α-Glucosidase inhibitors isolated from medicinal plants

Yin, Zhenhua; Zhang, Wei; Feng, Fan; Zhang, Yong; Kang, Wenyi

doi:10.1016/j.fshw.2014.11.003

Cited by 366 publications

(276 citation statements)

References 73 publications

(127 reference statements)

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“…Compounds 16, 17, and 19 have all previously been reported as α-glucosidase inhibitors [42,43], but this is the first report of the α-glucosidase inhibitory activity of 20, 26, and 29. Compounds 16, 19, 20, 26, and 29 all showed higher α-glucosidase inhibitory activity than the clinically approved antidiabetic drug acarbose (Table 1), which supports the use of Eremanthus as an antidiabetic herbal medicine.…”

Section: Isolation and Pharmacological Evaluation Of The α-Glucosidasmentioning

confidence: 83%

High-Resolution α-Glucosidase Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of Antidiabetic Compounds in Eremanthus crotonoides (Asteraceae)

et al. 2016

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α-Glucosidase inhibitors decrease the cleavage-and absorption rate of monosaccharides from complex dietary carbohydrates, and represent therefore an important class of drugs for management of type 2 diabetes. In this study, a defatted ethyl acetate extract of Eremanthus crotonoides leaves with an inhibitory concentration (IC 50 ) of 34.5 µg/mL towards α-glucosidase was investigated by high-resolution α-glucosidase inhibition profiling combined with HPLC-HRMS-SPE-NMR. This led to identification of six α-glucosidase inhibitors, namely quercetin (16), trans-tiliroside (17), luteolin (19), quercetin-3-methyl ether (20), 3,5-di-O-caffeoylquinic acid n-butyl ester (26) and 4,5-di-O-caffeoylquinic acid n-butyl ester (29). In addition, nineteen other metabolites were identified. The most active compounds were the two regioisomeric di-O-caffeoylquinic acid derivatives 26 and 29, with IC 50 values of 5.93 and 5.20 µM, respectively. This is the first report of the α-glucosidase inhibitory activity of compounds 20, 26, and 29, and the findings support the important role of Eremanthus species as novel sources of new drugs and/or herbal remedies for treatment of type 2 diabetes.

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Section: Isolation and Pharmacological Evaluation Of The α-Glucosidasmentioning

confidence: 83%

High-Resolution α-Glucosidase Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of Antidiabetic Compounds in Eremanthus crotonoides (Asteraceae)

et al. 2016

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“…In recent years, considerable attention has been paid to natural products as inhibitory ligands of the α -glucosidase enzyme. 5,6 However, the chemical complexity of, for example, plant extracts makes identification and characterization of inhibitory ligands from these complex mixtures a challenging and time-consuming task.…”

mentioning

confidence: 99%

Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: α-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae

et al. 2015

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A bioanalytical platform combining magnetic ligand fishing for α-glucosidase inhibition profiling and HPLC-HRMS-SPE-NMR for structural identification of α-glucosidase inhibitory ligands, both directly from crude plant extracts, is presented. Magnetic beads with N-terminus-coupled α-glucosidase were synthesized and characterized for their inherent catalytic activity. Ligand fishing with the immobilized enzyme was optimized using an artificial test mixture consisting of caffeine, ferulic acid, and luteolin before proof-of-concept with the crude extract of Eugenia catharinae. The combination of ligand fishing and HPLC-HRMS-SPE-NMR identified myricetin 3-O-α-l-rhamnopyranoside, myricetin, quercetin, and kaempferol as α-glucosidase inhibitory ligands in E. catharinae. Furthermore, HPLC-HRMS-SPE-NMR analysis led to identification of six new alkylresorcinol glycosides, i.e., 5-(2-oxopentyl)resorcinol 4-O-β-d-glucopyranoside, 5-propylresorcinol 4-O-β-d-glucopyranoside, 5-pentylresorcinol 4-O-[α-d-apiofuranosyl-(1→6)]-β-d-glucopyranoside, 5-pentylresorcinol 4-O-β-d-glucopyranoside, 4-hydroxy-3-O-methyl-5-pentylresorcinol 1-O-β-d-glucopyranoside, and 3-O-methyl-5-pentylresorcinol 1-O-[β-d-glucopyranosyl-(1→6)]-β-d-glucopyranoside.

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“…As a standard, acarbose has lower binding energy and inhibition constant (ΔG =-8.16 kcal/mol, Ki = 0.02 µM) than miglitol and voglibose. Acarbose as α-glucosidase inhibitor, can effectively control blood glucose levels after food intake and have been used clinically in the treatment of diabetes mellitus [22]. β-sitosterol was shown as the molecule to have the lowest binding energy (ΔG =-10.61 kcal/mol) and inhibition constant (Ki = 0.02 µM).…”

Section: Fig 1: Model Of α-Glucosidase Enzymementioning

confidence: 99%

SCREENING OF Α-Glucosidase INHIBITORS FROM TERMINALIA CATAPPA L. FRUITS USING MOLECULAR DOCKING METHOD AND IN VITRO TEST

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Mun’im

Yanuar

et al. 2016

Int J Pharm Pharm Sci

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Objective: Terminalia catappa L. (T. catappa L.) fruit has inhibitory activity on α-glucosidase, therefore, can be a potential natural source for the treatment of type II diabetes mellitus. Inhibitory activity of ethanol fruit extract with IC50 3.02 µg/ml was the strongest inhibition when compared with 54 medicinal plants used as an antidiabetic agent Methods: Molecular docking using AutoDock 4.2 was performed to predict the binding modes of α-glucosidase enzyme from Saccharomyces cereviciae with 13 chemical constituents of T. catappa. α-Glucosidase enzyme was obtained from Protein Data Bank (PDB code: 3A4A). Acarbose, voglibose and miglitol were used as standards. Docking result determines the highest binding energy (ΔG) and inhibition constants (Ki) as an active compound. Visualization of amino acid residues around the active compound was identified with PyMOL and LigPlot. Screening of active compound was carried out by T. catappa L. fruit remaceration extraction use hexane and ethyl acetate. Ethyl acetate extract was separated on silica gel column chromatography using n-hexane, ethyl acetate and methanol sequentially based on polarity of each solvent. Identification of an active compound from ethyl acetate sub fractions using TLC and GC-MS method. The inhibitory activity of the active compound of α-glucosidase was determined with in vitro test using α-glucosidase enzyme.in Indonesia. This project was aimed to find the active compound from T. catappa L. fruit using molecular docking, identification ethyl acetate subfraction using TLC and GC-MC, determine in vitro test on α-glucosidase inhibitory activity from ethyl acetate extract and subfraction. Results:The highest binding energy and inhibition constant is β-sitosterol with ΔG-10.61 kcal/mol and Ki 0.02 µM. The ligand was situated around of 18 amino acid residues. Ethyl acetate subfractions A, B and C showed that subfraction B contains similar spot characteristic and Rf value (0.42) with β-Sitosterol standard. Identification with GC-MS gave β-sitosterol acetate and sitostenone. Redocking process of β-sitosterol acetate and sitostenone showed ΔG-11.14 kcal/mol and-9.79 kcal/mol with Ki 0.01 μM and 0.07 μM respectively. In vitro test of acarbose, ethyl acetate extract and subfraction B gave IC50 Conclusion: Three steroids that are β-sitosterol, β-sitosterol acetate and sitostenone were the active compounds responsible for α-glucosidase inhibitory activity of T. catappa L. fruit. According to the in vitro test, ethyl acetate extract has stronger α-glucosidase inhibitory activity than ethyl acetate subfraction B.17.52; 192.51 and 296.28 µg/ml.

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α-Glucosidase inhibitors isolated from medicinal plants

Cited by 366 publications

References 73 publications

High-Resolution α-Glucosidase Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of Antidiabetic Compounds in Eremanthus crotonoides (Asteraceae)

High-Resolution α-Glucosidase Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of Antidiabetic Compounds in Eremanthus crotonoides (Asteraceae)

Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: α-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae

SCREENING OF Α-Glucosidase INHIBITORS FROM TERMINALIA CATAPPA L. FRUITS USING MOLECULAR DOCKING METHOD AND IN VITRO TEST

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