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Open AccessArticle

Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of Deinococcus geothermalis

1
Department of Biological Sciences and Technology, National University of Tainan, Tainan 70005, Taiwan
2
Biodiversity Research Center, Academia Sinica, Taipei 115, Taiwan
3
Department of Food Science, National Quemoy University, Kinmen County 892, Taiwan
4
Department of Biotechnology, Chia Nan University of Pharmacy and Science, No. 60, Sec. 1, Erh-Jen Rd., Jen-Te District, Tainan 71710, Taiwan
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Josefina Aleu
Molecules 2019, 24(12), 2236; https://doi.org/10.3390/molecules24122236
Received: 30 May 2019 / Revised: 9 June 2019 / Accepted: 14 June 2019 / Published: 15 June 2019
(This article belongs to the Special Issue Biocatalytic Synthesis of Bioactive Compounds)
8-Hydroxydaidzein (8-OHDe), an ortho-hydroxylation derivative of soy isoflavone daidzein isolated from some fermented soybean foods, has been demonstrated to possess potent anti-inflammatory activity. However, the isoflavone aglycone is poorly soluble and unstable in alkaline solutions. To improve the aqueous solubility and stability of the functional isoflavone, 8-OHDe was glucosylated with recombinant amylosucrase of Deinococcus geothermalis (DgAS) with industrial sucrose, instead of expensive uridine diphosphate-glucose (UDP-glucose). One major product was produced from the biotransformation, and identified as 8-OHDe-7-α-glucoside, based on mass and nuclear magnetic resonance spectral analyses. The aqueous solubility and stability of the isoflavone glucoside were determined, and the results showed that the isoflavone glucoside was almost 4-fold more soluble and more than six-fold higher alkaline-stable than 8-OHDe. In addition, the anti-inflammatory activity of 8-OHDe-7-α-glucoside was also determined by the inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells. The results showed that 8-OHDe-7-α-glucoside exhibited significant and dose-dependent inhibition on the production of nitric oxide, with an IC50 value of 173.2 µM, which remained 20% of the anti-inflammatory activity of 8-OHDe. In conclusion, the well-soluble and alkaline-stable 8-OHDe-7-α-glucoside produced by recombinant DgAS with a cheap substrate, sucrose, as a sugar donor retains moderate anti-inflammatory activity, and could be used in industrial applications in the future. View Full-Text
Keywords: 8-hydroxydaidzein; stable; soluble; anti-inflammation; amylosucrase; Deinococcus geothermalis 8-hydroxydaidzein; stable; soluble; anti-inflammation; amylosucrase; Deinococcus geothermalis
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Chang, T.-S.; Wang, T.-Y.; Yang, S.-Y.; Kao, Y.-H.; Wu, J.-Y.; Chiang, C.-M. Potential Industrial Production of a Well-Soluble, Alkaline-Stable, and Anti-Inflammatory Isoflavone Glucoside from 8-Hydroxydaidzein Glucosylated by Recombinant Amylosucrase of Deinococcus geothermalis. Molecules 2019, 24, 2236.

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