C-C bond cleavage by flavonoid C-glycosidase

Our ongoing research efforts have discovered rare chemical conversions that achieved by intestinal bacteria. Cleavage of C-C bond of flavonoid C-glycosides is one of them. Puerarin is converted to daidzein by the putative deglycosidase expressed by anaerobic bacterium. Chemical and biochemical study on the C-glycoside deglycosylation, including synthesis of substrate analogs and deglycosidation by model system, are underway.

C-O bond cleavage by cobalamin-dependent O-demethylase

Cobalamin-dependent O-demethylase expressed by Blautia sp. MRG-PMF1 can cleave aryl methyl ethers, including polymethoxyflavones. Reactivity and enzyme reaction mechanism of cobalamin-catalyzed C-O cleavage is studied by means of bioinorganic chemical approaches.