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…

Novel analytical technologies for wine fingerprinting in and beyond the laboratory

For characterization, sensory designing and authentication rapid analytical technologies have become available. Some, like Proton Transfer Reaction Mass Spectrometry allow a rapid spectrum of the volatile compounds of wines. Combined with chemometrics wines can be characterized. The same approach can be used to calculate the results of virtual mixtures and allow formulation of constant quality blends. Other new techniques and portable devices based on spectroscopy allow measurements on production sites and in grocery stores, even for the smart consumer. We will present some examples of the application of these techniques for authentication of wines, both in the laboratory and on site.

Bentonite fining in cold wines: prediction tests, reduced efficiency and possibilities to avoid additional fining treatments

Bentonite fining is widely used to prevent protein haze in white wines. Most wineries use laboratory-scale fining trials to define the appropriate amount of bentonite to be used in the cellar. Those pre-tests need to mimic as much as possible the industrial scale fining procedure to determine the exact amount of bentonite necessary for protein stability. Nevertheless it is frequent that, after fining with the recommended amount of bentonite, wines appear still unstable and need an additional fining treatment. It remains a major challenge to understand why the same wine, fined with the same dosage of the same bentonite, achieves stability in the lab, but not in the cellar.

Prevention of wine oxidation during barrel aging: an innovative method to measure antioxidant

Wine oxidation is a problem that affects the freshness, the aromatic profile, the colour and also the mouthfeel of the wine. It mainly concerns white wines. Oxygen interactions with wine compounds lead to the phenomena cited above that are responsible for the depreciation of these wines. Barrel aging is a crucial step in the wine process because it allows many modifications as wine enrichment, colour stabilization, clarification and also a slow oxygenation of the wine. Effects of the oak barrel have to be known to prevent oxidation of the wine. We have been interested in the main antioxidant compounds released by oak barrels to the wine and we have developed an innovative method to reach directly these antioxidant compounds at the oak stave surface.

Influence of SO2 and Zinc on the formation of volatile aldehydes during alcoholic fermentation

Laboratório de Análisis del Aroma y Enologia (LAAE). Department of Analytical Chemistry, Faculty of Sciences, Universidad de Zaragoza, 50009, Zaragoza, Spain, During alcoholic fermentation, fusel (or Strecker) aldehydes are intermediates in the amino acid catabolism to form fusel alcohols following the Ehrlich Pathway (1). One of the main enzymes involved in this pathway is Alcohol Dehydrogenase (ADH), whose activity is highly strain dependent and determines the rate of conversion of aldehydes into fusel alcohols (2). This enzyme has a Zn2+ catalytic binding site, which suggests that the must Zn2+ levels will most likely influence the rate of reduction of aldehydes into alcohols. On the other hand, SO2 is commonly used in winemaking for its antiseptic and antioxidant properties.

Determination of metallic elements in Chilean wines by atomic absorption spectroscopy and inductively coupled plasma–mass spectrometry

The chemical composition of wines depends on series of variables such as the type of grape, edaphoclimatic conditions, and viticulture and winemaking practices employed during production. Metallic elements play a significant role during winemaking (e.g. as catalysts of oxidation reactions) and have been previously employed for the classification of wines according to provenance. In this work, we focused on the analysis of metallic elements (K, Na, Ca, Zn, Cu, Fe, Mg, Mn, Ni, Cr, Al, Pb, Cd, Hg, Se, Co, Sn and As) in 145 Chilean wine samples (102 reds and 43 white wines), of seven grape varieties, and five of the major wine producing regions in Chile.