Covalent interaction of dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione

Kent Robertson, J. L. Seymour, M. T. Hsia, J. R. Allen

Research output: Contribution to journalArticle

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Abstract

The covalent interaction of dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione, has been 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, nuclear magnetic resonance, infrared, ultraviolet, 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.

Original languageEnglish (US)
Pages (from-to)3141-3144
Number of pages4
JournalCancer Research
Volume37
Issue number9
StatePublished - 1977
Externally publishedYes

Fingerprint

Monocrotaline
Pyrrolizidine Alkaloids
Glutathione
Cysteine
Alkylation
Alkaloids
Buffers
Magnetic Resonance Spectroscopy
Phosphates
dehydroretronecine

ASJC Scopus subject areas

  • Cancer Research
  • Oncology

Cite this

Covalent interaction of dehydroretronecine, a carcinogenic metabolite of the pyrrolizidine alkaloid monocrotaline, with cysteine and glutathione. / Robertson, Kent; Seymour, J. L.; Hsia, M. T.; Allen, J. R.

In: Cancer Research, Vol. 37, No. 9, 1977, p. 3141-3144.

Research output: Contribution to journalArticle

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