Trimeric and dimeric sesquiterpenoids from Artemisia atrovirens and their cytotoxicities

Two sesquiterpenoid trimers, artematrotrimers A (1) and B (2), and two sesquiterpenoid dimers, artematrodimers A (3) and B (4), possessing unprecedented scaffolds with a methylene-bridged connection were identified from Artemisia atrovirens. Their structures and absolute stereochemistry were determi...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-03, Vol.8 (6), p.1249-1256
Main Authors: Li-Hua, Su, Tian-Ze Li, Chang-An, Geng, Yun-Bao, Ma, Xiao-Yan, Huang, Jin-Ping, Wang, Zhang, Xue-Mei, Ji-Jun, Chen
Format: Article
Language:English
Subjects:
Biocompatibility
Biological activity
Cell lines
Chemical bonds
Covalent bonds
Crystallography
Crystals
Cytotoxicity
Dimers
NMR
Nuclear magnetic resonance
Oligomers
Organic chemistry
Sesquiterpenoids
Single crystals
Stereochemistry
Toxicity
Trimers
X-ray diffraction
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Summary:Two sesquiterpenoid trimers, artematrotrimers A (1) and B (2), and two sesquiterpenoid dimers, artematrodimers A (3) and B (4), possessing unprecedented scaffolds with a methylene-bridged connection were identified from Artemisia atrovirens. Their structures and absolute stereochemistry were determined by comprehensive spectroscopic data, single-crystal X-ray diffraction analyses, and ECD calculations. Compounds 1–4 represent a new type of sesquiterpenoid oligomers featuring the connections between hetero sesquiterpenoid units via one or two C–C bonds. A possible biosynthetic pathway for 1–4 was also proposed. Compound 3 showed obvious cytotoxicity against HepG2 and Huh7 cell lines with IC50 values of 21.9 and 22.6 μM, respectively.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo01615b