DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i>
Fractionation of the stem bark of <i>Enantia chlorantha</i> Oliv yields three alkaloids, palmatine (<b>1</b>), jatrorrhizine (<b>2</b>), columbamine (<b>3</b>), and <i>β</i>-Sitosterol (<b>4</b>). In this investigation, density...
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2024-03-01
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| author | Vincent O. Imieje Ahmed A. Zaki Mansour A. E. Bashar Islam Rady Mohamed A. M. El-Tabakh Mohamed A. E. Abd El-Aziz Eman. S. Abou-Amra Shahd Yasser Ibraheem M. M. Gobaara Mohammed A. S. Abourehab Reham M. Samra Hussein A. El-Naggar Abiodun Falodun |
| author_facet | Vincent O. Imieje Ahmed A. Zaki Mansour A. E. Bashar Islam Rady Mohamed A. M. El-Tabakh Mohamed A. E. Abd El-Aziz Eman. S. Abou-Amra Shahd Yasser Ibraheem M. M. Gobaara Mohammed A. S. Abourehab Reham M. Samra Hussein A. El-Naggar Abiodun Falodun |
| author_sort | Vincent O. Imieje |
| collection | DOAJ |
| description | Fractionation of the stem bark of <i>Enantia chlorantha</i> Oliv yields three alkaloids, palmatine (<b>1</b>), jatrorrhizine (<b>2</b>), columbamine (<b>3</b>), and <i>β</i>-Sitosterol (<b>4</b>). In this investigation, density functional theory (DFT) calculations were carried out to evaluate the electronic structure and properties of <b>1</b>–<b>4</b> by DFT-B3LYP/6-31G level of theory using Gaussian 09 software. The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), HOMO-LUMO energy difference (band gap), hardness (η), softness (S), dipole moment (μ), electronegativity (χ), hydrophobicity (logP), topological surface area (TPSA), and energy gap (Eg) were calculated. The in vitro cytotoxicity of the compounds was investigated against MCF-7 and HCT116 cancer cell lines using Wi-38 cells as a control. The compounds inhibited the proliferation of the MCF-7 and HCT116 cell lines and induced apoptosis via upregulation of caspase-3, Bax, PARP cleavage, and downregulation of Bcl-2. DFT analyses revealed that compounds <b>1</b> and <b>3</b> have smaller energy gaps, 0.072 and 0.071eV, respectively, with the highest dipole moments; hence, these compounds are more chemically reactive and exhibit better modulation of caspase-3 enzyme and inhibitory activities of the MCF-3 and HCT116 cell lines. The antimicrobial and antiparasitic evaluation of <b>1</b>–<b>4</b> showed moderate efficacy against the bacterial strains and moderate antiparasitic activity against <i>Cichlidogyrus tilapia</i>. |
| first_indexed | 2024-04-24T18:24:36Z |
| format | Article |
| id | doaj.art-6f543e9bf9c643a2b22827c5658a755c |
| institution | Directory Open Access Journal |
| issn | 2813-2998 |
| language | English |
| last_indexed | 2024-04-24T18:24:36Z |
| publishDate | 2024-03-01 |
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| series | Drugs and Drug Candidates |
| spelling | doaj.art-6f543e9bf9c643a2b22827c5658a755c2024-03-27T13:32:57ZengMDPI AGDrugs and Drug Candidates2813-29982024-03-013129131010.3390/ddc3010017DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i>Vincent O. Imieje0Ahmed A. Zaki1Mansour A. E. Bashar2Islam Rady3Mohamed A. M. El-Tabakh4Mohamed A. E. Abd El-Aziz5Eman. S. Abou-Amra6Shahd Yasser7Ibraheem M. M. Gobaara8Mohammed A. S. Abourehab9Reham M. Samra10Hussein A. El-Naggar11Abiodun Falodun12Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City 300001, NigeriaDepartment of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptMarine Biology and Fish Sciences Laboratory, Zoology and Entomology Department, Faculty of Science for (Boys), Al-Azhar University, Nasr City, Cairo 11884, EgyptMolecular Biology Laboratory, Zoology and Entomology Department, Faculty of Science (Boys), Al-Azhar University, Nasr City, Cairo 11884, EgyptMarine Biology and Fish Sciences Laboratory, Zoology and Entomology Department, Faculty of Science for (Boys), Al-Azhar University, Nasr City, Cairo 11884, EgyptMarine Biology and Fish Sciences Laboratory, Zoology and Entomology Department, Faculty of Science for (Boys), Al-Azhar University, Nasr City, Cairo 11884, EgyptChemistry Department, Faculty of Science (Girls), Al-Azhar University, Nasr City, Cairo 11884, EgyptFaculty of Medicine, Zagazig University, Ash Sharqia Governorate, Zagazig 44511, EgyptInvertebrates Laboratory, Zoology and Entomology Department, Faculty of Science (Boys), Al-Azhar University, Nasr City, Cairo 11884, EgyptDepartment of Pharmaceutics, Faculty of Pharmacy, Umm Al-Qura University, Makkah 21955, Saudi ArabiaDepartment of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptMarine Biology and Fish Sciences Laboratory, Zoology and Entomology Department, Faculty of Science for (Boys), Al-Azhar University, Nasr City, Cairo 11884, EgyptDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City 300001, NigeriaFractionation of the stem bark of <i>Enantia chlorantha</i> Oliv yields three alkaloids, palmatine (<b>1</b>), jatrorrhizine (<b>2</b>), columbamine (<b>3</b>), and <i>β</i>-Sitosterol (<b>4</b>). In this investigation, density functional theory (DFT) calculations were carried out to evaluate the electronic structure and properties of <b>1</b>–<b>4</b> by DFT-B3LYP/6-31G level of theory using Gaussian 09 software. The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), HOMO-LUMO energy difference (band gap), hardness (η), softness (S), dipole moment (μ), electronegativity (χ), hydrophobicity (logP), topological surface area (TPSA), and energy gap (Eg) were calculated. The in vitro cytotoxicity of the compounds was investigated against MCF-7 and HCT116 cancer cell lines using Wi-38 cells as a control. The compounds inhibited the proliferation of the MCF-7 and HCT116 cell lines and induced apoptosis via upregulation of caspase-3, Bax, PARP cleavage, and downregulation of Bcl-2. DFT analyses revealed that compounds <b>1</b> and <b>3</b> have smaller energy gaps, 0.072 and 0.071eV, respectively, with the highest dipole moments; hence, these compounds are more chemically reactive and exhibit better modulation of caspase-3 enzyme and inhibitory activities of the MCF-3 and HCT116 cell lines. The antimicrobial and antiparasitic evaluation of <b>1</b>–<b>4</b> showed moderate efficacy against the bacterial strains and moderate antiparasitic activity against <i>Cichlidogyrus tilapia</i>.https://www.mdpi.com/2813-2998/3/1/17<i>Enantia chlorantha</i>DFTantimicrobialcaspase-3MCF-7 and HCT116 cell lines<i>Cichlidogyrus tilapia</i> |
| spellingShingle | Vincent O. Imieje Ahmed A. Zaki Mansour A. E. Bashar Islam Rady Mohamed A. M. El-Tabakh Mohamed A. E. Abd El-Aziz Eman. S. Abou-Amra Shahd Yasser Ibraheem M. M. Gobaara Mohammed A. S. Abourehab Reham M. Samra Hussein A. El-Naggar Abiodun Falodun DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i> Drugs and Drug Candidates <i>Enantia chlorantha</i> DFT antimicrobial caspase-3 MCF-7 and HCT116 cell lines <i>Cichlidogyrus tilapia</i> |
| title | DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i> |
| title_full | DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i> |
| title_fullStr | DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i> |
| title_full_unstemmed | DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i> |
| title_short | DFT Calculations, Pro-Apoptotic Effects, and Anti-Infective Investigations of Alkaloids Isolated from the Stem Bark Extract of <i>Enantia chlorantha</i> |
| title_sort | dft calculations pro apoptotic effects and anti infective investigations of alkaloids isolated from the stem bark extract of i enantia chlorantha i |
| topic | <i>Enantia chlorantha</i> DFT antimicrobial caspase-3 MCF-7 and HCT116 cell lines <i>Cichlidogyrus tilapia</i> |
| url | https://www.mdpi.com/2813-2998/3/1/17 |
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