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…

Application to the wine sector of European Convention on the landscapes

The landscape is defined by the European convention of the landscape (Florence, October 20, 2000) like part of the territory as perceived by the populations, whose character results from the action of natural and/or human factors and their interrelationships. This convention is based on the contribution cultural, ecological, environmental, social of the landscapes and aims at a reinforcement of the tools of protection and valorization in particular in the agricultural policies, of regional planning and town planning. Moreover, it encourages a step of identification and qualification of the landscapes and underlines the need for developing the sensitizing and the training of the actors concerned.

Il vino nobile di Montepulciano

C’è grande attenzione al rapporto tra zonazione e marketing. Mi sembra però che ci sia anco­ra oggi un salto fra le pratiche di analisi del terreno e di deterrninazione di quello che potremo definire “cru” e quello che può essere la sua utilizzazione rispetto ai consumatori finali.

Study of fungal and bacterial laccases for the reduction of ochratoxin A content in model wine

Ochratoxin A (OTA) is a mycotoxin produced by several filamentous fungi infecting grape bunches (Penicillium and Aspergillus spp.), this toxin pass to must when grapes are crushed and later it is found in wine. Following the evaluations of the toxicity of OTA, European Commission Regulations have been promulgated introducing upper limits for OTA concentrations in various commodities (cereals, cereal products, dried vine fruit, coffee, wine, grape juice, baby foods and dietary foods for special medical purposes).

Grapevine responses to Botrytis cinerea infection: noble rot versus grey rot

The intricate relationship between the necrotrophic pathogen Botrytis cinerea and grape berries (Vitis vinifera spp.) can lead to the development of either the desirable noble rot (NR) or the unfavourable grey rot (GR), depending on the prevailing weather conditions.

Lead levels in fortified wines

AIM The main lead exposure route is the intake of contaminated food, water, and alcoholic beverages, in particular wine. At the gastric level, Pb is transformed into a soluble compound which, when conveyed into the bloodstream, is the long-term cause of saturnism, intoxication with neurotoxic, nephrotoxic and hematopoietic effects, and with the neurological developmental delay of children. Pb is classified by the International Agency for Research on Cancer as a 2A class, possible carcinogenic to humans. In an opinion on possible health risks, CONTAM considered that cereals, vegetables, drinking water, and wine give a greater contribute to dietary exposure to Pb in Europe. Large quantities of wine, beer, and other alcoholic products drinking can increase daily Pb intake above the maximum permitted levels.