Advanced Materials Engineering and Modelling Group, Wroclaw University of Science and Technology, Wroclaw, Poland.
Department of Chemistry and Key Laboratory of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Tsinghua University, Beijing, China.
J Mol Model. 2019 Jun 26;25(7):202. doi: 10.1007/s00894-019-4090-8.
Radix puerariae-a popular traditional Chinese medicine-is used for the treatment of diarrhea, acute dysentery, deafness, and cardiovascular diseases. It can also be used as an effective antioxidant and has been tested as an anticancer drug. Daidzein and puerarin are its main active compounds. The present contribution was focused on experimental and theoretical studies of the H and C NMR chemical shifts and nuclear magnetic shielding parameters of daidzein and puerarin. Experimental data were gained by exploring standard one-dimensional spectra and a set of two-dimensional measurements: COSY, HSQC, and HMBC. The theoretical gauge independent atomic orbital density functional theory supporting studies, were performed to determine shielding constants and chemical shifts in vacuum and methanol-d4 solvent. The correlation between experimental and theoretical data was fairly good, especially when the DFT/PBE0 approach was used. The molecular properties of daidzein and puerine related to antiradical activity were studied in the context of a single-step hydrogen atom transfer mechanism and its correlation with C NMR chemical shifts. Graphical abstract Electron spin density distribution for daidzein radical.
葛根是一种常用的传统中药，用于治疗腹泻、急性痢疾、耳聋和心血管疾病。它也可用作有效的抗氧化剂，并已被测试为抗癌药物。大豆苷元和葛根素是其主要的活性化合物。本研究主要集中在对大豆苷元和葛根素的 1H 和 13C NMR 化学位移和核磁共振屏蔽参数的实验和理论研究上。通过探索标准一维谱和一组二维测量（COSY、HSQC 和 HMBC）获得了实验数据。采用基于赝势的原子轨道密度泛函理论（DFT）进行了理论计算，以确定真空和甲醇-d4 溶剂中的屏蔽常数和化学位移。实验数据和理论数据之间的相关性相当好，尤其是当使用 DFT/PBE0 方法时。在单步氢原子转移机制及其与 13C NMR 化学位移的相关性的背景下，研究了与抗氧化活性相关的大豆苷元和葛根素的分子性质。
