Molecular Modeling of the Spectroscopic, Structural, and Bioactive Potential of Tetrahydropalmatine: Insight from Experimental and Theoretical Approach

Abstract

Tetrahydropalmatine have been experimentally reported to have promising biological applications, although detailed theoretical investigation on its structural activities regarding its potency as a potential anti-inflammatory drug candidate has not been reported. In that regard, this present work focuses on the experimental and theoretical investigation of tetrahydropalmatine. The studied structure was experimentally isolated followed by detailed theoretical calculations within the framework of density functional theory (DFT) employing the 6-311++G(d,p) basis set. Theoretical and experimental characterization of the structure was observed to agree as different functional groups were analyzed. Molecular electronic properties of the isolated compound were investigated using five different functionals: B3LYP, PBE0, TPSSTPSS, M06-2X, and wB97XD for comparative purposes which present isolated structure to be more reactive at PBE0 and more stable geometry at wB97XD levels of theory. The most intense interaction from perturbation energy analysis was from δ$\to \delta$* from PBEO with a stabilization energy of 108120.75 kcal/mol. The anti-inflammatory activity of the studied compound was investigated using the molecular docking simulations from which the results revealed that the proteins with PDB IDs: 4Z69, 5V0V, 6U4X, and 6U5A possess best pose binding affinities of −7.6, −6.8, −6.6 and −6.4 kcal/mol respectively.

Keywords:

• Tetrahydropalmatine
• spectroscopy
• DFT
• benchmarking
• molecular docking

Acknowledgements

The center for high performance computing (CHPC) South Africa is acknowledged for providing the computational resources utilized in this work.

Author contributions

Wilfred Emori: Project administration, analysis, writing, and editing. Hitler Louis: Conceptualization, design, supervision, writing, and editing. Rawlings Timothy: Results analysis, writing, editing, and manuscript first draft. Ernest C. Agwamba, Tomsmith O. Unimuke: Analysis, writing and manuscript final draft, Aniekan Owen: Resources, analysis, writing, and editing. Terkumbur E. Gber: Analysis, writing, and editing. Liu Ling: Analysis, writing and editing. Chun-Ru Cheng: Resources validation, writing and editing. Adeyinka S. Adeyemi: Methodology, editing and resources. Offiong E. Offiong and Stephen A. Adalikwu: Validation, analysis, and editing.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Data availability statement

All data are contained within the manuscript and manuscript supporting information document (ESI).

Additional information

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].