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| Theoretical Study on the Structure and Properties of a Novel Diterpenoid Lactone Compound Euphorikanin A |
| XU Jia-zhen1, WANG Chang-jiang1, WANG Chao-jie2* |
1. Department of Pharmacy, The Second Affiliated Hospital of Jiaxing University, Jiaxing 314000, China
2. Department of Pharmacy, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China
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Abstract Euphorikanin A, a recently discovered diterpene lactone compound is dated from the roots of Euphorbia reausui, exhibits promising tumor cytotoxic activity. To comprehend its biological effects fully, it is imperative to investigate its structural characteristics, spectral properties, and potential as a therapeutic agent. Consequently, further examination of its structure and properties can serve as a valuable resource for advancing novel pharmaceuticals. The density functional theory B3LYP/6-311++G (2d, p) and ωB97XD/6-311++G (2d, p) methods were applied to calculate the pharmacophoric conformation, geometric and electronic structure, infrared (IR), ultraviolet-visible (UV-Vis), nuclear magnetic resonance (NMR) spectra of the compound Euphorikanin A, and the molecular global reaction index analysis was carried out by using conceptual density functional theory. The pharmacokinetics platform was used to evaluate druggability and ADME/Tox. The calculation results showed that Euphorikanin A has a unique pharmacophoric conformation, and the geometric structure parameters of the compound were similar in both methods and different solvent environments. The calculated values were in good agreement with the crystal parameters. The theoretical infrared spectral characteristics are consistent with the experiment, and the calculated infrared spectra in the water environment are closer to the real values, with a theoretical scaling factor of 0.94. The maximum absorption peak of Euphorikanin A in the UV-Vis spectrum is between 193.88 and 201.75 nm. The theoretical results of the nuclear magnetic data obtained by both methods agree well with the experimental results, with R2 greater than 0.94. The hydroxyl group of the six-membered ring of Euphorikanin A may be the reaction's active site. The compound's global reaction parameters and pharmacokinetics showed good performance, especially regarding Caco-2 cell membrane permeability, blood-brain barrier permeability, and human intestinal absorption. The structure and properties of Euphorikanin A have advantages in druggability and are worthy of further development.
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Received: 2023-07-25
Accepted: 2024-04-15
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Corresponding Authors:
WANG Chao-jie
E-mail: chjwang@wmu.edu.cn
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