Colletoic acid, a novel 11beta-hydroxysteroid dehydrogenase type 1 inhibitor from Colletotrichum gloeosporioides SANK 21404

J Antibiot (Tokyo). 2008 Mar;61(3):136-41. doi: 10.1038/ja.2008.122.

Abstract

Colletoic acid, a novel 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) inhibitor, was found and isolated from the cultured broth of the producing fungus Colletotrichum gloeosporioides SANK 21404. Its structure was determined to be a novel acorene-type sesquiterpene by several spectroscopic methods. The absolute structure of colletoic acid was established using a modified Mosher's method and single-crystal X-ray diffraction analysis.

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
  • 11-beta-Hydroxysteroid Dehydrogenase Type 2 / antagonists & inhibitors
  • Chemical Phenomena
  • Chemistry, Physical
  • Colletotrichum / chemistry*
  • Colletotrichum / classification
  • Crystallography, X-Ray
  • Cyclopentanes / chemistry
  • Cyclopentanes / pharmacology*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / pharmacology*
  • Esters / chemical synthesis
  • Fermentation
  • Humans
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Sesquiterpenes
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology*

Substances

  • Cyclopentanes
  • Enzyme Inhibitors
  • Esters
  • Sesquiterpenes
  • Spiro Compounds
  • colletoic acid
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1
  • 11-beta-Hydroxysteroid Dehydrogenase Type 2