Biotransformation of 8-hydroxydaidzein by recombinant Escherichia coli expressing O-methyltransferase (OMT) SpOMT2884 from Streptomyces peucetius was investigated. Two metabolites were isolated and identified as 7,4′-dihydroxy-8-methoxy-isoflavone (1) and 8,4′-dihydroxy-7-methoxy-isoflavone (2), based on mass, 1H-nuclear magnetic resonance (NMR) and 13C-NMR spectrophotometric analysis. The maximum production yields of compound (1) and (2) in a 5-L fermenter were 9.3 mg/L and 6.0 mg/L, respectively. The two methoxy-isoflavones showed dose-dependent inhibitory effects on melanogenesis in cultured B16 melanoma cells under non-toxic conditions. Among the effects, compound (1) decreased melanogenesis to 63.5% of the control at 25 μM. This is the first report on the 8-O-methylation activity of OMT toward isoflavones. In addition, the present study also first identified compound (1) with potent melanogenesis inhibitory activity.
CITATION STYLE
Chiang, C. M., Ding, H. Y., Tsai, Y. T., & Chang, T. S. (2015). Production of two novel methoxy-isoflavones from biotransformation of 8-hydroxydaidzein by recombinant Escherichia coli Expressing O-methyltransferase SpOMT2884 from Streptomyces peucetius. International Journal of Molecular Sciences, 16(11), 27816–27823. https://doi.org/10.3390/ijms161126070
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