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…

Correlations between sensory characteristics and colloidal content in dry white wines

Must clarification is an important step occurring just after grape extraction in the elaboration of white wine, consisting in a solid-liquid separation. Traditionally, low must turbidity, around 50-150 NTU, is generally reached in white winemaking in order to prevent reductive aromas and facilitating alcoholic fermentation. Alternatively, a higher turbidity (300 NTU or above) can be sought for reasons such as a better expression of grapes identity (terroir), or for getting a must matrix that could supposedly lead to wines having greater ageing potential.

Technological possibilities of grape marc cell walls as wine fining agent. Effect on wine phenolic composition

Fining is a technique that is used to remove unwanted wine components that affect clarification, astringency, color, bitterness, and aroma. Fining involves the addition of adsorptive or reactive material in order to reduce or eliminate the presence of certain less desirable wine components and to ensure that a wine remains in a particular stable state for a given period of time Recently concerns have been raised about the addition of animal proteins, such as gelatin, to wine due to the disease known as bovine spongiform encephalopathy (Mad Cow disease). Although the origin of gelatins has been moved to porcine, winemakers are asking for substitute products with properties and application protocols similar to the traditional animal-derived ones, making the use of plant-derived proteins in fining a practically viable possibility. As a consequence, various fining agents derived from plants have been proposed, including proteins from cereals, legumes, and potato.

Dissecting the polysaccharide‐rich grape cell wall matrix during the red winemaking process, using high‐throughput and fractionation methods

Limited information is available on grape wall-derived polymeric structure/composition and how this changes during fermentation. Commercial winemaking operations use enzymes that target the polysaccharide-rich polymers of the cell walls of grape tissues to clarify musts and extract pigments during the fermentations. In this study we have assessed changes in polysaccharide composition/ turnover throughout the winemaking process by applying recently developed cell wall profiling approaches to both wine and pomace polysaccharides. The methods included gas chromatography for monosaccharide composition (GC-MS), infra-red (IR) spectroscopy and comprehensive microarray polymer profiling
(CoMPP) using cell wall probes.

Metabolomics comparison of non-Saccharomyces yeasts in Sauvignon blanc and Shiraz

Saccharomyces cerevisiae (SC) is the main driver of alcoholic fermentation however, in wine, non-Saccharomyces species can have a powerful effect on aroma and flavor formation. This study aimed to compare untargeted volatile compound profiles from SPME-GC×GC-TOF-MS of Sauvignon blanc and Shiraz wine inoculated with six different non-Saccharomyces yeasts followed by SC. Torulaspora delbrueckii (TD), Lachancea thermotolerans (LT), Pichia kluyveri (PK) and Metschnikowia pulcherrima (MP) were commercial starter strains, while Candida zemplinina (CZ) and Kazachstania aerobia (KA), were isolated from wine grape environments. Each fermentation produced a distinct chemical profile that was unique for both grape musts. The SC-monoculture and CZ-SC sequential fermentations were the most distinctly different in the Sauvignon blanc while the LT-SC sequential fermentations were the most different from the control in the Shiraz fermentations.

Interactions of wine polyphenols with dead or living Saccharomyces cerevisiae Yeast Cells and Cell Walls: polyphenol location by microscopy

Tannin, anthocyanins and their reaction products play a major role in the quality of red wines. They contribute to their sensory characteristics, particularly colour and astringency. Grape tannins and anthocyanins are extracted during red wine fermentation. However, their concentration and composition change over time, due to their strong chemical reactivity1. It is also well known that yeasts influence the wine phenolic content, either through the release of metabolites involved in the formation of derived pigments1, or through polyphenol adsorption2,3.