Item type: | Article | ||||
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Journal or Publication Title: | European journal of medicinal chemistry | ||||
Publisher: | Elsevier | ||||
Volume: | 45 | ||||
Number of Issue or Book Chapter: | 6 | ||||
Page Range: | pp. 2206-2213 | ||||
Date: | 2010 | ||||
Additional Information (public): | CAN 153:62048 26-4 Biomolecules and Their Synthetic Analogs 6754-58-1P Role: PAC (Pharmacological activity), RCT (Reactant), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation), RACT (Reactant or reagent) (synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect); 62014-87-3P (Helichrysetin); 189299-05-6P; 688359-98-0P (Xanthohumol H); 688360-01-2P; 688360-02-3P; 852638-41-6P; 1034276-32-8P; 1207843-45-5P; 1228673-64-0P; 1228673-65-1P; 1228673-66-2P; 1228673-67-3P; 1228673-68-4P; 1228673-69-5P Role: PAC (Pharmacological activity), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect); 123-11-5; 373-61-5 (Boron trifluoride-acetic acid (1:2); 480-66-0; 5533-00-6; 6515-06-6; 6515-21-5; 25983-76-0; 404597-94-0; 955950-40-0; 1044743-44-3 Role: RCT (Reactant), RACT (Reactant or reagent) (synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect); 2161-86-6P; 3098-38-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) | ||||
Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) | ||||
Identification Number: |
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Keywords: | CD antigens Role: BSU (Biological study, unclassified), BIOL (Biological study) (CD54, TNFalpha induced expression inhibitor synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) Cell adhesion molecules Role: BSU (Biological study, unclassified), BIOL (Biological study) (ICAM-1 (intercellular adhesion mol. 1), TNFalpha induced expression inhibitor synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) Tumor necrosis factors Role: BSU (Biological study, unclassified), BIOL (Biological study) (ICAM-1 induced expression inhibitor synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) Structure-activity relationship (antioxidant synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) Structure-activity relationship (inflammation-inhibiting synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) Antioxidants (pharmaceutical synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) Anti-inflammatory agents Cytotoxicity Human (synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacol. effect) Chalcones Role: PAC (Pharmacological activity), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the ph chalcone deriv synthesis condensation reaction antioxidant antiinflammatory agent chalcone deriv synthesis condensation reaction cytotoxicity chalcone deriv synthesis condensation reaction | ||||
Dewey Decimal Classification: | 500 Science > 570 Life sciences 500 Science > 540 Chemistry & allied sciences | ||||
Status: | Published | ||||
Refereed: | Yes, this version has been refereed | ||||
Created at the University of Regensburg: | Yes | ||||
Item ID: | 17170 |
Abstract
Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalcone, both phase II metabolites of xanthohumol in rats. Also a principally new chalcone, 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone, structurally derived from helichrysetin by introducing a second coumaroyl substructure at C-3' was synthesized. Furthermore new chalcones were ...
Abstract
Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalcone, both phase II metabolites of xanthohumol in rats. Also a principally new chalcone, 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone, structurally derived from helichrysetin 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. Compd. I showed the highest cytotoxic activity against HeLa cells with an IC50 value of 7.3 +- 0.4 micro M. Anti-oxidative effects were detd. in the ORAC assay and revealed very strong activity for I and 3-methoxyhelichrysetin exhibiting 7.7 +- 0.3 and 6.0 +- 1.3 Trolox equiv., resp. The anti-inflammatory activity of all compds. 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 and 3-hydroxyxanthohumol H being the most active. At 10 micro M the TNFalpha induced expression of ICAM-1 was significantly reduced to 65.8 and 69.6% of control, resp.
Metadata last modified: 24 May 2018 12:16