Supramolecular approaches to the study of the astringency elicited by wine phenolic compounds

Chemical and sensory changes occurring in red wine during ageing in oak barrique are due to the slow and gradual entrance of oxygen along with a release of ellagic tannin from the wood. Though oxygen can enter the cask through the bunghole, it is not clear the role of permeation through the wood staves as well as the amount of oxygen entering by permeation. The distribution of the released ellagic tannins in the wine ageing is also unknown. The oxygen passing through the bunghole may have a different wine ageing effect compared to the oxygen permeating through the wooden staves owing to the uneven ellagic tannin concentration throughout the wine.

Phenolic compounds are secondary metabolites of grapes. Plants produce a wide variety of this type of metabolites through diverse biosynthesis pathways and their production is sometimes a response to external stimuli, either environmental or biotic stresses. Some of them may act as chemical defenses against pathogens or herbivores and their synthesis is increased when the attack exists. However, it is remarkable that the synthesis of these interesting compounds can be activated even when the stimulus is not present, with the use of elicitors. These are substances that when applied exogenously trigger the biosynthetic pathways conducting to the synthesis of these defense compounds.

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.

Among red wines ethyl esters, those from short hydroxylated and branched-chain aliphatic acids constitute a family with a particular behavior and sensory importance. They have been previously discussed in the literature [1] and recent studies have established that some of them were strongly involved in of red wines’ fruity aroma [2]. As some among them have an asymmetrical carbon atom, it seemed important to separate their different enantiomers to obtain an accurate assessment of their organoleptic impact. Three chiral esters have been identified, presenting alkyl and/or hydroxyle substituants: ethyl 2-hydroxy-4-methylpentanoate, ethyl 2-methylbutanoate, and ethyl 3-hydroxybutanoate.

Wine color is one of the main organoleptic characteristics influencing its quality. It is of especial interest in red vinifications due to the economic resources that wineries have to invest for the extraction of the phenolic compounds responsible of wine color, compounds that are mainly located inside the skin cell vacuoles. Moreover, these phenolic compounds not only influence color but also other organoleptic properties such as body, mouthfeel, astringency and flavour. The transference of phenolic compounds from grapes to must during vinification is closely related with the type of grapes and the winemaking technique.