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Quassinoids from the Root Barks of Ailanthus altissima : Isolation, Configurational Assignment, and Cytotoxic Activities
Author(s) -
Du YeQing,
Bai Ming,
Yu XiaoQi,
Lv TianMing,
Lin Bin,
Huang XiaoXiao,
Song ShaoJiang
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000558
Subject(s) - ailanthus altissima , chemistry , simaroubaceae , stereochemistry , circular dichroism , terpene , annexin , biochemistry , apoptosis , botany , biology
Abstract Main observation and conclusion Quassinoids, a class of highly oxygenated triterpenes, have been isolated as bitter principles from the plants of Simaroubaceae family. Five new quassinoids, chouchunlactone A—E (1 — 5 ), and two known ones were identified from the root barks of Ailanthus altissima Swingle (Simaroubaceae). The chemical structures of the new compounds were deduced by spectroscopic data analyses, NMR calculations and DP4+ probability analysis. The absolute configurations were defined by comparison of their experimental and calculated electronic circular dichroism (ECD) spectra data, and compounds 1 — 2 were further confirmed by single‐crystal X‐ray diffraction. Biologically, compound 5 showed potencies equivalent to sorafenib (IC 50 value, 9.70 μmol·L –1 ) against HepG2 cells. The Hoechst 33342 staining, JC‐1 fluorescent dye and Annexin V/PI analysis studies demonstrated that 5 can induce apoptosis and attenuate mitochondrial membrane potential (MMP) in HepG2 cells.