Intermolecular copigmentation between five common 3-O-monoglucosidic anthocyanins and three phenolics in red wine
Xu Zhao1, Bo-Wen Ding2, Jia-Wei Qin1
1Center for Viticulture and Enology, College of Food Science & Nutritional Engineering, China Agricultural University, Beijing 100083, China; Key Laboratory of Viticulture and Enology, Ministry of Agriculture and Rural Affairs, Beijing 100083, China.
Abstract:
In this study, intermolecular copigmentation between five primary wine monoglucosidic anthocyanins (cyanidin-3-O-glucoside, peonidin-3-O-glucoside, delphinidin-3-O-glucoside, petunidin-3-O-glucoside, and malvidin-3-O-glucoside) and three common wine phenolics (gallic acid, (-)-epicatechin, and quercetin-3-O-glucoside) were investigated through experimental and theoretical methods, and the influence of substituent pattern of anthocyanin B ring was studied emphatically. Chromatic and thermodynamic analysis showed there were great differences among these different pigment-copigment systems. Spatial conformations of the 15 copigmentation complexes were obtained through theoretical calculation, and diverse π-π stacking modes were observed. These results indicated that the substituent pattern of anthocyanin B ring had significant impact on its affinity to copigments, and more, the structures of pigments and copigments determined the color expression and stability of copigmentation together.
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