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Int. J. Mol. Sci. 2011, 12(9), 5616-5625; doi:10.3390/ijms12095616
Article

Synthesis of Xylooligosaccharides of Daidzein and Their Anti-Oxidant and Anti-Allergic Activities

1,* , 2,*  and 3
1 Department of Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan 2 Department of Life Science, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan 3 National Institute of Fitness and Sports in Kanoya, 1 Shiromizu-cho, Kagoshima 891-2390, Japan
* Authors to whom correspondence should be addressed.
Received: 7 June 2011 / Revised: 17 August 2011 / Accepted: 18 August 2011 / Published: 31 August 2011
(This article belongs to the Special Issue Antioxidants)
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Abstract

The biocatalytic synthesis of xylooligosaccharides of daidzein was investigated using cultured cells of Catharanthus roseus and Aspergillus sp. β-xylosidase. The cultured cells of C. roseus converted daidzein into its 4'-O-β-glucoside, 7-O-β-glucoside, and 7-O-β-primeveroside, which was a new compound. The 7-O-β-primeveroside of daidzein was further xylosylated by Aspergillus sp. β-xylosidase to daidzein trisaccharide, i.e., 7-O-[6-O-(4-O-(β-D-xylopyranosyl))-β-D-xylopyranosyl]-β-D-glucopyranoside, which was a new compound. The 4'-O-β-glucoside, 7-O-β-glucoside, and 7-O-β-primeveroside of daidzein exerted DPPH free-radical scavenging and superoxide radical scavenging activity. On the other hand, 7-O-β-glucoside and 7-O-β-primeveroside of daidzein showed inhibitory effects on IgE antibody production.
Keywords: daidzein; xylooligosaccharide; biocatalyst; anti-oxidant activity; anti-allergic activity daidzein; xylooligosaccharide; biocatalyst; anti-oxidant activity; anti-allergic activity
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.

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MDPI and ACS Style

Shimoda, K.; Hamada, H.; Hamada, H. Synthesis of Xylooligosaccharides of Daidzein and Their Anti-Oxidant and Anti-Allergic Activities. Int. J. Mol. Sci. 2011, 12, 5616-5625.

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