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Gamma-irradiation of individual cholesterol oxidation products

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Journal of the American Oil Chemists’ Society

Abstract

Cholesterol and seven of its oxidation products in aqueous suspensions of multilamellar vesicles or sonicated aqueous suspensions were subjected individually to γ-radiation (10 KGy) at 0–4°C in air, N2 or N2O. All compounds underwent some changes under the influence of radiation. β-Epoxide (cholesterol 5β,6β-epoxide) and, to a much lesser extent, α-epoxide (cholesterol 5α,6α-epoxide) were converted in low yield to 6-ketocholestanol (5α-cholestan-3β-ol-6-one). 7β-Hydroxycholesterol (cholest-5-ene-3β,7β-diol) and, to a lesser extent, 7α-hydroxycholesterol (cholest-5-ene-3β,7α-diol) gave low yields of 7-ketocholestanol (5α-cholestan-3β-ol-7-one). The latter compound also was obtained by irradiation of 7-ketocholesterol (cholest-5-ene-3β-ol-7-one). 6-Ketocholestanol and 7-ketocholestanol are potential biomarkers for irradiated meat and poultry.

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References

  1. Smith, L.L., inCholesterol Autoxidation, Plenum Press, New York, 1981.

    Google Scholar 

  2. Kimara, M., Y. Jin and T. Gaways,Chem. Pharm. Bull. (Tokyo) 27:710 (1979).

    Google Scholar 

  3. Muto, T., K. Sugino and S. Matsushita, Ibid.:3172 (1982).

    CAS  Google Scholar 

  4. Terao, J., K. Sugino and S. Matsushita,J. Nutr. Sci. Vitaminol. 31:499 (1985).

    CAS  Google Scholar 

  5. Lijana, R.C., M.S. McCracken and C.J. Rudolph,Biochim. Biophys. Acta 879:247 (1986).

    CAS  Google Scholar 

  6. Ansari, G.A.S., and L.L. Smith,Photochem. Photobiol. 30:147 (1979).

    CAS  Google Scholar 

  7. Kücera, J., V. Schwarz and M. Sykora,J. Radioanal. Nucl. Chem. 87:219 (1984).

    Article  Google Scholar 

  8. Sevanian, A., and L.L. McLeod,Lipids 22:627 (1987).

    CAS  Google Scholar 

  9. Lakritz, L., and G. Maerker,J. Food Sci. 54:1569 (1989).

    Article  CAS  Google Scholar 

  10. Smith, L.L.,Chem. Phys. Lipids 44:87 (1987).

    Article  CAS  Google Scholar 

  11. Maerker, G.,J. Am. Oil Chem. Soc. 64:388 (1987).

    CAS  Google Scholar 

  12. Maerker, G., and K.C. Jones,Lipids 26:139 (1991).

    CAS  Google Scholar 

  13. von Sonntag, C., inThe Chemical Basis of Radiation Biology, Taylor & Francis, Inc., Philadelphia, 1987, pp. 32–34, 37.

    Google Scholar 

  14. Moriarity, N.J., and G. Maerker,J. Am. Oil Chem. Soc. 67:923 (1990).

    CAS  Google Scholar 

  15. Olson, F., C.A. Hurt, F.C. Szoka, W.J. Vail and D. Papahadjopoulos,Biochim. Biophys. Acta 557:9 (1979).

    Article  CAS  Google Scholar 

  16. Lee, M.L., F.Y. Yang and K.D. Bartle, inOpen Tubular Column Gas Chromatography. Theory and Practice, John Wiley & Sons, New York, 1984, p. 222.

    Google Scholar 

  17. Maerker, G., and J. Unruh, Jr.,J. Am. Oil Chem. Soc. 63:767 (1986).

    CAS  Google Scholar 

  18. Maerker, G., and F.J. Bunick, Ibid.:771 (1986).

    CAS  Google Scholar 

  19. Missler, S.R., B.A. Wasilchuck and C. Merritt, Jr.,J. Food Sci. 50:595 (1985).

    Article  CAS  Google Scholar 

  20. Chatterjee, S.N., and S. Agarwal,Free Radical Biol. Med. 4:51 (1988).

    Article  CAS  Google Scholar 

  21. Chapman, D., inLiposome Technology, Vol. I, Preparation of Liposomes, edited by G. Gregoriadis, CRC Press, Inc., Boca Raton, 1984, pp. 1–8.

    Google Scholar 

  22. Szoka, F.C., and D. Papahadjopoulos,Ann. Rev. Biophys. Bioeng. 9:467 (1980).

    Article  CAS  Google Scholar 

  23. Maerker, G., E.H. Nungesser and F.J. Bunick,Lipids 23:761 (1988).

    Article  CAS  Google Scholar 

  24. Churý, J.,Chem. Abstr. 42:7405i (1948).

    Google Scholar 

  25. Higley, N.A., S.L. Taylor, A.M. Herian and K. Lee,Meat Sci. 16:175 (1986).

    Article  CAS  Google Scholar 

  26. Buxton, G.V., inRadiation Chemistry, Principles and Applications, edited by Farhataziz and M.A.J. Rogers, VCH Publishers, Inc., New York, 1987, pp. 332–342.

    Google Scholar 

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Maerker, G., Jones, K.C. Gamma-irradiation of individual cholesterol oxidation products. J Am Oil Chem Soc 69, 451–455 (1992). https://doi.org/10.1007/BF02540947

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  • DOI: https://doi.org/10.1007/BF02540947

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