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Lipopeptides from Cyanobacteria: Structure and Role in a Trophic Cascade

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Lipopeptides from Cyanobacteria: Structure and Role in a Trophic Cascade Lipopeptides from Cyanobacteria : structure and role in a trophic cascade Louis Bornancin To cite this version: Louis Bornancin. Lipopeptides from Cyanobacteria : structure and role in a trophic cascade. Other. Université Montpellier, 2016. English. NNT : 2016MONTT202. tel-02478948 HAL Id: tel-02478948 https://tel.archives-ouvertes.fr/tel-02478948 Submitted on 14 Feb 2020 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. Délivré par Université de Montpellier Préparée au sein de l’école doctorale Sciences Chimiques Balard Et de l’unité de recherche Centre de Recherche Insulaire et Observatoire de l’Environnement (USR CNRS-EPHE-UPVD 3278) Spécialité : Ingénierie des Biomolécules Présentée par Louis BORNANCIN Lipopeptides from Cyanobacteria : Structure and Role in a Trophic Cascade Soutenue le 11 octobre 2016 devant le jury composé de Monsieur Ali AL-MOURABIT, DR CNRS, Rapporteur Institut de Chimie des Substances Naturelles Monsieur Gérald CULIOLI, MCF, Rapporteur Université de Toulon Madame Martine HOSSAERT-MCKEY, DR CNRS, Examinatrice, Centre d’Écologie F onctionnelle et Évolutive Président du Jury EMENT Monsieur Philippe POTIN, DR CNRS, Examinateur Station Biologique de Roscoff Monsieur Thierry DURAND, DR CNRS, Examinateur Institut des Biomolécules Max Mousseron Madame Isabelle BONNARD, MCF, Co-encadrante Université de Perpignan via Domitia Monsieur Bernard BANAIGS, CR INSERM, Directeur de Thèse Université de Perpignan via Domitia Avant propos Ce mémoire de doctorat est rédigé en anglais sous forme de thèse sur publications, publications acceptée (chapitre 3), à soumettre (chapitres 2 et 4) ou en préparation (chapitre 5). De ce fait les parties “Matériel et Méthodes“ et les références bibliographiques sont associées à chaque chapitre. La thèse a été financée pour une durée de 3 ans par l’Université de Montpellier (contrat doctoral de l’école doctorale Sciences Chimiques Balard 459), avec les supports financiers des projets “L es peptides naturels modifiés : des composés bioactifs et des composés modèles“ (BQR UPVD 2014), “Cyanodiv“ (projet incitatif LabEx Corail 2015) et “Keymicals“ (projet incitatif LabEx Corail 2016). Le travail a été réalisé au sein du Laboratoire de Chimie des Biomolécules et de l’Environnement (LCBE, EA 4215, Université de Perpignan Via Domitia) puis au sein du CRIOBE (USR CNRS-EPHE-UPVD 3278) à partir de janvier 2014. Les analyses en spectrométrie de RMN ont été réalisées sur le plateau technique “Métabolites secondaires et xénobiotiques“ de la plateforme Bio2Mar et sur la plateforme Intégrée de Biologie Structurale (PIBS) au Centre de Biochimie Structurale à Montpellier, et les analyses en HPLC-UV-ELSD et LC-MSn sur le plateau technique “Métabolites second aires et xénobiotiques“ de la plateforme Bio2Mar. Les analyses HRMS ont été réalisées à l’Institut de Chimie de Nice (ICN) ainsi qu’à l’Institut Méditerranéen de Biodiversité et d’Écologie (IMBE). Les expériences d’écologie ont été réalisées à la station m arine du CRIOBE à Moorea (Polynésie Française) de février à avril 2015. Remerciements Cette thèse est le fruit de trois ans de recherche et de rencontres avec des personnes de différentes disciplines qui ont indéniablement contribué à enrichir et affiner ce projet. Je tiens tout d’abord à remercier Gerald Culioli, Ali Al -Mourabit, Martine Hossaert, Philippe Potin et Thierry Durand qui me font l’honneur de juger mon travail. Je remercie chaleureusement Isabelle Bonnard, qui a co-encadré cette thèse, pour ses compétences scientifiques et ses corrections avisées mais également pour sa disponibilité, son sens de l’humour et les bonbons à l’anis pendant la rédaction. Je tiens à exprimer mes plus vifs remerciements à Bernard Banaigs, mon directeur de th èse, pour ses compétences scientifiques et sa passion qu’il sait si bien transmettre, pour son ouverture d’esprit, sa disponibilité et également pour ses valeurs humaines qui ont contribué à rendre ces trois années de thèse agréables et épanouissantes. Comment ne pas remercier Suzanne Mills, le « quatrième mousquetaire », qui aurait pu être co-encadrante de cette thèse tant elle a apporté ses compétences en écologie et sa disponibilité. Je la remercie pour ses corrections, son énergie et sa bonne humeur perpétuelle ainsi que pour les « collectes » de cyanobactéries aux Tipaniers. Le CRIOBE m’a permis de rencontrer beaucoup de personnes et je voudrais remercier sincèrement l’équipe de chimie pour la convivialité et la bonne humeur qui règne au sein de ce laboratoire. Merci à Khoubaib Ben Haj Salah dit « Kouby » pour sa gentillesse à toute épreuve, Sana Romdhane pour avoir partager ces moments de doctorants et m’avoir appris quelques mots en Arabe, Bruno Viguier pour les soirées pizzas-LC-MS entre autres, Christophe Calveyrac pour ses conseils en microbiologie, Marie-Louise Brassier pour résoudre les casse-têtes administratifs ainsi qu’à Sanjit Das, Nathalie Tapissier, Nicolas Inguimbert, Cédric Bertrand, Marie Virginie Salvia, Jean François Cooper, Delphine Raviglione, Anne Witczak, les stagiaires Klervi Dalle, Thomas Lepretre et les autres. Je tiens à remercier les membres d’AKINAO et plus particulièrement Vanessa Andreu et Anaïs Amiot pour leur sympathie et pour avoir partagé des moments agréables au laboratoire et en dehors. Le CRIOBE, c’est également des biologistes et je souhaiterais notamment remercier tous les doctorants, dont beaucoup sont devenus des amis, pour leur solidarité à Moorea et à Perpignan, merci à Pierpaolo Brena dit « Pipou » pour tous les bons moments passés ensemble, Marc Besson pour avoir partagé le terrain et la cuisine du poisson, Miriam Reverter qui m’a prouvé que les catalans sympathiques existent, Antoine Puisay, Isis Guibert, Lauric Thiault, Ewen Morin ainsi que Julien Hirschinger qui a partagé ma chambre à Moorea, Ricardo Beldade pour sa gentillesse et son aide sur le terrain, Frédéric Bertucci et tous les autres membres et stagiaires du CRIOBE qui se reconnaîtront. Cette thèse a été l’occasion de collaborer avec différents laborato ires et je remercie particulièrement Olivier Thomas (actuellement à la NUI à Galway) de l’institut de chimie de Nice (ICN) et Stephane Greff de l’Institut Méditerranéen de Biodiversité et d’Écologie (IMBE) à Marseille pour la spectrométrie de masse à haute résolution ainsi que Christian Roumestand du Centre de Biochimie Structurale (CBS) à Montpellier pour la RMN. J’adresse toute ma gratitude aux membres du laboratoire Arago à Banyuls-sur-mer, en particulier à Raphaël Lami et Yoan Ferandin pour les tests d e quorum quenching ainsi qu’à Laurent Intertaglia pour la mise en culture des cyanobactéries. Je tiens à remercier Mayalen Zubia de l’Université de la Polynésie Française (UPF) et Mélanie Roué de l’Institut de Recherche pour le Développement (IRD) de Tahiti pour leur partage de connaissances sur les cyanobactéries ainsi que les chimistes de l'université de la Polynésie Française pour m’avoir laissé utiliser leur laboratoire durant quelques heures. Enfin, je souhaite remercier ma famille et plus particulièrement mes parents qui m’ont toujours soutenu moralement et financièrement dans tout ce que j’entreprenais, ma sœur et mon frère tout simplement pour être présents dans les bons comme dans les mauvais moments. Je remercie tendrement Mélodie pour son soutien et sa patience au quotidien mais résumer son apport dans ma vie me prendrait plus que quelques lignes. Aussi, je remercie tous mes amis qui me permettent de relativiser et de m’évader quand le besoin s’en fait… en somme. Table of contents List of Abbreviations List of Figures List of Tables Chapter 1. General Introduction ............................................................................... 1 References ................................................................................................................................ 5 Chapter 2. Chemical Mediation as a Structuring Element in Marine Gastropod Predator-Prey Interactions ................................................................................................ 9 Abstract ..................................................................................................................................... 9 2.1. Introduction ...................................................................................................................... 9 2.2. Gastropods capable of sequestering diet-derived chemicals .......................................... 11 2.2.1. Sequestration of diet-derived chemicals by sacoglossans ....................................... 11 2.2.2. Sequestration of diet-derived chemicals by nudibranchs ........................................ 16 2.2.3. Sequestration of diet-derived chemicals by anaspideans (sea hares) ..................... 23 2.2.4. Sequestration of diet-derived chemicals by other gastropods ................................ 29 2.3. General mechanism of diet-origin secondary metabolites processing ........................... 32 2.3.1. Mechanism of metabolism and excretion: phases I, II and III .................................. 32 2.3.2. Examples
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