An esterification protocol for cis-parinaric acid-determined lipid peroxidation in immune cells

Lipids

Volumn 32, Issue 2, 1997, Pages 219-226

  McGuire, Susan O ^a,b   James Kracke, Marilyn R ^b   Sun, Grace Y ^b   Fritsche, Kevin L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

^b University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL; BOVINE SERUM ALBUMIN; EDETIC ACID; LIPID PEROXIDE; MEMBRANE PHOSPHOLIPID; PARINARIC ACID; POLYUNSATURATED FATTY ACID;

ANIMAL CELL; ARTICLE; CELL MEMBRANE; CONTROLLED STUDY; ESTERIFICATION; FLUORESCENCE; IMMUNOCOMPETENT CELL; LIPID COMPOSITION; LIPID PEROXIDATION; MACROPHAGE; MOUSE; NONHUMAN; OXIDATIVE STRESS;

CELLS, CULTURED; CHROMATOGRAPHY, GAS; FATTY ACIDS, UNSATURATED; FLUORESCENT DYES; LIPID PEROXIDATION; TIME FACTORS;

EID: 0031044125     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-997-0028-x     Document Type: Article

References (56)

1. Barzanti, V., Pregnolato, P., Maranesi, M., Bosi, I., Baracca, A., Solaini, G., and Turchetto, E. (1995) Effect of Dietary Oils Containing Graded Amounts of 18:3 (n-6) and 18:4 (n-3) on Cell Plasma Membranes, J. Nutr. Biochem. 6, 21-26.
2. Galli, C., Tremoli, E., Stragliotto, E., and Sirtori, C. (1995) Treatment with Omega-3 Fatty Acid Ethyl Esters in Hyperlipoproteinaemias: Comparative Studies on Lipid Metabolism and Thrombotic Indexes, Pharmacol. Res. 31, 1-8.
3. Cosgrove, J., Church, D., and Pryor, W. (1987) The Kinetics of the Autoxidation of Polyunsaturated Fatty Acid, Lipids 22, 299-304.
4. Garrido, A., and Garrido, F. (1989) Ingestion of High Doses of Fish Oil Increases the Susceptibility of Cellular Membranes to the Induction of Oxidative Stress, Lipids 24, 833-835.
5. Cho, S., and Choi, Y. (1994) Lipid Peroxidation and Antioxidant Status Is Affected by Different Vitamin E Levels When Feeding Fish Oil, Lipids 29, 47-52.
6. Hu, M.L., Frankel, E.N., Leibovitz, B.E., and Tappel, A.L. (1989) Effect of Dietary Lipids and Vitamin E on in vitro Lipid Peroxidation in Rat Liver and Kidney Homogenates, J. Nutr. 119, 1574-1582.
7. Hu, M.L., Frankel, E.N., and Tappel, A.L. (1990) Effect of Dietary Menhaden Oil and Vitamin E on in vivo Lipid Peroxidation Induced by Iron, Lipids 25, 194-198.
8. Javouhey-Donzel, A., Guenot, L., Maupoil, V., Rochette, L., and Rocquelin, G. (1993) Rat Vitamin E Status and Heart Lipid Peroxidation: Effect of Dietary α-Linolenic Acid and Marine n-3 Fatty Acids, Lipids 28, 651-655.
9. Mouri, K., Ikesu, H., Esaka, T., and Igarashi, O. (1984) The Influence of Marine Oil Intake Upon Levels of Lipids, α-Tocopherol and Lipid Peroxidation in Serum and Liver of Rats, J. Nutr. Sci. Vitaminol. 30, 307-318.
10. Meydani, M., Natiello, F., Goldin, B., Free, N., Woods, M., Schaefer, E., Blumberg, J., and Gorbach, S. (1991) Effect of Long-Term Fish Oil Supplementation on Vitamin E Status and Lipid Peroxidation in Women, J. Nutr. 121, 484-491.
11. Nair, P.P., Judd, J.R., Berlin, E., Taylor, P.R., Shami, S., Sainz, E., and Bhagavan, H.N. (1993) Dietary Fish Oil-Induced Changes in the Distribution of α-Tocopherol, Retinol, and β-Carotene in Plasma, Red Blood Cells, and Platelets: Modulation by Vitamin E, Amer. J. Clin. Nutr. 58, 98-102.
12. Comporti, M. (1993) Lipid Peroxidation. An Overview. Free Radical from Basic Science to Medicine (Poli, G., Albano, E., and Dianzani, M., eds.) pp. 65-79, Birkhauser Verlag Basel.
13. Gutteridge, J., and Halliwell, B. (1990) The Measurement and Mechanism of Lipid Peroxidation in Biological Systems, TIBS 15, 129-135.
14. Alexander, D.W., McGuire, S.O., Cassity, N.A., and Fritsche, K.L. (1995) Fish Oils Lower Rat Plasma and Hepatic, But Not Immune Cell α-Tocopherol Concentration, J. Nutr. 125, 2640-2649.
15. Fritsche, K.L., Cassity, N.A., and Huang, S.S. (1992) Dietary (n-3) Fatty Acid and Vitamin E Interactions in Rats: Effects on Vitamin E Status, Immune Cell Prostaglandin E Production and Primary Antibody Response, J. Nutr. 122, 1009-1018.
16. McKenna, R., Kezdy, F., and Epps, D. (1991) Kinetic Analysis of the Free-Radical-Induced Lipid Peroxidation in Human Erythrocyte Membranes: Evaluation of Potential Antioxidants Using cis-Parinaric Acid to Monitor Peroxidation, Anal. Biochem. 196, 443-450.
17. Meydani, S.N., Shapiro, A.C., Meydani, M., Macauley, J.B., and Blumberg, J.B. (1987) Effect of Age and Dietary Fat (Fish, Corn and Coconut Oils) on Tocopherol Status of C57BL/6Nia Mice, Lipids 22, 345-350.
18. Muggli, R. (1989) Dietary Fish Oils Increase the Requirement for Vitamin E in Humans, in Health Effects of Fish Oils (Chandra, R.K., ed.) pp. 201-210, ARTS Biomedical Publishers & Distributors, St. John's, Newfoundland, Canada.
19. Muggli, R. (1994) Physiological Requirements of Vitamin E as a Function of the Amount and Type of Polyunsaturated Fatty Acid, in Fatty Acids and Lipids: Biological Aspects, World Rev. Nutr. Diet (Galli, D., Simopoulos, A., and Tremoli, E., eds.) Karger, Basel, Switzerland, pp. 166-168.
20. Coquette, A., Vray, B., and Vanderpas, J. (1986) Role of Vitamin E in the Protection of the Resident Macrophage Membrane Against Oxidative Damage, Arch. Intl. Physiol. Biochim. 94, S29-S34.
21. Pacht, E.R., Kaseki, H., Mohammed, J.R., Cornwell, D.G., and Davis, W.B. (1986) Deficiency of Vitamin E in the Alveolar Fluid of Cigarette Smokers: Influence on Alveolar Macrophage Cytotoxicity, J. Clin. Invest. 77, 789-796.
22. Halliwell, B., and Chirico, S. (1993) Lipid Peroxidation: Its Mechanism, Measurement, and Significance, Am. J. Clin. Nutr. 57(suppl), 715-725.
23. Halliwell, B. (1994) Free Radicals and Antioxidants: A Personal View, Nutr. Rev. 52, 253-265.
24. Kuypers, F., Van den Berg, J., Schalkwijk, C., Roelofsen, B., and Op den Kamp, J. (1987) Parinaric Acid as a Sensitive Fluorescent Probe for the Determination of Lipid Peroxidation, Biochim. Biophy. Acta 921, 266-274.
25. Van den Berg, J., De Fouw, N., Kuypers, F., Roelofsen, B., Houtsmuller, U., and Op den Kamp, J. (1991) Increased (n-3) Polyunsaturated Fatty Acid Content of Red Blood Cells from Fish Oil-Fed Rabbits Increases in vitro Lipid Peroxidation, But Decreases Hemolysis, Free Rad. Biol. Med. 11, 393-399.
26. Van den Berg, J., Kuypers, F., Lubin, B., Roelofsen, B., and Op den Kamp, J. (1991) Direct and Continuous Measurement of Hydroperoxide-Induced Oxidative Stress on the Membrane of Intact Erythrocytes, Free Rad. Biol. Med. 11, 255-261.
27. Fritsche, K.L., and Johnson, P.V. (1990) Effect of Dietary α-Linolenic Acid on Growth, Metastasis, Fatty Acid Profile and Prostaglandin Production of Two Murine Mammary Adenocarcinomas, J. Nutr. 120, 1601-1609.
28. Sun, G. (1988) Preparation and Analysis of Acyl and Alkenyl Groups of Glycerophospholipids from Brain Subcellular Membranes, in Lipids and Related Compounds (Boulton, A.A., Baker, G.B., and Horrocks, L.A., eds.) pp. 63-81, Humana Press, Clifton, New Jersey.
29. Sklar, L., Hudson, B., Petersen, M., and Diamond, J. (1977) Conjugated Polyene Fatty Acids on Fluorescent Probes: Spectroscopic Characterization, Biochemistry 16, 813-818.
30. Gutteridge, J.M. (1984) Ferrous Ion-EDTA-StimuIated Phospholipid Peroxidation, Biochem. J. 224, 697-701.
31. Fukuzawa, K., and Fujii, R. (1992) Peroxide Dependent and Independent Lipid Peroxidation: Site-Specific Mechanisms of Initiation by Chelated Iron and Inhibition by α-Tocopherol, Lipids 27, 227-233.
32. Minotti, G., and Aust, S.D. (1992) Redox Cycling of Iron and Lipid Peroxidation, Lipids 27, 219-226.
33. Gill, J. L., and Hafs, H.D. (1971) Analysis of Repeated Measurements of Animals, J. Anim. Sci. 33, 331-335.
34. SAS (1985) SAS User's Guide: Statistics (5th edn.), SAS Institute Inc., Cary, NC.
35. Carmer, S.G., and Seif, R.D. (1963) Calculation of Orthogonal Coefficients When Treatments Are Unequally Replicated and/or Unequally Spaced, Agron. J. 55, 387-391.
36. Snedecor, G.W., and Cochran, W.G. (1967) Statistical Methods (6th edn.), Iowa State University Press, Ames.
37. Van den Berg, J., Kuypers, F., Qju, J., Chiu, D., Lubin, B., Roelofsen, B., and Op den Kamp, J. (1988) The Use of cis-Parinaric Acid to Determine Lipid Peroxidation in Human Erythrocyte Membranes. Comparison of Normal and Sickle Erythrocyte Membranes, Biochim. Biophys. Acta 944, 29-39.
38. Van den Berg, J., Kuypers, F., Roelofsen, B., and Op den Kamp, J. (1990) The Cooperative Action of Vitamins E and C in the Protection Against Peroxidation of Parinaric Acid in Human Erythrocyte Membranes, Chem. Phys. Lipids 53, 309-320.
39. Custodio, J., Dinis, T., Almeida, L., and Madeira, V. (1994) Tamoxifen and Hydroxytamoxifen as Intramembraneous Inhibitors of Lipid Peroxidation. Evidence for Peroxyl Radical Scavenging Activity, Biochem. Pharmacol. 47, 1989-1998.
40. Dinis, T., Almeida, L., and Madeira, V. (1993) Lipid Peroxidation in Sarcoplasmic Reticulum Membranes: Effect on Functional and Biophysical Properties, Arch. Biochem. Biophys. 301, 256-264.
41. Simoes, A., Van den Berg, J., Roelofsen, B., and Op den Kamp, J. (1992) Lipid Peroxidation in Plasmodium falciparum-Parasitized Human Erythrocytes, Arch. Biochem. Biophys. 298, 651-657.
42. Van den Berg, J., Op den Kamp, J., Lubin, B., Roelofsen, B., and Kuypers, F. (1992) Kinetics and Site Specificity of Hydroperoxide-Induced Oxidative Damage in Red Blood Cells, Free Rad. Biol. Med. 12, 487-498.
43. Hedley, D., and Chow, S. (1992) Flow Cytometric Measurement of Lipid Peroxidation in Vital Cells Using Parinaric Acid, Cytometry 13, 686-692.
44. Tsuchiya, M., Kagan, V., Freisleben, H., Manabe, M., and Packer, L. (1994) Antioxidant Activity of α-Tocopherol, β-Carotene, and Ubiquinol in Membranes cis-Parinaric Acid-Incorporated Liposomes, Methods Enzymol. 234, 371-383.
45. de Hingh, Y.C.M., Meyer, J., Fischer, J.C., Berger, R., Smeitink, J.A.M., and Op den Kamp, J.A.F. (1995) Direct Measurement of Lipid Peroxidation in Submitochondrial Particles, Biochemistry 34, 12755-12760.
46. Sklar, L., and Dratz, E. (1980) Analysis of Membrane Bilayer Asymmetry Using Parinaric Acid Fluorescent Probes, FEBS Lett. 118, 308-310.
47. Harris, W., and Stahl, W. (1983) Incorporation of cis-Parinaric Acid, a Fluorescent Fatty Acid, into Synaptosomal Phospholipids by an Acyl-CoA Acyltransferase, Biochim. Biophys. Acta 736, 79-91.
48. Stuhne-Sekalec, L., Denes, A., and Stanacev, N. (1985) Biosynthetic Incorporation of cis-Parinaric Acid into Radioactive sn-3-Phosphatidic Acid, Prep. Biochem. 15, 35-47.
49. Erin, A.N., Spirin, M.M., Tabidze, L.V., and Kagan, V.E. (1984) Formation of α-Tocopherol Complexes with Fatty Acids, A Hypothetical Mechanism of Stabilization of Biomembranes by Vitamin E, Biochim. Biophy. Acta 774, 96-102.
50. Schroeder, F., Myers-Paye, S., Billheimer, J., and Wood, G. (1995) Probing the Ligand Binding Sites of Fatty Acid and Sterol Carrier Proteins: Effects of Ethanol, Biochemistry 34, 11919-11927.
51. Rintoul, D., and Simoni, R. (1977) Incorporation of a Naturally Occurring Fluorescent Fatty Acid into Lipids of Cultured Mammalian Cells, J. Biol. Chem. 252, 7916-7918.
52. Prows, D.R., Murphy, E.J., and Schroeder, F. (1995) Intestinal and Liver Fatty Acid Binding Proteins Differentially Affect Fatty Acid Uptake and Esterification in L-Cells, Lipids 30, 907-910.
53. Kagan, V.E. (1989) Tocopherol Stabilizes Membrane Against Phospholipase A, Free Fatty Acids, and Lysophospholipids, Ann. N.Y. Acad. Sc. 570, 121-135.
54. Lucy, J.A. (1972) Functional and Structural Aspects of Biological Membranes: A Suggested Structural Role for Vitamin E in the Control of Membrane Permeability and Stability, Ann. N.Y. Acad. Sci. 203, 3-16.
55. Patel, J.M., Sekharam, M., and Block, E.R. (1991) Vitamin E Distribution and Modulation of the Physical State and Function of Pulmonary Endothelial Cell Membranes, Exp. Lung Res. 17, 707-723.
56. Urano, S., Matsuo, M., Sakanaka, R., Uemura, I., Koyama, M., Kumadaki, I., and Fukuzawa, K. (1993) Mobility and Molecular Orientation of Vitamin E in Liposomal Membranes as Determined by 19F NMR and Fluorescence Polarization Techniques, Arch. Biochem. Biophy. 303, 10-14.