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A‐ring oxidation products from γ‐irradiation of cholesterol in liposomes
Author(s) -
Maerker G.,
Jones K. C.
Publication year - 1993
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02545305
Subject(s) - autoxidation , liposome , cholesterol , chemistry , ring (chemistry) , irradiation , vesicle , stereochemistry , organic chemistry , biochemistry , membrane , physics , nuclear physics
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.