Enzymic lipid peroxidation - A consequence of cell injury?

Free Radical Biology and Medicine

Volumn 21, Issue 7, 1996, Pages 1003-1009

  Spiteller, Gerhard ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Activation of dormant enzymes; Cell injury; Generation of second messengers; Lipid peroxidation; Production of LO* radicals

Indexed keywords

ESTERASE; HYDROPEROXIDE; PLASMALOGEN;

AGING; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; ATHEROSCLEROSIS; CELL DAMAGE; CELL PROLIFERATION; ENZYME MECHANISM; HEART INFARCTION; LIPID MEMBRANE; LIPID PEROXIDATION; NONHUMAN; PATHOPHYSIOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; SECOND MESSENGER; SWINE;

ANIMALIA; SIGANUS; SUS SCROFA;

EID: 0029969018     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(96)00268-7     Document Type: Article

References (85)

1. 1. Girotti, A. W. Mechanisms of lipid peroxidation. Free Radic. Biol. Med. 1(2):87-95; 1985.
2. 2. Halliwell, B.; Grootveld, M. The measurement of free radical reactions in humans. Some thoughts for future experimentation. FEBS Lett. 213(1):9-14; 1987.
3. 3. Yagi, K. Lipid peroxides and human diseases. Chem. Phys. Lipids 45:337-351; 1987.
4. 4. Braughler, J. M.; Hall, E. D. Central nervous system trauma and stroke. I. Biochemical considerations for oxygen radical formation and lipid peroxidation. Free Radic. Biol. Med. 6(3):289-301; 1989.
5. 5. Gardner, H. W. Oxygen radical chemistry of polyunsaturated fatty acids. Free Radic. Biol. Med. 7(1):65-86; 1989.
6. 6. Esterbauer, H.; Gebicki, J.; Puhl, H.; Juergens, G. The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radic. Biol. Med. 13(4):341-390; 1992.
7. 7. Pryor, W. A. The free-radical theory of aging revisited: A critique and a suggested disease-specific theory. In: Warner, H. R. ed. Modern biological theories of aging. New York: Raven Press; 1987:89-112.
8. 8. Beetens, J. R.; Herman, A. G. Ascorbic acid and prostaglandin formation. Int. J. Vitam. Nutr. Res. Suppl. 24:131-144; 1983.
9. 9. Wells, I. C.; Peitzmeier, G.; Vincent, J. K. Lecithin: Cholesterol acyltransferase and lysolecithin in coronary atherosclerosis. Exp. Mol. Pathol. 45(3):303-310; 1986.
10. 10. Gurr, M. I.; James, A. T. eds. In: Lipid biochemistry. London: Chapman & Hall; 1971.
11. 11. Bergström, S.; Sjövall, J. The isolation of prostaglandine. Acta Chem. Scand. 11:1086; 1957.
12. 12. Bergström, S.; Ryhage, R.; Samuelsson, B.; Sjövall, J. The structure of prostaglandin E, F1 and F2. Acta Chem. Scand. 16:501-502; 1962.
13. 13. Hamberg, M.; Svensson, J.; Samuelsson, B. Thromboxanes. New group of biologically active compounds derived from prostaglandin endoperoxides. Proc. Natl. Acad. Sci. USA 72(8):2994-2998; 1975.
14. 14. Moncada, S.; Korbut, R.; Bunting, S.; Vane, J. R. Prostacyclin is a circulating hormone. Nature 273(5665):767-768; 1978.
15. 15. Croft, K. P. C.; Voisey, C. R.; Slusarenko, A. J. Mechanism of hypersensitive cell collapse: Correlation of increased lipoxygenase activity with membrane damage in leaves of Phaseolus vulgaris (L.) inoculated with an avirulent race of Pseudomonas syringae pv. phaseolicola. Physiol. Mol. Plant Pathol. 36(1):49-62; 1990.
16. 16. Shewfelt, R. L.; Erickson, M. C. Role of lipid peroxidation in the mechanism of membrane-associated disorders in edible plant tissue. Trends Food Sci. Technol. 2(6):152-154; 1991.
17. 17. Halliwell, B. The role of oxygen radicals in human disease, with particular reference to the vascular system. Haemostasis 23(Suppl. 1):18-26; 1993.
18. 18. Hamberg, M.; Samuelsson, B. On the specifity of the lipoxidase catalyzed oxygenation of unsaturated fatty acids. Biochem. Biophys. Res. Commun. 21:531-536; 1965.
19. 19. Egmond, M. R.; Vliegenthart, J. F. G.; Boldingh, J. Stereospecificity of the hydrogen abstraction at carbon atom n-8 in the oxygenation of linoleic acid by lipoxygenases from corn germs and soybeans. Biochem. Biophys. Res. Commun. 48(5):1055-1060; 1972.
20. 20. Yla-Herttuala, S. Macrophages and oxidized low density lipoproteins in the pathogenesis of atherosclerosis. Ann. Med. (Helsinki) 23(5):561-567; 1991.
21. 21. Pech, M. A.; Myara, I.; Vedie, B.; Moatti, N. Modified LDL and atherosclerosis. Nature of modifications. Physicochemical and biological properties. Ann. Biol. Clin. 50(4):213-127; 1992.
22. 22. Steinbrecher, U. P.; Zhang, H.; Lougheed, M. Role of oxidatively modified LDL in atherosclerosis. Free Radic. Biol. Med. 9(2):155-168; 1990.
23. 23. Weisser, B.; Locher, R.; Mengden, T.; Sachinidis, A.; Vetter, W. Oxidized low-density lipoproteins in atherogenesis: possible mechanisms of action. J. Cardiovasc. Pharmacol. 19(Suppl. 2):S4-S7; 1992.
24. 24. Steinberg, D.; Parthasarathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320(14):915-924; 1989.
25. 25. Witztum, J. L.; Steinberg, D. Role of oxidized low density lipoprotein in atherogenesis. J. Clin. Invest. 88(6):1785-1792; 1991.
26. 26. Sparrow, C. P.; Parthasarathy, S.; Steinberg, D. Enzymic modification of low density lipoprotein by purified lipoxygenase plus phospholipase A2 mimics cell-mediated oxidative modification. J. Lipid Res. 29(6):745-753; 1988.
27. 27. Bjoerkerud, S. Atherosclerosis initiated by mechanical trauma in normolipidemic rabbits. Atherosclerosis 9:209-213; 1969.
28. 28. Ross, R. Atherosclerosis: A problem of the biology of the arterial wall cells and their interactions with blood components. Arteriosclerosis (Dallas) 1(5):293-311; 1981.
29. 29. Galliard, T. Aspects of lipid metabolism in higher plants. III. Enzymic breakdown of lipids in potato tuber by phospholipid-and galactolipid-acyl hydrolase activities and by lipoxygenase. Phytochemistry 9(8):1725-1734; 1970.
30. 30. Galliard, T. Lipolytic and lipoxygenase enzymes in plants and their action in wounded tissues. In: Kahl, G. ed. Biochem. Wounded plant tissues. Berlin: deGruyter; 1978:155-201.
31. 31. Spiteller, G. On the chemistry of oxidative stress. J. Lipid Mediators. 7(3):199-221; 1993.
32. 32. Hölzel, C.; Spiteller, G. Zellschädigung als Ursache für die Bildung von Hydroperoxiden ungesättigter Fettsäuren. Naturwissenschaften 82:452-460; 1995.
33. 33. Holman, R. T.; Burr, G. O. Spectrophotometric studies of the oxidation of fats. IV. Ultraviolet absorption spectra of lipoxidase-oxidized fats. Arch. Biochem. 7:47; 1945.
34. 34. Bergström, S. On the oxidation of linoleic acid with lipoxidase. Ark. Kem. Mineral. Geol. 21A(15); 1946.
35. 35. Ben-Aziz, A.; Grossmann, S.; Ascarelli, I.; Budowski, P. Linoleate oxidation induced by lipoxygenase and heme proteins: A direct spectrophotometric assay. Anal. Biochem. 34(1):88-100; 1970.
36. 36. Slater, T. F. ed. Free radical mechanisms in tissue injury (Pion Advanced Biochemistry Series, No. 1). London: Pion; 1972.
37. 37. Herold, M.; Spiteller, G. Massive production of hydroperoxides of unsaturated fatty acids by injury of mammalian cells. Chem. Phys. Lipids 79:113-121; 1996.
38. 38. Halliwell, B.; Gutteridge, J. M. C.; Cross, C. E. Free radicals, antioxidants, and human disease: where are we now? J. Lab. Clin. Med. 119(6):598-620; 1992.
39. 39. Bercz, J. P. Toxicology of drinking water disinfection byproducts from nutrients. Rate studies of destruction of polyunsaturated fatty acids in vitro by chlorine-based disinfectants. Chem. Res. Toxicol. 5(3 ):418-425; 1992.
40. 40. Winterbourn, C. C.; Van den Berg, J. J. M.; Roitman, E.; Kuypers, F. A. Chlorohydrin formation from unsaturated fatty acids reacted with hypochlorous acid. Arch. Biochem. Biophys. 296(2):547-555; 1992.
41. 41. Hazell, L. J.; van den Berg, J. J. M.; Stocker, R. Oxidation of low-density lipoprotein by hypochlorite causes aggregation that is mediated by modification of lysine residues rather than lipid oxidation. Biochem. J. 302(1):297-304; 1994.
42. 42. Heinecke, J. W.; Li, W.; Mueller, D. M.; Bohrer, A. Cholesterol chlorohydrin synthesis by the myeloperoxidase-hydrogen peroxide-chloride system: Potential markers for lipoproteins oxidatively damaged by phagocytes. Biochemistry 33(33):10127-10136; 1994.
43. 43. Yamagata, S.; Murakami, H.; Terano, J.; Matsushita, S. Nonenzymic oxidation products of methyl arachidonate. Agric. Biol. Chem. 47(12):2791-2799; 1983.
44. 44. Mlakar, A.; Spiteller, G. Distinction between enzymic and nonenzymic lipid peroxidation. J. Chrom. (in press).
45. 45. Lehmann, W. D.; Metzger, K.; Stephan, M.; Wittig, U.; Zalan, A. J. R.; Habenicht, A. J. R. Quantitative lipoxygenase product profiling by gas chromatography negative-ion chemical ionization mass spectrometry. Anal. Biochem. 224(1):227-234; 1995.
46. 46. Thomas, C. E.; Reed, D. J. Current status of calcium in hepatocellular injury. Hepatology 10(3):375-384; 1989.
47. 47. Orrenius, S.; McConkey, D. J.; Bellomo, G. Role of calcium in toxic cell killing. Trends Pharmacol. Sci. 10(7):281-285; 1989.
48. 48. Aust, S. D. Sources of iron for lipid peroxidation in biological systems. In: Halliwell, B., ed., Oxygen radicals tissue injury, Proc. Brook Lodge Symp., Meeting Date 1987, Bethesda, Md, Fed Am. Soc. Exp. Biol. 1989:27-33.
49. 49. Kanner, J. Mechanism of nonenzymic lipid peroxidation in muscle foods. ACS Symp. Ser., 500 (Lipid Oxid. Food):55-73; 1992.
50. 50. Esterbauer, H. Aldehydic products of lipid peroxidation. In: McBrien, D. C. H.; Slater, T. F., eds. Free radicals, lipid peroxidation cancer, Proc. N.F.C.R. Cancer Symp., 1st, Meeting Date 1981, London, U.K.: Academic; 1982:101-128.
51. 51. Loidl-Stahlhofen, A.; Hannemann, K.; Spiteller, G. Generation of α-hydroxy-aldehydic compounds in the course of lipid peroxidation. Biochim. Biophys. Acta 1213:140-148; 1994.
52. 52. Mlakar, A.; Spiteller, G. Reinvestigation of lipid peroxidation of linolenic acid. Biochim. Biophys. Acta 1214:209-220; 1994.
53. 53. Mlakar, A.; Batna, A.; Spiteller, G. Iron (II) ions induced oxidation of ascorbic acid and sugars. Free Radic. Res. (in press).
54. 54. Dudda, A.; Spiteller, G. Lipid oxidation products in ischemic porcine heart tissue. Chem. Phys. Lipids (in press).
55. 55. Schewe, T.; Kuehn, H.; Wiesner, R.; Belkner, J.; Moch, D. Mammalian lipoxygenases - Are they only involved in the arachidonic acid cascade? Agents Actions 32(1-2):77-78; 1991.
56. 27 steroids by soybean lipoxygenase and rat liver microsomes. Lipids 15(8):563-571; 1980.
57. 57. Imai, H.; Werthessen, N. T.; Subramanyam, V.; LeQuesne, P. W.; Soloway, A. H.; Kanisawa, M. Angiotoxicity of oxygenated sterols and possible precursors. Science 207(4431):651-653; 1980.
58. 58. Sevanian, A.; Berliner, J.; Peterson, H. Uptake, metabolism, and cytotoxicity of isomeric cholesterol-5,6-epoxides in rabbit aortic endothelial cells. J. Lipid Res. 32(1):147-155; 1991.
59. 59. Parthasarathy, S.; Wieland, E.; Steinberg, D. A role for endothelial cell lipoxygenase in the oxidative modification of low density lipoprotein. Proc. Natl. Acad. Sci. USA 86(3):1046-1050; 1989.
60. 60. Rankin, S. M.; Parthasarathy, S.; Steinberg, D. Evidence for a dominant role of lipoxygenase(s) in the oxidation of LDL by mouse peritoneal macrophages. J. Lipid Res. 32(3):449-456; 1991.
61. 61. Benz, D. J.; Mol, M.; Ezaki, M.; Mori-Ito, N.; Zelan, I.; Miyanohara, A.; Friedmann, T.; Parthasarathy, S.; Steinberg, D. I.; Witztum, J. L. Enhanced levels of lipoperoxides in low density lipoprotein incubated with murine fibroblasts expressing high levels of human 15-lipoxygenase. J. Biol. Chem. 270(10):5191-5197; 1995.
62. 62. Meyer, W.; Spiteller, G. Epoxidation of carbon-carbon double bonds in terpenes by linoleic acid hydroperoxides. Liebigs Ann. Chem. 1253-1256; 1993.
63. 63. Ozawa, T., Sugiyama, S., Hayakawa, M. Leukocytes biosynthesize leukotoxin (9,10-epoxy-12-octadecenoate) - A novel cytotoxic linoleate epoxide. Adv. Prostaglandin, Thromboxane, Leukotriene Res. 19(Taipei Conf. Prostaglandin Leukotrine Res., 1988): 164-176; 1989.
64. 64. Ozawa, T.; Sugiyama, S.; Hayakawa, M.; Taki, F. Neutrophil microsomes biosynthesize linoleate epoxide (9,10-epoxy-12-octadecenotae), a biological active substance. Biochem. Biophys. Res. Commun. 152:1310-1318; 1988.
65. 65. Fukushima, A.; Hayakawa, M.; Sugiyama, S.; Ajioka, M.; Ito, T.; Satake, T.; Ozawa, T. Cardiovascular effects of leukotoxin (9,10-epoxy-12-octadecenoate) and free fatty acids in dogs. Cardiovasc. Res. 22(3):213-18; 1988.
66. 66. Fitzpatrick, F. A.; Murphy, R. C. Cytochrome P-450 metabolism of arachidonic acid: Formation and biological actions of "epoxygenase"-derived eicosanoids. Pharmacol. Rev. 40(4):229-241; 1988.
67. 67. Capdevila, J. H.; Karara, A.; Waxman, D. J.; Martin, M. V.; Falck, J. R. Cytochrome P-450 enzyme-specific control of the regio-and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. J. Biol. Chem. 265(19):10865-108671; 1990.
68. 68. Loidl-Stahlhofen, A.; Hannemann, K.; Felde, R.; Spiteller, G. Epoxidation of plasmalogens: Source of long-chain α-hydroxyaldehydes in subcellular fractions of bovine liver. Biochem. J. 309:807-812; 1995.
69. 69. Finley, J. W.; Lundin, R. E. Lipid hydroperoxide induced oxidation of cysteine in peptides. Autoxid. Food Biol. Syst. [Proc. Int. Workshop] 223-235. Ed.: Simic, Michael G.; Karel, Marcus. Plenum: New York, NY
70. 70. Vaca, C. E.; Wilhelm, J.; Harms-Ringdahl, M. Interaction of lipid peroxidation products with DNA. A review. Mutat. Res. 195(2):137-149; 1988.
71. 71. Brambilla, G.; Martelli, A.; Marinari, U. M. Is lipid peroxidation associated with DNA damage? Mutat Res. 214(1):123-127; 1989.
72. 72. Kern, W.; Spiteller, G. Synthesis and properties of natural occurring α-hydroxyaldehydes. Tetrahedron 52(12):4347-4362; 1996.
73. 73. Heinle, H.; Gugeler, N.; Felde, R.; Spiteller, G. Oxidation of plasmalogens produce highly effective modulators of macrophage function. Chem. Phys. Lipids 1996 (in press).
74. 74. Jira, W.; Spiteller, G.; Schramm, A. Increased levels of hydroxyacids in low density lipoproteins obtained from patients with atherosclerosis. Chem. Phys. Lipids 1996 (in press).
75. 75. Jira, W.; Spiteller, G. Plasmalogens and their oxidative degradation products in low and high density lipoprotein. Chem. Phys. Lipids 79:95-100; 1996.
76. 76. Morand, O. H.; Zoeller, R. A.; Raetz, C. R. H. Disappearance of plasmalogens from membranes of animal cells subjected to photosensitized oxidation. J. Biol. Chem. 263(33):11597-12606; 1988.
77. 77. Meyer, C.; Lutz, A.; Spiteller, G. α-Hydroxyaldehyde derivatives as secondary products of the oxidation of plasmalogens. Angew. Chem. 104(4):491-492; 1992; Angew. Chem. Int. Ed. Engl. 31(4):468-470; 1992
78. 77. Meyer, C.; Lutz, A.; Spiteller, G. α-Hydroxyaldehyde derivatives as secondary products of the oxidation of plasmalogens. Angew. Chem. 104(4):491-492; 1992; Angew. Chem. Int. Ed. Engl. 31(4):468-470; 1992
79. 78. Rouser, G.; Yamamoto, A. Curvilinear regression course of human brain lipid composition changes with age. Lipids 3(3):284-281; 1968.
80. 79. Cornwell, D. G.; Morisaki, N. Fatty acid paradoxes in the control of cell proliferation: Prostaglandins, lipid peroxides, and cooxidation reactions. In: Pryor, W. A. ed. Free radicals in biology. Vol. VI. New York: Academic Press; 1984:95-148.
81. 80. Goldstein, S. The biology of aging. N. Engl. J. Med. 285(20):1120-1129; 1971.
82. 81. Harman, D. The aging process. Proc. Natl. Acad. Sci. USA 78(11):7124-7128; 1981.
83. 82. Segerbaeck, D. Alkylation of DNA and hemoglobin in the mouse following exposure to ethene and ethene oxide. Chem.-Biol. Interact. 45(2):139-151; 1983.
84. 83. Svensson, K.; Olofsson, K.; Osterman-Golkar, S. Alkylation of DNA and hemoglobin in the mouse following exposure to propene and propylene oxide. Chem.-Biol. Interact. 78(1):55-66; 1991.
85. 84. van Sittert, N. J.; Beulink, G. D. J.; van Vliet, E. W. N. Monitoring occupational exposure to ethylene oxide by the determination of hemoglobin adducts. Environ. Health. Perspect. 99:217-220; 1993.