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A comparison of the biological properties of of androst‐5‐en‐3β‐ol, a series of (20R)‐ n ‐alkylpregn‐5‐en‐3β‐ols and 21‐isopentylcholesterol with those of cholesterol
Author(s) -
Nes William R.,
Adler John H.,
Billheimer Jeffrey T.,
Erickson Katherine A.,
Joseph John M.,
Landrey Josephine R.,
MarcaccioJoseph Rosemarie,
Ritter Karla S.,
Conner Robert L.
Publication year - 1982
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/bf02535113
Subject(s) - sterol , tetrahymena pyriformis , cholesterol , lecithin , yeast , biochemistry , biology , liposome , desmosterol , saccharomyces cerevisiae , steroid , egg lecithin , stereochemistry , chemistry , tetrahymena , hormone
The Δ 5 ‐sterol, androst‐5‐en‐3β‐ol, which has no side chain at C‐17, did not permit molting of the insect Heliothis zea , growth of either the protozoan Tetrahymena pyriformis , or the yeast Saccharomyces cerevisiae adapted to anaerobic conditions, nor was the sterol esterified by a mammalian microsomal ACAT preparation. However, the sterol did form a liposome with egg lecithin and, when fed to mice, did inhibit hepatic cholesterol synthesis. 21‐Isopentylcholesterol also formed a liposome but neither supported the growth of the yeast nor was metabolized by the protozoan. When sterols, 20(R)‐ n ‐alkylpregn‐5‐en‐3β‐ols, with side chains of varying lengths were added to the medium of the protozoan, maximal esterification with fatty acids occurred with the 20(R)‐ n ‐pentyl derivative, and maximal inhibition of tetrahymanol formation occurred with the n ‐butyl, n ‐pentyl and n ‐hexyl derivatives. In all of the assays, cholesterol showed a positive response, either permitting molting or growth, being metabolized, inhibiting sterol or tetrahymanol synthesis, or forming a liposome.