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Molecules 2016, 21(12), 1723; doi:10.3390/molecules21121723

Improving Free Radical Scavenging Activity of Soy Isoflavone Glycosides Daidzin and Genistin by 3′-Hydroxylation Using Recombinant Escherichia coli

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, Tainan 70005, Taiwan
*
Author to whom correspondence should be addressed.
Academic Editor: Jean-Marc Sabatier
Received: 12 November 2016 / Revised: 7 December 2016 / Accepted: 13 December 2016 / Published: 15 December 2016
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products)
View Full-Text   |   Download PDF [1665 KB, uploaded 15 December 2016]   |  

Abstract

The present study describes the biotransformation of a commercially available crude extract of soy isoflavones, which contained significant amounts of the soy isoflavone glycosides daidzin and genistin, by recombinant Escherichia coli expressing tyrosinase from Bacillus megaterium. Two major products were isolated from the biotransformation and identified as 3′-hydroxydaidzin and 3′-hydroxygenistin, respectively, based on their mass and nuclear magnetic resonance spectral data. The two 3′-hydroxyisoflavone glycosides showed potent 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity with IC50 values of 7.4 and 9.8 μM for 3′-hydroxydaidzin and 3′-hydroxygenistin, respectively. The free radical scavenging activities of the two 3′-hydroxyisoflavone glycosides were, respectively, 120 and 72 times higher than the activity of their precursors, daidzin and genistin, and were also stronger than the activity of ascorbic acid, which showed an IC50 value of 15.1 μM. This is the first report of the bio-production and potential antioxidant applications of both 3′-hydroxydaidzin and 3′-hydroxygenistin. View Full-Text
Keywords: antioxidant; biotransformation; daidzin; genistin; hydroxylation antioxidant; biotransformation; daidzin; genistin; hydroxylation
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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.; Wang, D.-S.; Chang, T.-S. Improving Free Radical Scavenging Activity of Soy Isoflavone Glycosides Daidzin and Genistin by 3′-Hydroxylation Using Recombinant Escherichia coli. Molecules 2016, 21, 1723.

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