title: Syntheses of ferulic acid derivatives and their suppressive effects on cyclooxygenase-2 promoter activity.
abstract: Novel ferulic acid derivatives in which feruloyl groups were attached to the hydroxyl groups of myo-inositol 1,3,5-orthoformate derivatives were synthesized. These feruloyl-myo-inositols suppressed the cyclooxygenase-2 (COX-2) promoter activity in a concentration-dependent manner. Among the examined compounds, compound 9 showed the highest activity. A treatment with 100 microM of compound 9 for 24 h resulted in a 50% decrease of COX-2 promoter activity without marked cytotoxicity. Both the molecular structure in which two ferulic acid moieties are facing each other and the molecular hydrophobicity may be essential for the suppression of COX-2 promoter activity.
authors.affiliation: Industrial Technology Center of Wakayama Prefecture, 60 Ogura, 649-6261, Wakayama, Japan.
authors.forename: Asao
authors.initials: A
authors.lastname: Hosoda
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Ozaki
authors.forename: Ayumi
authors.initials: A
authors.lastname: Kashiwada
authors.forename: Michihiro
authors.initials: M
authors.lastname: Mutoh
authors.forename: Keiji
authors.initials: K
authors.lastname: Wakabayashi
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Mizuno
authors.forename: Eisaku
authors.initials: E
authors.lastname: Nomura
authors.forename: Hisaji
authors.initials: H
authors.lastname: Taniguchi
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D003373:Coumaric Acids / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D015971:Gene Expression Regulation, Enzymologic / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D011401:Promoter Regions, Genetic / Q000187:drug effects*; D011451:Prostaglandin-Endoperoxide Synthases / Q000235:genetics*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D003373:Coumaric Acids; D016861:Cyclooxygenase Inhibitors; C004999:ferulic acid; D011451:Prostaglandin-Endoperoxide Synthases