Occurrence of odorant polyfunctional thiols in beers hopped with different cultivars. First evidence of an S -Cysteine conjugate in hop (Humulus lupulus L.)

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 32, 2012, Pages 7805-7816

  Gros, Jacques ^a   Peeters, Florence ^a   Collin, Sonia ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

beer; hop (Humulus lupulus); polyfunctional thiols; S cysteine conjugate; varietal aroma

Indexed keywords

ACCURATE PREDICTION; HOP (HUMULUS LUPULUS); INTERNAL STANDARDS; POLYFUNCTIONAL THIOLS; S-CYSTEINE CONJUGATE; VARIETAL AROMA;

AMINO ACIDS; FINITE DIFFERENCE METHOD;

BEER;

CYSTEINE; DRUG DERIVATIVE; PLANT EXTRACT; THIOL DERIVATIVE;

ARTICLE; BEER; CHEMISTRY; GAS CHROMATOGRAPHY; HUMAN; HUMULUS; ODOR;

BEER; CHROMATOGRAPHY, GAS; CYSTEINE; HUMANS; HUMULUS; ODORS; PLANT EXTRACTS; SMELL; SULFHYDRYL COMPOUNDS;

EID: 84865131006     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf301478m     Document Type: Article

References (46)

1. Haseleu, G.; Lagemann, A.; Stephan, A.; Intelmann, D.; Dunkel, A.; Hofmann, T. Quantitative sensomics profiling of hop-derivated bitter compounds throughout a full-scale beer manufacturing process J. Agric. Food Chem. 2010, 58, 7930-7939
2. Goiris, K.; De Ridder, M.; De Rouck, G.; Boeykens, A.; Van Opstaele, F.; Aerts, G.; De Cooman, L.; De Keukeleire, D. The oxygenated sesquiterpenoid fraction of hops in relation to the spicy hop character of beer J. Inst. Brew. 2002, 108, 86-93 (Pubitemid 34959929)
3. Simpson, W. J.; Hughes, P. S. Cooperative binding of potassium ions to trans -isohumulone in the presence of divalent and trivalent cations Bioorg. Med. Chem. Lett. 1993, 3, 79-772
4. Hughes, P. The significance of iso-a-acids for beer quality J. Inst. Brew. 2000, 106 (5) 271-276
5. Roberts, M. T.; Dufour, J.-P.; Lewis, A. C. Application of comprehensive multidimensional gas chromatography combined with time-of-flight-mass spectrometry (GC×GC-TOFMS) for high resolution analysis of hop essential oil J. Sep. Sci. 2004, 27, 473-478 (Pubitemid 38559803)
6. Perpète, P.; Mélotte, L.; Dupire, S.; Collin, S. Varietal discrimination of hop pellets. I. Comparison of fresh samples J. Am. Soc. Brew. Chem. 1998, 56, 104-108 (Pubitemid 29032301)
7. De Keukeleire, D.; De Cooman, L.; Everaert, E.; Sandra, P.; Vindevogel, J.; Szucs, R. Novel methodology for unambiguous identification of hop varieties. Institute of Brewing, 23rd Convention, Australia and New Zealand Section; Winetitles-Hyde Park Press: Adelaide, Australia, 1994; pp 129-132.
8. Steinhaus, M.; Wilhelm, W.; Schieberle, P. Comparison of the most odor-active volatiles in different hop varieties by application of a comparative aroma extract dilution analysis Eur. Food Res. Technol. 2007, 226, 45-55 (Pubitemid 47460716)
9. Eyres, G. T.; Marriott, P. J.; Dufour, J. P. Comparison of odor-active compounds in the spicy fraction of hop (Humulus lupulus L.) essential oil from four different varieties J. Agric. Food Chem. 2007, 55, 6252-6251
10. Buttery, G.; Ling, C. Identification of hop varieties by gas chromatographic analysis of their essential oils. Capillary gas chromatography patterns and analyses of hop oils from American grown varieties J. Agric. Food Chem. 1967, 15, 531-535
11. Siebert, K. J. Sensory analysis of hop oil-derived compounds in beer; flavor effects of individual compounds. Quality control Eur. Brew. Conv., Monogr. XXII, Symp. Hops 1994, 198-212
12. Kishimoto, T.; Wanikawa, A.; Kagami, N.; Kawatsura, K. Analysis of hop-derived terpenoids in beer and evaluation of their behavior using the stir bar-sorptive extraction method with GC-MS J. Agric. Food Chem. 2005, 53, 4701-4707 (Pubitemid 40937585)
13. Peppard, T. L.; Ramus, S. A.; Witt, C. A.; Siebert, K. J. Correlation of sensory and instrumental data in elucidation the effect of varietal differences on hop flavour in beer J. Am. Soc. Brew. Chem. 1989, 47, 18-26
14. Kishimoto, T.; Wanikawa, A.; Kono, K.; Shibata, K. Comparison of the odor-active compounds in unhopped beer and beers hopped with different hop varieties J. Agric. Food Chem. 2006, 54, 8855-8861 (Pubitemid 44797536)
15. Deinzer, M.; Yang, X. Hop aroma: character impact compounds found in beer, methods of formation of individual compounds. EBC Monograph XXII. Symposium on Hops, Zoeterwoude, The Netherlands; Verlag Hans Carl: Nurnberg, Germany, 1994; pp 81-197.
16. Moir, M. Hop aromatic compounds Eur. Brew. Conv., Monogr. XXII, Symp. Hops 1994, 165-180
17. Lermusieau, G.; Bulens, M.; Collin, S. Use of GC-Olfactometry to identify the hop aromatic compounds in beer J. Agric. Food Chem. 2001, 49, 3867-3874 (Pubitemid 32822709)
18. Steinhaus, M.; Schieberle, P. Transfer of the potent hop odorants linalool, geraniol and 4-methyl-4-sulfanyl-2-pentanone from hops into beer. Proceedings of the 31st European Breweries Convention Congress; Fachverlag Hans Carl: Nurnberg, Germany, 2007; pp 1004-1011.
19. Sanchez, N. B.; Lederer, C. L.; Nickerson, G. B.; Libbey, L. M.; McDaniel, M. R. Sensory and analytical evaluation of hop oil oxygenated fractions. In Food Science and Human Nutrition; Charalambous, G., Ed.; Elsevier Science: Amsterdam, The Netherlands, 1992; pp 371-402.
20. Deinzer, M.; Yang, X. Hop aroma: character impact compounds found in beer, methods of formation of individual compounds. EBC Monograph XXII. Symposium on Hops, Zoeterwoude, The Netherlands; Verlag Hans Carl: Nurnberg, Germany, 1994; pp 81-197.
21. Goiris, K.; De Ridder, M.; De Rouck, G.; Boeykens, A.; Van Opstaele, F.; Aerts, G.; De Cooman, L.; De Keukeleire, D. The oxygenated sesquiterpenoid fraction of hops in relation to the spicy hop character of beer J. Inst. Brew. 2002, 108, 86-93 (Pubitemid 34959929)
22. King, A.; Dickinson, J. R. Biotransformation of hop aroma terpenoids by ale and lager yeasts FEMS Yeast Res. 2003, 3, 53-62 (Pubitemid 36255464)
23. Takoi, K.; Koie, K.; Itoga, Y.; Katayama, Y.; Shimase, M.; Nakayama, Y.; Watari, J. Biotransformation of hop-derived monoterpene alcohols by lager yeast and their contribution to the flavor of hopped beer J. Agric. Food Chem. 2010, 58, 5050-5058
24. Takoi, K.; Degueil, M.; Shinkaruk, S.; Thibon, C.; Maeda, K.; Ito, K.; Bennetau, B.; Dubourdieu, D.; Tominaga, T. Identification and characteristics of new volatile thiols derived from the hop (Humulus lupulus L.) cultivar Nelson Sauvin J. Agric. Food Chem. 2009, 57, 2493-2502
25. Gros, J.; Nizet, S.; Collin, S. 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. 2011, 59, 8853-8865
26. Kishimoto, T.; Morimoto, M.; Kobayashi, M.; Yako, N.; Wanikawa, A. Behaviors of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate during brewing processes J. Am. Soc. Brew. Chem. 2008, 3, 192-196
27. 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 (Pubitemid 128488285)
28. Vermeulen, C.; Collin, S. Combinatorial synthesis and sensorial properties of 21 mercapto esters J. Agric. Food Chem. 2003, 51, 3618-3622
29. Vermeulen, C.; Guyot-Declerck, C.; Collin, S. Combinatorial synthesis and sensorial properties of mercapto primary alcohols and analogues J. Agric. Food Chem. 2003, 51, 3623-3628
30. Vermeulen, C.; Pellaud, J.; Gijs, L.; Collin, S. Combinatorial synthesis and sensorial properties of polyfunctional thiols J. Agric. Food Chem. 2001, 49, 5445-5449 (Pubitemid 33089690)
31. Vermeulen, C.; Collin, S. Synthesis and sensorial properties of mercaptoaldehydes J. Agric. Food Chem. 2002, 50, 5654-5659
32. Vermeulen, C.; Collin, S. Combinatorial synthesis and screening of novel odorants such as polyfunctional thiols Comb. Chem. High Throughput Screening 2006, 9, 5445-5449
33. Vermeulen, C.; Lejeune, I.; Tran, T. T. H.; Collin, S. Occurrence of polyfunctional thiols in fresh lager beers J. Agric. Food. Chem. 2006, 54, 5061-5068 (Pubitemid 44140903)
34. Tominaga, T.; Murat, M. L.; Dubourdieu, D. Development of a method for analysing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. cv. Sauvignon blanc J. Agric. Food Chem. 1998, 46, 1044-1048 (Pubitemid 128488112)
35. Grosch, W. Determination of potent odorants in foods by aroma extract dilution analysis (AEDA) and calculation of odor activity values (OAVs) Flavour Fragrance J. 1994, 9, 147-158
36. Thibon, C.; Shinkaruk, S.; Tominaga, T.; Bennetau, B. E.; 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
37. 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 (Pubitemid 351860181)
38. Starkenmann, C.; Niclass, Y.; Cayeux, I. 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 Flavour Fragrance J. 2011, 26 (6) 378-384
39. Blanchard, L.; Bouchilloux, P.; Darriet, P.; Tominaga, T. Caractérisation de la fraction volatile de nature soufrée dans les vins de Cabernet et Merlot au cours de lélevage en barriques. 6ème Symposium International dOenologie, Bordeaux, France; 1999.
40. Frankel, E. N. Review. Recent advances in lipid oxidation J. Sci. Food Agric. 1991, 54, 495-511
41. Irwin, A. J.; Bordeleau, J.; Barker, R. L. Model studies and flavor threshold determination of 3-methyl-2-butene-1-thiol in beer J. Am. Soc. Brew. Chem. 1993, 51, 1-3
42. Goldstein, H.; Ting, P.; Navarro, A.; Ryder, D. Water-soluble hop flavor precursors and their role in beer flavor. 27th European Brewery Convention; Cannes, France; IRL Press Ltd.: Oxford, England, 1999.
43. Gros, J.; Nizet, S.; Collin, S. Hop allylic alcohols are precursors of sulfur-containing odorants in fresh beer Acta Hortic. 2009, 848, 273-278
44. Gros, J.; Collin, S. Identification of a new light-struck off-flavour in "light-stable" beers Cerevisia 2012, 37, 10-14
45. 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 (Pubitemid 28352101)
46. Wakabayashi, H.; Wakabayashi, M.; Eisenreich, W.; Engel, H. K. Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by beta -lyase-catalyzed cleavage of cysteine conjugates J. Agric. Food Chem. 2004, 52, 110-116