Metabolism of illudin S, a toxic principle of Lampteromyces japonicus, by rat liver. I. Isolation and identification of cyclopropane ring-cleavage metabolites

Xenobiotica. 1990 Jul;20(7):671-81. doi: 10.3109/00498259009046883.

Abstract

1. Illudin S, a toxic principle of the basidiomycete Lampteromyces japonicus, was incubated with rat liver 9000 g supernatant and its metabolites studied. 2. Two metabolites, M1 and M2, were isolated and identified as cyclopropane ring-cleavage compounds by n.m.r., i.r. and mass spectral analyses. Moreover, M2 contained a chlorine atom. 3. On the basis of detailed analyses of the 2D n.m.r. spectra and differential nuclear Overhauser effect experiments, the previous assignments of the cyclopropane carbons of illudin S were revised.

MeSH terms

  • Animals
  • Antibiotics, Antineoplastic / metabolism*
  • Basidiomycota / analysis*
  • Chromatography, Thin Layer
  • Cyclopropanes / isolation & purification*
  • Liver / metabolism*
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Structure
  • Polycyclic Sesquiterpenes
  • Rats
  • Rats, Inbred Strains
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / metabolism
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • Antibiotics, Antineoplastic
  • Cyclopropanes
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • illudin S