Abstract
Isoxanthohumol (IX) and 8-prenylnaringenin (8-PN) are prenylated flavonoids of hops (Humulus lupulus L.) with estrogenic activity that are under investigation as dietary supplements for the treatment of menopausal symptoms in women. Previous studies suggest a variety of phase I metabolites for IX and 8-PN and some conjugates, but there is less information on the regiochemistry of their phase II conjugates.1 – 3 The aim of this study was to investigate regiochemistry of glucuronidation of IX and 8-PN by human liver microsomes. Four glucuronide metabolites of IX and 8-PN were obtained from the incubation of alamethicin-activated liver microsomes with uridine-5'-diphosphoglucuronic acid (UDPGA). Their characterization and structural confirmation were achieved by enzymatic formation with or without UDPGA, hydrolysis by β-glucuronidase hydrolysis, and by LC-MS/MS and 1H, 13C and 2D-NMR and after large-scale incubation and semi-preparative HPLC.
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