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The Identification of Bioactive Compounds from Turbinaria Ornata (Turner) J Pharmacogn J. 2019; 11(5):873-883. A Multifaceted Journal in the field of Natural Products and Pharmacognosy Original Article www.phcogj.com The Identification of Bioactive Compounds from Turbinaria ornata (Turner) J. Agaradh and Computational Studies S. Deepa*, K. Sujatha, D Velmurugan ABSTRACT Aim/Background: The present work was carried out to identify some of the bioactive components present in the Brown seaweed Turbinaria ornata by GC-MS technique, and to ascertain its medicinal properties. Materials and Methods: GC-MS analysis of some of S. Deepa*, K. Sujatha, D the potent volatile constituents present in the pet ether of Turbinaria ornata was performed. Velmurugan MD simulations were performed for complex structures of human secretory PLA2 and P38 kinase. GC-MS chromatogram showed peaks indicating the presence of various compounds Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Sri Ramachandra of interest. The interpretation of the mass spectrum of GC-MS was done using the University, Chennai, INDIA. Database of Indian Institute of Crop Processing Technology (IICPT). Twenty compounds were identified in pet ether extract of Turbinaria ornata. All 20 compounds were screened using Correspondence PASS online activity prediction server, for the possession of anti-inflammatory potency and S. Deepa the selected target proteins were subjected to molecular docking studies. MD simulations Assistant Professor, Department of were also performed for the top listed compound 16 which was identified from D3P extract Pharmaceutical Chemistry, Faculty of Pharmacy, Sri Ramachandra University, (2,3-Diphenylcyclopropyl)methyl phenyl sulfoxide, trans-). Similarly, the complex structure of Chennai, INDIA. PLA2 (phospho-ethanolamine, PE) and P38 kinase (3-(2-pyridine-4-ylethyl)-1H-indole) were E-mail: [email protected] simulated for comparative study. Results and Conclusion: Based on the in silico results, History the binding affinities for compounds of T. ornata were judged against known standards for • Submission Date: 21-03-2019; its capability to restrain inflammation and to promote possibility for scheming potential anti- • Review completed: 10-05-2019; inflammatory lead from natural compounds were discussed. • Accepted Date: 30-05-2019. Key words: Brown algae, T. ornata, GC-MS, Bioactive components, Molecular docking and simulation studies. DOI : 10.5530/pj.2019.11.140 Article Available online http://www.phcogj.com/v11/i5 INTRODUCTION for its antioxidant, anti-inflammatory, and cytotoxicity activity on murine melanoma and colon Copyright Allergic and inflammatory diseases are the cancer.7-9 But there have not been many reports on © 2019 Phcogj.Com. This is an open- most familiar diseases all around the world. The access article distributed under the terms the bioactive components responsible or which of the Creative Commons Attribution 4.0 prevalence, severity, and complexity of these supports their biological activity. Hence, the present International license. diseases are getting increased rapidly. Although communication deals with the Gas chromatography- the many synthetic drugs have given rise to Mass spectrometry (GC-MS) analysis of pet remarkable successes in the progress of novel ether and chloroform extracts of marine seaweed anti-inflammatory and anti-allergic drugs, the Turbinaria ornata and molecular docking studies of continuous use has led to the miscellaneous and identified compounds along with known synthetic objectionable side effects. Meanwhile, the apparent standard using Schrödinger maestro for its ability usage of natural products in the management of to suppress inflammation and to evaluate its anti- these diseases has yet to be fully explored. For the diabetic potency and further possibility for designing last several thousand years, Mankind recognized of potential anti-inflammatory and anti-diabetic that marine organisms contain substances lead from natural compounds were discussed. accomplished with potent biological activity. Only Phospholipase A2, human secretory phospholipase recently, the serious investigation of seaweeds was A2, and p38alpha MAP kinase are the enzymes started to say, only half a century ago. Currently, focused in this study for the anti-inflammatory vital pharmacological and therapeutic products are activity. These enzymes are the starting material for being acquired and dynamically sought from the sea.1,2 Among the seaweeds, brown algae represent the inflammatory process which makes it an ideal a rich source of many components like laminarins, target for the anti-inflammatory drugs. To the best fucoidans, and also alginic acids.3 Moreover, from of our knowledge, this is the first report on GC-MS the ancient time's seaweeds have been used in analysis of pet ether extract of T. ornata and in-silico 10-12 various fields like medicine, agriculture, etc.,4 Our docking studies of its active constituents. present study is focused on the brown seaweed MATERIALS AND METHODS Turbinaria ornata, a widespread species belonging to Phaeophyceae, which is rich in fucoids and The brown seaweed, Turbinaria ornata belongs to sulfated polysaccharides 5,6 and other components Phaeophyceae family was collected from Mandabam like phlorotannins, flavonoids, tannins, glycosides, district, Tamilnadu. They were cleansed two or etc. Turbinaria ornata has been earlier accounted three times with sea water followed by fresh water Cite this article: Deepa S, Sujatha K, Velmurugan D. The Identification of Bioactive Compounds from Turbinaria ornata (Turner) J. Agaradh and Computational Studies. Pharmacog Phcogj.com J. 2019;11(5):873-83. 873 Pharmacognosy Journal, Vol 11, Issue 5, Sep-Oct, 2019 Deepa, et al.: The Identification of Bioactive Compounds from Turbinaria ornata (Turner) J. Agaradh and Computational Studies to remove debris or intact sand particle. The samples were dried out probability values. To calculate the activity, we submitted a standard in the shade and milled in a mechanical grinder to reduce its particle Mol file of each compound drawn using the Chemsketch software. size. About 25 g of powder was transferred to Schott-Duran bottles and Steps involved in docking studies around 250 ml of pet ether in the ratio of 1:10 were added, and the contents of the bottle were stirred continuously at room temperature Molecular docking13 and dynamics studies are the procedure by which for two days, and then the extract was filtered, and the solvent is two molecules mingle together in a 3D space and are essential tools in separated by using simple distillation method. The concentrated extract structural biology and computer-aided drug design. 14-16 In this present was collected and evaporated at room temperature. It is then submitted study, molecular docking was carried out using Schrodinger software, to GC-MS examination. and the simulations were carried out using AMBER software. GC-MS Inquisition Preparation of protein and ligand The GC-MS analysis was carried out as per the standard method.10 Gas The 3D structure of P38alpha Map kinase (PDB ID: 1W84), human chromatography was done using Perkin-Elmer GC Clarus 500 system secretory phospholipase A2 from inflammatory exudates (PDB ID: and Gas Chromatograph interfaced to a Mass Spectrophotometer 1POE) and Phospholipase A2 (PDB ID 1FV0) were retrieved from (GC-MS) equipped through Elite-5MS fused silica capillary the PDB to validate anti-inflammatory potency of the 20 identified column (30 m x 0.25 mm x 0.2 μm) composed of 5% diphenyl/95% compounds. Using the tool “Protein Preparation Wizard,” the above dimethylpolysiloxane. For GC-MS detection, ionizing energy of 70eV said proteins were prepared for the computational studies. It includes was used using an electron ionization system. The carrier gas used was adding hydrogen atoms and atomic charges, removing water molecules, Helium gas (99.999%) at a constant flow rate of 1 ml/min, and 2 μl of optimization of hydrogen bond network and energy minimization the sample was injected with a split ratio of 10:1; injector temperature to remove clashes and strained bonds and angles with 0.30Å RMSD was set at 250°C. The oven temperature was planned from 110°C convergence criterion. Addition of hydrogen atoms and correction of (isothermal for 2min) with a rise of 100°C/min to 200°C, then 5°C/ bond orders were made for each of the inhibitor presents within the min to 280°C, ending with a 9 min isothermal at 280°C. Mass spectra active site without disturbing the bound conformation dictated by the were taken at 70eV; 200°C of inlet line source temperature a scanning crystal structure. On the other hand, 20 newly identified compounds interval of 0-2 min and mass scan starting from 45 to 450 (m/Z). and the co-crystallized ligands were optimized and performed energy Entire GC operation time was 36 minutes. The relative % amount was minimization using Ligprep. These Twenty compounds (ligands) were calculated by matching its peak area to the total areas. To handle mass identified by GC-MS interrogation from pet ether extract of T. ornata. spectra and chromatogram the Software adopted was Turbo mass The structures of the documented ligand molecules were reclaimed from (Version 5.2). the PubChem database, and few were drawn using CHEMSKETCH Components predicted using GC-MS analysis (ACDLABS 12.0) Analysis of both pet ether and chloroform extracts on the mass Induced fit docking (IFD) spectrum was done using the database of Indian Institute of crop Based on the PASS biological activity prediction results of the processing
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