Hydrolyzable tannins from the fruits of Terminalia chebula Retz and their α-glucosidase inhibitory activities. 2017

Dong Young Lee, and Hyun Woo Kim, and Heejung Yang, and Sang Hyun Sung
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, 151-742, Republic of Korea.

Nine hydrolyzable tannins, including three previously unknown and six artifacts, were isolated, together with thirty-nine known ones, from the fruits of Terminalia chebula Retz. (Combretaceae). They were identified as 1,2,3-tri-O-galloyl-6-O-cinnamoyl-β-d-glucose, 1,2,3,6-tetra-O-galloyl-4-O-cinnamoyl-β-d-glucose, 4-O-(2″,4″-di-O-galloyl-α-l-rhamnosyl)ellagic acid, 1'-O-methyl neochebulanin, dimethyl neochebulinate, 6'-O-methyl neochebulagate, dimethyl neochebulagate, dimethyl 4'-epi-neochebulagate, and methyl chebulagate by the spectroscopic interpretation. After evaluation for α-glucosidase inhibition of all isolated compounds, 1,2,3,6-tetra-O-galloyl-4-O-cinnamoyl-β-d-glucose and 4-O-(2″,4″-di-O-galloyl-α-l-rhamnosyl)ellagic acid showed significant inhibitory activities with IC50 values of 2.9 and 6.4 μM, respectively. In addition, inhibition kinetic studies showed that both compounds have mixed-type inhibitory activities with the inhibition constants (Ki) of 1.9 and 4.0 μM, respectively.

UI MeSH Term Description Entries
D010936 Plant Extracts Concentrated pharmaceutical preparations of plants obtained by removing active constituents with a suitable solvent, which is evaporated away, and adjusting the residue to a prescribed standard. Herbal Medicines,Plant Extract,Extract, Plant,Extracts, Plant,Medicines, Herbal
D005638 Fruit The fleshy or dry ripened ovary of a plant, enclosing the seed or seeds. Berries,Legume Pod,Plant Aril,Plant Capsule,Aril, Plant,Arils, Plant,Berry,Capsule, Plant,Capsules, Plant,Fruits,Legume Pods,Plant Arils,Plant Capsules,Pod, Legume,Pods, Legume
D000520 alpha-Glucosidases Enzymes that catalyze the exohydrolysis of 1,4-alpha-glucosidic linkages with release of alpha-glucose. Deficiency of alpha-1,4-glucosidase may cause GLYCOGEN STORAGE DISEASE TYPE II. Acid Maltase,Lysosomal alpha-Glucosidase,Maltase,Maltases,Maltase-Glucoamylase,Neutral Maltase,Neutral alpha-Glucosidase,alpha-Glucosidase,Lysosomal alpha Glucosidase,Maltase Glucoamylase,Neutral alpha Glucosidase,alpha Glucosidase,alpha Glucosidases,alpha-Glucosidase, Lysosomal,alpha-Glucosidase, Neutral
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D047348 Hydrolyzable Tannins Polymeric derivatives of GALLIC ACID that are esters of a sugar. Ellagi-Tannins,Ellagitannins,Gallo-Tannins,Gallotannins,Pyrogallol Tannins,Ellagi Tannins,Gallo Tannins,Tannins, Hydrolyzable,Tannins, Pyrogallol
D029766 Terminalia A plant genus of the family COMBRETACEAE. Members contain arjunin, an ellagitannin (TANNINS). Myrobalans,Arjun Tree,Arjuna Tree,Terminalia arjuna,Arjun Trees,Arjuna Trees,Myrobalan,Terminalias,Tree, Arjun,Tree, Arjuna,Trees, Arjun,Trees, Arjuna
D065089 Glycoside Hydrolase Inhibitors Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. alpha-Glucosidase Inhibitor,alpha-Glucosidase Inhibitors,Intestinal alpha-Amylase Inhibitors,Pancreatic alpha-Amylase Inhibitors,alpha-Amylase Inhibitors, Pancreatic,Hydrolase Inhibitors, Glycoside,Inhibitor, alpha-Glucosidase,Inhibitors, Glycoside Hydrolase,Inhibitors, Intestinal alpha-Amylase,Inhibitors, Pancreatic alpha-Amylase,Inhibitors, alpha-Glucosidase,Intestinal alpha Amylase Inhibitors,Pancreatic alpha Amylase Inhibitors,alpha Amylase Inhibitors, Pancreatic,alpha Glucosidase Inhibitor,alpha Glucosidase Inhibitors,alpha-Amylase Inhibitors, Intestinal

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