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…

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.

Fractionation of copper and iron in wine: Assessment of potential macromolecule and sulfur binding agents

Copper and iron are known to substantially impact wine stability through oxidative, reductive or colloidal phenomena. However, the binding of metal ions to different wine components under wine conditions, and the impact of this binding on the ability of the metal ions to induce spoilage processes, is not well understood. This study surveyed a range of red and white wines for an understanding of the variability of broad metal categories within the wines. The techniques utilized included an electrochemical constant current stripping potentiometry technique (ccSP), and solid phase extraction (SPE) fractionation of wine with subsequent analysis of the metal content of each fraction by inductively coupled plasma – optical emission spectroscopy (ICP-OES).

Sensory impacts of the obturator used for the Chasselas: study over the time

Many parameters affect the organoleptic characteristics of wine: internal parameters like the chemical composition or polyphenol content and external as for example storage conditions or the type of obturator. The aim of this study was to characterize sensorally the impacts of several type of obturator on a white wine: Chasselas. To determine the organoleptic characteristics of this wine, a quantitative descriptive analysis could be used. But rapid sensory methods were preferred in this project. Indeed these methods are an appropriate alternative to conventional descriptive methods for quickly assessing sensory product discrimination.

Comparison of aroma-related compounds of carbonic maceration and traditional young red winemaking in case of Merlot by means of targeted metabolomic approach

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.

Pesticide removal in wine with a physical treatment by molecular sieving

All along the winemaking process, conditioning and aging, wine is susceptible to be contaminated by different molecules. Contaminations can have various origins, related to wine microorganisms or as a result of an exogenous contamination. The aforementioned contamination of the wine can be caused by the migration of molecules from the materials in contact with the wine or by a contamination from exogenous molecules present in the air. Regardless of the source of the contamination, mainly two types of consequences can be observed.