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

• Record Type: Journal Article
• Authors: Lee, Dong Young; Kim, Hyun Woo; Yang, Heejung; Sung, Sang Hyun
• Is Part Of: Phytochemistry. Volume 137(2017)
• Page Start: 109
• Page End: 116
• Publication Date: 2017-05
• Subjects: Terminalia chebula -- Combretaceae α-glucosidase -- Hydrolyzable tannin -- IC50 value; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2017.02.006
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: 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. Graphical abstract: Forty-eight hydrolyzable tannins, including three previous unknown and six artifacts were isolated from the fruits of Terminalia chebula . All isolates were evaluated for their α -glucosidase inhibitory activities. Of these, 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 shown above had the significant inhibitory activities against α -glucosidase. Highlights: Forty-eight hydrolyzable tannins including nine hitherto unknown were isolated from the fruits of Terminalia chebula. α-Glucosidase inhibitory activities of the all isolates were evaluated. Two at the nine above compounds showed significant inhibitory activities against α-glucosidase (IC50 2.9 and 6.4 μM).