Structural Features of Copigmentation of Oenin with Different Polyphenol Copigments

Natércia Teixeira, Luís Cruz, Natércia F. Brás, Nuno Mateus, Maria Jo?o Ramos, and Victor de Freitas

Abstract

The copigmentation binding constants (K) for the interaction of different copigments with oenin (major red wine anthocyanin) were determined. All tests were performed in a 12% ethanol citrate buffer solution (0.2 M) at pH 3.5, with an ionic strength adjusted to 0.5 M by the addition of sodium chloride. Over the past years, several copigmentation studies were made and many copigments were tested, but none of them included prodelphinidin B3 or a dimeric-type adduct like oenin-(O)-catechin, probably due to the difficulty in obtaining them. The data yielded from this study allowed concluding that (a) the presence of a pyrogallol group in the B ring of the flavan-3-ol structure slightly increases the copimentation potential and (b) within all copigments tested oenin-(O)-catechin was revealed to be the best. According to computational studies performed on epicatechin/oenin, epigallocatechin/oenin, procyanidin B3/oenin, and oenin-(O)-catechin/oenin complexes, the ΔGbinding energy of the oenin-(O)-catechin/oenin complex is the most negative compared to the other copigmentation

(?)Epigallocatechin (EGC) and (?)-epigallocatechin gallate (EGCG) were purchased from Biopurify Phytochemicals Ltd. (Sichuan, China).