(-)-Epiafzelechin: cyclooxygenase-1 inhibitor and anti-inflammatory agent from aerial parts of Celastrus orbiculatus

Planta Med. 1999 Jun;65(5):460-2. doi: 10.1055/s-2006-960813.

Abstract

An inhibitor of cyclooxygenase (COX)-1 activity of prostaglandin H2 synthase was isolated from aerial parts of Celastrus orbiculatus Thunb. (Celastraceae), an oriental folk medicine for rheumatoid arthritis by activity-guided column chromatographic methods. The COX inhibitor was identified as (-)-epiafzelechin, a member of flavan-3-ols by the structural analysis with HR-EI-mass, 1H-NMR and 13C-NMR spectral data. The compound exhibited a dose-dependent inhibition on the COX activity with an IC50 value of 15 microM. (-)-Epiafzelechin exhibited about 3-fold weaker inhibitory potency on the enzyme activity than indomethacin as a positive control. (-)-Epiafzelechin exhibited significant anti-inflammatory activity on carrageenin-induced mouse paw edema when the compound (100 mg/kg) was orally administrated at 1 h before carrageenin treatment.

Publication types

  • Letter
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Carrageenan
  • Catechin / analogs & derivatives*
  • Catechin / chemistry
  • Catechin / isolation & purification
  • Catechin / pharmacology
  • Cyclooxygenase 1
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / isolation & purification
  • Cyclooxygenase Inhibitors / pharmacology*
  • Edema / chemically induced
  • Edema / drug therapy
  • Isoenzymes / metabolism*
  • Male
  • Medicine, Chinese Traditional
  • Membrane Proteins
  • Mice
  • Mice, Inbred ICR
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plants, Medicinal*
  • Prostaglandin-Endoperoxide Synthases / metabolism*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclooxygenase Inhibitors
  • Isoenzymes
  • Membrane Proteins
  • Plant Extracts
  • epiafzelechin
  • Catechin
  • Carrageenan
  • Cyclooxygenase 1
  • Prostaglandin-Endoperoxide Synthases
  • Ptgs1 protein, mouse