Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulations
Natural triterpenes isolated from Euphorbia resinifera latex, α-Euphol and α- Euphorbol, have been subjected to structural modification using oxidative agents such as chromic anhydride (CrO3) and sodium periodate in the presence of ruthenium trichloride NaIO4-(RuCl3, 3H2O) to obtain new triterpene d...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-12-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2667022423002116 |
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| author | Imane Yamari Ayoub Mouhib Bouchra Es-Sounni Rida Nejjari Noureddine Mazoir Mohamed Bakhouch Abdelkrim Mouzdahir Ahmed Benharref M'hammed El Kouali Samir Chtita |
| author_facet | Imane Yamari Ayoub Mouhib Bouchra Es-Sounni Rida Nejjari Noureddine Mazoir Mohamed Bakhouch Abdelkrim Mouzdahir Ahmed Benharref M'hammed El Kouali Samir Chtita |
| author_sort | Imane Yamari |
| collection | DOAJ |
| description | Natural triterpenes isolated from Euphorbia resinifera latex, α-Euphol and α- Euphorbol, have been subjected to structural modification using oxidative agents such as chromic anhydride (CrO3) and sodium periodate in the presence of ruthenium trichloride NaIO4-(RuCl3, 3H2O) to obtain new triterpene derivatives with good yield. The semi-synthesized triterpenes (1–9) and (10–16) prepared from α-Euphol and α-Euphorbol have been tested in silico to predict and evaluate their antibacterial and insecticidal properties. Among the tested compounds, three of them (3, 15, and 16) were discarded after evaluating their drug-likeness and ADME-Tox profiles. Then, a molecular docking analysis was performed to predict which one of the studied compounds could inhibit MurE (PDB ID: 1E8C) and EcR (PDB ID: 1R20) proteins involved in antibacterial and insecticidal activities, respectively. Among the docked compounds, only compounds 8 and 9 showed better stability in the MurE and EcR receptor pocket than the Amoxicillin and 20-Hydroxyecdysone used as standards. After that, molecular dynamics simulation was performed to further investigate the stability of compound 9 in the binding pocket of both targeted receptors. Eventually, the outcomes of this study show that the new triterpene derivative 9 could be used as a promising candidate to develop new insecticides and antibacterial drugs. |
| first_indexed | 2024-03-09T02:01:20Z |
| format | Article |
| id | doaj.art-f141b825f38a45a29b5a2b3cf090c8b0 |
| institution | Directory Open Access Journal |
| issn | 2667-0224 |
| language | English |
| last_indexed | 2024-03-09T02:01:20Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Chemical Physics Impact |
| spelling | doaj.art-f141b825f38a45a29b5a2b3cf090c8b02023-12-08T04:46:49ZengElsevierChemical Physics Impact2667-02242023-12-017100372Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulationsImane Yamari0Ayoub Mouhib1Bouchra Es-Sounni2Rida Nejjari3Noureddine Mazoir4Mohamed Bakhouch5Abdelkrim Mouzdahir6Ahmed Benharref7M'hammed El Kouali8Samir Chtita9Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M'Sik, Hassan II University of Casablanca, P.O. Box 7955, Casablanca, MoroccoBioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, University Chouaib Doukkali, P.O. Box 20, El Jadida 24000, MoroccoLaboratory of Innovative Materials and Biotechnology of Natural Resources, Faculty of Sciences, Moulay Ismail University, P.O. Box 11201, Meknes 50000, MoroccoBioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, University Chouaib Doukkali, P.O. Box 20, El Jadida 24000, MoroccoBioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, University Chouaib Doukkali, P.O. Box 20, El Jadida 24000, Morocco; Corresponding authors.Bioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, University Chouaib Doukkali, P.O. Box 20, El Jadida 24000, MoroccoBioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, University Chouaib Doukkali, P.O. Box 20, El Jadida 24000, MoroccoLaboratory of Natural Substances, Faculty of Sciences Semlalia, Cadi Ayyad University, P.O. Box 2390, Marrakech 40000, MoroccoLaboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M'Sik, Hassan II University of Casablanca, P.O. Box 7955, Casablanca, MoroccoLaboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M'Sik, Hassan II University of Casablanca, P.O. Box 7955, Casablanca, Morocco; Corresponding authors.Natural triterpenes isolated from Euphorbia resinifera latex, α-Euphol and α- Euphorbol, have been subjected to structural modification using oxidative agents such as chromic anhydride (CrO3) and sodium periodate in the presence of ruthenium trichloride NaIO4-(RuCl3, 3H2O) to obtain new triterpene derivatives with good yield. The semi-synthesized triterpenes (1–9) and (10–16) prepared from α-Euphol and α-Euphorbol have been tested in silico to predict and evaluate their antibacterial and insecticidal properties. Among the tested compounds, three of them (3, 15, and 16) were discarded after evaluating their drug-likeness and ADME-Tox profiles. Then, a molecular docking analysis was performed to predict which one of the studied compounds could inhibit MurE (PDB ID: 1E8C) and EcR (PDB ID: 1R20) proteins involved in antibacterial and insecticidal activities, respectively. Among the docked compounds, only compounds 8 and 9 showed better stability in the MurE and EcR receptor pocket than the Amoxicillin and 20-Hydroxyecdysone used as standards. After that, molecular dynamics simulation was performed to further investigate the stability of compound 9 in the binding pocket of both targeted receptors. Eventually, the outcomes of this study show that the new triterpene derivative 9 could be used as a promising candidate to develop new insecticides and antibacterial drugs.http://www.sciencedirect.com/science/article/pii/S2667022423002116Euphorbia resiniferaTriterpenesAntibacterialInsecticideADME-ToxMolecular docking |
| spellingShingle | Imane Yamari Ayoub Mouhib Bouchra Es-Sounni Rida Nejjari Noureddine Mazoir Mohamed Bakhouch Abdelkrim Mouzdahir Ahmed Benharref M'hammed El Kouali Samir Chtita Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulations Chemical Physics Impact Euphorbia resinifera Triterpenes Antibacterial Insecticide ADME-Tox Molecular docking |
| title | Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulations |
| title_full | Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulations |
| title_fullStr | Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulations |
| title_full_unstemmed | Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulations |
| title_short | Oxidative functionalization of triterpenes isolated from Euphorbia resinifera latex: Semisynthesis, ADME-Tox, molecular docking, and molecular dynamics simulations |
| title_sort | oxidative functionalization of triterpenes isolated from euphorbia resinifera latex semisynthesis adme tox molecular docking and molecular dynamics simulations |
| topic | Euphorbia resinifera Triterpenes Antibacterial Insecticide ADME-Tox Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S2667022423002116 |
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