Vogel, Susanne and Barbic, Matej and Juergenliemk, Guido and Heilmann, Joerg (2010) Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 45 (6). pp. 2206-2213. ISSN 0223-5234, 1768-3254
Full text not available from this repository.Abstract
Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone (1) and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalkon (2), both phase II metabolites of xanthohumol in rats, also a principally new chalcone 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone (3), structurally derived from helichrysetin (4) by introducing a second coumaroyl substructure at C-3' was synthesized. Furthermore new chalcones were synthesized by combination of the B-Ring fragments of helichrysetin, xanthohumol, xanthohumol C and xanthohumol H with ferulic or caffeic acid moieties in Ring A. Compound 3 showed the highest cytotoxic activity against HeLa cells with an IC50 value of 7.3 +/- 04 mu M. Anti-oxidative effects were determined in the ORAC assay and revealed very strong activity for 3 and 3-methoxyhelichrysetin (6) exhibiting 7.7 +/- 0.3 and 6.0 +/- 1.3 Trolox equivalents, respectively. The anti-inflammatory activity of all compounds was measured in an in vitro ICAM-1 assay with human microvascular endothelial cells (HMEC-1) and compared with the activity of other structurally related chalcones. The results showed increasing anti-inflammatory activity for the new synthetic chalcones exhibiting a caffeoyl substructure with 3-hydroxyhelichrysetin (5) and 3-hydroxyxanthohumol H (14) being the most active. At 10 mu M the TNF alpha induced expression of ICAM-1 was significantly reduced to 65.8 and 69.6% of control, respectively.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HUMAN LIVER-MICROSOMES; NF-KAPPA-B; BIOLOGICAL EVALUATION; PRENYLATED CHALCONES; HUMULUS-LUPULUS; CANCER-CELLS; XANTHOHUMOL; HOPS; PROLIFERATION; EXPRESSION; Xanthohumol; Chalcones; 3 '-Coumaroyl-2 ',4,4 '-trihydroxy-6 '-methoxychalcone; Anti-oxidative; Cytotoxic; Anti-inflammatory |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Jul 2020 05:32 |
| Last Modified: | 29 Jul 2020 05:32 |
| URI: | https://pred.uni-regensburg.de/id/eprint/24604 |
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