Thi Thu Tram NGUYEN

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Thi Thu Tram NGUYEN ANNÉE 2014 THÈSE / UNIVERSITÉ DE RENNES 1 sous le sceau de l’Université Européenne de Bretagne pour le grade de DOCTEUR DE L’UNIVERSITÉ DE RENNES 1 Mention : Chimie Ecole doctorale Sciences De La Matière Thi Thu Tram NGUYEN Préparée dans l’unité de recherche UMR CNRS 6226 Equipe PNSCM (Produits Naturels Synthèses Chimie Médicinale) (Faculté de Pharmacie, Université de Rennes 1) Screening of Thèse soutenue à Rennes le 19 décembre 2014 mycosporine-like devant le jury composé de : compounds in the Marie-Dominique GALIBERT Professeur à l’Université de Rennes 1 / Examinateur Dermatocarpon genus. Holger THÜS Conservateur au Natural History Museum Londres / Phytochemical study Rapporteur Erwan AR GALL of the lichen Maître de conférences à l’Université de Bretagne Occidentale / Rapporteur Dermatocarpon luridum Kim Phi Phung NGUYEN Professeur à l’Université des sciences naturelles (With.) J.R. Laundon. d’Hô-Chi-Minh-Ville Vietnam / Examinateur Marylène CHOLLET-KRUGLER Maître de conférences à l’Université de Rennes1 / Co-directeur de thèse Joël BOUSTIE Professeur à l’Université de Rennes 1 / Directeur de thèse Remerciements En premier lieu, je tiens à remercier Monsieur le Dr Holger Thüs et Monsieur le Dr Erwan Ar Gall d’avoir accepté d’être les rapporteurs de mon manuscrit, ainsi que Madame la Professeure Marie-Dominique Galibert d’avoir accepté de participer à ce jury de thèse. J’exprime toute ma gratitude au Dr Marylène Chollet-Krugler pour avoir guidé mes pas dès les premiers jours et tout au long de ces trois années. Je la remercie particulièrement pour sa disponibilité et sa grande gentillesse, son écoute et sa patience. Sa parfaite maîtrise scientifique et ses idées qui m’ont si souvent sortie de l’embarras et parfois des impasses. Je remercie très sincèrement le Professeur Joël Boustie, mon directeur de thèse, de m’avoir accueillie dans son laboratoire et de m’avoir permis d’accéder à l’univers passionnant de la chimie des lichens. Je lui suis reconnaissante de m’avoir laissée une grande liberté afin que je puisse développer mes propres idées au cours de cette thèse. Je le remercie vivement de sa disponibilité et de sa rigueur scientifique qui m'ont permis de travailler dans les meilleures conditions. Je remercie chaleureusement Madame la Professeure Kim Phi Phung Nguyen, qui a été ma directrice de master recherche au Vietnam. C’est auprès d’elle que j’ai acquis mes premières connaissances en chimie des produits naturels et en chimie moléculaire. C’est également grâce à son aide que j’ai pu rencontrer le Professeur Joël Boustie. Je tiens également à exprimer ma gratitude à l’ensemble de l’équipe qui m’a soutenue ces trois années, pour leurs conseils avisés, leurs remarques pertinentes, leur écoute, leur aide et leur gentillesse. Ils ont fait de ce travail le fruit d’une véritable réflexion collective. Je voudrais adresser plus particulièrement tous mes remerciements à Françoise pour m’avoir guidée dans la réalisation des tests biologiques afin de valoriser les molécules que j'avais isolées. Merci à Aurélie de m’avoir expliqué le fonctionnement des appareillages les premiers jours et de m’avoir procuré les produits chimiques dont j’avais besoin. Isabelle et Solenn, merci pour votre aide dans la réalisation des tests biologiques. Merci à Sophie et à Béatrice pour vos relectures. Merci à Audrey de m’avoir donné l’accès aux herbiers (H. des Abbayes et L. J-C. Massé). Anne-Cécile, Claudia, David, Maryse, Marie-Laurence, Patricia, Philippe, Pierre, i Michèle, Gilles, Nicolas, Jacques, Myriam, Mickaël, Jeff, Jean-Charles un grand merci à tous d’avoir été là pour moi. J’adresse mes remerciements sincères à Monsieur Jean-Yves Monnat, Biologiste à l’Université de Bretagne Occidentale (Brest, France) pour m’avoir aidée à collecter et identifier les lichens. Je remercie également les autres membres de l’Association Française de Lichénologie pour m’avoir fourni des échantillons de Dermatocarpon. Je remercie Isabelle Gallais et le Pr. Odile Sergent (UMR Inserm 1085, IRSET, Université de Rennes 1) pour la réalisation des tests antioxydants portant sur la peroxydation lipidique. Je tiens également à exprimer ma reconnaissance à tout le personnel du CRMPO pour les analyses de masse effectuées sur les produits que j'avais isolées. Merci à tous les étudiants et post-doctorants pour les discussions et les agréables moments: Pierre, Delphine, Nathalie, Friardi, Maïwenn, Sarah Komaty et Vianney. Je remercie tous mes amis vietnamiens, surtout Binh, Duy, Linh, Tu, Hung, Huyen et Ha, qui ont partagé ma vie au quotidien pendant mon séjour en France. Un grand merci à Tam pour ton aide sur les analyses statistiques. J’exprime toute ma gratitude envers le Gouvernement vietnamien pour l'attribution de la bourse qui m’a permis de mener cette thèse. Je remercie également le laboratoire du professeur Joël Boustie pour le complément de financement qui a permis la réalisation de ce travail en France. Je remercie du fond du cœur ma famille pour leurs encouragements et leur soutien au quotidien. Merci à mes parents qui ont tant fait pour moi. Merci à mon frère aîné et à ma sœur pour notre complicité. J’ai une pensée toute particulière pour mon petit garçon Khanh, qui m’a fait sourire dans les moments difficiles; à ma belle-sœur Thuy qui m’a aidée dans les démarches administratives surtout quand c’était en français; à mon mari Thien pour ses encouragements, son dévouement auprès de notre fils pendant mon absence et son amour inconditionnel. Enfin merci à tous ceux qui liront cette thèse pour l’intérêt qu’ils porteront à mon travail… ii Table of Contents Remerciements .......................................................................................................................... i Table of Contents ................................................................................................................... iii List of abbreviations .............................................................................................................. vii List of Tables ........................................................................................................................... ix List of Figures.......................................................................................................................... xi Résumé en français ................................................................................................................ xv Introduction .............................................................................................................................. 1 CHAPTER 1: LICHENS AND PHOTOPROTECTION ..................................................... 3 1 Presentation of lichens ...................................................................................................5 1.1 Definition ................................................................................................................5 1.2 Thallus morphology and anatomy ...........................................................................5 1.3 Symbiosis .................................................................................................................8 1.4 Chemical compounds ...............................................................................................9 2 Photoprotective responses of lichens ...........................................................................11 2.1 Harmful effects of UV radiation ............................................................................11 2.2 Photoprotective mechanisms ..................................................................................12 2.2.1 Screening mechanism ................................................................................13 2.2.2 Quenching mechanism ..............................................................................13 2.2.3 Repair mechanism .....................................................................................15 2.3 Chemical features of UV absorbing compounds ...................................................15 3 Mycosporines and MAAs – natural photoprotectants ..................................................18 3.1 History ....................................................................................................................18 3.2 Characteristics ........................................................................................................19 3.3 Biosynthesis ...........................................................................................................22 3.4 Role of mycosporine-like compounds in nature ....................................................23 3.5 Mycosporine-like compounds in lichens ...............................................................24 CHAPTER 2: SCREENING AND QUANTIFICATION OF MYCOSPORINE-LIKE COMPOUNDS IN THE DERMATOCARPON GENUS ...................................... 29 Purpose of this study .........................................................................................................31 1 Screening of mycosporine-like compounds .................................................................33 1.1 Materials and methods ...........................................................................................33 1.1.1 Lichen material ..........................................................................................33 1.1.2 Extraction and purification of mycosporine-like compounds ...................40 1.1.3 HPTLC-UV spectrophotodensitometry and HPLC-DAD-MS analysis ....42 1.1.4 Esterification conditions of mycosporine
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