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Etude De La Voie De Biosynthèse De La Galanthamine Chez Leucojum Aestivum L.: Criblage Phytochimique De Quelques Amaryllidaceae

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Etude De La Voie De Biosynthèse De La Galanthamine Chez Leucojum Aestivum L.: Criblage Phytochimique De Quelques Amaryllidaceae Etude de la voie de biosynthèse de la galanthamine chez Leucojum aestivum L. : criblage phytochimique de quelques amaryllidaceae Anna El Tahchy To cite this version: Anna El Tahchy. Etude de la voie de biosynthèse de la galanthamine chez Leucojum aestivum L. : criblage phytochimique de quelques amaryllidaceae. Autre. Université Henri Poincaré - Nancy 1, 2010. Français. NNT : 2010NAN10072. tel-01748647 HAL Id: tel-01748647 https://hal.univ-lorraine.fr/tel-01748647 Submitted on 29 Mar 2018 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. AVERTISSEMENT Ce document est le fruit d'un long travail approuvé par le jury de soutenance et mis à disposition de l'ensemble de la communauté universitaire élargie. Il est soumis à la propriété intellectuelle de l'auteur. Ceci implique une obligation de citation et de référencement lors de l’utilisation de ce document. D'autre part, toute contrefaçon, plagiat, reproduction illicite encourt une poursuite pénale. Contact : [email protected] LIENS Code de la Propriété Intellectuelle. articles L 122. 4 Code de la Propriété Intellectuelle. articles L 335.2- L 335.10 http://www.cfcopies.com/V2/leg/leg_droi.php http://www.culture.gouv.fr/culture/infos-pratiques/droits/protection.htm G roupe SUCRES S R S MC UMR 7565 Faculté des Sciences École Doctorale S.E.S.A.M.E.S. THESE Présentée pour l’obtention du titre de Docteur de l’Université Henri Poincaré, Nancy-Université en Chimie par Anna El Tahchy Étude de la voie de biosynthèse de la galanthamine chez Leucojum aestivum L. – Criblage phytochimique de quelques Amaryllidaceae The Study of galanthamine biosynthesis pathway in Leucojum aestivum L. – Phytochemical screening of some Amaryllidaceae plants. Thèse dirigée par : Pr. D. Laurain-Mattar Soutenue le 13 Octobre 2010, devant le jury composé de : Rapporteurs : Dr. Roger Lteif, Université Saint Joseph, Beyrouth Pr. François Tillequin, Université de Paris V Examinateurs : Dr. Yves Chapleur, Université Henri Poincaré, Nancy Dr. Catherine Guillou, ICSN CNRS, Gif-sur-Yvette Dr. Alain Hehn, ENSAIA-INPL-INRA, Nancy Pr. Richard Maroun, Université Saint Joseph, Beyrouth Dr. Agata Ptak, Université d’Agriculture, Cracovie Pr. Dominique Laurain-Mattar, Université Henri Poincaré, Nancy Invité : Pr. Toufic Rizk, Université Saint Joseph, Beyrouth Groupe SUCRES, UMR S.R.S.M.C. 7565 – C.N.R.S. Nancy – Université Faculté des Sciences et Techniques, Université Henri Poincaré Nancy Université BP 239, F-54506 Vandoeuvre-lès-Nancy À ma famille, Ramzy, Aida, Youmna et Elie, en témoignage de ma profonde gratitude, Au feu de mes grands-parents, et À ma grand-mère, À Katie et mes chers cousins, À Billy, et À tous les amis. Remerciements Les présents travaux ont été réalisés au groupe SUCRES de l’UMR 7565 – CNRS UHP Nancy-1. Je tiens à exprimer tout d’abord mes remerciements aux membres du jury, qui ont accepté d’évaluer mon travail de thèse. Ensuite, je tiens à remercier Monsieur le Dr. Yves Chapleur, directeur du groupe SUCRES, qui m’a donné l’occasion de vivre cette expérience en m’accueillant au sein de son laboratoire. Mes plus grandes gratitudes vont également à Madame le Professeur Dominique Laurain-Mattar, ma directrice de thèse, pour m’avoir prise en main, et m’a transmis avec passion ses connaissances et avec qui j’ai partagé mes lots de joies et de peines quotidiennes. Ses encouragements, ses conseils et son attention m’ont permis de mener ces études doctorales dans les meilleures conditions. Je suis tout particulièrement reconnaissante au Professeur Max Henry, pour tous ses conseils relatifs au projet et à la recherche en général, et pour tous les bons moments partagés au cours de ces années. Messieurs Roger Lteif, Professeur associé à la faculté des sciences à l’Université Saint Joseph-Beyrouth, et François Tillequin, Professeur à l'Université Paris Descartes et chef de service de Pharmacognosie et Chimie des Substances Naturelles, qui ont accepté d'être les rapporteurs de cette thèse, et je les en remercie, de même que pour leur participation au Jury, et je leur en suis très reconnaissante. Les travaux présentés n’auraient probablement pu aboutir sans la collaboration des chercheurs, Messieurs le Professeur Frédéric Bourgaud, le Dr. Alain Hehn, du laboratoire Agronomie et Environnement UMR 1121-INPL-INRA-ENSAIA ; le Dr. Michel Boisbrun, le Dr. Jean-Pierre Jolie et le Dr. Françoise Chrétien du groupe SUCRES ; le Dr. Agata Ptak de l’Université de Cracovie ; et le Dr. Catherine Guillou de l’Institut de Chimie des Substances Naturelles (ICSN). Mes plus grands remerciements vont à Monsieur l’ingénieur François Dupire pour la compétence, la gentillesse et la patience qu'il a manifestées à mon égard durant cette thèse, pour tous les conseils et les analyses chromatographiques qu'il a bien voulu me fournir. Je remercie vivement tous les anciens et actuels stagiaires et thésards, surtout Céline, Ismael, Charlotte, Tsvetelina, Tanya, Fany, Simon et Sakina, avec qui nous avons travaillé dans la bonne humeur et qui ont effectué une partie des manipulations lors de leur stage de BTS, SIR, Master et ERASMUS, et aux autres membres du laboratoire et chercheurs étrangers de passage, avec qui nous avons beaucoup échangé. Je passe ensuite une dédicace spéciale à tous les jeunes gens que j'ai eu le plaisir de côtoyer durant ces quelques années à Nancy, à savoir les frères Chadi, Jihad et Edward Ghaoui, Rana El Zein, Nicole El Zoghbi et Père Sayed Marroun. Un grand bonjour à la famille Mattar, à Salem Hannoun, et à mes très chers cousins Elias et Mario Tahchi pour leurs encouragements et le soutien sans faille qu’ils ont su m’apporter durant mon séjour en France. Pour l’encouragement et l’assistance aussi bien matérielle que morale qui m'ont permis de faire cette thèse dans de bonnes conditions, je remercie chaudement Mr. Hussein Machmouchi et sa compagnie New Nouvelle Pharm qui a financé une bonne partie de mes études. Je tiens à remercier chaleureusement Dr. Bilel Nefzi (Billy) pour son humour, son soutien, sa patience, sa tolérance, sa sollicitude et pour tous les moments magiques et les aventures que nous avons partagés. J’adresse un grand merci à toute ma famille qui a toujours été présente lorsque j’en ai eu besoin, en particulier à ma sœur, à mon frère, à mon père et à ma mère. LISTE DES ABRÉVIATIONS 2,4-D : acide 2,4-Dichlorophénoxyacétique ACC : L’acide 1-aminocyclopropane-1-carboxylique (ACC) AChE : Enzyme acétylcholinestérase ANA : L'acide naphtalène acétique BAP : 6-benzylaminopurine (ou benzyladénine) BME : ß-mercaptoéthanol BSA : Boeuf sérum albumine ChanB : Canal B de la lampe UV (280 nm) CLHP : Chromatographie Liquide Haute Performance CLHP-UV : CLHP couplée à un détecteur UV CoA : Coenzyme A CYP : Cytochrome P450 D3ISO : Isovanilline deutérée D3MN : 4’-O-méthylnorbelladine deutérée EDTA : Ethylène diamine tétraacétate eV : electron-Volt GCMS : Chromatographie Gazeuse couplée à la Spectrométrie de Masse GD3 : Galanthamine deutérée HPTLC-MS : Chromatographie sur couche mince couplée à la spectrométrie de masse, High Pressure Thin Layer Chromatography coupled to Mass Spectrometry Inh : Inhibition LCMS : Chromatographie Liquide couplée à la Spectrométrie de Masse LD2 : Lycorine deutérée LDD : Limite de détection MeJa : Méthyljasmonate MeOH : Méthanol MF : Matière Fraîche MS : Matière Sèche MS30 : Milieu Murashige & Skoog additionné de 30 g/L de saccharose MS60 : Milieu Murashige & Skoog additionné de 60 g/L de saccharose NADPH : Nicotinamide adénine dinucléotide phosphate RF : Facteur de rétention STS : Thiosulfate d’argent (Silver Thiosulfate) SAM : S-adénosyl méthionine TEAA : Tampon d'acétate de triéthylammonium TEG : Tétraéthylèneglycol Tr : Temps de rétention U : Ultrasons UHQ : Ultra Haute Qualité UV : Ultra Violet TABLE DES MATIÈRES INTRODUCTION................................................................................................................................................. 1 OBJECTIFS .......................................................................................................................................................... 5 SYNTHESE BIBLIOGRAPHIQUE.................................................................................................................... 7 A- MALADIE D’ALZHEIMER ET TRAITEMENTS ....................................................................................... 8 1. Traitements de la maladie d’Alzheimer......................................................................................... 10 a. Les traitements des troubles psychocomportementaux : ................................................................................ 10 b. Les traitements des troubles cognitifs :.......................................................................................................... 10 2. Médicaments d’origine naturelle utilisés dans le traitement de la maladie d’Alzheimer.......... 11 B- LA FAMILLE DES AMARYLLIDACEAE ............................................................................................... 13 1. Lycoris :............................................................................................................................................
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