NF-kappaB-inhibiting naphthopyrones from the Fijian echinoderm Comanthus parvicirrus

J Nat Prod. 2008 Jan;71(1):106-11. doi: 10.1021/np070290y. Epub 2007 Dec 19.

Abstract

The two naphthopyrones 6-methoxycomaparvin (1) and 6-methoxycomaparvin 5-methyl ether (2) were isolated from a bioactive methanol-soluble extract of the Fijian echinoderm Comanthus parvicirrus. Their structures were assigned on the basis of spectroscopic methods. X-ray diffraction analysis was used to confirm the structure of 1. Both compounds were tested for their potential to inhibit the activation of the transcription factor NF-kappaB, which plays an important role in cancer development and inflammation, and the mechanism of action of the two compounds was investigated. Both naphthopyrones 1 and 2 completely inhibit TNF-alpha-induced NF-kappaB activation at a concentration of 300 microM by inhibiting the enzymatic activity of the kinase IKKbeta.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Base Sequence
  • Crystallography, X-Ray
  • Echinodermata / chemistry*
  • Fiji
  • Humans
  • I-kappa B Kinase / antagonists & inhibitors
  • Molecular Conformation
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors*
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology*
  • Pyrones / chemistry
  • Pyrones / isolation & purification*
  • Pyrones / pharmacology*
  • Tumor Necrosis Factor-alpha / pharmacology

Substances

  • 6-methoxycomaparvin
  • 6-methoxycomaparvin 5-methyl ether
  • NF-kappa B
  • Naphthalenes
  • Pyrones
  • Tumor Necrosis Factor-alpha
  • I-kappa B Kinase