Characterization of various groups of pyranoanthocyanins in Merlot red wine

(-)-Rotundone, an oxygenated sesquiterpene, is a potent odorant molecule with a characteristic spicy aroma existing in various plants including grapes1. It is considered as a significant compound notably in wines and grapes because of its low sensory threshold (16 ng L-1 in red wine, 8 ng L-1 in water) and aroma properties. (-)-Rotundone was first identified in red wine made from the grape cultivar Syrah (regionally called Shiraz) in Australia1, and then it was found in several grape varieties such as Duras, Grüner Veltliner, Schioppettino and Vespolina from Europe2, 3. Several environmental factors affecting the accumulation of (-)-Rotundone during the grape maturation, were reported such as ambient temperature4, soil properties and topography5, soil moisture from irrigation and light exposure in the bunch zone by leaf removal2.

The occurrence of faults and taints in wine, such as those caused by microbial spoilage or various taints, have resulted in significant financial losses to wine producers. The wine industry commits significant financial resources towards fining and taint removal processes each year. Fining involves the addition of one or more adsorptive substrates to juice or wine to bind certain components, thus reducing their concentration [1]. However, these processes are often not selective and can also remove desirable flavour and aroma compounds.

All along the winemaking process, conditioning and aging, wine is susceptible to be contaminated by different molecules. Contaminations can have various origins, related to wine microorganisms or as a result of an exogenous contamination. The aforementioned contamination of the wine can be caused by the migration of molecules from the materials in contact with the wine or by a contamination from exogenous molecules present in the air. Regardless of the source of the contamination, mainly two types of consequences can be observed.

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.

Tyrosol (TYR) and hydroxytyrosol (HYT) are bioactive phenols present in olive oil and wine, basic elements of the Mediterranean diet. TYR is reported in the literature for its interesting antioxidant, cardioprotective and anti-inflammatory properties. In wine, its concentration can reach values as high as about 40 mg/L
[Pour Nikfardjam et al. 2007] but, more frequently, this phenol – derived from yeast metabolism of tyrosine during fermentation – is present at lower levels, generally higher in red wines compared to whites. HYT was measured for the first time by Di Tommaso et al. [1998] in Italian wines – with maximum values of 4.20 mg/L and 1.92 mg/L for red and white wines, respectively – while definitely lower concentrations have been found later in Greek samples.