Enzymatic Synthesis and Anti-Allergic Activities of Curcumin Oligosaccharides

Curcumin 4‘-O-glucooligosaccharides were synthesized by a two step-enzymatic method using almond β-glucosidase and cyclodextrin glucanotransferase (CGTase). Curcumin was glucosylated to curcumin 4‘-O-β-D-glucopyranoside by almond β-glucosidase in 19% yield. Curcumin 4‘-O-β-D-glucopyranoside was converted into curcumin 4‘-O-β-glucooligosaccharides, i.e. 4‘-O-β-maltoside (51%) and 4‘-O-β-maltotrioside (25%), by further CGTase-catalyzed glycosylation. Curcumin 4‘-O-β-glycosides showed suppressive action on IgE antibody formation and inhibitory effects on histamine release from rat peritoneal mast cells.