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Zanthoxylum Rhoifolium LAM (Rutaceae) Et Bulnesia Arborea Cl

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Zanthoxylum Rhoifolium LAM (Rutaceae) Et Bulnesia Arborea Cl N° d‘ordre : 4273 THÈSE en Cotutelle PRÉSENTÉE A L’UNIVERSITÉ BORDEAUX 1 ÉCOLE DOCTORALE DES SCIENCES CHIMIQUES Par Laura Vanessa SANTIAGO BRUGNOLI POUR OBTENIR LE GRADE DE DOCTEUR SPÉCIALITÉ : CHIMIE ORGANIQUE ___________________________________________________________________________ Etude Phytochimique de Plantes Médicinales des Andes Vénézuéliennes : Zanthoxylum rhoifolium LAM (Rutaceae) et Bulnesia arborea Cl. Gay (Zygophyllaceae) ___________________________________________________________________________ Directeur de recherche : Dr. Laurent Pouységu Soutenue le : 22 juillet 2011 Après avis de : Mme RODRIGUEZ, María Professeur, Universidad Central de Venezuela Rapporteur M. CHARRIS, Jaime Professeur, Universidad Central de Venezuela Rapporteur Devant la commission d‘examen formée de : Mme RODRIGUEZ, María Professeur, Universidad Central de Venezuela Rapporteur M. CHARRIS, Jaime Professeur, Universidad Central de Venezuela Rapporteur M. ROJAS, Luis Professeur, Universidad de Los Andes Président du jury M. POUYSEGU, Laurent Maître de Conférences, Université Bordeaux 1 Directeur de thèse M. ROSQUETE, Carmelo Professeur, Universidad de Los Andes Co-directeur de thèse M. QUIDEAU, Stéphane Professeur, Université Bordeaux 1 Examinateur Mme ROJAS, Janne Professeur, Universidad de Los Andes Membre invité Université Bordeaux 1 Les Sciences et les Technologies au service de l’Homme et de l’environnement ii Universidad de Los Andes Facultad de Ciencias Postgrado Interdisciplinario en Química Aplicada Laboratorio de Productos Naturales Estudio Fitoquímico de Plantas de los Andes Venezolanos: Zanthoxylum rhoifolium LAM (Rutaceae) y Bulnesia arborea Cl. Gay (Zygophyllaceae). Tesis de grado para optar al grado académico de Doctora en Química Aplicada Lcda. Laura Vanessa Santiago Brugnoli Tutor: Dr. Carmelo Rosquete Porcar Co-Tutor: Laurent Pouységu Mérida-Venezuela Julio, 2011 iii iv v vi vii A la memoria de mi amadísima nonna Bruna de Brugnoli viii ix AGRADECIMIENTOS -A Dios, la Santísima Virgen y al Santo Niño sobre todas las cosas. -A mi madre Rossela, mamita linda…….gracias por tu apoyo siempre, por levantarme el ánimo cuando estaba a punto de dejarlo todo, tus oraciones, por saber siempre que lo lograría ¡Te amo mami! -A mi padre, Iván, gracias papito bello…….por siempre confiar en mí, apoyándome en todas mis decisiones…..siempre tomando mi mano en todo lo que hago y deshago, por saber esperar ¡Te amo papi! -A mi hermano, Iván Ricardo, gracias por trasnocharte conmigo……..acompañándome en el momento justo, como siempre, desde niños, sin ti y sin tu apoyo nunca hubiese terminado. ¡Te amo sshoo! -A mi esposo, mi amor Carlos, gracias por tu paciencia, tu compañía, tú ayuda, tu apoyo incondicional, eternamente a mi lado, gracias por escogerme. ¡Te amo gordo! -Al Dr. Carmelo Rosquete, gracias por todos estos años que trabajamos juntos, por compartir sus conocimientos, por formarme profesionalmente, por brindarme su amistad y confianza, por darme la oportudidad de trabajar en este hermoso proyecto, mi agradecimiento por siempre. ¡Lo voy a extrañar un montón! -A todos los profes del Grupo del Laboratorio de Productos Naturales: Paulino Delgado, Andrés Abad, Sonia Koteich y Juan Manuel Amaro, gracias por todos estos años que pasé junto a ustedes que hicieron de mi vida una época muy especial y al Técnico Ciro Rodríguez gracias por toda tu ayuda negrito. -A los panitas del Laboratorio de Productos Naturales: Pablo, José Adolfo, Nydian, Gabriela, Carolina, Elier, Roger y Dario compañeros de rumbas, tragos, de trabajo….¡en fin! apoyándonos unos a otros y dándonos ánimos cuando ya no aguantamos más…..lo resolvemos solo con “dos”. -Al Dr. Luis B. Rojas, gracias por todo el apoyo, ayuda, la confianza que tuvo en mí para la realización de este trabajo, por su bella amistad, por permitirme conocer otras culturas y abrir mi mente a cosas nuevas, lo disfruté mucho, desde el principio hasta el final…….eternamente agradecida. -Al Dr. Ali Bahasas, profe…….gracias por su apoyo incondicional, por sus excelentes consejos, por dedicarme horas de su ocupada vida para ayudarme y escucharme…….mi agradecimiento por siempre. -Al Dr. Laurent Pouységu, no tengo palabras para agradecerle todo lo que hizo para hacer realidad este proyecto, hoy culminado. Fue un gran placer para mí trabajar con usted en esta experiencia Francovenezolana, fue una de las mejores etapas de mi vida. ¡Mil gracias! x -Au Dr. Sthephane Quideau, le remercie pour la confiance et pour me permettre travailler dans son groupe de recherche, ça a été une expérience inoubliable á Bordeaux, avec tout mon coeur, merci beaucoup. -Au mes collègues du groupe Quideau: Mélanie M., Céline, Marion, Delphine, Gildas, Tahiri, Mélanie D., Tony, Gaëlle, Stefan Chassaing et Rémi, toujours la mémoire…….merci à touts! -Al profe Dr. Jaime Charris, que fue mi compañero y amigo de laboratorio en el IECB y jurado evaluador de este trabajo, muchas gracias profe por todo y por los buenos momentos en Bordeaux. -A los chicos del IECB, que siempre llevo en mi corazón Vania, Marisa, Anna y Pierre que hicieron de mi estancia en Bordeaux divertida y me hicieron sentir como en casa. ¡Muchas gracias amigos! - Mon plus profond remerciement à Dra. Marie Allet Lacaille-Dubois, pour m’avoir accueillie au sein de son equipe pendant six mois dans son laboratoire, pour votre générosité, merci pour m'enseigner des choses nouvelles, vraiment merci beaucoup. -Au tout le equipe du Laboratoire de Pharmacognosie, UMIB : Clemence, Aymen, Deb, Jens, Gaoussou, Guy, Stéphanie et Nathalie, merci pour faire lâches houres de travaille amusantes à Dijon, ils me manquent. -A mis amigas de siempre: Eleida, Wendy, Iraida, Caro y Maricarmen, que fueron, son y serán de gran apoyo para mi en esta dura etapa ya culminada, estando lejos y cerca, gracias “jamigas” por estár siempre ahí. ¡Las adoro! -Al Programa Cooperativo Postgraduado (PCP) Francia-Venezuela, FONACIT- 46.255 por el financiamiento otorgado para este proyecto. -Al FONACIT, en el marco de la Misión Ciencia, por los finaciamientos otorgados a través del contrato Nº 200601418. - Y a todas las personas que de una u otra forma colaboraron en la realización de este proyecto ¡muchas gracias! Vane. xi xii Résumé Ces travaux de thèse concernent l‘étude phytochimique de deux plantes médicinales et plus particulièrement deux espèces que l‘on trouve dans la zone des Andes Vénézuéliennes : Zanthoxylum rhoifolium LAM (Rutaceae) et Bulnesia arborea Cl. Gay (Zygophyllaceae). L‘intérêt d‘étudier ces espèces a été guidé par la grande diversité de composés isolés antérieurement et par les activités pharmacologiques précédemment décrites, aussi bien pour le genre Zanthoxylum que pour la famille Zygophyllaceae. a) Zanthoxylum rhoifolium LAM (Rutaceae) Avec près de 250 espèces distribuées dans les régions chaudes et tropicales du monde, principalement en Afrique, en Amérique du Nord et du Sud, en Asie et en Australie, Zanthoxylum est le genre le plus abondant dans la famille des Rutaceae. Au Venezuela, 22 espèces de Zanthoxylum ont été répertoriées et elles sont largement distribuées dans tout le pays. Le genre Zanthoxylum est très connu dans la médecine populaire pour ses propriétés curatives; certaines de ses espèces sont surtout utilisées par les populations autochtones, qui vivent dans des zones où ces plantes abondent, pour soulager et calmer, entre autres choses, les rages de dents, la toux, la diarrhée, les douleurs liées à l‘audition, les vomissements et les douleurs d‘estomac dues à des vers intestinaux. Il a également été démontré que certaines espèces possèdent des propriétés pharmacologiques d‘intérêt parmi lesquelles figurent des activités antitumorales, antileucémiques, antimicrobiennes (de Moura et al., 1997 ; Nissanka et al., 2001), antibactériennes (Abreu et al., 2003a,b), anti-HIV (Cheng et al., 2005), antipaludiques (Jullian et al., 2006 ; Kirira et al., 2006), antifongiques (Bafi-Yeboa et al., 2005), amœbicides, anti-giardiases (Arrieta et al., 2001), trypanocides (Ferreira et al., 2007), anti-leishmaniennes (Ahua et al., 2007) ou encore une utilisation comme répulsif anti-moustique (Das et al., 2003). Les extraits de ces plantes du genre Zanthoxylum sont utilisés commercialement comme colorants pour les tissus (Cuca et al., 1998) et comme épices piquantes dans certaines recettes de cuisine (Xiong et al., 1995). Du point de vue de la phytochimie, le genre Zanthoxylum a été largement étudié depuis le début du XXème siècle ; plusieurs espèces ont ainsi été explorées en raison de la grande variété de squelettes structuraux présents dans la famille Rutaceae et de la diversité des xiii métabolites secondaires (alcaloïdes, amides, lignanes, flavonoïdes, terpènes…) biosynthétisés par ces espèces végétales. Notre étude phytochimique a été réalisée sur les feuilles fraîches de Zanthoxylum rhoifolium LAM (Rutaceae) que nous avons soumises à des extractions successives, réalisées à chaud à l‘aide d‘un appareil Soxhlet (Natori et al., 1981), avec des solvants de polarité croissante (hexane, acétone et méthanol) jusqu‘à ―épuisement‖ du matériel végétal (Natori et al., 1981). L‘extrait acétonique (52,30 g), préalablement absorbé sur gel de silice, a ensuite été soumis à un processus de fractionnement et de séparation en utilisant plusieurs techniques chromatographiques sur gel de silice, sur support Sephadex® LH-20 et sur couche préparative (Coll & Bowden, 1986 ; Henke, 1995 ; Mikes, 1979 ; Natori et al., 1981; Simpson, 1976 ; Sjövall et al., 1968 ; Snyder & Kirkland, 1974 ; Stahl, 1969). Cette étude
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