Bioactive phospholipid oxidation products

Free Radical Biology and Medicine

Volumn 28, Issue 12, 2000, Pages 1762-1770

  Marathe, Gopal K ^a   Harrison, Kathleen A ^d   Murphy, Robert C ^d   Prescott, Stephen M ^a,c   Zimmerman, Guy A ^a,b   McIntyre, Thomas M ^a,b  

^a UNIVERSITY OF UTAH SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF UTAH   (United States)

^c UNIVERSITY OF UTAH   (United States)

^d NATIONAL JEWISH MEDICAL AND RESEARCH CENTER   (United States)

Author keywords

Free radicals; Inflammation; Low density lipoprotein; Peroxide; Phospholipid; Platelet activating factor

Indexed keywords

ASCORBIC ACID; ETHER; GUANINE NUCLEOTIDE BINDING PROTEIN; HYDROXYL RADICAL; PHOSPHATIDYLCHOLINE; PHOSPHOLIPASE A1; PHOSPHOLIPID; REACTIVE OXYGEN METABOLITE; THROMBOCYTE ACTIVATING FACTOR RECEPTOR;

HUMAN; INFLAMMATION; MASS SPECTROMETRY; NONHUMAN; OXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL; REVIEW;

EID: 0034659133     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00234-3     Document Type: Article

References (52)

1. Small D.M. George Lyman Duff memorial lecture. Progression and regression of atherosclerotic lesions. Insights from lipid physical biochemistry. Arteriosclerosis. 8:1988;103-129.
2. Morand O.H. Reactivity of plasmalogens to singlet oxygen and radicals. Methods Enzymol. 234:1994;603-620.
3. Morand O.H., Zoeller R.A., Raetz C.R. Disappearance of plasmalogens from membranes of animal cells subjected to photosensitized oxidation. J. Biol. Chem. 263:1988;11597-11606.
4. Khaselev N., Murphy R.C. Susceptibility of plasmenyl glycerophosphoethanolamine lipids containing arachidonate to oxidative degradation. Free Radic. Biol. Med. 26:1999;275-284.
5. Wagner B.A., Buettner G.R., Burns C.P. Free radical-mediated lipid peroxidation in cells oxidizability is a function of cell lipid bis-allylic hydrogen content . Biochemistry. 33:1994;4449-4453.
6. Coffey M.D., Cole R.A., Colles S.M., Chisolm G.M. In vitro cell injury by oxidized low density lipoprotein involves lipid hydroperoxide-induced formation of alkoxyl, lipid, and peroxyl radicals. J. Clin. Invest. 96:1995;1866-1873.
7. Morrow J.D., Roberts L.J. II. The isoprostanes. Current knowledge and directions for future research. Biochem. Pharmacol. 51:1996;1-9.
8. Kayganich-Harrison K.A., Rose D.M., Murphy R.C., Morrow J.D., Roberts L.J.D. Collision-induced dissociation of F2-isoprostane-containing phospholipids. J. Lipid Res. 34:1993;1229-1235.
9. Harrison K.A., Murphy R.C. Isoleukotrienes are biologically active free radical products of lipid peroxidation. J. Biol. Chem. 270:1995;17273-17278.
10. Kerwin J.L., Tuininga A.R., Ericsson L.H. Identification of molecular species of glycerophospholipids and sphingomyelin using electrospray mass spectrometry. J. Lipid Res. 35:1994;1102-1114.
11. Harrison K.A., Murphy R.C. Negative electrospray ionization of glycerophosphocholine lipids formation of [M-15]-ions occurs via collisional decomposition of adduct anions . J. Mass Spectrum. 30:1995;1772-1773.
12. MacMillan D.K., Murphy R.C. Analysis of lipid hydroperoxides and long-chain conjugated keto acids by negative ion electrospray mass spectrometry. J. Am. Soc. Mass Spectrum. 6:1995;1190-1201.
13. Harrison K.A., Murphy R.C. Direct mass spectrometric analysis of ozonides application to unsaturated glycerophosphocholine lipids . Anal. Chem. 68:1996;3224-3230.
14. Watson A.D., Leitinger N., Navab M., Faull K.F., Horkko S., Witztum J.L., Palinski W., Schwenke D., Salomon R.G., Sha W., Subbanagounder G., Fogelman A.M., Berliner J.A. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/endothelial interactions and evidence for their presence in vivo. J. Biol. Chem. 272:1997;13597-135607.
15. Marathe G.K., Davies S.S., Harrison K.A., Silva A.R., Murphy R.C., Castro-Faria-Neto H., Prescott S.M., Zimmerman G.A., McIntyre T.M. Inflammatory platelet-activating factor-like phospholipids in oxidized low density lipoproteins are fragmented alkyl phosphatidylcholines. J. Biol. Chem. 274:1999;28395-28404.
16. Mallat Z., Nakamura T., Ohan J., Leseche G., Tedgui A., Maclouf J., Murphy R.C. The relationship of hydroxyeicosatetraenoic acids and F2-isoprostanes to plaque instability in human carotid atherosclerosis. J. Clin. Invest. 103:1999;421-427.
17. Shimizu T., Honda Z., Nakamura M., Bito H., Izumi T. Platelet-activating factor receptor and signal transduction. Biochem. Pharmacol. 44:1992;1001-1008.
18. Prescott S.M., McIntyre T.M., Zimmerman G.A. Platelet-activating factor a phospholipid mediator of inflammation . Gallin J.I., Snyderman R. Inflammation basic principles and clinical correlates . 1999;387-396 Lippincott Williams & Wilkins, Philadelphia.
19. O'Flaherty J.T., Salzer W.L., Cousart S., McCall C.E., Piantadosi C., Surles J.R., Hammett M.J., Wykle R.L. Platelet-activating factor and analogues comparative studies with human neutrophils and rabbit platelets . Res. Commun. Chem. Pathol. Pharmacol. 39:1983;291-309.
20. Shen, T. Y.; Hwang, S.-B.; Doebber, T. W.; Robbins, J. C. The chemical and biological properties of PAF agonists, antagonists, and biosynthetic inhibitors. In: Synder, F., ed. Platelet-activating factor and related lipid mediators. New York: Plenum Press; 1987:153-190.
21. O'Flaherty J.T., Tessner T., Greene D., Redman J.R., Wykle R.L. Comparison of 1-O-alkyl-, 1-O-alk-1′-enyl-, and 1-O-acyl-2-acetyl-sn-glycero-3-phosphoethanolamines and -3-phosphocholines as agonists of the platelet-activating factor family. Biochim. Biophys. Acta. 1210:1994;209-216.
22. Goetzl E.J., An S. Diversity of cellular receptors and functions for the lysophospholipid growth factors lysophosphatidic acid and sphingosine 1-phosphate. FASEB J. 12:1998;1589-1598.
23. Chun J., Contos J.J., Munroe D. A growing family of receptor genes for lysophosphatidic acid (LPA) and other lysophospholipids (LPs). Cell Biochem. Biophys. 30:1999;213-242.
24. Tokumura A., Kamiyasu K., Takauchi K., Tsukatani H. Evidence for existence of various homologues and analogues of platelet activating factor in a lipid extract of bovine brain. Biochem. Biophys. Res. Commun. 145:1987;415-425.
25. Patel K.D., Zimmerman G.A., Prescott S.M., McIntyre T.M. Novel leukocyte agonists are released by endothelial cells exposed to peroxide. J. Biol. Chem. 267:1992;15168-15175.
26. Heery J.M., Kozak M., Stafforini D.M., Jones D.A., Zimmerman G.A., McIntyre T.M., Prescott S.M. Oxidatively modified LDL contains phospholipids with PAF-like activity and stimulates the growth of smooth muscle cells. J. Clin. Invest. 96:1995;2322-2330.
27. Smiley P.L., Stremler K.E., Prescott S.M., Zimmerman G.A., McInytre T.M. Oxidatively fragmented phosphatidylcholines activate human neutrophils through the receptor for platelet-activating factor. J. Biol. Chem. 266:1991;11104-11110.
28. Schlame M., Haupt R., Wiswedel I., Kox W.J., Rustow B. Identification of short-chain oxidized phosphatidylcholine in human plasma. J. Lipid Res. 37:1996;2608-2615.
29. Lehr H.A., Weyrich A.S., Saetzler R.K., Jurek A., Arfors K.E., Zimmerman G.A., Prescott S.M., McIntyre T.M. Vitamin C blocks inflammatory PAF mimetics created by cigarette smoking. J. Clin. Invest. 99:1997;2358-2364.
30. Diagne A., Fauvel J., Record M., Chap H., Douste-Blazy L. Studies on ether phospholipids comparative composition of various tissues from human, rat and guinea pig . Biochim. Biophys. Acta. 793:1984;221-231.
31. Tsoukatos D.C., Arborati M., Liapikos T., Clay K.L., Murphy R.C., Chapman M.J., Ninio E. Copper-catalyzed oxidation mediates PAF formation in human LDL subspecies. Protective role of PAF acetylhydrolase in dense LDL . Arterioscler. Thromb. Vasc. Biol. 17:1997;3505-3512.
32. Lehr H.A., Seemuller J., Hubner C., Menger M.D., Messmer K. Oxidized LDL-induced leukocyte/endothelium interaction in vivo involves the receptor for platelet-activating factor. Arterioscler. Thromb. 13:1993;1013-1018.
33. Berliner J.A., Heinecke J.W. The role of oxidized lipoproteins in atherogenesis. Free. Radic. Biol. Med. 20:1996;707-727.
34. Stremler K.E., Stafforini D.M., Prescott S.M., Zimmerman G.A., McIntyre T.M. An oxidized derivative of phosphatidylcholine is a substrate for the platelet-activating factor acetylhydrolase from human plasma. J. Biol. Chem. 264:1989;5331-5334.
35. Stremler K.E., Stafforini D.M., Prescott S.M., McIntyre T.M. Human plasma platelet-activating factor acetylhydrolase Oxidatively-fragmented phospholipids as substrates . J. Biol. Chem. 266:1991;11095-11103.
36. Clay K.L. Quantitation of platelet-activating factor by gas chromatography-mass spectrometry. Methods Enzymol. 187:1990;134-142.
37. Whatley R.E., Clay K.L., Chilton F.H., Triggiani M., Zimmerman G.A., McIntyre T.M., Prescott S.M. Relative amounts of 1-0-alkyl- and 1-acyl-2-acetyl-sn-glycero-3-phosphocholine in stimulated endothelial cells. Prostaglandins. 43:1992;21-29.
38. Clay K.L., Johnson C., Worthen G.S. Biosynthesis of platelet activating factor and 1-0-acyl analogues by endothelial cells. Biochim. Biophys. Acta. 1094:1991;43-50.
39. Mueller H.W., O'Flaherty J.T., Wykle R.L. The molecular species distribution of platelet-activating factor synthesized by rabbit and human neutrophils. J. Biol. Chem. 259:1984;14554-14559.
40. Blank M.L., Cress E.A., Lee T.-C., Malone B., Surles J.R., Piantadosi C., Hajdu J., Snyder F. Structural features of platelet-activating factor (1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) required for hypotensive and platelet serotonin responses. Res. Commun. Chem. Pathol. Pharmacol. 38:1982;3-20.
41. Tanaka T., Iimori M., Tsukatani H., Tokumura A. Platelet-aggregating effects of platelet-activating factor-like phospholipids formed by oxidation of phosphatidylcholines with an sn-2-polyunsaturated fatty acyl group. Biochim. Biophys. Acta. 1210:1994;202-208.
42. Kern H., Volk T., Knaure-Sciefer S., Mieth T., Rustow B., Kox W.J., Schlame M. Stimulation of monocytes and platelets by short-chain phosphatidylcholines with and without terminal carboxy groups. Biochim. Biophys. Acta. 1394:1998;33-42.
43. Leitinger N., Watson A.D., Faull K.F., Fogelman A.M., Berliner J.A. Monocyte binding to endothelial cells induced by oxidized phospholipids present in minimally oxidized low density lipoprotein is inhibited by a platelet activating factor receptor antagonist. Adv. Exp. Med. Biol. 433:1997;379-382.
44. Kimura H., Wu N.Z., Dodge R., Spencer D.P., Klitzman B.M., McIntyre T.M., Dewhirst M.W. Inhibition of radiation-induced up-regulation of leukocyte adhesion to endothelial cells with the platelet-activating factor inhibitor, BN52021. Int. J. Radiat. Oncol. Biol. Phys. 33:1995;627-633.
45. Church D.F., Pryor W.A. Free-radical chemistry of cigarette smoke and its toxicological implications. Environ. Health Perspect. 64:1985;111-126.
46. Lehr H.A., Frei B., Arfors K.E. Vitamin C prevents cigarette smoke-induced leukocyte aggregation and adhesion to endothelium in vivo. Proc. Natl. Acad. Sci. USA. 91:1994;7688-7692.
47. Lehr H.A., Kress E., Menger M.D., Friedl H.P., Hubner C., Arfors K.E., Messmer K. Cigarette smoke elicits leukocyte adhesion to endothelium in hamsters inhibition by CuZn-SOD . Free Radic. Biol. Med. 14:1993;573-581.
48. Lehr H.-A. Adhesion-promoting effects of cigarette smoke on leukocytes and endothelial cells. Ann. NY Acad. Sci. 686:1993;112-119.
49. Imaizumi T., Satoh K., Yoshida H., Kawamura H., Hiramoto M., Takamatsu S. Effect of cigarette smoking on the levels of platelet-activating factor-like lipid(s) in plasma lipoproteins. Atherosclerosis. 87:1991;47-55.
50. Riemersma R.A., Wood D.A., Macintyre C.C.A., Elton R.A., Gey K.F., Oliver M.F. Risk of angina pectoris and plasma concentrations of vitamins A, C, and E and carotene. Lancet. 337:1991;1-5.
51. Enstrom J.E., Kanim L.E., Klein M.A. Vitamin C intake and mortality among a sample of the United States population. Epidemiology. 3:1992;194-202.
52. Weber C., Erl W., Weber K., Weber P.C. Increased adhesiveness of isolated monocytes to endothelium is prevented by vitamin C intake in smokers. Circulation. 93:1996;1488-1492.