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Volumn 44, Issue 9, 2003, Pages 1660-1666

Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins

Author keywords

Cholesteryl linoleate; Lipoproteins; Mass spectrometry; Nitration

Indexed keywords

CHOLESTEROL DERIVATIVE; CHOLESTERYL NITROLINOLEATE; NITRIC OXIDE; NITRITE; UNCLASSIFIED DRUG;

EID: 0141794273     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.M200467-JLR200     Document Type: Article
Times cited : (65)

References (39)
  • 1
    • 0032464635 scopus 로고    scopus 로고
    • Pathophysiology of nitric oxide and related species: Free radical reactions and modification of biomolecules
    • Eiserich, J. P., R. P. Patel, and V. B. O'Donnell. 1998. Pathophysiology of nitric oxide and related species: free radical reactions and modification of biomolecules. Molec. Aspects Med. 19: 221-357.
    • (1998) Molec. Aspects Med. , vol.19 , pp. 221-357
    • Eiserich, J.P.1    Patel, R.P.2    O'Donnell, V.B.3
  • 2
    • 0032171420 scopus 로고    scopus 로고
    • Chemical biology of nitric oxide: Insights into regulatory, cytotoxic, and cytoprotective mechanisms of nitric oxide
    • Wink, D. A., and J. B. Mitchell. 1998. Chemical biology of nitric oxide: insights into regulatory, cytotoxic, and cytoprotective mechanisms of nitric oxide. Free Radic. Biol. Med. 25: 434-456.
    • (1998) Free Radic. Biol. Med. , vol.25 , pp. 434-456
    • Wink, D.A.1    Mitchell, J.B.2
  • 3
    • 0019817746 scopus 로고
    • Mechanisms of nitrogen dioxide reactions: Initiation of lipid peroxidation and the production of nitrous acid
    • Pryor, W. A., and J. W. Lightsey. 1981. Mechanisms of nitrogen dioxide reactions: initiation of lipid peroxidation and the production of nitrous acid. Science. 214: 435-437.
    • (1981) Science , vol.214 , pp. 435-437
    • Pryor, W.A.1    Lightsey, J.W.2
  • 4
    • 0020246537 scopus 로고
    • Reaction of nitrogen dioxide with alkene and polyunsaturated fatty acids: Addition and hydrogen abstraction mechanism
    • Pryor, W. A., J. W. Lightsey, and D. F. Church. 1982. Reaction of nitrogen dioxide with alkene and polyunsaturated fatty acids: addition and hydrogen abstraction mechanism. J. Am. Chem. Soc. 104: 6685-6692.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 6685-6692
    • Pryor, W.A.1    Lightsey, J.W.2    Church, D.F.3
  • 5
    • 0000874476 scopus 로고
    • Rates and mechanisms of reaction of nitrogen dioxide with alkenes in solution
    • Giamalva, D. H., G. B. Kenion, D. F. Church, and W. A. Pryor. 1987. Rates and mechanisms of reaction of nitrogen dioxide with alkenes in solution. J. Am. Chem. Soc. 109: 7059-7063.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7059-7063
    • Giamalva, D.H.1    Kenion, G.B.2    Church, D.F.3    Pryor, W.A.4
  • 6
    • 0029836494 scopus 로고    scopus 로고
    • Nitric oxide regulation of lipid peroxidation reactions: Formation and analysis of nitrogen-containing oxidized lipid derivatives
    • Rubbo, H., and B. A. Freeman. 1996. Nitric oxide regulation of lipid peroxidation reactions: formation and analysis of nitrogen-containing oxidized lipid derivatives. Methods Enzymol. 269: 385-394.
    • (1996) Methods Enzymol. , vol.269 , pp. 385-394
    • Rubbo, H.1    Freeman, B.A.2
  • 7
    • 0028793450 scopus 로고
    • Nitric oxide inhibition of lipoxygenase-dependent liposome and low-density lipoprotein oxidation: Termination of radical chain propagation reactions and formation of nitrogen-containing oxidized lipid derivatives
    • Rubbo, H., S. Parthasarathy, S. Barnes, M. K. B. Kalyanaraman, and B. A. Freeman. 1995. Nitric oxide inhibition of lipoxygenase-dependent liposome and low-density lipoprotein oxidation: termination of radical chain propagation reactions and formation of nitrogen-containing oxidized lipid derivatives. Arch. Biochem. Biophys. 324: 15-25.
    • (1995) Arch. Biochem. Biophys. , vol.324 , pp. 15-25
    • Rubbo, H.1    Parthasarathy, S.2    Barnes, S.3    Kalyanaraman, M.K.B.4    Freeman, B.A.5
  • 8
    • 0029118058 scopus 로고
    • Action of nitric oxide as an antioxidant against oxidation of soybean phosphatidyl choline liposomal membranes
    • Hayashi, K., N. Noguchi, and E. Niki. 1995. Action of nitric oxide as an antioxidant against oxidation of soybean phosphatidyl choline liposomal membranes. FEBS Lett. 370: 37-40.
    • (1995) FEBS Lett. , vol.370 , pp. 37-40
    • Hayashi, K.1    Noguchi, N.2    Niki, E.3
  • 9
    • 0026787909 scopus 로고
    • A protective role for nitric oxide in the oxidative modification of low-density lipoproteins by mouse macrophages
    • Yates, M. T., L. E. Lambert, J. P. Whiuen, L. McDonald, M. Mano, G. Ku, and S. J. T. Mao. 1992. A protective role for nitric oxide in the oxidative modification of low-density lipoproteins by mouse macrophages. FEBS Lett. 309: 135-138.
    • (1992) FEBS Lett. , vol.309 , pp. 135-138
    • Yates, M.T.1    Lambert, L.E.2    Whiuen, J.P.3    McDonald, L.4    Mano, M.5    Ku, G.6    Mao, S.J.T.7
  • 10
    • 0000577249 scopus 로고    scopus 로고
    • Kinetics of the reaction between ethyl peroxy radicals and nitric oxide
    • Maricq, M. J., and J. J. Szente. 1996. Kinetics of the reaction between ethyl peroxy radicals and nitric oxide. J. Phys. Chem. 96: 986-992.
    • (1996) J. Phys. Chem. , vol.96 , pp. 986-992
    • Maricq, M.J.1    Szente, J.J.2
  • 11
    • 0027228294 scopus 로고
    • The reaction of nitric oxide with peroxyl radicals
    • Padmaja, S., and R. E. Huie. 1993. The reaction of nitric oxide with peroxyl radicals. Biochem. Biophys. Res. Commun. 15: 539-544.
    • (1993) Biochem. Biophys. Res. Commun. , vol.15 , pp. 539-544
    • Padmaja, S.1    Huie, R.E.2
  • 12
    • 0027408024 scopus 로고
    • The identification of the allylic nitrite and nitro derivatives of the methyl linoleate and methyl linolenate by negative chemical ionization mass spectrometry
    • Galon, A. A., and W. A. Pryor. 1993. The identification of the allylic nitrite and nitro derivatives of the methyl linoleate and methyl linolenate by negative chemical ionization mass spectrometry. Lipids. 28: 125-133.
    • (1993) Lipids , vol.28 , pp. 125-133
    • Galon, A.A.1    Pryor, W.A.2
  • 13
    • 0028205948 scopus 로고
    • The reaction of low levels of nitrogen dioxide with methyl linoleate in the presence and absence of oxygen
    • Galon, A. A., and W. A. Pryor. 1994. The reaction of low levels of nitrogen dioxide with methyl linoleate in the presence and absence of oxygen. Lipids. 29: 171-176.
    • (1994) Lipids , vol.29 , pp. 171-176
    • Galon, A.A.1    Pryor, W.A.2
  • 16
    • 0032914526 scopus 로고    scopus 로고
    • Nitration of unsatured fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide and nitronium ion
    • O'Donnell, V. B., J. P. Eiserich, P. H. Chumley, M. J. Jablonsky, M. Kirk, S. Barnes, V. M. Darley-Usmar, and B. A. Freeman. 1999. Nitration of unsatured fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide and nitronium ion. Chem. Res. Toxicol. 12: 83-92.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 83-92
    • O'Donnell, V.B.1    Eiserich, J.P.2    Chumley, P.H.3    Jablonsky, M.J.4    Kirk, M.5    Barnes, S.6    Darley-Usmar, V.M.7    Freeman, B.A.8
  • 17
    • 0034637496 scopus 로고    scopus 로고
    • Acid-promoted reactions of ethyl linoleate with nitrite ions: Formation and structural characterization of isomeric nitroalkene, nitrohydroxy and novel 3-nitro-1,5-hexadiene and 1,5-dinitro-1, 3-pentadiene products
    • Napolitano, A., E. Camera, M. Picardo, and M. D'Ischia. 2000. Acid-promoted reactions of ethyl linoleate with nitrite ions: formation and structural characterization of isomeric nitroalkene, nitrohydroxy and novel 3-nitro-1,5-hexadiene and 1,5-dinitro-1, 3-pentadiene products. J. Org. Chem. 65: 4853-4860.
    • (2000) J. Org. Chem. , vol.65 , pp. 4853-4860
    • Napolitano, A.1    Camera, E.2    Picardo, M.3    D'Ischia, M.4
  • 18
    • 0037154813 scopus 로고    scopus 로고
    • Reaction of hydro (pero)xy derivatives of polyunsaturated fatty acids/esters with nitrite ions under acidic conditions. Unusual nitrosative breakdown of methyl 13-hydro(pero)xyoactadeca-9,1-dienoate to a novel 4-nitro-2-oximinoalk-3-enal product
    • Napolitano, A., E. Camera, M. Picardo, and M. D'Ischia. 2002. Reaction of hydro (pero)xy derivatives of polyunsaturated fatty acids/ esters with nitrite ions under acidic conditions. Unusual nitrosative breakdown of methyl 13-hydro(pero)xyoactadeca-9,1-dienoate to a novel 4-nitro-2-oximinoalk-3-enal product. J. Org. Chem. 67: 1125-1132.
    • (2002) J. Org. Chem. , vol.67 , pp. 1125-1132
    • Napolitano, A.1    Camera, E.2    Picardo, M.3    D'Ischia, M.4
  • 19
    • 0034758161 scopus 로고    scopus 로고
    • Vicinal nitrohydroeicosatrienoic acids: Vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid
    • Balazy, M., T. Iesaki, J. L. Park, H. Jiang, P. M. Kaminski, and M. Wolin. 2001. Vicinal nitrohydroeicosatrienoic acids: vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid. J. Pharmacol. Exper. Ther. 299: 1-9.
    • (2001) J. Pharmacol. Exper. Ther. , vol.299 , pp. 1-9
    • Balazy, M.1    Iesaki, T.2    Park, J.L.3    Jiang, H.4    Kaminski, P.M.5    Wolin, M.6
  • 20
    • 0037183523 scopus 로고    scopus 로고
    • Characterization of linoleic acid nitration in human blood plasma by mass spectrometry
    • Lima, E. S., P. Di Mascio, H. Rubbo, and D. S. P. Abdalla. 2002. Characterization of linoleic acid nitration in human blood plasma by mass spectrometry. Biochemistry. 41: 10717-10722.
    • (2002) Biochemistry , vol.41 , pp. 10717-10722
    • Lima, E.S.1    Di Mascio, P.2    Rubbo, H.3    Abdalla, D.S.P.4
  • 22
    • 18544380386 scopus 로고    scopus 로고
    • Nitrolinoleate inhibits platelet activation by attenuating calcium mobilization and inducing phosphorylation of vasodilator-stimulated phosphoprotein (VASP) through elevation of cAMP
    • Coles, B., A. Bloodsworth, J. P. Eiserich, M. J. Coffey, R. M. McLoughlin, J. C. Giddings, M. J. Lewis, R. J. Haslam, B. A. Freeman, and V. B. O'Donnell. 2002. Nitrolinoleate inhibits platelet activation by attenuating calcium mobilization and inducing phosphorylation of vasodilator-stimulated phosphoprotein (VASP) through elevation of cAMP. J. Biol. Chem. 277: 5832-5840.
    • (2002) J. Biol. Chem. , vol.277 , pp. 5832-5840
    • Coles, B.1    Bloodsworth, A.2    Eiserich, J.P.3    Coffey, M.J.4    McLoughlin, R.M.5    Giddings, J.C.6    Lewis, M.J.7    Haslam, R.J.8    Freeman, B.A.9    O'Donnell, V.B.10
  • 23
    • 0037032025 scopus 로고    scopus 로고
    • Nitrolinoleate inhibits superoxide generation, degranulation, and integrin expression by human neutrophils
    • Coles, B., A. Bloodsworth, S. R. Clark, M. J. Lewis, A. R. Cross, B. A. Freeman, and V. B. O'Donnell. 2002. Nitrolinoleate inhibits superoxide generation, degranulation, and integrin expression by human neutrophils. Circ. Res. 91: 375-381.
    • (2002) Circ. Res. , vol.91 , pp. 375-381
    • Coles, B.1    Bloodsworth, A.2    Clark, S.R.3    Lewis, M.J.4    Cross, A.R.5    Freeman, B.A.6    O'Donnell, V.B.7
  • 24
    • 0018222219 scopus 로고
    • Recognition of functional groups by chemical ionization mass spectrometry
    • Lin, Y. Y., and L. L. Smith. 1978. Recognition of functional groups by chemical ionization mass spectrometry. Biomed. Mass Spectrom. 11: 604-611.
    • (1978) Biomed. Mass Spectrom. , vol.11 , pp. 604-611
    • Lin, Y.Y.1    Smith, L.L.2
  • 25
    • 0033927959 scopus 로고    scopus 로고
    • Oxidation of LDL by mieloperoxidase and reactive nitrogen species: Reaction pathways and antioxidant protection
    • Carr, A. C., M. R. McCall, and B. Frei. 2000. Oxidation of LDL by mieloperoxidase and reactive nitrogen species: reaction pathways and antioxidant protection. Arterioscler. Thromb. Vasc. Biol. 20: 1716-1723.
    • (2000) Arterioscler. Thromb. Vasc. Biol. , vol.20 , pp. 1716-1723
    • Carr, A.C.1    McCall, M.R.2    Frei, B.3
  • 26
    • 0034705975 scopus 로고    scopus 로고
    • Coordination (Ag+) ion spray-mass spectrometry of peroxidation products of cholesterol linoleate and cholesterol arachidonate: High-performance liquid chromatography-mass spectrometry analysis of peroxide products from polyunsaturated lipid autoxidation
    • Havrilla, C. M., D. L. Hachey, and N. A. Porter. 2000. Coordination (Ag+) ion spray-mass spectrometry of peroxidation products of cholesterol linoleate and cholesterol arachidonate: high-performance liquid chromatography-mass spectrometry analysis of peroxide products from polyunsaturated lipid autoxidation. J. Am. Chem. Soc. 122: 8042-8055.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8042-8055
    • Havrilla, C.M.1    Hachey, D.L.2    Porter, N.A.3
  • 28
    • 0032801499 scopus 로고    scopus 로고
    • Preparation of fatty acid cholesteryl ester hydroperoxides by photosensitized oxidation
    • Hafidi, M. E., F. Michel, J. Bascoul, and A. C. Paulet. 1999. Preparation of fatty acid cholesteryl ester hydroperoxides by photosensitized oxidation. Chem. Phys. Lipid. 100: 127-138.
    • (1999) Chem. Phys. Lipid , vol.100 , pp. 127-138
    • Hafidi, M.E.1    Michel, F.2    Bascoul, J.3    Paulet, A.C.4
  • 29
    • 0342757728 scopus 로고    scopus 로고
    • Strong increase in hydroxy fatty acids derived from linoleic acid in human low density lipoproteins of atherosclerotic patiens
    • Jira, W., G. Spiteller, W. Carson, and A. Schram. 1998. Strong increase in hydroxy fatty acids derived from linoleic acid in human low density lipoproteins of atherosclerotic patiens. Chem. Phys. Lipids. 91: 1-11.
    • (1998) Chem. Phys. Lipids , vol.91 , pp. 1-11
    • Jira, W.1    Spiteller, G.2    Carson, W.3    Schram, A.4
  • 31
    • 0032701646 scopus 로고    scopus 로고
    • Myeloperoxidase-generated reactive nitrogen species convert LDL into an atherogenic form in vitro
    • Podrez, E. A., D. Schmitt, H. F. Hoff, and S. L. Hazen. 1999. Myeloperoxidase-generated reactive nitrogen species convert LDL into an atherogenic form in vitro. J. Clin. Invest. 103: 1547-1560.
    • (1999) J. Clin. Invest. , vol.103 , pp. 1547-1560
    • Podrez, E.A.1    Schmitt, D.2    Hoff, H.F.3    Hazen, S.L.4
  • 32
    • 0029885126 scopus 로고    scopus 로고
    • Endothelial dysfunction in atherosclerosis
    • Busse, R., and I. Fleming. 1996. Endothelial dysfunction in atherosclerosis. J. Vasc. Res. 33: 181-194.
    • (1996) J. Vasc. Res. , vol.33 , pp. 181-194
    • Busse, R.1    Fleming, I.2
  • 33
    • 0035254176 scopus 로고    scopus 로고
    • Is ceruloplasmin an important catalyst for S-nitrosothiol generation in hypercholesterolemia?
    • Moriel, P., I. R. Pereira, M. C. Bertolami, and D. S. P. Abdalla. 2001. Is ceruloplasmin an important catalyst for S-nitrosothiol generation in hypercholesterolemia? Free Radic. Biol. Med. 30: 318-326.
    • (2001) Free Radic. Biol. Med. , vol.30 , pp. 318-326
    • Moriel, P.1    Pereira, I.R.2    Bertolami, M.C.3    Abdalla, D.S.P.4
  • 34
    • 0034682928 scopus 로고    scopus 로고
    • Mechanisms of the pro- and anti-oxidant actions of nitric oxide in atherosclerosis
    • Palel, R. P., A. L. Levonen, J. H. Crawford, and V. M. Darley-Usmar. 2000. Mechanisms of the pro- and anti-oxidant actions of nitric oxide in atherosclerosis. Cardiovasc. Res. 47: 465-474.
    • (2000) Cardiovasc. Res. , vol.47 , pp. 465-474
    • Palel, R.P.1    Levonen, A.L.2    Crawford, J.H.3    Darley-Usmar, V.M.4
  • 35
    • 0025677318 scopus 로고
    • Diet-induced atherosclerosis increases the release of nitrogen oxides from rabbit aorta
    • Minor, R. L., P. R. Myers, R. Guerra, J. N. Bates, and D. G. Harrison. 1990. Diet-induced atherosclerosis increases the release of nitrogen oxides from rabbit aorta. J. Clin. Invest. 86: 2109-2116.
    • (1990) J. Clin. Invest. , vol.86 , pp. 2109-2116
    • Minor, R.L.1    Myers, P.R.2    Guerra, R.3    Bates, J.N.4    Harrison, D.G.5
  • 36
    • 0030729868 scopus 로고    scopus 로고
    • Mechanisms of oxidative damage of low density lipoprotein in human atherosclerosis
    • Heineck, J. W. 1997. Mechanisms of oxidative damage of low density lipoprotein in human atherosclerosis. Curr. Opin. Lipidol. 8: 268-274.
    • (1997) Curr. Opin. Lipidol. , vol.8 , pp. 268-274
    • Heineck, J.W.1
  • 37
    • 0034659148 scopus 로고    scopus 로고
    • The oxidative modification hypothesis of atherogenesis: An overview
    • Chisolm, G. M., and D. Steinberg. 2000. The oxidative modification hypothesis of atherogenesis: an overview. Free Radic. Biol. Med. 28: 1815-1826.
    • (2000) Free Radic. Biol. Med. , vol.28 , pp. 1815-1826
    • Chisolm, G.M.1    Steinberg, D.2
  • 38
    • 0032705538 scopus 로고    scopus 로고
    • Oxidized lipoproteins in blood plasma: Possible marker of atherosclerosis progression
    • Moriel, P., F. S. Okawabata, and D. S. P. Abdalla. 1999. Oxidized lipoproteins in blood plasma: possible marker of atherosclerosis progression. IUBMB Life. 48: 413-417.
    • (1999) IUBMB Life , vol.48 , pp. 413-417
    • Moriel, P.1    Okawabata, F.S.2    Abdalla, D.S.P.3
  • 39
    • 0034682916 scopus 로고    scopus 로고
    • Lipid peroxidation, antioxidants and cardiovascular disease: How should we more forward?
    • Halliwell, B. 2000. Lipid peroxidation, antioxidants and cardiovascular disease: how should we more forward? Cardiovasc. Res. 47: 410-418.
    • (2000) Cardiovasc. Res. , vol.47 , pp. 410-418
    • Halliwell, B.1


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