IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 New insights on thiol precursors catabolism by yeast during wine fermentation: identification of the N-Acetyl-L-Cysteine conjugate

New insights on thiol precursors catabolism by yeast during wine fermentation: identification of the N-Acetyl-L-Cysteine conjugate

Abstract

Understanding the catabolism of thiol precursors is essential for understanding the revelation of varietal thiols in wine. For many years, knowledge of these precursors has been limited to the S-conjugates of glutathione, cysteine (Cys3SH) and the dipeptides g-GluCys and CysGly, without being able to explain the full origin of 3-sulfanylhexan-1-ol (3SH) in wines. Cysteine was the one considered as the final intermediate before the revelation of 3SH by yeast. Inspired by the glutathione detoxification pathway of xenobiotics, we identified the 3-S-(N-Acetyl-Cysteinyl)hexan-1-ol (NAC3SH) as a new metabolite, by developing (a) a dedicated organic synthesis strategy, (b) a targeted LC-MS/MS analysis method and (c) filiation studies under oenological conditions.In practice, we synthesized NAC3SH by Michael addition of N-Acetyl-L-Cysteine onto trans-2-hexenal in 50/50 water/acetonitrile followed by reduction with NaBH4 in situ. After purification by preparative HPLC, the two diastereomers of NAC3SH were successfully isolated. Characterization was done by both 1D and 2D homonuclear 1H and heteronuclear 1H /13C NMR spectroscopy and quantification by 1D 1H NMR (qNMR). An analytical method for NAC3SH was developed by LC-MS/MS using Cys3SH-d2 as internal standard. The resolution of the two diastereomers could not be achieved under our conditions and they were therefore analyzed in 50/50 equimolar mixture. The method has been validated and showed very satisfactory analytical performances (accuracy = 102%, linearity: R2 = 0.976, LOQ = 6.9 µg/L, LOD = 23 µg/L, repeatability: CV).

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Dournes Gabriel¹, Sachot Somaya¹, Le-Guernevé Christine¹, Suc Lucas1, Mouret Jean-Roch¹ and Roland Aurélie¹  

¹SPO, Univ Montpellier, INRAE, Institut Agro, Montpellier, France

Contact the author

Keywords

thiol precursors, varietal thiol, grape, wine

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

GC-O and olfactoscan approaches to reveal premature aging markers in Chardonnay wine

Molecular markers of wine oxydation, such as sotolon or Strecker’s aldehydes that induce respectively nut or curry and boiled vegetables or wilted rose odors, can be percieved as a default by consumers. These volatile compounds are especially formed during the premature aging of wine, but it is likely that several contributing compounds are still unknown as is their combined contribution. This study was carried out to identify the markers of oxydation in Chardonnay wine by Gas Chromatography Olfactometry (GC-O) and to study the impact of these markers on the complex wine aromatic buffer using the Olfactoscan approach.A Chardonnay wine (2018-vintage), taken after malolactic fermentation without sulphites addition, was submitted to an artificial oxidation to simulate more or less prononced premature oxidation. Volatile compounds were extracted by Solid-Phase Extraction (SPE) and analysed by GC-O with a panel of 13 trained subjects. The same extract was also submitted to a second analysis based on the Olfactoscan technique, which allowed to evaluate the impact of each volatile compounds on the complex aromatic buffer of a non-oxidized wine delivered as background odor. Preliminary results revealed three types of behavior. On the one hand, several odor zones appeared only with the background odour, suggesting a synergy effect induced by the compounds in the aromatic buffer. Conversely, odor-active compounds could not be perceived within the background odor suggesting a masking effect. Finally several compounds were found to contribute as key odorants for wine oxydation once mixed with the aromatic buffer. These compounds are still to be identified using complementary techniques.

The Soil Component of Terroir

Evidence for a specific effect of soil mineral composition on wine character is largely anecdotal. However, soil potassium supply to the vine must be properly balanced between deficiency and excess for good fruit quality.

Le Pinot noir dans la zone AOC des “Colli Orientali del Friuli” (nord-est de l’Italie) : influence de la forme de taille sur les paramètres viticoles et œnologiques du raisin et du vin

Pinot noir is an interesting vat variety for the high quality products it provides in the most suitable areas. In France, the most important Pinot Noir growing areas are Burgundy, Champagne, Alsace and the Loire. In Italy, Pinot Noir is grown almost exclusively in the northern regions of Trentino-Alto Adige, Lombardy and Friuli-Venezia Giulia.

Nitrogen requirements of table grape cultivars grown in the san Joaquin valley of California

Ground water in the interior valleys of California is contaminated with nitrates derived from agricultural activities, primarily the over-fertilization of crops.

WHICH IMPACT FOR PROANTHOCYANIDIC TANNINS ON RED WINE FRUITY AROMA? SENSORY AND PHYSICOCHEMICAL APPROACHES

Previous research on the fruity character of red wines highlighted the role of esters. Literature provides evidence that, besides these esters, other compounds that are not necessarily volatiles may have an important impact on the overall aroma of wine, contributing to a modulation of its global aromatic expression. The goal of this work was to assess the olfactory consequences of a mixture between esters and proanthocyanidic tannins, through sensory and physico-chemical approaches.
Sensory analysis of numerous aromatic reconstitutions, including triangular tests, detection thresholds, and sensory profiles, were conducted in order to evaluate the sensory impact of tannins on red wine esters perception.