Synthesis of Xylooligosaccharides of Daidzein and Their Anti-Oxidant and Anti-Allergic Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Biocatalytic Glycosylation of Daidzein (1) by Cultured Cells of C. roseus and Aspergillus sp. β-Xylosidase
2.2. Anti-Oxidant Activity of Glycosides of Daidzein
2.3. Anti-Allergic Activity of Glycosides of Daidzein
2.4. Water-Solubility of Glycosides of Daidzein
3. Experimental Section
3.1. General
3.2. Cell Line and Culture Conditions
3.3. Glycosylation of Daidzein by C. roseus
3.4. Glycosylation of Daidzein 7-O-β-Primeveroside by Aspergillus sp. β-Xylosidase
3.5. DPPH Radical Scavenging Activity
3.6. Superoxide-Radical Scavenging Activity
3.7. Suppressive Action on IgE Antibody Formation
3.8. Water-Solubility
4. Conclusions
Acknowledgments
References
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Product | 2 | 3 | 4 | 5 |
---|---|---|---|---|
2 | 153.0 | 153.1 | 153.1 | 153.1 |
3 | 122.0 | 122.0 | 122.1 | 122.1 |
4 | 174.6 | 174.6 | 174.6 | 174.6 |
5 | 127.0 | 127.0 | 127.0 | 127.0 |
6 | 115.5 | 115.5 | 115.4 | 115.4 |
7 | 161.2 | 161.3 | 161.3 | 161.3 |
8 | 103.3 | 103.3 | 103.3 | 103.3 |
9 | 157.2 | 157.2 | 157.2 | 157.1 |
10 | 118.4 | 118.4 | 118.4 | 118.4 |
1′ | 123.6 | 123.6 | 123.6 | 123.6 |
2′ | 130.0 | 130.0 | 130.0 | 130.0 |
3′ | 114.9 | 114.9 | 114.9 | 114.9 |
4′ | 157.0 | 156.9 | 156.9 | 156.9 |
5′ | 114.9 | 114.9 | 114.9 | 114.9 |
6′ | 130.0 | 130.0 | 130.0 | 130.0 |
1″ | 99.5 | 99.9 | 99.9 | 99.5 |
2″ | 73.0 | 73.0 | 73.3 | 73.0 |
3″ | 77.0 | 77.0 | 76.0 | 76.8 |
4″ | 69.5 | 69.8 | 69.9 | 69.5 |
5″ | 76.4 | 76.1 | 75.9 | 76.4 |
6″ | 60.7 | 60.5 | 68.7 | 68.8 |
1‴ | 103.5 | 103.5 | ||
2‴ | 72.9 | 72.8 | ||
3‴ | 76.5 | 76.1 | ||
4‴ | 69.3 | 78.2 | ||
5‴ | 60.9 | 61.0 | ||
1‴′ | 103.6 | |||
2‴′ | 72.9 | |||
3‴′ | 76.7 | |||
4‴′ | 68.9 | |||
5‴′ | 60.8 |
Compound | IC50 (μM) | |
---|---|---|
DPPH Free-Radical Scavenging | Superoxide-Radical Scavenging | |
1 | 50 | 751 |
2 | 70 | 802 |
3 | 55 | 767 |
4 | 121 | 870 |
5 | 177 | 908 |
Vitamin C | 38 | 698 |
Compound | IgE Level a |
---|---|
None | 410.0 |
1 | 141.7 |
2 | 422.5 |
3 | 158.0 |
4 | 197.7 |
5 | 339.8 |
Hydrocortisone | 338.0 |
Compound | Water-Solubility (μmol/mL) | Fold a |
---|---|---|
1 | 1.2 × 10−3 | 1 |
2 | 3.5 × 10−2 | 29 |
3 | 4.0 × 10−2 | 33 |
4 | 0.2 | 183 |
5 | 1.0 | 850 |
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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. https://doi.org/10.3390/ijms12095616
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. https://doi.org/10.3390/ijms12095616
Chicago/Turabian StyleShimoda, Kei, Hiroki Hamada, and Hatsuyuki Hamada. 2011. "Synthesis of Xylooligosaccharides of Daidzein and Their Anti-Oxidant and Anti-Allergic Activities" International Journal of Molecular Sciences 12, no. 9: 5616-5625. https://doi.org/10.3390/ijms12095616