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Three Types of Isocoumarins with Unusual Carbon Skeletons from Artemisia dubia var. subdigitata and Their Antihepatoma Activity
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  • Ke-Xin Yang,
  • Tian-Ze Li,
  • Yun-Bao Ma,
  • Yong-Cui Wang,
  • Feng-Jiao Li,
  • Jijun Chen
Ke-Xin Yang
Kunming Institute of Botany Chinese Academy of Sciences
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Tian-Ze Li
Kunming Institute of Botany Chinese Academy of Sciences
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Yun-Bao Ma
Kunming Institute of Botany Chinese Academy of Sciences
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Yong-Cui Wang
Kunming Institute of Botany Chinese Academy of Sciences
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Feng-Jiao Li
Kunming Institute of Botany Chinese Academy of Sciences
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Jijun Chen
Kunming Institute of Botany Chinese Academy of Sciences

Corresponding Author:chenjj@mail.kib.ac.cn

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Abstract

Ten novel isocoumarins, including four pairs of enantiomers, were isolated from Artemisia dubia var. subdigitata (Asteraceae). Com-pounds 1, 2 and 3a/3b possessed a unique 6/6/6-tricyclic system comprising an unusual 1-(2-methylcyclohexyl) propan-1-one moiety fused with isocoumarin core skeleton. Compounds 4a/4b were characterized as an unexpected 2,5-dimethylcyclohexan-1-one scaffold, and compounds 5a/5b and 6a/6b were rare 1,2-seco-isocoumarin. Their structures and absolute configurations were elucidated through spectroscopic data, X-ray crystallography, ECD and NMR calculations with DP4+ analyses. Plausible biosynthetic pathways were proposed from the naturally occurring isocoumarin. Network pharmacological analysis suggested that the targets of compound 1 were significantly enriched in the cell cycle and PI3K-Akt signaling pathway. The molecular docking revealed that compound 1 had high binding affinity with CDK2 (total score: 6.8717). Furthermore, compounds 1 and 2 exhibited inhibitory activity on three human hepa-toma cell lines, with inhibitory ratios of 85.1% and 84.5% (HepG2), 88.2% and 87.3% (Huh7), and 69.2% and 69.1% (SK-Hep-1) at 200 μM, respectively.
Submitted to Chinese Journal of Chemistry
18 Feb 2024Review(s) Completed, Editorial Evaluation Pending
19 Feb 2024Reviewer(s) Assigned
16 Mar 2024Editorial Decision: Revise Minor