title: Anti-inflammatory activities of selected synthetic homoisoflavanones.
abstract: Four homoisoflavanones of the 3-benzylidene-4-chromanone type, some of which were previously isolated from Caesalpinia pulcherrima, were synthesised to determine their anti-inflammatory activity and cytotoxicity. A range of four different homoisoflavanones (compounds 4a-4d) were synthesised from the corresponding substituted phenols. ¹H- and ¹³C-NMR data together with high-resolution mass spectroscopy data were employed to elucidate the structures. Anti-inflammatory activity was determined in mice with acute croton oil-induced auricular dermatitis. In vitro cytotoxicity was tested against a Chinese hamster ovarian cell line using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide (MTT) assay. Compound 4a exhibited a tendency to inhibit oedema in a dose-dependent manner after 3 and 6 h of treatment. Compounds 4b-4d also inhibited oedema, although a clear dose-response relationship was not observed. Compounds 4a-4c were found to be less cytotoxic than compound 4d. Compound 4b was the least cytotoxic. Compounds 4a-4d exhibited anti-inflammatory activity and varying levels of cytotoxicity.
authors.affiliation: School of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa.
authors.forename: Mahidansha M
authors.initials: MM
authors.lastname: Shaikh
authors.forename: Hendrik G
authors.initials: HG
authors.lastname: Kruger
authors.forename: Johannes
authors.initials: J
authors.lastname: Bodenstein
authors.forename: Peter
authors.initials: P
authors.lastname: Smith
authors.forename: Karen
authors.initials: K
authors.lastname: du Toit
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use*; D016466:CHO Cells; D002855:Chromatography, Thin Layer; D006224:Cricetinae; D003872:Dermatitis / Q000188:drug therapy; D007529:Isoflavones / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008807:Mice, Inbred BALB C; D015394:Molecular Structure
chemical_list: D000893:Anti-Inflammatory Agents; D007529:Isoflavones