Identification and quantification of the oxidation products derived from α-acids and β-acids during storage of hops (Humulus lupulus L.)

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 12, 2013, Pages 3121-3130

  Taniguchi, Yoshimasa ^a   Matsukura, Yasuko ^a   Ozaki, Hiromi ^a   Nishimura, Koichi ^a   Shindo, Kazutoshi ^b  

^a KIRIN HOLDINGS CO LTD   (Japan)

^b JAPAN WOMEN'S UNIVERSITY   (Japan)

Author keywords

acids; acids; 4 hydroxy allohumulinone; beer; hop; hulupone; humulinone; Humulus lupulus L.; oxidation; storage

Indexed keywords

ANALYTICAL METHOD; HIGH RESOLUTION MASS SPECTROMETRY; HOP; HULUPONE; HUMULINONE; HUMULUS LUPULUS L; OXIDATION PRODUCTS; OXIDATIVE PRODUCTS;

BEER; ENERGY STORAGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

OXIDATION;

CYCLOHEXENE DERIVATIVE; HUMULON; PLANT RESIN; TERPENE;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FOOD PRESERVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMULUS; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOHEXENES; FOOD PRESERVATION; HUMULUS; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; RESINS, PLANT; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TERPENES;

HUMULUS; HUMULUS LUPULUS;

EID: 84875753877     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf3047187     Document Type: Article

References (36)

1. Urban, J.; Dahlberg, C. J.; Carroll, B. J.; Kaminsky, W. Absolute configuration of beer's bitter compounds Angew. Chem., Int. Ed. 2013, 52, 1553-1555
2. Malowicki, M. G.; Shellhammer, T. H. Isomerization and degradation kinetics of hop (Humulus lupulus) acids in a model wort-boiling system J. Agric. Food Chem. 2005, 53, 4434-4439
3. Haseleu, G.; Lagemann, A.; Stephan, A.; Intelmann, D.; Dunkel, A.; Hofmann, T. Quantitative sensomics profiling of hop-derived bitter compounds throughout a full-scale beer manufacturing process J. Agric. Food Chem. 2010, 58, 7930-7939
4. De Keukeleire, D. Fundamentals of beer and hop chemistry Quim. Nova 2000, 23, 108-112
5. Kowaka, M.; Kokubo, E. Composition of bitter substances of hops and characteristics of beer bitterness J. Am. Soc. Brew. Chem. 1977, 35, 16-21
6. Bishop, L. R.; Whitear, A. L.; Inman, W. R. Scientific basis for beer foam formation and cling J. Inst. Brew. 1974, 80, 68-80
7. Teuber, M.; Schmalreck, A. F. Membrane leakage in Bacillus subtilis 168 induced by the hop constituents lupulone, humulone, isohumulone, and humulinic acid Arch. Mikrobiol. 1973, 94, 159-171
8. Howard, G. A.; Martin, P. A. Bittering power of stored hops J. Inst. Brew. 1964, 70, 424-439
9. Aitken, R. A.; Bruce, A.; Harris, J. O.; Seaton, J. C. Bitterness of hop-derived materials in beer J. Inst. Brew. 1970, 76, 29-36
10. Whitear, A. L. Changes in resin composition and brewing behavior of hops during storage J. Inst. Brew. 1966, 72, 177-183
11. Ono, M.; Kakudo, Y.; Yamamoto, R.; Nagami, K.; Kumada, J. Simultaneous analysis of hop bittering components by high-performance liquid chromatography. II. Evaluation of hop deterioration J. Am. Soc. Brew. Chem. 1987, 45, 61-69
12. Foster, R. T., II; Weber, K.; Jangaard, N. O. The effect of hop acids transformation on kettle utilization and finished beer flavor and aroma Tech. Q.-Master Brew. Assoc. Am. 1981, 18, 109-115
13. Cook, A. H.; Howard, G. A.; Slater, C. A. Chemistry of hop constituents. VIII. Oxidation of humulone and cohumulone J. Inst. Brew. 1955, 61, 321-325
14. Shoolery, J. N.; Verzele, M.; Alderweireldt, F. On the structure of humulinone Tetrahedron 1960, 9, 271-274
15. Verzele, M.; Anteunis, M.; Alderweireldt, F. Isohumulones J. Inst. Brew. 1965, 71, 232-239
16. Cook, A. H.; Harris, G. Chemistry of hop constituents. I. Humulinone, a new constituent of hops J. Chem. Soc. 1950, 1873-1876
17. Verzele, M.; Govaert, F. Humulinone. Its alleged occurrence in hops J. Chem. Soc. 1952, 3313-3315
18. Whitear, A. L.; Hudson, J. R. Hop resins and beer flavor. III. Hop resins in beer J. Inst. Brew. 1964, 70, 24-30
19. Whitear, A. L. Reversed-phase paper chromatography of hop resins Chem. Ind. (London, U. K.) 1962, 1464-1465
20. Laws, D. R. J.; McGuinness, J. D. Analytical and brewing significance of a tricyclic oxidation product of humulone (tricyclodehydroisohumulone) J. Inst. Brew. 1974, 80, 174-180
21. Ashurst, P. R.; Elvidge, J. A. Hop constituents. XXVIII. Structure of an autoxidation product of humulone J. Chem. Soc. C 1966, 7, 675-676
22. Stevens, R.; Wright, D. Evaluation of hops. X. Hulupones and the significance of β acids in brewing J. Inst. Brew. 1961, 67, 496-501
23. Haseleu, G.; Intelmann, D.; Hofmann, T. Identification and RP-HPLC-ESI-MS/MS quantitation of bitter-tasting β-acid transformation products in beer J. Agric. Food Chem. 2009, 57, 7480-7489
24. Haseleu, G.; Intelmann, D.; Hofmann, T. Structure determination and sensory evaluation of novel bitter compounds formed from β-acids of hop (Humulus lupulus L.) upon wort boiling Food Chem. 2009, 116, 71-81
25. Intelmann, D.; Kummerloewe, G.; Haseleu, G.; Desmer, N.; Schulze, K.; Froehlich, R.; Frank, O.; Luy, B.; Hofmann, T. Structures of storage-induced transformation products of the beer's bitter principles, revealed by sophisticated NMR spectroscopic and LC-MS techniques Chem.-Eur. J. 2009, 15, 13047-13058
26. Intelmann, D.; Demmer, O.; Desmer, N.; Hofmann, T. 18O stable isotope labeling, quantitative model experiments, and molecular dynamics simulation studies on the trans-specific degradation of the bitter tasting iso-α-acids of beer J. Agric. Food Chem. 2009, 57, 11014-11023
27. Intelmann, D.; Hofmann, T. On the autoxidation of bitter-tasting iso-α-acids in beer J. Agric. Food Chem. 2010, 58, 5059-5067
28. Intelmann, D.; Haseleu, G.; Dunkel, A.; Lagemann, A.; Stephan, A.; Hofmann, T. Comprehensive sensomics analysis of hop-derived bitter compounds during storage of beer J. Agric. Food Chem. 2011, 59, 1939-1953
29. Intelmann, D.; Haseleu, G.; Hofmann, T. LC-MS/MS quantitation of hop-derived bitter compounds in beer using the ECHO technique J. Agric. Food Chem. 2009, 57, 1172-1182
30. James, P.; Tynan, T.; McMurrough, I.; Byrne, J. Preparation, purification and separation by high performance liquid chromatography of humulinic acids, dehydrohumulinic acids, and hulupones J. Inst. Brew. 1990, 96, 137-141
31. Hughes, P. S. Preparative regime for the purification of bitter acids derived from hops (Humulus lupulus L.) J. Chromatogr., A 1996, 731, 327-330
32. Alderweireldt, F.; Verzele, M.; Anteunis, M.; Dierckens, J. The isomerization products of humulone Bull. Soc. Chim. Belg. 1965, 74, 29-40
33. Howard, G. A.; Slater, C. A. Chemistry of hop constituents. XII. The structure of humulinone J. Chem. Soc. 1958, 1460-1462
34. De Keukeleire, D.; Siaens, E.; Verzele, M. Regiospecific singlet oxygen oxidation of (-) R-tetrahydrohumulone and hexahydrocolupulone Bull. Soc. Chim. Belg. 1976, 85, 293-304
35. Verzele, M.; De Keukeleire, D. Chemistry and Analysis of Hop and Beer Bitter Acids; Elsevier: Amsterdam, The Netherlands, 1991; p 90.
36. de Almeida, N. E. C.; Homem-de-Mello, P.; De Keukeleire, D.; Cardoso, D. R. Reactivity of beer bitter acids toward the 1-hydroxyethyl radical as probed by spin-trapping electron paramagnetic resonance (EPR) and electrospray ionization-tandem mass spectrometry (ESI-MS/MS) J. Agric. Food Chem. 2011, 59, 4183-4191