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Investigation Phytochimique D'une Brosse À Dents Africaine

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Investigation Phytochimique D'une Brosse À Dents Africaine FACULTE DES SCIENCES Institut de Pharmacognosie et Phytochimie Investigation phytochimique d’une brosse à dents africaine Zanthoxylum zanthoxyloides (Lam.) Zepernick et Timler (Syn. Fagara zanthoxyloides L.) (Rutaceae) Thèse de doctorat présentée à la Faculté des Sciences de l’Université de Lausanne par Fatima CHAAIB KOURI Pharmacienne diplômée de l’Université de Genève Jury Prof. Jean Hernandez, Président Prof. Kurt Hostettmann, Directeur de thèse Prof. Anne-Marie Mariotte, Expert Dr. Emerson Ferreira Queiroz, Expert Dr. Andrew Marston, Expert LAUSANNE 2004 A la mémoire de mon père A ma mère et à son courage A mon mari A tous les membres de ma famille Remerciements Je tiens particulièrement à remercier mon directeur de thèse, Monsieur le Professeur Kurt Hostettmann, pour m’avoir accueilli au sein de son institut et permis de réaliser cette thèse. Son dynamisme pour la recherche des produits naturels a été pour moi une source de motivation. Je tiens également à le remercier pour m’avoir permis de présenter quelques uns de mes résultats lors de congrès internationaux et de m’avoir fait confiance dans les diverses tâches qui m’étaient attribuées en tant qu’assistante d’enseignement. Mes remerciements vont également à Monsieur le Professeur Jean Hernandez, de l’Université de Lausanne, d’avoir accepté de présider la séance de mon examen privé et ma soutenance publique. J’aimerais également remercier Madame le Professeur Anne-Marie Mariotte, de l’Université de Grenoble et Messieurs les Docteurs Emerson Ferreira Queiroz et Andrew Marston, tous deux de l’Université de Lausanne pour avoir accepté de faire partie de mon jury de thèse. J’ai apprécié notre interaction lors de mon examen de thèse et lors de ma soutenance publique. Je tiens particulièrement à exprimer ma gratitude à Messieurs les Docteurs Emerson Ferreira Queiroz et Andrew Marston pour leur disponibilité et leurs conseils tout le long de mon travail de thèse. Un grand merci au Professeur Jean-Luc Wolfender pour ses nombreux conseils dans le domaine de l’analytique malgré un emploi de temps surchargé. J’aimerais encore remercier Monsieur le Docteur Drissa Diallo, de l’Ecole Nationale de Médecine et de Pharmacie du Mali, pour ses précieux conseils au début de ma thèse. Je tiens à remercier le Docteur Kurt Schenk, de l’Institut de Cristallographie de l’Université de Lausanne, pour son analyse cristallographique. Je souhaite encore remercier le Professeur Celso Vataru Nakamura, de la Fundação Universidade Estadual de Maringã, Brasil pour le test sur Streptococcus mutans. Un merci collectif à tous les membres de l’IPP, en particulier Aly, Lalao, Patrice, Milena, Boris et Max. Finalement, toute ma gratitude va à mes parents qui n’ont jamais douté de moi et qui m’ont aidé et encouragé tout au long de mes études, à mes frères et sœurs et à mon mari pour sa patience et son soutiens pendant la période ardue qu’est la rédaction. i Communications scientifiques La présente étude a été réalisée de septembre 2000 à juillet 2004 à l’Institut de Pharmacognosie et phytochimie (IPP) de l’Université de Lausanne, sous la direction de Monsieur le Professeur Kurt Hostettmann. Les résultats de ce présent travail ont été partiellement publiés ou présentés sous forme de posters lors de congrès internationaux : Publications Chaaib, F., Queiroz, E.F., Ndjoko, K., Diallo, D., Hostettmann, K. (2003). Antifungal and Antioxidant compounds from the root bark of Fagara zanthoxyloides. Planta Medica 69, 316- 320. Chaaib, F., Queiroz, E.F., Diallo, D., Hostettmann, K. (2004). A new endoperoxide from the root bark of Zanthoxylum zanthoxyloides (Lam.) Zepernick et Timler (Syn. Fagara zanthoxyloides L.), en preparation. Posters Chaaib, F., Queiroz, E.F., Diallo, D., Hostettmann, K. (2001). Antifungal compounds from the root bark of Fagara zanthoxyloides L. International Symposium of the Phytochemical Society of Europe (PSE), Lausanne, Switzerland, September 12-14, 2001. Chaaib, F., Queiroz, E.F., Ndjoko, K., Diallo, D., Hostettmann, K. (2002). Isolation of bioactive compounds from Fagara zanthoxyloides L. using CPC and dereplication of alkaloids by LC-MS. 50th Annual Congress of the Society for Medicinal Plant Research, Barcelona, Spain, September 8-12, 2002. ii Table des matières 1. BUT DU PRESENT TRAVAIL ............................................................................................ 1 2. INTRODUCTION.................................................................................................................. 5 2.1 Sélection des plantes et des extraits .................................................................................... 7 2.1.1 Introduction .................................................................................................................. 7 2.1.2 Critères de sélection des plantes................................................................................... 7 2.1.3 Critères de sélection des extraits .................................................................................. 9 2.2 La famille Rutaceae........................................................................................................... 11 2.2.1 Introduction ................................................................................................................ 11 2.2.2 Classification systématique et aspects botaniques ..................................................... 12 2.3 Présentation du genre Zanthoxylum (=Fagara)................................................................. 17 2.3.1 Introduction ................................................................................................................ 17 2.3.2 Caractéristiques botaniques de Zanthoxylum ............................................................. 17 2.3.3 Travaux antérieurs et principaux métabolites secondaires isolés du genre Zanthoxylum ......................................................................................................................... 18 2.3.3.1 Flavonoïdes ......................................................................................................... 18 2.3.3.2 Lignanes et composés apparentés........................................................................ 21 2.3.3.3 Alcaloïdes............................................................................................................ 22 2.3.3.4 Amides................................................................................................................. 25 2.3.3.5 Huiles essentielles ............................................................................................... 26 2.3.3.6 Coumarines.......................................................................................................... 27 2.3.3.7 Divers .................................................................................................................. 28 2.3.4 Propriétés biologiques et pharmacologiques de Zanthoxylum ................................... 30 2.3.4.1 Utilisation en médecine traditionnelle................................................................. 30 2.3.4.2 Activités biologiques reconnues.......................................................................... 31 2.3.5 Toxicité de Zanthoxylum............................................................................................ 31 2.4 Zanthoxylum zanthoxyloides (Lam.) Zepernick et Timler ................................................ 33 2.4.1 Introduction ................................................................................................................ 33 2.4.2 Aspects botaniques et répartition géographique......................................................... 34 2.4.3 Toxicité....................................................................................................................... 36 2.4.4 Travaux antérieurs sur Zanthoxylum zanthoxyloides (Lam.) Zepernick et Timler .... 36 2.5 Zanthoxylum macrophyllum Oliv...................................................................................... 38 2.5.1 Aspects botaniques et répartition géographique......................................................... 38 2.5.2 Travaux antérieurs sur Zanthoxylum macrophyllum Oliv.......................................... 38 2.6 Zanthoxylum madagascariensis Baker.............................................................................. 40 2.6.1 Aspects botaniques et répartition géographique......................................................... 40 2.6.2 Travaux antérieurs sur Zanthoxylum madagascariensis Baker.................................. 41 2.7 D’autres plantes utilisées en médecine traditionnelle dans l’hygiène buccale.................. 42 3. RESULTATS ....................................................................................................................... 45 3.1. Screening biologique des plantes récoltées au Mali.......................................................... 47 3.1.1. Introduction ................................................................................................................ 47 3.1.2. Discussion .................................................................................................................. 49 3.2. Investigation phytochimique de l’écorce de racines de Zanthoxylum zanthoxyloides (Lam.) Zepernick et Timler...................................................................................................... 51 iii 3.2.1. Introduction ...............................................................................................................
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