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

Abstract

Keywords: Natural products / Dyes/Pigments / Anthocyanins / Polyphenols / Ellagitannins Kinetic and thermodynamic UV/Vis and structural NMR spectroscopic investigations on the anthocyano-ellagitannin hybrid 1-deoxyvescalagin-(1βǞ8)-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-

Phenolic Composition and Related Properties of Aged Wine Spirits: Influence of Barrel Characteristics. A Review

“…Concerning the resulting sensory properties, positive correlations between the phenolic composition and the color were established [23,39,40], which are in accordance with the findings in studies on Porto wine [41] and wine [42][43][44][45][46]. Notwithstanding the intricate effect of compounds on aroma and flavour owing to the complexity of their interactions and the multiple sensations involved [47,48], some features have been often related to the phenolic composition of the aged wine spirit and of other aged beverages.…”

“…3%, 0.03%, 0.03% and 0.03%, respectively; that is, other unidentified ellagitannins are likely to be extracted from the wood into the wine spirit and to have a greater contribution to the total amount. Actually, so far, few soluble tannins have been found in the aged wine spirit, contrasting with the increasing number of tannins and derived compounds detected in the aged wine [43,133].…”

Optical properties of wine pigments: theoretical guidelines with new methodological perspectives

“…As an example, such bathochromic shifts (by 25 nm, corresponding to red-to-purple hue evolution) observed for two anthocyano-ellagitannin hybrid pigments at wine pH compared to the corresponding anthocyanin and anthocyanidin derivatives could not be rationalized based on ZINDO//AM1 and TD-B3LYP/6-31G(d) calculations. 72 Even though the spectral effect was clearly due to the intramolecular interactions between pigment and copigment, this level of calculations failed at properly describing the complexity of the observed optical behavior, partially attributed to CT in these complexes. With semi-empirical methods or inadequate DFT functionals, the ES description is erroneous when CT plays a significant role.…”

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

“…Furthermore, disorders of the routine patterns in uniting the component parts frequently appear in higher ellagitannins. In addition, the family includes numerous component parts, including overoxidation 8,9 , modifications of the HHDP group 10 , conjugation with other natural constituents [11][12][13] and production of the highly oxygenated diaryl ethers. Among these factors conferring structural diversity, the production of highly oxygenated diaryl ethers, C-O digallates, is the most significant.…”