Configuration of necine pyrroles--toxic metabolites of pyrrolizidine alkaloids.
The commonly accepted belief regarding the configuration of the major pyrrole metabolite of pyrrolizidine alkaloids has been revised. This paper provides evidence that a racemic mixture of (+/-) 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine is the product of the microsomal transformation of esters of heliotridine and retronecine instead of pure(+) or (-) enantiomers, commonly referred to as dehydroheliotridine and dehydroretronecine. The toxicological significance of these results is under investigation.
D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D066298:In Vitro Techniques; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D008968:Molecular Conformation; D011758:Pyrroles / Q000378:metabolism*; D011763:Pyrrolizidine Alkaloids / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D013237:Stereoisomerism
D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids