Studies of the fluorescent products of lipid oxidation in aqueous emulsion with glycine and on the surface of silica gel

  • Hiroyuki Shimasaki
  • O. S. Privett
  • Ichiro Hara

Abstract and Summary

The formation of fluorescent products in the reaction of methyl linoleate hydroperoxide with glycine in aqueous emulsions correlated directly with the decrease in diene conjugation and the increase in thiobarbituric acid (TBA) reactive substances. These correlations also were reflected in the course of the oxidation of methyl linoleate in aqueous emulsions with glycine and indicated that glycine reacted with products of peroxide decomposition as opposed to intermediates of autoxidation in hydroperoxide formation. Thin layer chromatography (TLC) and selective solvent extraction demonstrated that the products of the reaction contained many substances with a fluorescent spectrum similar to those of lipofuscin pigments. When methyl esters of polyunsaturated fatty acids or other polyunsaturated lipids underwent oxidation adsorbed on silica gel particles, products with similar fluorescent spectral properties were formed illustrating that fluorescent substances were formed in a variety of reactions associated with the oxidation of unsaturated lipids.


Methyl Linoleate Diene Conjugation Fluorescent Product Fluorescent Substance Quinine Sulfate 
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  1. 1.
    Packer, L., D.W. Deamer, and R.L. Heath, Adv. Gerontol. Res. 2:77 (1967).Google Scholar
  2. 2.
    Siakotos, A.N., H.H. Goebel, V. Patel, I. Watanabe, and W. Zeman in “Advances in Experimental Medicine and Biology,” Edited by B.W. Volk and S.M. Aronson, Plenum Press, New York, NY, 1970, p. 53.Google Scholar
  3. 3.
    Tappel, A.L., in “Pathological Aspects of Cell Membranes,” Vol. 1, Edited by B.F. Trumps and A. Arstilla, Academic Press, New York, NY, 1975, p. 145.Google Scholar
  4. 4.
    Tappel, A.L., B. Fletcher, and D. Deamer, J. Gerontol. 28:415 (1973).Google Scholar
  5. 5.
    Porta, E.A., and W.S. Hartroft, in “Pigments in Pathology,” Edited by M. Wolman, Academic Press, New York, NY, 1969, p. 191.Google Scholar
  6. 6.
    Granados, H., K.E. Mason, and H. Dam, Acta Pathol. Microbiol. Scand. 24:86 (1947).Google Scholar
  7. 7.
    Hartroft, W.S., and E.A. Porta, CRC Crit. Rev. Toxicol. 1:379 (1972).CrossRefGoogle Scholar
  8. 8.
    Trombly, R., A.L. Tappel, J.G. Coniglio, W.M. Grogan, Jr., and R.K. Rhamy, Lipids 10:591 (1975).CrossRefGoogle Scholar
  9. 9.
    Hendley, D.D., A.S. Mildvan, M.C. Reporter, and B.L. Strehler, J. Gerontol. 18:144 (1963).Google Scholar
  10. 10.
    Fletcher, B.L., C.J. Dillard, and A.L. Tappel, Anal. Biochem. 52:1 (1973).CrossRefGoogle Scholar
  11. 11.
    Chio, K.S., U. Reiss, B. Fletcher, and A.L. Tappel, Science 166:1535 (1969).CrossRefGoogle Scholar
  12. 12.
    Dillard, C.J., and A.L. Tappel, Lipids 6:715 (1971).CrossRefGoogle Scholar
  13. 13.
    Adhikari, H.R., and A.L. Tappel, Radiat. Res. 61:177 (1975).CrossRefGoogle Scholar
  14. 14.
    Chio, K.S., and A.L. Tappel, Biochemistry 8:2821 (1969).CrossRefGoogle Scholar
  15. 15.
    Dillard, C.J., and A.L. Tappel, Lipids 8:183 (1973).CrossRefGoogle Scholar
  16. 16.
    Malshet, V.G., and A.L. Tappel, Ibid. 8:194 (1973).CrossRefGoogle Scholar
  17. 17.
    Slawson, V., A.W. Adamson, and J.R. Mead, Ibid. 8:129 (1973).CrossRefGoogle Scholar
  18. 18.
    Porter, W.L., L.A. Levasseur, and A.S. Henick, Ibid. 7:699 (1972).CrossRefGoogle Scholar
  19. 19.
    Honn, F.J., I.I. Bezman, and B.F. Daubert, JAOCS 28:129 (1951).CrossRefGoogle Scholar
  20. 20.
    Weis, L.D., T.R. Evans, and P.A. Leermakers, Ibid. 90:6109 (1968).CrossRefGoogle Scholar
  21. 21.
    Privett, O.S., W.O. Lundberg, and C.E. Nickell, Ibid. 30:17 (1953).Google Scholar
  22. 22.
    Corliss, G.A., and L.R. Dugan, Lipids 5:846 (1970).CrossRefGoogle Scholar
  23. 23.
    Wilbur, K.M., F. Bernheim, and O.W. Shapiro, Arch. Biochem. Biophys. 24:305 (1949).Google Scholar
  24. 24.
    Privett, O.S., K.A. Dougherty, and J.D. Castell, Am. J. Clin. Nutr. 24:1265 (1971).Google Scholar
  25. 25.
    Privett, O.S., M.L. Blank, and B. Verdino, J. Nutr. 85:187 (1965).Google Scholar
  26. 26.
    Malshet, V.G., A.L. Tappel, and V.M. Burns, Lipids 9:328 (1974).CrossRefGoogle Scholar
  27. 27.
    Buttkus, H., and R.J. Bose, JAOCS 49:440 (1972).CrossRefGoogle Scholar
  28. 28.
    Buttkus, H.A., J. Agr. Food Chem. 23:823 (1975).CrossRefGoogle Scholar
  29. 29.
    Trombly, R., and A.L. Tappel, Lipids 10:441 (1975).CrossRefGoogle Scholar
  30. 30.
    Taubold, R.D., A.N. Siakotos, and E.G. Perkins, Ibid. 10:383 (1975).CrossRefGoogle Scholar
  31. 31.
    Shanfield, H., F. Hsu, and A.J.P. Martin, J. Chromatogr. 126:457 (1976).CrossRefGoogle Scholar
  32. 32.
    Segura, R., and A.M. Gotto, J. Chromatogr. 99:643 (1974).CrossRefGoogle Scholar
  33. 33.
    Reddy, K., B. Flecher, A. Tappel, and A.L. Tappel, J. Nutr. 103:908 (1973).Google Scholar

Copyright information

© The American Oil Chemists’ Society 1977

Authors and Affiliations

  • Hiroyuki Shimasaki
    • 1
  • O. S. Privett
    • 1
  • Ichiro Hara
    • 2
  1. 1.The Hormel InstituteUniversity of MinnesotaAustin
  2. 2.Department of Serology, Faculty of MedicineUniversity of TokyoTokyoJapan

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