SUGGESTED MECHANISMS FOR THE PRODUCTION OF 4-HYDROXY-2-NONENAL FROM THE AUTOXIDATION OF POLYUNSATURATED FATTY-ACIDS

被引:191
作者
PRYOR, WA
PORTER, NA
机构
[1] Biodynamics Institute, Louisiana State University, Baton Rouge
[2] Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke University, Durham
关键词
4-hydroxy-2-nonenal; Aldehyde; Free radicals; Hydroperoxide; Lipid peroxidation;
D O I
10.1016/0891-5849(90)90153-A
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Autoxidation of certain polyunsaturated fatty acids (PUFA) produces 4-hydroxy-2-nonenal (HNE). Of all of the many products produce during PUFA autoxidation, HNE is one of the more interesting. It is remarkably cytotoxic, and appears to play a role in certain types of pathology. This manuscript suggests, for the first time, mechanisms that rationalize the production of HNE from PUFA that undergo autoxidation. The mechanisms requires, in agreement with the facts, an n-6 fatty acid and iron catalysis. © 1990.
引用
收藏
页码:541 / 543
页数:3
相关论文
共 9 条
  • [1] Esterbauer, Benedetti, Lang, Fulceri, Fauler, Comporti, Studies on the mechanism of formation of 4-hydroxy-nonenal during microsomal lipid peroxidation, Biochemica et Biophysica Acta, 876, pp. 154-156, (1986)
  • [2] Esterbauer, Zollner, Schaur, Aldehydes formed by lipid peroxidation: mechanisms of formation, occurrence, and determination, Membrane Lipid Oxidation, (1989)
  • [3] Esterbauer, Aldehydic products of lipid peroxidation, Free Radicals, Lipid Peroxidation and Cancer, (1982)
  • [4] Pryor, Stanley, Blair, Autoxidation of polyunsaturated fatty acids. Part II. A suggested mechanismfor the formation of TBA-reactive materials from prostaglandin-like endoperoxides, Lipids, 19, pp. 370-379, (1976)
  • [5] Porter, Autoxidation of polyunsaturated fatty acids: Initiation, propagation, and product distribution, Membrane Lipid Oxidation, 1, pp. 33-62, (1990)
  • [6] Gardner, Selke, Volatiles from thermal decomposition of isomeric methyl (12S, 13S)-(E)-12,13-epoxy-9-hydroperoxy-10-octadecenoates, Lipids, 19, pp. 375-380, (1984)
  • [7] Mosset, Yadagiri, Lumin, Capdevila, Flack, Arachidonate epoxygenase. Total synthesis of both enantiomers of 8,9- and 11,12-epoxyeicosatrienoic acid, Tetrahedron Lett., 27, pp. 6039-6040, (1986)
  • [8] Chabert, Ousset, Mioskowski, (3,3-Diisopropoxy-porpyl)-triphenylarsonium ylide: a new synthetic equivalent of ß-formyl vinyl anion, Tetrahedron Lett, 30, pp. 179-182, (1989)
  • [9] Johns, Murphy, Patterson, Wooster, Novel probe for free-radical intermediates, J. Chem. Soc. Chem. Comm., 1238-1240, (1987)