Red cabbage

Malvidin

Molecule

Glucoside

Food science

Intermolecular force

Stereochemistry

Alternative medicine

Organic chemistry

Pelargonidin

Gallic acid

Pigment

Substituent

Antioxidant

Cyanidin

Petunidin

Delphinidin

Anthocyanin

Peonidin

Medicine

Chemistry

Wine

Pathology

Ring (chemistry)

Food Chemistry

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.

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