Concentrations of the volatile thiol 3-mercaptohexanol in Sauvignon blanc wines: No correlation with juice precursors

American Journal of Enology and Viticulture

Volumn 63, Issue 3, 2012, Pages 407-412

  Pinu, Farhana R ^a   Jouanneau, Sara ^b   Nicolau, Laura ^b   Gardner, Richard C ^a,b   Villas Boas, Silas G ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Correlation; Putative precursors; Sauvignon blanc; Volatile thiols

Indexed keywords

VITACEAE;

EID: 84865968616     PISSN: 00029254     EISSN: None     Source Type: Journal    
DOI: 10.5344/ajev.2012.11126     Document Type: Article

References (33)

1. Allen, T., M. Herbst-Johnstone, M. Girault, P. Butler, G. Logan, S. Jouanneau, L. Nicolau, and P.A. Kilmartin. 2011. Influence of grapeharvesting steps on varietal thiol aromas in Sauvignon blanc wines. J. Agric. Food Chem. 59:10641-10650.
2. Bell, S.J., and P.A. Henschke. 2005. Implications of nitrogen nutrition for grapes, fermentation and wine. Aust. J. Grape. Wine Res. 11:242-295.
3. Bely, M., J.M. Sablayrolles, and P. Barre. 1990. Description of alcoholic fermentation kinetics: Its variability and significance. Am. J. Enol. Vitic. 41:319-324.
4. Benkwitz, F., T. Tominaga, P.A. Kilmartin, C. Lund, M. Wohlers, and L. Nicolau. 2012. Identifying the chemical composition related to the distinct aroma characteristics of New Zealand Sauvignon blanc wines. Am. J. Enol. Vitic. 63:62-72.
5. Capone, D.L., M.A. Sefton, H. Yoji, and D.W. Jeffery. 2010. Analysis of precursors to wine odorant 3-mercaptohexan-1-ol using HPLC-MS/MS: Resolution and quantitation of diastereomers of 3-S-cysteinylhexan-1-ol and 3-S-glutathionylhexan-1-ol. J. Agric. Food Chem. 58:1390-1395.
6. Capone, D.L., K.H. Pardon, A.G. Cordente, and D.W. Jeffery. 2011a. Identification and quantitation of 3-S-cysteinylglycinehexan-1-ol (Cysgly-3-MH) in Sauvignon blanc grape juice by HPLC-MS/MS. J. Agric. Food Chem. 59:11204-11210.
7. Capone, D.L., M.A. Sefton, and D.W. Jeffery. 2011b. Application of a modified method for 3-mercaptohexan-1-ol determination to investigate the relationship between free thiol and related conjugates in grape juice and wine. J. Agric. Food Chem. 59:4649-4658.
8. Choné, X., V. Lavigne-Cruège, T. Tominaga, C. Van Leeuwen, C. Castagnède, C. Saucier, and D. Dubourdieu. 2006. Effect of vine nitrogen status on grape aromatic potential: Flavor precursors (Scysteine conjugates), glutathione and phenolic content in Vitis vinifera L. cv. Sauvignon blanc grape juice. J. Int. Sci. Vigne Vin 40:1-6.
9. Dubourdieu, D., T. Tominaga, I. Masneuf, C. Peyrot des Gachons, and M.L. Murat. 2006. The role of yeasts in grape flavor development during fermentation: The example of Sauvignon blanc. Am. J. Enol. Vitic. 57:81-88.
10. Grant-Preece, P.A., K.H. Pardon, D.L. Capone, A.G. Cordente, M.A. Sefton, D.W. Jeffery, and G.M. Elsey. 2010. Synthesis of wine thiol conjugates and labeled analogues: Fermentation of the glutathione conjugate of 3-mercaptohexan-1-ol yields the corresponding cysteine conjugate and free thiol. J. Agric. Food Chem. 58:1383-1389.
11. Hebditch, K.R., L. Nicolau, and M.A. Brimble. 2007. Synthesis of isotopically labelled thiol volatiles and cysteine conjugates for quantification of Sauvignon Blanc wine. J. Labelled Compd. Rad. 50:237-243.
12. Kobayashi, H., H. Takase, K. Kaneko, F. Tanzawa, R. Takata, S. Suzuki, and T. Konno. 2010. Analysis of S-3-(hexan-1-ol)-glutathione and S-3-(hexan-1-ol)-l-cysteine in Vitis vinifera L. cv. Koshu for aromatic wines. Am. J. Enol. Vitic. 61:176-185.
13. Lee, S.A., F.E. Rick, J. Dobson, M. Reeves, H. Clark, M. Thomson, and R.C. Gardner. 2008. Grape juice is the major influence on volatile thiol aromas in Sauvignon Blanc. Aust. N.Z. Grapegr. Winemaker (36th Ann. Tech. Issue) 533(6):78-86.
14. Lund, C.M., M.K. Thompson, F. Benkwitz, M.W. Wohler, C.M. Triggs, R. Gardner, H. Heymann, and L. Nicolau. 2009. New Zealand Sauvignon blanc distinct flavor characteristics: Sensory, chemical, and consumer aspects. Am. J. Enol. Vitic. 60:1-12.
15. Murat, M.L., I. Masneuf, P. Darriet, V. Lavigne, T. Tominaga, and D. Dubourdieu. 2001. Effect of Saccharomyces cerevisiae yeast strains on the liberation of volatile thiols in Sauvignon blanc wine. Am. J. Enol. Vitic. 52:136-139.
16. Nikolantonaki, M., I. Chichuc, P.L. Teissedre, and P. Darriet. 2010. Reactivity of volatile thiols with polyphenols in a wine-model medium: Impact of oxygen, iron, and sulfur dioxide. Anal. Chim. Acta 660:102-109.
17. Pardon, K.H., S.D. Graney, D.L. Capone, J.H. Swiegers, M.A. Sefton, and G.M. Elsey. 2008. Synthesis of the individual diastereomers of the cysteine conjugate of 3-mercaptohexanol (3-MH). J. Agric. Food Chem. 56:3758-3763.
18. Peyrot des Gachons, C., T. Tominaga, and D. Dubourdieu. 2002. Sulfur aroma precursor present in S-glutathione conjugate form: Identification of S-3-(hexan-1-ol)-glutathione in must from Vitis vinifera L. cv. Sauvignon Blanc. J. Agric. Food Chem. 50:4076-4079.
19. Peyrot des Gachons, C., C. Van Leeuwen, T. Tominaga, J.P. Soyer, J.P. Gaudillere, and D. Dubourdieu. 2005. Influence of water and nitrogen deficit on fruit ripening and aroma potential of Vitis vinifera L. cv. Sauvignon blanc in field conditions. J. Sci. Food. Agric. 85:73-85.
20. Roland, A., R. Schneider, C.L. Guernevé, A. Razungles, and F. Cavelier. 2010a. 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. Food Chem. 121:847-855.
21. Roland, A., J. Vialaret, M. Moniatte, P. Rigou, A. Razungles, and R. Schneider. 2010b. Validation of a nanoliquid chromatographytandem mass spectrometry method for the identification and the accurate quantification by isotopic dilution of glutathionylated and cysteinylated precursors of 3-mercaptohexan-1-ol and 4-mercapto-4-methylpentan-2-one in white grape juices. J. Chromatogr., A 1217:1626-1635.
22. Roland, A., R. Schneider, A. Razungles, C. Le Guernevé, and F. Cavelier. 2010c. Straightforward synthesis of deuterated precursors to demonstrate the biogenesis of aromatic thiols in wine. J. Agric. Food. Chem. 58:10684-10689.
23. Roland, A., et al. 2011. Varietal thiols in wine: Discovery, analysis and applications. Chem. Rev. 111:7355-7376.
24. Schneider, R., F. Charrier, A. Razungles, and R. Baumes. 2006. Evidence for an alternative biogenetic pathway leading to 3-mercaptohexanol and 4-mercapto-4-methylpentan-2-one in wines. Anal. Chim. Acta 563:58-64.
25. Subileau, M., R. Schneider, J.M. Salmon, and E. Degryse. 2008. New insights on 3-mercaptohexanol (3MH) biogenesis in Sauvignon Blanc wines: Cys-3MH and (E)-hexen-2-al are not the major precursors. J. Agric. Food Chem. 56: 9230-9235.
26. Swiegers, J.H., E.J. Bartowsky, P.A. Henschke, and I.S. Pretorius. 2005. Yeast and bacterial modulation of wine aroma and flavour. Aust. J. Grape Wine Res. 11:139-173.
27. Swiegers, J.H., D.L. Capone, K.H. Pardon, G.M. Elsey, M.A. Sefton, I.L. Francis, and I.S. Pretorius. 2007. Engineering volatile thiol release in Saccharomyces cerevisiae for improved wine aroma. Yeast 24:561-574.
28. Thibon, C., D. Dubourdieu, P. Darriet, and T. Tominaga. 2009. Impact of noble rot on the aroma precursor of 3-sulfanylhexanol content in Vitis vinifera L. cv Sauvignon blanc and Semillon grape juice. Food Chem. 114:1359-1364.
29. Tominaga, T., P. Darriet, and D. Dubourdieu. 1996. Identification of 3-mercaptohexyl acetate in Sauvignon wine, a powerful aromatic compound exhibiting box-tree odor. Vitis 35:207-210.
30. Tominaga, T., C. Peyrot des Gachons, and D. Dubourdieu. 1998a. A new type of flavor precursors in Vitis vinifera L. cv. Sauvignon Blanc: S-Cysteine conjugates. J. Agric. Food Chem. 46:5215-5219.
31. Tominaga, T., A. Furrer, R. Henry, and D. Dubourdieu. 1998b. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines. Flav. Frag. J. 13:159-162.
32. Tominaga, T., R. Baltenweck-Guyot, C. Peyrot des Gachons, and D. Dubourdieu. 2000. Contribution of volatile thiols to the aromas of white wines made from several Vitis vinifera grape varieties. Am. J. Enol. Vitic. 51:178-181.
33. Winter, G., T. Van Der Westhuizen, V.J. Higgins, C. Curtin, and M. Ugliano. 2011. Contribution of cysteine and glutathione conjugates to the formation of the volatile thiols 3-mercaptohexan-1-ol (3MH) and 3-mercaptohexyl acetate (3MHA) during fermentation by Saccharomyces cerevisiae. Aust. J. Grape Wine Res. 17:285-290.