Identity of a biliary metabolite formed from monocrotaline in isolated, perfused rat liver

Toxicon. 1991;29(4-5):409-15. doi: 10.1016/0041-0101(91)90015-j.

Abstract

A pneumotoxic pyrrolic metabolite, previously isolated from the bile when rat liver was perfused with the pyrrolizidine alkaloid, monocrotaline, has been identified as 7-glutathionyl-dehydroretronecine. The metabolite showed a TLC spot and HPLC peak corresponding with the latter compound, and a procedure for replacing the thioether group with an ethoxy group converted the metabolite to dehydroretronecine 7-ethyl ether, confirming that the glutathionyl moiety was attached to the 7-position of dehydroretronecine. The same metabolite was detected in bile from rat liver perfused with retrorsine, which is a diester alkaloid similar to monocrotaline, whereas it was not formed from heliotrine, an alkaloid lacking the 7-ester function.

MeSH terms

  • Animals
  • Bile / metabolism*
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Glutathione / metabolism*
  • In Vitro Techniques
  • Liver / metabolism*
  • Molecular Structure
  • Monocrotaline
  • Perfusion
  • Pyrrolizidine Alkaloids / metabolism*
  • Rats

Substances

  • Pyrrolizidine Alkaloids
  • glutathione-dehydro-retronecine conjugate
  • Monocrotaline
  • Glutathione