title: Structural elucidation of humulone autoxidation products and analysis of their occurrence in stored hops.
abstract: The transformation of α-acids [in hops (Humulus lupulus L.)] to iso-α-acids (in beer) during the brewing process is well known, but the occurrence and structure of the oxidized α-acids during hop storage are not well documented. Because an understanding of these oxidized compounds is essential to optimize the effects of oxidized hops on the quality of beer, we investigated the autoxidation products of humulone (a representative congener of α-acids) using a simplified autoxidation model. Among the oxidation products, tricyclooxyisohumulones A (1) and B (2), tricycloperoxyisohumulone A (3), deisopropyltricycloisohumulone (4), and the hemiacetal 5 of tricycloperoxyhumulone A (5') were isolated, and their structures were elucidated for the first time. The occurrence of compounds 1-4 in stored hops was verified using LC/MS/MS analysis. We also monitored the levels of compounds 1-4 during hop storage using LC/MS/MS analysis.
authors.affiliation: Research Laboratories for Health Science & Food Technologies, Research & Development Division, KIRIN Company, Ltd. , 1-13-5, Fukuura Kanazawa-ku, Yokohama-shi, Kanagawa 236-0004, Japan.
authors.forename: Yoshimasa
authors.initials: Y
authors.lastname: Taniguchi
authors.forename: Harumi
authors.initials: H
authors.lastname: Taniguchi
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Matsukura
authors.forename: Yasuji
authors.initials: Y
authors.lastname: Kawachi
authors.forename: Kazutoshi
authors.initials: K
authors.lastname: Shindo
mesh_terms: D001515:Beer / Q000032:analysis; D001711:Biotransformation; D053138:Cyclohexenes / Q000737:chemistry*; D005858:Germany; D027582:Humulus / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D013729:Terpenes / Q000737:chemistry*
chemical_list: D053138:Cyclohexenes; D013729:Terpenes; C007966:humulon