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Lipophilic aldehydes and related carbonyl compounds in rat and human urine

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Lipids

Abstract

Rat and human urine samples were analyzed for lipophilic aldehydes and other carbonyl products of lipid peroxidation. The following compounds were identified as their 2,4-dinitrophenyl hydrazones by cochromatography with pure standards using three solvent systems: butanal, butan-2-one, pentan-2-one, hex-2-enal, hexanal, hepta-2,4-dienal, hept-2-enal, octanal, non-2-enal, deca-2,4-dienal, 4-hydroxyhex-2-enal, and 4-hydroxynon-2-enal. In general, fasted rats excreted less of these compounds than fed rats, indicating they were partially of dietary origin or that the endogenous compounds were excreted in a form not susceptible to hydrazone formation. The compounds excreted in human urine were similar to those excreted in rat urine but were present in lower concentrations. Identification of the conjugated forms fo the lipophilic aldehydes and related carbonyl compounds excreted in urine may be a source of information about their reactions in vivo.

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Abbreviations

DNPH:

2,4-dinitrophenylhydrazine

DNP-hydrazones:

2,4-dinitropheaylhydrazones

HNE:

4-hydroxynon-trans-2-enal

HPLC:

high-performance liquid chromatography

MDA:

mationdialdehyde

MeOH:

methanol

NONPOL:

nonpolar carbonyl compounds

POL:

polar carbonyl compounds

TLC:

thin layer chromatography

References

  1. Yagi, K. (1987) Lipid Peroxides and Human Diseases, Chem. Phys. Lipids 45, 337–351.

    Article  PubMed  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    PubMed  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  8. Szweda, L., Uchida, K., Tsai, L., and Stadtman, E.R. (1993) Inactivation of Glucose-6-phosphate Dehydrogenase by 4-Hydroxy-2-nonenal, J. Biol. Chem. 268, 3342–3347.

    PubMed  CAS  Google Scholar 

  9. Esterbauer, H., Zollner, H., and Schaur, R.J. (1988) Hydroxyalkenals: Cytotoxic Products of Lipid Peroxidation, ISI Atlas Sci. Biochem. 1, 311–317.

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. Buffinton, G.D., Hunt, N.H., Cowdden, W.B., and Clark, I.A. (1988) Detection of Short-Chain Carbonyl Products of Lipid Peroxidation from Malaria-Parasite (Plasmodium vinokei)-Infected Red Blood Cells Exposed to Oxidative Stress, Biochem. J. 249, 63–68.

    PubMed  CAS  Google Scholar 

  12. Frankel, E.N., and Tappel, A.L. (1991) Headspace Gas Chromatography of Volatile Lipid Peroxidation products from Human Red Cell Membranes, Lipids 26, 479–484.

    PubMed  CAS  Google Scholar 

  13. 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 Isolated Rat Hepatocytes and Rat Liver Microsomal Suspensions, Biochem. J. 227, 629–638.

    PubMed  CAS  Google Scholar 

  14. Beckman, J.K., Morley, S., and Greene, H.L. (1991) Analysis of Aldehydie Lipid Peroxidation Products by TLC/Densitometry, Lipids 26, 155–161.

    PubMed  CAS  Google Scholar 

  15. Frankel, E.N., Hu, M.L., and Tappel, A.L. (1989) Rapid Head Gas Chromatography of Hexanal as a Measure of Lipid Peroxidation in Biological Samples, Lipids 24, 976–981.

    PubMed  CAS  Google Scholar 

  16. Esterbauer, H., Cheeseman, K.H., Dianzani, M.U., Poli, G., and Slater, T.F. (1982) Separation and Characterization of the Aldehydic Products of Lipid Peroxidation Stimulated by ADP-Fe2+ in Rat Liver Microsomes, Biochem. J. 208, 129–140.

    PubMed  CAS  Google Scholar 

  17. Benedetti, A.B., Ponpellu, A., Fulceri, R., Romani, A., and Comporti, M. (1986) Detection of 4-Hydroxynonenal and Other Lipid Peroxitation Products in the Liver of Bromobenzene-Poisoned Mice, Biochim. Biophys Acta 876, 658–666.

    PubMed  CAS  Google Scholar 

  18. 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 Peroxidation but Not Covalent Binding Resulting from the Exposure of Rat Liver Fractions to CCl4, Biochem. J. 264, 527–532.

    PubMed  CAS  Google Scholar 

  19. Raguenez-Viotte, G., Dieber-Rotheneler, M., Dadoun, C., Fillastre, J.P., and Esterbauer, H. (1990) Evidence for 4-Hydroxyalkenals in Rat Cortex Peroxidizod by N2-Methyl-9-hydroxyel-lipticinium Acetate or Celiptium, Biochim. Biophys. Acta 1046, 294–300.

    PubMed  CAS  Google Scholar 

  20. 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 

  21. Dratz, E.A., Farnsworth, C.C., 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. NY Acad. Sci. 570, 46–60.

    PubMed  CAS  Google Scholar 

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

    PubMed  CAS  Google Scholar 

  23. Struhmaier, H., Hinghofer-Szalkay, H., and Schaur, R.J. (1995) Detection of 4-Hydroxynonenal (HNE) as a Physiological Component in Human Plasma, J. Lipid Med. Cell Sign. 11, 51–61.

    Article  Google Scholar 

  24. Novotny, M.V., Yancey, M.F., Stuart, R., Wiesler, D., and Peterson, R.G. (1994) Inhibition of Glycolytic Enzymes by Endogenous Aldehydes: A Possible Relation to Diabetic Neuropathies. Biochim. Biophys. Acta 1226, 145–150.

    PubMed  CAS  Google Scholar 

  25. Kosugi, H., Kojima, T., and Kikugawa, K. (1993) Characteristics of the Thiobarbituric Acid Reactivity of Human Urine as a Possible Consequences of Lipid Peroxidation, Lipids 28, 337–343.

    PubMed  CAS  Google Scholar 

  26. Mahmoodi, H., Hadley, M., Chang, Y.X., and Draper, H.H. (1995) Increased Formation and Degradation of Malondialdehyde-Modified Proteins Under Conditions of Peroxidative Stress, Lipids 30, 963–966.

    PubMed  CAS  Google Scholar 

  27. 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 

  28. American Institute of Nutrition (1980) Second Report of the Ad Hoe Committee on Standards for Nutritional Studies, J. Nutr. 110, 1726.

    Google Scholar 

  29. Lee, H.S., and Csallan, A.S. (1987) Measurement of Free and Bound Malondialdehyde in Vitamin E-Deficient and-Supplemented Rat Liver Tissues, Lipids 22, 104–107.

    PubMed  CAS  Google Scholar 

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

    Google Scholar 

  31. Teare, J.P., Greenfield, S.M., Watson, D., Punchard, N.A., Miller, N., Rice-Evans, C.A., and Thompson, R.P. (1994) Lipid Peroxidation in Rats Chronically Fed Ethanol, Gut 351, 644–647.

    Google Scholar 

  32. Kosugi, H., Kojima, T., and Kikugawa, K. (1993) Characteristies of the Thiobarbituric Acid Reactivity of Human Urine as a Possible Consequence of Lipid Peroxidation, Lipids 28, 337–343.

    PubMed  CAS  Google Scholar 

  33. Kanazaw, K., Kanazaw, E., and Natake, M. (1985) Uptake of Secondary Autooxidation Products of Linoleic Acid by the Rat, Lipids 20, 412–419.

    Google Scholar 

  34. Alary, J., Bravais, F., Craveddi, J., Debrauware, L., Rao, D., and Bories, 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 

  35. Bruenner, B.A., Jones, D., and German, J.B. (1995) Direct Characterization of Protein Adducts of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal Using Electrospray Mass Spectrometry, Chem. Res. Toxicol. 8, 352–359.

    Article  Google Scholar 

  36. Uchida, K., and Stadtman, E.R. (1992) Modification of Histidine Residnes in Proteins by Reaction with 4-Hydroxynonenal. Biochemistry 89, 4544–4548.

    CAS  Google Scholar 

  37. Szweda, L.L., Uchida, K., Tsai, L., and Stadtman, E.R. (1993) Inactivation of Glucose-6-phosphate Dehydrogenase by 4-Hydroxy-2-nonenal, J. Biol. Chem. 268, 3342–3347.

    PubMed  CAS  Google Scholar 

  38. Pryor, W.A., and Porter, N.A. (1990) Suggested Mechanisms for the Production of 4-Hydroxy-2-monenal from the Autoxidation of Polyunsaturated Fatty Acids, Free Radical Biol. Med. 8, 541–543.

    Article  CAS  Google Scholar 

  39. Van Kuijk, F.J.G.M., Holte, L.L., and Dratz, E.A. (1990) 4-Hydroxyhexenal: A Lipid Peroxidation Product Derived from Oxidized Docosahexaenoic Acid, Biochim. Biophys. Acta 1043, 116–118.

    PubMed  Google Scholar 

  40. Benedetti, A., Comporti, M., and Esterbauer, H. (1980) Identification of 4-Hydroxynonenal as a Cytotoxic Product Originating from the Peroxidation of Liver Microsomal Lipid, Biochim. Biophys. Acta 620, 281–296.

    PubMed  CAS  Google Scholar 

  41. Yoshino, K., Matsuura, T., Sano, M., Saito, S.L., and Tomita, I. (1986) Fluorometric Liquid Chromatographic Determination of Aliphatic Aldehydes Arising from Lipid Peroxides, Chem. Pharm. Bull. 34, 1694–1700.

    PubMed  CAS  Google Scholar 

  42. Yoshino, K., Sano, M., Fujita, M., and Tomita, I. (1991) Produetion of Aliphatic Aldehydes on Peroxidation of Various Types of Lipids, Chem. Pharm. Bull. 39, 1788–1791.

    PubMed  CAS  Google Scholar 

  43. Esterbauer, H. (1982) Aldehydic Products of Lipid Peroxidation, in Free Radicals. Lipid Peroxidation and Cancer (MacBrient, D.C.H., and Slater, T.F., eds.) pp. 101–128, Academic Press, New York.

    Google Scholar 

  44. Loidl-Stahlhofen, A., and Spiteller, G. (1994) α-Hydroxyaldehydes, Products of Lipid Peroxidion, Biochim. Biophys. Acta 1211, 156–160.

    PubMed  CAS  Google Scholar 

  45. Kaneko, T., Honda, S., Nakano, S.I., and Matsuo, M. (1987) Lethal Effects of a Linoleic Acid Hydroperoxide and Its Autoxidation Products, Unsaturated Aliphatic Aldehydes, on Human Diploid Fibroblasts, Chem. Biol. Interact 63, 127–137.

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

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

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

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  1. Song-Suk Kim
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  2. Daniel D. Gallaher
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  3. A. Saari Csallany
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Correspondence to A. Saari Csallany.

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Kim, SS., Gallaher, D.D. & Csallany, A.S. Lipophilic aldehydes and related carbonyl compounds in rat and human urine. Lipids 34, 489–496 (1999). https://doi.org/10.1007/s11745-999-0389-1

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  • DOI: https://doi.org/10.1007/s11745-999-0389-1

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