Enzymatic release of odourant polyfunctional thiols from cysteine conjugates in hop

Journal of the Institute of Brewing

Volumn 119, Issue 4, 2013, Pages 221-227

  Gros, Jacques ^a   Tran, Thi Thu Hang ^a   Collin, Sonia ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Apotyptophanase; Cysteine adduct; Hop (Humulus lupulus); Odour; Polyfunctional thiols; lyase

Indexed keywords

BEER; ION EXCHANGERS; ODORS;

APOTYPTOPHANASE; CATION EXCHANGERS; CYSTEINE ADDUCT; CYSTEINE-S CONJUGATE; HOP (HUMULUS LUPULUS); LYASE ACTIVITY; POLYFUNCTIONAL THIOLS; VARIETAL AROMAS;

AMINO ACIDS;

CITRUS X PARADISI; HUMULUS; HUMULUS LUPULUS;

EID: 84888438293     PISSN: 00469750     EISSN: 20500416     Source Type: Journal    
DOI: 10.1002/jib.80     Document Type: Article

References (41)

1. Vermeulen, C., Gijs, L. P., and Collin, S. (2001) Sensorial contribution and formation pathways of thiols in foods: a review. Food Rev. Int., 21, 69-137.
2. Tominaga, T., Furrer, A., Robert, H., and Dubourdieu, D. (1998) Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon Blanc wines. Flav. Fragr. J., 13, 159-162.
3. Schneider, R., Kotseridis, Y., Ray, J. L., Augier, C., and Baumes, R. (2006) 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., 51, 3243-3248.
4. Murat, M. L., Masneuf, I., Darriet, P., Lavigne, V., Tominaga, T., and Dubourdieu, D. (2001) Effect of Saccharomyces cerevisiae yeast strains on the liberation of volatile thiols in Sauvignon blanc Wine. Am. J. Enol. Vitic., 52, 136-139.
5. Guth, H. (1997) Identification of character impact odorants of different white wine varieties. J. Agric. Food Chem., 45, 3022-3026.
6. Fretz, C. B., Luisier, J.-L., Tominaga, T., and Amado, R. (2005) 3-Mercaptohexanol: an aroma impact compound of petite arvine wine. Am. J. Enol. Viticult., 56, 407-410.
7. Subileau, M., Schneider, R., Salmon, J. M., and Degryse, E. (2008) Nitrogen catabolite repression modulates the production of aromatic thiols characteristic of Sauvignon Blanc at the level of precursor transport. FEMS Yeast Res., 8, 771-780.
8. Tominaga, T., Peyrot des Gachons, C., and Dubourdieu, D. (1998) A new type of flavor precursors in Vitis vinifera L. cv. Sauvignon blanc: S-cysteine conjugates. J. Agric. Food Chem., 46, 5215-5219.
9. Gros, J., Thi Thu H. T., and Collin, S. (2013) Revue bibliographique sur les adduits cystéinés et glutathionés de la vigne en vue de leur investigation dans le houblon et la bière. Cerevisia, 38, 3-14.
10. Fretz, C. B., Rouvinez, V., Känel, S., Luisier, J. L., and Amado, R. (2006) Use of an experimental design model to determine the impact of different fermentation parameters on the development of flavour compounds in wine. Vitis, 45, 37-43.
11. Subileau, M. (2008) Paramètres influant sur la libération des thiols variétaux par la levure Saccharomyces cerevisiae: d'un milieu synthétique à la complexité d'un moût de Sauvignon blanc. PhD thesis. Ecole Nationale Supérieure d'Agronomie de Montpellier, Montpellier.
12. Subileau, M., Schneider, R., Salmon, J. M., and Degryse, E. (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.
13. Wakabayashi, H., Wakabayashi, M., Eisenreich, W., and Engel, K. H. (2002) Stereoselectiviy of the beta-lyase-catalyzed cleavage of S-cysteine conjugates of pulegone. Eur. Food Res. Technol., 215, 287-292.
14. Roland, A., Schneider, R., Razungles, A., Le Guerneve, C., and Cavelier, F. (2010) Straightforward synthesis of deuterated precursors to demonstrate the biogenesis of aromatic thiols in wine. J. Agric. Food Chem., 58, 10684-10689.
15. Tominaga, T., and Dubourdieu, D. (2000) Identification of cysteinylated aroma precursors of certain volatile thiols in passion fruit juice. J. Agric. Food Chem., 48, 2874-2876.
16. Starkenmann, C., Niclass, Y., and Escher S. (2007) Volatile organic sulfur-containing constituents in Poncirus trifoliata (L.) Raf. (Rutaceae). J. Agric. Food Chem., 55, 4511-4517.
17. Starkenmann, C., Niclass, Y., and Cayeux, I. (2010) Occurrence of 1-γ-glutamyl-S-(1-hydroxy-2-methyl-3-pentanyl)-l-cysteine and S-(1-ethyl-3-hydroxy-2-methylpropyl)-l-cysteine in fresh and processed Allium caepa L. cultivar. Flavour Fragrance J., 26, 378-384.
18. Starkenmann, C., and Niclass, Y. (2011) New cysteine-S-conjugate precursors of volatile sulfur compounds in bell peppers (Capsicum annuum L. cultivar). J. Agric. Food Chem., 59, 3358-3365.
19. Starkenmann, C., Niclass, Y., and Troccaz, M. (2011) Nonvolatile S-Alk(en)ylthio-l-cysteine derivatives in fresh onion (Allium cepa L. Cultivar). J. Agric. Food Chem., 59, 9457-9465.
20. Starkenmann, C., Niclass, Y., and Cayeux, I. (2011c) Occurrence of l-γ-glutamyl-S-(1-hydroxy-2-methyl-3-pentanyl)-l-cysteine and S-(1-ethyl-3-hydroxy-2-methylpropyl)-l-cysteine in fresh and processed Allium caepa L. cultivar. Flav. Fragr. J., 26, 378-384.
21. Gros, J., Nizet, S., and Collin, S. (2011) Occurrence of odorant polyfunctional thiols in the super alpha Tomahawk hop cultivar. Comparison with the thiol-rich Nelson Sauvin bitter variety. J. Agric. Food Chem., 59, 8853-8865.
22. Kishimoto, T., Wanikawa, A., Kono, K., and Shibata, K. (2006) Comparison of the odor-active compounds in unhopped beer and beers hopped with different hop varieties. J. Agric. Food Chem., 54, 8855-8861.
23. Kishimoto, T., Morimoto, M., Kobayashi, M., Yako, N., and Wanikawa, A. (2008) Behaviors of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate during brewing processes. J. Am. Soc. Brew. Chem., 3, 192-196.
24. Kishimoto, T., Kobayashi, M., Yako, N., Ayako, I., and Wanikawa, A. (2008) Comparison of 4-mercapto-4-methylpentan-2-one contents in hop cultivars from different growing regions. J. Agric. Food Chem., 56, 1051-1057.
25. Takoi, K., Degueil, M., Shinkaruk, S., Thibon, C., Maeda, K., Ito, K., Bennetau, B., Dubourdieu, D., and Tominaga, T. (2009) Identification and characteristics of new volatile thiols derived from the hop (Humulus lupulus L.) cultivar Nelson Sauvin. J. Agric. Food Chem., 57, 2493-2502.
26. Gros, J., Peeters, F., and Collin, S. (2012) Occurrence of polyfunctional thiols in beers hopped with different cultivars. First evidence of an S-cysteine conjugate in hop (Humulus lupulus L.). J. Agric. Food Chem., 60, 7805-7816.
27. Vermeulen, C. and Collin, S. (2003) Combinatorial synthesis and sensorial properties of 21 mercapto esters. J. Agric. Food Chem., 51, 3618-3622.
28. Vermeulen, C., Guyot-Declerck, C., and Collin, S. (2003) Combinatorial synthesis and sensorial properties of mercapto primary alcohols and analogues. J. Agric. Food Chem., 51, 3623-3628.
29. Thibon, C., Shinkaruk, S., Tominaga, T., Bennetau, B. E., and Dubourdieu, D. (2008) Analysis of the diastereoisomers of the cysteinylated aroma precursor of 3-sulphanylhexanol in Vitis vinifera grape must by gas chromatography coupled with ion trap tandem mass spectrometry. J. Chromatogr. A, 1183, 150-157.
30. Pardon, K. H., Graney, S. D., Capone, D. L., Swiegers, J. H., Sefton, M. A., and Elsey, G. M. (2008) Synthesis of the individual diastereomers of the cysteine conjugate of 3-mercaptohexanol (3-MH). J. Agric. Food Chem., 56, 3758-3763.
31. Gros, J., Nizet, S., and Collin, S. (2009) Hop allylic alcohols are precursors of sulfur-containing odorants in fresh beer. Acta Hortic., 848, 273-278.
32. Peyrot des Gachons, C., and Dubourdieu, D. (2000) 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., 48, 3387-3391.
33. Wakabayashi, H., Wakabayashi, M., Eisenreich, W., and Engel, K. H. (2004) Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by beta-lyase-catalysed cleavage of cysteine conjugate. J. Agric. Food Chem., 52, 110-116.
34. Roland, A., Schneider, R., Le Guerneve, C., Razungles, A., and Cavelier, F. (2010) 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.
35. Capone, D. L., Sefton, M. A., Jeffery, D. W. (2011) 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.
36. Tominaga, T. (1998) Recherches sur l'arôme varietal des vins de Vitis vinifera L. cv. Sauvignon blanc et sa genèse à partir de précurseurs inodores du raisin. PhD thesis no. 599, Université Victor Segalen Bordeaux I.
37. Luisier, J. L., Buettner, H., Völker, S., Rausis, T., and Frey, U. (2008) 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., 56, 2883-2887.
38. Huvaere, K., Sinnaeve, B., Van Bocxlaer J., and De Keukeleire, D. (2004) Photooxidative degradation of beer bittering principles: product analysis with respect to lightstruck flavour formation. Photochem. Photobiol. Sci., 3, 854-858.
39. Huvaere, K., Andersen, M., Skibsted, L., Heyerick, A., and De Keukeleire, D. (2005) Photooxidative degradation of beer bittering principles: a key step on the route to lightstruck flavor formation in beer. J. Agric. Food Chem., 53, 1489-1494.
40. Kuroiwa, Y., Hashimoto, N., Hashomoto, H., Kobuko, E., and Nakagawa, K. (1963) Factors essential for the evolution of sunstruck flavor. Proc. Am. Soc. Brew. Chem., 21, 181-193. http://www.asbcnet.org/journal/author.htm
41. Peyrot des Gachons, C., Tominaga, T., and Dubourdieu, D. (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.