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Molecules 2017, 22(1), 87; doi:10.3390/molecules22010087

Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains

1
Department of Biotechnology, Chia Nan University of Pharmacy and Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan
2
Department of Biological Sciences and Technology, National University of Tainan, No. 33, Sec. 2, Shu-Lin St., Tainan 70005, Taiwan
3
Institute of Biotechnology and Chemical Engineering, I-Shou University, No. 1, Sec. 1, Syuecheng Rd., Dashu District, Kaohsiung 84001, Taiwan
4
Center for General Education, National Quemoy University, No. 1, University Road., Jin-Ning Township, Kinmen County 892, Taiwan
*
Authors to whom correspondence should be addressed.
Academic Editor: David J. Newman
Received: 17 November 2016 / Revised: 20 December 2016 / Accepted: 3 January 2017 / Published: 4 January 2017
(This article belongs to the Special Issue Natural Product: A Continuing Source of Novel Drug Leads)
View Full-Text   |   Download PDF [680 KB, uploaded 4 January 2017]   |  

Abstract

Biotransformation of the soy isoflavone genistein by sequential 3′-hydroxylation using recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium and then methylation using another recombinant E. coli expressing O-methyltransferase from Streptomyces peucetius was conducted. The results showed that two metabolites were produced from the biotransformation, identified as 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone, respectively, based on their mass and nuclear magnetic resonance spectral data. 5,7,4′-Trihydroxy-3′-methoxyisoflavone showed potent antiproliferative activity toward mouse B16 melanoma cells with an IC50 value of 68.8 μM. In contrast, the compound did not show any cytotoxicity toward mouse normal fibroblast cells, even at 350 μM concentration. The results of the present study offer insight on the production of both 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone by two recombinant E. coli strains and the potential anti-melanoma applications of 5,7,4′-trihydroxy-3′-methoxyisoflavone. View Full-Text
Keywords: genistein; melanoma; methoxyisoflavone; methyltransferase; tyrosinase genistein; melanoma; methoxyisoflavone; methyltransferase; tyrosinase
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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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Chiang, C.-M.; Chang, Y.-J.; Wu, J.-Y.; Chang, T.-S. Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains. Molecules 2017, 22, 87.

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