Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i>
A new dicoumarin, jusan coumarin, (<b>1</b>), has been isolated from <i>Artemisia glauca</i> aerial parts. The chemical structure of jusan coumarin was estimated, by 1D, 2D NMR as well as HR-Ms spectroscopic methods, to be 7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-6-yl)oxy]-2H...
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| Format: | Article |
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MDPI AG
2022-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/7/2281 |
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| author | Yerlan M. Suleimen Rani A. Jose Raigul N. Suleimen Margarita Y. Ishmuratova Suzanne Toppet Wim Dehaen Aisha A. Alsfouk Eslam B. Elkaeed Ibrahim H. Eissa Ahmed M. Metwaly |
| author_facet | Yerlan M. Suleimen Rani A. Jose Raigul N. Suleimen Margarita Y. Ishmuratova Suzanne Toppet Wim Dehaen Aisha A. Alsfouk Eslam B. Elkaeed Ibrahim H. Eissa Ahmed M. Metwaly |
| author_sort | Yerlan M. Suleimen |
| collection | DOAJ |
| description | A new dicoumarin, jusan coumarin, (<b>1</b>), has been isolated from <i>Artemisia glauca</i> aerial parts. The chemical structure of jusan coumarin was estimated, by 1D, 2D NMR as well as HR-Ms spectroscopic methods, to be 7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-6-yl)oxy]-2H-chromen-2-one. As the first time to be introduced in nature, its potential against SARS-CoV-2 has been estimated using various in silico methods. Molecular similarity and fingerprints experiments have been utilized for <b>1</b> against nine co-crystallized ligands of COVID-19 vital proteins. The results declared a great similarity between Jusan Coumarin and <b>X77</b>, the ligand of COVID-19 main protease (PDB ID: 6W63), M<sup>pro</sup>. To authenticate the obtained outputs, a DFT experiment was achieved to confirm the similarity of <b>X77</b> and <b>1</b>. Consequently, <b>1</b> was docked against M<sup>pro</sup>. The results clarified that <b>1</b> bonded in a correct way inside M<sup>pro</sup> active site, with a binding energy of −18.45 kcal/mol. Furthermore, the ADMET and toxicity profiles of <b>1</b> were evaluated and showed the safety of <b>1</b> and its likeness to be a drug. Finally, to confirm the binding and understand the thermodynamic characters between <b>1</b> and M<sup>pro</sup>, several molecular dynamics (MD) simulations studies have been administered. Additionally, the known coumarin derivative, 7-isopentenyloxycoumarin (<b>2</b>), has been isolated as well as β-sitosterol (<b>3</b>). |
| first_indexed | 2024-03-09T11:35:49Z |
| format | Article |
| id | doaj.art-5557cd761c814d019ff433e5c1de3552 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:35:49Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5557cd761c814d019ff433e5c1de35522023-11-30T23:42:04ZengMDPI AGMolecules1420-30492022-03-01277228110.3390/molecules27072281Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i>Yerlan M. Suleimen0Rani A. Jose1Raigul N. Suleimen2Margarita Y. Ishmuratova3Suzanne Toppet4Wim Dehaen5Aisha A. Alsfouk6Eslam B. Elkaeed7Ibrahim H. Eissa8Ahmed M. Metwaly9The International Centre for Interdisciplinary Solutions on Antibiotics and Secondary Metabolites, Republican Collection of Microorganisms, Nur-Sultan 010000, KazakhstanMolecular Design & Synthesis, Department of Chemistry, Catholic University of Leuven, B-3001 Leuven, BelgiumDepartment of Technical Physics, Faculty of Physics and Technology, L.N. Gumilyov Eurasian National University, Nur-Sultan 010010, KazakhstanDepartment of Botany, E.A. Buketov Karaganda University, Karaganda 100024, KazakhstanMolecular Design & Synthesis, Department of Chemistry, Catholic University of Leuven, B-3001 Leuven, BelgiumMolecular Design & Synthesis, Department of Chemistry, Catholic University of Leuven, B-3001 Leuven, BelgiumDepartment of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Pharmacy, AlMaarefa University, Riyadh 13713, Saudi ArabiaPharmaceutical Medicinal Chemistry & Drug Design Department, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo 11884, EgyptPharmacognosy and Medicinal Plants Department, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo 11884, EgyptA new dicoumarin, jusan coumarin, (<b>1</b>), has been isolated from <i>Artemisia glauca</i> aerial parts. The chemical structure of jusan coumarin was estimated, by 1D, 2D NMR as well as HR-Ms spectroscopic methods, to be 7-hydroxy-6-methoxy-3-[(2-oxo-2H-chromen-6-yl)oxy]-2H-chromen-2-one. As the first time to be introduced in nature, its potential against SARS-CoV-2 has been estimated using various in silico methods. Molecular similarity and fingerprints experiments have been utilized for <b>1</b> against nine co-crystallized ligands of COVID-19 vital proteins. The results declared a great similarity between Jusan Coumarin and <b>X77</b>, the ligand of COVID-19 main protease (PDB ID: 6W63), M<sup>pro</sup>. To authenticate the obtained outputs, a DFT experiment was achieved to confirm the similarity of <b>X77</b> and <b>1</b>. Consequently, <b>1</b> was docked against M<sup>pro</sup>. The results clarified that <b>1</b> bonded in a correct way inside M<sup>pro</sup> active site, with a binding energy of −18.45 kcal/mol. Furthermore, the ADMET and toxicity profiles of <b>1</b> were evaluated and showed the safety of <b>1</b> and its likeness to be a drug. Finally, to confirm the binding and understand the thermodynamic characters between <b>1</b> and M<sup>pro</sup>, several molecular dynamics (MD) simulations studies have been administered. Additionally, the known coumarin derivative, 7-isopentenyloxycoumarin (<b>2</b>), has been isolated as well as β-sitosterol (<b>3</b>).https://www.mdpi.com/1420-3049/27/7/2281<i>Artemisia glauca</i>jusan coumarinnew dicoumarinCOVID-19 main proteasemolecular similaritystructure fingerprint |
| spellingShingle | Yerlan M. Suleimen Rani A. Jose Raigul N. Suleimen Margarita Y. Ishmuratova Suzanne Toppet Wim Dehaen Aisha A. Alsfouk Eslam B. Elkaeed Ibrahim H. Eissa Ahmed M. Metwaly Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i> Molecules <i>Artemisia glauca</i> jusan coumarin new dicoumarin COVID-19 main protease molecular similarity structure fingerprint |
| title | Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i> |
| title_full | Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i> |
| title_fullStr | Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i> |
| title_full_unstemmed | Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i> |
| title_short | Isolation and In Silico SARS-CoV-2 Main Protease Inhibition Potential of Jusan Coumarin, a New Dicoumarin from <i>Artemisia glauca</i> |
| title_sort | isolation and in silico sars cov 2 main protease inhibition potential of jusan coumarin a new dicoumarin from i artemisia glauca i |
| topic | <i>Artemisia glauca</i> jusan coumarin new dicoumarin COVID-19 main protease molecular similarity structure fingerprint |
| url | https://www.mdpi.com/1420-3049/27/7/2281 |
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