Compounds from the insect Blaps japanensis with COX-1 and COX-2 inhibitory activities

Bioorg Med Chem Lett. 2015 Jun 15;25(12):2469-72. doi: 10.1016/j.bmcl.2015.04.085. Epub 2015 Apr 30.

Abstract

Blapsols A-D (1-4), four new compounds possessing a 2,3-dihydrobenzo[b][1,4]dioxin group, together with five known N-acetyldopamine dimers (5-9), were isolated from Blaps japanensis. Their structures including the absolute configuration of (+)-1 were determined by means of spectroscopic and X-ray crystallographic methods. Chiral HPLC was used to separate (-)- and (+)-enantiomers of compounds 1-4, which were isolated from this insect as racemic mixtures. All the compounds were found to have inhibitory effects towards COX-2 with IC50 values in the range of 1.3-17.8μM.

Keywords: Blaps japanensis; COX-1; COX-2; Insects; N-Acetyldopamine dimers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Coleoptera / chemistry*
  • Coleoptera / metabolism
  • Crystallography, X-Ray
  • Cyclooxygenase 1 / chemistry*
  • Cyclooxygenase 1 / metabolism
  • Cyclooxygenase 2 / chemistry*
  • Cyclooxygenase 2 / metabolism
  • Cyclooxygenase Inhibitors / chemistry*
  • Dioxins / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Stereoisomerism

Substances

  • 2,3-dihydrobenzo(1,4)dioxin
  • Cyclooxygenase Inhibitors
  • Dioxins
  • Cyclooxygenase 1
  • Cyclooxygenase 2