Bequinostatins A and B new inhibitors of glutathione S-transferase, produced by Streptomyces sp. MI384-DF12. Production, isolation, structure determination and biological activities

J Antibiot (Tokyo). 1993 Jun;46(6):914-20. doi: 10.7164/antibiotics.46.914.

Abstract

New benzo[a]naphthacenequinone metabolites, designated bequinostatins A and B, have been isolated from the culture broth of the benastatin-producing strain Streptomyces sp. MI384-DF12. The structures of bequinostatins A and B were determined by spectral analyses to be 5,6,8,13-tetrahydro-1,6,7,9,11-pentahydroxy-8,13-dioxo-3- pentylbenzo[a]naphthacene-2-carboxylic acid and 2-decarboxybequinostatin A, respectively. Bequinostatin A showed considerable inhibitory activity against human pi class glutathione S-transferase (GST pi).

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Benz(a)Anthracenes / chemistry
  • Benzoquinones / chemistry
  • Benzoquinones / isolation & purification*
  • Benzoquinones / pharmacology*
  • Chromatography, High Pressure Liquid
  • Fermentation
  • Glutathione Transferase / antagonists & inhibitors*
  • Magnetic Resonance Spectroscopy
  • Mice
  • Mice, Inbred BALB C
  • Naphthacenes / chemistry
  • Naphthacenes / isolation & purification*
  • Naphthacenes / pharmacology*
  • Quinones / chemistry
  • Quinones / isolation & purification*
  • Quinones / pharmacology*
  • Streptomyces / chemistry*
  • Structure-Activity Relationship

Substances

  • Benz(a)Anthracenes
  • Benzoquinones
  • Naphthacenes
  • Quinones
  • benastatin A
  • bequinostatin A
  • bequinostatin B
  • Glutathione Transferase