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

During red wine ageing or conservation, color and taste change and astringency tends to reduce. These changes result from reactions of flavan-3-ols and/or anthocyanins among which condensation reactions with acetaldehyde are particularly important. The full characterization of these reactions has not been fully achieved because of difficulties in extracting and separating the newly formed compounds directly from wine. Model solutions mimicking food products constitute a simplified medium for their exploration, allowing the detection of the newly formed compounds, their isolation, and their structure elucidation.

Fining is a technique that is used to remove unwanted wine components that affect clarification, astringency, color, bitterness, and aroma. Fining involves the addition of adsorptive or reactive material in order to reduce or eliminate the presence of certain less desirable wine components and to ensure that a wine remains in a particular stable state for a given period of time Recently concerns have been raised about the addition of animal proteins, such as gelatin, to wine due to the disease known as bovine spongiform encephalopathy (Mad Cow disease). Although the origin of gelatins has been moved to porcine, winemakers are asking for substitute products with properties and application protocols similar to the traditional animal-derived ones, making the use of plant-derived proteins in fining a practically viable possibility. As a consequence, various fining agents derived from plants have been proposed, including proteins from cereals, legumes, and potato.

Winemaking decisions and techniques are known to affect the final aromatic composition of red wines. Winemakers put a constant effort into the improved controlling of vinification procedures to achieve better quality. Anyway an increased customer’s demand for uniqueness is often forcing them to adjust and offer new and new interesting products. To support the producers, an improved knowledge on aromatic potential as affected by classical and alternative strategies is needed.

Flavonols are a class of flavonoid compounds derived from plant secondary metabolism. There they play different roles like antioxidants, internal regulators and UV screenings. In red wines, flavonols have increasingly received consideration by part of scientific and winemakers according their properties began to arise known. Among these stand out wine colour stabilization and their value as bioactive compounds. In this work the complete series of the acetylated and p-coumaroylated derivatives of the 3-O-glycosides of methoxylated flavonols, namely isorhamnetin, laricitrin and syringetin, have been identified in grapes and their respective wines from Vitis vinifera cv. Tannat.

From the standpoint of wine aroma oxidation there are two effects observed: aroma degradation of oxygen sensitive compounds (polyfunctional mercaptans) and the appearance of new substances with high aromatic power (acetaldehyde, methional, phenylacetaldehyde, sotolon, alkenals, isobutanal and 2, 3-metylbutanals) (1-5). According to our experience, Strecker aldehydes are compounds with highest sensory relevance in the oxidative degradation of many wines (5-7).