CONFIGURATION AT C-24 IN OOGONIOL (24R-3-BETA,11-ALPHA,15-BETA,29-TETRAHYDROXYSTIGMAST-5-EN-7-ONE) AND IDENTIFICATION OF 24(28)-DEHYDROOOGONIOLS AS HORMONES IN ACHLYA

Model steroids, 29-hydroxysitosterol and 29-hydroxyclionasterol, have been prepared. Comparison of their NMR spectra (220 MHz, Fourier transform), which show distinct differences, with that of oogoniol-1 indicates that the latter has the same configuration at C-24 as 29-hydroxyclionasterol. Oogoniol-1 isolated from culture liquids of Achlya is accompanied by a small proportion of the 24(28)-dehydro analogue, 3², 11±, 15±, 29-tetrahydroxystigmasta-5, 24(28)(E)-dien-7-one 3²-isobutyrate. The two compounds can be separated by high-pressure liquid chromatography. The biological activity of the latter is considerably higher than that of oogoniol-1. © 1979, American Chemical Society. All rights reserved.