ABSTRACT
The α-glucosidase inhibitory activities of bergenin derivatives were evaluated. Bergenin derivatives were synthesized from bergenin which is a characteristic compound of B. ligulata. A new bergenin derivative, 11-O-(3',4'-dimethoxybenzoyl)-bergenin showed the highest potent inhibitory activity among those of bergenin derivatives. The presence of substituents at 3',4'-position in bergenin derivatives altered the α-glucosidase inhibitory activity. 11-O-(3',4'-dimethoxybenzoyl)-bergenin was noncompetitive inhibitor for α-glucosidase. The present study reveals that bergenin derivatives could be classified as a new group of α-glucosidase inhibitors.
Subject(s)
Benzopyrans/chemistry , Benzopyrans/pharmacology , Enzyme Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors , Saxifragaceae/chemistry , Benzopyrans/isolation & purification , Dose-Response Relationship, Drug , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Molecular Structure , Saccharomyces cerevisiae/enzymology , Structure-Activity Relationship , alpha-Glucosidases/metabolismABSTRACT
The chemical composition of the volatile oil from roots of Bergenia ligulalta was analyzed by GC-MS. A total of 97 compounds were identified. (+)-(6S)-Parasorbic acid (1) (47.45%), isovaleric acid (6.25%), 1,8-cineole (4.24%), (Z)-asarone (3.50%), and terpinen-4-ol (2.96%) were the most prominent constituents. (+)-(6S)-Parasorbic acid (1) was isolated and characterized by spectroscopic data. This is the first report of the existence of (+)-(6S)-parasorbic acid in the saxifrage family. The volatile oil and the isolated compound were tested against Drosophila melanogaster . The results obtained showed that the volatile oil from roots could be considered as natural insecticidal effect agents.
Subject(s)
Insecticides , Oils, Volatile/chemistry , Saxifragaceae/chemistry , Animals , Drosophila melanogaster , Gas Chromatography-Mass Spectrometry , Lactones/chemistry , Lactones/isolation & purification , Plant Oils/chemistry , Plant Roots/chemistryABSTRACT
Inhibitory compound of alpha-glucosidase activity, (+)-afzelechin (1), was isolated from rhizomes of Bergenia ligulata. The structure was identified by IR, EI-MS, (1)H and (13)C NMR spectroscopy. The ID(50) (50% inhibition dose) value of compound 1 was 0.13 mM. To investigate the structure-activity relationship, (+)-afzelechin tetraacetate (2), (+)-5,7,4'-trimethoxyafzelechin (3), (+)-tetramethoxyafzelechin (4), and (+)-3-acetyl-5,7,4'-trimethoxyafzelechin (5) as the derivatives of compound 1 were evaluated as well.
