title: New polyhydroxytriterpenoid derivatives from fruits of Terminalia chebula Retz. and their α-glucosidase and α-amylase inhibitory activity.
abstract: 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, IC5021.7μM) and 23-O-galloylarjunolic acid 28-O-β-d-glucopyranosyl ester (12, IC5064.2μM) showed potent inhibitory activities against Baker's yeast α-glucosidase compared to the positive control, acarbose (IC50174.0μM). 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.
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul 151-742, Republic of Korea.
authors.forename: Dong Young
authors.initials: DY
authors.lastname: Lee
authors.affiliation: College of Pharmacy, Kangwon National University, Chuncheon 200-701, Republic of Korea.
authors.forename: Heejung
authors.initials: H
authors.lastname: Yang
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul 151-742, Republic of Korea.
authors.forename: Hyun Woo
authors.initials: HW
authors.lastname: Kim
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul 151-742, Republic of Korea. Electronic address: shsung@snu.ac.kr.
authors.forename: Sang Hyun
authors.initials: SH
authors.lastname: Sung
mesh_terms: D000818:Animals; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015394:Molecular Structure; D051381:Rats; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013329:Structure-Activity Relationship; D013552:Swine; D029766:Terminalia / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000516:alpha-Amylases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000520:alpha-Glucosidases / Q000378:metabolism*
chemical_list: C000620848:23-O-galloylarjunolic acid; C000620849:23-O-galloylarjunolic acid 28-O-glucopyranosyl ester; D004791:Enzyme Inhibitors; D005960:Glucosides; D014315:Triterpenes; D000516:alpha-Amylases; D000520:alpha-Glucosidases
keywords: Polyhydroxytriterpenoids; Terminalia chebula; α-Amylase; α-Glucosidase