Increased levels of lipid oxidation products in low density lipoproteins of patients suffering from rheumatoid arthritis

Chemistry and Physics of Lipids

Volumn 87, Issue 1, 1997, Pages 81-89

  Jira, Wolfgang ^a   Spiteller, Gerhard ^a   Richter, Andreas ^b  

^a UNIVERSITY OF BAYREUTH   (Germany)

^b INSTITUTE OF PATHOLOGY   (Germany)

Author keywords

hydroxyaldehydes; Aging; Hydroxy fatty acids; LDL; Rheuma

Indexed keywords

CORIOLIC ACID; DIMORPHECOLIC ACID; INTERLEUKIN 1BETA; LEUKOTRIENE; LINOLEIC ACID; LOW DENSITY LIPOPROTEIN;

ADULT; AGED; ARTICLE; CONTROLLED STUDY; FEMALE; HUMAN; LIPID OXIDATION; LIPID PEROXIDATION; LIPOPROTEIN BLOOD LEVEL; MALE; PRIORITY JOURNAL; RHEUMATOID ARTHRITIS;

ADULT; AGED; ALDEHYDES; ARTHRITIS, RHEUMATOID; CHROMATOGRAPHY, GAS; FEMALE; HUMANS; LINOLEIC ACID; LINOLEIC ACIDS; LINOLEIC ACIDS, CONJUGATED; LIPID PEROXIDATION; LIPID PEROXIDES; LIPOPROTEINS, LDL; MALE; MASS SPECTROMETRY; MIDDLE AGED;

EID: 0030742828     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(97)00030-3     Document Type: Article

References (47)

1. Arnett, F.C., Edworthy, S.M., Bloch, D.A., McShane, D.J., Fries, J.F., Cooper, N.S., Healey, L.A., Kaplan, S.R., Liang, M.H., Luthra, H.S., Medsger, T.A., Mitchell, D.M., Neustadt, D.H., Finals, R.S., Schaller, J.G., Sharp, J.T., Wilder, R.L., Hunder, G.G., 1988. The American Rheumatism Association 1987 revised criteria for the classification of rheumatoid arthritis. Arthritis and rheumatism 31, 315-324.
2. Bergström, S., Sjövall, J., 1957. The isolation of prostaglandine. Acta Chem. Scand. 11, 1086.
3. Bergström, S., Ryhage, R., Samuelsson, B., Sjövall, J., 1962. The structure of prostaglandin E, F1 and F2. Acta Chem. Scand. 16, 501-502.
4. Bilodeau, J.F., Wang, M., Chung, F.L., Castonguay, A., 1995. Effects of nonsteroidal antiinflammatory drugs on oxidative pathways in A/J mice. Free Radical Biol. Med. 18(1), 47-54.
5. Blake, D.R., Lunec, J., 1990. In: Cohen, R.D., Alberti, K.G.M.M., Lewis, B., Denman, A.M. (Eds.), The Metabolic and Molecular Basis of Acquired Disease, vol. 20, Bailliere Tindall Limited, London, pp. 189-212.
6. Bligh, B.C., Dyer, W.J., 1959. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37. 911-917.
7. Borgeat, P., Samuelsson, B., 1979. Arachidonic acid metabolism in polytnorphonuclear leukocytes. III. Effects of ionophore A23187. Proc. Natl. Acad. Sci. U.S.A. 76 (5), 2148-2152.
8. Dahle, L.K., Hill, E.G., Holman, R.T., 1962. The thiobarbituric acid reaction and the autoxidation of polyunsaturated fatty acid methyl esters. Arch. Biochem. Biophys. 98, 253-261.
9. Dudda, A., Spiteller, G., Kobelt, F., 1996. Lipid oxidation products in ischemic porcine heart tissue. Chem. Phys. Lipids 82, 39-51.
10. Esterbauer, H., 1982. Aldehydic products of lipid peroxidation Free Radicals. In: McBrien, D.C.H., Slater, T.F. (Eds.) Lipid Peroxidation Cancer, Proceedings of N.F.C.R., 1st Cancer Symposium, 1981, Academic Press. London, pp. 101-128.
11. Esterbauer, H., Cheeseman, K.H., 1990. Determination of aldehydic lipid peroxidation products: malonaldehyde and 4-hydroxynonenal. Methods Enzymol. 186, 407-421.
12. Fairburn, K., Groorveld, M., Ward, R.J., et al., 1993. α-Tocopherol, lipids and lipoproteins in knee-joint synovial fluid and serum from patients with inflammatory joint diseases. Clin. Sci. 83, 657-664.
13. Gallwitz, W.F., Mundy, G.R., Lee, C.H., Qiao, M., Roodman, G.D., Raftery, M., Gaskell, S.J., Bonewald, L.F., 1993. 5-Lipoxygenase metabolites of arachidonic acid Stimulation isolated osteoclasts to resorb calcified matrices. J. Biol. Chem. 268 (14), 10087-10094.
14. Goetzl, E.J., Pickett, W.C., 1980. The human PMN leukocyte chemotactic activity of complex hydroxy-eicosatetraenoic acids (HETEs). J. Immunol. 125, 1789-1791.
15. Goetzl, E.J., Woods, J.M., German, R.R., 1977. Stimulation of human eosinophil and neutrophil polymorphonuclear leukocyte chemotaxis and random migration by 12-L-hydroxy-5,8,10,14-eicosatetraenoic acid. J. Clin. Invest. 59, 179-183.
16. Gowen, M., Mundy, G.R., 1986. Actions of recombinant interleukin 1, interleukin 2, and interferon-γ. on bone resorption in vitro. J. Immunol. 136 (7), 2478-2482.
17. Grosch, W., 1987. Reactions of hydroperoxides. In: Chan, H.W.-S. (Ed.), Products of low molecular weight Autoxid. Unsaturated Lipids, Academic Press London, pp. 95-139.
18. Hamberg, M., Svenson, J., Samuelsson, B., 1975. Thromboxanes. New group of biologically active compounds derived from prostaglandin endoperoxides. Proc. Natl. Acad. Sci. U.S.A. 72 (8), 2994-2998.
19. Heinle, H., Gugeler, N., Felde, R., Spiteller, G., 1996. Oxidation of plasmalogens produce highly effective modulators of macrophage function. Free Rad. Biol., in press.
20. Herold, M., Spiteller, G., 1996. Enzymic production of hydroperoxides of unsaturated fatty acids by injury of mammalian cells. Chem. Phys. Lipids 79 (2). 113-121.
21. Janero, D.R., 1990. Malondialdehyde and thiobarbituric acid-reactivity as diagnostic indexes of lipid peroxidation and peroxidative tissue injury. Free Radical Biol. Med. 9 (6), 515-540.
22. Jira, W., Spiteller, G., Schramm, A., 1996. Increase in hydroxy fatty acids in human low density lipoproteins with age. Chem. Phys. Lipids 84, 165-173.
23. Ku, G., Thomas, C.E., Akeson, A.L., Jackson, R.L., 1992. Induction of interleukin 1β expression from human peripheral blood monocyte-derived macrophages by 9-hydroxyoctadecadienoic acid. J. Biol. Chem. 267 (20), 14183-14188.
24. Lehmann, W.A., Stephan, M., Furstenberger, G., 1992. Profiling assay for lipoxygenase products of linoleic and arachidonic acid by gas chromatography-mass spectrometry. Anal. Biochem. 204 (1), 158-170.
25. Leiss, O., Murawski, U., Egge, H., 1979. The microanalysis of serum lipoprotein lipids. J. Clin. Chem. Clin. Biochem. 17, 619-625.
26. Loidl-Stahlhofen, A., Spiteller, G., 1994. α-Hydroxyaldehydes, products of lipid peroxidation. Biochim. Biophys. Acta 1211 (2), 156-160.
27. Lunec, J., Halloran, S.P., White, A.G., Dormandy, T.L., 1981. Free-radical oxidation (peroxidation) products in serum and synovial fluid in rheumatoid arthritis. Journal of Rheumatology 8 (2), 233-245.
28. McCord, J.M., 1974. Free radicals and inflammation. Protection of synovial fluid by Superoxide dismutase. Science 185 (4150), 529-531.
29. Mlakar, A., Spiteller, G., 1994. Reinvestigation of lipid peroxidation of linolenic acid. Biochim. Biophys. Acta 1214 (2), 209-220.
30. Mlakar, A., Spiteller, G., 1996. Previously unknown aldehydic lipid peroxidation compounds of arachidonic acid. Chem. Phys. Lipids 79 (1). 47-53.
31. Moch, D., Schewe, T., Kuehn, H., Schmidt, D., Buntrock, P., 1990. The linoleic acid metabolite 9Ds-hydroxy10,12(E,Z)-octadecadienoic acid is a strong proinflammatory mediator in an experimental wound healing model of the rat. Biomed. Biochim. Acta 49, 201-207.
32. Moncada, S., Gryglewski, R., Bunting, S., Vane, J.R., 1976. An enzyme isolated from arteries transforms prostaglandin endoperoxides to an unstable substance that inhibits platelet aggregation. Nature (London) 263 (5579). 663-665.
33. Moncada, S., Korbut, R., Bunting, S., Vane, J.R., 1978. Prostacyclin is a circulating hormone. Nature (London) 273 (5665). 767-768.
34. Mueller-Peddinghaus, R., Wurl, M., 1987. The amplified chemiluminescence test to characterize antirheumatic drugs as oxygen radical scavengers. Biochem. Pharmacol. 36 (7), 1125-1132.
35. Murphy, R.C., Hammarstroem, S., Samuelsson, B., 1979. Leukotriene C: A slow-reacting substance from murine mastocytoma cells. Proc. Natl. Acad. Sci. U.S.A. 76 (9), 4275-4279.
36. Muus, P., Bonta, I.L., Den Oudsten, S.A., 1979. Plasma levels of malondialdehyde, a product of cyclo-oxygenase-dependent and independent lipid peroxidation in rheumatoid arthritis: A correlation with disease activity. Prostaglandins Med. 2 (1). 63-65.
37. Nakao, J., Ooyama, T., Ito, H., Chang, W.C., Murota, S., 1982. Comparative effect of lipoxygenase products of arachidonic acid on rat aortic smooth muscle cell migration. Atherosclerosis 44 (3), 339-342.
38. Nikkari, T., Malo-Ranta, U., Hiltunen, T., Jaakkola, O., Ylä-Herttuala, S., 1995. Monitoring of lipoprotein oxidation by gas Chromatographic analysis of hydroxy fatty-acids. J. Lipid Res. 36, 200-207.
39. Oerning, L., Hammarstroem, S., Samuelsson, B., 1980. Leukotriene D: A slow reacting substance for rat basophilic leukemia cells. Proc. Natl. Acad. Sci. U.S.A. 77 (4), 2014-2017.
40. Rubbo, H., Radi, R., Trujillo, M., Telleri, R., Kalyanaraman, B., Barnes, S., Kirk, M., Freeman, B.A., 1994. Nitric oxide regulation of Superoxide and peroxynitrite-dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives. J. Biol. Chem. 269 (42), 26066-26075.
41. Scheick, C., Spiteller, G., 1993. Formation of enol ether epoxides by reaction of (9S,10E, 12Z)-hydroperoxyoctadecadienoic acid with plasmalogens. Liebigs Ann. Chem. 12, 1245-1248.
42. Selley, M.L., Bourne, D.J., Bartlett, M.R., Tymms, K.E., Brook, A.S., Duffield, A.M., Ardlie, N.G., 1992. Occurrence of (E)-4-hydroxy-2-nonenal in plasma and synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Ann. Rheumatic Dis. 51 (4), 481-484.
43. Siakotos, A.N., Bray, R., Dratz, E., van Kuijk, F.J.G.M., Sevanian, A., Koppang, N., 1988. 4-Hydroxynonenal: a specific indicator for canine neuronal-retinal ceroidosis. American Journal of Medical Genetics Supplement. 5. 171-181.
44. Sircar, J.C., Schwender, C.F., Johnson, E.A., 1983. Soybean lipoxygenase inhibition by nonsteroidal antiinflammatory drugs. Prostaglandins 25 (3), 393-396.
45. Tamura, H., Kitta, K., Shibamoto, T., 1991. Formation of reactive aldehydes from fatty acids in a iron(2+)/hydrogen peroxide oxidation system. J. Agric. Food Chem. 39 (3). 439-442.
46. Van Kuijk, F.J.G.M., Thomas, D.W., Stephens, R.J., Dratz, E.A., 1986. Occurrence of 4-hydroxyalkenals in rat tissues determined as pentafluorobenzyl oxime derivatives by gas chromatography-mass spectrometry. Biochem. Biophys. Res. Commun. 139 (1), 144-149.
47. Vick, B.A., Zimmerman, D.C., 1987. Oxidative systems for modification of fatty acids: the lipoxygenase pathway. In: Stumpf, P.K. (Ed.), Biochem. Plants, vol. 9. Academic Press, Orlando FL, pp. 53-90.