Résumé
Kinetic and thermodynamic UV/Vis and structural NMR spectroscopic investigations on the anthocyano-ellagitannin hybrid 1-deoxyvescalagin-(1 beta -> 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 pi-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.