Novel sterol transformations promoted by Saccharomyces cerevisiae strain GL7: evidence for 9 beta, 19-cyclopropyl to 9(11)-isomerization and for 14-demethylation to 8(14)-sterols

Abstract

Cultures of Saccharomyces cerevisiae strain GL7 (a sterol auxotroph) were incubated with nonradioactive and tritium-labeled cycloartenol, and the sterol composition of the cells was examined by chemical (GLC, TLC, HPLC, MS, 1H-NMR, and 13C-NMR) and radiotracer techniques. Several novel sterols were isolated from the cells including 14 alpha-methyl ergosta-9(11),24(28)-dien-3 beta-ol, 24 beta-methyl-9 beta,19-cyclopropyl ergost-8(14)-en-3 beta-ol, and 9 beta,19-cyclopropyl ergosta-7(8),24(28)-dien-3 beta-ol. GL7 converted [2-3H]cycloartenol to [2-3H]ergosterol in low yield (1% incorporation), whereas [2-3H]lanosterol was converted to [2-3H]ergosterol in high yield (41% incorporation). The degree of sterol absorption and transformation by GL7 was dependent on the type and amount of sterol(s) in the growth medium. The results demonstrate for the first time that yeast may transform 9 beta,19-cyclopropyl sterols to 9(11)-sterols and delta 5-sterols and that 14-demethylation of sterols may proceed in GL7 to double bond formation either in the 8(14)-position or in the 14(15)-position.