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

Glutathione is a tripeptide (γ-Glu-Cys-Gly), which can occur in grapes, in must and in wine prevalently in the reduced form as well as in the oxidized form as glutathione disulfide. The importance of the reduced form of glutathione lies in its antioxidant activity. In must, it limits browning by reducing o-quinones produced by polyphenol oxidase activity on hydroxycinnamic acids; in wine, it exerts a protective effect on various aromatic compounds. Glutathione concentration in wine is lower than in grape juice and variable as it depends on several factors, ranging from the native content of grapes to winemaking technique.

Adrenaline (epinephrine) belongs to catecholamine class. It is a neurotransmitter and both a hormone which is released by the sympathetic nervous system and adrenal medulla in response to a range of stresses in order to regulate blood pressure, cardiac stimulation, relaxation of smooth muscles and other physiological processes. Adrenaline exhibits an effective antioxidant capacity (1). However, adrenalin is capable to auto-oxidation and in this case it generates toxic reactive oxygen intermediates and adrenochrome. Under in vitro conditions, auto-oxidation of adrenaline occurs in an alkaline medium (2).

Fermentation derived sulfidic off-odors due to hydrogen sulfide (H2S) and low molecular weight thiols are commonly encountered in wine production and removed by Cu(II) fining. However, the mechanism underlying Cu(II) fining remains poorly understood, and generally results in increased Cu concentration that lead to deleterious reactions in finished wine. The present study describes a mechanistic investigation of the iron and copper mediated reaction of H2S, cysteine, 3-sulfanylhexan-1-ol, and 6-sulfanylhexan-1-ol with oxygen. The concentrations of H2S, thiols, oxygen, and acetaldehyde were monitored over time. It was found that Cu(II) was rapidly reduced by both H2S and thiols to Cu(I).

Copper and iron are known to substantially impact wine stability through oxidative, reductive or colloidal phenomena. However, the binding of metal ions to different wine components under wine conditions, and the impact of this binding on the ability of the metal ions to induce spoilage processes, is not well understood. This study surveyed a range of red and white wines for an understanding of the variability of broad metal categories within the wines. The techniques utilized included an electrochemical constant current stripping potentiometry technique (ccSP), and solid phase extraction (SPE) fractionation of wine with subsequent analysis of the metal content of each fraction by inductively coupled plasma – optical emission spectroscopy (ICP-OES).

Wine oxidation is a problem that affects the freshness, the aromatic profile, the colour and also the mouthfeel of the wine. It mainly concerns white wines. Oxygen interactions with wine compounds lead to the phenomena cited above that are responsible for the depreciation of these wines. Barrel aging is a crucial step in the wine process because it allows many modifications as wine enrichment, colour stabilization, clarification and also a slow oxygenation of the wine. Effects of the oak barrel have to be known to prevent oxidation of the wine. We have been interested in the main antioxidant compounds released by oak barrels to the wine and we have developed an innovative method to reach directly these antioxidant compounds at the oak stave surface.