Skip to main content
SpringerLink
Log in

Determination of hydroperoxides and structures by high-performance liquid chromatography with post-column detection with diphenyl-1-pyrenylphosphine

  • Method
  • Published:
Lipids

Abstract

A high-performance liquid chromatographic method, using post-column detection with diphenyl-1-pyrenyl-phosphine (DPPP), was developed for the quantitative and qualitative determination of isomeric lipid hydroperoxides (OOH). The OOH eluted from a normal-phase column were passed through a photodiode array detector and then mixed with DPPP solution in a reaction coil heated at 80°C. DPPP oxide formed by the reaction with OOH was determined by monitoring the fluorescence intensity at 380 nm and excitation at 352 nm. The conjugated diene OOH (13-cis, trans- and 9-cis, trans-OOH) and nonconjugated OOH (12-cis-trans- and 10-cis, trans-OOH) from photosensitized oxidation of methyl linoleate were determined in a molar ratio of 31∶29∶19∶21, respectively. However, only the two conjugated hydroperoxides were detected by ultraviolet absorption at 234 nm. Further applications were carried out for the determination of OOH of methyl oleate and methyl linolenate. This method proved to be useful for the determination of the OOH containing both conjugated and nonconjugated diene structures.

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

DPPP:

diphenyl-1-pyrenylphosphine

FAME:

fatty acid methyl ester

GC/MS:

gas chromatography/mass spectrometry

HPLC:

high-performance liquid chromatography

OOH:

hydroperoxide

TMS:

trimethylsilyl

UV:

ultraviolet

References

  1. Chan, H.W.S., and Levett, G. (1977) Autoxidation of Methyl Linoleate. Separation and Analysis of Isomeric Mixtures of Methyl Linoleate Hydroperoxides and Methyl Hydroxylinoleates,Lipids 12, 99–104.

    PubMed  CAS  Google Scholar 

  2. Neff, W.E., Frankel, E.N., and Weisleder, D. (1981) High Pressure Liquid Chromatography of Autoxidized Lipids: II. Hydroperoxy-Cyclic Peroxides and Other Secondary Products from Methyl Linolenate,Lipids 16, 439–448.

    CAS  Google Scholar 

  3. Coxon, D.T., Price, K.R., and Chan, H.W.S. (1981) Formation, Isolation and Structure Determination of Methyl Linolenate Diperoxides,Chem. Phys. Lipids 28, 365–378.

    Article  CAS  Google Scholar 

  4. 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. Chem. 160, 7–13.

    CAS  Google Scholar 

  5. Miyazawa, T., Yasuda, K., and Fujimoto, K. (1987) Chemiluminescence High Performance Liquid Chromatography of Phosphatidylcholine Hydroperoxide,Anal. Lett. 20, 915–925.

    CAS  Google Scholar 

  6. Yamamoto, Y., and Niki, E. (1989) Presence of Cholesteryl Ester Hydroperoxide in Human Blood Plasma,Biochem. Biophys. Res. Commun. 165, 989–993.

    Article  Google Scholar 

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

    Article  PubMed  CAS  Google Scholar 

  8. Miyazawa, T., Suzuki, T., Fujimoto, K., and Yasuda, K. (1992) Chemiluminescent Simultaneous Determination of Phosphatidylcholine Hydroperoxide and Phosphatidylethanolamine Hydroperoxide in the Liver and Brain of the Rat,J. Lipid Res. 33, 1051–1059.

    PubMed  CAS  Google Scholar 

  9. Akaska, K., Suzuki, T., Ohrui, H., and Meguro, H. (1987) Study on Aromatic Phosphines for Novel Fluorometry of Hydroperoxides (II)—The Determination of Lipid Hydroperoxides with Diphenyl-1-Pyrenylphosphine,Anal. Lett. 20, 797–907.

    Google Scholar 

  10. Akasaka, K., Ohrui, H., and Meguro, H. (1993) Determination of Triacylglycerol and Cholesterol Ester Hydroperoxides in Human Plasma by High-Performance Liquid Chromatography with Fluorometric Postcolumn Detection,J. Chromatogr. 617, 205–211.

    PubMed  CAS  Google Scholar 

  11. Akasaka, K., Ohrui, H., and Meguro, H. (1994) Measurement of Cholesterol Hydroperoxides of High and Combined Low and Very Low Lipoprotein in Human Plasma,Biosci. Biotech. Biochem. 58, 396–399.

    CAS  Google Scholar 

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

    Google Scholar 

  13. Neff, W.E., and Frankel, E.N. (1980) Quantitative Analyses of Hydroxystearate Isomers from Hydroperoxides by High Pressure Liquid Chromatography of Autoxidized and Photosensitized-Oxidized Fatty Esters,Lipids 15, 587–590.

    CAS  Google Scholar 

  14. Frnakel, E.N., Neff, W.E., and Bessler, T.R. (1979) Analysis of Autoxidized Fats by Gas Chromatography-Mass Spectrometry: V. Photosensitized Oxidation,Lipids 14, 961–967.

    Google Scholar 

  15. Chan, H.W.S. and Levett, G. (1977) Oxidation of Methyl Oleate: Separation of Isomeric Hydroperoxyoctadecenoates and Methyl Hydroxystearates by High performance Liquid Chromatography,Chem. Ind. (London), 692–693.

  16. Frankel, E.N. (1985) Chemistry of Free Radical and Singlet Oxidation of Lipids,Prog. Lipid Res. 23, 197–221.

    Article  Google Scholar 

  17. Terao, J., and Matsushita, S. (1977) Geometric Isomers of Monohydroperoxides Formed by Autoxidation of Methyl Linoleate,Agric. Biol. Chem. 41, 2401–2405.

    CAS  Google Scholar 

  18. Kondo, Y., Kawai, Y., Miyazawa, T., and Mizutani, J. (1993) Chemiluminescence-HPLC Analysis of Fatty Acid Hydroperoxide Isomers,Biosci. Biotech. Biochem. 57, 1575–1576.

    Article  CAS  Google Scholar 

  19. Toyoda, I., Terao, J., and Matsushita, S. (1982) Hydroperoxides Formed by Ferrous Ion-Catalyzed Oxidation of Methyl Linolenate,Lipids 17, 84–90.

    CAS  Google Scholar 

  20. Yamauchi, R., Yamada, T., Kato, K., and Ueno, Y. (1983) Monohydroperoxides Formed by Autoxidation and Photosensitized Oxidation of Methyl Eicosapentaenoate,Agric. Biol. Chem. 47, 2897–2902.

    CAS  Google Scholar 

  21. VanRollins, M., and Murphy, R.C. (1984) Autoxidation of Docosahexaenoic Acid: Analysis of Ten Isomers of Hydroxydocosahexaenoate,J. Lipid Res. 25, 507–517.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Applied Chemistry and Microbiology, University of Helsinki, FIN-00014, Finland

    Anu Hopia

  2. Department of Food Science and Technology, University of California, 95616, Davis, California

    J. Bruce German & Edwin N. Frankel

  3. Department of Food Science and Technology, Tokyo University of Fisheries, Konan 4, Minato-ku, 108, Tokyo, Japan

    Toshiaki Ohshima

Authors
  1. Toshiaki Ohshima
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anu Hopia
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. Bruce German
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Edwin N. Frankel
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Ohshima, T., Hopia, A., German, J.B. et al. Determination of hydroperoxides and structures by high-performance liquid chromatography with post-column detection with diphenyl-1-pyrenylphosphine. Lipids 31, 1091–1096 (1996). https://doi.org/10.1007/BF02522467

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02522467

Keywords

Search

Navigation