Pathway Leading to the Formation of Anthocyanin−Vinylphenol Adducts and Related Pigments in Red Wines

Abstract

On the basis of observations from Vitis vinifera cv. Pinotage wines and experiments performed in model wine medium, a new chemical pathway responsible for the formation of anthocyanin-vinylphenol adducts in red wines is described. Until now, these pigments have been considered to be reaction products of anthocyanins and vinylphenols, the latter being generated during fermentation by enzymatic decarboxylation of the respective cinnamic acids. The mechanism of the novel pathway, involving intact hydroxycinnamic acid and anthocyanin, is explained. Only cinnamic acids with electron-donating substituents on the aromatic ring, such as coumaric acid, ferulic acid, caffeic acid, and sinapic acid, undergo this conversion, as they stabilize an intermediately formed carbenium ion. Decarboxylation and oxidation of the pyran moieties are the final steps in the generation of the corresponding 4-vinylphenol, 4-vinylguaiacol, 4-vinylcatechol, and 4-vinylsyringol adducts of anthocyanins in red wine.

Volatile composition and sensory characteristics of Carménère wines macerating with Colombian (Quercus humboldtii) oak chips compared to wines macerated with American (Q. alba) and European (Q. petraea) oak chips

“…This decrease was more significant, as a decrease of approximately 90% was observed after 2 months while our greatest decrease of 12% was recorded after 3 months, probably because their initial concentration was higher: about 110 µg/l. The fact that the oak contained this compound can be explained since it has been observed to form different reactions with anthocyanin compounds and is usually absorbed by the wood (Schwarz, Wabnitz, & Winterhalter, 2003;Barrera-Garcíaet al, 2006) or transformed into 4-ethylguaiacol. The concentration of this compound after 7 days' contact with the different species or origins of oak chips was similar in all wines, since no significant differences were found between them.…”

Saccharomyces cerevisiae, Non-Saccharomyces Yeasts and Lactic Acid Bacteria in Sequential Fermentations: Effect on Phenolics and Sensory Attributes of South African Syrah Wines

“…Anthocyanin monomers are responsible for the development of the red colour, whilst their acetylated and coumaroylated derivatives provide stability to the red colour of young wines (Ribéreau-Gayon et al, 2006;Gawel & Godden, 2008). Wine colour also depends on the polymerisation (modification) of anthocyanins during vinification, wine storage and wine maturation (Schwarz et al, 2003). Phenolic compound concentrations in wine can also vary according to grape cultivar, viticultural practices, skin maceration temperature (Cheynier et al, 1997;Ribéreau-Gayon et al, 2006) and grape pomace contact time (Mazza & Francis, 1995;Ribéreau-Gayon et al, 2006;Song et al, 2015).…”

Comprehensive two-dimensional liquid chromatographic analysis of anthocyanins

“…In addition, several related structures differing only in the substitution pattern of the vinylphenol moiety (and therefore of the parent cinnamic acid) have been identified in wine [35,66,67] vinylcatechol), resulting from the reaction between malvidin-3-glucoside and caffeic acid, was the first compound of this class to be identified and was named after Pinotage wine in which it was identified. Higher concentrations of Pinotin A are found in aged compared to young wines [68].…”