Synthesis of Oligosaccharides of Genistein and Quercetin as Potential Anti-inflammatory Agents

Genistein was glucosylated to its 7-O-β-d-glucoside by cultured cells of Ipomoea batatas, while cultured Marchantia polymorpha cells produced 4′-O-β-d-glucoside and 7-O-β-d-glucoside of genistein. On the other hand, quercetin was converted into its 3-O-β-d-glucoside by I. batatas, and M. polymorpha gave 3-O-β-d-glucoside and 7-O-β-d-glucoside of quercetin. These four glucosides were further glycosylated to the corresponding β-maltosides and β-maltotriosides by cyclodextrin glucanotransferase. Genistein 7-O-β-maltooligosaccharides, quercetin 3-O-β-glucoside, and quercetin 7-O-β-maltooligosaccharides showed potent inhibitory effects on histamine release from rat peritoneal mast cells.