Formation of Three New Trisaccharide-azoxyglycosides by Transglucosylation by Cycad β-Glucosidase

Abstract

Three new trisaccharide-azoxyglycosides were formed from some azoxyglycosides by transglucosylation by a β-D-glucosidase from cycad seeds. These azoxyglycosides, named neocycasin H, I, and J, were identified as O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranoside of methylazoxymethanol (MAM), O-β-D-glucopyranosyl-(1→3)-[O-β-D-glucopyranosyl-(1→6)]-O-β-D-glucopyranoside of MAM, and O-β-D-glucopyranosyl-(1→3)-[O-β-D-xylopyranosyl-(1→6)]-O-β-D-glucopyranoside of MAM, respectively. On the basis of their structures, the mechanism of the formation of these neocycasins is also discussed.