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Synthesis of Xylooligosaccharides of Daidzein and Their Anti-Oxidant and Anti-Allergic Activities
Department of Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan
Department of Life Science, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan
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; in revised form: 17 August 2011 / Accepted: 18 August 2011 / Published: 31 August 2011
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
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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.
Shimoda K, Hamada H, Hamada H. Synthesis of Xylooligosaccharides of Daidzein and Their Anti-Oxidant and Anti-Allergic Activities. International Journal of Molecular Sciences. 2011; 12(9):5616-5625.
Shimoda, Kei; Hamada, Hiroki; Hamada, Hatsuyuki. 2011. "Synthesis of Xylooligosaccharides of Daidzein and Their Anti-Oxidant and Anti-Allergic Activities." Int. J. Mol. Sci. 12, no. 9: 5616-5625.