Zhou Q.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
Vinogradova V.I.. . . . . . . . . . . . . 121,125,126
Zhou X.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 84
Vlasova O.A.. . . . . . . . . . . . . . . . 113,133,173
Zhurakulov Sh.N.. . . . . . . . . . . . . . . . . . . 125
Vuran F.A.. . . . . . . . . . . . . . . . . . . . . . . . . 196
Ziyaev A. A.. . . . . . . . . . . . . . . . . . . . . . . . 112
Wang Y.. . . . . . . . . . . . . . . . . . . . . . . . . . . 230
Zukhurova G.V.. . . . . . . . . . . . . . . . . . . . . 157
Wardhana Y.W.. . . . . . . . . . . . . . . . . . . . . 119 Wondraczek H.. . . . . . . . . . . . . . . . . . . . . 209 Wu H. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 255 Wu S.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86 Xin X.. . . . . . . . . . . . . . . . . . . . . . . . . . 234,255 Xueling H.. . . . . . . . . . . . . . . . . . . . . . . . . 235 Yakubova F.T. . . . . . . . . . . . . . . . . . . . . . . . 88 Yakubova L.K. . . . . . . . . . . . . . . . . . . . . . . 182 Yasmina T.. . . . . . . . . . . . . . . . . . . . . . . . . 108 Yaylı B. . . . . . . . . . . . . . . . . . . . . . . . . . . . 249 Yaylı N. . . . . . . . . . . . . . . . . . . . . . . . . . . . 249 Ye Y.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 205 Yili A. . . . . . . . . . . . . . . . . . . . . . . 61,231,270 Yu S.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 42,105 Yu Z.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85 Yuldashev P. . . . . . . . . . . . . . . . . . . . . . . . 122 Yuldashev Sh.U.. . . . . . . . . . . . . . . . . . . . 143 Yuldasheva N.Kh.. . . . . . . . 52,63,64,162,182 Yunuskhodjaeva K.G.. . . . . . . . . . . . . . . . . 77 Yuqin L.. . . . . . . . . . . . . . . . . . . . . . . . . . . 232 Yur S.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 83 Yusifova J.Y.. . . . . . . . . . . . . . . . . . . . . . . . . 75 Yusupova S.M. . . . . . . . . . . . . . . . . . . . . . 168 Yusupova U.Y . . . . . . . . . . . . . . . . . . . . . 53,54 Yücer R.. . . . . . . . . . . . . . . . . . . . . . . . . . . 223 Zainutdinov U.N. . . . . . . . . . . . . . . . . . . . 152 Zakhidova L.T. . . . . . . . . . . . . . . . . . . . . . 182 Zakirov R.P.. . . . . . . . . . . . . 110,111,112,133 Zakirova U.T.. . . . . . . . . . . . . . . . . . . . . . . 114 Zama D.. . . . . . . . . . . . . . . . . . . . . . . . . . . 100 Zare A.. . . . . . . . . . . . . . . . . . . . . . . . . . . . 247 Zargar M.I. . . . . . . . . . . . . . . . . . . . . . . . . 204 Zavarzin I.V. . . . . . . . . . . . . . . . . . . . . . . . 110 Zellagui A. . . . . . . . . . . . . . . . . . . . . . . . . 103
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