Intermolecular copigmentation between five common 3-O-monoglucosidic anthocyanins and three phenolics in red wine model solutions: The influence of substituent pattern of anthocyanin B ring

•Copigmentation between 5 anthocyanins and 3 phenolic copigments were studied.•Chromatic, thermodynamic and theoretical methods were used.•Substituent pattern of anthocyanin B ring had great influence on copigmentation.•Diverse π-π stacking modes were observed through theoretical calculation. In thi...

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Vydáno v:Food chemistry Ročník 326; s. 126960
Hlavní autoři: Zhao, Xu, Ding, Bo-Wen, Qin, Jia-Wei, He, Fei, Duan, Chang-Qing
Médium: Journal Article
Jazyk:angličtina
Vydáno: England Elsevier Ltd 01.10.2020
Témata:
Anthocyanin
anthocyanins
Anthocyanins - analysis
Anthocyanins - chemistry
Chromatic characteristic
Color
gallic acid
Glucosides - analysis
Intermolecular copigmentation
Molecular Structure
Phenols - chemistry
Quercetin - analogs & derivatives
Quercetin - analysis
red wines
Theoretical calculation
Thermodynamics
Wine - analysis
Anthocyanin
Pt
vdW
Mv
Dp
BCP
Intermolecular copigmentation
Thermodynamics
CCP
Theoretical calculation
Chromatic characteristic
Cy
Qg
Ga
HB
Pn
Ec
RCP
ISSN:0308-8146, 1873-7072, 1873-7072
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Shrnutí:•Copigmentation between 5 anthocyanins and 3 phenolic copigments were studied.•Chromatic, thermodynamic and theoretical methods were used.•Substituent pattern of anthocyanin B ring had great influence on copigmentation.•Diverse π-π stacking modes were observed through theoretical calculation. 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.
Bibliografie:ObjectType-Article-1
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ISSN:0308-8146
1873-7072
1873-7072
DOI:10.1016/j.foodchem.2020.126960