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…

Effect of mixed Torulaspora delbrueckii-Saccharomyces cerevisiae culture on rose quality wine

Alcoholic fermentation using no Saccharomyces wine is an effective means of modulating wine aroma. This study investigated the impact of coinoculating Torulaspora delbruecki with two Saccharomyces cerevisiae commercial yeast (QA23, Lallemand; Red Fruit, Sepsa-Enartis) on enological quality parameters, volatile composition and sensory analysis. The following assays were performed on Tempranillo variety: Saccharomyces QA23 (CTQA), Saccharomyces Red Fruit (CTRF), coinoculated T. delbrueckii + S.cerevisiae QA23 (CIQA) and coinoculated T. delbrueckii + S.cerevisiae (CIRF).

Impact of industrial-scale serial filtration on macromolecules in red wines

Filtration is a critical step in ensuring the clarity and microbial stability of wine prior to bottling. However the process of filtering potentially reduces red wine quality by removing some of the macromolecules that contribute to the texture of the wine. Commercial red wines, Cabernet Sauvignon (CAS) and Shiraz (SHZ), of two vintages and two grades (premium grade wines from the older vintage: CAS13 and SHZ13; and standard grade wines from a younger vintage: CAS14 and SHZ14) were filtered through industrial-scale commercial filtration units prior to bottling. Samples were taken before and after cross-flow filtration, lenticular filters, 0.65 µm and 0.45 µm pore size nylon membrane filters. The concentration and composition of macromolecules, including tannins and polysaccharides, were measured in all samples as well as particle size distribution and wine colour.

Effect of non-Saccharomyces yeast and lactic acid bacteria on selected sensory attributes and polyphenols of Syrah wines

Consumers predominantly use visual, aromatic and texture cues as quality/preference indicators to describe olfactory sensations. In this study, the effect of micro-organism in wine production was investigated using analytical and sensory techniques to achieve relevant analytical characterisation. Selected anthocyanins, flavan-3-ols, flavonols and phenolic acids were quantified in Syrah wines using RP-HPLC-DAD. Standard oenological parameters were also measured. Syrah grape must was fermented with various combinations of Saccharomyces cerevisiae (S. cerevisiae) and non-Saccharomyces (Metschnikowia pulcherrima or Hanseniaspora uvarum) yeasts, which was followed by sequential inoculation of lactic acid bacteria (LAB) (Oenococcus oeni or Lactobacillus plantarum).

Directed Evolution of Oenococcus oeni: optimising yeast-bacteria interactions for improved malolactic fermentation

Malolactic fermentation (MLF) is a secondary step in the vinification process and it follows alcoholic fermentation (AF) which is predominantly carried out by Saccharomyces cerevisiae. These two processes result in the degradation of metabolites to produce secondary metabolites which also contribute to the final wine flavour and quality. AF results in the production of ethanol and carbon dioxide from sugars and MLF stems from the degradation of L-malic acid (a dicarboxylic acid) to L-lactic acid (a monocarboxylic acid). The latter process results in a smoother texture as the acidity of the wine is reduced by the process, it also adds to the flavour complexity of the wine.

Using elicitors in different grape varieties. Effect over their phenolic composition

Phenolic compounds are very important in crop plants and have been the subject of a large number of studies. Three main reasons can be cited for optimizing the level of phenolic compounds in crop plants: their physiological role in plants, their technological significance for food processing, and their nutritional characteristics1 Indeed, an enormous diversity of phenolic antioxidants is found in fruits and vegetables, and their presence and roles can be affected or modified by several pre- and postharvest cultural practices and/or food processing technologies (Ruiz-García et al. 2012, Goldman et al. 1999, Tudela et al. 2002). In winegrapes, the technological importance of phenolic compounds, mainly flavonoids, is well-known.