Next Article in Journal
Do We Need Anti-Prion Compounds to Treat Alzheimer’s Disease?
Next Article in Special Issue
Mapping the Biotransformation of Coumarins through Filamentous Fungi
Previous Article in Journal
Formation of Polyethylene Glycol Particles Using a Low-Temperature Supercritical Assisted Atomization Process
Article

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
Show Figures

Figure 1

MDPI and ACS Style

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. https://doi.org/10.3390/molecules24122236

AMA Style

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(12):2236. https://doi.org/10.3390/molecules24122236

Chicago/Turabian Style

Chang, Te-Sheng, Tzi-Yuan Wang, Szu-Yi Yang, Yu-Han Kao, Jiumn-Yih Wu, and Chien-Min Chiang. 2019. "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 24, no. 12: 2236. https://doi.org/10.3390/molecules24122236

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop