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The major cholesterol oxidation products identified were 7\u2010keto\u2010cholesterol, isomeric cholesterol 5,6\u2010epoxides, isomeric 7\u2010hydroperoxides and isomeric 3,7\u2010cholestane diols. Other commonly encountered products included 3,5\u2010cholestadiene\u20107\u2010one and cholestane\u20103\u03b2,5\u03b1,6\u03b2\u2010triol. Superoxide\u2010dependent peroxidation required iron and produced a gradual increase in 7\u2010keto\u2010cholesterol and cholesterol epoxides. Cholesterol oxidation was greatest in liposomes containing high proportions of unsaturated phospholipid to cholesterol (4\u22361 molar ratio), intermediate with low phospholipid to cholesterol ratios (2\u22361) and least in liposomes prepared with dipalmitoylphosphatidylcholine and cholesterol. This relationship held regardless of the oxidizing conditions used. Cumene hydroperoxide\u2010dependent lipid peroxidation and\/or more prolonge oxidations with other oxidizing systems yielded a variety of products where cholesterol\u20105\u03b2,6\u03b2\u2010epoxide, 7\u2010ketocholesterol and the 7\u2010hydroperoxides were most consistently elevated. Oxyradical initiation of lipid peroxidation produced a pattern of cholesterol oxidation products distinguishable from the pattern derived by cumene hydroperoxide\u2010dependent peroxidation. Our findings indicate that cholesterol autoxidation in biological membranes is modeled by the peroxide\u2010induced oxidation of liposomes bearing unsaturated fatty acids and suggest that a number of cholesterol oxidation products are derived from peroxide\u2010dependent propagation reactions occurring in biomembranes.<\/jats:p>","DOI":"10.1007\/bf02533940","type":"journal-article","created":{"date-parts":[[2007,1,4]],"date-time":"2007-01-04T18:42:25Z","timestamp":1167936145000},"page":"627-636","source":"Crossref","is-referenced-by-count":104,"title":["Cholesterol autoxidation in phospholipid membrane bilayers"],"prefix":"10.1002","volume":"22","author":[{"given":"Alex","family":"Sevanian","sequence":"first","affiliation":[{"name":"Institute for Toxicology University of Southern California, School of Pharmacy Los Angeles California 90033"},{"name":"Department of Pathology University of Southern California, School of Pharmacy 1985 Zonal Ave. Los Angeles California 90033"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Laurie L.","family":"McLeod","sequence":"additional","affiliation":[{"name":"Institute for Toxicology University of Southern California, School of Pharmacy Los Angeles California 90033"},{"name":"Department of Pathology University of Southern California, School of Pharmacy 1985 Zonal Ave. Los Angeles California 90033"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[1987,9]]},"reference":[{"key":"e_1_2_2_2_1","first-page":"1628","volume":"349","author":"Scholan N.A.","year":"1968","journal-title":"Hoppe\u2010Seyler's Z. 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