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Acétogénines D'annonaceae Et Parkinsonismes Atypiques Acétogénines d’Annonaceae et parkinsonismes atypiques : de la biodisponibilité de l’annonacine à l’exposition alimentaire. Natacha Bonneau To cite this version: Natacha Bonneau. Acétogénines d’Annonaceae et parkinsonismes atypiques : de la biodisponibilité de l’annonacine à l’exposition alimentaire.. Chimie analytique. Université Paris-Saclay, 2015. Français. NNT : 2015SACLS271. tel-01459289 HAL Id: tel-01459289 https://tel.archives-ouvertes.fr/tel-01459289 Submitted on 7 Feb 2017 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. NNT : 2015SACLS271 THÈSE DE DOCTORAT DE L’UNIVERSITÉ PARIS-SACLAY PRÉPARÉE À L’UNIVERSITÉ PARIS-SUD ÉCOLE DOCTORALE n° 569 Innovation thérapeutique : du fondamental à l’appliqué Spécialité de doctorat : Chimie des substances naturelles par Natacha BONNEAU Acétogénines d’Annonaceae et parkinsonismes atypiques : de la biodisponibilité de l’annonacine à l’exposition alimentaire. Thèse présentée et soutenue à Châtenay-Malabry, le 18 décembre 2015 : Composition du jury : M. Robert Farinotti, Professeur, Université Paris-Saclay, Président M. Thierry Hennebelle, Professeur, Université Lille 2, Rapporteur Mme Christine Herrenknecht, Professeur, Université de Nantes, Rapporteur Mme Séverine Derbré, MCU, Université Angers, Examinateur M. David Touboul, Chargé de Recherche, ICSN CNRS, Examinateur M. Pierre Champy, Professeur, Université Paris-Saclay, Directeur de thèse “The best laid schemes, o’ Mice and Men Gang aft agley” Robert Burns, To a Mouse (1785) Je tiens à remercier les Professeurs Christine Herrenknecht, Thierry Hennebelle, et Robert Farinotti ainsi que les Docteurs Séverine Derbré et David Touboul d’avoir accepté d’évaluer ce travail. Je remercie le Ministère de l’enseignement supérieur et de la recherche pour le financement qui m’a été attribué. Je remercie le Docteur Bruno Figadère et le Professeur Erwan Poupon pour m’avoir accueillie au sein du laboratoire de pharmacognosie. Je remercie également le Docteur Alain Brunelle pour m’avoir accueillie au sein de l’équipe de spectrométrie de masse de l’Institut de Chimie des Substances Naturelles dans le cadre de la collaboration entre les deux laboratoires. Je remercie chaleureusement le Professeur Pierre Champy, mon directeur de thèse, pour m’avoir confiée ce projet, et pour m’en avoir beaucoup appris sur le sujet. Je souhaiterais remercier le Professeur Michel Lebœuf pour m’avoir permis d’assister aux réunions bibliographiques, ainsi que les Docteurs François Roblot, Christophe Fourneau et Laurent Evanno, pour leur partage des connaissances lors des enseignements de travaux pratiques. Je remercie mes collègues doctorants, anciens et nouveaux, pour les bons moments partagés. J’adresse mes remerciements les plus sincères à toutes les personnes qui ont contribué à ce projet : - au Docteur David Touboul et à Isabelle Schmitz-Afonso pour m’avoir formée et accompagnée tout au long de ce projet. - au Docteur Alexandre Maciuk pour l’acquisition du Q-TOF au sein du laboratoire. - à Karine Leblanc pour son aide lors des analyses LC-UV et MS. - à Jean Christophe Jullian et Camille Dejean, pour les analyses RMN. - aux Docteurs Paul Coulerie et Valérie Kiagy, de l’Institut d’Agronomie Néo-Calédonien pour nous avoir fourni des extraits de fruits, ainsi qu’à toutes les personnes qui ont collecté des fruits, en particulier Pr Guy Lewin, Dr Faustin Kabran, et Isabelle Cazin. - à Valérie Domergue et son équipe, pour m’avoir permis de réaliser les expérimentations animales dans de bonnes conditions, ainsi qu’à Audrey Valentin, Blandine Séon-Méniel, François Sénejoux, qui tous à un moment ont pris de leur temps pour m’aider lors des prélèvements. - à Alexandre Dubesset pour avoir isolé de l’annonacine lors de son stage de M1, et pour son implication dans les expérimentations animales. - à Lamia Baloul pour sa quantification de la squamocine pendant son stage de M2. - à Timothé Cynober pour avoir appliqué la quantification par 1H RMN à de nombreux extraits bruts pendant son stage de M1. - à Leïla Haddad, pour avoir réalisé des extraits pendant son stage de L3. Je remercie chaleureusement tous les membres du laboratoire de pharmacognosie et de l’équipe de spectrométrie de masse que j’ai eu l’occasion de côtoyer durant ces années. Mes remerciements plus particuliers vont, - à Marie et Hanane, pour votre enthousiasme. Cela a été un plaisir de travailler à vos côtés. - à Abha, en souvenir des rats. - à Alex, Inès et Grégoire. Parce que votre présence était essentielle. - à Adam, pour ton écoute et nos échanges toujours enrichissants. - à Pedro, pour nos très chouettes discussions. - à Mehdi, parce que tu m’as tellement appris. C’est toujours un plaisir de discuter avec toi. - à la Mehdi’s team, pour tous les bons moments de brainstorming. - aux Michels. Je vous aime tous toujours autant. - à Elise et Dalia, pour votre soutien, même de loin. - à Alice, Alice et Pauline pour vos encouragements et vos délicates attentions. - à Aurélie, pour ton incroyable soutien. Je te suis infiniment reconnaissante d’avoir été là cette année. - à Romain, pour avoir partagé ma vie pendant des années. Merci d’avoir été patient et de m’avoir soutenue dans tout ce que j’ai entrepris. - à mes frères. - à mes parents. SOMMAIRE Introduction générale..............................................................................5 Chapitre 1 : Annonaceae, acétogénines : données bibliographiques........9 1. Généralités sur le genre Annona ................................................................................................... 11 1.1. Classification, origine et répartition géographique .................................................................. 11 1.2. Description des espèces étudiées .......................................................................................... 12 1.3. Emplois et usages ................................................................................................................... 13 1.3.1. Culture et alimentation ..................................................................................................... 13 1.3.2. Médecine traditionnelle humaine et vétérinaire ............................................................... 14 1.3.3. Médecine traditionnelle Caribéenne ................................................................................ 15 1.3.4. Statut et emplois médicinaux en Occident ...................................................................... 16 1.4. Composition chimique du genre Annona ................................................................................ 17 2. Acétogénines d’Annonaceae ......................................................................................................... 19 2.1. Structure et classifications ...................................................................................................... 19 2.2. Répartition au sein des Annonaceae ...................................................................................... 22 2.3. Études qualitatives et quantitatives d’AAGs : travaux antérieurs ........................................... 25 2.3.1. Études qualitatives ........................................................................................................... 25 2.3.2. Études quantitatives sur acétogénines ............................................................................ 37 2.4. Mécanisme d’action et activités pharmacologiques ................................................................ 42 2.4.1. Inhibition du complexe I mitochondrial ............................................................................ 42 2.4.2. Relations structure-activité .............................................................................................. 44 2.4.3. Activités pharmacologiques et toxicité ............................................................................. 45 3. Acétogénines d’Annonaceae et parkinsonismes atypiques ........................................................... 49 3.1. Etudes épidémiologiques ........................................................................................................ 51 3.1.1. Les parkinsonismes atypiques Guadeloupéens .............................................................. 51 3.1.2. Autres cas de parkinsonismes atypiques « tropicaux » ................................................... 56 3.2. Discussion autour de l’implication des acétogénines ............................................................. 57 3.2.1. Au travers des études épidémiologiques ......................................................................... 57 3.2.2. Hypothèses étiologiques : molécules potentiellement impliquées .................................. 58 4. Étude ADME de l’annonacine : travaux antérieurs ........................................................................ 65 1 4.1. Absorption et distribution......................................................................................................... 65 4.2. Métabolisation de phase I ......................................................................................................
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