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J Biol Chem, Vol. 274, Issue 35, 24787-24798, August 27, 1999
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From the One of the earliest steps in the
development of the atherosclerotic lesion is the accumulation of
monocyte/macrophages within the vessel wall. Oxidized lipids present in
minimally modified-low density lipoproteins (MM-LDL) contribute to this
process by activating endothelial cells to express monocyte-specific
adhesion molecules and chemoattractant factors. A major focus of our
group has been the isolation and characterization of the biologically
active oxidized lipids in MM-LDL. We have previously characterized
three oxidized phospholipids present in MM-LDL, atherosclerotic lesions of fat fed rabbits, and autoxidized
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (Ox-PAPC) that
induced human aortic endothelial cells to adhere human monocytes
in vitro. We have used sequential normal and reverse phase-high performance liquid chromatography to isolate various isomers
of an oxidized phospholipid from autoxidized
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine. The
fatty acid in the sn-2 position of this biologically active isomer and its dehydration product was released by phospholipase A2 and characterized. Hydrogenation with platinum(IV)
oxide/hydrogen suggested a cyclic moiety, and reduction with sodium
borohydride suggested two reducible oxygen-containing groups in the
molecule. The fragmentation pattern produced by electrospray
ionization-collision induced dissociation-tandem mass spectrometry was
consistent with a molecule resembling an E-ring prostaglandin with an
epoxide at the 5,6 position. The structure of this lipid was confirmed by proton nuclear magnetic resonance spectroscopy analysis of the free
fatty acid isolated from the dehydration product of
m/z 828.5. Based on these studies, we
arrived at the structure of the biologically active oxidized
phospholipids as 1-palmitoyl-2-(5,6-epoxyisoprostane E2)-sn-glycero-3-phosphocholine. The
identification of this molecule adds epoxyisoprostanes to the growing
list of biologically active isoprostanes.
Department of Medicine, Psychiatry & Biobehavioral Sciences and the Neuropsychiatric Institute, ** Department
of Chemistry and Biochemistry, and
Department of Pathology, University of
California, Los Angeles, California 90095
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W. Pruzanski, E. Stefanski, F. C. de Beer, M. C. de Beer, A. Ravandi, and A. Kuksis Comparative analysis of lipid composition of normal and acute-phase high density lipoproteins J. Lipid Res., July 1, 2000; 41(7): 1035 - 1047. [Abstract] [Full Text]
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