Chromatographic behavior of oxygenated derivatives of cholesterol

Oxygenated derivatives of cholesterol have important functions in many biochemical processes. These oxysterols are difficult to study because of their low physiological concentrations, the facile formation of cholesterol autoxidation artifacts, and lack of information on their chromatographic behavi...

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Bibliographic Details
Published in:Steroids 2003-03, Vol.68 (3), p.221-233
Main Authors: Shan, Hui, Pang, Jihai, Li, Shengrong, Chiang, Tony B, Wilson, William K, Schroepfer, George J
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chemical Phenomena
Chemistry, Physical
Cholesterol - analysis
Cholesterol - chemistry
Chromatography, Gas - methods
Chromatography, High Pressure Liquid - instrumentation
Chromatography, High Pressure Liquid - methods
Chromatography, Ion Exchange - methods
Deuterated sterols
Fluorinated sterols
Fundamental and applied biological sciences. Psychology
GC/MS
Gels
Isotopic fractionation
Oxygen - chemistry
Oxysterols
Silicon Dioxide - chemistry
Silver - chemistry
Stereoisomerism
TLC
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Summary:Oxygenated derivatives of cholesterol have important functions in many biochemical processes. These oxysterols are difficult to study because of their low physiological concentrations, the facile formation of cholesterol autoxidation artifacts, and lack of information on their chromatographic behavior. Focusing on metabolites and autoxidation products of cholesterol, we have documented the chromatographic mobilities of 35 oxysterols under a variety of conditions: eight solvent systems for thin-layer chromatography on silica gel, several mobile phases for reversed-phase high-performance liquid chromatography (HPLC), and two types of stationary phase for capillary gas chromatography (GC) using trimethylsilyl derivatives. Notable differences in selectivity could be obtained by modifying the stationary or mobile phases. Separations of oxysterol pairs isomeric at side-chain carbons or C-7 were achieved on normal-phase, reversed-phase, chiral, or silver-ion HPLC columns. Chromatographic behavior is also described for side-chain hexadeuterated and heptafluorinated oxysterols, which are useful as standards in isotope dilution analyses and autoxidation studies, respectively. The overall results are relevant to many problems of oxysterol analysis, including the initial separation of oxysterols from cholesterol, determination of highly polar and nonpolar oxysterols, separation of isomeric pairs, selection of derivatization conditions for GC analysis, and quantitation of the extent of cholesterol autoxidation.
ISSN:0039-128X
1878-5867
DOI:10.1016/S0039-128X(02)00185-X