Flavanol glycosides in grapes and wines : the key missing molecular intermediates in condensed tannin biosynthesis ?

In red wines, anthocyanins evolve during the wine-making process and ageing. They react with other compounds (such as vinylphenols, acetaldehyde, pyruvic acid…) to form a stable family of compounds called pyranoanthocyanins. Furthermore, the oxidation process can modify the anthocyanic profile of a red wine. It is also interesting to evaluate the occurrence of the different subclasses of pyranoanthocyanins and to characterize their chemical properties. The first objective of this study is to evaluate the occurrence of the different groups of pyranoanthocyanins in an oxidised Merlot wine by a centrifugal partition chromatography strategy. The second goal is to evaluate their relative impact in red wines from Bordeaux region by measuring their concentrations.

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.

Commercial oenological tannins (TECs) are widely used in the wine industry. TECs are rich in condensed tannins, hydrolyzable tannins or a mixture of both. Wine grapes are a important source of proanthocyanidins or condensed tannins while oak wood possess a high concentration of hydrolyzable tannins (Obreque-Slier et al., 2009). TECs contribute with the antioxidant capacity of wine, catalyze oxide-reduction reactions and participate in the removal of sulfur compounds and metals.

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.

Lately several works highlighted the capacity of grape cell-wall material (CWM) to interact with proanthocyanidins (PA), indicating its potential use as fining agent for red wines.1–4 However, those studies were performed by using purified PAs and very high doses of CWM (almost ten-fold higher than those used in wine industry for other commercial fining agents). The present study focuses on the applicability of CWM from Cabernet sauvignon pomace as fining agent for red wines under real winery conditions. Grapes of cultivar Cabernet sauvignon were harvested at three different maturity levels
(unripe, mature, and overripe) and used for red winemaking. The pomace of such vinifications were used as source of CWM, and applied into red wines at two different concentrations: 0.2 g/L and 2.5 g/L.