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Université Bordeaux Segalen Année 2012 Thèse no 2006 THÈSE pour le DOCTORAT DE L’UNIVERSITÉ BORDEAUX 2 Mention : Sciences, Technologie, Santé Option : Interface Chimie-Biologie Présentée et soutenue publiquement Le 20 décembre 2012 Par Jonathan BISSON Né le 26 Mars 1985 à Bruges (France, 33) DÉVELOPPEMENTS MÉTHODOLOGIQUES EN CHROMATOGRAPHIE DE PARTAGE CENTRIFUGE APPLICATION AUX STILBÉNOÏDES Membres du jury Mme. Françoise Guéritte, Directrice de recherche INSERM-CNRS, ICSN, Gif-sur-Yvette Présidente M. Alain Berthod, Professeur à l’Université de Lyon Rapporteur M. Marcel Hibert, Professeur à l’Université de Strasbourg Rapporteur M. Philippe Jeandet, Professeur à l’Université de Reims Examinateur M. Patrice André, Responsable, GIE LVMH Recherche Personnel extérieur M. Jean-Michel Mérillon, Professeur à l’Université de Bordeaux Examinateur M. Pierre Waffo-Téguo, Maître de conférences à l’Université de Bordeaux Directeur de thèse Résumé Les stilbénoïdes, sont des composés phénoliques majoritairement issus du règne vé- gétal. La Vigne par l’intermédiaire du vin et du raisin est la principale source alimen- taire de stilbènes. La mise en évidence de leur rôle dans les mécanismes de défense des plantes et leurs activités biologiques, y compris sur l’Homme, en font un sujet d’étude en plein essor. L’un des objectifs de cette thèse a été de développer un ensemble destra- tégies à la fois analytiques et préparatives utilisant la Chromatographie de Partage Cen- trifuge (CPC) pour l’étude et l’obtention de ces molécules. Dans un premier temps, nous avons développé une approche de couplage entre cette technique et un spectromètre à Résonance Magnétique Nucléaire (RMN) par l’intermédiaire d’un système d’Extraction sur Phase Solide automatisé (EPS). Dans un second temps, nous avons mis au point un ensemble de méthodes et d’approches séparatives permettant d’obtenir ces com- posés. Nous avons, grâce au développement d’une méthodologie de dosage de solvants par spectrométrie RMN, étudié une gamme dérivée d’une gamme très utilisée en CPC, l’ARIZONA. Nous avons montré que ces systèmes dérivés, peuvent être utilisés au tra- vers de stratégies d’élution telles que des pas et des gradients afin d’optimiser les sépa- rations. L’une des finalités de notre travail est d’offrir des méthodes permettant d’obte- nir ces composés dans des quantités et des qualités suffisantes pour pouvoir constituer une chimiothèque interne au laboratoire pouvant prétendre à s’intégrer dans la Chi- miothèque Nationale. Une dernière partie fait état du développement d’outils informa- tiques, dont la création d’une base de donnée Libre pour les chercheurs en Substances Naturelles. Mots-clés : Stilbénoïdes, Vitis vinifera, CPC, RMN, EPS, Couplages, Gradients b Abstract Stilbenoids are phenolic compounds mostly found in the vegetable kingdom. Vine through wine and grape is the main source of stilbenes in the human diet. The involvement of these compounds in plants resistance mechanisms and their diverse biological activi- ties, including on the human health are continuously highlighted. Making this topic a fast-growing one. One of the objectives of this thesis has been to develop a whole set of analytical and preparative strategies using Centrifugal Partition Chromatography (CPC) in order to study and obtain these molecules. Over a first phase, we developed a hyphenated approach between this technique and Nuclear Magnetic Resonance (NMR) through an automated Solid Phase Extraction (SPE) system. Then, we developed a set of separative methods and approaches with the aim of obtaining these compounds. Then, we carried out the development of a solvent quantifications methodology using NMR spectrometry. This allowed us to study a spin-off scale of a widely-used solvent systems collection called ARIZONA. We showed that these systems are good candidates for different elution strategies using steps and gradients with the aim to optimize separa- tions. One of our purpose was to provide methods for effective and efficient purification of these compounds. This would allow, together with a lab-scale compounds library, their integration into the Chimiothèque Nationale, a nationwide chemical library. Last part accounts for computer tools development, including the creation of a Free data- base system for Natural Substances researcher. Keywords : Stilbenoids, Vitis vinifera, CPC, NMR, SPE, Hyphenation, Gradients c Remerciements Cette thèse n’aurait pu avoir lieu sans un nombre incalculable de personnes. Àcom- mencer par le directeur du GESVAB, le Professeur Jean-Michel Mérillon, et mon di- recteur de thèse le Docteur Pierre Waffo-Téguo. Je tiens à les remercier pour l’enca- drement, la très forte confiance qu’ils m’ont accordé, même quand il fallait mettre les mains dans les machines, les discussions, les échanges d’expériences. Merci Pierre pour ta disponibilité, que ce soit pour discuter de la thèse, de science ou d’autres choses et pour la confiance et les libertés que tu m’as laissées. Je tiens à remercier le Docteur Françoise Guéritte, pour avoir accepté de présider le jury, mais aussi pour son accueil chaleureux et les nombreuses discussions lors de mon stage de Master 2. J’ai été initié à la Phytochimie, domaine à l’époque tout nouveau pour moi, au sein de son équipe. Et plus particulièrement avec l’encadrement du Docteur Vincent Dumontet et d’Anne-Laure Simonin, mais je n’oublie pas tous les autres qui ont participé aussi, Marc, Barbara, Jean-François, Marie-Thérèse, Nicolas, Guillaume, Aurélie, Mélanie, Mialy… Ainsi que Pierre-Marie et Mehdi, dont j’ai beaucoup apprécié et apprécie encore d’être si proche. Merci à Alain Berthod, rapporteur de ce travail et spécialiste de la Chromatographie de Partage Centrifuge, dont les travaux ont inspiré une partie de ces recherches. Je re- mercie aussi Marcel Hibert, lui aussi rapporteur de ce travail, ses remarques très perti- nentes, ses travaux et ses réalisations ont été pour moi une grande source d’inspiration. Merci à Philippe Jeandet et Patrice André pour avoir accepté de participer à ce jury, et avoir apporté leurs visions de leurs domaines respectifs, à savoir la science de la vigne et du vin et l’ethnobotanique à visée industrielle. Ces travaux n’auraient pas pu voir le jour sans la participation des autres membres du GESVAB. Avec un remerciement tout particulier allant à Gérard Fondeville, Antonio Palos-Pinto, Marie-Laure Iglesias, Éric Pédrot, Martine Naud et Antonio Gomez-Garcia d pour leur soutien technique et moral. Au Docteur Alain Badoc, pour les nombreuses discussions et invitations à des activités en lien avec la botanique. Aux chercheurs per- manents ou non, les Docteurs Stéphanie Cluzet, Alain Decendit, Jean-Claude Delaunay, Stéphanie Krisa, Céline Rivière, Céline Valadeau (aussi pour son grand soutien et les discussions sur l’ethno pendant les pauses !), Jean-Pierre Monti, Tristan Richard, Gré- gory Da Costa. Tous les membres passés et présents de la cellule, Pascal Poupard, Élo- die Renouf, Caroline Henry-Vitrac, Xavier Vitrac, Nadège Télef. À tous les doctorants, Carole Lambert, Merian Nassra, Yorgos Papastamoulis, Kamel Arraki, Jean-Baptiste Guyon, Stéphanie Dudonné. Les stagiaires et visiteurs Marie-Pierre Gaultier, Sylvia Lucas, Koovendren Ruthnum, Hilaire Kouakou, Yapo, Hamza Temsamani, Alexander Acevedo, Éva Gatineau, Holmi Khayati, Blandine Madji Hounoum, Frédérique Andrieu, Ainura Chodoeva. Et des remerciements tout particuliers aux Docteurs Alison Pawlus et Jonah Shaver pour toute leur aide ici et ailleurs et qui mériterait un chapitre entier. Un grand merci à tous les autres de l’ISVV, que ce soit au niveau de la recherche ou de l’administration : Alexandre Pons, Philippe Darriet, Axel Marchal, Davide Slaghe- naufi, Soizic Lacampagne, Gérard Darné (pour nos longues discussions), Bernard Do- nèche, Christian Kappel, Raj, Serge Delrot, Bernard Donèche, Christine Marty, Olivier, Ghislaine Hilbert, David et Fatma Lecourieux, Christel Renaud, Gilles De Revel, Denis Dubourdieu, Pierre-Louis Teissedre, Cécile Thibon, Mickael Jourdes, Yann Maguirre, Blanche Masclef, Olivier, Judith. Les personnels de la bibliothèque : Christine Badoc- Moreno, Renaud Benech, Hervé Cazassus, Elen Kenamgueven… Et tout ceux que j’ai malheureusement oublié de citer. Un remerciements aux remarquables stagiaires : Marion Brunel, Caroline Böcker, Marie Fortin, Keshika Mahadeo et Ramla Sahli. Des remerciements à l’équipe de pharmacognosie Catherine Chèze et Tshilundu Mu- lamba, j’ai vraiment apprécié pouvoir travailler avec vous et m’initier à l’enseignement. Aux membres de l’AFERP et de l’association Lapervenchelif pour m’avoir accordé la bourse m’ayant permis de faire une conférence à New-York pour l’ICNPR 2012. À toi Anthony, qui nous a quitté brutalement. Pour tous nos échanges lors denos pauses, soirées, discussions de couloir, dégustations… Ta motivation et ta vision des choses et de la science en particulier restera une source d’inspiration pour moi. e À mes parents, ma soeur, mon frère, mes grands parents et toute ma famille qui m’a accompagné, inspiré, formé, aiguisé ma curiosité et eu confiance en mes choix… À la famille de Margaux. À tous mes amis, du fin fond du Médoc et d’au delà, Yohan, Anne et Didier (et l’équipe du Hellfest), Dan, Bertrand, Laurent, Marc, 2T, Nuts, Svet, Ned, JoPi, MyOliv et tous les autres. Aux membres des diverses associations qui m’ont accompagné en lien ou non avec cette thèse : 2D2B, Aquidoc, AFSEP Club Jeunes, SFE, LaBx, CCBX… Et en particulier les TROLLiens et encore plus particulièrement à Christophe et Céline, pour leur soutien et plus. À Mukti, Jaz, Apo, Salvador et RR® pour l’accompagnement (et le café). Et encore une fois tous ceux et celles que j’ai oubliés ! Mais surtout à Margaux, pour avoir supporté un doctorant pendant ses 3 années de thèse, je sais que ça n’a pas été facile tous les jours. Une thèse c’est long, surtout vers la fin… Table des matières Table des figures I Liste des tableaux IV Abréviations V Glossaire X I Introduction générale 1 II Notions générales 8 1 Stilbénoïdes 10 1.1 Description générale ...............................
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    Mass Spectrometry T ⁎ Raul F

    Food Control 108 (2020) 106821 Contents lists available at ScienceDirect Food Control journal homepage: www.elsevier.com/locate/foodcont A rapid quantification of stilbene content in wine by ultra-high pressure liquid chromatography – Mass spectrometry T ⁎ Raul F. Guerreroa, Josep Valls-Fonayetb, Tristan Richardb, , Emma Cantos-Villara a Instituto de Investigación y Formación Agraria y Pesquera (IFAPA), Centro Rancho de la Merced, Consejería de Agricultura, Pesca y Desarrollo Rural (CAPDA), Junta de Andalucía. Ctra. Trebujena, Km 2.1, 11471, Jerez de la Frontera, Spain b Univ. Bordeaux, ISVV, EA 4577, USC 1366 INRA, Unité de Recherche Œnologie, Molécules d’Intérêt Biologique, 210 chemin de Leysotte, F-33882, Villenave d'Ornon, France ARTICLE INFO ABSTRACT Keywords: Stilbenes are a family of bioactive phenolic compounds. Wine is one of the main sources of stilbenes in diet. Very Stilbene few studies have dealt with a detailed quantitative analysis of stilbenes in wine. Most methodologies reported Viniferin until now have been restricted to the analysis of few stilbenes such as resveratrol and piceid. In this study, a Wine method for the quantification of wine stilbenes has been developed and validated. The method was simple, fast Mass spectrometry and sensitive with LOD between 4 and 28 μg/L. Matrix effects were assessed, and the methodology was validated in terms of precision, accuracy, linearity and repetitiveness. The method was able to quantify, in less than 5 min, fifteen targeted stilbenes in wines including seven monomers, three dimers, one trimer, and four tetramers. The methodology was applied to white and red wines. E-piceid was the main stilbene in white wine (mean 155 μg/L).
  • SUPPORTING INFORMATION Natural Stilbenes: an Overview

    SUPPORTING INFORMATION Natural Stilbenes: an Overview

    Electronic supplementary information (ESI) for Natural Product Reports SUPPORTING INFORMATION Natural stilbenes: an overview Tao Shen, Xiao-Ning Wang and Hong-Xiang Lou* Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Shandong University, 44 West Wenhua Road, Jinan 250012, P. R. China. E-mail: [email protected]; Tel: +86-531-88382012; Fax: +86-531-88382019. The ‘Supporting Information’ is a supplementary material for the section ‘4 Distribution’ to illustrate the distribution and chemical structures of 400 new stilbenes isolated during the period of 1995 to 2008. The ‘Supporting Information’ was composed of ten parts: Table S1 Distribution of monomeric stilbenes isolated from 1995 to 2008 Table S2. Distribution of oligomeric stilbenes isolated from 1995 to 2008 Figure S1 Chemical structures of monomeric stilbenes (1-125) isolated from 1995 to 2008 Figure S2 Chemical structures of resveratrol oligomers (126-303) isolated from 1995 to 2008 Figure S3 Chemical structures of isorhapontigenin oligomers (304-325) isolated from 1995 to 2008 Figure S4 Chemical structures of piceatanol oligomers (326-335) isolated from 1995 to 2008 Figure S5 Chemical structures of oxyresveratrol oligomers (335-340) isolated from 1995 to 2008 Figure S6 Chemical structures of resveratrol and oxyresveratrol oligomers (341-354) isolated from 1995 to 2008 Figure S7 Chemical structures of miscellaneous oligomers (355-400) isolated from 1995 to 2008 Reference 1 Electronic supplementary information (ESI) for Natural Product Reports Table
  • Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots

    Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots

    molecules Article Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots Harri Latva-Mäenpää 1,2,* , Riziwanguli Wufu 1 , Daniel Mulat 1, Tytti Sarjala 3, Pekka Saranpää 3,* and Kristiina Wähälä 1,4,* 1 Department of Chemistry, University of Helsinki, P.O. Box 55, FI-00014 Helsinki, Finland; riziwanguli.wufu@helsinki.fi (R.W.); [email protected] (D.M.) 2 Foodwest, Kärryväylä 4, FI-60100 Seinäjoki, Finland 3 Natural Resources Institute Finland, Tietotie 2, FI-02150 Espoo, Finland; tytti.sarjala@luke.fi 4 Department of Biochemistry and Developmental Biology, University of Helsinki, P.O. Box 63, FI-00014 Helsinki, Finland * Correspondence: harri.latva-maenpaa@foodwest.fi (H.L.-M.); pekka.saranpaa@luke.fi (P.S.); kristiina.wahala@helsinki.fi (K.W.); Tel.: +358-50-4487502 (H.L.-M. & P.S. & K.W.) Abstract: Stilbenes or stilbenoids, major polyphenolic compounds of the bark of Norway spruce (Picea abies L. Karst), have potential future applications as drugs, preservatives and other functional ingredients due to their antioxidative, antibacterial and antifungal properties. Stilbenes are photosen- sitive and UV and fluorescent light induce trans to cis isomerisation via intramolecular cyclization. So far, the characterizations of possible new compounds derived from trans-stilbenes under UV light exposure have been mainly tentative based only on UV or MS spectra without utilizing more detailed structural spectroscopy techniques such as NMR. The objective of this work was to study the stability Citation: Latva-Mäenpää, H.; Wufu, of biologically interesting and readily available stilbenes such as astringin and isorhapontin and R.; Mulat, D.; Sarjala, T.; Saranpää, P.; their aglucones piceatannol and isorhapontigenin, which have not been studied previously.