Ghani, Muhammad Solehin Abd and Abu Bakar, Nur Ain Latifhaa and Ramadani, Arba Pramundita and Nugraha, Arde Toga and Awang, Khalijah and Omar, Mohammad Tasyriq Che and Supratman, Unang and Kamarulzaman, Ezatul Ezleen and Taib, Mohamad Nurul Azmi Mohamad (2024) Hemisynthesis of Pentacyclic Triterpenoids from Diospyros foxworthyi with In vitro and In silico Anti-malarial Evaluation. Current Organic Chemistry, 28 (10). pp. 799-814. ISSN 1385-2728, DOI https://doi.org/10.2174/0113852728294047240315063815.
Full text not available from this repository.Abstract
A total of twelve pentacyclic triterpenoid derivatives based on betulin (1) and lupeol (2) scaffolds isolated from Diospyros foxworthyi were hemisynthesized by acylation or acetylation reactions with appropriate acid chloride or acetic anhydride. The structures of the hemisynthesised compounds were characterised by means of FT-IR, 1D- and 2D-NMR, as well as HRMS analysis. These compounds were assayed for in vitro anti-malarial studies by inhibition of beta-hematin formation assay with chloroquine as a positive control. Compounds 1d and 2f showed the strongest potential as beta-hematin formation inhibitors with IC50 values of 6.66 +/- 1.36 and 11.89 +/- 0.15 mu M, respectively, compared with the positive control (chloroquine; IC50 = 37.50 +/- 0.60 mu M). In silico molecular docking simulations were performed using AutoDock Vina for compounds 1d and 2f to investigate the binding interactions and free energy of binding (FEB) with the hemozoin supercell crystal structure (CCDC number: XETXUP01). The findings revealed several hydrophobic interaction modes between the 1d, 2f and hemozoin, with calculated FEBs of -8.4 +/- 0.2 and -8.9 +/- 0.0 kcal mol(-1), indicating strong and favourable interactions.
| Item Type: | Article |
|---|---|
| Funders: | Graduate Excellence Programme (GrEP) MARA |
| Uncontrolled Keywords: | Pentacyclic triterpenoids; hemisynthesis; anti-malaria; beta-hematin inhibition activity; molecular docking; Diospyros foxworthyi |
| Subjects: | Q Science > Q Science (General) Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 22 Nov 2024 01:32 |
| Last Modified: | 22 Nov 2024 01:32 |
| URI: | http://eprints.um.edu.my/id/eprint/47083 |
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