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J Biol Chem, Vol. 274, Issue 40, 28395-28404, October 1, 1999
,,
**,, and
From the Departments of Oxidation of human low density lipoprotein (LDL)
generates proinflammatory mediators and underlies early events in
atherogenesis. We identified mediators in oxidized LDL that induced an
inflammatory reaction in vivo, and activated
polymorphonuclear leukocytes and cells ectopically expressing human
platelet-activating factor (PAF) receptors. Oxidation of a synthetic
phosphatidylcholine showed that an sn-1 ether bond confers
an 800-fold increase in potency. This suggests that rare ether-linked
phospholipids in LDL are the likely source of PAF-like activity in
oxidized LDL. Accordingly, treatment of oxidized LDL with phospholipase
A1 greatly reduced phospholipid mass, but did not
decrease its PAF-like activity. Tandem mass spectrometry
identified traces of PAF, and more abundant levels of
1-O-hexadecyl-2-(butanoyl or
butenoyl)-sn-glycero-3-phosphocholines (C4-PAF
analogs) in oxidized LDL that comigrated with PAF-like activity.
Synthesis showed that either C4-PAF was just 10-fold less
potent than PAF as a PAF receptor ligand and agonist. Quantitation by
gas chromatography-mass spectrometry of pentafluorobenzoyl derivatives
shows the C4-PAF analogs were 100-fold more abundant in oxidized LDL than PAF. Oxidation of synthetic alkyl arachidonoyl phosphatidylcholine generated these C4-PAFs in abundance.
These results show that quite minor constituents of the LDL
phosphatidylcholine pool are the exclusive precursors for PAF-like
bioactivity in oxidized LDL.
Pathology and Internal
Medicine and the ** Huntsman Cancer Institute, University of Utah, Salt
Lake City, Utah 84112, the § Department of Pediatrics,
National Jewish Medical and Research Center, Denver, Colorado 80206, and the ¶ Deptamento de Fisiologia & Farmacodinåmica, IOC,
Oswaldo Cruz, Fiocruz, Rio de Janeiro, Brazil 21045-900
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