Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico Study
Rhizophoramucronata Lam., a plant with a rich history of traditional use in various cultures, was subjected to chemical investigation, resulting in the isolation of five terpenoids and derivatives. The structures of these compounds, namely, 1,1,5,7-tetramethyl-4,5-dihydroacenaphthylen-3(1H)-one (1),...
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2024-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/joch/8884812 |
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| author | Punam Sourav Das Sania Ashrafi Juhaer Anjum Md. Emdad Hossain Md. Selim Reza Monira Ahsan |
| author_facet | Punam Sourav Das Sania Ashrafi Juhaer Anjum Md. Emdad Hossain Md. Selim Reza Monira Ahsan |
| author_sort | Punam Sourav Das |
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| description | Rhizophoramucronata Lam., a plant with a rich history of traditional use in various cultures, was subjected to chemical investigation, resulting in the isolation of five terpenoids and derivatives. The structures of these compounds, namely, 1,1,5,7-tetramethyl-4,5-dihydroacenaphthylen-3(1H)-one (1), 3β-hydroxy-11-oxo-olean-12 enyl palmitate (2), taraxerol (3), 3-(Z)-coumaroyltaraxerol (4), and 3β-(E)-coumaroyltaraxerol (5), were elucidated through extensive NMR spectroscopic analysis like 1H NMR, 13C NMR, COSY, HSQC, and HMBC, as well as comparison with those of similar compounds described in the literature. These phytochemicals were subjected to computational assessment through molecular docking against superoxide dismutase (SOD), glutathione peroxidase (GPX), catalase (CAT), cyclooxygenase-2 (COX-2), epidermal growth factor receptor (EGFR), and cyclin-dependent kinase 2 (CDK-2), in addition to ADME/T analyses. Molecular dynamics (MD) simulation was conducted for the compounds showing highest binding affinity toward respective receptor. Different fractions of the crude methanol (MeOH) extract were evaluated for their antioxidant, cytotoxicity, thrombolytic, and anti-inflammatory activities. The ethyl acetate soluble fraction (RME) exhibited the highest DPPH free radical scavenging activity, with an IC50 value of 1.73 μg/mL, compared to the standard (1.68 μg/mL). In the brine shrimp lethality cytotoxicity, the chloroform soluble fraction (RMC) and RME demonstrated substantial lethality, with LC50 values of 0.95 and 1.17 μg/mL, respectively, in comparison to the standard (0.35 μg/mL). Furthermore, the petroleum ether soluble fraction (RMP) and RME displayed substantial activity in the thrombolytic assay, with 86.12% and 73.12% clot lysis, respectively (p<0.001), compared to the standard (97.11%). In the membrane stabilizing assay, the RMC and RME exhibited significant inhibition of hypotonic solution and heat-induced hemolysis. The isolated compounds demonstrated impressive binding scores when interacting with SOD, GPX, CAT, and EGFR receptors. However, their performance was notably lacking when it came to binding with COX-2 and CDK-2 receptors. |
| format | Article |
| id | doaj-art-b864a3f5ada04f129fe8a61d05d43b45 |
| institution | Kabale University |
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| language | English |
| publishDate | 2024-01-01 |
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| spelling | doaj-art-b864a3f5ada04f129fe8a61d05d43b452024-12-27T00:00:11ZengWileyJournal of Chemistry2090-90712024-01-01202410.1155/joch/8884812Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico StudyPunam Sourav Das0Sania Ashrafi1Juhaer Anjum2Md. Emdad Hossain3Md. Selim Reza4Monira Ahsan5Department of Pharmaceutical ChemistryDepartment of Pharmaceutical ChemistryDepartment of Pharmaceutical ChemistryWazed Miah Science Research Centre (WMSRC)Department of Pharmaceutical TechnologyDepartment of Pharmaceutical ChemistryRhizophoramucronata Lam., a plant with a rich history of traditional use in various cultures, was subjected to chemical investigation, resulting in the isolation of five terpenoids and derivatives. The structures of these compounds, namely, 1,1,5,7-tetramethyl-4,5-dihydroacenaphthylen-3(1H)-one (1), 3β-hydroxy-11-oxo-olean-12 enyl palmitate (2), taraxerol (3), 3-(Z)-coumaroyltaraxerol (4), and 3β-(E)-coumaroyltaraxerol (5), were elucidated through extensive NMR spectroscopic analysis like 1H NMR, 13C NMR, COSY, HSQC, and HMBC, as well as comparison with those of similar compounds described in the literature. These phytochemicals were subjected to computational assessment through molecular docking against superoxide dismutase (SOD), glutathione peroxidase (GPX), catalase (CAT), cyclooxygenase-2 (COX-2), epidermal growth factor receptor (EGFR), and cyclin-dependent kinase 2 (CDK-2), in addition to ADME/T analyses. Molecular dynamics (MD) simulation was conducted for the compounds showing highest binding affinity toward respective receptor. Different fractions of the crude methanol (MeOH) extract were evaluated for their antioxidant, cytotoxicity, thrombolytic, and anti-inflammatory activities. The ethyl acetate soluble fraction (RME) exhibited the highest DPPH free radical scavenging activity, with an IC50 value of 1.73 μg/mL, compared to the standard (1.68 μg/mL). In the brine shrimp lethality cytotoxicity, the chloroform soluble fraction (RMC) and RME demonstrated substantial lethality, with LC50 values of 0.95 and 1.17 μg/mL, respectively, in comparison to the standard (0.35 μg/mL). Furthermore, the petroleum ether soluble fraction (RMP) and RME displayed substantial activity in the thrombolytic assay, with 86.12% and 73.12% clot lysis, respectively (p<0.001), compared to the standard (97.11%). In the membrane stabilizing assay, the RMC and RME exhibited significant inhibition of hypotonic solution and heat-induced hemolysis. The isolated compounds demonstrated impressive binding scores when interacting with SOD, GPX, CAT, and EGFR receptors. However, their performance was notably lacking when it came to binding with COX-2 and CDK-2 receptors.http://dx.doi.org/10.1155/joch/8884812 |
| spellingShingle | Punam Sourav Das Sania Ashrafi Juhaer Anjum Md. Emdad Hossain Md. Selim Reza Monira Ahsan Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico Study Journal of Chemistry |
| title | Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico Study |
| title_full | Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico Study |
| title_fullStr | Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico Study |
| title_full_unstemmed | Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico Study |
| title_short | Isolation of Terpenoids and Derivatives From a Bangladeshi Mangrove Plant, Rhizophora mucronata Lam., and Its Bioactivity Evaluation: In Vitro and In Silico Study |
| title_sort | isolation of terpenoids and derivatives from a bangladeshi mangrove plant rhizophora mucronata lam and its bioactivity evaluation in vitro and in silico study |
| url | http://dx.doi.org/10.1155/joch/8884812 |
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