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Focusing on bioactive compounds in grapes: stilbenes in Uvalino cv.

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Abstract

Phenolic compounds belonging to the group of stilbenes have recently received a particular attention as bioactive compounds because of their role in plant physiology and for their antioxidant properties. Monomer stilbenes in grapes are mainly present as glycosides. The aim of this work was the identification and quantification of monomer stilbenes (as both free and glycosilated form) in Uvalino grapes, a grapevine variety known for its significant content in stilbenes. Their content in grapes was determined during ripening and overripening stages, in comparison with other phenolic compounds. Piceid (cis and trans form), piceatannol (cis and trans form), cis resveratrol and trans-pterostilbene were identified and quantified in grape skin. Piceid was the most abundant stilbene as both cis and trans forms. As for anthocyanins, the synthesis and the stilbenes accumulation started during veraison, and then, the content of these molecules remained constant with the exception of piceid, whose content slightly increased until harvest. Therefore, stilbenes accumulation seems not to be affected by anthocyanins synthesis. On the contrary, proanthocyanidins, flavonols and hydroxycinnamyl tartrates decreased during ripening. When withering was applied to grapes as a post-harvest treatment, the content of anthocyanins, proanthocyanidins and of the most abundant stilbenes increased, while flavonols and hydroxycinnamyl tartrates decreased. The results suggest that degradation processes during withering are probably weaker or absent in the case of stilbenes, anthocyanins and proanthocyanidins.

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References

  1. Giorcelli A, Sparvoli F, Mattivi F, Tava A, Balestrazzi A, Vrhovsek U, Calligari P, Bollini R, Confalonieri M (2004) Expression of stilbene syntase (StSy) gene from grapevine in transgenic white poplar results in high accumulation of the antioxidant resveratrol glucosides. Transgenic Res 13:203–214

    Article  CAS  Google Scholar 

  2. Chen LG, Wang CC (2009) Preparative separation of oligostilbenes from Vitis thunbergii var. taiwaniana by centrifugal partition chromatography followed by Sephadex LH-20 column chromatography. Separ Purif Techn 66:65–70

    Article  CAS  Google Scholar 

  3. Celotti E, Ferrarini R, Zironi R, Conte LS (1996) Resveratrol content of some wines obtained from dried Valpolicella grapes: recioto and Amarone. J Chromatogr A 730:47–52

    Article  CAS  Google Scholar 

  4. Hall D, De Luca V (2007) Mesocarp localization of a bi-functional resveratrol/hydroxycinnamic acid glucosyltransferase of Concord grape (Vitis labrusca). Plant J 49:579–591

    Article  CAS  Google Scholar 

  5. Mattivi F, Reniero F, Korhammer S (1995) Isolation, characterization and evolution in red wine vinification of resveratrol monomers. J Agric Food Chem 43:1820–1823

    Article  CAS  Google Scholar 

  6. Kammerer D, Claus A, Carle R, Schieber A (2004) Polyphenol Screening from red and White Grape varieties (vitis vinifera L.) by HPLC-DAD-MS/MS. J Agric Food Chem 52:4360–4367

    Article  CAS  Google Scholar 

  7. Romero-Perez A, Ibern-Gomez M, Lamuela-Raventos M, Torre-Boronat MC (1999) Piceid, the major resveratrol derivate in grape juice. J Agric Food Chem 47:1533–1536

    Article  CAS  Google Scholar 

  8. Korhammer S, Reniero F, Mattivi F (1995) An oligostilbene from Vitis roots. Phytochemistry 38:1501–1504

    Article  CAS  Google Scholar 

  9. Landrault N, Larronde F, Delaunay JC, Castagnino C, Vercauteren J, Merillon JM, Gasc F, Cros G, Teissedre PL (2002) Levels of stilbene oligomers and astilbin in French varietal wines and i grapes during noble rot development. J Agric Food Chem 50:2046–2052

    Article  CAS  Google Scholar 

  10. Baderschneider B, Winterhalter P (2000) Isolation and characterization of novel stilbene derivates from Riesling wine. J Agric Food Chem 48:2681–2686

    Article  CAS  Google Scholar 

  11. Versari A, Parpinello GP, Tornielli GB, Ferrarini R, Giulivo C (2001) Stilbene compounds and stilbene synthase expression during ripening, wilting and treatment in grape cultivar corvina. J Agric Food Chem 49:5531–5536

    Article  CAS  Google Scholar 

  12. Gambuti A, Strollo D, Ugliano M, Lecce L, Moio L (2004) Trans-Resveratrol, quercetin, (+)-catechin and (−)-epicatechin content in south Italian monovarietal wines: relationship with maceration tima and marc pressing during winemaking. J Agric Food Chem 52:5747–5751

    Article  CAS  Google Scholar 

  13. Boulton R (2001) The copigmentation of anthocyanins and its role in the color of red wine: a critical review. Am J Enol Vitic 52:67–87

    CAS  Google Scholar 

  14. Baur JA, Pearson K (2006) Resveratrol improves health and survival of mice on a high-calorie diet. Nature 444:337–342

    Article  CAS  Google Scholar 

  15. Clement MV, Hirpara JL, Chawdhury SH, Pervaiz S (1998) Chemopreventive agent resveratrol, a natural product derived from grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells. Blood 92:996–1002

    CAS  Google Scholar 

  16. Acquaviva R, Russo A, Campisi A, Sorrenti V, Di Giacomo C, Barcellona M, Avitabile MA, Vanella A (2002) Antioxidant activity and protective effect on DNA cleavage of resveratrol. J Food Sci 67:137–141

    Article  CAS  Google Scholar 

  17. Pace-Asciak CR, Hahn S, Diamandis EP, Soleas G, Goldberg DM (1995) 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 235:207–219

    Article  CAS  Google Scholar 

  18. Ghiselli A, Nardini M, Baldi A, Scaccini C (1998) Antioxidant activity of different phenolic fraction separated from an Italian red wine. J Agric Food Chem 46:361–367

    Article  CAS  Google Scholar 

  19. Jeandet P, Bessis R, Gautheron B (1991) The production of resveratrol (3,5,4′-trihydroxystilbene) by grape berries in different developmental stages. Am J Enol Vitic 42:41–46

    CAS  Google Scholar 

  20. Adams DO (2006) Phenolics and ripening in grape berries. Am J Enol Vitic 57:249–256

    CAS  Google Scholar 

  21. Borsa D, Di Stefano R (2000) Evoluzione dei polifenoli durante l’appassimento di uve a frutto colorato. Riv Vitic Enol 53:25–35

    CAS  Google Scholar 

  22. Eder R, Wendelin S, Vrhovsek U (2001) Resveratrolgehalte von Trauben und Rotweinen in Abhängigkeit von Lesejargang und Lesetermin. Mitteilungen Klosterneuburg 51:64–78

    CAS  Google Scholar 

  23. Roggero JP, Archier P (1994) Dosage du resvératrol et de l’un de ses glycosides dans les vins. Sci des Aliments 14:99–107

    CAS  Google Scholar 

  24. Lamuela-Raventòs R, Romero-Pérez AI, Waterhouse AL, de la Torre-Boronat MC (1995) Direct HPLC analysis of cis- and trans-Resveratrol and Piceid isomers in Spanish Red Vitis vinifera wines. Am J Enol Vitic 43:281–283

    Google Scholar 

  25. Bavaresco L, Gatti M, Pezzutto S, Fregoni M, Mattivi F (2008) Effect of removal on grape yield, berry composition and stilbene concentration. Am J Enol Vitic 59:292–298

    Google Scholar 

  26. Borsa D, Corino L, Borio M, Monticelli L, Di Stefano R (2003) The Uvalino: a variety responsible for synthesis of high amounts of resveratrol. VII international symposium of oenology, ISBN 2-7430-0649-8

  27. Schneider A, Gerbi V, Redoglia M (1987) A rapid HPLC for separation and determination of major organic acids in grape musts and wine. Am J Vitic Enol 38:151–155

    CAS  Google Scholar 

  28. Di Stefano R, Mattivi F, Caburazzi M, Giustini E, Bonifazi L (2008) Evolution of phenolic composition of Sagrantino grapes during maturation. Riv Vitic Enol 1:39–61

    Google Scholar 

  29. Di Stefano R, Cravero MC (1991) Metodo per lo studio dei polifenoli dell’uva. Riv Vitic Enol 2:37–45

    Google Scholar 

  30. Di Stefano R, Cravero MC (1992) The separation of hydroxycinnamates in wine. Sci Aliments 12:139–144

    Google Scholar 

  31. Trela BC, Waterhouse AL (1996) Resveratrol: isomeric molar absorptivities and stability. J Agric Food Chem 44:1253–1257

    Article  CAS  Google Scholar 

  32. Waterhouse AL, Lamuela-Raventos RM (2001) The occurrence of piceid, a stilbene glucoside, in grape berries. Phytochemistry 22:571–573

    Google Scholar 

  33. Shiozaki S, Nakamura T, Ogata T (2013) Resveratrol productivity of wild grapes nativto Japan. Vitis ficifolia var. Lobata and Vitis ficifolia var Ganebu. Am J Enol Vitic 64:163–168

    Article  CAS  Google Scholar 

  34. Downey OM, Harvey JS, Robinson SP (2003) Analysis of tannins in seeds and skins of Shiraz grapes throughout berry development. Aust J Grape Wine Res 9:15–27

    Article  CAS  Google Scholar 

  35. Mattivi F, Guazzon R, Vrhovsek U, Stefanini M, Velasco R (2006) Metabolite profiling of grape: flavonols and anthocyanins. J Agric Food Chem 54:7692–7702

    Article  CAS  Google Scholar 

  36. Cheynier V, Rigaud J, Souquet J-M, Duprat F, Moutounet M (1990) Must browning in relation to the behaviour of phenolic compounds during oxidation. Am J Enol Vitic 41:346–349

    CAS  Google Scholar 

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Piano, F., Bertolone, E., Pes, D. et al. Focusing on bioactive compounds in grapes: stilbenes in Uvalino cv.. Eur Food Res Technol 237, 897–904 (2013). https://doi.org/10.1007/s00217-013-2060-4

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  • DOI: https://doi.org/10.1007/s00217-013-2060-4

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