Abstract
γ-Irradiation of cholesterol in multilamellar vesicles (MLV) at 0–4°C causes oxidation of the A-ring. Two A-ring oxides formed in considerable amounts are cholest-4-en-3-one (10) and cholest-4-ene-3,6-dione (12) in addition to the usual B-ring oxides. Lesser amounts of cholesta-4,6-dien-3-one (11) are also generated. Compounds 10 and 12 were detected and measured in cholesterol irradiated at less than 0.5 kGy in liposomes containing saturated or unsaturated phospholipids. Lesser amounts of 10 and 12, as well as lesser amounts of other cholesterol oxides, were formed when a major constituent of the MLV was dilinoleoylphosphatidylcholine. Autoxidation of cholesterol in MLV also gave rise to small amounts of 10, 11 and 12.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Maerker, G., and K.C. Jones,Lipids 26:139 (1991).
Maerker, G., and K.C. Jones,J. Am. Oil Chem. Soc. 69:451 (1992).
Smith, L.L., inCholesterol Autoxidation, Plenum Press, New York, 1981.
Smith, L.L., and G.A.S. Ansari,J. Chromatogr. 175:307 (1979).
Korahani, V., J. Bascoul and A Crastes de Paulet, Ibid.:392 (1981).
Parish, E.J., H. Honda, S. Chitrakorn and P. Livant,Lipids 26:675 (1991).
Ansari, G.A.S., and L.L. Smith,Chem. Phys. Lipids. 22:55 (1978).
Owen, R.W., A.N. Mason and R.F. Bilton,J. Lipid Res. 24:1500 (1983).
Xiansheng, W., T.V. Hung, P.G. Drew and K. Versteeg,Austral. J. Dairy Techn. 45:50 (1990).
Smith, M., C. Sullivan and N. Goodman,J. Agric. Food Chem. 39:2158 (1991).
Brooks, C.J., W.J. Cole, T.D. Lawrie, J. Maclachlan, J.H. Borthwick and G.M. Barrett,J. Steroid Biochem. 19:189 (1983).
Smith, L.L.,Chem. Phys. Lipids 44:87 (1987).
Maerker, G.,J. Am. Oil Chem. Soc. 64:388 (1987).
Amer, M.A., Abstract, Ibid.:452 (1986).
Cleveland, M.Z., and N.D. Harris,J. Food Protection 50:867 (1987).
Lee, M.L., F.Y. Yang and K.D. Bartle, inOpen Tubular Column Chromatography. Theory and Practice, John Wiley & Sons, New York, 1984, p. 222.
Starka, L., J. Tallova and K. Motlik,Endocrinol. Exp. 15:191 (1981).
Kutryk, M.J.B., T.G. Maddaford, B. Ramjiawan and G.N. Pierce,Circ. Res. 68:18 (1991).
Liu, K., B. Ramjiawan, M.J.B. Kutryk and G.N. Pierce,Mol. Cell Biochem. 108:49 (1991).
Moriarity, N.J., and G. Maerker,J. Am. Oil Chem. Soc. 67:923 (1990).
Pryor, W.A., inFree Radicals in Biology, Vol. I., edited by William A. Pryor, Academic Press, New York, 1976.
Korahani, V., J. Bascoul and A. Crastes de Paulet,Lipids 17:703 (1982).
Chatterjee, S.N., and S. Agarwal,Free Radical Biol. Med. 4:51 (1988).
Barclay, L.R.C., S.J. Locke, J.M. MacNeil, J. van Kessel, G.W. Burton and K.U. Ingold,J. Am. Chem. Soc. 106:2479 (1984).
von Sonntag, C., and H.-P. Schuchmann,Angew. Chem., Int. Ed. Engl. 30:1229 (1991).
O’Connel, J.J., and A. Garner,Int. J. Radiat. Biol. 44:615 (1983).
Terao, J., K. Sugino and S. Matsushita,J. Nutr. Sci. Vitaminol. 31:499 (1985).
Lijana, R.C., M.S. McCracken and C.J. Rudolph,Biochem. Biophys. Acta 879:247 (1986).
Muto, T.J. Tanaka, T. Miura and M. Kimura,Chem. Pharm. Bull. (Tokyo) 27:499 (1985).
Kimura, M., Y. Jin and T. Sawaya, Ibid.:710 (1979).
Author information
Authors and Affiliations
About this article
Cite this article
Maerker, G., Jones, K.C. A-ring oxidation products from γ-irradiation of cholesterol in liposomes. J Am Oil Chem Soc 70, 255–259 (1993). https://doi.org/10.1007/BF02545305
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02545305