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Thesis Reference Thesis Contribution à la connaissance taxonomique et chimique de fruits africains du genre "Detarium" (Fabaceae - Caesalpinioideae) : "D. microcarpum" Guill. et Perr. et des formes comestibles et toxiques de "D. senegalense" J.F. Gmel CAVIN, Anne-Laure Abstract Une révision de la littérature concernant des espèces du genre "Detarium" (Fabaceae Caesalpinioideae), ainsi que l'analyse des profils chromatographiques des extraits MeOH et dichlorométhanique de certains fruits, a permis de clarifier la situation botanique au sein du genre. Une première partie pratique présente l'investigation phytochimique des fruits de "D. microcarpum" qui a mené à l'isolement de six diterpènes de type labdane et clérodane. Quatre des clérodanes possèdent une configuration relative nouvelle et l'acide 3β,4β-èpoxy-5β,10β-cis-17β,20α-ent-clérod-13E-èn-15-oïque est décrit ici pour la première fois. Les composés à l'origine de la toxicité des fruits de "D. senegalense" sont inconnus. Dans un second temps, nos travaux ont mené à l'isolement d'un nouveau glucoside cyanogénétique, le 6'-O-galloyl-(R)-épihétérodendrine, qui est fortement suspecté comme pouvant être responsable. En effet, il existe certaines similitudes entre les symptômes survenant lors d'une intoxication au cyanure et suite à l'ingestion de ces fruits. Reference CAVIN, Anne-Laure. Contribution à la connaissance taxonomique et chimique de fruits africains du genre "Detarium" (Fabaceae - Caesalpinioideae) : "D. microcarpum" Guill. et Perr. et des formes comestibles et toxiques de "D. senegalense" J.F. Gmel. Thèse de doctorat : Univ. Genève, 2007, no. Sc. 3838 URN : urn:nbn:ch:unige-4930 DOI : 10.13097/archive-ouverte/unige:493 Available at: http://archive-ouverte.unige.ch/unige:493 Disclaimer: layout of this document may differ from the published version. 1 / 1 UNIVERSITÉ DE GENÈVE FACULTÉ DES SCIENCES Section des Sciences Pharmaceutiques Laboratoire de Pharmacognosie et Phytochimie Professeur K. Hostettmann Contribution à la connaissance taxonomique et chimique de fruits africains du genre Detarium (Fabaceae - Caesalpinioideae) : D. microcarpum Guill. et Perr. et des formes comestibles et toxiques de D. senegalense J.F. Gmel. THÈSE présentée à la Faculté des sciences de l’Université de Genève pour obtenir le grade de Docteur ès sciences, mention sciences pharmaceutiques par Anne-Laure Cavin de Vulliens (VD) Thèse N° 3838 Genève Atelier de reproduction de la Section de physique 2007 Remerciements Je tiens d’abord à remercier mon directeur de thèse, Monsieur le Professeur Kurt Hostettmann, pour m’avoir accueillie au sein de son laboratoire et permis de réaliser mon travail de doctorat. C’est dans ce laboratoire de renommée mondiale et présentant un environnement stimulant que j’ai eu le plaisir de passer ces quelques années. J’ai également apprécié de profiter des conseils du Docteur Andrew Marston. Je remercie également le Professeur Kurt Hostettmann de m’avoir permis de présenter quelques uns de mes résultats lors de congrès nationaux et internationaux. Mes remerciements vont aussi aux membres de mon jury de thèse : Monsieur le Professeur Peter Rüedi (Institute of Organic Chemistry, University of Zürich), Monsieur le Docteur Olivier Potterat, (Institut für Pharmazeutische Biologie, Universität Basel), Monsieur le Docteur Gino Müller (Musée et jardins botaniques cantonaux, Lausanne) et Monsieur le Docteur Andrew Marston (Laboratoire de Pharmacognosie et Phytochimie, Université de Genève). Outre le fait qu’ils aient accepté de participer en tant que membres du jury, je les remercie sincèrement pour les discussions très enrichissantes que nous avons eues lors mon examen. J’ai eu l’opportunité, durant ce travail, de réaliser plusieurs collaborations. Je suis notamment très reconnaissante envers le Professeur Duilio Arigoni (ETH, Zürich), pour avoir partagé avec moi ses connaissances au sujet de la stéréochimie des clérodanes. Je remercie également le Docteur Rosario Scopelliti (EPFL, Lausanne) et le Professeur Helen Stoeckli-Evans (Université de Neuchâtel, Neuchâtel) pour les mesures et interprétations de diffractions aux rayons X, effectuées sur deux des composés isolés. C’est grâce au Professeur Pierre-Alain Carrupt et à son équipe (Laboratoire de Pharmacochimie, Université de Genève) que des tests en solution d’inhibition de l’enzyme acétylcholinestérase ont pu être réalisés. Je remercie encore le Professeur M.C. Recio (Departament de Farmacologia, Universitat de València, Espania) pour les tests de cytotoxicité effectués sur l’un des composés. Je remercie aussi Jonathan Kissling pour ses judicieux conseils sur la partie botanique de ce travail, et Assane El Diop pour être allé chercher au Sénégal une thèse portant sur les fruits toxiques de Detarium. Je remercie également tous mes collègues du Laboratoire de Pharmacognosie et Phytochimie, pour m’avoir encouragée et pour les bons moments passés ensemble. Une mention particulière pour Anne- Emmanuelle Hay qui m’a énormément soutenue et guidée dans ce travail. Merci aussi à Karine, Martine, Fred, Caroline, Aline, Daphné, Aurélie, Sandra et tous les autres, sans oublier mes ex- collègues Anne-Laure, Milena, Julien, Jean-Robert. Sans leur serviabilité, leurs encouragements et la bonne ambiance qu’ils créaient, mes années de thèse auraient eu une toute autre saveur. Et finalement, mille mercis à ma famille et à mes amis qui m’ont particulièrement épaulée durant cette année 2006. i COMMUNICATIONS SCIENTIFIQUES Ce travail de thèse a été réalisé d’avril 2002 à janvier 2007 à l’Institut de Pharmacognosie et Phytochimie (IPP) de l’Université de Lausanne (avril 2002 à septembre 2004), et au Laboratoire de Pharmacognosie et Phytochimie (LPP) de l’Université de Genève (septembre 2004 à janvier 2007), sous la direction de Monsieur le Professeur Kurt Hostettmann. Certains aspects du present travail ont été partiellement publiés ou présentés lors de congrès internationaux sous forme de posters. Publications Cavin, A.L., Hay, A.E., Marston, A., Stoeckli-Evans, H., Scopelliti, R., Diallo, D. and Hostettmann, K. (2006). Bioactive diterpenes from the fruits of Detarium microcarpum. J. Nat. Prod. 69, 768-773. Cavin, A.L., Arigoni, D., Hay, A.E. and Hostettmann, K. Revision of relative configurations of some clerodane diterpenes (en préparation). Cavin, A.L., Hay, A.E. and Hostettmann, K. Cyanogenic glycoside derivative from the toxic fruit of D. senegalense J.F. Gmel. (en préparation). Posters Cavin, A.L., Marston, A. and Hostettmann, K. (2004). Diterpenes isolated from the fruits of Detarium microcarpum Guill. et Perr. Fall Meeting 2004 of the Swiss Chemical Society, Zürich, Switzerland, October 7, 2004. Cavin, A.L., Hay, A.E., Marston, A., Scopelliti, R., Diallo, D. and Hostettmann, K. (2005). Isolation of new bioactive diterpenes from Detarium microcarpum Guill. & Perr. Phytotherapy : The role of an ancient tradition in modern times, Madeira, Portugal, November 1-5, 2005. iii TABLE DES MATIERES REMERCIEMENTS…………………….......……………………….......………...………………..……i COMMUNICATIONS SCIENTIFIQUES ………………………….......………...………………..…..iii TABLES DES FIGURES ET TABLEAUX ………………………….......………...…………………..ix ABREVIATIONS, SYMBOLES ET CONVENTIONS …...……………………….......……………….xiii 1. BUTS DU TRAVAIL …………...……………….......………………………………………..1 2. INTRODUCTION …...…………………………….......……………………………...………5 2.1 Considérations écologiques et climatiques en Afrique de l’Ouest …...………..………....9 2.2 La sous-famille Caesalpinioideae …...……..…………………..……………..……...….12 2.3 Traitement taxonomique du genre Detarium Juss …...…………..………………..…….15 2.3.1 Description botanique …..……..…………………..…………………..……......….15 2.3.2 Espèces du genre Detarium …...……..………………..…………….………..….…16 2.3.3 Confusions botaniques …...……..…………………..……………………..…....….18 2.3.3.1 Présentation de la problématique et causes ...………..…………….………….18 2.3.3.2 Clarification de la situation botanique …………….……………….……....….24 2.4 Présentation de Detarium microcarpum Guill. & Perr. …………..………………….….38 2.4.1 Caractères morphologiques et répartition géographique ...……...…..…..……..…...38 2.4.2 Utilisations traditionnelles ...………..…………………..………….........…..…..….40 2.4.3 Etudes phytochimiques antérieures …..……..…………………..………….…...….43 2.4.3.1 Métabolites primaires ...………..…………………..…………………....…….43 2.4.3.2 Métabolites secondaires et leurs activités ...………..……………………....….44 2.4.3.3 Activités reportées pour D. microcarpum Guill. et Perr. …..….………...…….51 2.5 Présentation de Detarium senegalense J.F. Gmel. …………..………….………..……...54 2.5.1 Caractères morphologiques et répartition géographique ...………..……….........….54 2.5.2 Utilisations traditionnelles ...………..……………….…………………..……...…..56 2.5.2.1 Forme comestible de Detarium senegalense J.F. Gmel. ………..…...........…..57 2.5.2.2 Forme toxique de Detarium senegalense J.F. Gmel. …………………...……..60 2.5.3 Toxicité du genre : aspects cliniques ...………..…………………..………….…….61 2.5.4 Etudes phytochimiques antérieures ...………………………………….……….…..66 2.5.4.1 Forme comestible de Detarium senegalense J.F. Gmel. ………...…………....66 2.5.4.2 Forme toxique de Detarium senegalense J.F. Gmel. ………..…………...........67 v 3. RESULTATS ...………………………………..…………….......………………………...…71 3.1 Préparation des extraits ...……………………………………………………………......73 3.2 Analyses préliminaires ...………………………………………………………...………75 3.2.1 Elimination des sucres ………………...………………………………………........76 3.3 Criblage préliminaire des extraits bruts ……………...……………………..………...…78 3.4 Investigation phytochimique de Detarium microcarpum Guill. et Perr. ………..………83 3.4.1 Fractionnement de l’extrait dichlorométhanique
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