Macrowine 2021
IVES 9 IVES Conference Series 9 New acylated flavonols identified in the grape skin of Vitis vinifera cv. Tannat and their wines

New acylated flavonols identified in the grape skin of Vitis vinifera cv. Tannat and their wines

Abstract

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. The assignments were based on their UV-vis and MSn spectral data. Firstly, the MS2 fragmentation pattern of each tentatively identified flavonol glycoside derivative showed a main signal attributable to the expected flavonol aglycone, together with a weak signal corresponding to the intermediate loss of the acyl moiety. The structures of the flavonol aglycones were confirmed by their respective MS3 experiments that matched with those obtained from authentic standards of the three aglycones. In addition, the DAD on-line UV-vis spectra of the suggested flavonol-3-O-(p-coumaroyl)-glucosides closely matched the sum of the respective spectra of the flavonol-3-O-glucoside and that of p-coumaric acid. Interestingly, the presence of these new flavonol derivatives was limited to the minority flavonols. Being acylation a final step in the flavonoid synthesis, our findings suggest a very high specificity of the acyltransferases implied for the flavonol glycoside substrate that in this case would be related to the presence of methoxyl groups in the B ring of the flavonol. The fact that these compounds have been found in Tannat, a Vitis vinifera with scarce cultivation around the world, may indicate that the implied acyltransferases could be little spread among grape varieties. Nevertheless it could be associated to other factors like growth environmental conditions, or to the sensitivity of the analytical technique employed, or others factors, which should be further considered and studied. These results give evidences of new flavonol derivatives in grapes and wines, and expose a case of substrate specificity of the enzymes implied in their synthesis.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Poster

Authors

Isidro Hermosín-Gutíerrez*, Diego Piccardo, Gustavo González Neves, Guzmán Favre, Sergio Gómez-Alonso

*Universidad de Castilla-La Mancha

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Sensory definition of green aroma concept in red French wines. Evidence for the contribution of novel volatile markers

The aromatic complexity of a wine results from the perception of the association of volatile molecules and each aroma can be categorized into different families. The “green” aromas family in red wines has retained our attention by its close link with the fruity perception. In that study, the “green” olfactory concept of red wines was considered through a strategy combining both sensory analysis and hyphenated chromatographic techniques including HPLC and MDGC (Multidimensional Gas Chromatography). The aromatic space of this concept was specified by lexical generation through a free association task on 22 selected wines by a panel of wine experts. Then, 70 French red wines were scored on the basis of the intensity of their “green” and “fruity” attributes.

Monitoring of Pesticide Residues from Vine to Wine

Those previous years, pesticides are often brought to the forefront by media. Questions arose about their toxicity for growers and consumers. Even if a downward trend is underway, the use of pesticides is required to ensure steady quality and quantity of harvests. A large number of active ingredients are authorized but regarding viticulture, mainly insecticides and fungicides are applied, to control pests and diseases and to increase crop yield. Some phytosanitary products, principally fungicides, applied close to the harvest date may frequently be detected in wines.

Petrolomics-derived data interpretation to study acetaldehyde-epicatechin condensation reactions

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.

Grape metabolites, aroma precursors and the complexities of wine flavour

A critical aspect of wine quality from a consumer perspective is the overall impression of wine flavour, which is formed by the interplay of volatile aroma compounds, their precursors, and taste and matrix components. Grapes contribute some potent aroma compounds, together with a large pool of non-volatile precursors (e.g. glycoconjugates and amino acid conjugates). Aroma precursors can break down through chemical hydrolysis reactions, or through the action of yeast or enzymes, significantly changing the aroma profile of a wine during winemaking and storage. In addition, glycoconjugates of monoterpenes, norisoprenoids and volatile phenols, together with sulfur-conjugates in wine, provide a reservoir of additional flavour through the in-mouth release of volatiles which may be perceived retro-nasally.

The effect of Nitrogen and Sulphur foliar applications in hot climates

ine nitrogen deficiency can negatively influence the aroma profile and ageing potential of white wines. Canopy management can alter vine microclimate, affect the nitrogen availability and influence the response of leaf senescence. Increasing the nitrogen availability to vines can increase the Yeast Assimilable Nitrogen (YAN) levels in harvested fruit and wine. Studies show that foliar nitrogen and sulphur applications at véraison, on low YAN Sauvignon blanc grapes have an effect on the level of amino acids (Jreij et al. 2009) and on S-containing compounds such as glutathione and thiols (Lacroux et al. 2008), which in turn can influence the formation of major volatiles and the aroma profile of the wine.