Identification and characterisation of thiolated polysulfides in must and wine using online SPE UHPLC-HRMS

Dekker, Susanne; Nardin, T.; Mattana, Mirko; Fochi, Igor; Larcher, R.

doi:10.1007/s00216-020-02734-1

Cited by 9 publications

(8 citation statements)

References 51 publications

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“…Recently, in 2020, a series of symmetric and asymmetric polysulfanes with cysteine and glutathione substituents were reported in real wines: G-S n -G, Cys-S n -Cys, G-S n -Cys (n = 2-5) [45,49]. A number of symmetric and asymmetric polysulfanes with aroma thiols 3-MH and 4-MMP were also detected in model and real wines: 3MH-S n -3MH, 4MMP-S n -4MMP, 3MH-S n -4MMP, Cys-S n -3MH, Cys-S n -4MMP, G-S n -3MH, G-S n -4MMP (n = 2-5) [43,81]. The formation of such disulfides (n = 2) was catalyzed by Cu(II) ions.…”

Section: Polysulfanes (R-s N -R ( ) )mentioning

confidence: 91%

“…Corresponding polysulfanes with n = 3-4 were obtained when elemental sulfur was added. The composition and ratio of polysulfanes differed in model and real wines, which should be related to the various stabilities and reactivities of these compounds [81]. In addition, the reactions of polysulfane formation can be affected by the matrix of real wines.…”

Section: Polysulfanes (R-s N -R ( ) )mentioning

confidence: 99%

“…The mechanisms of polysulfane formation are currently being discussed. As described, they can be obtained chemically in wines and model aqueous solutions due to the reaction of elemental sulfur or H 2 S with thiols [28,44,46,81] (Figure 2). In both cases, Cu(II) ions catalyze these reactions, which are usually present in must and wine, and which can be added before bottling for copper fining.…”

Section: Polysulfanes (R-s N -R ( ) )mentioning

confidence: 99%

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Sulfane Sulfur Compounds as Source of Reappearance of Reductive Off-Odors in Wine

Müller¹,

Rauhut

Tarasov

2022

Fermentation

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Reactive compounds with one or more sulfane sulfur atoms can be an important source of reductive off-odors in wine. These substances contain labile sulfur, which can participate in microbiological (enzymatic) and chemical transformations (including in the post-bottling period), releasing malodorous hydrogen sulfide (H2S) and its derivatives (MeSH, EtSH, etc.). The following sulfane sulfur compounds were considered in this review as important precursors in the wine chemistry of reductive aromas: elemental sulfur (S8), persulfides (R-S-S-H), polysulfanes (R-Sn-R(′)), polythionates (−O3S-Sn-SO3−), thiosulfate (S2O32−) and derivatives of (poly)sulfane monosulfonic acids (R-Sn-SO3H). This review discusses the formation of these compounds, their reactivity and chemical transformations in wine, including reactions of nucleophilic substitution. In particular, the reactions of thiolysis, thiosulfatolysis and sulfitolysis of sulfane sulfur compounds are described, which lead in the end to reductive aroma compounds. In this way, the review attempts to shed light on some of the mysteries in the field of sulfur chemistry in wine and the reappearance of reductive off-odors after bottling.

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Section: Polysulfanes (R-s N -R ( ) )mentioning

confidence: 91%

Section: Polysulfanes (R-s N -R ( ) )mentioning

confidence: 99%

Section: Polysulfanes (R-s N -R ( ) )mentioning

confidence: 99%

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Sulfane Sulfur Compounds as Source of Reappearance of Reductive Off-Odors in Wine

Müller¹,

Rauhut

Tarasov

2022

Fermentation

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“…The potential sinks of 3SH all arise from the reactivity of thiols with other components of the wine matrix, including thiol-containing compounds, and acetaldehyde [ 74 , 75 , 87 ]. The reaction of thiols with other thiol-containing compounds, such as glutathione and cysteine, as well as 3SH and 3SHA, forms polysulfides ( Scheme 6 steps N, O, and P), and this reaction can be reversible under some conditions [ 74 , 87 ]. The release of 3SH from polysulfide forms in wine matrices has not yet been confirmed.…”

Section: Further Exploration Of the Pathways To 3shmentioning

confidence: 99%

“… Summary of the current understanding of 3SH formation in enological matrices, as well as key potential sinks of 3SH. Adapted from: A: [ 69 ], B: [ 44 , 69 ], C: [ 70 ], D: [ 69 ], E: [ 69 ], F: [ 69 ]; G: [ 66 ], H: [ 55 ], I: [ 66 ], J: [ 66 ], K: [ 22 , 71 ], L: [ 72 ], M: [ 73 ], N: [ 74 ], O: [ 74 ], P: [ 74 ], and Q: [ 75 ]. …”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

Unraveling the Mystery of 3-Sulfanylhexan-1-ol: The Evolution of Methodology for the Analysis of Precursors to 3-Sulfanylhexan-1-ol in Wine

Muhl

Pilkington

Fedrizzi

et al. 2022

Foods

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Volatile polyfunctional thiol compounds, particularly 3-sulfanylhexan-1-ol (3SH) and 3-sulfanylhexyl acetate (3SHA), are key odorants contributing to the aroma profile of many wine styles, generally imparting tropical grapefruit and passionfruit aromas. 3SH and 3SHA are present in negligible concentrations in the grape berry, juice, and must, suggesting that they are released from non-volatile precursors present in the grape. The exploration of the nature and biogenesis of these precursors to 3SH and 3SHA has proven important for the elucidation of polyfunctional thiol biogenesis during alcoholic fermentation. The development and validation of appropriate analytical techniques for the analysis of 3SH precursors in enological matrices have been extensive, and this review explores the analysis and discovery of these precursor compounds. The development of analytical methods to analyze 3SH precursors, from the selection of the analytical instrument, sample preparation, and methods for standardization, will first be discussed, before highlighting how these techniques have been used in the elucidation of the biogenesis of 3SH and 3SHA in grape wines. Lastly, the future of thiol precursor analysis will be considered, with the development of new methods that greatly reduce the sample preparation time and enable multiple precursors, and the thiols themselves, to be quantitated using a single method.

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Thiols and Related Sulfur Compounds

2024

Understanding Wine Chemistry

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Identification and characterisation of thiolated polysulfides in must and wine using online SPE UHPLC-HRMS

Cited by 9 publications

References 51 publications

Sulfane Sulfur Compounds as Source of Reappearance of Reductive Off-Odors in Wine

Sulfane Sulfur Compounds as Source of Reappearance of Reductive Off-Odors in Wine

Unraveling the Mystery of 3-Sulfanylhexan-1-ol: The Evolution of Methodology for the Analysis of Precursors to 3-Sulfanylhexan-1-ol in Wine

Thiols and Related Sulfur Compounds

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