Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 21, Pages 13466-13471Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01491
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Funding
- Yunnan Wanren Project [YNWR-KJLJ-2019-002]
- Program of Yunling Scholarship
- Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province
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Artatrovirenols A and B (1 and 2), two novel cagelike sesquiterpenoids, possess a unique 5/5/6/5/5-pentacyclic and a 5/5/6/5-tetracyclic system with an unprecedented tetracyclo[5.3.1.1. (4,)(11)0(1,5)]dodecane scaffold from Artemisia atrovirens. The structures of compounds 1 and 2 including their absolute stereochemistry were elucidated through extensive spectroscopic analyses, X-ray crystallography, and quantum chemical calculations. Plausible biosynthetic pathways for the new isolates were proposed from the naturally occurring arglabin (3) via the key intramolecular Diels-Alder cycloaddition. Compound 1 showed cytotoxicity against three human hepatoma cell lines (HepG2, SMMC-7721, and Huh7) with half maximal inhibitory concentration values of 123.8, 44.0, and 142.6 mu M, respectively.
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