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…

Proteomic and activity characterization of exocellular laccases from three Botrytis cinerea strains

Botrytis cinerea is a fungus that causes common infection in grapes and other fruits. In winemaking, its presence can be both considered desirable in the case of noble rot infection or undesirable when grey rot is developed. This fungus produces an extracellular enzyme known as laccase which is able to cause oxidation of phenolic compounds present in must and wine, causing most of the times a decrease in its quality and problems during the winemaking process [1]. Material and methods: Three B. cinerea strains (B0510, VA612 and RM344) were selected and grown in a liquid medium adapted from one previously described [2]. The enzyme was isolated by tangential ultrafiltration of the culture medium using a QuixStand system equipped with a 30 KDa filtration membrane.

Supramolecular approaches to the study of the astringency elicited by wine phenolic compounds

The objective of this study is to review the scientific evidences and to advance into the knowledge of the molecular mechanisms of astringency. Astringency has been described as the drying, roughing and puckering sensation perceived when some food and beverages are tasted (1). The main, but possibly not the only, mechanism for the astringency is the precipitation of salivary proteins (2,3). Between phenolic compounds found in red wines, flavan-3-ols are the group usually related to the development of this sensation. Other compounds, phenolic or not, like anthocyanins, polysaccharides and mannoproteins could act modifying or modulating astringency perception by hindering the interaction between flavanols and salivary proteins either because of their interaction with the flavanols or because of their interaction with the salivary proteins.

Molecular cloning and characterization of UDP-glucose: furaneol glucosyltransferase gene from Japanese

2,5-Dimethyl-4-hydroxy-3(2H)-furanone (furaneol) is an important aroma compound in fruits, such as pineapple and strawberry, and is reported to contribute to the strawberry-like note in some wines. Several grapevine species are used in winemaking, and furaneol is one of the characteristic aroma compounds in wines made from American grape (Vitis labrusca) and its hybrid grape, similar to methyl anthranilate. Muscat Bailey A is a hybrid grape variety [V. labrusca (Bailey) x V. vinifera (Muscat Hamburg)], and its wine is one of the most popular in Japan. The inclusion of Muscat Bailey A in the ‘International List of Vine and Varieties and their Synonyms’ managed by the ‘International Organisation of Vine and Wine (OIV)’ in 2013 has further fueled its popularity among winemakers and researchers worldwide.

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.

Comparison of various storage conditions to preserve polyphenols in red-grape pomace

Red grape pomace, a waste from wine production, can be valorised by extracting polyphenols, high-added value compounds used in cosmetics or oenology. For use at an industrial level, using green extraction techniques, pomace need to be stored before being processed. The aim of this study is to test various storage conditions in order to maintain high level of polyphenols over 180 days, while keeping storage cost economically interesting. In a first step, different storage conditions (ambient temperature or cooled (4°C) temperature, anaerobic (saturation with N2) or aerobic conditions, and addition of sulphur dioxide (SO2)) were compared on small samples (1 kg) packed in plastic pockets. The quality of storage was assessed by following the optical density of the pomace extract at 280 nm (DO 280 expressed as mg/l eq gallic acid), which is an indication of the amount of remaining extractable polyphenols.