Syntheses of ferulic acid derivatives and their suppressive effects on cyclooxygenase-2 promoter activity.
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.
Hosoda
Asao
A
Industrial Technology Center of Wakayama Prefecture, 60 Ogura, 649-6261, Wakayama, Japan.
Ozaki
Yoshihiko
Y
Kashiwada
Ayumi
A
Mutoh
Michihiro
M
Wakabayashi
Keiji
K
Mizuno
Kazuhiko
K
Nomura
Eisaku
E
Taniguchi
Hisaji
H
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
D000894:Anti-Inflammatory Agents, Non-Steroidal; D003373:Coumaric Acids; D016861:Cyclooxygenase Inhibitors; C004999:ferulic acid; D011451:Prostaglandin-Endoperoxide Synthases