Citation: Ling-Hao Zhao, Hai-Wei Yan, Jian-Shuang Jiang, Xu Zhang, Xiang Yuan, Ya-Nan Yang, Pei-Cheng Zhang. Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy[J]. Chinese Chemical Letters, ;2024, 35(5): 108863. doi: 10.1016/j.cclet.2023.108863 shu

Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

yyn@imm.ac.cn

pczhang@imm.ac.cn

Received Date: 5 June 2023
Revised Date: 26 July 2023
Accepted Date: 28 July 2023
Available Online: 29 July 2023

Figures(5)

An approach for distinguishing two types of positional isomers of dimeric shikonin and its analogs was explored with ⁴J_{C, H} long-range correlation by prolonging the acquisition time at ^2,3J_{C, H} values of 2.0 and 8.0 Hz. Furthermore, the ¹H (proton) nuclear magnetic resonance (NMR) pattern of phenolic hydroxyl protons was developed as a "diagnosis signal" to ascertain the relative location of each side chain in DMSO–d₆ at sample concentrations of 0.022–0.034 mol/L. The chemical shift differences of 0.6 ppm between OH-5′ and OH-1 and between OH-8′ and OH-4 are assigned to Type A and Type B, respectively. All reported ambiguous structures were corrected by this pattern. Additionally, the steric structures of isolated compounds were elucidated by quantum chemical calculations of electronic circular dichroism (ECD) spectra.
- Arnebia euchroma,
- Dimeric hydroxyl naphthoquinones,
- Positional isomers,
- ¹H NMR spectroscopy,
- Chemical shift difference
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沈阳化工大学材料科学与工程学院沈阳 110142

Effective assignment of positional isomers in dimeric shikonin and its analogs by 1H NMR spectroscopy

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通讯作者: 陈斌, bchen63@163.com

Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy