Abstract
Butteroil samples bleached with benzoyl peroxide (BP) and 17 commercial cheeses were screened for oxidized sterols by thin layer chromatography (TLC). Ungrated cheeses made from bleached milk and freshly bleached butteroil contained no detectable oxidized sterols. Oxidized sterols were detected in stored, bleached butteroils and in grated cheeses. Four major oxidation products were the isomeric 5,6-epoxycholesterols and the epimeric 7-hydroxycholesterols identified by TLC, high performance liquid chromatography (HPLC) and mass spectrometry (MS). Additional sterol oxides (tentatively identified and not quantified) present in these samples included low levels of 7-ketocholesterol and cholesta-3,5-dien-7-one. The epimeric 7-hydroxycholesterols were detected in bleached butteroils stored in air (BP-A) and nitrogen (BP-N) for 22 days at 15 C. Butteroil, after 90 days of storage at 15 C, had 30 (BP-N) and 60 (BP-A) µg total oxides/g of bleached oil and, after 1-year at −20 C, had 70 (BP-N) and 180 (BP-A) µg/g butteroil. A grated, unbleached cheese packaged in clear glass contained the most oxidized sterols (44 µg/g). Sterol oxides were not detected in bleached cream using a simulated industrial process.
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References
Ansari, G.A.S., R.D. Walker, V.B. Smart and L.L. Smith, Food Chem. Toxicol. 20:35 (1982).
Imai, H., N.T. Werthessen, P.W. Subramanyam, P.W. LeQuesne and A.H. Soloway, Science 207:651 (1980).
Baranowski, A., C.W.M. Adams, O.M. Bayliss High and D.B. Bower, Atherosclerosis 41:255 (1982).
Blackburn, G.M., A. Rashid and M.H. Thompson, J. Chem. Soc. Chem. Commun. 420 (1979).
Chen, H.W., A.A. Kandutsch and C. Waymouth, Nature 251:419 (1974).
Peng, S.-K., P. Tham, C.B. Taylor and B. Mikkelson, Am. J. Clin. Nutr. 32:1033 (1979).
Smith, L.L., in Cholesterol Autoxidation, Plenum Press, New York, 1981.
Korycka-Dahl, M.E., and T. Richardson, CRC Crit. Rev. Food Sci. Nutr. 10:209 (1978).
Aringer, L., and P. Eneroth, J. Lipid Res. 15:389 (1974).
Smith, L.L., V.B. Smart and G.A.S. Ansari, Mutat. Res. 68:23 (1979).
Leduc, E.H., Brown Univ., Providence, RI (1980).
Parsons, P.G., and P. Goss, Aust. J. Exp. Biol. Med. Sci. 56:287 (1978).
Finocchiaro, E.T., and T. Richardson, J. Food Prot. 46:917 (1983).
Chicoye, E., W.D. Powrie and O. Fennema, J. Food Sci. 33:581 (1968).
Tsai, L.S., K. Ijichi, C.A. Hudson and J.J. Meehan, Lipids 15:124 (1980).
Slaga, T.J., A.J.P. Klein-Szanto, L.L. Triplett, L.P. Yotti and J.E. Troski, Science 213:1023 (1981).
Food and Drug Administration, U.S. Dept. of Health, Education and Welfare, CFR Title 21, Chapter 1, part 133 and part 137, 1982.
Sharratt, M., A.C. Frazer and O.C. Forbes, Food. Cosmet. Toxicol. 2:527 (1964).
Walker, R.O., ed., Offical and Tentative Methods of the American Oil Chemists’ Society, 34th ed., American Oil Chemists’ Society, Champaign, IL, 1978.
Bianco, L.J., G.H. Richardson, J.W. Sherbon, J.A. Burke, W. Roth, D.A. Biggs, R. Ginn and D. Liden, in Standard Methods for the Examination of Dairy Products, 14th ed., edited by E.H. Marth, American Public Health Assoc., Washington, DC, 1978, p. 238.
Stine, C.M., and S. Patton, J. Dairy Sci. 35:655 (1952).
Bligh, E.G., and W.J. Dyer, Can. J. Biochem. Physiol. 37:911 (1959).
Fieser, L.F., and M. Fieser, in Reagents for Organic Synthesis, Vol. 1, John Wiley and Sons, New York, 1967, p. 136.
Smith, L.L., W.S. Matthews, J.C. Price, R.C. Bachman and B. Reynolds, J. Chromatog. 27:188 (1967).
Daly, G.G., E.T. Finocchiaro and T. Richardson, J. Ag. Food Chem. 31:46 (1983).
Bajaj, K.L., and K.L. Ahuja, J. Chromatog. 172:417 (1979).
Ganshirt, H., in Thin Layer Chromatography, edited by E. Stahl, Springer Verlag, New York, 1965, p. 44.
Ansari, G.A.S., and L.L. Smith, J. Chromatog. 175:307 (1979).
Timms, R.E., P. Roupas and W.P. Rogers, Aust. J. Dairy Tech. 37:39 (1982).
Washam, C.J., G.W. Reinbold and E.R. Vedamuthu, J. Milk Food Technol. 37:244 (1974).
Chang, J.E., E.G. Hammond and G.W. Reinhold, J. Dairy Sci. 60:40 (1977).
Richardson, T. and M. Korucka-Dahl, in Developments in Dairy Chemistry, Vol. 2, edited by P.F. Fox, Applied Sci. Publ. Ltd., London, 1983, p. 346.
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Finocchiaro, E.T., Lee, K. & Richardson, T. Identification and quantification of cholesterol oxides in grated cheese and bleached butteroil. J Am Oil Chem Soc 61, 877–883 (1984). https://doi.org/10.1007/BF02542155
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DOI: https://doi.org/10.1007/BF02542155