New quinones and hydroquinones from Malbranchea cinnamomea HKI 286 and HKI 296 and interaction with Tax/CREB expression system in yeast

J Antibiot (Tokyo). 2003 Nov;56(11):917-22. doi: 10.7164/antibiotics.56.917.

Abstract

In addition to malbranicin (1) and dihydromalbranicin (5), new substituted quinones 2, 3, 6 and hydroquinone 4 were isolated from the culture brothes of two strains of Malbranchea cinnamomea. The chemical constitutions of new metabolites 2, 3, 4 and 6 were elucidated by optical spectroscopy, mass spectrometry and 1D/2D NMR spectroscopy. 2 (7-methoxymalbranicin) at a concentration of 42 microM inhibited by 67% Tax/CREB-mediated expression of beta-galactosidase in a recombinant strain of Saccharomyces cerevisiae.

MeSH terms

  • Cyclic AMP Response Element-Binding Protein / drug effects*
  • Genes, pX / drug effects*
  • Hydroquinones / chemistry
  • Hydroquinones / isolation & purification*
  • Hydroquinones / pharmacology
  • Quinones / chemistry
  • Quinones / isolation & purification*
  • Quinones / pharmacology
  • Saccharomyces cerevisiae / drug effects*
  • Saccharomyces cerevisiae / enzymology
  • Structure-Activity Relationship

Substances

  • Cyclic AMP Response Element-Binding Protein
  • Hydroquinones
  • Quinones