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

被引：73

作者：

Chassaing, Stefan ^{[2
,3
]}

Lefeuvre, Dorothee ^{[2
,3
,4
]}

Jacquet, Remi ^{[2
,3
]}

Jourdes, Michael ^{[2
,3
,4
]}

Ducasse, Laurent ^{[3
]}

Galland, Stephanie ^{[1
]}

Grelard, Axelle ^{[2
]}

Saucier, Cedric ^{[4
]}

Teissedre, Pierre-Louis ^{[4
]}

Dangles, Olivier ^{[1
]}

Quideau, Stephane ^{[2
,3
]}

机构：

[1] Univ Avignon & Pays Vaucluse, INRA, UMR 408, F-84000 Avignon, France

[2] Inst Europeen Chim & Biol, F-33607 Pessac, France

[3] Univ Bordeaux, Inst Mol Sci, CNRS, UMR 5255, F-33405 Talence, France

[4] Univ Bordeaux, Inst Sci Vigne & Vin, INRA, Bordeaux Aquitaine UMR 1219, F-33882 Villenave Dornon, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 01期

关键词：

Natural products; Dyes/Pigments; Anthocyanins; Polyphenols; Ellagitannins; RED WINE; FLAVANOL PIGMENTS; COPIGMENTATION; IDENTIFICATION; COMPLEXATION; CHROMATOGRAPHY; CHEMISTRY; HYDRATION; STACKING; ADDUCTS;

D O I：

10.1002/ejoc.200901133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：55 / 63

页数：9

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