The role of cysteine and cysteine–S conjugates as odour precursors in the flavour and fragrance industry

Starkenmann, Christian; Troccaz, Myriam

doi:10.1002/ffj.1907

Cited by 55 publications

(56 citation statements)

References 115 publications

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“…A range of cysteine S-conjugates, presumed to be derived from glutathione S-conjugates, have been identified in fruits and vegetables. When cleaved by enzymes with carbon-sulfur lyase activity, potent volatile sulfur compounds (VSCs) are released that impart characteristic aromas and flavours (Starkenmann et al 2008b).…”

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.

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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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“…Microbial biotransformations of sulfur compounds that occur during food preservation or spoilage, and even within the mouth, have also attracted substantial attention. [9][10][11][12][13] A much more limited number of sulfur flavours are of plant origin, generated as the products of enzyme reactions within fresh vegetables. This chapter focuses on the biosynthesis of these natural compounds.…”

Section: Sulfur Compounds As Flavour Volatilesmentioning

confidence: 99%

“…Measures to prevent damage from reactive oxygen species formed during aerobic metabolism are essential in all cells and glutathione has a major role involving reversible oxidation and reduction of the (10). (a) Via g-glutamyl intermediates from glutathione (9).…”

Section: The Biosynthesis Of Allium Flavour Precursors Via G-glutamylmentioning

confidence: 99%

“…(22), and a series of unstable sulfenic acids (23)(24)(25)(26). In onion, the 1-propenyl sulfenic acid (25) derived from PeCSO (12) is immediately a substrate for LFS (21), the major thermal breakdown product from MCSO (10) Alliinase cleaves CSOs 10-14 to ammonia, pyruvate (22) and unstable sulfenic acids 23-26, respectively, (Scheme 8.3) that undergo further chemical transformation resulting in a large series of sulfur compounds that change the flavour and odour over time. 14,15 The only subsequent step requiring biological catalysis is exclusive to onion and its relations and follows the release of 1-propenylsulfenic acid (25) from PeCSO (12) by alliinase, as shown in Scheme 8.4.…”

Section: Release Of the Allium Csosmentioning

confidence: 99%

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The Biosynthesis of Volatile Sulfur Flavour Compounds

Jones¹

2010

The Chemistry and Biology of Volatiles

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Many natural biological flavours are products of secondary metabolism and pose a particular challenge in understanding both their biosynthetic pathways and roles within their native organism. The concepts of primary and secondary metabolism were adopted at the end of the nineteenth century to distinguish the pathways for the biosynthesis of the essential metabolites required in all cells (e.g. amino acids, lipids, carbohydrates, nucleotides), whether plant, animal or microbial, from the metabolites that were frequently species-specific and initially considered dispensable (e.g. isoprenoids, phenolics, steroids). These definitions have inevitably become looser as knowledge of metabolism and genetics has advanced and demonstrate both complexity and conservation in biosynthetic pathways for secondary metabolites. The biosynthesis of secondary metabolites is now seen as the result of a highly organized and controlled process, frequently requiring large numbers of enzymes and complex genetic regulation. Furthermore, many secondary metabolites are now known to be essential for survival. 1 The early appreciation that secondary metabolites are usually restricted to a particular species has remained true. In contrast to the substantial uniformity of primary metabolism, secondary metabolism is frequently species-and indeed cell type-specific and understanding their biosynthesis requires research within the specific producer organisms. The model organism approach, which proved so powerful in advancing biological knowledge during the late twentieth century, therefore has limited value because the

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“…These thiol precursors 2 are found in grape skin and pulp at tens to hundreds of µg/L, with grape botrytis infection and ripeness, grape pressing, skin contact, and other processing operations greatly affecting their concentrations in juice (see Table 23.2.1 for some examples). Identical or related S-conjugates have been found in other natural matrices such as passion fruit, onion, bell pepper, and even human sweat, where they can serve as precursors to potent odorous thiols [5]. Research surrounding varietal thiols and their precursors is still very active, and complete explanations are not yet available.…”

mentioning

confidence: 99%