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…

Identifying best parameters to characterize genotypes capability of retaining adequate malic acid at harvest and in final wines

Under current climate change pressures, obtaining grapes with adequate acidity at harvest is one of the main challenges for growers, especially if the goal is producing sparkling wines. This issue arises from two main occurrences: i) higher temperatures enhance degradation of malic acid; ii) grape maturity may occur under suboptimal climatic conditions due to an advanced phenology.

The chances for using non-saccharomyces wine yeasts for a sustainable winemaking

Climate changes and the trend towards organic and more sustainable winemaking highlighted the need to use biological methodologies. The reduction in the use of SO2, the need of the reduction of ethanol content of wines and the now need to reduce or eliminate chemical phytosanitary products, have prompted the search for alternative practices.

Marketing terroir wines

The markets for quality wine are becoming more competitive as newer producers emerge and traditional producers improve their quality. The concept of terroir is one way to differenzi­ate wines in a competitive market and to enhance producer income.

Organic mulches improve vine vigour, yield and physiological response in a semi-arid region

Recycled organic mulch within the row in vineyard floor management has become an interesting ecological strategy to adapt the crop to climate change consequences in semi-arid regions.
This study aimed to assess the impact of three recycled organic mulches [straw (STR), grape pruning debris (GPD), and spent mushroom compost (SMC)] and two conventional soil management practices [herbicide (HERB) and under-row tillage (TILL)] on vegetative vigour (NDVI), production (kg/plant), and physiological parameters (δ13C in grapes and leaf gas exchange during four grapevine phenology stages). Additionally, temperature and water soil parameters were collected at three soil depths. Data was collected during the 2021 and 2022 grapevine growing seasons in La Rioja, Spain.

Protein extracts of the Andean pseudocereals quinoa and kiwicha as alternatives for the fining of wine phenolics.

INTRODUCTION: Lately, there has been an increasing interest in using plant-derived proteins for wine phenolic fining.