Products of the reaction of cholesterol with hypochlorite anion.
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.
Momynaliev
K T
KT
Institute of Physico-Chemical Medicine, Russian Ministry of Health Care and Medical Products, Moscow, Russia.
Osipova
S V
SV
Sadovskaya
V L
VL
Govorun
V M
VM
Sergienko
V I
VI
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
D003102:Colloids; D008077:Lipoproteins, LDL; D008081:Liposomes; D010713:Phosphatidylcholines; D006997:Hypochlorous Acid; D002784:Cholesterol