Red wine substituted esters involved in fruity aromatic expression: an enantiomeric approach to understand their sensory impact and their pathway formation

Vineyard exposure to smoke can lead to grapes and wine which exhibit objectionable smoky and ashy aromas and flavours, more commonly known as ‘smoke taint’ [1, 2]. In the last decade, significant bushfires have occurred around the world, including near wine regions in Australia, Canada, South Africa and the USA, as a consequence of the warmer, drier conditions associated with climate change. Considerable research has subsequently been undertaken to determine the chemical, sensory and physiological consequences of grapevine exposure to smoke. The sensory attributes associated with smoke-tainted wine have been linked to the presence of several smoke-derived volatile phenols, such as guaiacols, syringols and cresols [2].

Condensed tannins (also called proanthocyanidins) are a widely distributed throughout in plants kingdom and are one of the most important classes of secondary metabolites, in addition, they are part of the human diet. In wine, they are extracted during the winemaking process from grape skins and seeds. These compounds play an important role in red wine organoleptic characteristics such as color, bitterness and astringency. Condensed tannins in red wine are oligomers and polymers of flavan-3-ols unit such as catechin, epicatechin, epigallocatechin and epicatechin-3-O-gallate. The monomeric units can be linked among them with direct interflavanoid linkage or mediated by aldehydes.

Astringency sensation decreases slowly during the aging of red wine. Complex reactions of condensation and precipitation of wine polyphenols are involved in this phenomenon. Wine composition and conditions of aging, such as temperature and oxygen availability, strongly influence evolution of the phenol matrix. Recently, a Post-Fermentative cold Maceration (PFM) technique was tested with the aim of accelerating reactions leading to the reduction of astringency and exploiting chemical compounds not extracted from the solid parts of grapes during the previous traditional maceration phase. To this purpose, an innovative maceration system was engineered and used to perform PFM trials on marc derived from vinification of different varieties of red grapes.

The objective of this study is to review the scientific evidences and to advance into the knowledge of the molecular mechanisms of astringency. Astringency has been described as the drying, roughing and puckering sensation perceived when some food and beverages are tasted (1). The main, but possibly not the only, mechanism for the astringency is the precipitation of salivary proteins (2,3). Between phenolic compounds found in red wines, flavan-3-ols are the group usually related to the development of this sensation. Other compounds, phenolic or not, like anthocyanins, polysaccharides and mannoproteins could act modifying or modulating astringency perception by hindering the interaction between flavanols and salivary proteins either because of their interaction with the flavanols or because of their interaction with the salivary proteins.

Tannin, anthocyanins and their reaction products play a major role in the quality of red wines. They contribute to their sensory characteristics, particularly colour and astringency. Grape tannins and anthocyanins are extracted during red wine fermentation. However, their concentration and composition change over time, due to their strong chemical reactivity1. It is also well known that yeasts influence the wine phenolic content, either through the release of metabolites involved in the formation of derived pigments1, or through polyphenol adsorption2,3.