Structurally Diverse Highly Oxygenated Triterpenoids from the Roots of Ailanthus altissima and Their Cytotoxicity
- J Nat Prod. 2018 Aug 24;81(8):1777-1785. doi: 10.1021/acs.jnatprod.8b00208.
- 1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou 730000 , People's Republic of China.
- 2. State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , People's Republic of China.
Ten new triterpenoids, ailanaltiolides A-J (1-10), and three known analogues (11-13) were isolated from the roots of Ailanthus altissima. Compounds 1-7 are apotirucallane-type, compounds 8 and 9 are tirucallane-type, and compound 10 is a trinordammarane-type triterpenoid. This is the first study indicating the genus Ailanthus as a potential source for apotirucallane derivatives, which contain an α,β-unsaturated-ε-lactone A-ring and diversely modified C-17 side chains. Spectroscopic data interpretation, electronic circular dichroism analysis, and X-ray crystallographic data defined the structures and absolute configurations of these triterpenoids. Compounds 2, 7, and 8 showed cytotoxicity against four tumor cell lines (HeLa, 786-O, HepG2, and A549). In particular, compound 2 exhibited the highest activity against 786-O cells with an IC50 value of 8.2 μM in vitro.