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Influence Des Phénomènes D'oxydation Lors De L'élaboration Des Moûts Sur La Qualité Aromatique Des Vins De Melon B. Et

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Influence Des Phénomènes D'oxydation Lors De L'élaboration Des Moûts Sur La Qualité Aromatique Des Vins De Melon B. Et CENTRE INTERNATIONAL D’ETUDES SUPERIEURES EN SCIENCES AGRONOMIQUES – MONTPELLIER SUPAGRO THESE Pour obtenir le grade de DOCTEUR DU CENTRE INTER NATIONAL D’ETUDES SUPERIEURES EN SCIENCES AGRONOMIQUES – MONTPELLIER SUPAGRO Ecole Doctorale : Sciences des Procédés – Sciences des Aliments Spécialité : Biochimie, Chimie, Technologie des Aliments Présentée et soutenue publiquement par Aurélie ROLAND Le 4 Novembre 2010 Influence des phénomènes d’oxydation lors de l’élaboration des moûts sur la qualité aromatique des vins de Melon B. et de Sauvignon Blanc en Val de Loire JURY Doris Rauhut Professeur, Forschungsanstalt Geisenheim, Fachgebiet Rapporteur Mikrobologie und Biochemie, Allemagne Juan Cacho Professeur, Universidad de Zaragoza, Departamento de Rapporteur Química Analítica, Espagne Eric Spinnler Professeur, AgroParisTech, Département Sciences et Examinateur Procédés des Aliments et Bioproduits, Grignon, France Florine Cavelier Directeur de Recherche CNRS, Institut des Biomolécules Examinateur Max Mousseron, Montpellier, France Frédéric Charrier Ingénieur Œnologue, Institut Français de la Vigne et du Vin, Membre Invité Pôle Val de Loire, Vertou, France Etienne Goulet Directeur Technique, Interloire, Angers, France Membre Invité Alain Razungles Professeur, Montpellier Supagro, UMR Sciences pour Directeur de Thèse l’œnologie , France Rémi Schneider Directeur UMT Qualinov, Institut Français de la Vigne et du Directeur de Thèse Vin, Pôle Rhône Méditerranée, Montpellier, France REMERCIEMENTS Ce travail de thèse a été réalisé au sein du Plateau Technique des Volatils à l’INRA de Montpellier dans le cadre d’un contrat CIFRE avec INTERLOIRE et en partenariat avec l’Institut Français de la Vigne et du Vin et la SICAVAC de Sancerre. En premier lieu, je souhaite remercier très sincèrement Rémi Schneider , mon directeur de thèse, pour avoir dirigé ce travail avec rigueur et enthousiasme, pour m’avoir encouragé e dans mes choix et fait confiance tout au long de ma thèse. Merci Rémi ! J’adresse également tous mes remerciements à Alain Razungles , mon directeur de thèse, pour son appui technique et personnel. Tous mes remerciements vont vers Florine Cavelier , mon coach en synthèse chimique, pour tous les conseils, les encouragements, l’enthousiasme et l’énergie dép ensés pour moi. Cela a été un véritable plaisir de travailler ensemble. Merci pour tout. Je remercie Doris Rauhut et Juan Cacho d’avoir accepté de juger mon travail de thèse. J’adresse également tous mes remerciements à Eric Spinnler , pour avoir accepté de présider ce jury de thèse. Je tiens également à remercier Etienne Goulet , directeur technique d’INTERLOIRE, pour m’avoir accueillie au sein de l’ interprofession des vins du Val de Loire. Ce projet a été initié par Michel Moutounet puis Raymond Baumes, je leur adresse mes sincères remerciements. Je remercie tout particulièrement Frédéric Charrier , Bertrand Daulny et Pascal Poupault pour leur appui technique, leurs encouragements et leur aide très précieuse lors de chaque vendange. Merci d’avoir pris le temps de m’expliquer les ficelles du métier. Je n’oublie pas non plus le personnel de l’IFV de Vertou et de la Sicavac de Sancerre qui m’ont toujours accueillie avec beaucoup de gentillesse et aidée dans mes expérimentations : Aurélie Pain (mille fois merci pour toutes tes contributions), Morvan Coarer (merci pour m’avoir secourue !), Alain Poulard , les 2 Yannick(s) , Marie Jaffre , Yann et Eric ainsi que tous les stagiaires. Ces trois années de thèse ont été ponctuées de divers comités dont je voudrais remercier les participants pour leur contribution scientifique et technique : Elodie Besseas , Thierry Dufourcq , Fabrice Doucet , Jean-Luc Le Quéré , Guy Albagnac et Hélène Fulcrand . J’adresse un remerciement tout particulier à Jean-Michel Salmon pour tous ses bons conseils et sa gentillesse. Remerciements 2 Je remercie la société Bucher Vaslin pour son appui technique lors des vendanges 2009 et plus particulièrement, Pascal Noilet et Luc Godart . Un grand merci à Jean-Marc pour l’analyse des AH, Clotilde et Jean Luc pour l’initiation au pelage des baies, Thérèse pour le glutathion, Christine pour les RMN et enfin Christian pour les fermentations. Durant ma thèse, j’ai eu la chance de travailler dans différents laboratoires : la Proteomics Core Facility à l’Ecole Polytech nique Fédérale de Lausanne et le Laboratoire de Protéomique Fonctionnelle dont je remercie l’ensemble du personnel pour leur accueil : Diego (merci pour tous tes conseils en LC-MS), Marc M. , Sandrine , Valérie(s) (les 2), Madeleine , Claude , Sylvain , Sonia , Marc T. , Thierry , Abasse, Jean-Benoît et Michel . Enfin, j’adresse avec beaucoup d’émotion tous mes remerciements à l’ensemble de l’équipe du PTV et de Nyséos. J’ai eu la chance de travailler avec vous pendant 3 ans et nous avons tellement partagé de choses ensemble. Un énorme merci à Jean-Paul (pour m’avoir accueillie da ns ton bureau et trouvé un super surnom…), Nicolas (merci pour tout), Peggy (merci pour tous tes bons conseils), Clément (spéciale dédicace entre IUTiens de Castres), Flo (énorme ton second prénom !), Laurent (merci pour tes fameuses daganettes). Je remercie également Jocelyne pour son aide très précieuse dans les méandres administratifs et toutes les personnes qui ont contribué à ce travail : Loïc , Stéphane , Virginie , Sandrine et Emilie . Ce travail n’aurait pas été possible sans le soutien quotidien de ma famille qui a toujours été là pour moi. Merci à mes parents , à mon frère Sébastien et à Laurent pour tous vos encouragements et vos marques d’affection. Enfin, et c’est le plus important , merci Jérôme pour ton soutien permanent et tout le bonheur que tu m’apportes. Je terminerai en dédiant ce manuscrit à la mémoire de ma marraine dont je garderai sa joie de vivre comme le plus beau des souvenirs. Remerciements 3 ABBREVIATIONS Les acronymes dédiés aux méthodologies analytiques sont utilisés dans ce manuscrit sous leur dénomination anglaise. 3MH 3-mercaptohexan-1-ol 3MHA Acétate de 3-mercaptohexyle 4MMP 4-mercapto-4-méthylpentan-2-one AAA Analyseur d’ Acides-Aminés Boc Tert -butyloxycarbonyl CCM Chromatographie sur Couche Mince Cys3MH S-3-(hexan-1-ol)-L-cystéine Cys4MMP S-4-(4-méthylpentan-2-one)-L-cystéine DBU 1,8-diazabicyclo-[5,4,0]-undec-7-ène DMS Diméthylsulfure DMSO Diméthylsulfoxide DTNB Acide 5,5'-dithio-bis(2-nitrobenzoïque) EDTA Acide éthylène-Diamine-Tétra Acétique EI-MS Electronic Impact - Mass Spectrometry Em Longueur d’onde d’émission eq équivalent ESI-MS Electrospray Ionization - Mass Spectrometry Ex Longueur d’onde d’excitation G3MH S-3-(hexan-1-ol)-glutathion G4MMP S-4-(4-méthylpentan-2-one)-glutathion GRP Grape Reaction Product GRP2 Acide di-glutathionyl-2,5-caféoyltartrique GSH Glutathion GSSG Glutathion oxydé GC-MS Gas Chromatography – Mass Spectrometry HPLC High Performance Liquid Chromatography HPLC-DAD High Performance Liquid Chromatography – Diode Array Detector HRMS High Resolution Mass Spectrometry IBMP 2-méthoxy-3-isobutylpyrazine LC-MS/MS Liquid Chromatography – tandem Mass Spectrometry LOD Limit of Detection LOQ Limit of Quantification LSA Levure Sèche Active MMB Monobromobimane MRM Multiple Reaction Monitoring OPA o-phtalaldéhyde PFBBr Bromure de 2,3,4,5,6-pentafluorobenzyle PPO Polyphénoloxydase QqQ Triple Quadripôle qsp Quantité suffisante pour Q-TRAP Quadripôle-Trappe Linéaire RMN Résonnance Magnétique Nucléaire rpm Rotation par minute RSD Relative Standard Deviation SIDA Stable Isotope Dilution Assay SIM Selected Ion Monitoring S/N Rapport Signal sur Bruit SRM Selected Reaction Monitoring T.A. Température Ambiante TES Triéthylsilane TFA Acide trifluoroacétique TMS Triméthylsilane TMSP Acide triméthylsilylpropionique TNB 2-nitro-5-thiobenzoate Abbréviations 4 AVANT PROPOS Les travaux de thèse présentés dans ce manuscrit ont été réalisés en partenariat avec Interloire (Bourse CIFRE) , l’Institut Français de la Vigne et du Vin, la Sicavac et l’INRA de Montpellier, au Plateau Technique des Volatils. La présentation de ce mémoire de thèse s’appuie sur les publications obtenues au cours de mes 3 années de recherche. Publications 1. Roland, A.; Schneider, R.; Le Guernevé, C.; Razungles, A.; Cavelier, F., Identification and quantification by LC-MS/MS of a new precursor of 3-mercaptohexan-1-ol (3MH) using stable isotope dilution assay: Elements for understanding the 3MH production in wine. Food Chem. 2010 , 121, 847-855. 2. Roland, A.; Vialaret, J.; Moniatte, M.; Rigou, P.; Razungles, A.; Schneider, R., Validation of a nano liquid chromatography-tandem mass spectrometry method for the identification and the accurate quantification by isotopic dilution of glutathionylated and cysteinylated precursors of 3-mercaptohexan-1-ol and 4-mercapto-4-methylpentan-2-one in white grape juices. J. Chromatogr. A 2010 , 1217, 1626-1635. 3. Roland, A.; Vialaret, J.; Razungles, A.; Rigou, P.; Schneider, R., Evolution of S-cysteinylated and S-glutathionylated thiol precursors during oxidation of Melon B. and Sauvignon blanc musts. J. Agric. Food Chem. 2010 , 58, (7), 4406-4413. 4. Roland, A.; Schneider, R.; Charrier, F.; Cavelier, F.; Rossignol, M.; Razungles, A., Distribution of varietal thiol precursors in the skin and the pulp of Melon B. and Sauvignon Blanc grapes. Food Chem. 2010, 125, 139 –144. 5. Roland, A.; Schneider, R.; Razungles, A.; Le Guernevé, C.; Cavelier, F., Straightforward synthesis of deuterated precursor to demonstrate the biogenesis of aromatic thiols in wine. J. Agric. Food Chem. 2010, 58, 10684 –10689. 6. Roland, A.; Schneider, R.; Razungles,
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