Identification of metabolites of adonifoline, a hepatotoxic pyrrolizidine alkaloid, by liquid chromatography/tandem and high-resolution mass spectrometry

Rapid Commun Mass Spectrom. 2009 Dec;23(24):3907-16. doi: 10.1002/rcm.4329.

Abstract

Hepatotoxic pyrrolizidine alkaloid (HPA)-containing plants have always been a threat to human and livestock health worldwide. Adonifoline, a main HPA in Senecio scandens Buch.-Ham. ex D. Don (Qianli guang), was used officially as an infusion in cases of oral and pharyngeal infections in China. In this study in vivo metabolism of adonifoline was studied for the first time by identifying the metabolites of adonifoline present in bile, urine and feces of rats using liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS(n)) (ion trap) as well as liquid chromatography/electrospray ionization high-resolution mass spectrometry (LC/ESI-HRMS) (quadrupole-time of flight). In total 19 metabolites were identified and, among them, retronecine-N-oxides were confirmed by matching their fragmentation patterns with their fully characterized synthetic compounds. These metabolites are all involved in both phase I and phase II metabolic processes and the principal in vivo metabolism pathways of adonifoline were proposed.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bile / chemistry
  • Chromatography, Liquid / methods*
  • Feces / chemistry
  • Lactones / blood
  • Lactones / chemistry*
  • Lactones / metabolism*
  • Lactones / urine
  • Male
  • Pyrrolizidine Alkaloids / blood
  • Pyrrolizidine Alkaloids / chemistry*
  • Pyrrolizidine Alkaloids / metabolism*
  • Pyrrolizidine Alkaloids / urine
  • Random Allocation
  • Rats
  • Rats, Sprague-Dawley
  • Senecio / chemistry*
  • Tandem Mass Spectrometry / methods*

Substances

  • Lactones
  • Pyrrolizidine Alkaloids
  • adonifoline