New Stilbenoid Glucosides Isolated from Vitis vinifera Cell Suspension Cultures (cv. Cabernet Sauvignon)

Abstract

Three new monomeric stilbenoid glucosides, (Z)- and (E)-resveratrol 3,5-O-β-diglucosides (1 and 2, respectively) and (Z)-resveratrol 3,5,4′-O-β-triglucoside (3), were isolated from an extract of Vitis vinifera cell cultures (Cabernet Sauvignon) together with the known (E)- and (Z)-piceids and (E)- and (Z)-resveratrol 3,4′-O-β-diglucosides that have already been identified in a Gamay cell culture extract. The structure determinations were based on spectroscopic data analysis.

References

• 1 Jang M J, Cai L, Udeani G O, Slowing K V, Thomas C F, Beecher C WW. et al . Cancer chemopreventive activity of resveratrol, a natural product derived from grapes.  Science. 1997;  275 218-20
• 2 Fauconneau B, Waffo-Téguo P, Huguet F, Barrier L, Decendit A, Mérillon J. Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests.  Life Sci. 1997;  61 2103-10
• 3 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: implications for protection against coronary heart disease.  Clin Chim Acta. 1995;  235 207-19
• 4 Mattivi F, Reniero R, Korhammer S J. Isolation, characterization, and evolution in red wine vinification of resveratrol monomers.  J Agric Food Chem. 1995;  43 1820-3
• 5 Décendit A, Waffo-Téguo P, Richard T, Krisa S, Vercautern J, Monti J P. et al . Galloylated catechins and stilbene diglucosides in Vitis vinifera cell suspension cultures.  Phytochemistry. 2002;  60 795-8
• 6 Waffo-Téguo P, Decendit A, Deffieux G, Vercauteren J, Mérillon J M. trans-Resveratrol-3-O-β-glucoside (piceid) in cell suspension cultures of Vitis vinifera .  Phytochemistry. 1996;  42 1591-3
• 7 Waffo-Téguo P, Decendit A, Krisa S, Deffieux G, Vercauteren J, Mérillon J M. Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from Vitis vinifera cell cultures.  J Nat Prod. 1998;  61 655-7
• 8 Krisa S, Larronde F, Budzinski H, Decendit A, Deffieux G, Mérillon J M. Stilbene production by Vitis vinifera cell suspension cultures: methyl jasmonate induction and ¹³C biolabeling.  J Nat Prod. 1999;  62 1688-90
• 9 Trela B C, Waterhouse A L. Resveratrol: isomeric molar absorptivities and stability.  J Agric Food Chem. 1996;  44 1253-7
• 10 Pezet R, Pont V, Cuenat P. Method to determine resveratrol and pterostilbene in grape berries and wines using high-performance liquid chromatography and highly sensitive fluorimetric detection.  J Chromatogr A. 1994;  663 191-7