The formation of 6,7-dihydro-7-hydroxy-1-hydroxy-methyl-5H-pyrrolizine, a metabolite of pyrrolizidine alkaloids

In vitro metabolism of senecionine with rat hepatic microsomes was studied. The main pyrrolic metabolite, 6,7-dihydro-7-hydroxy-1-hydroxy-methyl-5H-pyrrolizine was isolated by preparative high performance liquid chromatography (PRP-1 column) and examined by mass spectrometry. Results of the incubation performed in the presence of H218O indicated that both hydroxyl groups of the metabolite came from the solvent. Thus, formation of the pyrrolic metabolite is accomplished by alkyl-oxygen fission of both bonds C7-O and C9-O of the dehydroalkaloid, an intermediate supposedly formed during metabolic transformation of pyrrolizidine alkaloids (PAs).