Production of two novel methoxy-isoflavones from biotransformation of 8-hydroxydaidzein by recombinant Escherichia coli Expressing O-methyltransferase SpOMT2884 from Streptomyces peucetius

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Abstract

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.

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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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