SOLID PHASE MICROBIAL REACTIONS OF SEX HORMONE, TRANS-ANDROSTERONE WITH FILAMENTOUS FUNGI
Keywords:
Solid phase medium, Microbial Transformation, Trans-androsterone, Rhizopus stolonifer, Fusarium lini, HydroxylationAbstract
Objective: A microbial biotransformation study was performed on trans-androsterone (1) using solid phase medium. In the present context, trans-androsterone (1), a sex hormone was fermented with two filamentous fungi, Rhizopus stolonifer (black bread mold) and Fusarium lini.
Methods: Sabouraud-4% glucose-agar were used to cultivate the fungal cultures as solid phase medium. Substrate 1 was incubated with R. stolonifer (ATCC 10404) and F. lini (NRRL 68751) for 8 days. Microbial transformed metabolites were purified by using column chromatographic technique.
Results: The metabolism study of 1 revealed that various metabolites were detected when incubated with filamentous fungi. A total of 3 transformed products were obtained. The reactions occurred that exhibited diversity; including selective hydroxylation at C-6 and C-7 along with oxidation occurs at C-3 positions. Their structure and identified on the basis of extensive spectroscopic data (NMR, HREIMS, IR and UV) as 3b,7b-dihydroxy-5a-androstan-17-one 2 in a good yield (58%), 6b-hydroxy-5a-androstan-3,17-dione 3, and 3b,6b-dihydroxy-5a-androstan-17-one 4.
Conclusion: Solid phase microbial transformation method can successfully be used for the development of new steroidal drugs. The modified steroidal molecules could favor when compared to their natural counterparts due to several medicinal advantages.
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References
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