Note to users. If you're seeing this message, it means that your browser cannot find this page's style/presentation instructions -- or possibly that you are using a browser that does not support current Web standards. Find out more about why this message is appearing, and what you can do to make your experience of our site the best it can be.

Site Tools

  • AAAS
  • Subscribe
  • Feedback

Site Search

Search Advanced

Science 2 August 1985:
Vol. 229. no. 4712, pp. 472 - 475
DOI: 10.1126/science.4012327
Prev | Table of Contents | Next

Articles

Science, Vol 229, Issue 4712, 472-475
Copyright © 1985 by American Association for the Advancement of Science

articles

trans-4-Hydroxy-2-hexenal: a reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine

HJ Segall, DW Wilson, JL Dallas, and WF Haddon

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.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Endogenous Glutathione Conjugates: Occurrence and Biological Functions.
W. Wang and N. Ballatori (1998)
Pharmacol. Rev. 50, 335-356
   Abstract »    Full Text »    PDF »
4-Hydroxyhexenal Is a Potent Inducer of the Mitochondrial Permeability Transition.
B. S. Kristal, B. K. Park, and B. P. Yu (1996)
J. Biol. Chem. 271, 6033-6038
   Abstract »    Full Text »    PDF »


To Advertise     Find Products

Science. ISSN 0036-8075 (print), 1095-9203 (online)