Three new polyhydroxytriterpenoid derivatives, 23-O-neochebuloylarjungenin 28-O-β-d-glycopyranosyl ester (1), 23-O-4'-epi-neochebuloylarjungenin (2), and 23-O-galloylpinfaenoic acid 28-O-β-d-glucopyranosyl ester (17) were isolated from the fruits of Terminalia chebula Retz. along with fourteen known ones. Their structures were elucidated by 1D and 2D NMR spectroscopic data and acid hydrolysis. After evaluating for Baker's yeast α-glucosidase, rat intestinal α-glucosidase, and porcine pancreatic α-amylase inhibitory activities of all the isolated compounds, 23-O-galloylarjunolic acid (11, IC50 21.7μM) and 23-O-galloylarjunolic acid 28-O-β-d-glucopyranosyl ester (12, IC50 64.2μM) showed potent inhibitory activities against Baker's yeast α-glucosidase compared to the positive control, acarbose (IC50 174.0μM). However, all the tested compounds except for the positive control, acarbose, had no or only weak inhibitory activity against rat intestinal α-glucosidase and porcine pancreatic α-amylase.