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…

Influence of cork density upon cork stopper resiliency after opening a sparkling wine bottle

After Champagne popping, the first consumer’s observation is the shape of the cork stopper. Consumers expect a “mushroom shape”. Nevertheless, we sometimes observe a “barrel” shape due to inappropriate cork’s elastic properties. The aim of this study was to follow the loss of cork stopper resiliency during 26 months according to the density (d) of the cork in contact with the wine. 1680 disks were weighed + measured and divided in 6 density classes: High (H1 d= 0,19 g/cm3 – H2 d= 0,21 g/cm3), Medium (M, not studied) and Low (L1 d= 0,13 g/cm3 – L2 d= 0,14 g/cm3). Then, 138 technical cork stoppers were produced for each of the 4 studied groups. These corks consisted of an agglomerated natural cork granule body to which two natural cork disks were glued. A total of 552 bottles of sparkling wine were closed with these corks and open after 13, 19 and 26 months to follow cork resiliencies. Wine bottles were stored horizontally; thus, the external natural cork disks were in contact to the wine. During the 26 months of the study, highly significant differences (ANOVA) were observed between the resiliencies of H-corks and those of L-corks, whatever the time studied. The diameters of the L-corks were statistically higher than those of the H-corks. No significant differences were observed between L1 and L2 corks. At the opposite, differences were noted between H1 and H2 at 19 and 26 months. This could be explained by the heterogeneity of the resiliency that was higher for H-corks than for L-corks. Finally, the corks were visually (12 judges) divided in 3 classes corresponding to high (expected mushroom shape, i.e high resiliency), medium (irregular shape of the disk in contact with the wine and/or low premature deterioration of the expected resiliency) and low qualities (barrel shape = premature deterioration of the resiliency). The corks were also divided in 3 categories corresponding to 0-33%, 34-66% and 67-100% resiliency. A strong correlation was noted between the visual and the instrumental categorizations. This study strongly evidenced 1) the importance of the cork density on the cork stopper behaviour when opening the bottle and 2) the interest of an instrumental approach reflecting the consumer’s perception.

Postharvest elicitors and metabolic changes in wine grape berries

Wine grape berries respond to postharvest treatments with specific gaseous elicitors in terms of metabolic changes and composition. Short-term (3 days) high (30 KPa) CO2 treatment affects phenol compound concentration in skins of ‘Trebbiano toscano’ berries.

Terracing in steep slope viticulture and its potential to promote biodiversity in vineyard ecosystems

Viticulture on steep slopes has shaped exceptionally species-rich cultural landscapes in Germany.

Wine archeochemistry: a multiplatform analytical approach to chemically profile shipwreck wines

The Cape of Storms (also known as Cape of Good Hope) is renowned for harbouring a multitude of shipwrecks due to the inherent treacherous coastline and blistering storms.

Impact of oenological tannins on microvinifications affected by downy mildew

AIM: Vine diseases are still responsible for economic losses. Previous study in our laboratory, have shown effects of oenological tannins against Botrytis cinerea1,2. According to this, the aim was to evaluate the wine protection by oenological tannins against an another disease, the downy mildew. METHODS: During the 2020 vintage, infected grapes by downy mildew (Vitis vinifera cv. Merlot) were collected from the dispositive ResIntBio. The 100 kg were crushed, destemmed and dispatch into 10 aluminium tanks. SO2 was added at 3 g/hL. Oenological tannins (grape, quebracho, ellagitannin or gallotannin) were added at 100 g/hL into eight different tanks (4×2 tanks). The two last tanks were considered as control without addition of oenological tannins. Alcoholic fermentation was achieved with Actiflore 33® at 20 g/hL. Malolactic fermentation was achieved with Lactoenos B7at 1 g/hL. Finished wines were sulfited to obtain 45 mg/L of total SO2.