Analytical investigations of wine odorant 3-mercaptohexan-1-ol and its precursors

ACS Symposium Series

Volumn 1104, Issue , 2012, Pages 15-35

  Capone, Dimitra L ^a,b   Sefton, Mark A ^b   Jeffery, David W ^b  

^a AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

^b UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

FRUIT JUICES; ODORS;

ANALYTICAL INVESTIGATIONS; CYSTEINYLGLYCINE; GRAPE JUICE; PRECURSOR CONCENTRATION; PROCESSING OPERATIONS;

WINE;

EID: 84905665596     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2012-1104.ch002     Document Type: Conference Paper

References (51)

1. King, E. S.; Osidacz, P.; Curtin, C.; Bastian, S. E. P.; Francis, I. L. Assessing desirable levels of sensory properties in Sauvignon Blanc wines - consumer preferences and contribution of key aroma compounds. Aust. J. Grape Wine Res. 2011, 17, 169-180
2. Mateo-Vivaracho, L.; Zapata, J.; Cacho, J.; Ferreira, V. Analysis, occurrence, and potential sensory significance of five polyfunctional mercaptans in white wines. J. Agric. Food Chem. 2010, 58, 10184-10194
3. Dubourdieu, D.; Tominaga, T.; Masneuf, I.; Peyrot des Gachons, C.; Murat, M. L. The role of yeasts in grape flavor development during fermentation: The example of Sauvignon blanc. Am. J. Enol. Vitic. 2006, 57, 81-88
4. Lund, C. M.; Thompson, M. K.; Benkwitz, F.; Wohler, M. W.; Triggs, C. M.; Gardner, R.; Heymann, H.; Nicolau, L. New Zealand Sauvignon Blanc distinct flavor characteristics: Sensory, chemical, and consumer aspects. Am. J. Enol. Vitic. 2009, 60, 1-12
5. Darriet, P.; Tominaga, T.; Lavigne, V.; Boidron, J.-N.; Dubourdieu, D. Identification of a powerful aromatic component of Vitis vinifera L. var. Sauvignon wines: 4-mercapto-4-methylpentan-2-one. Flavour Fragr. J. 1995, 10, 385-392
6. Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines. Flavour Fragr. J. 1998, 13, 159-162
7. Tominaga, T.; Darriet, P.; Dubourdieu, D. Identification of 3-mercaptohexyl acetate in Sauvignon wine, a powerful aromatic compound exhibiting boxtree odor. Vitis 1996, 35, 207-210
8. Swiegers, J. H.; Willmott, R.; Hill-Ling, A.; Capone, D. L.; Pardon, K. H.; Elsey, G. M.; Howell, K. S.; de Barros Lopes, M. A.; Sefton, M. A.; Lilly, M.; Pretorius, I. S. Modulation of volatile thiol and ester aromas by modified wine yeast. In Developments in Food Science; Bredie, W. L. P., Petersen, M. A., Eds.; Elsevier, New York, 2006; pp 113-116
9. Tominaga, T.; Niclass, Y.; Frerot, E.; Dubourdieu, D. Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (Var. Sauvignon Blanc and Semillon). J. Agric. Food Chem. 2006, 54, 7251-7255
10. Howell, K. S.; Swiegers, J. H.; Elsey, G. M.; Siebert, T. E.; Bartowsky, E. J.; Fleet, G. H.; Pretorius, I. S.; de Barros Lopes, M. A. Variation in 4-mercapto-4-methyl-pentan-2-one release by Saccharomyces cerevisiae commercial wine strains. FEMS Microbiol. Lett. 2004, 240, 125-129
11. Swiegers, J. H.; Capone, D. L.; Pardon, K. H.; Elsey, G. M.; Sefton, M. A.; Francis, I. L.; Pretorius, I. S. Engineering volatile thiol release in Saccharomyces cerevisiae for improved wine aroma. Yeast 2007, 24, 561-574
12. Tominaga, T.; Peyrot des Gachons, C.; Dubourdieu, D. A new type of flavor precursors in Vitis vinifera L. cv. Sauvignon Blanc: S-cysteine conjugates. J. Agric. Food Chem. 1998, 46, 5215-5219
13. Thibon, C.; Marullo, P.; Claisse, O.; Cullin, C.; Dubourdieu, D.; Tominaga, T. Nitrogen catabolic repression controls the release of volatile thiols by Saccharomyces cerevisiae during wine fermentation. Fems Yeast Res. 2008, 8, 1076-1086
14. Roncoroni, M.; Santiago, M.; Hooks, D. O.; Moroney, S.; Harsch, M. J.; Lee, S. A.; Richards, K. D.; Nicolau, L.; Gardner, R. C. The yeast IRC7 gene encodes a β-lyase responsible for production of the varietal thiol 4-mercapto- 4-methylpentan-2-one in wine. Food Microbiol. 2011, 28, 926-935
15. Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. 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. 2002, 50, 4076-4079
16. Capone, D. L.; Pardon, K. H.; Cordente, A. G.; Jeffery, D. W. Identification and quantification of 3-S-cysteinylglycinehexan-1-ol (Cysgly-3-MH) in Sauvignon Blanc grape juice by HPLC-MS/MS. J. Agric. Food Chem. 2011Submitted.
17. Murat, M.-L.; Tominaga, T.; Dubourdieu, D. Assessing the aromatic potential of Cabernet Sauvignon and Merlot musts used to produce Rose wine by assaying the cysteinylated precursor of 3-mercaptohexan-1-ol. J. Agric. Food Chem. 2001, 49, 5412-5417
18. Subileau, M.; Schneider, R.; Salmon, J.-M.; Degryse, E. 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. 2008, 56, 9230-9235
19. Pardon, K. H.; Graney, S. D.; Capone, D. L.; Swiegers, J. H.; Sefton, M. A.; Elsey, G. M. Synthesis of the individual diastereomers of the cysteine conjugate of 3-mercaptohexanol (3-MH). J. Agric. Food Chem. 2008, 56, 3758-3763
20. Grant-Preece, P. A.; Pardon, K. H.; Capone, D. L.; Cordente, A. G.; Sefton, M. A.; Jeffery, D. W.; Elsey, G. M. 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. 2010, 58, 1383-1389
21. Kobayashi, H.; Takase, H.; Kaneko, K.; Tanzawa, F.; Takata, R.; Suzuki, S.; Konno, T. Analysis of S-3-(hexan-1-ol)-glutathione and S-3-(hexan-1-ol)- Lcysteine in Vitis vinifera L. cv. Koshu for aromatic wines. Am. J. Enol. Vitic. 2010, 61, 176-185
22. Roland, A.; Schneider, R.; Guernevé, C. L.; Razungles, A.; Cavelier, F. 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. 2010, 121, 847-855
23. Winter, G.; Van Der Westhuizen, T.; Higgins, V. J.; Curtin, C.; Ugliano, M. 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. 2011, 17, 285-290
24. Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Measuring the aromatic potential of Vitis vinifera L. Cv. Sauvignon Blanc grapes by assaying S-cysteine conjugates, precursors of the volatile thiols responsible for their varietal aroma. J. Agric. Food Chem. 2000, 48, 3387-3391
25. Thibon, C.; Shinkaruk, S.; Tominaga, T.; Bennetau, B.; Dubourdieu, D. Analysis of the diastereoisomers of the cysteinylated aroma precursor of 3-sulfanylhexanol in Vitis vinifera grape must by gas chromatography coupled with ion trap tandem mass spectrometry. J. Chromatogr., A 2008, 1183, 150-157
26. Luisier, J.-L.; Buettner, H.; Volker, S.; Rausis, T.; Frey, U. Quantification of cysteine S-conjugate of 3-sulfanylhexan-1-ol in must and wine of Petite Arvine vine by stable isotope dilution analysis. J. Agric. Food Chem. 2008, 56, 2883-2887
27. Capone, D. L.; Sefton, M. A.; Hayasaka, Y.; Jeffery, D. W. 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. 2010, 58, 1390-1395
28. Roland, A.; Vialaret, J.; Moniatte, M.; Rigou, P.; Razungles, A.; Schneider, R. Validation of a nanoliquid chromatography-tandem 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 2010, 1217, 1626-1635
29. Allen, T.; Herbst-Johnstone, M.; Girault, M.; Butler, P.; Logan, G.; Jouanneau, S.; Nicolau, L.; Kilmartin, P. A. Influence of grape harvesting steps on varietal thiol aromas in Sauvignon blanc wines. J. Agric. Food Chem. 2011, 59, 10641-10650
30. Starkenmann, C.; Le Calve, B.; Niclass, Y.; Cayeux, I.; Beccucci, S.; Troccaz, M. Olfactory perception of cysteine-S-conjugates from fruits and vegetables. J. Agric. Food Chem. 2008, 56, 9575-9580
31. Ferreira, V.; Ortin, N.; Cacho, J. F. Optimization of a procedure for the selective isolation of some powerful aroma thiols - development and validation of a quantitative method for their determination in wine. J. Chromatogr., A 2007, 1143, 190-198
32. Tominaga, T.; Dubourdieu, D. A novel method for quantification of 2-methyl- 3-furanthiol and 2-furanmethanethiol in wines made from Vitis vinifera grape varieties. J. Agric. Food Chem. 2006, 54, 29-33
33. Mateo-Vivaracho, L.; Ferreira, V.; Cacho, J. Automated analysis of 2-methyl-3-furanthiol and 3-mercaptohexyl acetate at ng L-1 level by headspace solid-phase microextraction with on-fibre derivatisation and gas chromatography-negative chemical ionization mass spectrometric determination. J. Chromatogr., A 2006, 1121, 1-9
34. Mateo-Vivaracho, L.; Cacho, J.; Ferreira, V. Improved solid-phase extraction procedure for the isolation and in-sorbent pentafluorobenzyl alkylation of polyfunctional mercaptans: optimized procedure and analytical applications. J. Chromatogr., A 2008, 1185, 9-18
35. Rodríguez-Bencomo, J. J.; Schneider, R.; Lepoutre, J. P.; Rigou, P. Improved method to quantitatively determine powerful odorant volatile thiols in wine by headspace solid-phase microextraction after derivatization. J. Chromatogr., A 2009, 1216, 5640-5646
36. Capone, D. L.; Sefton, M. A.; Jeffery, D. W. 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. 2011, 59, 4649-4658
37. Roland, A.; Schneider, R.; Razungles, A.; Cavelier, F. Varietal thiols in wine: discovery, analysis and applications. Chem. Rev. 2011, 111, 7355-7376
38. Capone, D. L.; Jeffery, D. W. Effects of transporting and processing Sauvignon Blanc grapes on 3-mercaptohexan-1-ol precursor concentrations. J. Agric. Food Chem. 2011, 59, 4659-4667
39. Tilbrook, J.; Tyerman, S. D. Cell death in grape berries: varietal differences linked to xylem pressure and berry weight loss. Funct. Plant Biol. 2008, 35, 173-184
40. Fuentes, S.; Sullivan, W.; Tilbrook, J.; Tyerman, S. A novel analysis of grapevine berry tissue demonstrates a variety-dependent correlation between tissue vitality and berry shrivel. Aust. J. Grape Wine Res. 2010, 16, 327-336
41. Kalua, C. M.; Boss, P. K. Comparison of major volatile compounds from Riesling and Cabernet Sauvignon grapes (Vitis vinifera L.) from fruitset to harvest. Aust. J. Grape Wine Res. 2010, 16, 337-348
42. Adams, D. O.; Liyanage, C. Glutathione increases in grape berries at the onset of ripening. Am. J. Enol. Vitic. 1993, 44, 333-338
43. Maggu, M.; Winz, R.; Kilmartin, P. A.; Trought, M. C. T.; Nicolau, L. Effect of skin contact and pressure on the composition of Sauvignon Blanc must. J. Agric. Food Chem. 2007, 55, 10281-10288
44. Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Localization of Scysteine conjugates in the berry: effect of skin contact on aromatic potential of Vitis vinifera L. cv. Sauvignon blanc must. Am. J. Enol. Vitic. 2002, 53, 144-146
45. Roland, A.; Schneider, R.; Charrier, F.; Cavelier, F.; Rossignol, M.; Razungles, A. Distribution of varietal thiol precursors in the skin and the pulp of Melon B. and Sauvignon Blanc grapes. Food Chem. 2011, 125, 139-144
46. Thibon, C.; Dubourdieu, D.; Darriet, P.; Tominaga, T. 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. 2009, 114, 1359-1364
47. Roland, A.; Vialaret, J.; Razungles, A.; Rigou, P.; Schneider, R. Evolution of S-cysteinylated and S-glutathionylated thiol precursors during oxidation of Melon B. and Sauvignon blanc musts. J. Agric. Food Chem. 2010, 58, 4406-4413
48. Joslin, W. S.; Ough, C. S. Cause and fate of certain C6 compounds formed enzymatically in macerated grape leaves during harvest and wine fermentation. Am. J. Enol. Vitic. 1978, 29, 11-17
49. Molina, I.; Nicolas, M.; Crouzet, J. Grape alcohol dehydrogenase. I. Isolation and characterization. Am. J. Enol. Vitic. 1986, 37, 169-173
50. Deytieux, C.; Geny, L.; Lapaillerie, D.; Claverol, S.; Bonneu, M.; Doneche, B. Proteome analysis of grape skins during ripening. J. Exp. Bot. 2007, 58, 1851-1862
51. Kobayashi, H.; Takase, H.; Suzuki, Y.; Tanzawa, F.; Takata, R.; Fujita, K.; Kohno, M.; Mochizuki, M.; Suzuki, S.; Konno, T. Environmental stress enhances biosynthesis of flavor precursors, S-3-(hexan-1-ol)-glutathione and S-3-(hexan-1-ol)-L-cysteine, in grapevine through glutathione S-transferase activation. J. Exp. Bot. 2011, 62, 1325-1336.