Role of Oak Ellagitannins in the Synthesis of Vitisin A and in the Degradation of Malvidin 3- O-Glucoside: An Approach in Wine-Like Model Systems

J Agric Food Chem. 2022 Oct 19;70(41):13049-13061. doi: 10.1021/acs.jafc.2c00615. Epub 2022 Apr 19.

Abstract

Recent studies highlight the influence that oak ellagitannins can have on wine astringency and color. Direct reactions between flavanols or anthocyanins with vescalagin have been reported to occur, but participation of these compounds in the formation of other types of derivatives has only been suggested but not demonstrated. This study aims at evaluating, in wine-like model systems, the possible different roles of the main oak ellagitannins, castalagin and vescalagin, alone or combined, in the synthesis of vitisin A and in the degradation of malvidin 3-O-glucoside. In the presence of pyruvic acid, the anthocyanin disappeared mainly as a result of the synthesis of vitisin A, whereas in its absence, degradation reactions prevailed. In general, ellagitannins increased the synthesis of vitisin A, decreased the total content of degradation products, and changed the degradation profile, with differences observed between castalagin and vescalagin. The results of the study revealed that the fate of malvidin 3-O-glucoside is conditioned by the presence of ellagitannins.

Keywords: 2,4,6-trihydroxybenzaldehyde; castalagin; degradation products; malvidin 3-O-glucoside; oak ellagitannins; syringic acid; vescalagin; vitisin A.

MeSH terms

  • Anthocyanins / analysis
  • Glucosides
  • Hydrolyzable Tannins / analysis
  • Pyruvic Acid
  • Quercus*
  • Wine* / analysis

Substances

  • malvidin
  • Anthocyanins
  • vescalagin
  • Hydrolyzable Tannins
  • vitisin A
  • Pyruvic Acid
  • Glucosides