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Reaction of cholesterol 5,6‐epoxides with simulated gastric juice
Author(s) -
Maerker Gerhard,
Nungesser Edwin H.,
Bunick Frank J.
Publication year - 1988
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536218
Subject(s) - epoxide , triol , chemistry , hydrolysis , diol , organic chemistry , chromatography , catalysis
Cholesterol 5α,6α‐epoxide (α‐epoxide) and cholesterol 5β,6β‐epoxide (β‐epoxide) were individually suspended in simulated gastric juice (pH 1.2) at 37 C, and their reaction was followed by gradient high performance liquid chromatography (HPLC) with flame ionization (FID) detection. Both epoxides reacted rapidly in the aqueous acid medium. The α‐epoxide formed 6β‐chlorocholestane‐3β,5α‐diol (α‐chlorohydrin) and 5α‐cholestane‐3β,5,6β‐triol (triol), while the β‐epoxide formed 5α‐chlorocholestane‐3β,6β‐diol (β‐chlorohydrin) and triol. The isomeric chlorohydrins reacted further to form the triol. In mildly alkaline aqueous medium, each chlorohydrin reverted to the epoxide from which it was formed. The data suggest that both epoxides, which have been reported to have adverse health effects in animals, would be largely hydrolyzed in the stomach and to the triol, which also has been reported to have biological activity. The data furher suggest that residual chlorohydrins surviving stomach residence can be expected to revert to epoxide in the more alkaline intestinal environment.