Identification and quantification by LC–MS/MS of a new precursor of 3-mercaptohexan-1-ol (3MH) using stable isotope dilution assay: Elements for understanding the 3MH production in wine

Roland, Aurélie; Schneider, Rémi; Guernevé, Christine Le; Razungles, Alain; Cavelier, Florine

doi:10.1016/j.foodchem.2009.12.095

Cited by 74 publications

(75 citation statements)

References 25 publications

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“…It has been shown more recently that glutathione precursors are an equally, if not more important, source of these pleasant smelling polyfunctional thiols (Subileau et al 2008, Fedrizzi et al 2009, Grant-Preece et al 2010, Roland et al 2010, Winter et al 2010. A recent study documented that the glutathione-conjugated 3MH diastereomers were up to 35 times more abundant than their cysteineconjugated counterparts in juices of Sauvignon blanc, Riesling, Chardonnay, and Pinot Grigio; Sauvignon blanc juices generally had the highest concentrations of the varieties studied .…”

Section: Volatile Sulfur Compoundsmentioning

confidence: 97%

“…However, that is no longer the case with the discovery of a number of volatile thiols that impart pleasant herbaceous, fruity, mineral, smoky, and toasty aromas in wine (Dubourdieu and Tominaga 2009). The most abundant volatile sulfur compounds in wines are H 2 S, methanthiol, dimethylmercaptans (dimethylsulfide, dimethyldisulfide, dimethyltrisulfide), methylthioesters (Smethyl thioacetate, S-methyl thiopropanoate, and S-methyl thiobutanoate), and liberated glutathione and cysteine polyfunctional thiols (4-mercapto-4-methylpentan-2-one, 4MMP; 3-mercaptohexan-1-ol, 3MH; and 3-mercaptohexyl acetate, 3MHA) , Dubourdieu and Tominaga 2009, Roland et al 2010. A myriad of other sulfur-containing compounds have been identified in wines, suggesting that there is still much to be discovered in this area , Bailly et al 2006, Sarrazin et al 2007b, Dubourdieu and Tominaga 2009.…”

Section: Volatile Sulfur Compoundsmentioning

confidence: 99%

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Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Robinson

Boss

Solomon

et al. 2013

Am. J. Enol. Vitic.

250

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Abstract:Wine is an ancient beverage and has been prized throughout time for its unique and pleasing flavor. Wine flavor arises from a mixture of hundreds of chemical components interacting with our sense organs, producing a neural response that is processed in the brain and resulting in a psychophysical percept that we readily describe as "wine." The chemical components of wine are derived from multiple sources; during fermentation grape flavor components are extracted into the wine and new compounds are formed by numerous chemical and biochemical processes. In this review we discuss the various classes of chemical compounds in grapes and wines and the chemical and biochemical processes that influence their formation and concentrations. The overall aim is to highlight the current state of knowledge in the area of grape and wine aroma chemistry.

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Section: Volatile Sulfur Compoundsmentioning

confidence: 97%

Section: Volatile Sulfur Compoundsmentioning

confidence: 99%

Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Robinson

Boss

Solomon

et al. 2013

Am. J. Enol. Vitic.

250

View full text Add to dashboard Cite

show abstract

“…Some precursors in the juice have been identified as being cysteinylated or glutathionylated precursors (Tominaga et al, 1998b;Peyrot des Ganchos et al, 2002;Fedrizzi et al, 2009). However, studies have shown that these precursors account for only a fraction of the total amount of thiols present in the wine (Subileau et al, 2008a;Roland et al, 2010a;2010b), and no direct correlation between precursor concentration and the amount of free volatile thiols in the resulting wines has been observed Roland et al, 2011;Pinu et al, 2012). Other than release from precursors, the biogenesis of volatile thiols also has been proposed.…”

Section: Volatile Thiolsmentioning

confidence: 99%

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Coetzee

Toit

2015

SAJEV

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Oxidation and the capacity for sufficient ageing potential of white wines are constant problems for winemakers worldwide. In general, it is accepted that certain grape varieties are especially sensitive to oxidation, suggesting that some of the chemical components key to their sensory attributes are strongly modulated by oxygen exposure. Sauvignon blanc is a well-documented example of an oxygen-sensitive wine, and understanding the stability of various compounds is crucial in order to preserve the fresh and fruity characters of Sauvignon blanc wines while preventing the formation of off-odours over a long period of time. Compounds such as the volatile thiols and methoxypyrazines are key aroma compounds responsible for the typical Sauvignon blanc aroma, while other aroma compounds, such as esters, alcohols and acids, can also contribute to the wine aroma. Oxidation-related compounds (such as aldehydes) can occur under certain conditions and it is essential to understand the chemistry behind oxidation to control and manage the development of various characteristics in wine. The sensory interactions occurring between various compounds (both aromatic and non-aromatic) are also important due to enhancing or suppressive effects that can mask certain aroma nuances. This review focuses on the stability of certain compounds of Sauvignon blanc wines during oxidation and ageing and how it affects the aromatic and non-aromatic composition of these wines. ABBREVIATIONS

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“…Both 3-MH and 4-MMP were first identified in passion fruit, Passiflora edulis (Engel and Tressl 1991) and can be detected at 10-100 times their perception threshold in wine (Tominaga et al 2000) where they impart Bgrapefruit^, Bpassionfruit^, Bboxwood^and Bcaturine^aromas (Darriet et al 1995;Dubourdieu et al 2006;Tominaga et al 2006). 4-MMP and 3-MH exist predominantly as non-volatile cysteine or glutathione conjugates in grapes (Fedrizzi et al 2009;Peyrot des Gachons et al 2002;Roland et al 2010). While 3-MH can be released in-mouth from Cys-3-MH by saliva bacteria (Starkenmann et al 2008a), the major contribution of 3-MH and 4-MMP to wine aroma occurs when Saccharomyces cerevisiae and other wine yeast species take up these conjugates and cleave them to release the corresponding free thiols (Anfang et al 2009;Darriet et al 1995;GrantPreece et al 2010;Winter et al 2011).…”

Section: Introductionmentioning

confidence: 99%

Unravelling glutathione conjugate catabolism in Saccharomyces cerevisiae: the role of glutathione/dipeptide transporters and vacuolar function in the release of volatile sulfur compounds 3-mercaptohexan-1-ol and 4-mercapto-4-methylpentan-2-one

Cordente

Capone

Curtin

2015

Appl Microbiol Biotechnol

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Sulfur-containing aroma compounds are key contributors to the flavour of a diverse range of foods and beverages, such as wine. The tropical fruit characters of Sauvignon Blanc wines are attributed to the presence of the aromatic thiols 3-mercaptohexan-1-ol (3-MH), its acetate ester 3-mercaptohexyl acetate (3-MHA), and 4-mercapto-4-methylpentan-2-one (4-MMP). These aromatic thiols are not detectable in grape juice to any significant extent but are released by yeast during alcoholic fermentation. While the processes involved in the release of 3-MH and 4-MMP from their cysteinylated precursors have been studied extensively, degradation pathways for glutathione S-conjugates (GSH-3-MH and GSH-4-MMP) have not. In this study, a candidate gene approach was taken, focusing on genes known to play a role in glutathione and glutathione-S-conjugate turnover in Saccharomyces cerevisiae. Our results confirm the role of Opt1p as the major transporter responsible for uptake of GSH-3-MH and GSH-4-MMP, and identify vacuolar Ecm38p as a key determinant of 3-MH release from GSH-3-MH. ECM38 was unimportant, on the other hand, for release of 4-MMP, and abolition of vacuolar biogenesis caused an increase in the amount of 4-MMP released. The alternative cytosolic glutathione degradation pathway was not involved in release of either thiol from their glutathionylated precursors. Finally, cycling of GSH-3-MH and/or its breakdown intermediates between the cytosol and the vacuole or extracellular space was implicated in modulation of 3-MH formation. Together, these results provide new targets for development of yeast strains that optimize release of these potent volatile sulfur compounds, and further our understanding of the processes involved in glutathione-S-conjugate turnover.

show abstract

Identification and quantification by LC–MS/MS of a new precursor of 3-mercaptohexan-1-ol (3MH) using stable isotope dilution assay: Elements for understanding the 3MH production in wine

Cited by 74 publications

References 25 publications

Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Unravelling glutathione conjugate catabolism in Saccharomyces cerevisiae: the role of glutathione/dipeptide transporters and vacuolar function in the release of volatile sulfur compounds 3-mercaptohexan-1-ol and 4-mercapto-4-methylpentan-2-one

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