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DITERPENOS Tetraciclicos

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DITERPENOS Tetraciclicos Romero Castillo Marianella Dolores Análisis de los ácidos kaurénicos de varias especies de coespeletia y ruilopezia Universidad de Los Andes-Facultad de Farmacia y Bioanálisis-Postgrado en Química de Medicamentos. 2000. p. 106 Venezuela Disponible en: http://bdigital.ula.ve/RediCiencia/busquedas/DocumentoRedi.jsp?file=33592&type=ArchivoDocumento &view=pdf&docu=26870&col=5 ¿Cómo citar? UNIVERSIDAD DE LOS ANDES FACULTAD, DE FARMACIA POSTGRADO EN, QUIMICA DE MEDICAMENTOS MERIDA-VENEZUELA .·' . '·.·~·f!&·= ·.·.·····.·~=:e·:··.~· ··.~·Y:~.· : ; .... : .... sERJIULA \ e rdero1 \ 'l'uliO Febres -~·--· ' Por: Farm o Marianella Do Romero Castillo Septiembre, 2000 DIGITAliZADO http://tesis. u/a. ve ESTA TESIS FUE REALIZADA EN EL LABORATORIO DE PRODUCTOS NATURALES DEL INSTITUTO DE INVESTIGACIONES DE LA FACULTAD DE FARMACIA. UNIVERSIDAD DE LOS ANDES. TUTORIADA POR EL DOCTOR ALFREDO USUBILLAGA. AGRADEaMIENTOS A la DIVINA PRESENCIA DE DIOS, por ser mi fuente creadora y brindarme su amor divino y por haberme enviado a sus guías espirituales y guardianes silenciosos quienes me guían y me acompañan y me permiten compartir con mis hermanos de grupo, a todos ellos gracias. A mi querida familia por su apoyo en todo momento. Al Doctor ALFREDO USUBILLAGA, por su apoyo y valiosa colaboración en el aporte de sus conocimientos y sus generosos consejos y amistad. Agradezco al CONICIT, por el otorgamiento al profesor ALFREDO USUBILLAGA, el proyecto SI-97000048 que permitió la compra del equipo GC/MS modelo HP 5973 con el cual se realizó el trabajo. A mis queridas compañeras de post grado, ROSA, YOLIMAR, REBECA Y DAYSIS, por brindarme su amistad sincera. A la profesora NANCY KHOURY, por su cotutoria. Al profesor LUIS ROJAS, por su colaboración. Al Instituto de Investigaciones de la Facultad de Farmacia. Universidad de los Andes. RESUMEN El presente trabajo describe el aislamiento e identificación de los ácidos kaurénicos que contienen las hojas de Coespeletia moritziana, Coespeletia spicata, Coespeletia thyrsiformis, Ruilopezia atropurpurea, Ruilopezia lindenii Ruilopezia marcesens, plantas endémicas de los Estados Mérida y Táchira, conocidos popularmente como frailejones. Las hojas secas y molidas de cada una de estas plantas se extrajeron con una mezcla de n-hexano-éter dietílico (3:1), se aisló la fracción ácida mediante agitación del extracto etéreo con una solución de NaOH 0.1 N. Una alícuota de la fracción ácida se metiló con diazometano y los ésteres metílicos se inyectaron en un cromatógrafo de gases provisto de un detector de masas (HP MSD 5973). Se utilizó una columna capilar de 5% de fenil-metil-polisiloxano (HP-5) de 30m de largo, 0.2 mm de diámetro interno y 0.25 ¡.tm de espesor de película. Los ésteres metílicos de los ácidos se identificaron mediante comparación de sus espectros de masas con los espectros de sustancias patrón existentes en el laboratorio, o preparadas mediante síntesis. En las tres especies de Coespeletia estudiadas el ácido kaurénico es el componente más abundante, sin embargo en las tres está presente el ácido (-)-kaur-9(11)-16-dien-19-oico. Otro ácido particularmente abundante es el ácido 15-a-senecioxi-(-)-kaur-16-en-19-oico (H) (10.8% en la C. thyrsiformis) y el ácido 15- a-isovaleroxi-(-)-kaur-16-en-19-oico (I) (20.2% en la C. spicata). Es importante anotar que en la C. moritziana recolectada en el páramo de Piñango en Septiembre contiene 28.7 'Yo H, en tanto que aquella cosechada en el páramo de la Culata en Diciembre contiene 30.1 % de I. En las cuatro especies de Ruilopezia estudiadas igualmente se encuentra el ácido kaurénico como componente mayoritario y también está presente el ácido (-)-kaur-9(11)-16-dien-19-oico. Sin embargo en la R. floccosa el ácido kaurénico (50.9%) no está tan contaminado por el ácido diénico (9.0'Yo) y por consiguiente, esta especie es particularmente valiosa como fuente natural de ácido kaurénico. La R. marcesens contiene ácido 15-a-senecioxi-(-)-kaur-16-en-19-oico (15.9%) y el ácido 15- a-isovaleroxi-(-)-kaur-16-en-19-oico es relativamente abundante en la R. atropurpurea (18.2%) y en la R. floccosa (25.2%), en cambio en la R. /indenii el ácido (-)-kaur-9(11)- 16-dien-19-oico es el segundo más abundante (28.6%). ABSTRACT This work describes the isolation and identification of kaurenic acids present in the leaves of Coespeletia moritziana, Coespeletia spicata, Coespeletia thyrsiformes, Ruilopezia atropurpurea, Ruilopezia floccosa, Ruilopezia lindenii and Ruilopezia marcesens, endemic plants of the páramos from Mérida and Táchira States, popularly known as frailejón. Dry and ground leaves were extracted with an n-hexano:diethyl ether mixture (3:1), the acid fraction was obtained by shaking the ethereal extract with a 0.1 N NaOH solution. An aliquot of the acid fraction was methylated with diazomethane and the methyl esters were inyected in a gas chomatograph fitted with a 5% phenyl-methyl polysiloxane capillary column (30 m x 0.2 mm id x 0.25 ¡..tm film) was used. The methyl esters were identified by genuine samples available in the laboratory or obtained by synthesis. Kaurenic acid was the main contituent in all species studied, but (-)-kaur-9(11).16-dien-19-oic acid was also present. Another substance particulraly abundant is 15-a.-senecioxi-(-)-kaur-16-en-19-oico (H) (10.8% in C. thyrsiformiS) and 15-a.-isovaleroxi-(-)-kaur-16-en-19-oico (I) (20.2% in C. spicata). It is worth noting that C. moritziana isolated at Piñango in Septiembre contains 28.7% of H while C. moritziana at La Culata in December contains 30.1% of I. The four species of Ruilopezia al so contain kaurenic a cid as the main contituent and (-)-kaur-9(11)-16-dien-19-oic acid is al so present in all of them. Nevertheless (-)­ kaur-9(11)-16-dien-19-oic acid is not no abundant (9.0%) in R. floccosa which contains 50.9% kaurenic acid, therefore this species is valuable as a source of kaurenic acid. R. marcesens contains 15-a.-senecioxi-(-)-kaur-16-en-19-oic acid (15.9%) and 15-a.­ isovaleroxi-(-)-kaur-16-en-19-oic acid is relativaly abundant in R. atropurpurea(18.2%) and R. floccosa (25.2%), on the other hand (-)-kaur 9(11)-16-dien-19-oic acid is the second most important component in R. lindenii(28.6%). CONTENIDO Pag I.- INTRODUCCIÓN . ......................... ...... ....... ................. ............................................ 1 IT.- ANTECEDENTES .................................................................................................... 9 CLASIFICACIÓN DE LOS DITERPENOS ...................................................... 10 - DITERPENOS LINEALES .................................................................................... 10 - DITERPENOS BidCLICOS ................................................................................ 10 - DITERPENOS TRidCLICOS .............................................................................. 11 - DITERPENOS TETRAdCLICOS ........................................................................ 12 - DITERPENOS MACROdCLICOS Y SUS DERIVADOS DE CICLIZACIÓN .................................................................................................. 13 BIOSINTESIS DE DITERPENOS ..................................................................... 16 DITERPENOS AISLADOS DE LAS HELIANTHEAE .................................... 19 m.- OBJETIVOS ............................................................................................................ 21 IV.- RESULTADOS......................................................................................................... 23 RECOLECCIÓN........................................................................................................ 24 EXTRACCIÓN Y ANÁLISIS................................................................................ 24 V.- PARTE EXPERIMENTAL ....................................................................................... 34 RECOLECCIÓN ........................................................................................................ 35 EXTRACCIÓN .......................................................................................................... 35 PREPARACIÓN DE LA NITROSO METIL UREA ............................................ 36 METILACIÓN DE LOS ÁCIDOS KAURÉNICOS ............................................ 36 OBTENCIÓN DEL ÁCIDO 15-0-VALEROXI-(-)- KA UR-16-EN-19-0ICO .......................................................................................... 3 7 OBTENCIÓN DEL ÁCIDO 15-0.ISOVALEROXI-(-)- KA UR-16-EN-19-0ICO .......................................................................................... 3 7 OBTENCIÓN DEL ÁCIDO 15-0.BUTIROXI-(-)- KAUR-16-EN-19-0ICO .......................................................................................... 38 ANÁLISIS CROMATOGRÁFICO DE GASES/MASAS................................. 39 , 13 , ANALISIS DE RMN C DE LOS DERIVADOS KAURENICOS .................. 40 ANÁLISIS DE ESPECTROS EN DOS DIMENSIONES............................... 40 VI.- DISCUSIÓN............................................................................................................ 41 VII.- CONCLUSIONES................................................................................................... 49 vm.- BIBLIOGRAFIA ...................................................................................................... 51 IX.- ANEXOS ................................................................................................................... 59 CONTENIDO DE TABLAS Pag TABLA l. ESTRUCTURA Y ORIGEN DE ALGUNOS KAURENOS ........................
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