Abstract
Neurospora crassa. Shear & B.O. Dodge (Sordariaceae), the red bread mold, when incubated with exogenous nandrolone decanoate for 6 days at 25°C, produced four steroid metabolites. The microbial products were purified by preparative thin-layer chromatography and high-performance liquid chromatography followed by their identification through 1H, 13C NMR and other spectroscopic data. The fermentation yielded estr-4-en-3,17-dione (II), 17β.-hydroxyestr-4-en-3-one (III), 6β.,17β.-dihydroxyestr-4-en-3-one (IV), and 9β.,17β.-dihydroxyestr-4-en-3-one (V). Characteristics observed were ester hydrolysis, hydroxyl group oxidation, and 9α.- or 6β.-hydroxylations.