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Flavonoids possess anti-inflammatory activity in vitro and in vivo. In order to find the anti-inflammatory flavone derivatives having optimum chemical structures, various flavones were previously synthesized and evaluated for their inhibitory activity of prostaglandin E(2) (PGE(2)) production from lipopolysaccharide (LPS)-treated mouse macrophage cell line, RAW 264.7 cells. Through this screening procedure, 2',4',7-trimethoxyflavone (TMF) was selected for further pharmacological study. From the present investigation, it was found that TMF potently inhibited PGE(2) production from LPS-treated RAW cells with an IC(50) of 0.48 microM, compared to the IC(50) values of 0.07 and 1.09 microM for NS-398 and wogonin. TMF, however, did not inhibit cyclooxygenase-2 (COX-2) activity or COX-2 expression level. Instead, TMF was proved to be a phospholipase A(2) (PLA(2)) inhibitor. The IC(50) values of TMF against secretory PLA(2)-IIA (sPLA(2)-IIA) and cytosolic PLA(2) (cPLA(2)) were 70.5 and 70.4 microM, respectively. At doses of 10-250 microg/ear, TMF also showed in vivo anti-inflammatory activity by topical application against mouse croton oil-induced ear edema assay, suggesting a potential for new anti-inflammatory agent.

Inhibition of Prostaglandin Production by a Structurally-Optimized Flavonoid Derivative, 2',4',7-Trimethoxyflavone and Cellular Action Mechanism