Novel 11-norbetaenone isolated from an entomopathogenic fungus Lecanicillium antillanum

Bioorg Med Chem Lett. 2017 May 1;27(9):1978-1982. doi: 10.1016/j.bmcl.2017.03.019. Epub 2017 Mar 11.

Abstract

A novel nor-betaenone compound, 11-norbetaenone (1), was isolated from the culture broth of an entomopathogenic fungus Lecanicillium antillanum. The structure was determined on the basis of 1D and 2D NMR spectroscopic data. The absolute stereochemistry of 1 was further confirmed by X-ray single crystallography analysis. It is the first secondary metabolite reported from the species Lecanicillium antillanum. And it is also the first time that a betaenone-type compound was isolated from the genus Lecanicillium. Furthermore, 11-norbetaenone (1) displayed significant anti-angiogenic effect by suppressing tube formation.

Keywords: Anti-angiogenic effect; Betaenone; Lecanicillium antillanum; Polyketide synthase; Secondary metabolite.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemistry*
  • Angiogenesis Inhibitors / isolation & purification
  • Angiogenesis Inhibitors / pharmacology*
  • Crystallography, X-Ray
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Endothelial Progenitor Cells / cytology
  • Endothelial Progenitor Cells / drug effects
  • Humans
  • Hypocreales / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular

Substances

  • 11-norbetaenone
  • Angiogenesis Inhibitors
  • Diterpenes