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Physicochemical Studies of New Anthocyano‐Ellagitannin Hybrid Pigments: About the Origin of the Influence of Oak C ‐Glycosidic Ellagitannins on Wine Color

2009; Wiley; Volume: 2010; Issue: 1 Linguagem: Inglês

10.1002/ejoc.200901133

1434-193X

Stefan Chassaing, Dorothée Lefeuvre, Rémi Jacquet, Michaël Jourdes, Laurent Ducasse, Stéphanie Galland, Axelle Grélard, Cédric Saucier, Pierre‐Louis Teissèdre, Olivier Dangles, Stéphane Quideau,

Plant biochemistry and biosynthesis

Abstract Kinetic and thermodynamic UV/Vis and structural NMR spectroscopic investigations on the anthocyano‐ellagitannin hybrid 1‐deoxyvescalagin‐(1β→8)‐oenin revealed that its enhanced color stability relative to that of the red‐colored pigment oenin and resulting bathochromism can be rationalized in terms of an intramolecular π‐stacking between the grape‐derived oenin chromophore and the oak‐derived vescalagin 4,6‐hexahydroxydiphenoyl moiety. The results led us to suggest that this bathochromism‐inducing molecular association could be the first ellagitannin‐based molecular‐level explanation of the red‐to‐purple color change that takes place during the aging of wine in oak barrels.