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Three Types of Isocoumarins with Unusual Carbon Skeletons from Artemisia dubia var. subdigitata and Their Antihepatoma Activity.
- Source :
- Chinese Journal of Chemistry; Aug2024, Vol. 42 Issue 16, p1901-1912, 12p
- Publication Year :
- 2024
-
Abstract
- Comprehensive Summary: Ten novel isocoumarins, including four pairs of enantiomers, were isolated from Artemisia dubia var. subdigitata (Asteraceae). Compounds 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 hepatoma 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 μmol·L–1, respectively. [ABSTRACT FROM AUTHOR]
- Subjects :
- ARTEMISIA
ISOCOUMARINS
X-ray crystallography
SKELETON
MOLECULAR docking
CELL cycle
Subjects
Details
- Language :
- English
- ISSN :
- 1001604X
- Volume :
- 42
- Issue :
- 16
- Database :
- Complementary Index
- Journal :
- Chinese Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 178442578
- Full Text :
- https://doi.org/10.1002/cjoc.202400172