A comparison of the biological properties of androst-5-en-3 beta-ol, a series of (20R)-n-alkylpregn-5-en-3 beta-ols and 21-isopentylcholesterol with those of cholesterol.

The delta 5-sterol, androst-5-en-3 beta-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-3 beta-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.