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Open AccessArticle

Production of Two Novel Methoxy-Isoflavones from Biotransformation of 8-Hydroxydaidzein by Recombinant Escherichia coli Expressing O-Methyltransferase SpOMT2884 from Streptomyces peucetius

1
Department of Biotechnology, Chia Nan University of Pharmacy & Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan
2
Department of Cosmetics Science, Chia Nan University of Pharmacy & Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan
3
Department of Biological Sciences and Technology, National University of Tainan, No. 33, Sec. 2, Shu-Lin St., Tainan 70005, Taiwan
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Marianne Su-Ling Brooks
Int. J. Mol. Sci. 2015, 16(11), 27816-27823; https://doi.org/10.3390/ijms161126070
Received: 5 November 2015 / Revised: 17 November 2015 / Accepted: 18 November 2015 / Published: 24 November 2015
(This article belongs to the Special Issue Bioprocess Engineering)
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. View Full-Text
Keywords: 7,4′-dihydroxy-8-methoxy-isoflavone; 8,4′-dihydroxy-7-methoxy-isoflavone; 8-hydroxydaidzein; melanogenesis; inhibition; O-methyltransferase; SpOMT2884 7,4′-dihydroxy-8-methoxy-isoflavone; 8,4′-dihydroxy-7-methoxy-isoflavone; 8-hydroxydaidzein; melanogenesis; inhibition; O-methyltransferase; SpOMT2884
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Chiang, C.-M.; Ding, H.-Y.; Tsai, Y.-T.; Chang, T.-S. Production of Two Novel Methoxy-Isoflavones from Biotransformation of 8-Hydroxydaidzein by Recombinant Escherichia coli Expressing O-Methyltransferase SpOMT2884 from Streptomyces peucetius. Int. J. Mol. Sci. 2015, 16, 27816-27823.

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