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 CCl 4 and other alkenals formed during lipid peroxidation.
Keywords
Pyrrolizidine alkaloidPyrrolizidineMetaboliteLipid peroxidationChemistryBiochemistryAlkaloidMicrosomeStereochemistryIn vitroOxidative stress
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Publication Info
- Year
- 1985
- Type
- article
- Volume
- 229
- Issue
- 4712
- Pages
- 472-475
- Citations
- 82
- Access
- Closed
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Cite This
H.J. Segall,
Dennis W. Wilson,
Javier Dallas
et al.
(1985).
<i>Trans</i> -4-Hydroxy-2-Hexenal: a Reactive Metabolite from the Macrocyclic Pyrrolizidine Alkaloid Senecionine.
Science
, 229
(4712)
, 472-475.
https://doi.org/10.1126/science.4012327
Identifiers
- DOI
- 10.1126/science.4012327