Les Composés Phénoliques De La Vigne

Total Page:16

File Type:pdf, Size:1020Kb

Les Composés Phénoliques De La Vigne Université Bordeaux Segalen Année 2011 Thèse n° 1910 THÈSE pour le DOCTORAT DE L’UNIVERSITÉ BORDEAUX 2 Mention : Sciences, Technologie, Santé Option : Oenologie Présentée et soutenue publiquement Le 15 décembre 2011 Par Carole LAMBERT Née le 18 octobre 1985 à Saint Jean d’Angély Étude du rôle des stilbènes dans les défenses de la vigne contre les maladies du bois Membres du Jury M. C. Bertsch, Professeur à l’Université de Haute-Alsace ..................... Président Mme. M. Adrian, Professeur à l’Université de Bourgogne .................... Rapporteur Mme. F. Fontaine, Maître de conférences à l’Université de Reims ........ Rapporteur Mme. S. Cluzet, Maître de conférences à l’Université Bordeaux 2 ....... Examinateur M. J.M. Mérillon, Professeur à l’Université de Bordeaux 2 ................... Directeur de thèse Remerciements Ce travail a été initié en 2008 au Groupe d’Etude des Substances Végétales à Activité Biologique. Je remercie ceux qui m’ont confié ce sujet et qui l’ont guidé : M. Jean-Michel Mérillon et Mme Stéphanie Cluzet. Je tiens, par ces quelques mots, à leur témoigner ma sincère reconnaissance pour leur disponibilité, leur investissement et leurs encouragements bienveillants. Mes remerciements vont également à l’ensemble des membres du jury pour leur collaboration à l’examen de ce travail et leur participation à la soutenance. Mesdames Marielle Adrian de l’Université de Bourgogne et Florence Fontaine de l’Université de Reims ont accepté d’être rapporteurs et Monsieur Christophe Bertsch de l’Université de Haute-Alsace a présidé ce jury. L’intérêt que vous avez porté à ce travail a permis une discussion enrichissante. Trouvez ici l’expression de ma profonde reconnaissance. Ce travail n’aurait pu se faire sans les collaborations établies au cours de cette thèse. Je remercie, Agnès Destrac-Irvine, Jean-Pascal Goutouly, Isabelle Merlin et Eric Gomes de l’UMR EGFV ainsi que Marie-France Corio-Costet, Gwenaëlle Comont, et Sébastien Gambier de l’UMR SAVE. Agnès, Jean-Pascal, je vous remercie d’avoir relu le manuscrit. Merci également aux membres du GESVAB qui se sont investi dans cette thèse : Tristan Richard, Pierre Waffo-Téguo, Jonathan Bisson et Yorgos Papastamoulis. Votre implication dans ce travail a été décisive. Jonathan, bonne chance pour la fin de ta thèse. Je remercie particulièrement Gérard Fondeville et Antonio Palos-Pinto pour leur aide et leur bonne humeur . Cette thèse est aussi le fruit du travail des étudiants qui ont effectué leur stage au GESVAB : Sabrina Dutrey, Vanessa Chadeffaud, Sylvia Lucas et Ian Li-Kim-Kiook. Merci pour votre implication et votre sympathie. Merci à tous les membres actuels et anciens du GESVAB. Au-delà de l’expérience professionnelle, ces trois années ont été humainement riche. Cela aura été un vrai plaisir de partager la vie quotidienne avec vous. J’espère retrouver cette ambiance de travail dans le futur. Je fais un clin d’œil particulier à Merian Nassra. Nous avons commencé ce dur labeur ensemble et partagé des moments de complicité : ta sagesse aura éclairé nos conversations. Je te souhaite bonne chance pour la fin de ta thèse et pour la suite. Merci à Nadège Telef-Micouleau et Stéphanie Krisa pour m’avoir initiée respectivement à la zumba et au théâtre et pour les échanges sympathiques qui ont jalonnés ces trois ans. Je remercie les membres du laboratoire de Biochimie du Raisin de la Faculté d’Œnologie de Bordeaux qui en premier m’ont formée à la recherche : Laurence Gény pour m’avoir accueillie dans le laboratoire et Annie l’Hyvernay pour m’avoir appris à « maniper ». Je remercie tout particulièrement Séverine Gagné et Soizic Lacampagne. Soizic, Séverine, merci infiniment pour votre soutien et votre amitié. Vous êtes des exemples pour moi et j’espère que l’avenir vous sourira à la mesure de vos talents de chercheur ! Je salue également tous les membres de l’ISVV que j’ai côtoyé pendant mes années d’étude. Je réserve mes derniers remerciements à mes proches. A mes amis, Sabrina, Frodo et leur petit Axel, Rémi, Marion, Laurent et Nathalie. A mes parents qui m’ont permis de faire ces études dans des conditions idéales et m’ont toujours écoutée et soutenue.Un remerciement particulier à papa pour ta passion pour les cours de botanique. A ma sœur, son mari et leur petit garçon pour avoir égayé ma thèse de moments de bonheur. A mes grand-parents, mon oncle et ma tante pour les instants partagés (le scrabble, les blagues, l’appel de la forêt, les papotages…). A mon Ludo, puisses-tu me supporter encore longtemps, merci pour notre vie à deux. Sommaire INTRODUCTION ...................................................................................................................... 1 CHAPITRE 1 : Étude bibliographique ....................................................................................... 5 I. La vigne, sensible aux maladies cryptogamiques ............................................................... 5 I.1. Les maladies du bois de la vigne ................................................................................. 7 I.1.1. L’importance des maladies du bois en France ..................................................... 7 I.1.2. L’eutypiose ........................................................................................................... 9 I.1.3. Le syndrome de l’esca ........................................................................................ 10 I.1.4. Le Black Dead Arm ............................................................................................ 16 I.1.5. Facteurs influençant l’expression des symptômes de maladie du bois .............. 18 I.1.1. Méthodes de lutte ............................................................................................... 20 II. Mécanismes de défense de la vigne face aux champignons ............................................. 22 II.1. Les défenses passives/constitutives ........................................................................... 22 II.2. Les défenses actives ................................................................................................... 23 II.2.1. Les récepteurs ..................................................................................................... 24 II.2.2. Les éliciteurs ...................................................................................................... 25 II.3. La signalisation cellulaire .......................................................................................... 28 II.4. Les réponses de défense induites ............................................................................... 29 II.4.1. La synthèse de protéines PR ............................................................................... 29 II.4.2. La synthèse de phytoalexines ............................................................................. 31 II.4.3. Le renforcement pariétal .................................................................................... 31 II.4.4. La réponse hypersensible ................................................................................... 32 II.5. La résistance systémique ........................................................................................... 33 II.5.1. La résistance systémique acquise ....................................................................... 33 II.5.2. La résistance systémique induite ........................................................................ 34 III. Les composés phénoliques de la vigne ............................................................................. 34 III.1. La biosynthèse des composés phénoliques ............................................................ 35 III.2. Les flavonoïdes ...................................................................................................... 37 III.2.1. Les anthocyanes .............................................................................................. 37 III.2.2. Les flavanols et les tanins ............................................................................... 38 III.2.3. Les flavonols ................................................................................................... 39 III.3. Les non flavonoïdes ............................................................................................... 40 III.3.1. Les acides phénols .......................................................................................... 40 III.3.2. Les stilbènes ................................................................................................... 41 III.4. Les stilbènes, phytoalexines de la vigne ................................................................ 44 III.4.1. Activité antifongique des stilbènes ................................................................. 44 III.4.2. Induction des stilbènes et résistance ............................................................... 45 III.4.3. Effet toxique des stilbènes : mode d’action .................................................... 46 III.4.4. Détoxification des stilbènes par les champignons .......................................... 47 IV. Mécanismes de défenses et maladies vasculaires : cas de la vigne .................................. 48 IV.1. Les mécanismes de défense dans le bois ............................................................... 48 IV.1.1. Le CODIT ....................................................................................................... 48 IV.1.2. Le modèle « zone de réaction » ...................................................................... 50 IV.1.3.
Recommended publications
  • Stilbenes: Chemistry and Pharmacological Properties
    1 Journal of Applied Pharmaceutical Research 2015, 3(4): 01-07 JOURNAL OF APPLIED PHARMACEUTICAL RESEARCH ISSN No. 2348 – 0335 www.japtronline.com STILBENES: CHEMISTRY AND PHARMACOLOGICAL PROPERTIES Chetana Roat*, Meenu Saraf Department of Microbiology & Biotechnology, University School of Sciences, Gujarat University, Ahmedabad, Gujarat 380009, India Article Information ABSTRACT: Medicinal plants are the most important source of life saving drugs for the Received: 21st September 2015 majority of the Worlds’ population. The compounds which synthesized in the plant from the Revised: 15th October 2015 secondary metabolisms are called secondary metabolites; exhibit a wide array of biological and Accepted: 29th October 2015 pharmacological properties. Stilbenes a small class of polyphenols, have recently gained the focus of a number of studies in medicine, chemistry as well as have emerged as promising Keywords molecules that potentially affect human health. Stilbenes are relatively simple compounds Stilbene; Chemistry; synthesized by plants and deriving from the phenyalanine/ polymalonate route, the last and key Structures; Biosynthesis pathway; enzyme of this pathway being stilbene synthase. Here, we review the biological significance of Pharmacological properties stilbenes in plants together with their biosynthesis pathway, its chemistry and its pharmacological significances. INTRODUCTION quantities are present in white and rosé wines, i.e. about a tenth Plants are source of several drugs of natural origin and hence of those of red wines. Among these phenolic compounds, are termed as the medicinal plants. These drugs are various trans-resveratrol, belonging to the stilbene family, is a major types of secondary metabolites produced by plants; several of active ingredient which can prevent or slow the progression of them are very important drugs.
    [Show full text]
  • Acuminatol and Other Antioxidative Resveratrol Oligomers from the Stem Bark of Shorea Acuminata
    Molecules 2012, 17, 9043-9055; doi:10.3390/molecules17089043 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Acuminatol and Other Antioxidative Resveratrol Oligomers from the Stem Bark of Shorea acuminata Norhayati Muhammad 1, Laily B. Din 1, Idin Sahidin 2, Siti Farah Hashim 3, Nazlina Ibrahim 3, Zuriati Zakaria 4 and Wan A. Yaacob 1,* 1 School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM Bangi 43600, Selangor D.E., Malaysia; E-Mails: [email protected] (N.M.); [email protected] (L.B.D.) 2 Faculty of Mathematics and Natural Sciences, Haluoleo University, Kendari 93232, Sulawesi Tenggara, Indonesia; E-Mail: [email protected] 3 School of Biosciences and Biotechnology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM Bangi 43600, Selangor D.E., Malaysia; E-Mails: [email protected] (S.F.H.); [email protected] (N.I.) 4 Malaysia-Japan International Institute of Technology, Universiti Teknologi Malaysia Kuala Lumpur, Jalan Semarak, Kuala Lumpur 54100, Malaysia; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +603-8921-5424; Fax: +603-8921-5410. Received: 1 June 2012; in revised form: 10 July 2012 / Accepted: 18 July 2012 / Published: 30 July 2012 Abstract: A new resveratrol dimer, acuminatol (1), was isolated along with five known compounds from the acetone extract of the stem bark of Shorea acuminata. Their structures and stereochemistry were determined by spectroscopic methods, which included the extensive use of 2D NMR techniques. All isolated compounds were evaluated for their antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity (RSA) and the β-carotene-linoleic acid (BCLA) assays, and compared with those of the standards of ascorbic acid (AscA) and butylated hydroxytoluene (BHT).
    [Show full text]
  • 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
    [Show full text]
  • WO 2018/002916 Al O
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2018/002916 Al 04 January 2018 (04.01.2018) W !P O PCT (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C08F2/32 (2006.01) C08J 9/00 (2006.01) kind of national protection available): AE, AG, AL, AM, C08G 18/08 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, (21) International Application Number: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, PCT/IL20 17/050706 HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, (22) International Filing Date: KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, 26 June 2017 (26.06.2017) MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (25) Filing Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 246468 26 June 2016 (26.06.2016) IL kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, (71) Applicant: TECHNION RESEARCH & DEVEL¬ UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, OPMENT FOUNDATION LIMITED [IL/IL]; Senate TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, House, Technion City, 3200004 Haifa (IL).
    [Show full text]
  • STILBENOID CHEMISTRY from WINE and the GENUS VITIS, a REVIEW Alison D
    06àutiliser-mérillonbis_05b-tomazic 27/06/12 21:23 Page57 STILBENOID CHEMISTRY FROM WINE AND THE GENUS VITIS, A REVIEW Alison D. PAWLUS, Pierre WAFFO-TÉGUO, Jonah SHAVER and Jean-Michel MÉRILLON* GESVAB (EA 3675), Université de Bordeaux, ISVV Bordeaux - Aquitaine, 210 chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon cedex, France Abstract Résumé Stilbenoids are of great interest on account of their many promising Les stilbénoïdes présentent un grand intérêt en raison de leurs nombreuses biological activities, especially in regards to prevention and potential activités biologiques prometteuses, en particulier dans la prévention et le treatment of many chronic diseases associated with aging. The simple traitement de diverses maladies chroniques liées au vieillissement. Le stilbenoid monomer, -resveratrol, has received the most attention due to -resvératrol, monomère stilbénique, a suscité beaucoup d'intérêt de par E E early and biological activities in anti-aging assays. Since ses activités biologiques et . Une des principales sources in vitro in vivo in vitro in vivo , primarily in the form of wine, is a major dietary source of alimentaires en stilbénoïdes est , principalement sous forme Vitis vinifera Vitis vinifera these compounds, there is a tremendous amount of research on resveratrol de vin. De nombreux travaux de recherche ont été menés sur le resvératrol in wine and grapes. Relatively few biological studies have been performed dans le vin et le raisin. À ce jour, relativement peu d'études ont été réalisées on other stilbenoids from , primarily due to the lack of commercial sur les stilbènes du genre autre que le resvératrol, principalement en Vitis Vitis sources of many of these compounds.
    [Show full text]
  • A Reference List of Phenolic Compounds (Including Stilbenes) in Grapevine (Vitis Vinifera L.) Roots, Woods, Canes, Stems, and Leaves
    antioxidants Review A Reference List of Phenolic Compounds (Including Stilbenes) in Grapevine (Vitis vinifera L.) Roots, Woods, Canes, Stems, and Leaves Piebiep Goufo 1,* , Rupesh Kumar Singh 2 and Isabel Cortez 1 1 Centre for the Research and Technology of Agro-Environment and Biological Sciences, Departamento de Agronomia, Universidade de Trás-os-Montes e Alto Douro, Quinta de Prados, 5000-801 Vila Real, Portugal; [email protected] 2 Centro de Química de Vila Real, Universidade de Trás-os-Montes e Alto Douro, Quinta de Prados, 5000-801 Vila Real, Portugal; [email protected] * Correspondence: [email protected] Received: 15 April 2020; Accepted: 5 May 2020; Published: 8 May 2020 Abstract: Due to their biological activities, both in plants and in humans, there is a great interest in finding natural sources of phenolic compounds or ways to artificially manipulate their levels. During the last decade, a significant amount of these compounds has been reported in the vegetative organs of the vine plant. In the roots, woods, canes, stems, and leaves, at least 183 phenolic compounds have been identified, including 78 stilbenes (23 monomers, 30 dimers, 8 trimers, 16 tetramers, and 1 hexamer), 15 hydroxycinnamic acids, 9 hydroxybenzoic acids, 17 flavan-3-ols (of which 9 are proanthocyanidins), 14 anthocyanins, 8 flavanones, 35 flavonols, 2 flavones, and 5 coumarins. There is great variability in the distribution of these chemicals along the vine plant, with leaves and stems/canes having flavonols (83.43% of total phenolic levels) and flavan-3-ols (61.63%) as their main compounds, respectively. In light of the pattern described from the same organs, quercetin-3-O-glucuronide, quercetin-3-O-galactoside, quercetin-3-O-glucoside, and caftaric acid are the main flavonols and hydroxycinnamic acids in the leaves; the most commonly represented flavan-3-ols and flavonols in the stems and canes are catechin, epicatechin, procyanidin B1, and quercetin-3-O-galactoside.
    [Show full text]
  • Volume 13. Issue 11. Pages 1419-1568. 2018 ISSN 1934-578X (Printed); ISSN 1555-9475 (Online) NPC Natural Product Communications
    Volume 13. Issue 11. Pages 1419-1568. 2018 ISSN 1934-578X (printed); ISSN 1555-9475 (online) www.naturalproduct.us NPC Natural Product Communications EDITOR-IN-CHIEF HONORARY EDITOR DR. PAWAN K AGRAWAL PROFESSOR GERALD BLUNDEN Natural Product Inc. The School of Pharmacy & Biomedical Sciences, 7963, Anderson Park Lane, University of Portsmouth, Westerville, Ohio 43081, USA Portsmouth, PO1 2DT U.K. [email protected] [email protected] EDITORS ADVISORY BOARD PROFESSOR MAURIZIO BRUNO Department STEBICEF, Prof. Giovanni Appendino Prof. Niel A. Koorbanally University of Palermo, Viale delle Scienze, Novara, Italy Durban, South Africa Parco d’Orleans II - 90128 Palermo, Italy Prof. Chiaki Kuroda [email protected] Prof. Norbert Arnold Halle, Germany Tokyo, Japan PROFESSOR CARMEN MARTIN-CORDERO Department of Pharmacology, Faculty of Pharmacy, Prof. Yoshinori Asakawa Prof. Hartmut Laatsch Tokushima, Japan Gottingen, Germany University of Seville, Seville, Spain [email protected] Prof. Vassaya Bankova Prof. Marie Lacaille-Dubois PROFESSOR VLADIMIR I. KALININ Sofia, Bulgaria Dijon, France G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Prof. Roberto G. S. Berlinck Prof. Shoei-Sheng Lee Far Eastern Branch, Russian Academy of Sciences, São Carlos, Brazil Taipei, Taiwan Pr. 100-letya Vladivostoka 159, 690022, Vladivostok, Russian Federation Prof. Anna R. Bilia Prof. M. Soledade C. Pedras [email protected] Florence, Italy Saskatoon, Canada PROFESSOR YOSHIHIRO MIMAKI Prof. Geoffrey Cordell Prof. Luc Pieters School of Pharmacy, Chicago, IL, USA Antwerp, Belgium Tokyo University of Pharmacy and Life Sciences, Prof. Fatih Demirci Prof. Peter Proksch Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan Eskişehir, Turkey Düsseldorf, Germany [email protected] Prof.
    [Show full text]
  • Grapevine Cane Extracts: Raw Plant Material, Extraction Methods, Quantification, and Applications
    biomolecules Review Grapevine Cane Extracts: Raw Plant Material, Extraction Methods, Quantification, and Applications María José Aliaño-González 1, Tristan Richard 2 and Emma Cantos-Villar 1,* 1 Instituto de Investigación y Formación Agraria y Pesquera (IFAPA), Consejería de Agricultura, Ganadería, Pesca y Desarrollo Sostenible, Rancho de la Merced, Ctra. Cañada de la Loba, CA-3102 km 3.1, 11471 Jerez de la Frontera, Spain; [email protected] 2 Université de Bordeaux, ISVV, EA 3675 Groupe d’Etude des Substances Végétales à Activité Biologique, 33882 Villenave d’Ornon, France; [email protected] * Correspondence: [email protected]; Tel.: +34-671-560-353 Received: 19 June 2020; Accepted: 6 August 2020; Published: 17 August 2020 Abstract: Grapevine canes are viticulture waste that is usually discarded without any further use. However, recent studies have shown that they contain significant concentrations of health-promoting compounds, such as stilbenes, secondary metabolites of plants produced as a response to biotic and abiotic stress from fungal disease or dryness. Stilbenes have been associated with antioxidant, anti-inflammatory, and anti-microbial properties and they have been tested as potential treatments of cardiovascular and neurological diseases, and even cancer, with promising results. Stilbenes have been described in the different genus of the Vitaceae family, the Vitis genera being one of the most widely studied due to its important applications and economic impact around the world. This review presents an in-depth study of the composition and concentration of stilbenes in grapevine canes. The results show that the concentration of stilbenes in grapevine canes is highly influenced by the Vitis genus and cultivar aspects (growing conditions, ultraviolet radiation, fungal attack, etc.).
    [Show full text]
  • Anti-Inflammatory Effects of Vitisinol a and Four Other Oligostilbenes From
    molecules Communication Anti-Inflammatory Effects of Vitisinol A and Four Other Oligostilbenes from Ampelopsis brevipedunculata var. Hancei Chi-I Chang 1, Wei-Chu Chien 1, Kai-Xin Huang 1 and Jue-Liang Hsu 1,2,3,* ID 1 Department of Biological Science and Technology, National Pingtung University of Science and Technology, Pingtung 900, Taiwan; [email protected] (C.-I.C.); [email protected] (W.-C.C.) [email protected] (K.-X.H.) 2 Research Center for Tropic Agriculture, National Pingtung University of Science and Technology, Pingtung 900, Taiwan 3 Research Center for Austronesian Medicine and Agriculture, National Pingtung University of Science and Technology, Pingtung 900, Taiwan * Correspondence: [email protected]; Tel.: +886-8-770-3202 (ext. 5197) Received: 4 July 2017; Accepted: 14 July 2017; Published: 17 July 2017 Abstract: In this study, the cytotoxicities and anti-inflammatory activities of five resveratrol derivatives—vitisinol A, (+)-"-viniferin, (+)-vitisin A, (−)-vitisin B, and (+)-hopeaphenol—isolated from Ampelopsis brevipedunculata var. hancei were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and lipopolysaccharide (LPS)-stimulated RAW264.7 cells, respectively. The result from MTT assay analysis indicated that vitisinol A has lower cytotoxicity than the other four well-known oligostilbenes. In the presence of vitisinol A (5 µM), the significant reduction of inflammation product (nitric oxide, NO) in LPS-induced RAW264.7 cells was measured using Griess reaction assay. In addition, the under-expressed inflammation factors cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) in LPS-induced RAW264.7 cells monitored by Western blotting simultaneously suggested that vitisinol A has higher anti-inflammatory effect compared with other resveratrol derivatives.
    [Show full text]
  • Stilbenoides
    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).
    [Show full text]
  • Combined MS/MS-NMR Annotation Guided Discovery of Iris Lactea Var
    molecules Article Combined MS/MS-NMR Annotation Guided Discovery of Iris lactea var. chinensis Seed as a Source of Viral Neuraminidase Inhibitory Polyphenols Hyun Woo Kim 1 , Soo Sung Kim 1, Kyo Bin Kang 2 , Byeol Ryu 1, Eunjin Park 1, Jungmoo Huh 1, Won Kyung Jeon 3,4, Hee-Sung Chae 1, Won Keun Oh 1 , Jinwoong Kim 1, Sang Hyun Sung 1 and Young-Won Chin 1,* 1 Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, Korea; [email protected] (H.W.K.); [email protected] (S.S.K.); [email protected] (B.R.); [email protected] (E.P.); [email protected] (J.H.); [email protected] (H.-S.C.); [email protected] (W.K.O.); [email protected] (J.K.); [email protected] (S.H.S.) 2 College of Pharmacy, Sookmyung Women’s University, Seoul 04310, Korea; [email protected] 3 Herbal Medicine Research Division, Korea Institute of Oriental Medicine, Daejeon 34054, Korea; [email protected] 4 Convergence Research Center for Diagnosis, Treatment and Care System of Dementia, Korea Institute of Science and Technology, Seoul 02792, Korea * Correspondence: [email protected]; Tel.: +82-2-880-7859 Academic Editor: Francesco Cacciola Received: 29 June 2020; Accepted: 23 July 2020; Published: 26 July 2020 Abstract: In this study, the chemical diversity of polyphenols in Iris lactea var. chinensis seeds was identified by combined MS/MS-NMR analysis. Based on the annotated chemical profile, the isolation of stilbene oligomers was conducted, and consequently, stilbene oligomers (1-10) were characterized.
    [Show full text]
  • Since January 2020 Elsevier Has Created a COVID-19 Resource Centre with Free Information in English and Mandarin on the Novel Coronavirus COVID- 19
    Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID- 19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active. European Journal of Medicinal Chemistry 202 (2020) 112541 Contents lists available at ScienceDirect European Journal of Medicinal Chemistry journal homepage: http://www.elsevier.com/locate/ejmech Review article Natural and nature-inspired stilbenoids as antiviral agents * Luce M. Mattio 1, Giorgia Catinella 1, Andrea Pinto, Sabrina Dallavalle Department of Food, Environmental and Nutritional Sciences, Universita Degli Studi di Milano, Via Celoria 2, 20133, Milano, Italy article info abstract Article history: Viruses continue to be a major threat to human health. In the last century, pandemics occurred and Received 9 April 2020 resulted in significant mortality and morbidity. Natural products have been largely screened as source of Received in revised form inspiration for new antiviral agents. Within the huge class of plant secondary metabolites, resveratrol- 24 May 2020 derived stilbenoids present a wide structural diversity and mediate a great number of biological re- Accepted 4 June 2020 sponses relevant for human health.
    [Show full text]