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J. Biol. Chem., Vol. 269, Issue 42, 26066-26075, Oct, 1994
H Rubbo, R Radi, M Trujillo, R Telleri, B Kalyanaraman, S Barnes, M Kirk and BA Freeman
Superoxide (O2-.), nitric oxide (.NO), and their reaction product
peroxynitrite (ONOO-) have all been shown to independently exert toxic
target molecule reactions. Because these reactive species are often
generated in excess during diverse inflammatory and other pathologic
circumstances, we assessed the influence of .NO on membrane lipid
peroxidation induced by O2-., H2O2, and .OH derived from xanthine oxidase
(XO) and by ONOO-. Experimental conditions in lipid oxidation systems were
adjusted to yield different rates of delivery of .NO, relative to rates of
O2-. and H2O2 generation, by infusion of either .NO or via .NO released
from S-nitroso-N-acetylpenicillamine or S- nitrosoglutathione. Peroxidation
of phosphatidylcholine liposomes was assessed by formation of
thiobarbituric acid-reactive products and by liquid chromatography-mass
spectrometry. Liposomes exposed to XO- derived reactive species in the
presence of .NO exhibited both stimulation and inhibition of lipid
peroxidation, depending on the ratio of the rates of reactive oxygen
species production and .NO introduction into reaction systems. Nitric oxide
alone did not induce lipid peroxidation. Linolenic acid emulsions
peroxidized by XO-derived reactive species showed similar dose-dependent
regulation of lipid peroxidation by .NO. Mass spectral analysis of
oxidation products showed formation of nitrito-, nitro-, nitrosoperoxo-,
and/or nitrated lipid oxidation adducts, demonstrating that .NO serves as a
potent terminator of radical chain propagation reactions. Electron spin
resonance (ESR) analysis of incubation mixtures provided no evidence for
formation of paramagnetic iron-lipid-nitric oxide complexes in reaction
systems. Peroxynitrite-dependent lipid peroxidation, which predominantly
occurs by metal-independent mechanisms, was also inhibited by .NO.
Peroxynitrite-mediated benzoate hydroxylation was partially inhibited by
.NO, inferring reaction between .NO and ONOOH. It is concluded that .NO can
both stimulate O2-./H2O2/.OH-induced lipid oxidation and mediate
oxidant-protective reactions in membranes at higher rates of .NO
production, with the prooxidant versus antioxidant outcome critically
dependent on relative concentrations of individual reactive species.
Prooxidant reactions of .NO will occur after O2-. reaction with .NO to
yield potent secondary oxidants such as ONOO- and the antioxidant effects
of .NO a consequence of direct reaction with alkoxyl and peroxyl radical
intermediates during lipid peroxidation, thus terminating lipid radical
chain propagation reactions.
Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives
Department of Anesthesiology, University of Alabama at Birmingham 35233.
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