Zenger, Katharina and Agnolet, Sara and Schneider, Bernd and Kraus, Birgit (2015) Biotransformation of Flavokawains A, B, and C, Chalcones from Kava (Piper methysticum), by Human Liver Microsomes. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 63 (28). pp. 6376-6385. ISSN 0021-8561, 1520-5118
Full text not available from this repository. (Request a copy)Abstract
The in vitro metabolism of flavokawains A, B, and C (FKA, FKB, FKC), methoxylated chalcones from Piper methysticum, was examined using human liver microsomes. Phase I metabolism and phase II metabolism (glucuronidation) as well as combined phase I+II metabolism were studied. For identification and structure elucidation of microsomal metabolites, LC-HRESIMS and NMR techniques were applied. Major phase I metabolites were generated by demethylation in position C-4 or C-4' and hydroxylation predominantly in position C-4, yielding FKC as phase I metabolite of FKA and FKB, helichrysetin as metabolite of FKA and FKC, and cardamonin as metabolite of FKC. To an even greater extent, flavokawains were metabolized in the presence of uridine diphosphate (UDP) glucuronic acid by microsomal UDP-glucuronosyl transferases. For all flavokawains, monoglucuronides (FKA-2'-O-glucuronide, FKB-2'-O-glucuronide, FKC-2'-O-glucuronide, FKC-4-O-glucuronide) were found as major phase II metabolites. The dominance of generated glucuronides suggests a role of conjugated chalcones as potential active compounds in vivo.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | BLADDER-CANCER CELLS; NF-KAPPA-B; MASS-SPECTROMETRY; ANTIOXIDATIVE ACTIVITY; PRENYLATED CHALCONES; HUMULUS-LUPULUS; EXTRACT; METABOLITES; XANTHOHUMOL; PATHWAY; Piper methysticum; kava; flavokawain; cardamonin metabolism; human liver microsomes; glucuronides |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Technology (Prof. Göpferich) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Jul 2019 12:35 |
| Last Modified: | 05 Jul 2019 12:35 |
| URI: | https://pred.uni-regensburg.de/id/eprint/5186 |
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