A novel carbon skeletal trichothecane, tenuipesine A, isolated from an entomopathogenic fungus, Paecilomyces tenuipes

Org Lett. 2004 Nov 25;6(24):4531-3. doi: 10.1021/ol048141j.

Abstract

Tenuipesine A (1), a novel trichothecane with an unprecedented carbon-migrated skeleton that embodies of a cyclopropane ring, was isolated from cultivated fruiting bodies of Paecilomyces tenuipes (Isaria japonica), a popular entomopathogenic fungi employed in folk medicine and health foods in China, Korea, and Japan. The structure was determined on the basis of two-dimensional NMR data. Its stereochemistry was elucidated by spectroscopic data and the chemical transformation of the coexisting trichothecene, 4beta-acetoxy-12,13-epoxytrichothec-9-ene-3alpha,15-diol (2). [structure: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclopropanes
  • Magnetic Resonance Spectroscopy
  • Medicine, Traditional
  • Molecular Structure
  • Paecilomyces / chemistry*
  • Trichothecenes / chemistry*
  • Trichothecenes / isolation & purification

Substances

  • Cyclopropanes
  • Trichothecenes
  • tenuipesine A
  • cyclopropane