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Journal of Lipid Research, Vol 36, 1876-1886, Copyright © 1995 by Lipid Research, Inc.
H Kamido, A Kuksis, L Marai and JJ Myher
We have isolated the core aldehydes (aldehydes still bound to parent
molecules) of phosphatidylcholine (PC) and cholesteryl esters (CE) from
copper-catalyzed peroxidation of human plasma low (LDL) and high (HDL)
density lipoproteins. The aldehydes were isolated by extraction with
acidified chloroform-methanol containing 2,4-dinitrophenylhydrazine. The
2,4-dinitrophenylhydrazone (DNPH) derivatives formed were resolved by
reversed phase high performance liquid chromatography (HPLC) and identified
by on-line quadrupole mass spectrometry (LC/MS). The major PC core
aldehydes from oxidized LDL and HDL were identified as 1-
palmitoyl-(1-stearoyl) 2-(9-oxononanoyl)-, 1-palmitoyl-(1-stearoyl) 2-
(8-oxooctanoyl)-, and 1-palmitoyl-(1-stearoyl) 2-(5-oxovaleroyl)-sn-
glycerols after phospholipase C digestion of the DNPH derivatives of the
phospholipids. The major aldehydes from peroxidation of cholesteryl esters
were the 9-oxononanoyl, 8-oxooctanoyl, and 5-oxovaleroyl esters of
cholesterol and 7-ketocholesterol. The core aldehydes were estimated to
account for a minimum of 1-2% of the consumed linoleate and arachidonate
esters. A relatively smaller yield of the PC core aldehydes from LDL
compared to HDL was attributed to the presence of greater amounts of
phospholipases in LDL than in HDL. More comparable yields of PC core
aldehydes were obtained in the presence of phenylmethylsulfonylfluoride,
which inhibits phospholipases. We conclude that peroxidation of LDL and HDL
results in formation of detectable amounts of cholesteryl and
glycerophospholipid esters containing aldehyde functions. The yield of PC
aldehydes varies with the activity of the platelet activating factor (PAF)
acetyl hydrolase.
ARTICLES
Lipid ester-bound aldehydes among copper-catalyzed peroxidation products of human plasma lipoproteins
Banting and Best Department of Medical Research, University of Toronto, Canada.
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