Skip to main content
SpringerLink
Log in

Response of urinary lipophilic aldehydes and related carbonyl compounds to factors that stimulate lipid peroxidation in vivo

  • Published:
Lipids

Abstract

Peroxidation of lipids results in the formation of a number of aldehydic and other carbonyl-containing secondary degradation products. The effect of peroxidative stimuli mediated by vitamin E deficiency, a diet high in polyunsaturated fatty acids (containing cod liver oil), and carbon tetrachloride administration on urinary excretion of a number of lipophilic aldehydes and related carbonyl compounds was examined in rats. These secondary lipid peroxidation products were measured as 2,4-dinitrophenylhydrazine derivatives. All three treatments increased urinary excretion of secondary lipid peroxidation products, although the pattern of excretion of these products varied somewhat among the treatments. Significant increases were found in butanal, hexanal, octanal. butan-2-one, pentan-2-one, hex-2-enal, hepta-2,4-dienal, 4-hydroxyhex-2-enal, 4-hydroxyoct-2-enal, 4-hydroxynon-2-enal, and a number of unidentified carbonyl compounds. These results suggest that urinary excretion of these lipophilic secondary lipid peroxidation products is a useful and noninvasive marker of whole-body lipid peroxidation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

CCl4 :

carbon tetrachloride

CH2Cl2 :

dichloromethane

CLO:

cod liver oil

CO:

corn oil

DNPH:

2,4-dinitrophenylhydrazine

E:

vitamin E deficiency

HE:

high vitamin E

HHE:

4-hydroxyhex-2-enal

HNE:

hydroxynon-2-enal

HOE:

4-hydroxyoct-2-enal

HPLC:

high-performance liquid chromatography

MDA:

malondialdehyde

NE:

normal vitamin E

NONPOL:

nonpolar carbonyl compounds

POL:

polar carbonyl compounds

PUFA:

polyunsaturated fatty acids

TLC:

thin-layer chromatography

References

  1. De Groot, H. (1994) Reactive Oxygen Species in Tissue Injury, Hepatogastroenterol 41, 328–332.

    Google Scholar 

  2. Halliwell, B. (1994) Free Radicals and Antioxidants: A Personal View, Nutr. Rev. 52, 253–265.

    Article  PubMed  CAS  Google Scholar 

  3. Packer, L. (1991) Protective Role of Vitamin E in Biological Systems, Am. J. Clin. Nutr. 53 (Suppl. 4), 1050S-1055S.

    PubMed  CAS  Google Scholar 

  4. Burton, G.W. (1994) Vitamin E: Molecular and Biological Function, Proc. Nutr. Soc. 53, 251–262.

    Article  PubMed  CAS  Google Scholar 

  5. Maellaro, E., Casini, A.F., Bello, B.D., and Comporti, M. (1990) Lipid Peroxidation and Antioxidant Systems in the Liver Injury Produced by Glutathione-Depleted Agents, Biochem. Pharmacol. 39, 1513–1521.

    Article  PubMed  CAS  Google Scholar 

  6. Niki, E., Yamamoto, Y., Komuro, E., and Sato, K. (1991) Membrane Damage Due to Lipid Oxidation, Am. J. Clin. Nutr. 53, 201S-205S.

    PubMed  CAS  Google Scholar 

  7. Blanchflower, W.J., Walsh, D.M., Kennedy, S., and Kennedy, D.G. (1993) A Thermospray Mass Spectrometric Assay for Fe-Induced 4-Hydroxynonenal in Tissues, Lipids 28, 261–264.

    PubMed  CAS  Google Scholar 

  8. Dratz, E.A., Garnsworth, C.F., Loew, E.C., Stephens, R.J., Thomas, D.W., and Van Kuijk, F.J.G.M. (1989) Products of in vivo Peroxidation Are Present in Tissues of Vitamin E-Deficient Rats and Dogs, Ann. N.Y. Acad. Sci. 570, 46–60.

    PubMed  CAS  Google Scholar 

  9. Cosgrove, J.P., Church, D.F., and Pryor, W.A. (1987) The Kinetics of the Autoxidation of Polyunsaturated Fatty Acids, Lipids 22, 299–304.

    PubMed  CAS  Google Scholar 

  10. Wills, E.D. (1985) The Role of Dietary Components in Oxidative Stress in Tissues, in Oxidative Stress (Sies, H., ed.) pp. 197–216, Academic Press, London.

    Google Scholar 

  11. Spector, A.A., and Yorek, M.A. (1985) Membrane Lipid Composition and Cellular Function, J. Lipid Res. 26, 1015–1035.

    PubMed  CAS  Google Scholar 

  12. Hart, C.M., Tolson, J.K., and Block, E.R. (1991) Supplemental Fatty Acids Alter Lipid Peroxidation and Oxidant Injury in Endothelial Cells, Am. J. Physiol. 260, L481-L488.

    PubMed  CAS  Google Scholar 

  13. Smith, D.L., Willis, A.L., Nguyen, N., Conner, D., Zahedi, S., and Fulks, J. (1989) Eskimo Plasma Constituents, Dihomo-γ-linolenic Acid, Eicosapentaenoic Acid, and Docosahexaenoic Acid Inhibitit the Release of Atherogenic Mitogens, Lipids 24, 70–75.

    PubMed  CAS  Google Scholar 

  14. Zöllner, N., and Tatò, F. (1992) Fatty Acid Composition of the Diet: Impact on Serum Lipids and Atherosclerosis, Clin. Invest. 70, 968–1009.

    Google Scholar 

  15. 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.

    PubMed  CAS  Google Scholar 

  16. Kaasgaard, S.G., Homer, G., Hoy, C.E., Behrens, W.A., and Beare-Rogers, J.L. (1992) Effects of Dietary Linseed Oil and Marine Oil on Lipid Peroxidation in Monkey Liver in vivo and in vitro, Lipids 27, 740–745.

    PubMed  CAS  Google Scholar 

  17. Lamers, J.M., Hartog, J.M., Guarnieri, C., Vaona, I., Verdouw, P.D., and Koster, J.F. (1988) Lipid Peroxidation in Normotic and Ischaemic-Reperfused Heart of Fish Oil and Lard Fat Fed Pigs, J. Mol. Cell Cardiol. 20, 605–615.

    Article  PubMed  CAS  Google Scholar 

  18. Connor, H.D., Thurman, R.G., Galizi, M.D., and Mason, R.P. (1986) The Formation of a Novel Free Radical Metabolite from CCl4 in the Perfused Rat Liver and in vivo, J. Biol. Chem. 261, 4542–4548.

    PubMed  CAS  Google Scholar 

  19. Schauenstein, E. (1967) Autoxidation of Polyunsaturated Esters in Water: Chemical Structure And Biological Activity of the Products, J. Lipid Res. 8, 417–428.

    PubMed  CAS  Google Scholar 

  20. Benedetti, A., Comporti, M., and Esterbauer, H. (1980) Identification of 4-Hydroxynonenal As a Cytotoxic Product Originating from the Peroxidation of Liver Microsomal Lipids, Biochim. Biophys. Acta 620, 281–96.

    PubMed  CAS  Google Scholar 

  21. Esterbauer, H., Zollner, H., and Schaur, R.J. (1990) Aldehydes Formed by Lipid Peroxidation: Mechanisms of Formation, Occurrence, and Determination, in Membrane Lipid Peroxidation (Vigo-Pelfrey, C., ed.) pp. 240–268, CRC Press, Boca Raton.

    Google Scholar 

  22. Esterbauer, H., Schaur, R.J., and Zollner, H. (1991) Chemistry and Biochemistry of 4-Hydroxynonenal, Malonaldehyde, and Related Aldehydes, Free Rad. Biol. Med. 11, 81–128.

    Article  PubMed  CAS  Google Scholar 

  23. Comporti, M. (1989) Three Models of Free Radical-Induced Cell Injury, Chem.-Biol. Interact. 72, 1–56.

    Article  PubMed  CAS  Google Scholar 

  24. Eckl, P.M., Ortner, A., and Esterbauer, H. (1993) Genotoxic Properties of 4-Hydroxyalkenals and Analogous Aldehydes, Mutat. Res. 290, 183–192.

    PubMed  CAS  Google Scholar 

  25. Witz, G. (1989) Biological Interactions of α,β-Unsaturated Aldehydes, Free Rad. Biol. Med. 7, 333–349.

    Article  PubMed  CAS  Google Scholar 

  26. Kanazawa, K., and Ashida, H. (1991) Target Enzymes on Hepatic Dysfunction Caused by Dietary Products of Lipid Peroxidation, Arch. Biochem. Biophys. 288, 71–78.

    Article  PubMed  CAS  Google Scholar 

  27. Comporti, M. (1993) Lipid Peroxidation: Biopathological Significance, Molec. Aspects Med. 14, 199–207.

    Article  CAS  Google Scholar 

  28. Kim, S.-S., Gallaher, D.D., and Csallany, A.S. (1999) Lipophilic Aldehydes and Related Carbonyl Compounds in Rat and Human Urine, Lipids 34, 489–496.

    PubMed  Google Scholar 

  29. Cheronis, N.D., and Entrikin, I.B. (1961) Derivatives of Aldehydes, in Semimicro Qualitative Organic Analysis, pp. 388–401, Interscience, Ltd., London.

    Google Scholar 

  30. Lee, H.-S., Shoeman, D.W., and Csallany, A.S. (1992) Urinary Response to in vivo Lipid Peroxidation Induced by Vitamin E Deficiency, Lipids 27, 124–128.

    PubMed  CAS  Google Scholar 

  31. Kim, S.-S., Gallaher, D.D., and Csallany, A.S. (1999) Lipophilic Aldehydes and Related Carbonyl Compounds in Rat and Human Urine, Lipids 34, 489–496.

    PubMed  Google Scholar 

  32. Sonnenwirth, A.C., and Jarett, L. (1980) Gradwhohl’s Clinical Laboratory Methods and Diagnosis, Vol. 1, pp. 507–509, St. Louis.

  33. Lee, H.-S., Shoeman, D.W., and Csallany, A.S. (1992) Urinary Response to in vivo Lipid Peroxidation Induced by Vitamin E Deficiency, Lipids 27, 124–128.

    PubMed  CAS  Google Scholar 

  34. Packer, L., and Landvik, S. (1989) Vitamin E: Introduction to Biochemistry and Health Benefits, Ann. N.Y. Acad. Sci. 570, 1–6.

    PubMed  CAS  Google Scholar 

  35. Yoshino, K., Sano, M., Fujita, M., and Tomita, I. (1990) Studies on the Formation of Aliphatic Aldehydes in the Plasma and Liver of Vitamin E-Deficient Rats, Chem. Pharm. Bull. 38, 2212–2215.

    PubMed  CAS  Google Scholar 

  36. Esterbauer, H., Gunther, J., Quehenberger, O., and Koller, E. (1987) Autoxidation of Human Low Density Lipoprotein: Loss of Polyunsaturated Fatty Acids and Vitamin E and Generation of Aldehydes, J. Lipid Res. 28, 495–509.

    PubMed  CAS  Google Scholar 

  37. Snijders, C.P., Schouten, J.A., De Jong, A.P., and Van Der Veen, E.A. (1984) Effect of Dietary Cod-Liver Oil on the Lipid Composition of Human Erythrocyte Membranes, Scand. J. Clin. Lab, Invest. 44, 39–46.

    Google Scholar 

  38. Javouhey, A., Rocquelin, G., Rochette, L., and Juaneda, P. (1990) Comparative Effects of Equivalent Intakes of 18∶3 (n−3) and of Marine (n−3) Fatty Acids on Rat Cardiac Phospholipid Contents and Fatty Acid Compositions, Nutr. Res. (N.Y.) 10, 291–301.

    Article  CAS  Google Scholar 

  39. Rao, C.V., Zang, E., and Reddy, B.S. (1993) Effect of High Fat Corn Oil, Olive Oil, and Fish Oil on Phospholipid Fatty Acid Composition in Male F344 Rats, Lipids 28, 441–447.

    PubMed  CAS  Google Scholar 

  40. Van Den Boom, M.A.P., Wassink M.G., Roelofsen, B., De Fouw, N.J., and Op Den Kamp, J.A.F. (1996) The Influence of a Fish Oil-Enriched Diet on the Phospholipid Fatty Acid Turnover in the Rabbit Red Cell Membrane in vivo, Lipids 31, 285–293.

    PubMed  Google Scholar 

  41. Burns, A., Lin, Y., Gibson, R., and Jamieson, D. (1991) The Effect of a Fish Oil-Enriched Diet on Oxygen Toxicity and Lipid Peroxidation in Mice, Biochem. Pharmacol. 42, 1353–1360.

    Article  PubMed  CAS  Google Scholar 

  42. Van Den Berg, J.J.M., De Fouw, N.J., Kuypers, F.A., Roelofsen, B., Houtsmuller, U.M.T., and Op Den Kamp, J.A.F. (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 Radical Biol. Med. 11, 393–399.

    Article  Google Scholar 

  43. Saito, M., and Nakatsugawa, K. (1994) Increased Susceptibility of Liverto Lipid Peroxidation After Ingestion of a High Fish Oil Diet, Internat. J. Vit. Nutr. Res. 64, 144–151.

    CAS  Google Scholar 

  44. Spitz, D.R., Kinter, M.T., Kehrer, J.P., and Roberts, R.J. (1992) The Effect of Monosaturated and Polyunsaturated Fatty Acids on Oxygen Toxicity in Cultured Cells, Pediatr. Res. 32, 366–372.

    PubMed  CAS  Google Scholar 

  45. Hart, C.M., Tolson, J.K., and Block, E.R. (1991) Supplemental Fatty Acids Alter Lipid Peroxidation and Oxidant Injury in Endothelial Cells, Am. J. Physiol 260, L481-L488.

    PubMed  CAS  Google Scholar 

  46. Javouhey-Donzel, A., Guenot, L., Maupoil, V., Rochette, L., and Rocquelin, G. (1993) α-Linolenic Acid and Marine n−3 Fatty Acids, Lipids 28, 651–655.

    PubMed  CAS  Google Scholar 

  47. Nair, P.P., Judd, J.T., 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, Am. J. Clin Nutr. 58, 98–102.

    PubMed  CAS  Google Scholar 

  48. Cheeseman, K.H., Albano, E.F., Tomasi, A., and Slater, T.F. (1985) Biochemical Studies on the Metabolic Activtion of Halogenated Alkanes, Environ. Health Perspect. 64, 85–101.

    PubMed  CAS  Google Scholar 

  49. Benedetti, A., Fulceri, R., Ferrali, M., Ciccoli, L., Esterbauer, H., and Comporti, M. (1982) Detection of Carbonyl Function in Phospholipids of Liver Microsomes in CCl4- and BrCCl3-Poisoned Rats, Biochim. Biophys. Acta 712, 628–638.

    PubMed  CAS  Google Scholar 

  50. Goldring, C., Casini, A.F., Maellaro, E., Bello, B.D., and Comporti, M. (1993) Determination of 4-Hydroxynonenal by High-Performance Liquid Chromatography with Electrochemical Detection, Lipids 28, 141–145.

    PubMed  CAS  Google Scholar 

  51. Poli, G., Cheeseman, K.H., Biasi, F., Chiarpotto, E., Dianzani, M.U., Esterbauer, H., and Slater, T.F. (1989) Promethazine Inhibits the Formation of Aldehydic Products of Lipid Peroxidation But Not Covalent Binding Resulting from the Exposure of Rat Liver Fractions to CCl4, Biochem. J. 264, 527–532.

    PubMed  CAS  Google Scholar 

  52. Poli, G., Dianzani, M.U., Cheeseman, K.H., Slater, T.F., Lang, J., and Esterbauer, H. (1985) Separation and Characterization of the Aldehydic Products of Lipid Peroxidation Stimulated by Carbon Tetrachloride or ADP-Iron in Isolated Rat Hepatocytes and Rat Liver Microsomal Suspensions, Biochem. J. 227, 629–638.

    PubMed  CAS  Google Scholar 

  53. Dhanakoti, S.N., and Draper, H.H. (1987) Response of Urinary Malonaldehyde to Factors That Stimulate Lipid Peroxidation in vivo, Lipids 22, 643–646.

    PubMed  CAS  Google Scholar 

  54. Alary, J., Bravais, F., Cravedi, J.P., Debrauwer, L., Rao, D., and Bones, G. (1995) Mercapturic Acid Conjugates as Urinary End Metabolites of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal in the Rat, Chem. Res. Toxicol. 8, 34–39.

    Article  PubMed  CAS  Google Scholar 

  55. Winter, C.K., Segall, H.J., and Jones, A.D. (1987) Distribution of trans-4-hydroxy-2-hexenal and Tandem Mass Spectrometric Detection of Its Urinary Mercapturic Acid in the Rat, Drug Metab. Dispos. 15, 608–612.

    PubMed  CAS  Google Scholar 

  56. Esterbauer, H., and Zollner, H. (1989) Methods for Determination of Aldehydic Lipid Peroxidation Products, Free Rad. Biol. Med. 7, 197–203.

    Article  PubMed  CAS  Google Scholar 

  57. Esterbauer, H., and Zollner, H. (1989) Methods for Determination of Aldehydic Lipid Peroxidation Products, Free Rad. Biol. Med. 7, 197–203.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Science and Nutrition, University of Minnesota, 1334 Eckles Ave, 55108, St. Paul, Minnesota

    A. Saari Csallany, Song-Suk Kim & Daniel D. Gallaher

Authors
  1. A. Saari Csallany
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Song-Suk Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Daniel D. Gallaher
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Saari Csallany.

About this article

Cite this article

Csallany, A.S., Kim, SS. & Gallaher, D.D. Response of urinary lipophilic aldehydes and related carbonyl compounds to factors that stimulate lipid peroxidation in vivo . Lipids 35, 855–862 (2000). https://doi.org/10.1007/S11745-000-0594-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/S11745-000-0594-y

Keywords

Search

Navigation