Identification of a radical formed in the reaction mixtures of oxidized phosphatidylcholine with ferrous ions using HPLC–ESR and HPLC–ESR–MS

References

• Halliwell B, Grootveld M. The measurement of free radical reactions in humans. Some thoughts for future experimen-tation. FEBS Lett 1987;213:9–14.
   Google Scholar
• Halliwell B, Gutteridge JMC. Oxygen free radicals and iron in relation to biology and medicine: Some problems and concepts. Arch Biochem Biophys 1986;246:501–514.
   PubMed Web of Science ®Google Scholar
• Gutteridge JMC, Halliwell B. The measurement and mechanism of lipid peroxidation in biological systems. Trends Biochem Sci 1990;15:129–135.
   PubMed Web of Science ®Google Scholar
• Yamamoto Y. Chemiluminescence-based high performance liquid chromatography assay of lipid hydroperoxides. Methods Enzymol 1994;233:319–324.
   PubMed Web of Science ®Google Scholar
• Miyazawa T, Fujimoto K, Suzuki T, Yasuda K. Determination of phospholipid hydroperoxides using luminol chemilumines-cence-high-performance liquid chromatography. Methods Enzymol 1994;233:324–332.
   PubMed Web of Science ®Google Scholar
• McIntyre TM, Zimmerman GA, Prescott SM. Biologically active oxidized phospholipids. J Biol Chem 1999;274: 25189–25192.
   PubMed Web of Science ®Google Scholar
• Watson AD, Leitinger N, Navab M, Faull KF, Horkko S, Witztum JL, Palinski W, Schwenke D, Salomon RG, Sha W, Subbanagounder G, Fogelman AM, Berliner JA. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence of their presence in vivo. J Biol Chem 1997;272:13597–13607.
   Google Scholar
• Morrow JD, Awad JA, Boss HJ, Blair IA, Roberts II, U. Non-cyclooxygenase-derived prostanoids (F2-isoprostanes) are formed in situ on phospholipids. Proc Natl Acad Sci USA 1992;89:10721–10725.
   PubMed Web of Science ®Google Scholar
• Hall LM, Murphy RC. Analysis of stable oxidized molecular species of glycerophospholipids following treatment of red blood cell ghosts with t-butylhydroperoxide. Anal Biochem 1998;258:184–194.
   PubMed Web of Science ®Google Scholar
• Makino K, Imaishi H, Morinishi S, Takeuchi T, Fujita Y. An ESR study on lipid peroxidation process. Formation of hydrogen atoms and hydroxyl radicals. Biochem Biophys Res Commun 1986;141:381–386.
   Google Scholar
• Yoshida T, Otake H, Aramaki Y, Hara T, Tsuchiya S, Hamada A, Utsumi H. Free radicals from 1-palmitoy1-2-arachidonoyl-phosphatidylcholine liposomes in Fe2+/ascorbic acid solution. Biol Pharm Bull 1996;19: 779–782.
   Google Scholar
• Iwamura M, Inamoto N. Novel formation of nitroxide radicals by radical addition to nitrones. Bull Chem Soc Jpn 1967;40:703.
   Web of Science ®Google Scholar
• Janzen EG, Blackburn BJ. Detection and identification of short-lived free radicals by an electron spin resonance trapping technique. J Am Chem Soc 1968;90:5909–5910.
   Web of Science ®Google Scholar
• Rokushika S, Taniguchi H, Hatano H. Flow ESR detector for liquid chromatography of radicals. Anal Lett 1975;8:205–213.
   Google Scholar
• Makin° K, Hatano H. Separation and characterization of short-lived radicals in DL-methionine aqueous solution by high speed liquid chromatograph equipped with ESR spectrometer. Chem Lett 1979;:119–122.
   Google Scholar
• Iwahashi H, Negoro Y, Ikeda A, Morishita H, Kido R. Inhibition by chlorogenic acid of haematin-catalysed retinoic acid 5,6-epoxidation. Biochem J 1986;239: 641–646.
   Google Scholar
• Iwahashi H, Parker EC, Mason RP, Tomer KB. Combined liquid chromatography/electron paramagnetic resonance spec-trometry/electrospray ionization mass spectrometry for radical identification. Anal Chem 1992;64:2244–2252.
   PubMed Web of Science ®Google Scholar
• Iwahashi H, Albro PW, McGown SR, Tomer KB, Mason RP. Isolation and identification of ck-(4-pyridy1-1-oxide)-N-tert-butylnitrone radical adducts formed by the decomposition of the hydroperoxides of linoleic acid, linolenic acid, and arachidonic acid by soybean lipoxygenase. Arch Biochem Biophys 1991;285: 172–180.
   Google Scholar
• Iwahashi H, Parker CE, Mason RP, Tomer KB. Radical adducts of nitrosobenzene and 2-methyl-2-nitrosopropane with 12,13-epoxylinoleic acid radical, 12,13-epoxylinolenic acid radical and 14, 15-epoxyarachidonic acid radical. Biochem J 1991;276:447–453.
   PubMed Web of Science ®Google Scholar
• Iwahashi H, Deterding ij, Parker CE, Mason RP, Tomer KB. Identification of radical adducts formed in the reactions of unsaturated fatty acids with soybean lipoxygenase using continuous flow fast atom bombardment with tandem mass spectrometry. Free Radic Res 1996;25:255–274.
   Google Scholar
• Iwahashi H. Some polyphenols inhibit the formation of pentyl radical and octanoic acid radical in the reaction mixture of linoleic acid hydroperoxide with ferrous ions. Biochem J 2000;346:265–273.
   PubMed Web of Science ®Google Scholar
• Iwahashi H, Nishizaki K, Takagi I. Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide. Biochem J 2002;361:57–66.
   Google Scholar
• Qian SY, Tomer KB, Yue G, Guo Q, Kadiiska MB, Mason RP. Characterizarion of the initial carbon-centered pentadienyl radical and subsequent radicals in lipid peroxidation: Identification via on-line high performance liquid chromato-graphy/electron spin resonance and mass spectrometery. Free Radic Biol Med 2002;33:998–1009.
   PubMedGoogle Scholar
• Reis A, Domingues MR, Amado FM, Ferrer-Correia AJ, Domingues P. Detection and characterization by mass spectrometry of radical adducts produced by linoleic acid oxidation. J Am Soc Mass Spectrom 2003;14: 1250–1261.
   Google Scholar
• Iwahashi H. Identification of the several new radicals formed in the reaction mixture of oxidized linoleic acid with ferrous ions using HPLC-ESR and HPLC-ESR-MS. Free Radic Res 2003;37:939–945.
   PubMed Web of Science ®Google Scholar
• Iwahashi H, Kumamoto K, Hirai T. The formation of the 7-carboxyheptyl radical from 13-hydroperoxy-9,11-octadecadienoic acid catalyzed by hemoglobin and myoglobin under anaerobic conditions. J Biochem 2003;133: 679— 685.
   Google Scholar
• Crawford CG, Plattner RD, Sessa DJ, Rackis H. Separation of oxidized and unoxidized molecular species of phosphatidyl-choline by high pressure liquid chromatography. Lipids 1980;15:91–94.
   Web of Science ®Google Scholar
• Lindstrom TD, Aust SD. Studies on cytochrome P-450-dependent lipid hydroperoxide reduction. Arch Biochem Biophys 1984;233:80–87.
   PubMed Web of Science ®Google Scholar
• Eskola J, Laakso S. Bile salt-dependent oxygen-ation of polyunsaturated phosphatidylcholines by soy-bean lipoxygenase-1. Biochim Biophys Acta 1983;751: 305 —311.
   Google Scholar
• Chamulitrat W, Mason RP. Alkyl free radicals from the [3-scission of fatty acid alkoxyl radicals as detetcted by spin trapping in a lipoxygenase system. Arch Biochem Biophys 1990;282:65–69.
   PubMedGoogle Scholar