Identification of S-3-(hexanal)-glutathione and its bisulfite adduct in grape juice from Vitis vinifera L. cv. Sauvignon blanc as new potential precursors of 3SH

Thibon, Cécile; Bocker, Caroline; Shinkaruk, Svitlana; Moine, Virginie; Darriet, Philippe; Dubourdieu, Denis

doi:10.1016/j.foodchem.2015.12.069

Cited by 39 publications

(71 citation statements)

References 36 publications

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“…Fractions of the last eluent were evaporated under reduced pressure to obtain GSH‐3MHAI as a white solid (40%). The 1 H NMR spectrum was in agreement with what was previously reported (Thibon et al ).…”

Section: Methodssupporting

confidence: 92%

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Thiol precursors in Catarratto Bianco Comune and Grillo grapes and effect of clarification conditions on the release of varietal thiols in wine

Fracassetti

Stuknytė

Rosa

et al. 2017

Australian Journal of Grape and Wine Research

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Background and Aims: Varietal thiols characterise the typical aroma of several white wines, such as Sauvignon Blanc. Their presence and sensory perception were suggested in two Sicilian grape cultivars, Catarratto Bianco Comune (CBC) and Grillo, though it has not been analytically proven. Methods and Results: Varietal thiol precursors and free varietal thiols were assessed in CBC and Grillo grapes, musts and wines by ultra-performance liquid chromatography/electrospray ionisation high-resolution MS. The isobaric compounds including S-3-(hexanal)-glutathione and S-3-(4-mercapto-4-methylpentan-2-one)-glutathione (GSH-4MMP) were distinguished by comparing their accurate masses and high-resolution-MS/MS spectra with those of their synthetic standards. S-3-(Hexanal)-glutathione, S-3-(hexan-1-ol)-glutathione and S-3-(hexan-1-ol)-cysteine were found in grape, must and wine, whereas GSH-4MMP and its hydrolysed forms were not found. Their concentration decreased during winemaking, mostly after grape pressing. We compared the effect of clarification conditions based on the exposure of must to either air or CO 2 on the concentration of thiol precursors and free thiols in wine; however, negligible differences were observed. The concentration of free thiols in the wines was found to be in the range 400-1100 ng/L and they were unaffected by the two clarification conditions tested. Conclusions: The isobaric S-3-(hexanal)-glutathione and GSH-4MMP were clearly distinguished for the first time by ultraperformance liquid chromatography/high-resolution MS through their retention times and MS spectra. These varietal thiols were revealed in CBC and Grillo wines for the first time. The air-free and air-exposed clarification treatments had little effect on the concentration of the varietal thiols. Significance of the Study: This study highlights the major impact of the varietal thiols (mainly 3-mercapto-hexan-1-ol and its acetate form) on the sensory properties of CBC and Grillo wines.

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Section: Methodssupporting

confidence: 92%

“…The free forms of varietal thiols are released along with the alcoholic fermentation by a Saccharomyces cerevisiae lyase (Tominaga et al 1998, Murat et al ). Recently, Thibon et al () identified S ‐3‐(hexan‐1‐al)‐glutathione (GSH‐3MHAl) in Sauvignon Blanc juice. This compound can be considered as a precursor of thiol aromas.…”

Section: Introductionmentioning

confidence: 99%

Thiol precursors in Catarratto Bianco Comune and Grillo grapes and effect of clarification conditions on the release of varietal thiols in wine

Fracassetti

Stuknytė

Rosa

et al. 2017

Australian Journal of Grape and Wine Research

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“…2); these compounds can be converted to 3SH during fermentation (requiring liberation of the aldehyde and enzymatic carbonyl reduction by yeast), albeit in low yield. [33] In addition, sulfonic acid derivatives of (E)-2-hexenal and mesityl oxide have recently been synthesised as proposed Bisulfite adducts of (a,b-unsaturated) carbonyls that act as prospective precursors to 3SH or 4MSP. Liberation of 3SH during fermentation has been shown for the GSH conjugate (via reversion to GSH-3SHal and enzymatic carbonyl reduction to yield the primary alcohol) but not for the adducts of (E)-2-hexenal or mesityl oxide.…”

Section: Analysis Of Varietal Thiols In Juice and Winementioning

confidence: 99%

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Jeffery¹

2016

Aust. J. Chem.

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Wine is an amazingly complex natural product that requires dedicated scientists to resolve many of its mysteries. Traditional synthetic organic chemistry and modern analytical techniques are powerful tools at the disposal of wine chemists who tackle the complexities of wine in order to improve scientific understanding and provide practical solutions to industry. Part of this quest for knowledge relates to maintaining or improving wine quality, which underpins consumer acceptance and links to the competitiveness of wineries in a global market. Wine aroma is an important aspect of wine quality and garners much attention from researchers. Grape-derived aroma compounds are one area of particular importance owing to their distinctiveness and ability to impart 'varietal aromas' to wines. Varietal thiols imparting tropical and citrus notes that are characteristic of wines such as Sauvignon Blanc have emerged, along with their grape-derived precursors, as an area of interest over the past two decades. These compounds have also caught our attention and we have made some important contributions to this field, including identifying new precursors, developing novel analytical methods, and conducting studies that provide unique insights into the biochemical transformations occurring in grape berries and juice, and during fermentation.

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“…Following studies also demonstrated that the combination of SO 2 and GSH involves a notable protective effect in wines [54]. Recent studies have shown that the addition of glutathione-rich dry inactivated yeast to grape juices modifies the white wine aroma influencing the concentrations of some volatile compounds and precursors with some benefits on its preservation [55][56][57]. The GSH amount of wine changes depending on the winemaking period.…”

Section: Chemical Treatments To Elaborate So 2 -Free Winesmentioning

confidence: 99%

Microbiological, Physical, and Chemical Procedures to Elaborate High-Quality SO2-Free Wines

Ferrer‐Gallego¹,

Puxeu²,

Martin³

et al. 2018

Grapes and Wines - Advances in Production, Processing, Analysis and Valorization

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Sulfur dioxide (SO 2 ) is the most preservative used in the wine industry and has been widely applied, as antioxidant and antibacterial agent. However, the use of sulfur dioxide implicates a range of adverse clinical effects. Therefore, the replacement of the SO 2 content in wines is one of the most important challenges for scientist and winemakers. This book chapter gives an overview regarding different microbiological, physical, and chemical alternatives to elaborate high-quality SO 2 -free wines. In the present chapter, original research articles as well as review articles and results obtained by the research group of the Wine Technology Center (VITEC) are shown. This study provides useful information related to this novel and healthy type of wines, highlighting the development of winemaking strategies and procedures.

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Identification of S-3-(hexanal)-glutathione and its bisulfite adduct in grape juice from Vitis vinifera L. cv. Sauvignon blanc as new potential precursors of 3SH

Cited by 39 publications

References 36 publications

Thiol precursors in Catarratto Bianco Comune and Grillo grapes and effect of clarification conditions on the release of varietal thiols in wine

Thiol precursors in Catarratto Bianco Comune and Grillo grapes and effect of clarification conditions on the release of varietal thiols in wine

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Microbiological, Physical, and Chemical Procedures to Elaborate High-Quality SO2-Free Wines

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