Maplexins, new α-glucosidase inhibitors from red maple (Acer rubrum) stems

Thirteen gallic acid derivatives including five new gallotannins, named maplexins A-E, were isolated from red maple (Acer rubrum) stems. The compounds were identified by spectral analyses. The maplexins varied in number and location of galloyl groups attached to 1,5-anhydro-D-glucitol. The isolates were evaluated for a-glucosidase inhibitory and antioxidant activities. Maplexin E, the first compound identified with three galloyl groups linked to three different positions of 1,5-anhydro-D-glucitol, was 20 fold more potent than the a-glucosidase inhibitory drug, Acarbose (IC50 = 8 vs 160 mu M). Structure-activity related studies suggested that both number and position of galloyls attached to 1,5-anhydro-D-glucitol were important for a-glucosidase inhibition. (C) 2011 Elsevier Ltd. All rights reserved.