Acetylcholinesterase Inhibition Activity of Ethanolic Extract of Sesbania javanica Miq. Flowers
Keywords:
Alzheimer’s disease, Sesbania javanica Miq, Fabaceae, Acetylcholinesterase activityAbstract
Cholinergic signaling impairment in Alzheimer’s disease (AD) is associated with a low level of acetylcholine as a result of acetylcholinesterase hydrolysis. Acetylcholinesterase inhibitors are found in numerous plants and phytoconstituents. This study aims to investigate the effect of Sesbania javanica Miq. flower extracts on anti-acetylcholinesterase activity and identify its potential compounds. The ethanolic extracts of Sesbania javanica Miq. flowers showed a relatively high percentage of acetylcholinesterase inhibitory activity in a dose-dependent manner (IC50 = 18.56±1.67 mg/mL). However, physostigmine (reference standard) shows the highest potency of acetylcholinesterase inhibition compared to the extracts, IC50 < 0.005 mg/mL. Gas chromatography-mass spectrometry-based analysis revealed that the ethanolic extract of the flower contained major phytochemicals including thiophene and 1-(5-Bicyclo[2.2.1]heptyl)ethylamine, which are predicted to penetrate across the blood-brain barrier. Thiophene was found to be the most abundant compound of the extract. The molecular docking demonstrated that the active phytochemical 1-(5-Bicyclo[2.2.1]heptyl)ethylamine forms hydrogen bonds with the active site of acetylcholinesterase, exhibiting the same orientation as physostigmine, thereby conferring anti-cholinesterase activity. Our findings suggest that the flower extract of Sesbania javanica Miq. (Fabaceae) may provide new phytochemicals for potential drug discovery as inhibitors of acetylcholinesterase activity.
References
Blanpied, T.A., Clarke, R.J., & Johnson, J.W. (2005). Amantadine inhibits NMDA receptors by accelerating channel closure during channel block. The Journal of Neuroscience, 25(13), 3312-3322.
Bloom, G.S. (2014). Amyloid-β and tau: The trigger and bullet in alzheimer disease pathogenesis. JAMA Neurology, 71(4), 505-508.
Boison, D. (2007). Acetylcholinesterase. In S.J. Enna & D.B. Bylund (Eds.), xPharm: The Comprehensive Pharmacology Reference (pp. 1 8.). New York: Elsevier.
Bunma, S., & Balslev, H. (2019). A Review of the economic botany of Sesbania (Leguminosae). Botanical Review, 85(3), 185-251.
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(22), 10282-10286.
Cummings, J., Lee, G., Ritter, A., Sabbagh, M., & Zhong, K. (2019). Alzheimer's disease drug development pipeline: 2019. Alzheimer's Dementia (New York, N.Y.), 5, 272-293.
Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7(1), 42717.
Fatima, I., Safdar, N., Akhtar, W., Munir, A., Saqib, S., Ayaz, A., . . . Zaman, W. (2023). Evaluation of potential inhibitory effects on acetylcholinesterase, pancreatic lipase, and cancer cell lines using raw leaves extracts of three fabaceae species. Heliyon, 9(5), e15909.
Filimonov, D.A., Lagunin, A., Gloriozova, T., Rudik, A.V., Druzhilovskii, D.S., Pogodin, P., & Poroikov, V. (2014). Prediction of the biological activity spectra of organic compounds using the pass online web resource. Chemistry of Heterocyclic Compounds, 50, 444-457.
Gulisano, W., Maugeri, D., Baltrons, M.A., Fà, M., Amato, A., Palmeri, A., . . . Arancio, O. (2018). Role of amyloid-β and Tau proteins in alzheimer's disease: confuting the amyloid cascade. Journal of Alzheimer's Disease, 64(s1), S611-s631.
Hasselmo, M.E. (2006). The role of acetylcholine in learning and memory. Current Opinion in Neurobiology, 16(6), 710-715.
Honour, J.W. (2006). Gas chromatography-mass spectrometry. Methods in Molecular Biology, 324, 53-74.
Ismail, M.M., Kamel, M.M., Mohamed, L.W., Faggal, S.I., & Galal, M.A. (2012). Synthesis and biological evaluation of thiophene derivatives as acetylcholinesterase inhibitors. Molecules, 17(6), 7217-7231.
Kijparkorn, S., Plaimast, H., & Wangsoonoen, S. (2010). Sano (Sesbania javanica Miq.) Flower as a pigment source in egg yolk of laying hens. The Thai Journal of Veterinary Medicine, 40(3), 281-287.
Kim, S., Chen, J., Cheng, T., Gindulyte, A., He, J., He, S., . . . Bolton, E.E. (2021). PubChem in 2021: New data content and improved web interfaces. Nucleic Acids Research, 49(D1), D1388-d1395.
Lekdee, T., Anupan, S., & Phongkaew, S. (2023). The phytochemical screening and antioxidant activity of Sesbania javanica L. flower extract. Koch Cha Sarn Journal of Science, 45(2), 1-7.
Lesné, S. E., Sherman, M. A., Grant, M., Kuskowski, M., Schneider, J. A., Bennett, D. A., & Ashe, K.H. (2013). Brain amyloid-β oligomers in ageing and alzheimer's disease. Brain, 136(Pt 5), 1383-1398.
Loedsaksaesakul, U. (2007). Characterization and biological activity of compounds from flowers and leaves of Sesbania javanica Miq. (Doctoral dissertation). Silpakorn University, Thailand: Silpakorn University.
Mangmool, S., Kunpukpong, I., Kitphati, W., & Anantachoke, N. (2021). Antioxidant and anticholinesterase activities of extracts and phytochemicals of Syzygium antisepticum leaves. Molecules, 26(11), 3295.
McHardy, S.F., Wang, H.L., McCowen, S.V., & Valdez, M.C. (2017). Recent advances in acetylcholinesterase Inhibitors and reactivators: An update on the patent literature (2012-2015). Expert Opinion on Therapeutic Patents, 27(4), 455-476.
Medeiros, P.M. (2018). Gas Chromatography–mass spectrometry (GC–MS). In W.M. White (Ed.), Encyclopedia of Geochemistry: A Comprehensive Reference Source on the Chemistry of the Earth (pp. 530-535). Cham: Springer International Publishing.
Mohammed, R.M.U., Patil, S.B., Shwetal, S., Rajshri. S.P. (2013). Sesbania sesban Linn.: An Overview. 4, 2644-2648.
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.
Mukherjee, P.K., Kumar, V., Mal, M., & Houghton, P.J. (2007). Acetylcholinesterase inhibitors from plants. Phytomedicine, 14(4), 289-300.
Murray, A.P., Faraoni, M.B., Castro, M.J., Alza, N.P., & Cavallaro, V. (2013). Natural AChE inhibitors from plants and their contribution to alzheimer's disease therapy. Current Neuropharmacology, 11(4), 388-413.
Pettersen, E.F., Goddard, T.D., Huang, C.C., Couch, G.S., Greenblatt, D.M., Meng, E.C., & Ferrin, T.E. (2004). UCSF chimera--a visualization system for exploratory research and analysis. Journal of Computational Chemistry, 25(13), 1605-1612.
Pooma, R., & Suddee, S. (2014). Thai plant names tem smitinand revised edition 2014. Bangkok: Office of the Forest Herbarium, Department of National Park, Wildlife and Plant Conservation.
Tangvarasittichai, S., Sriprang, N., Harnroongroj, T., & Changbumrung, S. (2005). Antimutagenic activity of Sesbania javanica Miq. flower DMSO extract and its major flavonoid glycoside. Southeast Asian Journal Tropical Medicine and Public Health, 36(6), 1543-1551.
Taylor, P., Camp, S., & Radić, Z. (2009). Acetylcholinesterase. In L.R. Squire (Ed.), Encyclopedia of Neuroscience (pp. 5-7). Oxford: Academic Press.
Terry, A.V., Jr., & Buccafusco, J J. (2003). The cholinergic hypothesis of age and alzheimer's disease-related cognitive deficits: recent challenges and their implications for novel drug development. Journal of Pharmacology and Experimental Therapeutics, 306(3), 821-827.
Worek, F., Eyer, P., & Thiermann, H. (2012). Determination of acetylcholinesterase activity by the Ellman assay: A versatile tool for in vitro research on medical countermeasures against organophosphate poisoning. Drug Testing and Analysis, 4(3-4), 282-291.
Wyss-Coray, T. (2016). Ageing, neurodegeneration and brain rejuvenation. Nature, 539(7628), 180-186.
Yiannopoulou, K.G., & Papageorgiou, S.G. (2020). Current and future treatments in alzheimer disease: An update. Journal of Central Nervous System Disease, 12, 1179573520907397.
Zhou, X., Wang, X.-B., Wang, T., & Kong, L.-Y. (2008). Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues. Bioorganic and Medicinal Chemistry, 16(17), 8011-8021.
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