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 (ST8) 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 in-vitro and in-vivo bioassay. Synthesized derivatives significantly inhibited the production of pro-inflammatory cytokines against LPS-induced inflammation in macrophages. Among all derivatives, ST8 [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. ST8 exhibited significant anti-inflammatory activity against TPA-induced skin inflammation without any skin irritation effect on experimental animals. These findings suggested that ST8 may be a useful therapeutic candidate for the treatment of skin inflammation.

Keywords:

• Eugenol
• skin
• macrophage
• inflammation
• mice

Acknowledgments

The authors are grateful to Director of the institute for kind support during the progress of the work.

Disclosure statement

The authors declare that there is no conflict of interests regarding the publication of this paper.

Additional information

Funding

The research was supported by Council of Scientific and Industrial Research (CSIR), New Delhi, India for financial support through BSC-0203 and HCP-007.