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Structural Elucidation of Secondary Metabolites from Hypoxylon Fragiforme, Using High Resolution Mass Spectrometry and Gas-Phase Ion-Molecule Reactions Ljubica Svilar

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Structural Elucidation of Secondary Metabolites from Hypoxylon Fragiforme, Using High Resolution Mass Spectrometry and Gas-Phase Ion-Molecule Reactions Ljubica Svilar Structural elucidation of secondary metabolites from Hypoxylon fragiforme, using high resolution mass spectrometry and gas-phase ion-molecule reactions Ljubica Svilar To cite this version: Ljubica Svilar. Structural elucidation of secondary metabolites from Hypoxylon fragiforme, using high resolution mass spectrometry and gas-phase ion-molecule reactions. Biochemistry [q-bio.BM]. Université Pierre et Marie Curie - Paris VI, 2012. English. NNT : 2012PAO66468. tel-00836214 HAL Id: tel-00836214 https://tel.archives-ouvertes.fr/tel-00836214 Submitted on 20 Jun 2013 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. THESE DE DOCTORAT DE L’UNIVERSITE PIERRE ET MARIE CURIE et UNIVERSITE DE NIS Spécialité Systems Bioorganique / Spectrochimie Ecole doctorale de Chimie Moleculaire (ED 406) Présenté par Ljubica SVILAR Pour obtenir le grade de DOCTEUR de l’UNIVERSITÉ PIERRE ET MARIE CURIE Structural elucidation of secondary metabolites from Hypoxylon fragiforme, using high resolution mass spectrometry and gas-phase ion-molecule reactions soutenue le 11 Octobre 2012 devant le jury composé de : Directeurs de thèse M. Jean-Claude TABET Mme. Vesna STANKOV-JOVANOVIC Rapporteurs : M. David RONDEAU Mme. Estelle PARIS Examinateurs: Mme. Gordana STOJANOVIC M. Christophe JUNOT M. Louis FENSTERBANK Title: Structural elucidation of secondary metabolites from Hypoxylon fragiforme, using high resolution mass spectrometry and gas-phase ion-molecule reactions SUMMARY Fungi produce a wide variety of biologically active compounds/metabolites that could be used for medicinal and pharmaceutical purposes. Mitorubrines, members of the family of azaphilones, constitute a particularly interesting set of structurally diverse secondary metabolites, exhibiting a wide range of biological activities (e.g. antimicrobial, antibacterial, antimalarial). This work describes the development of several mass spectrometry-based approaches to solve the natural structural diversity and complexity of azaphilones extracted from Hypoxylon fragiforme fungus. The first part of this manuscript is dedicated to the development and validation of an analytical methodology involving liquid chromatography coupled to high resolution mass spectrometry for the efficient and accurate detection of trace-level azaphilones in complex fungal extracts. Further collision-induced dissociation and hydrogen/deuterium exchange experiments were performed to fully elucidate and characterize the azaphilones and their nitrogenized analogues from Hypoxylon fragiforme. The second part is devoted to the application of these different analytical strategies to the in-depth characterization of a novel family of secondary metabolites derived from azaphilones, the mitorubramines. Lastly, these different secondary metabolites were further purified to confirm their chemical structures by NMR spectroscopy. Keywords: Azaphilone; mitorubramines; Hypoxylon fragiforme; LC-ESI-MS; LTQ- Orbitrap; MSn; triple quadripole; gas-phase H/D exchange. 3 Titre : Elucidation de la structure des métabolites secondaires d’Hypoxylon fragiforme par spectrométrie de masse haute résolution et réactions ions-molécules en phase gazeuse RESUME Les champignons produisent une grande variété de composés/métabolites biologiquement actifs qui peuvent être utilisés à des fins médicinales et pharmaceutiques. Les mitorubrines, membres de la famille des azaphilones, constituent un ensemble particulièrement intéressant de métabolites secondaires, présentant une grande étendue d’activités biologiques (e.g. antimicrobienne, antibactérienne, antipaludique). Ce travail présente le développement de plusieurs approches de spectrométrie de masse permettant de résoudre la diversité structurelle naturelle et la complexité des azaphilones extraits des champignons Hypoxylon fragiforme. La première partie de ce manuscrit est dédiée au développement et à la validation d’une méthodologie analytique impliquant la chromatographie liquide couplée à la spectrométrie de masse haute résolution pour la détection efficace et précise de traces d’azaphilones dans des extraits fongiques complexes. En outre, des expériences de spectrométrie de masse en mode tandem (par dissociation induite par collision, CID) et d'échange hydrogène/deutérium ont été effectuées pour élucider et caractériser les azaphilones et leurs analogues azotés chez Hypoxylon fragiforme. La deuxième partie est consacrée à l'application de ces différentes stratégies analytiques pour la caractérisation approfondie d'une nouvelle famille de métabolites secondaires dérivés des azaphilones, les mitorubramines. Enfin, ces différents métabolites secondaires ont été purifiés pour confirmer leur structure chimique par spectroscopie RMN. Mots-clés : Azaphilone; mitorubramines; Hypoxylon fragiforme; LC-ESI-MS; LTQ- Orbitrap; MSn; triple quadripole; échanges H/D en phase gazeuse. 4 To the Universe Acknowledgments First and foremost I thank my mentors Prof. Dr. Jean-Claude Tabet and Dr. Vesna Stankov- Jovanovic for their guidance and support of my work in their laboratories in France and Serbia. I took advantage of the occasion they gave me to work under their supervision, to learn a great amount during this time. I enjoyed the stimulating and pleasant atmosphere in their research groups in France and Serbia. I thank to French Government for its financial support during my sojourn in France and for all benefits I had with that scholarship. I wish to express my great gratitude to Dr. Estelle Paris and Prof. Dr. David Rondeau for accepting to judge this work as referees. I would also like to thank Prof. Dr. Gordana Stojanovic, Dr. Christophe Junot and Dr. Louis Fensterbank for their participation as the exam committee. I wish to thank all the people with whom I have worked and contributed to the development of this work. Great thanks to Danis Lesage for long discussions on the gas-phase reactions and for its support, availability and ingenious suggestions. I want to thank to Heloise Dossmann for having achieved the theoretical calculations. Her participation was one of the essentials for clarification of misunderstandings we have met during this work. I am particularly grateful to Hristo Nedev giving me many answers on many questions concerning orbitrap mass spectrometer, as well as for the help for making preparative HPLC working properly. I want to thank him for having been always available to answer my questions. Furthermore, I want to thank him for being a real friend during these years spent in UPMC, for making a lot of jokes, for teaching me French language and for reminding me every day on my fatherland. I thank the NMR team of the Institut Parisienne de Chimie Moleculaire for the measurement of NMR spectra. I wish to acknowledge the contribution of Elsa Caytan in offering valuable interpretation and carrying out of important NMR spectra. Thanks to my workmates from Jussieu: Adrian, Bessem, Farid, Xiaohua, Viet, Baiyi, Vera, Chafia, Ludo. They were real friends; I will never forget their support and jokes and lunches at Chinese restaurants! Thanks to my workmate from Serbia, Marija Ilic for good times spent in the lab and for the great team works we did together. Thanks to Jérôme for supporting my bad moments, but thanks even more for passing a positive moments with me. Thanks to my sisters for being always there for encouraging me. I want to thank to Natali as well for being as a sister to me during this four years spent in France, and for listening all of my doubts and excitements. The most I want to thank to my Master Mind group, Branka, Ivana, Miso for making me a better person from day to day. I am finally indebted to my mom who gave all her best for my education. 9 Table of content SUMMARY ....................................................................................................................................... 3 RESUME ........................................................................................................................................... 4 Acknowledgments ............................................................................................................................. 9 Table of content ............................................................................................................................... 11 List of Figures .................................................................................................................................. 15 List of Tables ................................................................................................................................... 19 List of abbreviations ....................................................................................................................... 21 Preface ................................................................................................ 25 General part ...................................................................................... 29 1. Natural products ...................................................................................................................
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