Sensomics analysis of key bitter compounds in the hard resin of hops (Humulus lupulus L.) and their contribution to the bitter profile of Pilsner-type beer.

Journal of Agricultural and Food Chemistry
Michael DreselThomas Hofmann

Abstract

Recent brewing trials indicated the occurrence of valuable bitter compounds in the hard resin fraction of hop. Aiming at the discovery of these compounds, hop's ε-resin was separated by means of a sensory guided fractionation approach and the key taste molecules were identified by means of UV/vis, LC-TOF-MS, and 1D/2D-NMR studies as well as synthetic experiments. Besides a series of literature known xanthohumol derivatives, multifidol glucosides, flavon-3-on glycosides, and p-coumaric acid esters, a total of 11 bitter tastants are reported for the first time, namely, 1",2"-dihydroxanthohumol F, 4'-hydroxytunicatachalcone, isoxantholupon, 1-methoxy-4-prenylphloroglucinol, dihydrocyclohumulohydrochinone, xanthohumols M, N, and P, and isoxanthohumols M, N, and P, respectively. Human sensory analysis revealed low bitter recognition threshold concentrations ranging from 5 (co-multifidol glucopyranoside) to 198 μmol/L (trans-p-coumaric acid ethyl ester) depending on their chemical structure. For the first time, LC-MS/MS quantitation of these taste compounds in Pilsner-type beer, followed by taste re-engineering experiments, revealed the additive contribution of iso-α-acids and the identified hard resin components to be truly necessar...Continue Reading

References

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Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alexey G KuznetsovEugene V Babaev
Feb 10, 2009·Journal of Agricultural and Food Chemistry·Daniel IntelmannThomas Hofmann
Jul 25, 2009·Journal of Agricultural and Food Chemistry·Gesa HaseleuThomas Hofmann

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Citations

Oct 29, 2015·Journal of Agricultural and Food Chemistry·Yoshimasa TaniguchiKazutoshi Shindo
Jul 16, 2015·Journal of Agricultural and Food Chemistry·Monika StomporMirosław Anioł
Oct 5, 2016·Journal of Agricultural and Food Chemistry·Michael DreselThomas Hofmann
Dec 17, 2016·Journal of Agricultural and Food Chemistry·Kirsten Günther-JordanlandThomas Hofmann
Oct 26, 2018·Nucleic Acids Research·Ayana Dagan-WienerMasha Y Niv
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xin WangXiao-Ya Shang
Jul 1, 2018·Comprehensive Reviews in Food Science and Food Safety·Julia WannenmacherThomas Becker
May 1, 2016·Comprehensive Reviews in Food Science and Food Safety·Marcel KarabínPavel Dostálek
Jan 1, 2019·Comprehensive Reviews in Food Science and Food Safety·Emmanuel Hatzakis
Dec 31, 2017·Journal of Agricultural and Food Chemistry·Stefan Spreng, Thomas Hofmann
Jul 10, 2019·Journal of Agricultural and Food Chemistry·Mengfei LinHeqiang Huo
Dec 17, 2019·Journal of Agricultural and Food Chemistry·Johanna LainerThomas Hofmann
Aug 15, 2018·Journal of Natural Products·Achara RaksatSurat Laphookhieo
Jan 5, 2019·Chemical Research in Toxicology·Judy L BoltonBirgit M Dietz

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