To Study the Molecular Interaction between Acetylcholinesterase Enzymes and The Isolated Compounds from Clausena Harmandiana by Molecular Docking Technique
Keywords:
molecular docking, hAChE, TcAChE, coumarins, carbazole alkaloidsAbstract
This research aims to study the molecular interaction between acetylcholinesterases (AChEs), Homo sapiens (hAChE) and Torpedo californica (TcAChE) and the isolated Coumarins (Xanthoxyletin, Nordentatin, Dentatin and Clausarin) and Carbazole alkaloids (7-Methoxymukonal, 7-Methoxyheptaphylline and Heptaphylline) from Clausena harmandiana using in-silico molecular docking technique. Four standard acetylcholinesterase inhibitors are Donepezil, Rivastigmine, Galantamine, and Tacrine were used for re-docking process. The complex of hAChE or TcAChE with four standard acetylcholinesterase inhibitors displayed the binding energies value in the range -11.53 to -7.31 kcal/mol and -11.30 to -7.04 kcal/mol, which accorded to the previously study. Therefore, the optimized crystal structures of AChEs were further used in this study. The docking result showed the same pattern of molecular interaction via H-bonding, π -π interaction and hydrophobic interaction at Peripheral anionic site (PAS), and stability binding trend between AChEs and all tested compounds were observed. Coumarins displayed the stable complex with AChEs than carbazole alkaloids, especially Clausarin exhibited the most stability complex. To summarize, the isolated compounds from C. harmadiana, particularly coumarins have the high potential to be acetylcholinesterase inhibitor agent.
References
Ali, M. Y., Seong, S. H., Jung, H. A., Jannat, S., & Choi, J. S. (2018). Kinetics and molecular docking of dihydroxanthyletin-type coumarins from Angelica decursiva that inhibit cholinesterase and BACE1. Archives of Pharmacal Research, 41(7), 753–764. https://doi.org/10.1007/s12272-018-1056-9
Araújo, J. Q., Lima, J. A., Pinto, A. D. C., De Alencastro, R. B., & Albuquerque, M. G. (2011). Docking of the alkaloid geissospermine into acetylcholinesterase: A natural scaffold targeting the treatment of Alzheimer’s disease. Journal of Molecular Modeling, 17(6), 1401–1412.https://doi.org/10.1007/s00894-010-0841-2
Cheung, J., Rudolph, M. J., Burshteyn, F., Cassidy, M. S., Gary, E. N., Love, J., …, & Height, J. J. (2012). Structures of human acetylcholinesterase in complex with pharmacologically important ligands. Journal of Medicinal Chemistry, 55, 10282 - 10286. https://doi.org/10.1021/jm300871x
Cruz, I., Puthongking, P., Cravo, S., Palmeira, A., Cidade, H., Pinto, M., & Sousa, E. (2017). Xanthone and Flavone Derivatives as Dual Agents with Acetylcholinesterase Inhibition and Antioxidant Activity as Potential Anti-Alzheimer Agents. Journal of Chemistry, 2017, 1–16. https://doi.org/10.1155/2017/8587260
Froestl, W., Muhs, A., & Pfeifer, A. (2014). Cognitive Enhancers (Nootropics). Part 2: Drugs Interacting with Enzymes. Update 2014. Journal of Alzheimer’s Disease, 42(1), 1–68. https://doi.org/10.3233/JAD-140402
Giacobini, E. (2003). Cholinergic function and Alzheimer’s disease. International Journal of Geriatric Psychiatry, 18, S1–S5. https://doi.org/10.1002/gps.935
Jantakoon, P., Tadtong, S., & Puthongking, P. (2012). Neuritogenic and antioxidant activities of nordentatin from Clausena harmandiana. Journal of Asian Association of Schools of Pharmacy, 1(3), 180–186. https://www.aaspjournal.org/uploads/155/5952_pdf.pdf
Jantamart, P., Weerapreeyakul, N., & Puthongking, P. (2019). Cytotoxicity and apoptosis induction of coumarins and carbazole alkaloids from Clausena harmandiana. Molecules, 24(18), 1–14. https://doi.org/10.3390/molecules24183385
Kryger, G., Silman, I., & Sussman, J. L. (1999). Structure of acetylcholinesterase complexed with E2020 (Aricept ρ): Implications for the design of new anti-Alzheimer drugs. Structure, 7(3), 297–307. https://doi.org/10.1016/s0969-2126(99)80040-9
Mashhadi, H. R., Shanechi, H. M., & Lucas, C. (2003). A new genetic algorithm with Lamarckian individual learning for generation scheduling. IEEE Transactions on Power Systems, 18(3), 1181–1186. doi: 10.1109/TPWRS.2003.814888.
Metropolis, N., Rosenbluth, A.W., Rosenbluth, M.N., Teller, A.H., & Teller, E. (1953). Equation of state calculations by fast computing machines. The Journal of Chemical Physics, 21(6), 1087–1092. https://doi.org/10.1063/1.1699114
Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A.J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785-2791. https://doi.org/10.1002/jcc.21256
O'Boyle, N. M., Banck, M., James, C. A., Morley, C., Vandermeersch, T., & Hutchison, G. R. (2011). Open Babel: An open chemical toolbox. Journal of Cheminformatics, 3(33), 1-14. https://doi.org/10.1186/1758-2946-3-33
Razavi, S. F., Khoobi, M., Nadri, H., Sakhteman, A., Moradi, A., Emami, S., …, & Shafiee, A. (2013). Synthesis and evaluation of 4-substituted coumarins as novel acetylcholinesterase inhibitors. European Journal of Medicinal Chemistry, 64, 252–259. doi: 10.1016/j.ejmech.2013.03.021.
Rehman, F.U., Khan, M. F., Khan, I., & Roohullah, -. (2013). Molecular interactions of an alkaloid euchrestifoline as a new acetylcholinesterase inhibitor. Bangladesh Journal of Pharmacology, 8(4), 361–364. https://doi.org/10.3329/bjp.v8i4.16417
Sanner, M. F. (1999). Python: A programming language for software integration and development. Journal of Molecular Graphics and Modelling, 17(1), 57–61. http://mgl.scripps.edu/people/sanner/html/papers/NewsAndViewsSept99.pdf
Songsiang, U., Thongthoom, T., Boonyarat, C., & Yenjai, C. (2011). Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana. Journal of Natural Products, 74(2), 208–212. https://doi.org/10.1021/np100654m
Taha, M. O., Habash, M., Al-Hadidi, Z., Al-Bakri, A., Younis, K., & Sisan, S. (2011). Docking-based comparative intermolecular contacts analysis as new 3-D QSAR concept for validating docking studies and in silico screening: NMT and GP inhibitors as case studies. Journal of Chemical Information and Modeling, 51(3), 647–669. https://doi.org/10.1021/ci100368t
Wangboonskul, J., Tunsirikongkon, A., & Sasithornwetchakun, W. (2015). Simultaneous determination of nine analytes in Clausena harmandiana Pierre. by new developed high-performance liquid chromatography method and the influence of locations in Thailand on level of nordentatin and dentatin. Pharmacognosy Magazine, 11(41), 1-14. https://doi.org/10.4103/0973-1296.149666
Wiesner, J., Kříz, Z., Kuca, K., Jun, D., & Koca, J. (2007). Acetylcholinesterases-The structural similarities and differences. Journal of Enzyme Inhibition and Medicinal Chemistry, 22(4), 417–424. doi: 10.1080/14756360701421294
World Health Organization (WHO). (2018). Top 10 causes of death. Retrieved June 5, 2019, from https://www.who.int/gho/mortality_burden_disease/causes_death/top_10/en/
