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Contribution À L'étude De L'origine Naturelle Du Tramadol Et Étude

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Contribution À L'étude De L'origine Naturelle Du Tramadol Et Étude Contribution à l’étude de l’origine naturelle du tramadol et étude phytochimique de deux plantes alpines Mathieu Agostini To cite this version: Mathieu Agostini. Contribution à l’étude de l’origine naturelle du tramadol et étude phytochimique de deux plantes alpines. Chimie organique. Université Grenoble Alpes [2020-..], 2020. Français. NNT : 2020GRALV007. tel-03122786 HAL Id: tel-03122786 https://tel.archives-ouvertes.fr/tel-03122786 Submitted on 27 Jan 2021 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. THÈSE Pour obtenir le grade de DOCTEUR DE L’UNIVERSITE GRENOBLE ALPES Spécialité : Phytochimie - Pharmacognosie Arrêté ministériel : 25 mai 2016 Présentée par Mathieu AGOSTINI Thèse dirigée par Pr. Ahcène BOUMENDJEL Co-encadrée par Dr. Benjamin BOUCHERLE préparée au sein du Département de Pharmacochimie Moléculaire dans l'École Doctorale Chimie et Sciences du Vivant Contribution à l’étude de l’origine naturelle du tramadol et étude phytochimique de deux plantes alpines Thèse soutenue publiquement le 7 septembre 2020, devant le jury composé de : Madame Martine DEMEUNYNCK Directrice de Recherche, Université Grenoble-Alpes, Présidente du jury Madame Angèle Lengo MAMBU Professeur des Universités, Université de Limoges, Rapporteur Monsieur Nicolas FABRE Professeur des Universités, Université de Toulouse, Rapporteur Madame Isabelle HININGER-FAVIER Maître de Conférences, Université Grenoble-Alpes, Examinateur Monsieur Emerson FERREIRA QUEIROZ Maître de Conférences, Université de Genève, Examinateur Monsieur Ahcène BOUMENDJEL PREX, Université Grenoble-Alpes, Directeur de thèse Monsieur Benjamin BOUCHERLE Maître de Conférences, Université Grenoble-Alpes, Invité, Co-encadrant de thèse Cette thèse est dédiée à ma famille, à mon Papa, parti beaucoup trop tôt… 1 Remerciements Je tiens, tout d’abord, à exprimer ma gratitude au Pr. Ahcène Boumendjel de m’avoir fait confiance pour mener à bien cette thèse pendant ces trois années. Son expertise et sa constante attention m’ont permis d’obtenir la meilleure aide possible. Sa gentillesse, sa patience, sa sympathie ainsi que sa bonne humeur ont su me rassurer lors des moments de doute et de difficulté pendant ce doctorat. Je ne pouvais pas rêver mieux pour un directeur de thèse. Nos cafés le matin me manqueront, chef ! Je souhaite également remercier mon co-encadrant de choc, le Dr. Benjamin Boucherle, pour son aide et son encadrement. Félicitations à toi pour m’avoir supporté pendant cette première année dans le même bureau ! Ton humour, ta gentillesse, nos discussions scientifiques (Dis-moi, Ben…) et sur la vie (et les pintes en afterwork) vont indéniablement me manquer. Je n’aurai pas pu réussir sans ton aide, Ben ! Je voudrais remercier les membres du jury de m’avoir fait l’honneur de lire mon manuscrit et de juger mes travaux : Dr. Martine Demeunynck et Dr. Isabelle Hininger de l’Université de Grenoble-Alpes, Pr. Angèle Lengo de l’Université de Limoges, Pr. Nicolas Fabre de l’Université de Toulouse et Dr. Emerson Ferreira Queiroz de l’Université de Genève. Un grand merci à tout le Département de Pharmacochimie Moléculaire pour leur soutien. Je n’oublierai jamais le grand et fameux humour de Basile, la gentillesse de Marine, les longues discussions avec Romain ainsi que tout le reste du laboratoire. Une petite mention spéciale pour « le cœur du DPM » : la bonne humeur de Pascale et la douceur d’Angèle. Je remercie bien évidemment tous mes amis du laboratoire pour leur soutien (mes acolytes Emile et Brayan, ma petite Farda, notre basque incontournable Jaione, mes italiennes préférées : Silvia et Lorena, Florian, Julie, Rayssa, Sara, Léandro, Kim-Anh, Anthonin, Cyril, Bastien, Pascal et sans oublier nos meilleurs stagiaires Alexandra, Justine et Younès. Un énorme merci à tous les doctorants et docteurs que j’ai pu rencontrer pendant cette thèse : Pierre, Vincent, Romy, Marie, Delphine et Diana ! Je vous souhaite à tous une bonne continuation. Je souhaite remercier l’IDEX pour sa contribution au financement de mon séjour scientifique au laboratoire de Phytochimie et produits naturels bioactifs à l’Université de Genève dirigé par le Pr. Jean-Luc Wolfender. 2 Merci au Pr. Jean-Luc Wolfender de m’avoir accueilli au sein de son laboratoire pour mener à bien mes travaux de purification d’extraits et d’isolement de molécules. Une sincère gratitude au Dr. Emerson Ferreira Queiroz pour son encadrement pendant mon séjour, au Dre. Laurence Marcourt pour son aide dans l’identification structurale des molécules, à Frédéric Borlat pour son assistance et Nathalie pour son aide administrative. J’adresse également mes remerciements à tous mes nouveaux amis genevois pour leur soutien : Hugo, Robin, Alice, Luis, Arnaud, Leonardo, Léonie, Pierre-Marie, Adriano, Angelica, Ozlem, Noémie, Aymeric, Davide, Carlotta, Sara et Rebecca. Merci au Dr. Jean-Jacques Filippi pour son encadrement pendant mes stages de Master 1 et 2, qui m’a permis de découvrir et d’apprécier la chimie des substances naturelles ; merci au Dr. Loic Tissandié pour son aide et son soutien. Je vous souhaite une bonne continuation ! Que seraient mes remerciements sans penser à tous mes amis compatriotes de Corse : Johanna, Camille, Julie et Anaïs qui me suivent et me soutiennent maintenant depuis 10 ans ; ma seconde petite famille : Stefano, Maria, Marie, Alicia, Julie, Andrea et notre nouveau membre Marc’Andria ! On n’oubliera jamais toutes nos aventures et ce beau confinement de l’enfer dans la House. A Roberto, mon meilleur ami d’enfance ; à Adrien, mon ami et grand rival de la Licence 1 à Corte jusqu’au Master 2 à Nice ainsi que sa copine Emilie ; à Ange- François, mon grand ami de Corte ; à Gabriel, mon ami et confident ; à Alexis, mon ami compatriote et une pensée à mes amis Lucia, Maria et Christophe. Pour finir, je souhaite remercier ma famille pour leur soutien, ma Maman qui a toujours été à mes côtés et qui a toujours fait passer les besoins de ses enfants avant les siens, ma sœur Stella ma fière complice, ma grand-mère Marie-Madeleine et mon grand-père Antoine, mon frère Fabien et ma belle-sœur Line, mes nièces Ava et Blanche, mes oncles et tantes, mes cousines Marie, Andrea et Lara, mon cousin Ludovic et le reste de ma famille. Enfin, je voudrais remercier infiniment l’homme, sans qui je ne serai pas où j’en suis aujourd’hui, mon héros, mon Papa. Ses sacrifices, son soutien et sa force m’ont permis d’être la personne que je suis aujourd’hui. Je continuerai de tracer mon chemin pour devenir le même homme que l’exemple qu’il m’a laissé. Je suis fier d’être ton fils. Tu me manques. Je t’aime. 3 4 Table des matières Remerciements ...................................................................................................................................... 2 Liste des abréviations ........................................................................................................................... 9 Liste des figures .................................................................................................................................. 12 Liste des tableaux ............................................................................................................................... 15 Liste des schémas ............................................................................................................................... 16 Liste des Annexes ............................................................................................................................... 17 Liste des molecules citées .................................................................................................................. 22 CHAPITRE 1 : Introduction Générale ............................................................................................. 41 CHAPITRE 2 : Classes de molécules naturelles ............................................................................. 51 2.1. Les métabolites primaires ...................................................................................................... 52 2.2. Les métabolites secondaires .................................................................................................. 52 2.2.1. Les terpènes et dérivés ................................................................................................... 53 2.2.2. Les polyphénols .............................................................................................................. 54 2.2.3. Les alcaloïdes .................................................................................................................. 55 CHAPITRE 3 : La médecine traditionnelle dans le monde .......................................................... 57 3.1. Médecine traditionnelle africaine ......................................................................................... 58 3.2. Médecine traditionnelle en Amérique ................................................................................. 59 3.3. Médecine Ayurvédique ........................................................................................................
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