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

Nat Prod Res. 2020 Jan;34(2):251-260. doi: 10.1080/14786419.2018.1528585. Epub 2018 Dec 22.

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; inflammation; macrophage; mice; skin.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / pharmacology*
  • Cytokines / antagonists & inhibitors
  • Dermatitis / drug therapy*
  • Eugenol / analogs & derivatives
  • Eugenol / chemical synthesis*
  • Eugenol / pharmacology
  • Macrophages / drug effects
  • Macrophages / pathology
  • Phytochemicals / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Cytokines
  • Phytochemicals
  • Eugenol