LC-MS/MS quantitation of hop-derived bitter compounds in beer using the ECHO technique

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 4, 2009, Pages 1172-1182

  Intelmann, Daniel ^a   Haseleu, Gesa ^a   Hofmann, Thomas ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

acids; acids; Beer; ECHO technique; Hop; Iso acids; LC MS; Quantification

Indexed keywords

CYCLOHEXENE DERIVATIVE; HUMULON; PROPIOPHENONE DERIVATIVE; TERPENE; XANTHOHUMOL;

ARTICLE; BEER; CHEMISTRY; FOOD PRESERVATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMULUS; ISOLATION AND PURIFICATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ODOR; TANDEM MASS SPECTROMETRY; TASTE;

BEER; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOHEXENES; FOOD PRESERVATION; HUMULUS; MAGNETIC RESONANCE SPECTROSCOPY; ODORS; PROPIOPHENONES; TANDEM MASS SPECTROMETRY; TASTE; TERPENES;

HUMULUS;

EID: 64549129150     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf803040g     Document Type: Article

References (23)

1. Stevens, J. F.; Taylor, A. W.; Deinzer, M. L. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J. Chromatoar., A 1999, 832, 97-107.
2. Govaert, F.; Verzele, M.; Anteunis, M.; Fontyn, F.; Stockx, J. Xanthohumol. Experientia 1957, 13, 105-106.
3. De Keukeleire, D.; Verzele, M. The absolute configuration of the isohumulones and the humulinic acids. Tetrahedron 1971, 27, 4939-4945.
4. 1H NMR coupling. Chromatoaravhia 1996, 42, 499-505.
5. Hoek, A. C; Hermans-Lokkerbol, A. C. J.; Verpoorte, R. An improved NMR method for the quantification of α-acids in hops and hop products. Phytochem. Anal. 2001, 12, 53-57.
6. Khatib, A.; Wilson Erica, G.; Kim Hye, K.; Supardi, M.; Choi Young, H.; Verpoorte, R. NMR assignment of iso-α-acids from isomerised extracts of Humulus lupulus L. cones. Phytochem. Anal. 2007, 18, 371-377.
7. Helmja, K.; Vaher, M.; Piissa, T.; Kamsol, K.; Orav, A.; Kaljurand, M. Bioactive components of the hop strobilus: comparison of different extraction methods by capillary electrophoretic and chromatographic methods. J. Chromatogr., A 2007, 222-229.
8. Rigby, F. L.; Sihto, E.; Bars, A. Additional constituents of hops. J. Inst. Brew. 1962, 68, 60-65.
9. Smith, R. J.; Davidson, D. Natural foam stabilizing and bittering compounds derived from hops. J. Am. Soc. Brew. Chem. 1998, 56, 52-57.
10. Anonymous 9.8 Bitterness of beer (IM). In Analytica-EBC; EACEB Convention; Verlag Hans Carl Getranke-Fachverlag: Nürnberg, Germany, 1998.
11. Anonymous 7.8 Iso-α-, α- and β-acids in hop and isomerised hop extracts by HPLC. In Analytica-EBC; EACEB Convention: Verlag Hans Carl Getränke-Fachverlag: Nürnberg, Germany, 1998.
12. Verzele, M.; Van Kerrebroeck, M.; Dewaele, C.; Strating, J.; Verhagen, L. High-performance liquid chromatography of α- and β-acids in beer. J. Chromatogr. 1984, 294, 471-475.
13. Verzele, M.; Dewaele, C.; Van Kerrebroeck, M. Analysis of beer iso-a-acids by high-performance liquid chromatography without sample pre-treatment. J. Chrgmatogr. A 1982, 244, 321-326.
14. Nelson, M. D.; Dolan, J. W. Ion suppression in LC-MS-MS-a case study. LCGC North Am. 2002, 20
15. Zimmer, D. Introduction to quantitative liquid chromatography- tandem mass spectrometry (LC-MS-MS). Chromatoeravhia 2003, 57, 325-332.
16. Zrostlikova, J.; Hajslova, J.; Poustka, J.; Begany, P. Alternative calibration approaches to compensate the effect of co-extracted matrix components in liquid chromatography-electrospray ionization tandem mass spectrometry analysis of pesticide residues in plant materials. J. Chromatoer., A 2002, 973, 13-26.
17. Hughes, P. S. Preparative regime for the purification of bitter acids derived from hops (Humulus lupulus L.). J. Chrgmgtogr., A 1996, 731, 327-330.
18. Stevens, J. F.; Ivancic, M.; Hsu, V. L.; Deinzer, M. L. Prenylflavonoids from Humulus lupulus. Phytochemistry 1997, 44, 1575-1585.
19. Verzele, M.; De Keukeleire, D. In Chemistry and Analysis of Hop and Beer Bitter Acids; Elsevier: Amsterdam, The Netherlands, 1991.
20. Araki, S.; Takashio, M.; Shinotsuka, K. A new parameter for determination of the extent of staling in beer. J. Am. Soc. Brew. Chem. 2002, 60, 26-30.
21. Forster, A.; Beck, B.; Schmidt, R.; Jansen, C.; Mellenthin, A. On the composition of the low-molecular weight polyphenols in various hops and two origins (in German). Monatsschr. Brauwiss. 2002, 55, 98-108.
22. Malfliet, S.; Van Opstaele, F.; De Clippeleer, J.; Syryn, E.; Goiris, K.; De Cooman, L.; Aerts, G. Flavour instability of pale lager beers: determination of analytical markers in relation to sensory ageing. J. Inst. Brew. 2008, 114, 180-192.
23. Forster, A.; Massinger, S.; Schmidt, R. On the degradation of hop bitter compounds during storage of beer (in German). Brauwelt 2004, 144, 623.