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Int. J. Mol. Sci. 2015, 16(11), 27816-27823; doi:10.3390/ijms161126070

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
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Marianne Su-Ling Brooks
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)
View Full-Text   |   Download PDF [1618 KB, uploaded 25 November 2015]   |  

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. 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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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