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In Silico Study of Apigenin and Apigetrin As Inhibitor of 3-Hydroxy-3-Methyl-Glutayl-Coenzyme a Reductase

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In Silico Study of Apigenin and Apigetrin As Inhibitor of 3-Hydroxy-3-Methyl-Glutayl-Coenzyme a Reductase Online - 2455-3891 Vol 10, Issue 11, 2017 Print - 0974-2441 Research Article IN SILICO STUDY OF APIGENIN AND APIGETRIN AS INHIBITOR OF 3-HYDROXY-3-METHYL-GLUTAYL-COENZYME A REDUCTASE DWINTHA LESTARI1*, ELIN YULINAH SUKANDAR1, IRDA FIDRIANNY2 1Department of Pharmacology-Clinical Pharmacy, School of Pharmacy, Bandung Institute of Technology, Bandung, Indonesia. 2Department of Pharmaceutical Biology, School of Pharmacy, Bandung Institute of Technology, Bandung, Indonesia. Email: [email protected] Received: 05 June 2017, Revised and Accepted: 31 July 2017 ABSTRACT Objective: The objectives of this research were to investigate in silico interaction between apigenin and apigetrin with 3-hydroxy-3-methyl-glutayl- coenzyme A (HMG Co-A) reductase, to find the most favorable binding site as well as to predict the binding mode. Materials and Methods: Docking calculation was performed by branded Sony Vaio PC Linux Ubuntu 14.04 LTS. The binding process based on the best docking result with HMG Co-A reductase was presented in two-dimensional diagram. Statin, atorvastatin, and R-mevalonate were used as standard. Results: binding interaction Binding affinity than apigetrin. and inhibition constant of R-mevalonate were Ei=−4.2 kcal/mol, Ki=836.78 µM; apigenin Ei=−7.0 kcal/mol, Ki=7.43 µM; apigetrin Ei=−5.9 kcal/mol, Ki=47.53 µM; simvastatin Ei=−8.2 kcal/mol; Ki=0.98 µM; atorvastatin Ei=−8.4 kcal/mol; Ki=0.7 µM. Apigenin had better Conclusion: Apigenin could be developed as anticholesterol. Keywords: Anticholesterol, In silico, Apigenin, Apigetrin, 3-hydroxy-3-methyl-glutayl-coenzyme A reductase. © 2017 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons. org/licenses/by/4. 0/) DOI: http://dx.doi.org/10.22159/ajpcr.2017.v10i11.20493 INTRODUCTION against obesity and related metabolic disturbances by exploring the There are four major types of lipoproteins, classified by their densities metabolicon obesity and were transcriptional unclear; therefore, responses the inprotective high-fat diet-inducedeffects of apigenin obese as measured in the ultracentrifuge: (1) Very low density lipoproteins, which contain high concentrations of triglycerides and moderate and molecular action mechanism were not explained. mice were evaluated [8]. However, studies of other active compounds density lipoproteins, which are very low-density lipoproteins from whichconcentrations a share ofof both the cholesterol triglycerides and has phospholipids; been removed, (2) intermediate- so that the glucoside. There are very few reports regarding its anticancer activity. InApigetrin, previous also in silicoknown research as apigenin-7-O-glucoside represented that Apigetrin is a natural can flavonoid act as a density lipoproteins, which are derived from intermediate-density multitargeted agent that targets six different anticancer drug target lipoproteinsconcentrations by of removing cholesterol almost and phospholipids all of the triglycerides, are increased; leaving (3) low- an, especially high concentration of cholesterol and a moderately high adhesion kinase, topoisomerase-ii, dihydrofolate reductase, and P-glycoprotein.such as mouse Apigetrindouble minute gave more2, phosphatidylinositol negative-binding free 3 kinase, energies focal as smallerconcentration concentrations of phospholipids; of cholesterol and and (4) phospholipids high-density [1]. lipoproteins, which contain a high concentration of protein (about 50%) but much 3-hydroxy-3-methyl-glutayl-coenzymean indication of favorable interaction against A (HMG these Co-A) targets reductase [9]. is the to the flavone class that is the aglycone of several naturally occurring rate-controlling enzyme of the mevalonate pathway, the metabolic glycosides.Apigenin (4′,5,7-trihydroxyflavone) In in vitro experiments is anda natural animal product studies, belonging various pathway that produces cholesterol and other isoprenoids. In humans, biological activities of apigenin have been reported. Apigenin may the gene for HMG Co-A reductase is located on the long arm of the fifth support a possible chemopreventive role by inducing autophagy (a chromosome [10]. HMG Co-A reductase is anchored in the membrane kind of cellular waste-recycling system) in leukemia cells. Inducing in of the endoplasmic reticulum, and was long regarded as having seven transmembrane domains, which the active site located in a long carboxyl terminal domain in the cytosol. Evidence of more studies denoted that anautophagy enzyme willresponsible interfere foraction the ofmetabolism chemotherapy of many drug pharmaceuticalvincristine [2]. it contained eight transmembrane domains [11]. drugsApigenin in wasthe usedbody. for Apigenin stem cell demonstrated [3] and a potent to inhibitorprevent renalof CYP2C9 damage [4] which was caused by cyclosporine in rats, associated with reducing A drug with goog solubility properties will show better absorption in expression of the cell death mediator bcl-2 in histopathological theand 3-hydroxy-3-methylglutaryl-coenzyme bioavailability. Almost 40% of the drug A (HMG in the CoA) market reductase presents are low the sections [5]. Cyclosporine enhances the expression of transforming mostsolubility effective in water. inhibitor It is causing for lowering the drug cholesterol slowly to which be absorbed catalyse [12]. conversion Statin, usedgrowth to factor-βevaluate in apigenin the rat kidney, and its which effect signifieson cyclosporine-induced accelerated apoptosis. renal of HMG-CoA to mevalonate [13]. Simvastatin was developed by Merck and Therefore, transformingIn vitro previous growth research factor-β revealed and apoptotic that apigenin index may be in vitro and in vivo studies presented anti-inflammatory,damage [6]. antidiabetic, and antiobesity effects of apigenin. classcame knowninto medical as statins, use inwhich 1992 are [14], used and primarily the most as important a lipid lowering medications agent However,toxic to red the blood long-term cells [7]. supplementary Several effects of low-dose apigenin andneeded for preventingin a basic health a correlation system [15]. with Atorvastatin cardiovascular is a disease. member of the drug Lestari et al. Asian J Pharm Clin Res, Vol 10, Issue 11, 2017, 284-287 MATERIALS AND METHODS deviation (RMSD) values calculations were performed using rms_cur module in PyMol. This process was repeated 100 times for each Material protein pdb files. The docking process was performed to HMG Co-A Docking calculation was performed by branded Sony Vaio PC Linux reductase as receptor, while simvastatin and atorvastatin, apigenin and apigetrin were used as ligands ( Ubuntu 14.04 LTS as the operating system, with Intel 2.40 GHzCore i5, 100 times to each protein. Fig. 2). This process was iterated chipset: Intel HM55, memory: 4 GB DDR3 SODIMM PC-8500, video: ATI Mobility Rade on HD 5430 512 MB, hard drive: 500 GB Serial ATA 7200 RESULTS AND DISCUSSION RPM. The softwares used for docking preparation were Chem Bio Office Ultra 13.0 Suite (Trial Version), ligand Explorer Viewer 4.1.0 (Online: is a naturally occurring, non-toxic, non-mutagenic phytonutrient http://www.pdb.org/pdb/explore/), Q-SiteFinder (online: http:// flavonoid,Apigenin commonly(5,7-dihydroxy-2-(4-hydroxyphenyl)-4H- present in various fruits, and vege chromen-4-one)tables. Apigenin www.modelling.leeds.ac.uk/qsitefinder/), YASARA 13.9.8, Autodock has long been considered to have various biological activities such as Vina, PyRx 0.8, MGLTools1.5.6 (Auto Dockdiagram Tools-1.5.6),s of docking Chimera poses. 1.8. Virtual analysis of docking site was used Autodock Tools 1.5.6 and Pose types. The basic structure of cholesterol is a sterol nucleus. In humans, View to generated two-dimensional (2D) Experimental cholesterolanti-inflammatory is derived [16] from and twoantitumorigenic sources – diet effect and [17] de novo in various synthesis. cell The subjected receptor in this study was HMG Co-A reductase All nucleated cells can synthesize cholesterol de novo from acetyl CoA ( . 1). The structure of the receptor was obtained in pdb files from the protein data bank (www.pdb.org). The receptor code for Fig limiting step in the mevalonate pathway is the conversion of HMG Co-Athrough to mevalonate the mevalonate by HMG 12 pathway,Co-A reductase. which occursHMG Co-A in the reductase ER. The is rate an with pepstatin as native ligand, which has been known as aspartic integral membrane protein which is under regulation through a negative proteaseHMG Co-A inhibitor. reductase was 4I6Y. Each receptor had been docked validation was aimed to examine whether the docking protocols can In preparation step, separation of native ligand for each receptor feedback system modulated by the SREBP pathway [18]. The internal was carried out using Structure Protonation and Recognition used in the internal validation was the RMSD value between the heavy reproduce the pose of the cocrystal ligand [19]. The objective function file to protein and ligands using the splitpdb module. The protein atoms of the docked pose and the crystal structure pose. The protocol is System (SPORES) software. SPORES was employed to split the pdb acceptable the reference ligand was also recognized, protonated, and stored values from redocking process for each crystal structures (Table 1), it was recognized, protonated, and stored as protein.mol2, while can be concluded if the RMSD that the value docking is <2.0 protocols [20]. By dividing were valid. the result of RMSD coordinatesas
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