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Molecular Pharmacology, Vol 6, 402-406, Copyright © 1970 by the American Society for Pharmacology and Experimental Therapeutics

Metabolic Conversion of Heliotridine-Based Pyrrolizidine Alkaloids to Dehydroheliotridine

M. V. JAGO 1, J. A. EDGAR 2, L. W. SMITH 2, and C. C. J. CULVENOR 2

1 Animal Health Research Laboratory, Division of Animal Health, Commonwealth Scientific and Industrial Research Organization, Parkville, Victoria, Australia
2 Division of Applied Chemistry, Commonwealth Scientific and Industrial Research Organization, Melbourne, Victoria, Australia

The heliotridine-based pyrrolizidine alkaloids lasiocarpine and heliotrine were metabolized in vitro by rat liver microsomes to one main chloroform-extractable and water-soluble pyrrolic derivative, which was isolated and idenitified as dehydroheliotridine (6,7-dihydro-7agr-hydroxy-1-hydroxymethyl-5H-pyrrolizine) by chromatography and nuclear magnetic resonance and mass spectroscopy. Only trace amounts of this metabolite were formed from the N-oxides of lasiocarpine or heliotrine, and it was not formed from supinine.

Note:
ACKNOWLEDGMENT We wish to thank Miss K. Moss, for technical assistance.

Submitted on April 13, 1970






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