New insights on 3-mercaptohexanol (3MH) biogenesis in Sauvignon Blanc wines: Cys-3MH and (E)-hexen-2-al are not the major precursors

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 19, 2008, Pages 9230-9235

  Subileau, Maeva ^a,b   Schneider, Rémy ^a   Salmon, Jean Michel ^a   Degryse, Eric ^b  

^a SPO   (France)

^b Pernod Ricard   (France)

Author keywords

Precursor; Sauvignon blanc; Thiol

Indexed keywords

VITACEAE;

EID: 54349118243     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf801626f     Document Type: Article

References (36)

1. Buettner, A.; Schieberle, P. Characterization of the most odor-active volatiles in fresh, hand-squeezed juice of grapefruit (Citrus paradisi Macfayden). J. Agric. Food Chem. 1999, 47, 5189-5193.
2. Engel, K. H.; Tressl, R. Identification of a new sulfur containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa). J. Agric. Food Chem. 1991, 39, 2249-2252.
3. Du Plessis, C. S.; Augustyn, O. P. H. Initial study on the guava aroma of Chenin blanc and Colombard wines. S. Afr. J. Enol. Vitic. 1981, 2, 101-103.
4. 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 Fragrance J. 1995, 10, 385-392.
5. 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 Fragrance J. 1998, 13, 159-162.
6. Tominaga, T.; Darriet, P.; Dubourdieu, D. Identification of 3-mercaptohexanol acetate, compound having a powerful odor reminiscent of box-tree, involved in the aroma of Sauvignon wines. Vitis 1996, 35, 207-210.
7. 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 in wine by modified wine yeast. Proceedings of the Weurman Flavour Research Symposium. Developments in Food Science, Roskilde, Denmark. June 21-24, 2005; Elsevier: Amsterdam, The Netherlands, 2005.
8. Swiegers, J. H.; Pretorius, I. S. Modulation of volatile sulfur compounds by wine yeast. Appl. Microbiol. Biotechnol. 2007, 74, 954-960.
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. Dagan, L. Potentiel aromatique des raisins de Vitis vinifera L. cv. Petit Manseng et Gros Manseng. Contribution à l'arôme des vins de pays des Côtes de Gascogne., Agro M, 2006.
11. Escudero, A.; Gogorza, B.; Melus, M. A.; Ortin, N.; Cacho, J.; Ferreira, V. Characterization of the aroma of a wine from maccabeo. Key role played by compounds with low odor activity values. J. Agric. Food Chem. 2004, 52, 3516-3524.
12. Schneider, R. Contribution à la conaissance de l'arôme et du potentiel aromatique du Melon B (Vitis vinifera L.) et des vins de Muscadet, Montpellier II, 2001.
13. Schneider, R.; Kotseridis, Y.; Ray, J. L.; Augier, C.; Baumes, R. Quantitative determination of sulfur-containing wine odorants at sub parts per billion levels. 2. Development and application of a stable isotope dilution assay. J. Agric. Food Chem. 2003, 51, 3243-3248.
14. Ferreira, V.; Ortin, N.; Escudero, A.; Lopez, R.; Cacho, J. Chemical characterization of the aroma of Grenache rose wines: aroma extract dilution analysis, quantitative determination, and sensory reconstitution studies. J. Agric. Food Chem. 2002, 50, 4048-4054.
15. 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.
16. Tominaga, T.; Masneuf, I.; Dubourdieu, D. A S-cysteine conjugate, precursor of aroma of white Sauvignon. J. Int. Sci. Vigne Vin 1995, 29 (4), 227-232.
17. Tominaga, T.; Peyrot des Gachons, C.; Dubourdieu, D. A new type of flavor precursor in Vitis vinifera L. cv. Sauvignon Blanc: S-cysteine conjugates. J. Agric. Food Chem. 1998, 46, 5215-5219.
18. Howell, K. S.; Klein, M.; Swiegers, J. H.; Hayasaka, Y.; Elsey, G. M.; Fleet, G. H.; Hoj, P. B.; Pretorius, I. S.; de Barros Lopes, M. A. Genetic determinants of volatile-thiol release by Saccharomyces cerevisiae during wine fermentation. Appl. Environ. Microbiol. 2005, 71, 5420-5426.
19. 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.
20. Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Localization of S-cysteine 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.
21. Masneuf-Pomarede, I.; Mansour, C.; Murat, M. L.; Tominaga, T.; Dubourdieu, D. Influence of fermentation temperature on volatile thiols concentrations in Sauvignon blanc wines. Int. J. Food Microbiol. 2006, 108, 385-390.
22. Howell, K. S.; Swiegers, J. H.; Elsey, G. M.; Sieben, 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.
23. Schneider, R.; Charrier, F.; Razungles, A.; Baumes, R. Evidence for an alternative biogenetic pathway leading to 3-mercaptohexanol and 4-mercapto-4-methylpentan-2-one in wines. Anal. Chim. Acta 2006, 536, 58-64.
24. Cordonnier, R.; Bayonove, C. Etude de la phase perfermentaire de la vinification: extraction et formation de certains composés de l'arôme; cas des terpenols, des aldehydes et des alcools en C6. Connaiss. Vigne Vin 1981, 15, 269-286.
25. 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.
26. Subileau, M.; Salmon, J. M.; Schneider, R.; Degryse, E. Precursor uptake modulates the production of aromatic thiols during fermentation. FEMS Yeast Res. 2008, 8, 771-780.
27. Subileau, M. Parameters influencing varietal thiol release by strains of Saccharomyces cerevisiae: from a controlled synthetic medium to the complexity of Sauvignon blanc must, SupAgro, 2008.
28. Kotseridis, Y.; Ray, J. L.; Augier, C.; Baumes, R. Quantitative determination of sulfur containing wine odorants at sub-ppb levels. 1. Synthesis of the deuterated analogues. J. Agric. Food Chem. 2000, 48, 5819-5823.
29. Lévêque, L.; Le Blanc, M.; Pastor, R. Synthesis of per(poly)fluoroalkyl aldehydes RF(CH2nCHO). Tetrahedron Lett. 1998, 39, 8857-8860.
30. Sablayrolles, J. M.; Barre, P.; Grenier, P. Design of a laboratory automatic system for studying alcoholic fermentations in anisothermal enological conditions. Biotechnol. Tech. 1987, 1, 181-184.
31. Bourbouloux, A.; Shahi, P.; Chakladar, A.; Delrot, S.; Bachhawat, A. K. Hgt1p, a high affinity glutathione transporter from the yeast Saccharomyces cerevisiae. J. Biol. Chem. 2000, 275, 13259-13265.
32. Lubkowitz, M. A.; Barnes, D.; Breslav, M.; Burchfield, A.; Naider, F.; Becker, J. M. Schizosaccharomyces pombe isp4 encodes a transporter representing a novel family of oligopeptide transport-ers. Mol. Microbiol. 1998, 28, 729-741.
33. Hauser, M.; Narita, V.; Donhardt, A. M.; Naider, F.; Becker, J. M. Multiplicity and regulation of genes encoding peptide transporters in Saccharomyces cerevisiae. Mol. Membr. Biol. 2001, 18, 105-112.
34. Wiles, A. M.; Cai, H.; Naider, F.; Becker, J. M. Nutrient regulation of oligopeptide transport in Saccharomyces cerevisiae. Microbiology 2006, 152, 3133-3145.
35. Swiegers, J. H.; Francis, I. L.; Herderich, M. J.; Pretorius, I. S. Meeting consumer expectations through management in vineyard and winery: the choice of yeast for fermentation offers great potential to adjust the aroma of Sauvignon Blanc wine. Aust. N.Z. Wine Ind. 2006, 21, 34-42.
36. 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.