DFT Calculations, Pro-apoptotic effects, Anti-infective Investigations of Alkaloids isolated from the stem bark extract of Enantia chlorantha
Creators
- 1. University of Benin
- 2. Mansoura University
- 3. Al-Azhar University
- 4. University of Minnesota Medical School
- 5. Zagazig university
- 6. Umm Al-Qura University
- 7. Beni-Suef University
- 8. ,Al-Azhar University
- 9. University of Benin, Nigeria
Description
Fractionation of the stem bark of Enantia chlorantha Oliv yields three alkaloids Palmatine (1), Jatrorrhizine (2), Columbamine (3), and β-Sitosterol (4). In this investigation, density functional theory (DFT) calculations were carried out to evaluate the electronic structure and properties of 1-4 by DFT-B3LYP/6-31G level of theory using Gaussian 09 software. Quantum molecular descriptors of the title compounds: ionization potential (IP) and Electron Affinities (EA), Hardness (η), Softness (S), Electronegativity (μ), Electrophilic Index (ω), Electron Donating Power (ω-), Electron Accepting Power (ω+) and Energy Gap (Eg) have been calculated. The in vitro cytotoxicity of the compounds was investigated against MCF-7, HCT116 cancer cell lines using Wi-38 cells as control. The compounds inhibited the proliferation of the MCF-7 and HCT116 cell lines and induced apoptosis via up-regulation of caspase-3, Bax, PARP cleavage, and downregulation of Bcl-2. DFT analyses revealed that compounds 1 and 3 have smaller energy gaps, 0.072 and 0.071eV, respectively, with the highest dipole moments, hence, more chemically reactive and exhibited better modulation of caspase-3 enzyme and inhibitory activities of the MCF-3 and HCT116 cell lines. The antimicrobial and antiparasitic evaluation of 1 - 4 showed moderate efficacy against the bacterial strains and moderate antiparasitic activity against Cichlidogyrus tilapia.
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