Artemisiyneolides A–K, Guaiane Sesquiterpenoid-Heptatriyne Hybrids through C–C Linkages from Artemisia sieversiana with Antihepatoma Activity

Abstract

Artemisiyneolides A–K (1–11), guaiane sesquiterpenoid-heptatriyne hybrids, were isolated from Artemisia sieversiana (Asteraceae). Their structures were elucidated using NMR, HRESIMS, ECD calculations, and X-ray diffraction analysis. Compounds 1–11 featured 5/5/7/5-fused ring frameworks bearing a 1,3,5-heptatriyne side chain by C–C linkages, which were biosynthetically generated by [4 + 2] Diels–Alder cycloadditions. The investigation of antihepatoma activity suggested that compound 4 exhibited significant inhibition on HepG2, Huh7, and SK-Hep-1 cell lines, with IC50 values of 22.8 ± 1.8, 31.7 ± 1.4, and 26.3 ± 3.0 μM, respectively.