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…

Beyond colors of rosé wines: impact of origin and winemaking technology on their color, polyphenol and thiol compositions

Rosé wine consumption is rapidly increasing with its market share in France that has grown from 11 % to 32 % in less than 20 years. A recent trend is also to produce rosé wines with lighter colors. Varieties, terroir and technology certainly have an influence on rosé wine colors.

Regenerative agricultural winegrowing systems play a role in refining the expression of terroir in the pacific coast region of United States and Canada

By definition, Regenerative Agricultural Systems seek to promote soil and plant health by using photosynthesis for the removal and retention of atmospheric carbon dioxide into stable soil carbon.

Effect of the commercial inoculum of arbuscular mycorrhiza in the establishment of a commercial vineyard of the cultivar “Manto negro

The favorable effect of symbiosis with arbuscular mycorrhizal fungi (AMF) has been known and studied since the 60s. Nowadays, many companies took the chance to start promoting and selling commercial inoculants of AMF, in order to be used as biofertilizers and encourage sustainable biological agriculture. However, the positive effect of these commercial biofertilizers on plant growth is not always demonstrated, especially under field conditions. In this study, we used a commercial inoculum on newly planted grapevines of a local cultivar grafted on a common rootstock R110. We followed the physiological status of vines, growth and productivity and functional biodiversity of soil bacteria during the first and second years of 20 inoculated with commercial inoculum bases on Rhizophagus irregularis and Funeliformis mosseaeAMF at field planting time and 20 non-inoculated control plants. All the parameters measured showed a neutral to negative effect on plant growth and production. The inoculated plants always presented lower values of photosynthesis, growth and grape production, although in some cases the differences did not reach statistical significance. On the contrary, the inoculation supposed an increase of the bacterial functional diversity, although the differences were not statistically significant either. Several studies show that the effect of inoculation with AMF is context-dependent. The non-favorable effects are probably due to inoculation ineffectiveness under complex field conditions and/or that, under certain conditions, AMF presence may be a parasitic association. This puts into question the effectiveness of its application in the field. Therefore, it is recommended to only resort to this type of biofertilizer when the cultivation conditions require it (e.g., very low previous microbial diversity, foreseeable stress due to drought, salinity, or lack of nutrients) and not as a general fertilization practice.

EVALUATING WINEMAKING APPLICATIONS OF ULTRAFILTRATION TECHNOLOGY

Ultrafiltration is a process that fractionates mixtures using semipermeable membranes, primarily on the basis of molecular weight. Depending on the nominal molecular weight cut-off (MWCO) specifications of the membrane, smaller molecules pass through the membrane into the ‘permeate’, while larger molecules are retained and concentrated in the ‘retentate’. This study investigated applications of ultrafiltration technology for enhanced wine quality and profitability. The key objective was to establish to what extent ultrafiltration could be used to manage phenolic compounds (associated with astringency or bitterness) and proteins (associated with haze formation) in white wine.

Influenza di alcuni aspetti ambientali sul contenuto di stilbeni nel vino nell’area della DOC “Sangiovese di Romagna” (Italia)

The ambition of the zonation of the Doc “Sangiovese di Romagna” is described as 25 siti sperimentali, aventi diversa origine geologica, in cui è stato individuato un vigneto omogeneo per la determinazione dei principali parametri viticoli ed enologici. In seguito è stato analizzato il contentto di stilbeni nei vini al fine di indepth il legame con le charatteristiche geopedologiche. The studio describes the positive relationship between the altitude and the content of the trans -piceide nelle province di Forlì and Ravenna and of the trans -resveratrolo a Ravenna. I suoli con maggiore calcare attivo hanno fornito vini più ricchi in stilbeni.