COVALENT INTERACTION OF DEHYDRORETRONECINE, A CARCINOGENIC METABOLITE OF PYRROLIZIDINE ALKALOID MONOCROTALINE, WITH CYSTEINE AND GLUTATHIONE

  • 1 January 1977
    • journal article
    • research article
    • Vol. 37  (9) , 3141-3144
Abstract
The covalent interaction of dehydroretonecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione, was investigated. Dehydroretronecine was allowed to react with cysteine and glutathione in an in vitro system of phosphate buffer solutions. The reaction products were identified structurally by chromatographic, NMR, IR, UV and mass spectral analysis. These data indicate that the reaction products are the sulfhydryl linked 7-thiocysteine-dehydroretronecine and 7-thioglutathione-dehydroretronecine. Active alkylation of sulfhydryl groups is a possible mechanism by which these alkaloids interact with cellular components.

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