Trans-4-hydroxy-2-hexenal: A reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine

H. J. Segall, Dennis W Wilson, J. L. Dallas, William F. Haddon

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Abstract

The toxicity of macrocyclic pyrrolizidine alkaloids in the livers of man and animals has been attributed to the formation of reactive pyrroles from dihydropyrrolizines. Now a novel metabolite, trans-4-hydroxy-2-hexenal, has been isolated from the macrocyclic pyrrolizidine alkaloid senecionine, in an in vitro hepatic microsomal system. Other alkenals such as trans-4-hydroxy-2- nonenal have previously been isolated from microsomal systems when treated with halogenated hydrocarbons or subjected to lipid peroxidation. The in vivo pathology caused by trans-4-hydroxy-2-hexenal appears to be identical to that previously attributed to reactive pyrroles. There are similarities between the toxic effects of this alkenal and those of centrilobular hepatotoxins such as CCl4 and other alkenals formed during lipid peroxidation.

Original languageEnglish (US)
Pages (from-to)472-475
Number of pages4
JournalScience
Volume229
Issue number4712
StatePublished - 1985

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Pyrrolizidine Alkaloids
Pyrroles
Lipid Peroxidation
Halogenated Hydrocarbons
Poisons
Liver
Pathology
senecionine
4-hydroxy-2-hexenal
In Vitro Techniques
4-hydroxy-2-nonenal

ASJC Scopus subject areas

  • General

Cite this

Trans-4-hydroxy-2-hexenal : A reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine. / Segall, H. J.; Wilson, Dennis W; Dallas, J. L.; Haddon, William F.

In: Science, Vol. 229, No. 4712, 1985, p. 472-475.

Research output: Contribution to journalArticle

Segall, H. J. ; Wilson, Dennis W ; Dallas, J. L. ; Haddon, William F. / Trans-4-hydroxy-2-hexenal : A reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine. In: Science. 1985 ; Vol. 229, No. 4712. pp. 472-475.
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