An improved water-soluble/stereospecific biotransformation of aporphine alkaloids in Stephania epigaea to 4R-hydroxyaporphine alkaloids by Clonostachys rogersoniana

• Aporphine alkaloids in S. epigaea were transformed into 4R-hydroxyaporphine alkaloids.
• The biotransformation occurred by fermentation with C. rogersoniana.
• The biotransformation was validated by solid- and liquid-state fermentations.
• The produced alkaloids were more water soluble than the original alkaloids.
• Cytochrome P450 enzymes were confirmed to participate in the catalysis.

Aporphine alkaloids were transformed into the corresponding stereospecific 4R-hydroxyaporphine alkaloids through the solid-state fermentation of Stephania epigaea with Clonostachys rogersoniana. This process was validated by both solid- and liquid-state fermentations with aporphine alkaloids as substrates. Cytochrome P450 enzymes were confirmed to participate in the catalysis of this biotransformation. 4R-Hydroxyaporphine alkaloids exhibit the same levels of acetylcholinesterase (AChE) inhibitory and cytotoxic activities as aporphine alkaloids and are considerably more water soluble than aporphine alkaloids, indicating their potential as water-soluble AChE inhibitors and antitumor agents. This paper suggests that C. rogersoniana fermentation can facilitate a novel biotransformation of aporphine alkaloids in S. epigaea to 4R-hydroxyaporphine alkaloids.

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