Separation and identification of highly fluorescent compounds derived from trans-resveratrol in the leaves of Vitis vinifera infected by Plasmopara viticola
Language English Country Switzerland Media electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
22395406
PubMed Central
PMC6269111
DOI
10.3390/molecules17032773
PII: molecules17032773
Knihovny.cz E-resources
- MeSH
- Chromatography, Liquid standards MeSH
- Phenanthrenes chemistry isolation & purification MeSH
- Fluorescent Dyes chemistry isolation & purification MeSH
- Glucosides chemistry isolation & purification radiation effects MeSH
- Mass Spectrometry standards MeSH
- Isomerism MeSH
- Plant Leaves chemistry metabolism microbiology MeSH
- Plant Diseases microbiology MeSH
- Peronospora * MeSH
- Reference Standards MeSH
- Resveratrol MeSH
- Plant Extracts chemistry isolation & purification MeSH
- Stilbenes chemistry radiation effects MeSH
- Ultraviolet Rays MeSH
- Vitis chemistry metabolism microbiology MeSH
- Chromatography, High Pressure Liquid MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 2,4,6-trihydroxyphenanthrene-2-O-glucoside MeSH Browser
- Phenanthrenes MeSH
- Fluorescent Dyes MeSH
- Glucosides MeSH
- polydatin MeSH Browser
- Resveratrol MeSH
- Plant Extracts MeSH
- Stilbenes MeSH
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.
See more in 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
Various extraction methods for obtaining stilbenes from grape cane of Vitis vinifera L
