Experimental and Theoretical Nuclear Magnetic Resonance Data from Tryptanthrin, an Alkaloid with Potential Activity Against Human Coronavirus

F. L. Costa, S. B. O. Fernandes, C. E. Fingolo, F. Boylan, A. M. J. C. Neto, G. S. Mota, B. A. Soares, M. Siqueira, Thaís Forest Giacomello
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Abstract

Coronaviruses belong to the subfamily Coronavirinae, which are large viruses with a single Ribonucleic acid tape and a nucleocapsid. In a recent study it was found that the molecule of tryptanthrin has antiviral potential against human coronavirus NL63. In this work, we used a combination of theoretical techniques with experimental nuclear magnetic resonance data to assist in the structural characterization of the Tryptanthrin molecule. Tryptanthrin was extracted from Couroupita guianensis leaves. The theoretical calculations of hydrogen-1, homonuclear spin–spin coupling constants and the quantum theory of atoms in molecules were performed employing density functional theory. Our results show that the hydrogen-1 chemical shifts calculated at the gaseous phase and solvent presented similar performance. The quantum theory of atoms in molecules calculations was able to quantify and qualify bonded interactions based on five topological parameters obtained at the analyzed bond critical point to tryptanthrin molecule. We obtained a satisfactory correlation between tryptanthrin delocalization index values and its experimental and calculated proton–proton coupling constants. In conclusion, the theoretical techniques used in this work in combination with NMR experimental data can be a useful tool in aiding the structural determination of organic compounds.
具有抗人冠状病毒活性生物碱色胺菊酯的核磁共振实验与理论研究
冠状病毒属于冠状病毒亚科,是一种具有单核糖核酸带和核衣壳的大型病毒。最近的一项研究发现,色氨酸分子对人类冠状病毒NL63具有抗病毒潜力。在这项工作中,我们将理论技术与实验核磁共振数据相结合,以协助色氨酸分子的结构表征。从桂竹叶中提取色胺菊酯。采用密度泛函理论计算了氢-1、同核自旋-自旋耦合常数和分子中原子的量子理论。结果表明,在气相和溶剂中计算的氢-1化学位移具有相似的性能。分子计算中的原子量子理论能够基于在分析的键临界点处获得的五个拓扑参数来量化和限定键相互作用。我们得到了色氨酸离域指数值与其实验和计算的质子-质子耦合常数之间令人满意的相关性。总之,在这项工作中使用的理论技术与核磁共振实验数据相结合,可以成为帮助确定有机化合物结构的有用工具。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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