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Journal of Lipid Research, Vol 37, 2361-2371, Copyright © 1996 by Lipid Research, Inc.
RP Patel, U Diczfalusy, S Dzeletovic, MT Wilson and VM Darley-Usmar
Oxidation of low density lipoprotein (LDL) in the artery wall leads to the
formation of cholesterol oxidation products that may result in
cytotoxicity. Different mechanisms could contribute to LDL oxidation in
vivo resulting in characteristic and specific modification of the
cholesterol molecule. Alternatively, attack on cholesterol by chain
propagating peroxyl radicals could result in the same distribution of
oxidation products irrespective of the initial pro-oxidant mechanism. To
distinguish between these possibilities we have monitored the formation of
nine oxysterols during LDL oxidation, promoted by copper, myoglobin,
peroxynitrite, or azo bis amidino propane. Regardless of the oxidant used,
the pattern of oxysterol formation was essentially the same. The yields of
products identified decreased in the order 7- oxocholesterol > 7
beta-hydroxycholesterol > 7 alpha-hydroxycholesterol > 5,6
beta-epoxycholesterol > 5,6 alpha-epoxycholesterol except in the case of
peroxynitrite in which case a higher yield of 5, 6 beta- epoxycholesterol
relative to 7-oxocholesterol was found. No formation of cholestane 3 beta,
5 alpha, 6 beta-triol, or the 24-,25-,27- hydroxycholesterols was seen.
Concentration of 7-oxocholesterol levels in LDL was positively correlated
with the degree of protein modification. Endogenous alpha-tocopherol in LDL
or supplementation with butylated hydroxytoluene prevented oxysterol
formation. Taken together these data indicate that the oxidation of
cholesterol and protein in LDL occur as secondary oxidation events
consequent on the attack of fatty acid peroxyl/alkoxyl radicals on the
7-position of cholesterol, and with amino acids on apoB. Furthermore,
oxidant processes with atherogenic potential, such as peroxynitrite,
copper, and myoglobin are capable of producing oxidized LDL containing
cytotoxic mediators.
ARTICLES
Formation of oxysterols during oxidation of low density lipoprotein by peroxynitrite, myoglobin, and copper
Department of Biological and Chemical Sciences, University of Essex, Colchester, United Kingdom.
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