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…

Analysis of off flavours in grapes infected with the fungal bunch rot pathogens, Aspergillus, Botrytis and Pencillium

Fungal bunch rots of grapes cause major losses to grape yield worldwide, yet the impact these moulds have on grape and wine quality is not well characterised. We sought to investigate the formation of unwanted volatile compounds of fungal origin in both synthetic grape juice culture media and in inoculated grape berries. Botrytis cinerea, Aspergillus niger, Aspergillus carbonarius, or Pencillium expansum were grown in synthetic grape juice medium and the culture homogenates analysed 4 and 7 days post inoculation. HS-SPME-GC-MS analysis of the culture homogenates 4 days post inoculation demonstrated that each of the fungi examined produced varying quantities of the mushroom or fungus-like aroma compounds, 1-Octen-3-ol, 1-Octen-3-one and 3-Octanone with A. carbonarius producing up to ten times the amounts of all three metabolites per mg of dry mycelium.

Fining-Derived Allergens in Wine: from Detection to Quantification

Since 2012, EU Commission approved compulsory labeling of wines treated with allergenic additives or processing aids “if their presence can be detected in the final product” (EU Commission Implementing Regulation No. 579/2012 of 29 June 2012). The list of potential allergens to be indicated on wine labels comprises sulphur dioxide and milk- and egg- derived fining agents, including hen egg lysozyme, which is usually added in wines as preservative. In some non-EU countries, the list includes gluten, tree nuts and fish gelatins. With the exception of lysozyme, all these fining proteins were long thought to be totally removed by subsequent winemaking processings (e.g. bentonite addition).

Impact of non-fruity compounds on red wines fruity aromatic expression: the role of higher alcohols

A part, at least, of the fruity aroma of red wines is the consequence of perceptive interactions between various aromatic compounds, particularly ethyl esters and acetates, which may contribute to the perception of fruity aromas, specifically thanks to synergistic effects.1,2 The question of the indirect impact of non-fruity compounds on this particular aromatic expression has not yet been widely investigated. Among these compounds higher alcohols (HA) represent the main group, from a quantitative standpoint, of volatiles in many alcoholic beverages. Moreover, some bibliographic data suggested their contribution to the aromatic complexity by either increasing or masking flavors of wine, depending of their concentrations.

Application of high power ultrasounds during red wine vinification

Wine color is one of the main organoleptic characteristics influencing its quality. It is of especial interest in red vinifications due to the economic resources that wineries have to invest for the extraction of the phenolic compounds responsible of wine color, compounds that are mainly located inside the skin cell vacuoles. Moreover, these phenolic compounds not only influence color but also other organoleptic properties such as body, mouthfeel, astringency and flavour. The transference of phenolic compounds from grapes to must during vinification is closely related with the type of grapes and the winemaking technique.

Impact of some agronomic practices on grape skins anthocyanin content

Wine colour is the first quality characteristic to be assessed, especially regarding red wines. Anthocyanins are very well known to be the main responsible compounds for red wine colour. Red cultivars can synthesize and accumulate anthocyanins in berry skin to express their colour. However, anthocyanin accumulation is often influenced by a series of factors, such as genetic regulation, phytohormones, environmental conditions and viticultural management.