The Lecanindoles, Nonsteroidal Progestins From the Terrestrial Fungus Verticillium Lecanii 6144

J Nat Prod. 2009 Nov;72(11):1944-8. doi: 10.1021/np9004882.

Abstract

Four new indolosesquiterpenes, lecanindoles A-D (1-4), were isolated from fermentations of the terrestrial fungus Verticillium lecanii 6144. The structures of compounds 1-4 were elucidated from analysis of spectroscopic data. Compound 2 was reduced to give 4 and its isomer 5. Compound 4 was found to be a potent and selective progesterone receptor agonist with an EC50 of 1.1 +/- 0.4 nM in a cell-based luciferase reporter assay.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Chlorocebus aethiops
  • Female
  • Humans
  • Hypocreales / chemistry*
  • Indoles / chemistry
  • Indoles / isolation & purification*
  • Indoles / pharmacology
  • Luciferases / metabolism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Progestins / chemistry
  • Progestins / isolation & purification*
  • Progestins / pharmacology
  • Receptors, Progesterone / agonists*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • Indoles
  • Progestins
  • Receptors, Progesterone
  • Sesquiterpenes
  • Luciferases