Curso Quimica de Productos Naturales

CURSO QUIMICA QUIMICA DE PRODUCTOS NATURALES

CAPITULO I: CONCEPTOS BASICOS Los productos naturales se han dividido con cierta arbitrariedad en 02 grupos: metabolitos primarios y metabolitos secundarios:

METABOLITOS PRIMARIOS  

Producto del metabolismo general Ampliamente distribuidos en plantas y microorganismos (aminoácidos de proteínas comunes, monosacáridos, nucleótidos, ácidos carboxílicos, lipidos, vitaminas.)

METABOLITOS SECUNDARIOS Producto del metabolismo especial. Biosintetizados a partir de los metabolismos primarios. Distribución restringida restringida a ciertas plantas y microorganismos (a veces es característico de un género dado ó de una especie).Ejemplo: Flavonoides, Cumarinas, Saponinas, Terpenoides, Taninos, Alcaloides, etc.) Son compuestos químicos de estructura relativamente compleja.  



Los metabolitos secundarios es propio de una especie y se le conoce también como “Producto químico” o “Compuesto del químico”, hasta hoy se considera que los metabolitos secundarios no tienen una función definida en la especie, o un significado bioquímico, no se ha descubierto aún una función metabólica en la cual ellos intervienen, no tienen una utilidad aparente para la especie, que lo sintetiza, es decir no participan en su crecimiento y reproducción, por esos son considerados como artículos de lujo para la planta. Los metabolitos primarios, son comunes a todos los seres vivos y  participan en la actividad celular y se encuentran en todos los organismos vivos; por lo tanto son metabólicamente esenciales, en algunos casos los metabolitos primarios sirven como precursores de los metabolitos secundarios. A estos metabolitos se les conoce como productos bioquímicos es decir compuestos del bioquímico.

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Es necesario indicar en este punto que hasta la actualidad por ejemplo; que compuestos como el escualeno un triterpeno no común obtenido del aceite del hígado de tiburón considerado como metabolito secundario, y conocido como uno de los productos universalmente distribuido, es un participante fundamental en el metabolismo de los seres vivos, es decir que  probablemente que muchos de los compuestos orgánicos que qu e hoy en día se califican de “metabolito s secundarios” lleguen a ser reconocidos como actores principales de importantes funciones biológicas.

N

COOH

L- pr olina olina (amijnoacido (amijnoacido de pr oteinas)

N

COOH

metabolito primario L- pipecólico metabolitos secundarios

solo se encuentra en ciertas plant

BIOSINTESIS Todos los compuestos orgánicos, están constituidos por carbono e hidrogeno a menudo contienen oxigeno y nitrógeno y menos frecuentemente, azufre, fósforo, y halógenos. La formación de los productos naturales comienza con la fotosíntesis que tienen lugar en plantas superiores, algas y algunas bacterias. Es un proceso endotérmico que requiere de la luz solar. Aquellos organismos incapaces de absorber la luz obtienen su energía de la degradación de carbohidratos de modo que la fuente principal de obtención de carbono es la inversa en la indicada en el esquema general. Los metabolitos secundarios se forman por distintas vías, y como siguiendo su ruta biogenética una misma clase de compuestos, por ejemplo los alcaloides pueden tener varios orígenes.

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Esquema general de biosíntesis

CO2

+

fotosíntesis

pirimidas purinas

H3PO4

CARBOHIDRATOS

Hexosas

Pentosas

 ACIDOS NUCLEICOS NUCLEICOS

H2 O

glicósidos

POLISACARIDOS  Ac.cítrico

 Ac.piruv  Ac.piruvico (C 3)

 Aminoacido  Aminoacidos s alifáticos

PORFIRINAS  Ac. acético

 Ac. shikímicos (C6-C) -C)

CH 3CO2H

HO x3

HO

condensación (C 2)n

CO 2H

HO

 Ac. preféni prefénicos cos (C 6-C3-C) -C)

 Ac. mevaló mevalónico nico

OH

CO2H HO HO

HO

CH2CH2 CO2H

O

TERPENOS (C5n) Mono-

(c 10)

 AC. GRASOS GRASOS POLICETIDOS SATURADOS (COMP. FENOLICOS)

 Ac.  Ac. cinám ico

Sesqui- (C15) Di(C 20) Sester- (C25) Tri(C 30) Tetra- (C 40) (Carotenoides) ESTEROIDES  Azú  Azúcares cares SAPONINAS

Fenilalina (C6-C3)

 AC. GRASOS GRASOS INSATURADOS

 AROMAT  AROMATIC ICOS OS

POLIACETILENOS

LIGNANOS

PROSTAGLANDINAS

LIGNINAS

+

 Aminoáci dos aromáticos

+ +

FLAVONOIDES

 ALCALOI  ALCALOIDES DES

+ PROTEINAS

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Los productos naturales comprenden el estudio de: Plantas medicinales, colorantes, aceites esenciales, pesticidas ( biocidas naturales), floculantes etc, estos se pueden encontrar en plantas, microorganismos acuáticos y terrestres, hongos, bacterias, animales, y plantas acuáticas.

Las plantas medicinales  tiene una importancia de hace siglos, ya que fueron los únicos medicamentos con que contaron los seres humanos para el tratamiento de sus enfermedades. En la actualidad a pesar del desarrollo de la química química farmacéutica sintética y de la fermentación microbiana microbiana las  plantas siguen teniendo una posición destacada, el 52% de los productos naturales están implicados en en el desarrollo desarrollo de nuevos fármacos. fármacos. Otro aspecto importante es el cultivo “in vitro” de tejidos o células

vegetales, lo que ha permitido en ocasiones obtener un compuesto activo difícil de conseguir en las cantidades necesarias directamente. De las casi 400,000 especies vegetales del planeta se han investigado fitoquímicamente un pequeño porcentaje y la cantidad sometida a investigación biológica biológica ó farmacológica farmacológica es incluso más pequeña. thnobotany any FARMACOS OBTENIDOS DE PLANTAS ( Chadwick, D.J. and Marsh (Editores), E thnobot

and the Sear Sear ch for N ew Dr ugs discover discover y. , 1994)

Fármaco

Uso médico

 Ajmalina  Aspirina  Atropina Benzoina Cafeína  Alcanfor Cascara Cocaína Codeína Colchicina Demecolcina Deserpidina Dicumarol Digoxina Digitoxina Emetina Efedrina Eugenol Gallotanino Hiosciamina Ipecacuana Ipratropium Morfina Norcapina Papaina Papaverina

Arritmia cardiaca Analgésico, antiinflamatorio Dilatador de Pupila Desinfectante oral Estimulante Dolor reumático Purgativo Anestésico oftalmológico Analgésico, antitusivo Antigotosa Leucemia, linfoma Antihipertensivo Antitrombótico Fibrilación atrial Fibrilación atrial Disentería amebítica Broncodilatador Dolor dental Supositorios hemorroidales Anticolinérgica Emética Broncodilatador Analgésico Antitusivo Atenuador mucoso Antiespasmódico

Especie Vegetal Rauwolfia spp. Filipendula ulmaria  Atropa belladonna Styrax tonkinensis Camellia sinensis Cinnamomum camphora Rhamnus purshiana Erythoxylum coca Papaver somniferum colchicium autumnale Colchicium autumnale Rauwolfia canescens Melilotus officinalis Digitalis purpurea Digitalis purpurea Psychotria ipecacuanha Ephedra sinica Syzygium aromaticum Hamamelis virginia Hyoscyamus niger Psychotria ipecacuanha Hyosciamus niger Papaver somniferum Papaver somniferum Carica papaya Papaver somniferum

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Protoveratrina Pseudoefedrina Psoraleno Quinina Quinidina Rescinnamina Reserpina Senosido A,B Escopolamina Estigmasterol Estrofantina Tubocurarina Teniposido Tetrahidrocannabinol Teofillina Toxiferina Vinblastina Vincristina

Antihipertensivo Rinitis Vitiligo Profilaxis de la malaria Arritmia cardiaca Antihipertensivo Antihipertensivo Laxante Enfermedad locomotora Precursor esteroidal Fallo cardiaco congestivo Relajante muscular Neoplasma de vesícula Antimimético Diurético, antiasmático Relajante quirúrgico Enfermedad de Hodgkins Leucemia pediátrica

Veratrum album Ephedra sinica Psoralea corylifolia Cinchona pubescens Cinchona pubescens Rauwolfia serpentia Rauwolfia serpentia Cassia angustifolia Datura stramonium Physostigma venenosum Strophanthus gratus Chondrodendron tomentosum Podophylum peltatum Cannabis sativa Camellia sinensis Strychnos guianensis Catharanthus roseus Catharanthus rose

Los alcaloides constituyen un grupo de productos naturales muy importantes, en la química, la industria y la medicina. Las familias de plantas

más

importantes

que

contienen

alcaloides

son:

Amarillidaceae, Annonaceae, Apocinaceae, Asteraceae, Berberidaceae, Boraginaceae, Buxaceae, Celastraceae, Fabaceae, Lauraceae, Liliaceae, Loganiaceae, Menispermaceae, Papaveraceae, Piperaceae, Poaceae, Ranunculaceae, Rubiaceae, Rutaceae y Solanaceae. (CORDELL, G. A. ET.AL. 2001 En esta última categoría, se utilizan como potenciador analgésico y anestésico local (cocaína I), anticolinérgicos (atropina II y hyosciamina III), antihipertensivos (reserpina I V, rescinamina V, deserpidina VI), antimaláricos (quinina VII), antitumorales (vinblastina VIII, vincristina IX), antitusivo (codeína X), depresor cardíaco (quinidina XII), estimulante central (cafeína XIII), diuréticos (teobromina XIV y teofillina XV), emético (emetina XVI), analgésicos narcóticos (codeína X y morfina XI), supresor de gota (colchicina XVII), colinérgicos oftálmicos (pilocarpina XVIII y fisostigmina XIX) y tranquilizantes (reserpina IV y deserpidina VI).

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C CH3

CH3

CH2 H

CH2 H C

CH3

C

C

C

CH3

H

C

H

CH 3

CH3,

H

C

CH 3 CH 3

H

H

CH 3

H

CH3

C

CH = C

CH 3

H H3 C

CH 3 CH 3

R

C

`

 H,

CH3

C

CH 3 CH 3

H

`

H H3 C

H H H CH3 H

H H

`

`

H

H H

CH3 CH3 H3C  CH3 CH

H

CH3

H 3C

`

H 3C HC

CH3

CH 3

H 3C CH3

CH 3 `

H, CH3,

CH3

CH3 CH3 H `

`

H3C

H3 C

H 3CH

H

CH 3

C

H H H

CH3

H CH3

CH3

CH3

PAUTAS PARA EL ESTUDIO FITOQUÌMICO DE LA PLANTA AL PRINCIPIO ACTIVO

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Síntesis

Dilucidación de la estructura Extracción Plantas medicinales

Separación

Extracto(s)

Bioensayos

Fracción

Bioensayos

Compuesto(s) puro(s)

Toxicología

Modificación de la estructura

Bioensayo

El camino que conduce desde la planta intacta hasta sus constituyentes  puros, es largo, implica trabajo que bien podría tardar semanas o años, e incluye los siguientes pasos: Identificación correcta de la planta con la ayuda de especialistas (botánicos). Recolección y secado del material vegetal; se deben tomar  precauciones para evitar formación formación de artefactos. Preparación de extractos con diferentes disolventes; análisis de estos extractos por diferentes métodos cromatográficos. Fraccionamiento de los extractos por diferentes técnicas  preparatorias (cromatografía de columna, cromatografía de  partición, etc). Control de pureza de los productos aislados. Dilucidación de estructuras de los constituyentes por combinación de diversas técnicas espectroscópicas (UV/VIS, espectrofotometría IR, resonancia magnética nuclear de 1H y 13C, espectrometría de masas, difracción de rayos X) y técnicas químicas (hidrólisis, formación de derivados, reacciones de degradación etc). Síntesis o semisíntesis del producto natural. Modificación de la estructura, con miras a establecer las relaciones 







 

 

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farmacológico, esta selección resulta difícil. Los factores que se deben considerar son los siguientes: Criterio quimiotaxonómico Información proveniente de la medicina tradicional. Observaciones de campo. Recolección aleatoria.    

Quimiotaxonomía: Es la ciencia que clasifica a las plantas en función a la composición química química . La composición química química a menudo son específicos de una familia, género, especie. Si un producto natural tiene propiedades terapéuticas interesantes, puede ser posible encontrar encontrar sustancias análogas en las especies del mismo género, la misma familia. Por ej: La familia de las Gentianacea, que consta aproximadamente de 1100 especies se caracterizan por la presencia en las raíces y en las hojas de principios amargos que estimulan la digestión y de Xantonas con propiedades antidepresivas. Información proveniente de la medicina tradicional La selección de plantas con base en los datos de la medicina tradicional (etnofarmacología) puede llevar también al descubrimiento de nuevas moléculas promisorias. Las plantas de las regiones tropicales y sub tropicales son abundantes abundantes y han sido poco estudiadas estudiadas por lo tanto tanto representan un reservorio de moléculas nuevas con actividades terapéuticas potenciales, por lo lo tanto la información de los médicos tradicionales es muy importante importante para este tipo de investigación investigación Observaciones de campo Durante las expediciones de recolección son muy importantes las observaciones de campo, una especie que crezca en una ambiente hostíl, en el cual existe peligro de ataques de mosquitos, insectos, hongos  bacterias ó virus intentará protegerse con la síntesis de constituyentes insecticidas, fungicidas, antibacterianos ó virucidas.

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Recolección aleatoria La recolección aleatoria aleatoria también es indispensable dado el potencial de las  plantas que no han sido investigadas aún y la batalla necesaria para derrotar enfermedades. Por lo tanto se deben tomar muchos caminos diferentes para llegar al descubrimiento de agentes terapéuticos novedosos, en especial con enfermedades como el SIDA esclerosis múltiple, enfermedad de Parkinson, Alzeihmer y ciertos tipos de cáncer.  b)

Interés dirigido a un tipo de compuesto químico Por ejemplo se quiere estudiar especies que sintetizan Quinonas, se ubica la especie, se realiza la revisión bibliográfica, se realiza las  pruebas de laboratorio (screening fitoquímico) de las diferentes  partes de la planta y también es necesario tener en cuenta las edades. edad es. Se procede a la extracción, fraccionamiento, purificación y pruebas de actividad biológica.

c)

Interés por un determinado tipo de actividad biológica. Se realiza la revisión bibliográfica para identificar la familia, género y especie que tengan esta actividad, se preparan los extractos, se realizan los ensayos de actividad biológica al extracto activo, se realiza el fraccionamiento cromatográfico bioguiado con la finalidad de aislar e identificar los compuestos y comprobar su actividad. Para el cribado de actividades biológicas los extractos vegetales y de otros organismos es de vital importancia contar con bioensayos apropiados Estos bioensayos pueden involucrar diferentes formulas - Organismos inferiores Microorganismos , insectos crustáceos, moluscos

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MARCHA FITOQUIMICA PRELIMINAR (SCREENING FITOQUÍMICO) EXTRACTO HEXÁNICO Determinación cualitativa de Flavonoides Disolver el residuo desgrasado obtenido de la filtración de la maceración para obtener el extracto hexánico 2 g. en 10 mL. de etanol y filtrar. Colocar de 1-2 mL. del filtrado en tres tubos de ensayo. El tubo Nº 1 sirve de control. Ensayo de cianidina - Al tubo Nº 2 añadir 0.5 mL de HCl concentrado y una tirita de magnesio. Observar la formación formación de color (de (de verde a rojo) rojo) al cabo de 10 minutos. - De haber cambio de color con respecto al tubo de control, enfriar y diluir con volúmenes iguales de agua y añada 1 mL. de alcohol amílico, agite y espere que se separe. - El desarrollo de tonalidades rojizas en la capa del alcohol amílico es indicativo de flavonoides. Ensayo de leucoantocinina - Al tubo Nº 3 añadir 0.5 mL de HCl concentrado y calentar en baño de maría por 5 minutos - El desarrollo de un color rojo-violeta es indicativo de la presencia de leucoantocianinas. - En caso de no aparecer inmediatamente el color, deje reposar a temperatura ambiente por una hora antes de anotarlo como negativo. La formación de color se da en e n forma lenta. Ensayo para alcaloides

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Ensayo para triterpenos y esteroides A una fracción del extracto hexánico, se disuelve en 4 mL. de cloroformo, filtrar y dividir en tres tubo. El tubo Nº 1 es el control. Al tubo Nº 2 se realiza la Reacción de Liebermann-Burchard. A un 1 mL. de muestra se añade igual volumen de anhídrido acético. Por la  pared del tubo de ensayo se dejan caer de 3-4 3 -4 gotas de ácido sulfúrico concentrado. La aparición de una coloración verde-azul indica la presencia de estructuras esteroidales y una coloración rojo-pardo indica la  presencia de estructuras estructuras triterpénicas. Al tubo Nº Nº 3 añadir 3-4 gotas de ácido sulfúrico concentrado dejándolo caer por las paredes del tubo hasta el fondo. La formación de un anillo de color rojo en la interfase es indicativa de esteroles insaturados. Ensayo para para derivados derivados Antracénicos (Quinonas) A una fracción del extracto hexánico, se disuelve en 3 mL. de cloroformo. Posteriormente se filtra y se distribuye en 3 tubos de ensayo, el tubo Nº 1 para control, al tubo Nº 2 se agita con 1 mL de hidróxido de sodio al 5 % en agua. Coloración rosa- rojo en la fase acuosa, indica presencia de quinonas . En el tubo Nº 3, adicionar 1 mL. de solución de acetato de magnesio al 0.5 % en metanol. Coloración roja indica presencia de antraquinonas libres. Ensayo para Lactonas y Cumarinas (Baljet) A una fracción de extracto hexánico, se disuelve en 2 mL. de etanol se distribuye en dos tubos de ensayo un tubo para control, al otro tubo se le añade una mezcla recién preparada de de 1 mL de ácido pícrico al 1 % en etanol y 1 mL de hidróxido de sodio al 10 % en agua. Un color o precipitado rojo-naranja indica la presencia de agrupamientos lactónicos (cumarinas).

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La aparición de una coloración verde azulada indica la presencia de carotenos.

EXTRACTO DICLOROMETANO Y METANOLICO Ensayo para Alcaloides Pesamos 400 mg. de extracto seco se le adiciona 15 ml de ácido clorhídrico al 10 % se calienta hasta disolver y filtramos. De esta forma se obtiene un residuo y una disolución ácida (lavados ácidos). Se mide 1 mL de los lavados ácidos en cuatro (4) tubos de ensayo un tubo es para muestra patrón y adicionamos unas gotas de los reactivos de reconocimiento de Dragendroff (la presencia de turbidez, floculación o precipitado rojo- naranja), de Mayer (precipitado crema), de Wagner (precipitado marrón).Pruebas directas para alcaloides. Al lavado ácido sobrante lo colocamos en un pera de separación y extraemos con cloroformo, donde se obtiene dos fases: clorofórmica clorofórmica y acuosa. La fase clorofórmica lo pasamos a un balón y lo llevamos a sequedad en un rotavapor rotavapor , hacemos una CCF, la presencia presencia de manchas de color naranja indica la presencia p resencia de alcaloides . Ensayo para Triterpenos y Esteroides (Reacción (Reacción de Liebermann Liebermann Burchard)  – Burchard)

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Ensayo para Quinonas (Borntrager) Tomar un tubo de ensayo con la muestra ya disuelta en. Cloroformo (CHCl3), se adiciona 1 mL. mL. de (NaOH) hidróxido hidróxido de sodio sodio al 5 %, agitamos y dejamos dejamos en reposo, se forman forman dos fases la clorofórmica y alcalina . Una coloración, coloración, rojo, rosa en la fase alcalina alcalina indica la  presencia de quinonas. De la disolución clorofórmica obtenida a partir de la fracción para el ensayo de triterpenos triterpenos y esteroides. esteroides. Tubo Nº2 Nº2 se utiliza utiliza 1 mL. la cual se le adiciona la misma cantidad de hidróxido de sodio al 5 % Una coloración, rojo, rosa en la fase alcalina indica la presencia presencia de quinonas. En el tubo Nº 3 adicionar 1 mL. de solución de acetato de magnesio al 0.5 % en metanol. Coloración roja indica presencia de antraquinonas libres.

Ensayo para Flavonoides (Método de Shinoda) Colocar en un tubo de ensayo con la muestra ya diluida en etanol, adicionar un trocito de cinta de magnesio magnesio y 5 a 6 gotas de HCl HCl concentrado. Observándose la reacción del Mg con el HCl donde se realiza un cambio de color en la parte superior del líquido de nuestra dando:

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Calentar la mezcla a baño María durante 10 min. Filtrar. Agitar el el filtrado con 10 mL. de cloroformo cloroformo en tres tubos de ensayo. Al tubo Nº 1 se agrega el reactivo de Baljet. (Coloración roja, naranjarojiza o violeta son cardenólidos) Al tubo Nº 2 realizar la reacción de Keller-Kiliani Keller-Kiliani (ácido acético glacial, 1 gota de cloruro férrico al 5 % en metanol y ácido sulfúrico concentrado) Coloraciones intensas. Al tubo Nº 3 se realiza la reacción de Salkowaki (núcleo esferoidal). Coloración amarilla-rojo sangre.

Ensayos para Lactonas y Cumarinas (Baljet) A una fracción de extracto se disuelve en 2 mL. de etanol se distribuye en dos tubos de ensayo un tubo para control, al otro tubo se le añade una mezcla recién preparada recién preparada de de 1 mL. de ácido pícrico al 1 % en etanol y 1 mL de hidróxido de sodio al 10 % en agua. Un color o precipitado rojo-naranja indica la presencia de agrupamientos lactónico (cumarinas). Tomar dos tubos de ensayo de la muestra muestra ya disuelta en etanol. Para el ensayo de  Cumarinas volátiles; En un papel filtro sembrar unas gotitas de KOH , envolver en el tubo donde está la muestra amarrarlo y llevar a baño María por 5 minutos y sacar el papel filtro, llevar al UV el anillo de color amarillo verdoso fluorescente nos

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A una fracción del extracto diluida en etanol se le adiciona 4 mL de agua y se agita la mezcla fuertemente durante 2 minutos, dejar reposar 5 minutos. Si aparece una espuma jabonosa de más de 2 mm de altura en la superficie del líquido y persiste esto indica la presencia de saponinas.

Ensayo para aminoácidos y aminas (Ninhidrina) A una fracción el extracto diluido en etanol se le adiciona 1 mL de disolución de ninhidrina al 5 % en etanol. Se calienta en baño de agua de 5 –  10  10 minutos. La aparición de una coloración azul violácea indica la presencia de aminas. MATERIAL FRESCO Determinación de glicósidos cianogénicos (glicocianos) Es la única prueba que se realiza, sin someter a extracción con solvente el material utilizando material fresco, debido a la inestabilidad de estos compuestos, para esto se hace lo siguiente: Una cierta cantidad (aproximadamente 10 g.) de material fresco se extrae con ácido diluido (H 2SO4, HCl) en un matraz con tapa esmerilada, del cual se cuelga una tira de papel picrato previamente  preparada, todo el conjunto se coloca a la estufa a 60º C,

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ENSAYO O PRUEBA Alcaloides

EXTRACTOS Hx CH2Cl2 

MeOH

D W M

Triterpenos y Esteroides Quinonas Flavonoides Glicósidos Cardiotónicos Lactosas y Cumarinas Fenoles y Taninos Saponinas Aminoácidos y Aminas Lípidos y/o Aceites Esenciales Carotenos Leyenda: Ensayo positivo (+), contenido: (+) Poco; (++) Medio; (+++) Abundante Ensayo negativo (-)

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CAPITULO II: METODOLOGÌA DEL ANALISIS FITOQUIMICO El análisis fitoquímico comprende 04 etapas bien definidas. a) Recolección y clasificación botánica de la especie en estudio  b) Extracción, separación, purificación de los constituyentes químicos c) Determinación estructural d) Ensayos biológicos y farmacológicos A) Recolección de la especie en estudio. Debe hacerlo un botánico, las plantas herbáceas son generalmente utilizadas en su totalidad. Plantas leñosas, se seleccionan las partes a estudiar (hojas, corteza, raíz, frutos, flores, semillas, madera.

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3.  Destilación por arrastre de vapor, utilizado principalmente

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TECNICAS CROMATOGRAFICAS PARA LA SEPARACION DE COMPUESTOS A. CROMATOGRAFIA CROMATOGRAFIA DE ADSORCION Consiste en pasar la muestra sobre un adsorbente sólido (fase estacionaria) y un eluyente líquido (fase móvil) para el caso de cromatografía líquida; o un adsorbente sólido y un eluyente gaseoso  para el caso de cromatografía cromatografía de gases. ADSORBENTES Deben tener alta capacidad de adsorción, ser insolubles en el eluyente, e inertes a las sustancias a ser separadas por cromatografía La estructura porosa y la granulación dependerán si se usa columna gravitacional o HPLC. Los adsorbentes más usados son:

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 partición), tiene la ventaja y la rapidez del desarrollo, y la versatilidad de las operaciones que se pueden hacer sobre sobre el sustrato: sustrato: se abrevia abrevia TLC. La CCF se puede preparar en los laboratorios ó comprarse en las casas comerciales llamados cromatofolios de 20cmx 20 cm, que se cortan de acuerdo a las necesidades, en este caso el soporte puede ser de aluminio,  plástico y el adsorbente de 1mm de espesor muy uniforme. Una de las variantes de la cromatografía de capa fina es la cromatografía preparativa donde el soporte es de vidrio de 1 mm. de espesor.

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GROMATOGRAFIA DE COLUMNA (CC) Es la más usada en la separación de productos naturales con tal finalidad se emplean adsorbentes ya mencionados en la cromatografía de capa fina: gel de sílice, alúmina celulosa, florisil, poliamida, sephadex, , intercambiadores de iones, y resinas de intercambio iónico. Actualmente se utilizan otros adsorbentes que permiten trabajar en fase

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COLUMNA HUMEDA.- Tiene 02 variantes: a).-Se coloca el solvente  previamente seleccionado y luego se deja caer lentamente el adsorbente, se golpea para ayudar la compactación sea uniforme. B).- La segunda se  prepara una suspensión uniforme del de l adsorbente de la fase móvil y se deja caer sobre una capa de la fase móvil contenida en el tubo de vidrio. Esta tiene la ventaja de una composición más uniforme y el inchamiento del adsorbente ocurre antes de poner en la columna y evita las obstrucciones. La muestra se introduce en solución concentrada, preferentemente disuelta en el mismo solvente sobre la superficie del adsorbente, también la muestra

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Los

métodos

espectroscópicos

especialmente

RMN;

IR,

UV-

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estados vibracionales y rotacionales que acompañan a las transiciones

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