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Etude Phytochimique D'une Fabacée Tropicale, Lonchocarpus Nicou

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Etude Phytochimique D'une Fabacée Tropicale, Lonchocarpus Nicou UNIVERSITE DE LIMOGES ECOLE DOCTORALE Science – Technologie – Santé FACULTE de PHARMACIE Année : 2006 Thèse N° [ ] Thèse pour obtenir le grade de DOCTEUR DE L’UNIVERSITE DE LIMOGES Discipline / Spécialité : Sciences de la Vie et de la Santé Sciences Pharmaceutiques – Phytochimie/Biologie présentée et soutenue publiquement par Ata Martin LAWSON le 13 Juin 2006 ETUDE PHYTOCHIMIQUE D'UNE FABACEE TROPICALE, LONCHOCARPUS NICOU EVALUATION BIOLOGIQUE PRELIMINAIRE JURY : G. COMTE, Professeur, Université C. Bernard Lyon 1 Rapporteur M.-G. DIJOUX-FRANCA, MCF, Université J. Fourier Grenoble 1 Rapporteur M. KAOUADJI, Professeur, Université de Limoges Examinateur D. ALLAIS, MCF, Université de Limoges Directeur de thèse A. J. CHULIA, Professeur, Université de Limoges Co-Directeur de thèse J. FAVRE-BONVIN, Ingénieur de recherche, CNRS Président REMERCIEMENTS A Madame Daovy Paulette ALLAIS Maître de conférences en Pharmacognosie à la Faculté de Pharmacie de Limoges, Recevez ici mes sincères remerciements pour la confiance, les conseils et l'amitié que vous m'avez accordés tout au long de cette thèse. Merci également pour votre encadrement, votre disponibilité et votre gentillesse. Je n'oublie pas votre soutien moral qui m'a souvent aidé à remonter la pente dans les moments difficiles. A Monsieur Albert José CHULIA Professeur de Pharmacognosie à la Faculté de Pharmacie de Limoges, Veuillez trouver ici l’expression de ma gratitude pour m’avoir accueilli au sein de votre laboratoire. Soyez assuré de mon profond respect et de ma vive reconnaissance pour m’avoir fait bénéficier de votre expérience et de votre rigueur scientifique et professionnelle. A Monsieur Mourad KAOUADJI Professeur de Chimie à la Faculté des Sciences et Techniques de Limoges, A vrai dire, je ne sais pas comment vous remercier pour tout ce que vous m'avez apporté, transmis et appris lors de cette thèse. Merci pour l’énorme contribution que m’avez apportée afin de mener à bien ce projet. Soyez assuré de mon profond respect et de ma vive reconnaissance. A Monsieur Gilles COMTE Professeur à l'Université Claude Bernard Lyon 1, Veuillez trouver ici l’expression de ma profonde gratitude pour avoir accepté d'examiner ce travail et d'en être le rapporteur. Je vous prie de croire à ma respectueuse considération. 2 A Madame Marie-Geneviève DIJOUX-FRANCA Maître de conférences à la Faculté de Pharmacie de Grenoble, Je vous remercie pour l’intérêt manifesté à l’égard de ce travail en acceptant d’être le rapporteur. Je vous adresse ma profonde reconnaissance pour vos remarques et conseils en vue d’améliorer ce manuscrit. A Monsieur Jean FAVRE-BONVIN Recevez mes remerciements pour avoir accepté d’être membre de ce jury. A Monsieur Yves CHAMPAVIER Docteur en Phytochimie et Ingénieur de recherche du Service Commun de RMN de l'Université de Limoges, Je tenais à te remercier chaleureusement pour ton soutien moral et ton amitié. A Monsieur Jean-Louis BENEYTOUT Professeur de Biochimie à la Faculté de Pharmacie de Limoges, Veuillez trouver ici mes remerciements pour la réalisation des tests biologiques au sein de votre laboratoire. A Monsieur Bertrand LIAGRE Maître de conférences en Biochimie à la Faculté de Pharmacie de Limoges, Je voulais t'exprimer ainsi qu'à David toute ma reconnaissance pour les différents tests biologiques réalisés et votre contribution à la réussite de ce travail. A Madame Sandrine MARION-THORE Mes sincères remerciements pour les tests biologiques sur l'aromatase et les récepteurs aux estrogènes. 3 A Patrice FONDANECHE Merci pour ton soutien moral, pour ton aide technique et scientifique et pour ton amitié. A Samir YAHIAOUI Cher Samir, tu as toujours été à mes côtés et tu m'as toujours apporté ton soutien. Pour cela, je te remercie chaleureusement. Merci également pour ton amitié et j'espère que celle-ci continuera entre nous deux. A toute l’équipe «BIOMOLECULES ET THERAPIES ANTITUMORALES» A tous ceux qui de près ou de loin ont contribué à la réalisation et au bon déroulement de cette thèse. A mes frères et sœurs, à mes beaux-parents, et à tous mes amis 4 Je dédie spécialement cette thèse à ma femme et à mon fils Uriel qui m’ont toujours donné le sourire dans les moments difficiles, qui ont toujours su raviver en moi cette flamme de l'espoir pour qu'elle ne s'éteigne jamais. Je voudrais simplement leur dire que je les aime de tout mon cœur. Je la dédie également à mes parents pour leur soutien inébranlable et sans qui je ne serais pas là aujourd'hui. 5 TITRE "ETUDE PHYTOCHIMIQUE D'UNE FABACEE TROPICALE, LONCHOCARPUS NICOU EVALUATION BIOLOGIQUE PRELIMINAIRE " RESUME Cette thèse s’inscrit dans le cadre de la thématique de l'EA 4021 "Biomolécules et Thérapies Antitumorales". Elle vise essentiellement la recherche de molécules naturelles d’origine végétale, dotées d’une activité antitumorale. Lonchocarpus nicou (Aublet) D.C. est une liane tropicale de la famille des Fabacées, longtemps utilisée pour ses propriétés insecticide, acaricide et piscicide, attribuées généralement à des roténoïdes prénylés (roténone essentiellement). Ces roténoïdes dérivent biogénétiquement des isoflavonoïdes connus depuis longtemps pour leur activité estrogénique. Cela explique le choix de cette plante qui n’a pas fait l’objet d’une étude phytochimique complète, contrairement à d’autres espèces du même genre. En effet, une dizaine de composés seulement sont jusqu'alors connus de L. nicou. Nos travaux effectués concernent l'étude des extraits peu polaires (benzénique et hexanique) de la racine de cette plante. Ils sont développés et détaillés, après une description botanique de l'espèce et une présentation générale des molécules rencontrées dans le genre Lonchocarpus , puis dans l'espèce nicou . Cette étude phytochimique conduit à l'isolement et à la détermination structurale de trente huit molécules (dont trois sont à l'état de traces), grâce à l'utilisation de diverses techniques chromatographiques (CC, MPLC, CCM centrifuge, HPLC) et spectroscopiques (UV, RMN et SM). Ces résultats montrent une composition polyphénolique originale et diversifiée, caractérisée par quatre groupes de métabolites : chalcone (un composé), benzoquinone (un composé), isoflavonoïde (trente cinq composés) et un dérivé d'acide para coumarique (un composé). Outre la roténone, la déguéline et leurs deux dérivés 12a β-hydroxylés, qui s'accumulent préférentiellement dans la racine de cette plante, on distingue au niveau des autres phytocontituants mineurs treize composés naturels nouveaux et sept autres cités pour la première fois dans le genre. Ces quatre composés majeurs ont été testés par la suite, sur les récepteurs aux estrogènes, sur l'aromatase ainsi que sur deux lignées cellulaires cancéreuses : érythroleucémique humaine (cellules HEL), ostéosarcome humain (cellules 1547), en vue d'évaluer leurs activités antiproliférative et cytotoxique. Les résultats obtenus sont satisfaisants (IC 50 de l'ordre du nanomolaire) et ouvrent de nombreuses perspectives de recherche. Mots-clés : Lonchocarpus nicou , Fabacées, phytochimie, chalcone, isoflavonoïdes, roténoïdes, 6a,12a- didéhydroroténoïdes, 13-homo -13-oxa-6a,12a-didehydroroténoïdes, coumaronochromones, seco - roténoïdes, isolement, analyse structurale, évaluation biologique. 6 TITLE "PHYTOCHEMICAL STUDY OF A TROPICAL FABACEAE, LONCHOCARPUS NICOU PRELIMINARY BIOLOGICAL EVALUATION " ABSTRACT According to the topic of our research team EA 4021 "Biomolécules et Thérapies Antitumorales", phytochemical study of Lonchocarpus nicou (Aublet) D. C. was conducted in order to isolate natural molecules with antitumor or anticancer activity. Lonchocarpus nicou (Aublet) D. C. is a tropical liana of the Fabaceae family used for a long time for its insecticidal, acaricidal and piscicidal activities assigned to prenylated rotenoids (rotenone essentially). Rotenoids derived biogenetically from isoflavonoids known a long time ago for their estrogenic activity. That explains the choice of this plant which was not completely studied in contrary to those species of Lonchocarpus genus. Indeed, about ten compounds only were reported in previous study of this plant. After botanical description and presentation of previous phytochemical studies about Lonchocarpus genus and nicou specie, the least polar extracts (bezenic and hexanic) studied in this work was developed. Their investigation led to the isolation and structural elucidation of thirty-eight molecules (in which three ultra-minor compounds) by using various chromatographicals (CC, MPLC, centrifugal TLC, HPLC) and spectroscopics (UV, RMN and SM) techniques. This showed an original and diversified polyphenolic composition characterized by four groups of metabolites: chalcone (one compound), benzoquinone (one compound), isoflavonoid (thirty five compounds), and a para coumaric acid derivative (one compound). Besides rotenone, deguelin and their 12aβ-hydroxylated derivatives, which constituted the major components of the root of Lonchocarpus nicou , thirteen new metabolites were found in the other minor phytochemicals as well as seven other never cited before in Lonchocarpus genus. Preliminary bioassays were further conducted on the four main isolated components by evaluating their effect on estrogens receptors and on aromatase enzyme. Their antiproliferative activity and cytotoxic effect on HEL (Human Erythroleukemia) cells and 1547 cells (osteosarcoma) have been also investigated. The latter biological study gave interesting results (IC 50 about nanomolar) that might be explored by a solid scientific project. keywords: Lonchocarpus nicou ,
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