Identification and characteristics of new volatile thiols derived from the hop (Humulus luplus L.) cultivar nelson Sauvin

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 6, 2009, Pages 2493-2502

  Takoi, Kiyoshi ^a   Degueil, Marie ^b,c   Shinkaruk, Svitlana ^d   Thibon, Cécile ^b   Maeda, Katsuaki ^a   Ito, Kazutoshi ^a   Bennetau, Bernard ^b,c   Dubourdieu, Denis ^b   Tominaga, Takatoshi ^b  

^a SAPPORO BREWERIES LTD   (Japan)

^b UNIVERSITÉ DE BORDEAUX   (France)

^c CNRS   (France)

^d ENITA de Bordeaux   (France)

Author keywords

3 sulfanyl 4 methylpentan 1 ol; 3 sulfanyl 4 methylpentyl acetate; Beers; Flavor; Hops; Nelson Sauvin; Synergy; Thiols

Indexed keywords

CITRUS X PARADISI; HUMULUS; RHEUM X HYBRIDUM;

TERPENE; THIOL DERIVATIVE;

ARTICLE; BEER; CHEMISTRY; HUMAN; HUMULUS; MASS FRAGMENTOGRAPHY; ODOR; SPECIES DIFFERENCE; TASTE; VOLATILIZATION;

BEER; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; HUMULUS; ODORS; SMELL; SPECIES SPECIFICITY; SULFHYDRYL COMPOUNDS; TASTE; TERPENES; VOLATILIZATION;

EID: 64549119528     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8034622     Document Type: Article

References (29)

1. Foster, A.; Schmidt, R. The characterization and classification of hop varieties. Brauwelt Int. 1994, II, 108-124.
2. Perpéte, P.; Mélotte, L.; Dupire, S.; Collin, S. Varietal discrimination of hop pellets by essential oil analysis I. Comparison of fresh samples. J. Am. Soc. Brew. Chem. 1998, 56, 104-108.
3. Lermusieau, G.; Collin, S. Varietal discrimination of hop pellets. II. Comparison between fresh and aged samples. J. Am. Soc. Brew. Chem. 2001, 59, 39-43.
4. Steinhaus, M.; Schieberle, P. Comparison of the most odor-active compounds in fresh and dried hop cones (Humulus lupulus L. cultivar spatter select) based on GC-olfactometry and odor dilution techniques. J. Agric. Food Chem. 2000. 48, 1776-1783.
5. Fritsch, H. T.; Schieberle, P. Identification based on quantitative measurements and aroma recombination of the character impact odorants in a Bavarian Pilsner-type beer. J. Agric. Food Chem. 2005, 53, 7544-7551.
6. 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.
7. 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, 5061-5068.
8. Peacock, V. E.; Deinzer, M. L.; Likens, S. T.; Nickerson, G. B.; McGill, L. A. Floral hop aroma in beer. J. Agric. Food Chem. 1981, 29, 1265-1269.
9. Murakami, A. A.; Goldstein, H.; Navarro, A.; Seabrooks, J. R.; Ryder, D. S. Investigation of beer flavor by gas chromatography-olfactometry. J. Am. Soc. Brew. Chem. 2003, 61, 23-32.
10. 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, 6252-6261.
11. Graves, I. R.; Brier, M. B.; Chandra, G. S.; Alspach, P. A. Kettle Hop Flavour from New Zealand Hop (Humulus lupulus L.) cultivars. Proceedings of the 27th Convention of the Institute and Guild of Brewing, 17-22 March. 2002; Asia Pacific Section: Adelaide, Australia; (CD-ROM).
12. Beatson, R. A.; Ansell, K. A.; Graham, L. T. Breeding, development, and characteristics of the hop (Humulus lupulus) cultivar 'Nelson Sauvin'. N. Z. J. Crop Hortic. Sci. 2003. 31, 303-309.
13. Tominaga, T.; Murat, M.-L.; Dubourdieu, D. Development of a method for analyzing 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.
14. Vermeulen, C.; Lejeune, I.; Tran, T. T. H.; Collin, S. Occurrence of polyfunctional thiols in fresh lager beer. J. Agric. Food Chem. 2006, 54, 5061-5068.
15. 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.
16. Kishimoto, T.; Kobayashi, M.; Yano, N.; Iida, A.; Wanikawa, A. Comparison of 4-mercapto-4-methylpentan-2-one contents in hop cultivars from different growing regions. J. Agric. Food Chem. 2008, 56, 1051-1057.
17. Sarrazin, E.; Shinkaruk, S.; Tominaga, T.; Bennetau, B.; Frérot, E.; Dubourdieu, D. Odorous impact of volatile thiols on the aroma of young botrytized sweet wines: Identification and quantification of new sulfanyl alcohols. J. Agric. Food Chem. 2007, 55, 1437-1444.
18. Ellman, G. L. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 1959. 82, 70-77.
19. American Society for Testing and Materials. Subcomittee E-18. Standard Practice E-679 for Determination of Odor and Taste Thresholds by a Forced-Choice Ascending Concentration Series Method of Limits. ASTM: Philadelphia, PA, 1979.
20. 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.
21. 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.
22. Vermeulen, C.; Collin, S. Combinatorial synthesis and sensorial properties of 21 mercaptoesters. J. Agric. Food Chem. 2003, 51, 3618-3622.
23. Vermeulen, C.; Guyot-Declerck, C.; Collin, S. Combinatorial synthesis and sensorial properties of mercaptoprimary alcohols and analogues. J. Agric. Food Chem. 2003, 51, 3623-3628.
24. 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.
25. Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Measurement the aromatic potential of Vitis vinifera L. Sauvignon Blanc grapes by assaying S-cysteine conjugates, precursor of the volatile thiols responsible for their varietal aroma. J. Agric, Food Chem. 2000. 48, 3387-3391.
26. 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- mercapto-hexan-1-ol. J. Agric. Food Chem. 2001, 49, 5412-5417.
27. Kishimoto, T.; Morimoto, M.; Kobayashi, M.; Yano, N.; Wani-kawa, A. Behaviors of 3-mercaptohexan-l-ol and 3-mercaptohexyl acetate during brewing processes. J. Am. Soc. Brew. Chem. 2008, 66, 192-196.
28. Ferreira, V.; Ortím, N.; Escudero, A.; Lópes. R.; Cacho, J. Chemical characterization of the aroma of Grenache rosé wines: Aroma extract dilution analysis, quantitative determination, and sensory reconstitution studies. J. Agric. Food Chem. 2002, 50, 4048-4054.
29. Bailly, S.; Jerkovic, V.; Marchand-Brynaert, J.; Collin, S. Aroma extraction dilution analysis of Sauternes wines. Key role of polyfunctional thiols. J. Agric. Food Chem. 2006, 54, 7227-7234.