Skip to main content
SpringerLink
Log in

Hydroperoxides of erythrocyte phospholipid molecular species formed by lipoxygenase correlate with α-tocopherol levels

  • Article
  • Published:
Lipids

Abstract

The hydroperoxides corresponding to the main molecular species of phosphatidylcholine (PC) and phosphatidylethanolamine (PE) where determined after lipoxygenase treatment of erythrocyte membranes from healthy children. This work was a preliminary study prior to applying this analytical procedure to erythrocyte membranes from children with diseases associated with vitamin E deficiency. The total molecular species corresponding to 20:4 and 22:6 associated with 16:0 and 18:0 were significantly higher in PE (26.94±4.70 nmol/mg protein) than in PC (20.14±6.70 nmol/mg protein); these concentrations represented 63% of the total molecular species in PE and 22% in PC. However, the concentrations of hydroperoxides produced from these polyunsaturated fatty acid molecular species were in the same order of magnitude in PC (3.98±1.56 nmol/mg protein) and in PE (3.61±1.63 nmol/mg protein). In contrast, the molecular species concentrations containing two double bounds, such as 16:0/18:2 and 18:0/18:2 and their corresponding hydroperoxides, were clearly more elevated in PC than in PE. There was a positive relationship between the concentrations of α-tocopherol and each hydroperoxide of PC and PE, and this association was particularly strong in PE (P≤0.0001). These results suggest that α-tocopherol exerts a stabilizing effect toward hydroperoxides, limiting their further degradation into peroxyl radicals. The protective effect of α-tocopherol could be more effective in PE because more polyunsaturated fatty acids were present.

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

GLC:

gas-liquid chromatography

GPx:

glutathione peroxidase

15-HPETE:

15-hydroperoxyeicosatetraenoic acid

HPLC:

high-performance liquid chromatography

PC:

phosphatidylcholine

PE:

phosphatidyl-ethanolamine

16:0/18:2 PC:

1-palmitoyl-2-linoleoyl-sn-glycero-3-PC

16:0/20:4 PC:

1-palmitoyl-2-arachidonoyl-sn-glycero-3-PC

16:0/22:6 PC:

1-palmitoyl-2-docosahexaenoyl-sn-glycero-3-PC

18:0/18:2 PC:

1-stearoyl-2-linoleoyl-sn-glycero-3-PC

18:0/22:6 PC:

1-stearoyl-2-arachidonoyl-sn-glycero-3-PC

16:0/18:2 PE:

1-palmitoyl-2-linoleoyl-sn-glycero-3-PE

16:0/20:4 PE:

1-palmitoyl-2-arachidonoyl-sn-glycero-3-PE

16:0/22:6 PE:

1-palmitoyl-2-docosahexaenoyl-sn-glycero-3-PE

18:0/18:2 PE:

1-stearoyl-2-linoleoyl-sn-glycero-3-PE

18:0/20:4 PE:

1-stearoyl-2-arachidonoyl-sn-glycero-3-PE

18:0/22:6 PE:

1-stearoyl-2-docosahexaenoyl-sn-glycero-3-PE

PUFA:

polyunsaturated fatty acids

TBARS:

thiobarbituric acid reactive substances

UV:

ultraviolet

References

  1. Clemens, M.R., and Waller, H.D. (1987) Lipid Peroxidation in Erythrocytes,Chem. Phys. Lipids 45, 251–268.

    Article  PubMed  CAS  Google Scholar 

  2. Brash, A.R., Ingram, C.D., and Harris, T.M. (1987) Analysis of a Specific Oxygenation Reaction of Soybean Lipoxygenase-1 with Fatty Acids Esterified in Phospholipids,Biochemistry 26, 5465–5471.

    Article  PubMed  CAS  Google Scholar 

  3. Janero, D., and Burghardt, B. (1988) Analysis of Cardiac Membrane Phospholipid Peroxidation Kinetics as Malondialdehyde: Nonspecificity of Thiobarbituric Acid-Reactivity,Lipids 23, 452–458.

    PubMed  CAS  Google Scholar 

  4. Kosogi, T., Kojima, T., and Kikugawa, K. (1989) Thiobarbituric Acid-Reactive Substances from Peroxidized Lipids,Lipids 24, 873–881.

    Google Scholar 

  5. Therond, P., Couturier, M., Demelier, J.F., and Lemonnier, F. (1993) Simultaneous Determination of the Main Molecular Species of Soybean Phosphatidylcholine or Phosphatidyl-ethanolamine and their Corresponding Hydroperoxides Obtained by Lipoxygenase Treatment,Lipids 28, 245–249.

    PubMed  CAS  Google Scholar 

  6. Burton, G.W., Ingold, K.U., and Thompson, K.E. (1981) An Improved Procedure for Isolation of Ghost Membranes from Human Red Blood Cells,Lipids 16, 946.

    PubMed  CAS  Google Scholar 

  7. Hamilton, J.G., and Comai, K. (1988) Rapid Separation of Neutral Lipids, Free Fatty Acids and Polar Lipids Using Prepacked Silica Sep-Pak Columns,Lipids 23, 1146–1149.

    PubMed  CAS  Google Scholar 

  8. Yamamoto, Y., Brodsky, M.H., Baker, J.C., and Ames, B.N. (1987) Detection and Characterization of Lipid Hydroperoxides at Picomole Levels by High-Performance Liquid Chromatography,Anal. Biochem. 160, 7–13.

    Article  PubMed  CAS  Google Scholar 

  9. Zaspel, B.J., and Csallany, A.S. (1983) Determination of Alpha-Tocopherol in Tissues and Plasma by High-Performance Liquid Chromatography,Anal. Biochem. 130, 146–150.

    Article  PubMed  CAS  Google Scholar 

  10. Paglia, D.E., and Valentine, W.N. (1967) Studies on the Qualitative Characterization of Erythrocyte Glutathione Peroxidase,J. Lab. Clin. Med. 70, 158–169.

    PubMed  CAS  Google Scholar 

  11. Therasse, J., and Lemonnier, F. (1987) Determination of Plasma Lipoperoxides by High-Performance Liquid Chromatography,J. Chromatogr. 413, 237–241.

    PubMed  CAS  Google Scholar 

  12. Miyazawa, T. (1989) Determination of Phospholipid Hydroperoxides in Human Blood Plasma by a Chemiluminescence-HPLC Assay,Free Radic. Biol. Med. 7, 209–217.

    Article  PubMed  CAS  Google Scholar 

  13. Akasaka, K., Ohata, A., Ohrui, H., and Meguro H. (1995) Automatic Determination of Hydroperoxides of Phosphatidylcholine and Phosphatidylethanolamine in Human Plasma,J. Chromatogr. 665, 37–43.

    CAS  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  15. Maiorino, M., Coassin, M., Roveri, A., and Ursini F. (1989) Microsomal Lipid Peroxidation: Effect of Vitamin E and Its Functional Interaction with Phospholipid Hydroperoxide Glutathione Peroxidase,Lipids 24, 721–726.

    PubMed  CAS  Google Scholar 

  16. Guo, L., Ogamo, A., Ou, Z., Shinozuka, T., and Nakagawa, Y. (1995) Preferential Formation of the Hydroperoxide of Linoleic Acid in Choline Glycerophospholipids in Human Erythrocytes Membrane During Peroxidation with an Azo Initiator,Free Radic. Biol. Med. 18, 1003–1012.

    Article  PubMed  CAS  Google Scholar 

  17. Jordan, R.A., and Schenkman, J.B. (1982) Relationship Between Malondialdehyde Production and Arachidonate Consumption During NADPH-Supported Microsomal Lipid Peroxidation,Biochem. Pharmacol. 31, 1393–1400.

    Article  PubMed  CAS  Google Scholar 

  18. Kagan, V.E. (ed.) (1988) The Role of LPO in Normal Physiological Processes, inLipid Peroxidation in Biomembranes, pp. 147–175, CRC Press, Boca Raton.

    Google Scholar 

  19. Peers, K.E., Coxon, D.T., and Chan, H.W.-S. (1981) Autoxidation of Methyl Linoleate: The Effect of α-Tocopherol,J. Sci. Food Agric. 32, 898–904.

    Article  CAS  Google Scholar 

  20. Miyashita, K., Hara, N., Fujimoto, K., and Kaneda, T. (1985) Dimers Formed in Oxygenated Methyl Linoleate,Lipids 20 578–587.

    CAS  Google Scholar 

  21. Maiorino, M., Gregolin, C., and Ursini, F. (1990) Phospholipid Hydroperoxide Glutathione Peroxidase, inMethods in Enzymology (Packer, L., ed.) Vol. 186, pp. 448–457, Academic Press, San Diego.

    Google Scholar 

  22. Grossman, S., and Waksman, E.G. (1984) New Aspects of the Inhibition of Soybean Lipoxygenase by α-Tocopherol, Evidence for the Existence of a Specific Complex,Int. J. Biochem. 16, 281–289.

    Article  PubMed  CAS  Google Scholar 

  23. Lomnitski, L., Bar-Natan, R., Sklan, D., and Grossman, S. (1993) The Interaction Between β-Carotene and Lipoxygenase in Plant and Animal Systems,Biochim. Biophys. Acta 1167, 331–338.

    PubMed  CAS  Google Scholar 

  24. Arai, H., Nagao, A., Terao, J., Suzuki, T., and Takama K. (1995) Effect ofd-α-Tocopherol Analogues on Lipoxygenase-Dependent Peroxidation of Phospholipid-Bile Salt Micelles,Lipids 30, 135–140.

    PubMed  CAS  Google Scholar 

  25. Buttris, J.L., and Diplock, A.T. (1988) The Relation Between Alpha-Tocopherol and Phospholipid Fatty Acids in Rat Liver Subcellular Membrane Fractions,Biochim. Biophys. Acta 962, 81–90.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. INSERM U 347, Hôpital Bicêtre, 80 rue du Général Leclerc, 94276, Le Kremlin Bicêtre, France

    Patrice Therond, Martine Couturier & Frédérique Lemonnier

  2. Laboratoire de Biochimie, Hôpital R. Debré, 75019, Paris, France

    Jean François Demelier

Authors
  1. Patrice Therond
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Martine Couturier
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jean François Demelier
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Frédérique Lemonnier
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Therond, P., Couturier, M., Demelier, J.F. et al. Hydroperoxides of erythrocyte phospholipid molecular species formed by lipoxygenase correlate with α-tocopherol levels. Lipids 31, 703–708 (1996). https://doi.org/10.1007/BF02522885

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02522885

Keywords

Search

Navigation