Synthesis of eugenol derivatives and its anti-inflammatory activity against skin inflammation

Abstract

Eugenol is a phytochemical present in aromatic plants has generated considerable interest in the pharmaceutical industries mainly in cosmetics. A series of eugenol esters (ST1-ST7) and chloro eugenol (<i>ST8</i>) have been synthesized. The structures of newly synthesized compounds were confirmed by ¹H and ¹³C NMR and mass spectrometry. In an effort to evaluate the pharmacological activity of eugenol derivatives, we explored its anti-inflammatory potential against skin inflammation using <i>in-vitro</i> and <i>in-vivo</i> bioassay. Synthesized derivatives significantly inhibited the production of pro-inflammatory cytokines against LPS-induced inflammation in macrophages. Among all derivatives, <i>ST8</i> [Chloroeugenol (6-chloro, 2-methoxy-4-(prop-2-en-1-yl)-phenol)] exhibited most potent anti-inflammatory activity without any cytotoxic effect. We have further evaluated the efficacy and safety in in-vivo condition. <i>ST8</i> exhibited significant anti-inflammatory activity against TPA-induced skin inflammation without any skin irritation effect on experimental animals. These findings suggested that <i>ST8</i> may be a useful therapeutic candidate for the treatment of skin inflammation.