70872-29-6Relevant articles and documents
Synthesis of xanthohumol and xanthohumol-d3from naringenin
Andrusiak, Joanna,Mylkie, Kinga,Wysocka, Ma?gorzata,?cianowski, Jacek,Wolan, Andrzej,Budny, Marcin
, p. 28934 - 28939 (2021/09/22)
A six-step synthesis of xanthohumol (1a) and its d3-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound1bwas used as an internal standard in stable isotope dilution assays of1ain two Polish beers.
Synthesis and antiproliferative activity of minor hops prenylflavonoids and new insights on prenyl group cyclization
Pop?o′ nski, Jaros?aw,Turlej, Eliza,Sordon, Sandra,Tronina, Tomasz,Bartma′ nska, Agnieszka,Wietrzyk, Joanna,Huszcza, Ewa
, (2018/04/06)
Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops
Analysis of the components of hard resin in hops (Humulus lupulus L.) and structural elucidation of their transformation products formed during the brewing process
Taniguchi, Yoshimasa,Taniguchi, Harumi,Yamada, Makiko,Matsukura, Yasuko,Koizumi, Hideki,Furihata, Kazuo,Shindo, Kazutoshi
, p. 11602 - 11612 (2015/02/19)
The resins from hops (Humulus lupulus L.), which add the bitter taste to beer, are classified into two main subfractions, namely, soft and hard resins. α- and β-Acids in soft resin and their transformation during the wort boiling process are well-studied; however, other constituents in resins, especially hard resin, have been unidentified. In this study, we identified humulinones and hulupones as soft-resin components, in addition to 4′-hydroxyallohumulinones and tricyclooxyisohumulones A and B as hard-resin components. These compounds are all oxidation products derived from α- and β-acids. We also investigated compositional changes in the hard resin during the wort boiling process, which has a significant effect on the taste of the beer, by using model boiling experiments. The major changes were identified to be isomerization of 4′-hydroxyallohumulinones into 4′- hydroxyallo-cis-humulinones, followed by decomposition into cis-oxyhumulinic acids. These findings will be helpful in systematically evaluating and optimizing the effect of the hard resin on beer quality.