Degradation Products of L-Tryptophan Reacted with Peroxidizing Methyl Linoleate a,b

  • S. H. Yong
  • S. Lau
  • Y. Hsieh
  • M. Karel


Reactions between L-tryptophan and peroxidizing methyl linoleate in a model system simulating the porous structure of dehydrated foods result in formation of N-formylkynurenine, kynurenine, and diastereomers of dioxindole-3-alanine. A mechanism, consistent with the free-radical pathway for oxidation of polyunsaturated lipids, is proposed for formation of these products from L-tryptophan degradation by peroxidizing lipids.


Methyl Linoleate Cysteic Acid Methionine Sulfoxide Sulfinic Acid Polyunsaturated Lipid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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  1. Ambe, K.S., Kumata, U.S., and Tappel, A.L., 1961, Radiat. Res., 15: 709.Google Scholar
  2. Barker, S.A., Gray, C.J., and Jolley, M.B., 1971, Biocher. Biophys. Res. Commun., 45:654.Google Scholar
  3. Benassi, C.A., Scoffone, E., Galiazzo, G., and lori, G., 1967, Photochem. Photobiol., 6:857.Google Scholar
  4. Chio, P..S., and Tappel, A.L., 1969, Biochemistry, 8: 2827.Google Scholar
  5. Cornforth, J.W., Dalgliesh, C.E., and Neuberger, A., 1951, Biochem. J., 48:598.Google Scholar
  6. Foote, C.S., 1976, in: “Free Radicals in Biology,” vol. 2, W.A. Pryor, ed., Academic Press, New York, p. 85.Google Scholar
  7. Friedman, M., and Finley, J.W., 1975, in: “Protein Nutritional Quality of Foods and Feeds,” Part 1, M. Friedman, ed., Marcel Dekker, Inc., New York, p. 423.Google Scholar
  8. Gurnani, S., Arifuddin, M., and Augusti, K.T., 1966, Photochem. Photobiol., 5:494.Google Scholar
  9. Hazum, E., Fridkin, M., Meidan, R., and Koch, Y., 1977, Eur. J. Biochem., 79:269.Google Scholar
  10. Hinman, R.L., and Bauman, C.P., 1964, J. Org. Chem., 29:2431.Google Scholar
  11. Jarenback, J., and Liljemark, A., 1975, J. Food Technol., 10:437.Google Scholar
  12. Jayson, G.G., Scholes, G., and Weiss, J., 1954, Biochem. J., 57:386.Google Scholar
  13. Kanazawa, K., Danno, G., and Natale, M., 1975, J. Nutr. Sci. Vitaminol., 21:373.Google Scholar
  14. Kanner,.J., and Karel, M., 1976, J. Agr. Food Chem., 24:468.Google Scholar
  15. Karel, M., Shaich, K., and Roy, R.B., 1975, J. Agr. Food Chem., 23: 159.Google Scholar
  16. Karel, M., and Yong, S.H., 1979, in: “Proceedings, Second International Symposium on Properties of Water in Relation to Food Quality and Stability,” Academic Press, New York, in press. Leaver, I.I1., 1978, Photochem. Photobiol., 27:451.Google Scholar
  17. Lundberg, W.O., 1962, in: “Lipids and Their Oxidation,” H.W. Schultz, E.A. Day, and R.O.Sinnhuber, eds., Avi. Publishing Co., Westport, CT, p. 36.Google Scholar
  18. Matsumoto, I., Yoshida, D., Mizusaki, S., and Okamoto, H., 1976, in: “Proceedings of the 5th Annual Meeting of the Environmental Mutagen Society,” Environmental Mutagen Society, Tokyo, Japan, p 6.Google Scholar
  19. O’Brien, P.J., 1966, Biochem. J., 101:12.Google Scholar
  20. Peter, B., and Rajewsky, B., 1963, Z. Naturforsch. 18b:110. Pirie, A., 1971, Biochem. J., 125: 203.Google Scholar
  21. Pokorny, J., Kolakowska, A., El—Zeany, B.A., and Janicek, G., 1975, Z. Lehensm. Unters—Forsch., 157: 323.CrossRefGoogle Scholar
  22. Pokorny, J., and Janicek, G., 1968, Nahrung, 12: 81.Google Scholar
  23. Remers, W.A., 1972, in: “Indoles,” Part 1, W.J. Houlihan, ed., John Wiley & Sons, New York, ch. 1, p. 4.Google Scholar
  24. Roubal, W.T., and Tappel, A.L., 1966, Arch. Biochem. Biophys., 113:5.Google Scholar
  25. Savige, W.E., and Fontana, A., 1976, J. Chem. Soc. (London) Chem. Commun., 1976: 599.CrossRefGoogle Scholar
  26. Venolia, A.W., and Tappel, A.L., 1958, J. Amer. Oil Chem. Soc., 35: 135.Google Scholar
  27. Walrant, P., and Santus, R., 1974, Photochem. Photobiol., 19:411.Google Scholar
  28. Walrant, P., Santus, R., and Grossweiner, L.I., 1975, Photochem. Photobiol., 22:63.Google Scholar
  29. Yong, S.H., 1979, in: “Global Malnutrition and Cereal Fortification,” J.E. Austin, ed., Ballinger Publishing Co., Cambridge, MA, ch. 4, p. 43.Google Scholar
  30. Yong, S.H., and Karel, M., 1978, J. Amer. Oil Chem. Soc., 55: 352.Google Scholar
  31. Yong, S.H., and Karel, M., 1979, J. Food Sei., 44:568.Google Scholar
  32. Yong, S.H., and Lau, S., 1979, J. Chromatogr., 175:343.Google Scholar
  33. Zigman, S., Hare, J.D., Yulo, T., and Ennist, D., 1978, Photochem. Photobiol., 27:281.Google Scholar
  34. Zirlin, A., and Karel, M., 1969, J. Food Sei., 34:160.Google Scholar
  35. Zweig, G., and Sherma, J., 1972, in: “Handbook of Chromatography,” vol. 2, G. Zweig and J. Sherma, eds., CRC Press, Cleveland, OII, p. 107.Google Scholar

Copyright information

© Springer Science+Business Media New York 1980

Authors and Affiliations

  • S. H. Yong
    • 1
    • 2
  • S. Lau
    • 1
  • Y. Hsieh
    • 1
  • M. Karel
    • 1
  1. 1.Department of Nutrition and Food ScienceMassachusetts Institute of TechnologyCambridgeUSA
  2. 2.Pillsbury CompanyMinneapolisUSA

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