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Journal of Lipid Research, Vol. 44, 164-171, January 2003
Copyright © 2003 by Lipid Research, Inc.

Ethanolamine plasmalogens prevent the oxidation of cholesterol by reducing the oxidizability of cholesterol in phospholipid bilayers

Ryouta Maeba¹ and Nobuo Ueta

Department of Biochemistry, Teikyo University School of Medicine, Tokyo, Japan

¹ To whom correspondence should be addressed. e-mail: maeba{at}med.teikyo-u.ac.jp

The aims of the present study are to establish an appropriate system for assessing the oxidizability of cholesterol (CH) in phospholipid (PL) bilayers, and to explore the effect of ethanolamine plasmalogens on the oxidizability of CH with the system, through comparing with those of choline plasmalogens, phosphatidylethanolamine, and antioxidant -tocopherol (Toc). Investigation of the effects of oxidants, vesicle lamellar forms, saturation level, and constituent ratio of PLs in vesicles on CH oxidation revealed the suitability of a system comprising unilamellar vesicles and the water-soluble radical initiator 2,2'-azobis (2-amidino-propane) dihydrochloride (AAPH). As CH oxidation in the system was found to follow the rate law for autoxidation without significant interference from oxidizable PLs, the oxidizability of CH in PL bilayers could be experimentally determined from the equation: k _p/(2k _t)^1/2=R _p/[LH]R_i^1/2 by measuring the rate of CH oxidation. It was found with this system that bovine brain ethanolamine plasmalogen (BBEP), bovine heart choline plasmalogen, and egg yolk phosphatidylethanolamine lower the oxidizability of CH in bilayers. Comparison of the dose-dependent effects of each PL demonstrated the greatest ability of BBEP to reduce the oxidizability.

A time course study of CH oxidation suggested a novel mechanism of BBEP for lowering the oxidizability of CH besides the action of scavenging radicals.

Abbreviations: AAPH, 2,2'-azobis (2-amidino-propane) dihydrochloride; BBEP, bovine brain ethanolamine plasmalogen (1-O-alk-1 enyl-2-acyl-sn-glycero-3-phosphoethanolamine); BHCP, bovine heart choline plasmalogen (1-O-alk-1 eny-2-acyl-sn-glycero-3-phosphocholine); CH, cholesterol; EYPE, egg yolk phosphatidylethanolamine; LUV, large unilammelar vesicle; PL, phospholipid; Toc, -tocopherol

Supplementary key words free radicals • unilamellar vesicles • radical initiator • antioxident • phosphatidylethanolamine

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