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J Biol Chem, Vol. 273, Issue 22, 13605-13612, May 29, 1998
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From the F2-isoprostanes are
prostaglandin F2-like compounds that are formed
nonenzymatically by free radical-induced oxidation of arachidonic acid.
We explored whether oxidation of docosahexaenoic acid (C22:6 Departments of Pharmacology, Pathology, and
Medicine, Vanderbilt University, Nashville, Tennessee 37232, the
¶ Departments of Pathology and Neurology and the Sanders-Brown
Center of Aging, University of Kentucky, Lexington, Kentucky 40536, and the Departments of Pediatrics and Pharmacology, Research
Center of Hôpital Ste. Justine, 3175 Côte Ste. Catherine,
Montreal, Québec H3T IC5, Canada
3),
which is highly enriched in the brain, led to the formation of
F2-isoprostane-like compounds, which we term F4-neuroprostanes. Oxidation of docosahexaenoic acid
in vitro yielded a series of compounds that were
structurally established to be F4-neuroprostanes using a
number of mass spectrometric approaches. The amounts formed exceeded
levels of F2-isoprostanes generated from arachidonic acid
by 3.4-fold. F4-neuroprostanes were detected esterified in
normal whole rat brain and newborn pig cortex at a level of 7.0 ± 1.4 ng/g and 13.1 ± 8 ng/g, respectively. Furthermore, F4-neuroprostanes could be detected in normal human
cerebrospinal fluid and levels in patients with Alzheimer's disease
(110 ± 12 pg/ml) were significantly higher than age-matched
controls (64 ± 8 pg/ml) (p < 0.05).
F4-neuroprostanes may provide a unique marker of oxidative
injury to the brain and could potentially exert biological activity.
Furthermore, the formation of F4-neuroprostane-containing aminophospholipids might adversely effect neuronal function as a result
of alterations they induce in the biophysical properties of neuronal
membranes.
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