MICROBIAL HYDROXYLATIONS .4. DIFFERENTIAL METABOLISM OF 19-NOR STEROID ANTIPODES BY CURVULARIA LUNATA

In order to explore the generality of prior findings that microbial systems hydroxylate both the natural d and the unnatural l enantiomers of racemic 19-norsteroids, the metabolic disposition of d- and dl-19-nortestosterone and its dl-13β-ethyl homolog by vegetative cell cultures of Curvularia lunata NRRL 2380 was examined. From d-19-nortestosterone there was obtained the d-10β-hydroxy, d-11β-hydroxy, d-14α-hydroxy, d-6β-hydroxy, and d-10β,11β-droxydroxy derivatives. From dl-19-nortestosterone there wss obtained the d-10β-hydroxy, dl-14α-hydroxy;, dl-11β-hydroxy, dl-6β-hydroxy, l-12±-hydroxy, and dl-10β,11β-dihydroxy derivatives together with l-10β,11β,17β-trihydroxy-5α-estran-3-one. From dl-13β-ethyl-17β-hydroxygon-4-en-3-one there was obtained the dl-10β-hydroxy, l-12α-hydroxy, d-14α-hydroxy, dl-6β-hydroxy, and d-6β,10β-dihydroxy derivatives. Structures of each product were established by elemental analysis, spectral behavior in ethanol, alkaline ethanol, and concentrated sulfuric acid, proton spectra, derivitization, and optical rotatory dispersion. These results support and expand on our prior similar results using Aspergillus ochraceus NRRL 405 on these same substrates. © 1969, American Chemical Society. All rights reserved.