Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

[ASAP] Artatrovirenols A and B: Two Cagelike Sesquiterpenoids from Artemisia atrovirens

[ASAP] Artatrovirenols A and B: Two Cagelike Sesquiterpenoids from Artemisia atrovirens
Li-Hua Su, Chang-An Geng, Tian-Ze Li, Yun-Bao Ma, Xiao-Yan Huang, Xue-Mei Zhang, Ji-Jun Chen
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[5.3.1.1.4,1101,5]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 μΜ, respectively. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.0c01491. 1D and 2D NMR, HRESIMS, IR, [α]D, and CD spectra and bioassay (PDF) Crystallographic data of 1 (CIF) This article has not yet been cited by other publications.

Publisher URL: http://feedproxy.google.com/~r/acs/joceah/~3/Qf344LZMuIg/acs.joc.0c01491

DOI: 10.1021/acs.joc.0c01491

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