Identification of potential inhibitors of SARS-CoV-2 from Artemisia annua compounds by In silico evaluation and their density functional theory (DFT)
Abstract
The genus Artemisia has recognized medicinal value and its use by humans Dates back to centuries ago. With the appearance of the new coronavirus, end of 2019, several countries have recommended the use of herbal teas consisting mainly of Artemisia. The individual analysis of the constituents of this species is crucial to characterize and optimize its antiSARS-Cov-2 action. We evaluated by molecular docking the inhibitory action of major compounds of the Artemisia genus (Artemisinin, Arteannuin B, Alpha Thujone, P-Hydroxyacetophenone, Fisetin, Cirsimaritin, Capillin, β-Sitosterol, and Quercetin) against three targets namely SARS-CoV-2 main protease (Mp), SARS-CoV-2 receptor binding domain (RBD) and human furin protease (HF protease). The two flavonols, quercetin and fisetin, have the best binding energies with the three targets. Quercetin/Fisetin possesses binding energy of -7.17/-6.9, -6.3/-6.15 and – 5.98/- 5.49 kcal/mol with MP, RBD and HF protease respectively. Their physicochemical properties meet the requirements of an oral active principle and are not toxic according to predictive simulations. Thereby DFT calculation has been used to analyze the electronic and geometric characteristics of these two compounds. The gap energies were also deduced for the stable structure and their reactivity. The abundance of Quercetin in different plants may be another advantage in the use of this bio-compound in the treatment of coronavirus.
Keywords: Artemisia annua, DFT, Docking Molecular, SARS-Cov-2, Quercetin and Fisetin
Keywords:
Artemisia annua, DFT, Docking Molecular, SARS-Cov-2, Quercetin, Fisetin
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References
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[2] M. Iranshahi, S. A. Emami, et M. Mahmoud-Soltani, « Detection of Sesquiterpene Lactones in Ten Artemisia Species Population of Khorasan Provinces », Iranian Journal of Basic Medical Sciences, vol. 10, no 3, p. 183‑188, juill. 2007, doi: 10.22038/ijbms.2007.5293.
[3] S.-P. He et al., « Development of a sensitive monoclonalantibody-based enzyme-linked immunosorbent assay for the antimalaria active ingredient artemisinin in the Chinese herb Artemisia annua L. », Anal Bioanal Chem, vol. 393, no 4, p. 1297‑1303, févr. 2009, doi: 10.1007/s00216-008-2527-5.
[4] D. S. Bhakuni, A. K. Goel, A. K. Goel, S. Jain, B. N. Mehrotra, et R. C. Srimal, « Screening of Indian plants for biological activity: Part XIV », Indian Journal of Experimental Biology, avr. 14, 1990. https://eurekamag.com/research/007/771/007771446.php (consulté le oct. 18, 2020).
[5] Z. X. Wei, J. P. Pan, et Y. Li, « Artemisinin G: A Sesquiterpene from Artemisia annua », Planta Med, vol. 58, no 3, p. 300, juin 1992, doi: 10.1055/s-2006-961470.
[6] X. Han, X. Ma, T. Zhang, Y. Zhang, Q. Liu, et Y. Ito, « Isolation of high-purity casticin from Artemisia annua L. by high-speed counter-current chromatography », Journal of Chromatography A, vol. 1151, no 1, p. 180‑182, juin 2007, doi: 10.1016/j.chroma.2007.02.105.
[7] J. Han, M. Ye, X. Qiao, M. Xu, B. Wang, et D.-A. Guo, « Characterization of phenolic compounds in the Chinese herbal drug Artemisia annua by liquid chromatography coupled to electrospray ionization mass spectrometry », Journal of Pharmaceutical and Biomedical Analysis, vol. 47, no 3, p. 516‑525, juill. 2008, doi: 10.1016/j.jpba.2008.02.013.
[8] N. Q. Liu, F. Van der Kooy, et R. Verpoorte, « Artemisia afra: A potential flagship for African medicinal plants? », South African Journal of Botany, vol. 75, no 2, p. 185‑195, avr. 2009, doi: 10.1016/j.sajb.2008.11.001.
[9] M. M. Abid Ali Khan, D. C. Jain, R. S. Bhakuni, Mohd. Zaim, et R. S. Thakur, « Occurrence of some antiviral sterols in Artemisia annua », Plant Science, vol. 75, no 2, p. 161‑165, janv. 1991, doi: 10.1016/0168-9452(91)90230-6.
[10] X. Sun et G. R. Whittaker, « Role for influenza virus envelope cholesterol in virus entry and infection », J Virol, vol. 77, no 23, p. 12543‑12551, déc. 2003, doi: 10.1128/jvi.77.23.12543-12551.2003.
[11] J. F. S. Ferreira, D. L. Luthria, T. Sasaki, et A. Heyerick, « Flavonoids from Artemisia annua L. as antioxidants and their potential synergism with artemisinin against malaria and cancer », Molecules, vol. 15, no 5, p. 3135‑3170, avr. 2010, doi: 10.3390/molecules15053135.
[12] S. Li et al., « Identification of natural compounds with antiviral activities against SARS-associated coronavirus », Antiviral Research, vol. 67, no 1, p. 18‑23, juill. 2005, doi: 10.1016/j.antiviral.2005.02.007.
[13] S. PENG, « Syndrome Differentiation and Treatment Administration of SARS ». http://caod.oriprobe.com/articles/6268544/Syndrome_Differentiation_and_Treatment_Administration_of_SARS.htm (consulté le oct. 18, 2020).
[14] R. Dong, X. Xiong, et G. Chen, « Discuss about the application of Artemisia annua prescriptions in the treatment of COVID-19 », TMR Modern Herbal Medicine, vol. 3, no 1‑7, p. 7, 2020.
[15] A. C. Walls, Y.-J. Park, M. A. Tortorici, A. Wall, A. T. McGuire, et D. Veesler, « Structure, Function, and Antigenicity of the SARS-CoV-2 Spike Glycoprotein », Cell, vol. 181, no 2, p. 281-292.e6, avr. 2020, doi: 10.1016/j.cell.2020.02.058.
[16] M. Nigam et al., « Bioactive Compounds and Health Benefits of Artemisia Species », Natural Product Communications, vol. 14, no 7, p. 1934578X1985035, juill. 2019, doi: 10.1177/1934578X19850354.
[17] Z. Xu et al., « Nelfinavir was predicted to be a potential inhibitor of 2019-nCov main protease by an integrative approach combining homology modelling, molecular docking and binding free energy calculation », Pharmacology and Toxicology, preprint, janv. 2020. doi: 10.1101/2020.01.27.921627.
[18] A. Elmi, S. A.-J. Sayem, M. Ahmed, et F. Abdoul-Latif, « NATURAL COMPOUNDS FROM DJIBOUTIAN MEDICINAL PLANTS AS INHIBITORS OF COVID-19 BY IN SILICO INVESTIGATIONS », Int J Curr Pharm Sci, p. 52‑57, juill. 2020, doi: 10.22159/ijcpr.2020v12i4.39051.
[19] G. A. Petersson, A. Bennett, T. G. Tensfeldt, M. A. Al‐Laham, W. A. Shirley, et J. Mantzaris, « A complete basis set model chemistry. I. The total energies of closed‐shell atoms and hydrides of the first‐row elements », J. Chem. Phys., vol. 89, no 4, p. 2193‑2218, août 1988, doi: 10.1063/1.455064.
[20] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M.A. Robb, R. Cheeseman, J. Montgomer, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. et A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W.Wong, C. Gonzalez, J.A. Pople, « Gaussian 03 », 2004.
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ELMI A, MOHAMED AS, SIDDIQUI N, AL JAWAD S, Nour M, MIGANEH I, JAVED S. Identification of potential inhibitors of SARS-CoV-2 from Artemisia annua compounds by In silico evaluation and their density functional theory (DFT). JDDT [Internet]. 15Feb.2021 [cited 4Mar.2021];11(1-s):71-2. Available from: http://jddtonline.info/index.php/jddt/article/view/4702
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