Untergehrer, Monika and Buecherl, Daniel and Wittmann, Hans-Joachim and Strasser, Andrea and Heilmann, Joerg and Juergenliemk, Guido (2015) Structure-Dependent Deconjugation of Flavonoid Glucuronides by Human beta-Glucuronidase - In Vitro and In Silico Analyses. PLANTA MEDICA, 81 (12-13). pp. 1182-1189. ISSN 0032-0943, 1439-0221
Full text not available from this repository. (Request a copy)Abstract
Flavonoid glycosides are extensively metabolized to glucuronidated compounds after oral intake. Recently, a cleavage of quercetin glucuronides by -glucuronidase has been found. To characterize the deglucuronidation reaction and its structural prerequisites among the flavonoid subtypes more precisely, four flavonol glucuronides with varying glucuronidation positions, five flavone 7-O-glucuronides with varying A- and B-ring substitution as well as one flavanone- and one isoflavone-7-O-glucuronide were analyzed in a human monocytic cell line. Investigation of the deglucuronidation rates by HPLC revealed a significant influence of the glucuronidation position on enzyme activity for flavonols. Across the flavonoid subtypes, the C-ring saturation also showed a significant influence on deglucuronidation, whereas A- and B-ring variations within the flavone-7-O-glucuronides did not affect the enzymes activity. Results were compared to computational binding studies on human -glucuronidase. Additionally, molecular modeling and dynamic studies were performed to obtain detailed insight into the binding and cleavage mode of the substrate at the active site of the human -glucuronidase.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHENOLIC-COMPOUNDS; QUERCETIN GLUCURONIDES; HIGH-THROUGHPUT; METABOLITES; ANALOGS; BRAIN; deglucuronidation; flavonoid glucuronides; inflammation; monocytes; molecular dynamics |
| Subjects: | 600 Technology > 610 Medical sciences Medicine |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer) Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 19 Jun 2019 09:12 |
| Last Modified: | 19 Jun 2019 09:14 |
| URI: | https://pred.uni-regensburg.de/id/eprint/5091 |
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