Enzymatic Synthesis and Anti-Allergic Activities of Curcumin Oligosaccharides
Kei Shimoda1 and Hiroki Hamada2
1Department of Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan. 2Department of Life Science, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan.
Abstract
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.
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