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Contribution À L'étude Phytochimique De Galega Officinalis L. (Fabaceae)

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Contribution À L'étude Phytochimique De Galega Officinalis L. (Fabaceae) N° D’ORDRE 2206 THÈSE D’ÉTAT présentée pour obtenir le grade de DOCTEUR DE L’INSTITUT POLYTECHNIQUE DE TOULOUSE Ecole doctorale : Sciences des Procédés Spécialité : Sciences des Agroressources Discipline: Pharmacognosie elle Par M Céline PEIRS CONTRIBUTION A L’ETUDE PHYTOCHIMIQUE DE GALEGA OFFICINALIS L. (FABACEAE) Soutenue le 11 mars 2005 à 14 heures devant le jury composé de : M. P. MORARD, Professeur, ENSAT Toulouse Président M. R. ANTON, Professeur, ULP Strasbourg Rapporteur M. J. BOUSTIE, Professeur, Université de Rennes Rapporteur M. N. FABRE, Maître de Conférences, UPS Toulouse Examinateur Mme I. FOURASTE, Professeur, UPS Toulouse Examinateur M. G. MASSIOT, Directeur de recherche, ISTMT, Pierre Fabre-CNRS, Toulouse Examinateur M. C. PRZYBYLSKI, Directeur de l’IDPF, Institut de Recherche Pierre Fabre, Ramonville Invité Codirecteurs des Travaux de Recherche : Pr. I. FOURASTE et Dr. N. FABRE Laboratoire Pharmacochimie des Substances Naturelles et Pharmacophores Redox UMR 152, Faculté des Sciences Pharmaceutiques, 35 chemin des Maraîchers, 31062 Toulouse Cedex 4 – France. A mes parents. A mon frère Eric et son épouse Karine. A mes amis pour leur présence et leur soutien. A ma moitié, Sébastien. À notre président de Thèse, Monsieur le Professeur Philippe MORARD, Professeur à l’Ecole Nationale Supérieure d’Agronomie de Toulouse. Nous vous remercions vivement d’avoir accepté de juger ce travail. Nous tenons à vous remercier d’avoir contribué à ce que ce jour devienne le notre lorsque vous nous avez accueillie au sein de votre DEA. Nous sommes touchée de la confiance que vous avez su nous témoigner et des conseils que vous nous avez prodiguée. Nous sommes particulièrement honorée de vous avoir vu assurer la Présidence de ce Jury de Thèse. A notre Jury de Thèse, Monsieur le Professeur Robert ANTON, Professeur de Pharmacognosie à l’Université Louis Pasteur de Illkirch. Qu’il nous soit ici permis de vous remercier très sincèrement pour avoir accepté de juger ce travail malgré vos nombreuses obligations. Nous sommes très sensible à l’honneur que vous nous faites d’en être le rapporteur. Nous sommes très honorée d’avoir bénéficié de vos critiques et tenons à vous assurer de notre grande estime et de notre profonde gratitude. Monsieur le Professeur Joël BOUSTIE, Professeur de Pharmacognosie à l’Université de Rennes I. Vous avez, avec beaucoup de gentillesse et d’enthousiasme, accepté de juger ce travail. Nous sommes très sensible à l’honneur que vous nous faites de siéger à ce jury en tant que rapporteur. Nous sommes très reconnaissante de vos remarques et conseils éclairés et tenons à vous assurer de notre considération la plus respectueuse. Monsieur Georges MASSIOT, Directeur du Centre de Recherches sur les Substances Naturelles, ISTMT. Nous avons tout particulièrement souhaité à ce que vous soyez membre de ce jury de thèse. Vous avez bien voulu vous intéresser à ce travail malgré vos obligations et nous en sommes sincèrement honorée. Nous tenons à vous remercier de l’accueil ouvert et aimable que vous nous avez toujours réservée au cours de ces derniers mois Nous sommes très heureuse d’avoir pu bénéficier de vos remarques pertinentes et tenons à vous assurer de notre profonde gratitude pour nous avoir fait partager un peu de votre savoir sur les triterpènes. Monsieur Nicolas FABRE, Docteur en Pharmacognosie à la faculté des Sciences Pharmaceutiques de Toulouse. Nous tenons à vous remercier pour vos conseils dispensés au cours de quatre années passées au sein du laboratoire. Vous nous avez fait profiter de votre savoir malgré votre emploi du temps extrêmement chargé durant ces trois dernières années. Vous avez su nous faire confiance et vous nous avez donné l’opportunité de nous investir, certes à notre échelle, dans la gestion matérielle et humaine. Vous avez fait naître la motivation nécessaire pour mener à bien ce travail de recherche et vous nous avez appris à voir bien au-delà. Veuillez trouver ici le témoignage de notre très sincère gratitude. Madame le Professeur Isabelle FOURASTE, Professeur en Pharmacognosie à la faculté des Sciences Pharmaceutiques de Toulouse. Nous tenons à vous remercier très chaleureusement de votre accueil au sein du laboratoire de Pharmacognosie de Toulouse, véritable petite famille qui nous a véritablement aidée à grandir. Vous nous avez sensibilisée à votre science et nous n’oublierons jamais votre enthousiasme, votre générosité ni votre charisme. Nous avons été profondément touchée par vos encouragements et la confiance que vous nous avez accordée. Qu’il nous soit ici permis de vous témoigner de notre profonde gratitude et de notre sincère amitié. Monsieur Christophe PRZYBYLSKI, Directeur de l’Institut de Développement Pierre Fabre, IRPF. Nous sommes particulièrement honorée de votre présence aux côtés des membres du jury malgré vos très nombreuses obligations. Nous tenons tout particulièrement à vous remercier de votre contribution à ce travail en nous ayant donné l’opportunité, depuis bientôt trois ans, d’être sensibilisée au monde de l’industrie pharmaceutique et de nous impliquer tous les jours un peu plus au sein de l’Institut de Recherche Pierre Fabre. Qu’il nous soit ici permis de vous témoigner de notre sincère reconnaissance. Monsieur le Professeur Claude MOULIS Professeur en Pharmacognosie à la faculté des Sciences Pharmaceutiques de Toulouse. Nous avons eu la chance de vous connaître et de partager avec vous la vie du laboratoire. Nous avons eu, quelques fois, pu bénéficier de vos conseils et de votre expérience en matière de recherche. Vous avez très gentiment accepté de participer aux corrections des premiers « jets » de ce manuscrit et nous vous en sommes extrêmement reconnaissante. Nous conserverons le souvenir d’un véritable chercheur, doté d’un humour remarquable et d’une véritable gentillesse. Monsieur le Professeur Edouard STANISLAS Professeur en Pharmacognosie à la faculté des Sciences Pharmaceutiques de Toulouse. Très cher Monsieur Stanislas, je suis extrêmement heureuse d’avoir pu vous connaître et d’avoir eu la preuve vivante que la passion des Sciences persiste bien au-delà d’une simple carrière. Vous êtes un sacré Monsieur. Vous avez toujours été d’une extrême gentillesse à notre égard, vous avez toujours su nous encourager et vous n’avez jamais douté de notre volonté et de nos aptitudes à triompher. Nous tenons à vous exprimer notre profond respect. Nous ne manquerons pas de remercier toutes les personnes qui ont apporté leur contribution à notre travail Madame Valérie SOHIER, Chef de Projet dans le service de Développement en Phytothérapie au sein de l’IDPF et coordinatrice scientifique de ce travail, Marie CHARVERON, Responsable du Service de Biologie Cellulaire Cutanée Laboratoires Pierre FABRE, ainsi que Mme Isabelle CERUTI, pour nous avoir accueillie au sein de son unité afin de nous permettre la mise en œuvre d’une importante partie de notre étude. L’équipe du service commun de RMN de l’UPS, l’équipe du service de spectrométrie de masse de l’UPS, M. Christophe LONG de l’ ISTMT ainsi que Melle Min GAO. Enfin, nous tenons à remercier tout particulièrement Madame Marie-Thérèse FAUVEL pour sa disponibilité, ses conseils et sa gentillesse et sa participation active aux préparations culinaires festives pour régaler l’équipe. Valérie, pour son amitié et son écoute. Ces moments partagés resteront dans mon esprit et nous lui souhaitons tout le meilleur ainsi qu’à sa petite famille. Fatiha, Lise, Mme Ha. Valé, Sèverine, Jalloul, Karine et Marie-Carmen pour leur amitié et leur présence. Nous avons partagé de longs mois côte à côte. Je tiens encore à vous remercier pour tout ce que vous m’avez appportée. Karine et Marie-Carmen, je garde au fond du cœur nos franches « rigolades » qui faisaient tant de bien… Une pensée pour les anciens du labo, Cédric, Antoine et Claire et aussi pour tous les derniers venus que je ne citerai pas. Claire, je te suis infiniment reconnaissante pour les heures tardives que tu as choisi de passer à mes côtés sur les spectres de RMN… Tous tes conseils, ta bonne humeur, ton soutien dans mes galères de thèse, tu fais partie des rares qui se sont impliqués dans mes moments difficiles. Christelle pour ton amitié avant tout et pour tous les conseils que tu as su m’apporter. Pour ta présence… Tu as toujours été là pour me raisonner et m’aider à faire face aux difficultés. Tu m’as véritablement apporté une aide précieuse et j’espère te garder parmi mes proches aussi longtemps que possible. Enfin mes pitchous qui sont encore en phase d’apprentissage, Amélie, Vincent et Bénédicte. Je vous souhaite une bonne route à tous les trois. Surtout, que mon expérience vous soit utile à tout niveau. ABREVIATIONS ET SYMBOLES Biologie et biochimie Acétyl-CoA acétyl-coenzyme A ADN acide désoxyribonucléique ARN acide ribonucléique ATP adénosine-5’ tri-phosphate CPP-ME 4-diphosphocytidyl-2-C-méthyl-D-érythritol CPP-ME2P 4-diphosphocytidyl-2-C-méthyl-D-érythritol-2-phosphate CTP copalyl triphosphate Co2+ ion Cobalt DMAPP diméthylallyl di-phosphate DOXP 1-déoxy-D-xylulose-5-phosphate/ Voie du déoxy-xylulose phosphate DOXPR DOXP réductoisomérase DOXPS DOXP synthétase ER = RE récepteur œstrogénique ERE éléments de réponse aux récepteurs œstrogéniques FPP farnésyl di-phosphate Gal galactose Glc glucose Glcpy glucopyranose Glu acide glutamique GPP géranyl di-phosphate GFPP géranylfarnésyl di-phosphate His histidine GGPP géranylgéranyl di-phosphate HMBPP 1-hydroxy-2-méthyl-2(E)-butényl-4- di-phosphate HMG-CoA 3-hydroxy-3-méthylglutaryl-Coenzyme A HMGR HMG-CoA réductase IDS HMBDP
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