HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Citation Map Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Tokumura, A. Articles by Yamamoto, S. Search for Related Content PubMed PubMed Citation Articles by Tokumura, A. Articles by Yamamoto, S. Social Bookmarking                      What's this?

Journal of Lipid Research, Vol. 41, 953-962, June 2000
Copyright © 2000 by Lipid Research, Inc.

Original Article

Structural identification of phosphatidylcholines having an oxidatively shortened linoleate residue generated through its oxygenation with soybean or rabbit reticulocyte lipoxygenase

Correspondence to: Akira Tokumura

Phosphatidylcholines (PCs) with platelet-activating factor (PAF)-like biological activities are known to be generated by fragmentation of the sn-2-esterified polyunsaturated fatty acyl group. The reaction is free radical-mediated and triggered by oxidants such as metal ions, oxyhemoglobin, and organic hydroperoxides. In this study, we characterized the PAF-like phospholipids produced on reaction of PC having a linoleate group with lipoxygenase enzymes at low oxygen concentrations. When the oxidized PCs were analyzed by gas chromatography;–mass spectrometry, two types of oxidatively fragmented PC were detected. One PC had an sn-2-short chain saturated or unsaturated acyl group (C₈;–C₁₃) with an aldehydic terminal; the abundant species were PCs with C₉ and C₁₃. The other PC had a short chain saturated acyl group (C₆;–C₉) with a methyl terminal, and the most predominant species was PC with C₈. When the extracts of oxidation products were subjected to catalytic hydrogenation, PCs having saturated acyl groups (C₆;–C₁₄) were detected; the most abundant was C₁₂ species. The less regiospecific formation of PAF-like lipids suggests that they were generated by oxidative fragmentation of PC hydroperoxides formed by non-stereoselective oxygenation of the alkyl radical of esterified linoleate that escaped from the active centers of lipoxygenases. One of the PAF-like PC with an aldehydic terminal was found to be bioactive; it inhibited the production of nitric oxide induced by lipopolysaccharide and interferon- in vascular smooth muscle cells from rat aorta.—Tokumura, A., T. Sumida, M. Toujima, K. Kogure, K. Fukuzawa, Y. Takahashi, and S. Yamamoto. Structural identification of phosphatidylcholines having an oxidatively shortened linoleate residue generated through its oxygenation with soybean or rabbit reticulocyte lipoxygenase. J. Lipid Res. 2000. 41: 953;–962.

Supplementary key words: platelet-activating factor, phosphatidylcholine hydroperoxide, free radical, lipid peroxidation, gas chromatography;–mass spectrometry, nitric oxide production

CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				C. M. Buseman, P. Tamura, A. A. Sparks, E. J. Baughman, S. Maatta, J. Zhao, M. R. Roth, S. W. Esch, J. Shah, T. D. Williams, et al. Wounding Stimulates the Accumulation of Glycerolipids Containing Oxophytodienoic Acid and Dinor-Oxophytodienoic Acid in Arabidopsis Leaves Plant Physiology, September 1, 2006; 142(1): 28 - 39. [Abstract] [Full Text] [PDF]

				N. Androulakis, H. Durand, E. Ninio, and D. C. Tsoukatos Molecular and mechanistic characterization of platelet-activating factor-like bioactivity produced upon LDL oxidation J. Lipid Res., September 1, 2005; 46(9): 1923 - 1932. [Abstract] [Full Text] [PDF]

				G. K. Marathe, G. A. Zimmerman, and T. M. McIntyre Platelet-activating Factor Acetylhydrolase, and Not Paraoxonase-1, Is the Oxidized Phospholipid Hydrolase of High Density Lipoprotein Particles J. Biol. Chem., January 31, 2003; 278(6): 3937 - 3947. [Abstract] [Full Text] [PDF]

				D. Heydeck, J. M. Upston, H. Viita, S. Yla-Herttuala, and R. Stocker Oxidation of LDL by rabbit and human 15-lipoxygenase: prevalence of nonenzymatic reactions J. Lipid Res., July 1, 2001; 42(7): 1082 - 1088. [Abstract] [Full Text] [PDF]

				H. Lum and K. A. Roebuck Oxidant stress and endothelial cell dysfunction Am J Physiol Cell Physiol, April 1, 2001; 280(4): C719 - C741. [Abstract] [Full Text] [PDF]