title: Oxygenation of arachidonoyl lysophospholipids by lipoxygenases from soybean, porcine leukocyte, or rabbit reticulocyte.
abstract: Oxygenation of arachidonoyl lysophosphatidylcholine (lysoPC) or arachidonoyl lysophosphatidic acid (lysoPA) by lipoxygenase (LOX) was examined. The oxidized products were identified by HPLC/UV spectrophotometry/mass spectrometry analyses. Straight-phase and chiral-phase HPLC analyses indicated that soybean LOX-1 and rabbit reticulocyte LOX oxygenated arachidonoyl lysophospholipids mainly at C-15 with the S form as major enantiomer, whereas porcine leukocyte LOX oxygenated at C-12 with the S form. Next, the sequential exposure of arachidonoyl-lysoPC to soybean LOX-1 and porcine leukocyte LOX afforded two major isomers of dihydroxy derivatives with conjugated triene structure, suggesting that 15(S)-hydroperoxyeicosatetraenoyl derivatives were converted to 8,15(S)-dihydroxyeicosatetraenoyl derivatives. Separately, arachidonoyl-lysoPA, but not arachidonoyl-lysoPC, was found to be susceptible to double oxygenation by soybean LOX-1 to generate a dihydroperoxyeicosatetraenoyl derivative. Overall, arachidonoyl lysophospholipids were more efficient than arachidonic acid as LOX substrate. Moreover, the catalytic efficiency of arachidonoyl-lysoPC as substrate of three lipoxygenases was much greater than that of arachidonoyl-lysoPA or arachidonic acid. Taken together, it is proposed that arachidonoyl-lysoPC or arachidonoyl-lysoPA is efficiently oxygenated by plant or animal lipoxygenases, C12- or C15-specific, to generate oxidized products with conjugated diene or triene structure.
authors.affiliation: College of Pharmacy and Department of Food and Nutrition, Chungnam National University, Taejon, Korea.
authors.forename: Long Shuang
authors.initials: LS
authors.lastname: Huang
authors.forename: Jong Seong
authors.initials: JS
authors.lastname: Kang
authors.forename: Mee Ree
authors.initials: MR
authors.lastname: Kim
authors.forename: Dai-Eun
authors.initials: DE
authors.lastname: Sok
mesh_terms: D000818:Animals; D001091:Arachidonate Lipoxygenases / Q000378:metabolism; D016718:Arachidonic Acid / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D007962:Leukocytes / Q000201:enzymology*; D008084:Lipoxygenase / Q000378:metabolism*; D008244:Lysophosphatidylcholines / Q000378:metabolism*; D013058:Mass Spectrometry / Q000379:methods; D010084:Oxidation-Reduction; D011817:Rabbits; D012156:Reticulocytes / Q000201:enzymology*; D013025:Glycine max / Q000201:enzymology*; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013552:Swine
chemical_list: D008244:Lysophosphatidylcholines; D016718:Arachidonic Acid; D001091:Arachidonate Lipoxygenases; D008084:Lipoxygenase