Synthesis of Gentiooligosaccharides of Genistein and Glycitein and Their Radical Scavenging and Anti-Allergic Activity

The synthesis of gentiooligosaccharides of genistein and glycitein using cultured cells of Eucalyptus perriniana as biocatalysts was investigated. The cells of E. perriniana glycosylated genistein and glycitein to give the corresponding 4'-O-β-glucosides, 7-O-β-glucosides, and 7-O-β-gentiobiosides, which were two new compounds. The β-glucosides of genistein and glycitein showed 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging activity and superoxide-radical scavenging activity. On the other hand, 7-O-β-glucosides of genistein and glycitein and the 7-O-β-gentiobioside of glycitein exerted inhibitory effects on IgE antibody production.