Structure elucidation of a new terpenylated coumarin with the combination of CASE algorithms and DFT/NMR approach

One new terpenylated coumarin ailanthuscoumarin was isolated from the root barks of Ailanthus altissima (Mill.) Swingle. The high oxidation of the compound led to the difficulty of structure elucidation by 2D-NMR spectra. Its structure was determined with the aid of computer-assisted structure eluci...

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Bibliographic Details
Published in:Journal of asian natural products research 2021-10, Vol.23 (10), p.982-991
Main Authors: Lv, Tian-Ming, Guo, Rui, Yan, Zhi-Yang, Du, Ye-Qing, Lin, Bin, Huang, Xiao-Xiao, Song, Shao-Jiang
Format: Article
Language:English
Subjects:
Absolute configuration
Ailanthus altissima
Algorithms
Circular dichroism
computer-assisted structure elucidation
Coumarin
DFT/NMR approach
Dichroism
Expert systems
Hepatoma
Mathematical analysis
NMR
Nuclear magnetic resonance
Oxidation
Simaroubaceae
terpenylated coumarin
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Summary:One new terpenylated coumarin ailanthuscoumarin was isolated from the root barks of Ailanthus altissima (Mill.) Swingle. The high oxidation of the compound led to the difficulty of structure elucidation by 2D-NMR spectra. Its structure was determined with the aid of computer-assisted structure elucidation (CASE) expert systems and Gauge-independent atomic orbital (GIAO) NMR calculations. The absolute configuration of ailanthuscoumarin was determined by the comparison between the experimental and calculated electronic circular dichroism (ECD) spectra. The anti-hepatoma activity of ailanthuscoumarin against two human hepatoma cells (Hep3B, HepG2) was also reported.
ISSN:1028-6020
1477-2213
DOI:10.1080/10286020.2020.1804377