title: Products of the reaction of cholesterol with hypochlorite anion.
abstract: Products of the reaction of cholesterol with hypochlorite (OCI) in various systems (egg phosphatidylcholine liposomes, low-density lipoproteins, and aqueous colloidal dispersion of cholesterol) were separated and analyzed by TLC, HPLC, and gas chromatography-mass spectrometry. The reactions of hypochlorite with cholesterol result in the same reaction products in all treated systems. Eighteen fractions were isolated from the reaction mixture by normal-phase HPLC in hexane-isopropanol (95:5 v/v); these were then examined by gas chromatography-mass spectrometry. Six products less polar than cholesterol were isolated from the reaction mixture; two of them were identified as 4,6-cholesten-3-one and 4-cholesten-3,6-dione. Among the oxidation products more polar than cholesterol, nine compounds were identified; they are 5,7-cholestadien-3 beta-ol,3,5-cholestadien-7-one, 4-cholesten-3 beta, 6 beta-diol, 5-cholesten-3 beta, 7 beta-diol, cholestan-3 beta, 5 alpha, 6 beta-triol, 5 alpha-cholestan-3 beta-ol-6-one, 5-cholesten-3 beta-ol-7-one, 5 alpha, 6 alpha-epoxycholestan-3 beta-ol, and 5 alpha-cholesten-3,6-dione.
authors.affiliation: Institute of Physico-Chemical Medicine, Russian Ministry of Health Care and Medical Products, Moscow, Russia.
authors.forename: K T
authors.initials: KT
authors.lastname: Momynaliev
authors.forename: S V
authors.initials: SV
authors.lastname: Osipova
authors.forename: V L
authors.initials: VL
authors.lastname: Sadovskaya
authors.forename: V M
authors.initials: VM
authors.lastname: Govorun
authors.forename: V I
authors.initials: VI
authors.lastname: Sergienko
mesh_terms: D002784:Cholesterol / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003102:Colloids; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006997:Hypochlorous Acid / Q000378:metabolism* / Q000494:pharmacology*; D066298:In Vitro Techniques; D008077:Lipoproteins, LDL / Q000187:drug effects / Q000378:metabolism; D008081:Liposomes; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010713:Phosphatidylcholines
chemical_list: D003102:Colloids; D008077:Lipoproteins, LDL; D008081:Liposomes; D010713:Phosphatidylcholines; D006997:Hypochlorous Acid; D002784:Cholesterol