Separation and identification of highly fluorescent compounds derived from trans-resveratrol in the leaves of Vitis vinifera infected by Plasmopara viticola

. 2012 Mar 06 ; 17 (3) : 2773-83. [epub] 20120306

Jazyk angličtina Země Švýcarsko Médium electronic

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/pmid22395406

A method for identification of highly fluorescent compounds in vine leaves infected by Plasmopara viticola was developed using reversed phase liquid chromatography with simultaneous diode array and fluorometric detection. Fluorescent compounds were extracted from leaves with a methanol-water mixture (70:30). Separation by HPLC was performed using a C(18) column and gradient elution with water-acetonitrile mixtures (20-80% of acetonitrile). The main unknown fluorescent compound was identified by line spectral comparison with a standard obtained by UV photoisomerization of trans-resveratrol glucoside, and its structure was confirmed by liquid chromatography-mass spectrometry. Identification and structural elucidation of the fluorescent compound in the leaves of Vitis vinifera allows early detection of Plasmopara viticola invasion.

Zobrazit více v PubMed

Langcake P., Pryce R.J. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury. Physiol. Plant. Pathol. 1976;9:77–86. doi: 10.1016/0048-4059(76)90077-1. DOI

Langcake P., Pryce R.J. The production of resveratrol and the viniferins by grapevines in response to ultraviolet irradiation. Phytochemistry. 1977;16:1193–1196.

Jeandet P., Bessis R., Maume B.F., Meunier P., Peyron D., Trollat P. Effect of enological practices on the resveratrol isomer content of wine. J. Agric. Food Chem. 1995;43:316–319. doi: 10.1021/jf00050a010. DOI

Lamuela-Raventós R.M., Romero-Pérez A.I., Waterhouse A.L., de la Torre-Boronat M.C. Direct HPLC analysis of cis- and trans-resveratrol and piceid isomers in Spanish red Vitis vinifera wines. J. Agric. Food Chem. 1995;43:281–283. doi: 10.1021/jf00050a003. DOI

Goldberg D.M., Ng E., Karumanchiri A., Diamandis E.P., Soleas G.J. Resveratrol glucosides are important components of commercial wines. Am. J. Enol. Viticult. 1996;47:415–420.

Sato M., Suzuki Y., Okuda T., Yokotsuka K. Content of resveratrol, piceid, and their isomers in commercially available wines made from grapes cultivated in Japan. Biosci.Biotechnol. Biochem. 1997;61:1800–1805. doi: 10.1271/bbb.61.1800. PubMed DOI

Ribeiro de Lima M.T., Waffo-Téguo P., Teissedre P.L., Pujolas A., Vercauteren J., Cabanis J.C., Mérillon J.M. Determination of stilbenes (trans-astringin, cis-and trans-piceid, and cis- and trans-resveratrol) in Portuguese wines. J. Agric. Food Chem. 1999;47:2666–2670. doi: 10.1021/jf9900884. PubMed DOI

Gatto P., Vrhovsek U., Muth J., Segala C., Romualdi C., Fontana P., Pruefer D., Stefanini M., Moser C., Mattivi F., Velasco R. Ripening and genotype control stilbene accumulation in healthy grapes. J. Agric. Food Chem. 2008;56:11773–11785. PubMed

Adrian M., Jeandet P., Douillet-Breuil A.C., Tesson L., Bessis R. Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation. J. Agric. Food Chem. 2000;48:6103–6105. doi: 10.1021/jf0009910. PubMed DOI

Romero-Perez A.I., Lamuela-Raventos R.M., Andres-Lacueva C., de La Torre-Boronat M.C. Method for the quantitative extraction of resveratrol and piceid isomers in grape berry skins. Effect of powdery mildew on the stilbene content. J. Agric. Food Chem. 2001;49:210–215. PubMed

van Zeller de Macedo Basto Goncalves M.I., Bavaresco L., Civardi S., Ferrari F. Interactions between Plasmopara viticola infection and stilbene synthesis in leaves and berries of ten ‘Cabernet Sauvignon’ clones. Vitis. 2011;50:119–122.

Mattivi F., Vrhovsek U., Malacarne G., Masuero D., Zulini L., Stefanini M., Moser C., Velasco R., Guella G. Profiling of resveratrol oligomers, important stress metabolites, accumulating in the leaves of hybrid Vitis vinifera (Merzling × Teroldego) genotypes infected with Plasmopara viticola. J. Agric. Food Chem. 2011;59:5364–5375. PubMed

Bábíková P., Vrchotová N., Tříska J., Kyseláková M. Content of trans-resveratrol in leaves and berries of interspecific grapevine (Vitis sp.) varieties. Czech J. Food Sci. 2008;26:13–17.

Otreba J.B., Berghofer E., Wendelin S., Eder R. Polyphenole und antioxidative kapazität in österreichischen weinen aus konventioneller und biologischer traubenproduktion. Mitteilungen Klosterneuburg, Rebe und Wein. Obstbau und Früchteverwertung. 2006;56:22–32.

Frankel E.N., Waterhouse A.L., Kinsella J.E. Inhibition of human LDL oxidation by resveratrol. Lancet. 1993;341:1103–1104. PubMed

Orsini F., Pelizzoni F., Verotta L., Aburjai T. Isolation, synthesis, and antiplatelet aggregation activity of resveratrol-3-O-β-D-glucopyranoside and related compounds. J. Nat. Prod. 1997;60:1082–1087. doi: 10.1021/np970069t. PubMed DOI

Kimura Y., Okuda H., Arichi S. Effects of stilbenes on arachidonate metabolism in leucocytes. Biochim. Biophys.Acta. 1985;834:275–278. doi: 10.1016/0005-2760(85)90167-5. PubMed DOI

Pace-Asciak C.R., Hahn S., Diamandis E.P., Soleas G., Goldberg D.M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: Implication for protection against coronary heart disease. Clin. Chim. Acta. 1995;235:207–219. doi: 10.1016/0009-8981(95)06045-1. PubMed DOI

Gehm B.D., McAndrews J.M., Chien P.-Y., Jameson J.L. Resveratrol, a polyphenolic compound found in grapes and wine is an agonist for the estrogen receptor. Proc. Natl. Acad. Sci. USA. 1997;94:14138–14143. doi: 10.1073/pnas.94.25.14138. PubMed DOI PMC

Guilford J., Pezzuto J.M. Wine and health: A review. Am. J. Enol. Viticult. 2011;62:471–486. doi: 10.5344/ajev.2011.11013. DOI

Vang O., Das D.K., editors. Resveratrol and health. Annals of the New York Academy of Sciences. Wiley-Blackwell; New York, NY, USA: 2011. pp. 1–170.

Chong J., Poutaraud A., Hugueney P. Metabolism and roles of stilbenes in plants. Plant Sci. 2009;177:143–155. doi: 10.1016/j.plantsci.2009.05.012. DOI

Vicinelli V., Ceroni P., Maestri M., Lazzari M., Balzani V., Lee S.K., van Heyst J., Vogtle F. Photochemical and photophysical properties of a poly(propylene amine) dendrimer functionalised with E-stilbene units. Org. Biomol. Chem. 2004;2:2207–2213. doi: 10.1039/b404463k. PubMed DOI

Montsko G., Pour Nikfardjam M.S., Szabo Z., Boddi K., Lorand T., Ohmacht R., Mark L. Determination of products derived from trans-resveratrol UV photoisomerisation by means of HPLC-APCI-MS. J. Photochem. Photobio. A. 2008;196:44–50. doi: 10.1016/j.jphotochem.2007.11.011. DOI

Merás I.D., Díaz T.G., Rodríguez D.A. Determination of piceid by photochemically induced fluorescence and second-derivative: Response surface methodology for the optimization of a liquid-liquid extraction procedure for its analysis in wine samples. Talanta. 2008;74:675–682. doi: 10.1016/j.talanta.2007.06.049. PubMed DOI

Baderschneider B., Winterhalter P. Isolation and characterization of novel stilbene derivatives from Riesling wine. J. Agric. Food Chem. 2000;48:2681–2686. doi: 10.1021/jf991348k. PubMed DOI

Najít záznam

Citační ukazatele

Nahrávání dat ...

Možnosti archivace

Nahrávání dat ...