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Issue title: The Proceedings of the 3rd International Conference on Food Factors (ICoFF 03)
Article type: Research Article
Authors: Tsuji, Kentaro | Kawai, Yoshichika | Kato, Yoji | Osawa, Toshihiko
Affiliations: Laboratory of Food and Biodynamics, Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan | School of Humanities for Environmental Policy and Technology, Himeji Institute of Technology, Himeji 670-0092, Japan
Note: [] Corresponding author. Tel.: +81 52 789 4126; Fax: +81 52 789 5741; E-mail: osawat@agr.nagoya-u.ac.jp
Abstract: The primary amino groups of biomolecules such as aminophospholipids, as well as proteins, are the potential targets of covalent modifications by lipid peroxidation products; however, little attention has been paid to the modification of aminophospholipids such as phosphatidylethanolamine (PE). The purpose of this study is to characterize the formation of a novel modified phospholipid, N-(hexanoyl)phosphatidylethanolamine (HEPE), in the reaction of PE with lipid hydroperoxides using mass spectrometric analyses. Upon reaction of egg PE with 13-hydroperoxyoctadecadienoic acid or other oxidized polyunsaturated fatty acids followed by phospholipase D-mediated hydrolysis, the formation of N-(hexanoyl)ethanolamine (HEEA), a head group of HEPE, was confirmed by isotope dilution liquid chromatography/tandem mass spectrometry. Moreover, increasing HEEA was detected in the hydrolysates of oxidized erythrocyte ghosts and low-density lipoprotein with their increasing lipid peroxidation levels. Collectively, these results suggest that the N-hexanoylated product of phospholipid, HEPE, can be generated during lipid peroxidation and may serve as one mechanism for the covalent modification of aminophospholipids in vivo.
Keywords: lipid peroxidation, aminophospholipid, amide-type adduct, oxidative modification, LC/MS/MS
Journal: BioFactors, vol. 21, no. 1-4, pp. 263-266, 2004
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