Structure Revision of Heptacyclic Naphthoquinone Dimer Arnebidin Based on NMR Spectroscopic Analysis and X-ray Crystallography

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
Le Wang, Shuhui Wang, Qiqi Wang, Yuqi Wang, Hong Liang, Qingying Zhang, Pengfei Tu
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引用次数: 0

Abstract

Arnebidin, a heptacyclic naphthoquinone dimer with a tricyclo[3.3.0.01,3]octane core, which was first isolated from Arnebia hispidissima and later found from A. euchroma. Its structure was identified by the analysis of NMR and EI-MS data. In the present work, a heptacyclic naphthoquinone dimer ((±)-1) was obtained from the petroleum ether portion of the ethanol extract of Arnebia euchroma. By comparing the NMR data of 1 with the literatures, compound 1 should be identified as arnebidin. However, the single-crystal X-ray diffraction analysis followed by reinterpretation of the NMR data revealed that the structure of 1 was a heptacyclic naphthoquinone dimer with a tricyclo[3.2.1.02,7]octane core. Thus, we proposed that arnebidin should be revised to 1.

Abstract Image

基于核磁共振和x射线晶体学的七环萘醌二聚体紫金蓟苷结构修正
Arnebidin是一种七环萘醌二聚体,其核心为三环[3.3.0.01,3]辛烷值,最初从紫檀中分离得到,后来从a. euchroma中发现。通过NMR和EI-MS对其结构进行了鉴定。从赤藓乙醇提取物的石油醚部分得到了一个七环萘醌二聚体(±)-1)。通过对化合物1的NMR数据与文献的比较,化合物1应该被鉴定为arnebidin。然而,单晶x射线衍射分析和核磁共振数据的重新解释表明,1的结构是一个具有三环[3.2.1.02,7]辛烷核的七环萘醌二聚体。因此,我们建议将arnebidin修改为1。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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