Biotransformation of tissue-specific hormone tibolone with fungal culture Trichothecium roseum

• Biotransformation of tibolone (1) with Trichothecium roseum has being carried out for the first time.
• Two new and three known metabolites 2–6 were isolated from fermentation of tibolone (1).
• Effect of fungal cultures on compound 1 modification has been studied.
• Functionalization could be difficult by conventional chemical methods.
• Structures of new metabolites 5 and 6 were characterized by 2D NMR spectroscopy and mass spectrometry.

Whole cells based biotransformation is an important tool for bioconversion of steroids. It can be used to synthesize biologically potent compounds with diverse structures. Biotransformation of tissue-specific hormone tibolone (1) with Trichothecium roseum (ATCC 13411) has being carried out for the first time. Two new and three known metabolites 2–6 were isolated from fermentation of tibolone (1) with Trichothecium roseum and their structures were characterized by 2D NMR spectroscopy and mass spectrometry. The relative stereochemistry of new metabolites 5 and 6 was deduced by 2D NOESY experiments. The effect of cultures on tibolone structural modifications and time-course studies has also been conducted.