Identity of a biliary metabolite formed from monocrotaline in isolated, perfused rat liver.
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.
Mattocks
A R
AR
Toxicology Unit, Medical Research Council Laboratories, Carshalton, Surrey, U.K.
Croswell
S
S
Jukes
R
R
Huxtable
R J
RJ
D000818:Animals; D001646:Bile / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005978:Glutathione / Q000378:metabolism*; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism*; D015394:Molecular Structure; D016686:Monocrotaline; D010477:Perfusion; D011763:Pyrrolizidine Alkaloids / Q000378:metabolism*; D051381:Rats
D011763:Pyrrolizidine Alkaloids; C064161:glutathione-dehydro-retronecine conjugate; D016686:Monocrotaline; D005978:Glutathione