In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata Schrenk
A biologically guided isolation of secondary metabolites from Cousinia alata Schrenk wild plant growing in Akmola region, Kazakhstan, led to the isolation of the bioactive diterpene grindelic acid (1). Six flavonoids were also isolated and identified as retusine (2), pachipodol (3), jaranol (4), pen...
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| Format: | Article |
| Language: | English |
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Wiley
2021-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2021/5542455 |
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| author | Almira Zhanzhaxina Yerlan Suleimen Ahmed M. Metwaly Ibrahim H. Eissa Eslam B. Elkaeed Raigul Suleimen Margarita Ishmuratova Kydyrmolla Akatan Walter Luyten |
| author_facet | Almira Zhanzhaxina Yerlan Suleimen Ahmed M. Metwaly Ibrahim H. Eissa Eslam B. Elkaeed Raigul Suleimen Margarita Ishmuratova Kydyrmolla Akatan Walter Luyten |
| author_sort | Almira Zhanzhaxina |
| collection | DOAJ |
| description | A biologically guided isolation of secondary metabolites from Cousinia alata Schrenk wild plant growing in Akmola region, Kazakhstan, led to the isolation of the bioactive diterpene grindelic acid (1). Six flavonoids were also isolated and identified as retusine (2), pachipodol (3), jaranol (4), penduletin (5), casticin (6), and 5, 7, 3′-trihydroxy-3, 4′-dimethoxyflavone (7). Penduletin (5) showed moderate cytotoxic activity assay. Grindelic acid exhibited promising cytotoxic activity against the Artemia salina nauplii and antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Salmonella enteritidis. The presence of the essential pharmacophoric features of histone deacetylase (HDAC) inhibitors in the structure of grindelic acid encouraged us to run a molecular docking study against the HDAC enzyme to understand its mechanism of action on a molecular level. Grindelic acid showed a binding mode of interaction similar to that of the cocrystallized ligand and exhibited good binding affinity against HDAC with the binding free energy of −18.70 kcal/mol. The structures of isolated compounds were determined by MS, 1D, and 2D NMR spectroscopy methods. Compounds (1–7) were isolated for the first time from Cousinia genus. |
| format | Article |
| id | doaj-art-f9d88a7115a94a108cd870f50dff4968 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2021-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-f9d88a7115a94a108cd870f50dff49682025-02-03T06:46:10ZengWileyJournal of Chemistry2090-90632090-90712021-01-01202110.1155/2021/55424555542455In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata SchrenkAlmira Zhanzhaxina0Yerlan Suleimen1Ahmed M. Metwaly2Ibrahim H. Eissa3Eslam B. Elkaeed4Raigul Suleimen5Margarita Ishmuratova6Kydyrmolla Akatan7Walter Luyten8L.N. Gumilyov Eurasian National University, Nur-Sultan, KazakhstanSh. Ualikhanov Kokshetau University, Kokshetau, KazakhstanPharmacognosy and Medicinal Plants Department, Faculty of Pharmacy, Al-Azhar University, Cairo, EgyptPharmaceutical Medicinal Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, EgyptDepartment of Pharmaceutical Sciences, College of Pharmacy, AlMaarefa University, Ad Diriyah, Riyadh 13713, Saudi ArabiaL.N. Gumilyov Eurasian National University, Nur-Sultan, KazakhstanE.A. Buketov Karaganda University, Karaganda, KazakhstanS. Amanzholov East Kazakhstan State University, Oskemen, KazakhstanDepartment of Biology, Katholieke Universiteit Leuven, Leuven 3000, BelgiumA biologically guided isolation of secondary metabolites from Cousinia alata Schrenk wild plant growing in Akmola region, Kazakhstan, led to the isolation of the bioactive diterpene grindelic acid (1). Six flavonoids were also isolated and identified as retusine (2), pachipodol (3), jaranol (4), penduletin (5), casticin (6), and 5, 7, 3′-trihydroxy-3, 4′-dimethoxyflavone (7). Penduletin (5) showed moderate cytotoxic activity assay. Grindelic acid exhibited promising cytotoxic activity against the Artemia salina nauplii and antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Salmonella enteritidis. The presence of the essential pharmacophoric features of histone deacetylase (HDAC) inhibitors in the structure of grindelic acid encouraged us to run a molecular docking study against the HDAC enzyme to understand its mechanism of action on a molecular level. Grindelic acid showed a binding mode of interaction similar to that of the cocrystallized ligand and exhibited good binding affinity against HDAC with the binding free energy of −18.70 kcal/mol. The structures of isolated compounds were determined by MS, 1D, and 2D NMR spectroscopy methods. Compounds (1–7) were isolated for the first time from Cousinia genus.http://dx.doi.org/10.1155/2021/5542455 |
| spellingShingle | Almira Zhanzhaxina Yerlan Suleimen Ahmed M. Metwaly Ibrahim H. Eissa Eslam B. Elkaeed Raigul Suleimen Margarita Ishmuratova Kydyrmolla Akatan Walter Luyten In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata Schrenk Journal of Chemistry |
| title | In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata Schrenk |
| title_full | In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata Schrenk |
| title_fullStr | In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata Schrenk |
| title_full_unstemmed | In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata Schrenk |
| title_short | In Vitro and In Silico Cytotoxic and Antibacterial Activities of a Diterpene from Cousinia alata Schrenk |
| title_sort | in vitro and in silico cytotoxic and antibacterial activities of a diterpene from cousinia alata schrenk |
| url | http://dx.doi.org/10.1155/2021/5542455 |
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