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Characterization of ?-Glucosidase Inhibitors from Psychotria malayana Jack Leaves Extract Using LC-MS-Based Multivariate Data Analysis and In-Silico Molecular Docking.

ABSTRACT: Psychotria malayana Jack has traditionally been used to treat diabetes. Despite its potential, the scientific proof in relation to this plant is still lacking. Thus, the present study aimed to investigate the ?-glucosidase inhibitors in P.malayana leaf extracts using a metabolomics approach and to elucidate the ligand-protein interactions through in silico techniques. The plant leaves were extracted with methanol and water at five various ratios (100, 75, 50, 25 and 0% v/v; water-methanol). Each extract was tested for ?-glucosidase inhibition, followed by analysis using liquid chromatography tandem to mass spectrometry. The data were further subjected to multivariate data analysis by means of an orthogonal partial least square in order to correlate the chemical profile and the bioactivity. The loading plots revealed that the m/z signals correspond to the activity of ?-glucosidase inhibitors, which led to the identification of three putative bioactive compounds, namely 5'-hydroxymethyl-1'-(1, 2, 3, 9-tetrahydro-pyrrolo (2, 1-b) quinazolin-1-yl)-heptan-1'-one (1), ?-terpinyl-?-glucoside (2), and machaeridiol-A (3). Molecular docking of the identified inhibitors was performed using Auto Dock Vina software against the crystal structure of Saccharomyces cerevisiae isomaltase (Protein Data Bank code: 3A4A). Four hydrogen bonds were detected in the docked complex, involving several residues, namely ASP352, ARG213, ARG442, GLU277, GLN279, HIE280, and GLU411. Compound 1, 2, and 3 showed binding affinity values of -8.3, -7.6, and -10.0 kcal/mol, respectively, which indicate the good binding ability of the compounds towards the enzyme when compared to that of quercetin, a known ?-glucosidase inhibitor. The three identified compounds that showed potential binding affinity towards the enzymatic protein in molecular docking interactions could be the bioactive compounds associated with the traditional use of this plant.

SUBMITTER: Nipun TS

PROVIDER: S-EPMC7763559 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Characterization of α-Glucosidase Inhibitors from Psychotria malayana Jack Leaves Extract Using LC-MS-Based Multivariate Data Analysis and In-Silico Molecular Docking.

Nipun Tanzina Sharmin TS Khatib Alfi A Ibrahim Zalikha Z Ahmed Qamar Uddin QU Redzwan Irna Elina IE Saiman Mohd Zuwairi MZ Supandi Farahaniza F Primaharinastiti Riesta R El-Seedi Hesham R HR

Molecules (Basel, Switzerland) 20201212 24

Psychotria malayana Jack has traditionally been used to treat diabetes. Despite its potential, the scientific proof in relation to this plant is still lacking. Thus, the present study aimed to investigate the α-glucosidase inhibitors in P.malayana leaf extracts using a metabolomics approach and to elucidate the ligand-protein interactions through in silico techniques. The plant leaves were extracted with methanol and water at five various ratios (100, 75, 50, 25 and 0 ...[more]

PMID: 33322801

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Project description:Psychotria malayana Jack leaf, known in Indonesia as "daun salung", is traditionally used for the treatment of diabetes and other diseases. Despite its potential, the phytochemical study related to its anti-diabetic activity is still lacking. Thus, this study aimed to identify putative inhibitors of α-glucosidase, a prominent enzyme contributing to diabetes type 2 in P. malayana leaf extract using gas chromatography-mass spectrometry (GC-MS)- and nuclear magnetic resonance (NMR)-based metabolomics, and to investigate the molecular interaction between those inhibitors and the enzyme through in silico approach. Twenty samples were extracted with different solvent ratios of methanol-water (0, 25, 50, 75, and 100% v/v). All extracts were tested on the alpha-glucosidase inhibition (AGI) assay and analyzed using GC-MS and NMR. Multivariate data analysis through a partial least square (PLS) and orthogonal partial square (OPLS) models were developed in order to correlate the metabolite profile and the bioactivity leading to the annotation of the putative bioactive compounds in the plant extracts. A total of ten putative bioactive compounds were identified and some of them reported in this plant for the first time, namely 1,3,5-benzenetriol (1); palmitic acid (2); cholesta-7,9(11)-diene-3-ol (3); 1-monopalmitin (4); β-tocopherol (5); α-tocopherol (6); 24-epicampesterol (7); stigmast-5-ene (8); 4-hydroxyphenylpyruvic acid (10); and glutamine (11). For the evaluation of the potential binding modes between the inhibitors and protein, the in silico study via molecular docking was performed where the crystal structure of Saccharomyces cerevisiae isomaltase (PDB code: 3A4A) was used. Ten amino acid residues, namely ASP352, HIE351, GLN182, ARG442, ASH215, SER311, ARG213, GLH277, GLN279, and PRO312 established hydrogen bond in the docked complex, as well as hydrophobic interaction of other amino acid residues with the putative compounds. The α-glucosidase inhibitors showed moderate to high binding affinities (-5.5 to -9.4 kcal/mol) towards the active site of the enzymatic protein, where compounds 3, 5, and 8 showed higher binding affinity compared to both quercetin and control ligand.

Project description:Clausena indica (Datz.) Oliv fruit pericarps (CIOPs) is an important agro-industrial by-product rich in active components. In this article, the effects of traditional and green deep eutectic solvents (DESs) on the high-performance liquid chromatography (HPLC) characterization, antioxidant activities, and α-glucosidase-inhibitory activity of phenolic extracts from CIOPs were investigated for the first time. The results showed that ChCl-Gly and Bet-CA had higher extraction efficiency for the total phenolic content (TPC, 64.14-64.83 mg GAE/g DW) and total flavonoid content (TFC, 47.83-48.11 mg RE/g DW) compared with the traditional solvents (water, methanol, and ethyl acetate). LC-Q-Orbitrap-MS/MS was adopted to identify the phenolic compositions of the CIOPs extracts. HPLC-diode array detection (HPLC-DAD) results indicated that arbutin, (-)-epigallocatechin, chlorogenic acid, procyanidin B1, (+)-catechin, and (-)-epicatechin were the major components for all extracts, especially for deep eutectic solvents (DESs). In addition, ChCl-Xyl and ChCl-Gly extracts showed higher antioxidant activities against 2,2-diphenyl-1-picrylhydrazyl (DPPH•), 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid (ABTS+•), ferric reducing antioxidant power (FRAP), reducing power (RP), and cupric ion reducing antioxidant capacity (CUPRAC) than extracts extracted by other solvents. A strong α-glucosidase-inhibiting activity (IC50, 156.25-291.11 μg/ml) was found in three DESs extracts. Furthermore, in silico analysis of the major phenolics in the CIOPs extracts was carried out to explore their interactions with α-glucosidase. Multivariate analysis was carried out to determine the key factors affecting the antioxidant activity and α-glucosidase-inhibiting activity. In short, DES can be taken as a promising solvent for valorization and recovery of bioactive compounds from agro-industrial by-products. The results verified that CIOPs can be used as a prospective source rich in bio-active compounds applied in the food and pharmacy industries.

Dataset Information

Characterization of ?-Glucosidase Inhibitors from Psychotria malayana Jack Leaves Extract Using LC-MS-Based Multivariate Data Analysis and In-Silico Molecular Docking.

Publications

Characterization of <i>α</i>-Glucosidase Inhibitors from <i>Psychotria malayana</i> Jack Leaves Extract Using LC-MS-Based Multivariate Data Analysis and In-Silico Molecular Docking.

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