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Natural Andrographolide Isolated from Andrographis paniculata as Potent Epileptic Agent: Spectroscopy, Molecular Structure, and Molecular Docking Investigation

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Abstract

In this study, a comparative experimental and theoretical investigation of the isolation, characterization, and molecular electronic investigation of natural andrographolide is reported. The studied compound was isolated form the extracts of A. paniculata and characterized by spectroscopic technique and compared with theoretically simulated spectroscopic data. Also, in-silico molecular docking investigation of the anti-epileptic potency of natural andrographolide is appraised by assessing its efficacy to bind with 1R9O receptor. All computations were achieved  at the B3LYP/6-311++G(d,p) level of theory within the framework of density functional theory (DFT). A comprehensive study of the isomerization of natural andrographolide was also considered by conducting several potential energy surface scans for both ring and angle rotation. The results prompt that the cis-conformer is more unstable than the trans-conformer with energy barrier height of − 1156.603 kcal/mol lower than that obtained for the trans isomer. The molecular reactivity descriptors also divulged that natural andrographolide was considerably reactive and its reactivity and stability was observed to be influenced by different solvents polarity and permittivity. The molecular docking investigations also showed that natural andrographolide possesses substantial anti-epileptic activity in comparison with diazepam and thus, a potential pharmacophore for the development of efficient anti-epileptic agents.

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Acknowledgements

We acknowledge the center for high-performance computing (CHPC) in South Africa for providing the computational resources utilized in this work.

Funding

This study was supported by the Talent Introduction Funds of Sichuan University of Science and Engineering (no. 2018RCL13), Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education (LZJ18202), the Key Laboratories of Fine Chemicals and Surfactants in Sichuan Provincial Universities (2019JXZ02), the Central Guidance on Local Science and Technology Development Fund of Sichuan Province (no. 2021ZYD0062). The center for high performance computing (CHPC) South Africa is acknowledged for providing the computational resources utilized in this work.

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Authors and Affiliations

  1. Computational and Bio-Simulation Research Group, University of Calabar, Calabar, Nigeria

    Aniekan E. Owen, Hitler Louis, Emmanuel U. Ejiofor, Terkumbur E. Gber & Innocent Benjamin

  2. Department of Chemistry, Akwa Ibom State University, Uyo, Nigeria

    Aniekan E. Owen

  3. School of Materials Science and Engineering, Sichuan University of Science and Engineering, Zigong, 643000, Sichuan, People’s Republic of China

    Wilfred Emori

  4. Key Laboratory of Material Corrosion and Protection of Sichuan Province, Zigong, 643000, Sichuan, People’s Republic of China

    Wilfred Emori

  5. Department of Pure and Applied Chemistry, Faculty of Physical Sciences, University of Calabar, Calabar, Nigeria

    Hitler Louis & Terkumbur E. Gber

  6. College of Chemical Engineering, Institute of Pharmaceutical Engineering Technology and Application, Key Laboratory of Green Chemistry of Sichuan Institutes of Higher Education, Sichuan University of Science and Engineering, Zigong, 643000, Sichuan, People’s Republic of China

    Chun-Ru Cheng & Liu Ling

  7. Department of Physics, University of Ilorin, Ilorin, Nigeria

    Muyiwa M. Orosun

  8. Research Centre for Synthesis and Catalysis, Department of Chemical Sciences, University of Johannesburg, Johannesburg, South Africa

    Adedapo S. Adeyinka

  9. Department of Chemical Sciences, Faculty of Science, Clifford University, Owerrinta, Aba, Abia State, Nigeria

    Emmanuel U. Ejiofor

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  1. Aniekan E. Owen
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Contributions

HL: project conceptualization, design, supervision, and administration. AEO: resources, analysis, writing, and editing. EUE and WE: analysis, writing, and manuscript draft. TEG: writing and manuscript draft. IB: writing and visualization: analysis, validation, writing, editing. MMO: analysis, validation, review and editing. LL and MMO: writing, editing and proof reading. Writing, editing, and reviewing. ASA and C-RC: resources, methodology, and analysis.

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Correspondence to Hitler Louis, Emmanuel U. Ejiofor, Wilfred Emori or Chun-Ru Cheng.

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Owen, A.E., Louis, H., Ejiofor, E.U. et al. Natural Andrographolide Isolated from Andrographis paniculata as Potent Epileptic Agent: Spectroscopy, Molecular Structure, and Molecular Docking Investigation. Chemistry Africa 6, 2445–2461 (2023). https://doi.org/10.1007/s42250-023-00657-9

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