Quassinoids from the Root Barks of Ailanthus altissima: Isolation, Configurational Assignment, and Cytotoxic Activities

Abstract

Ailanthus altissima | Simaroubaceae | Quassinoids | Cytotoxicity | Apoptosis 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.

Isolation of cytotoxic daphnane-type and tigliane-type diterpenoids from Daphne genkwa using MetGem software

“…Cell growth inhibition was assessed by MTT assay, in line with previously reported. 11,16,34 The cytotoxicity of all diterpenoids and positive control (cisplatin, sorafenib, and doxorubicin) were evaluated against A549, Hep3B, and MCF-7 cell lines using the MTT method.…”

Highly Oxidized Germacranolides from Elephantopus tomentosus and the Configurational Revision of Some Previously Reported Analogues

“…HepG2 and Hep3B cells were treated with 1 for 48 h, and the cellular morphological changes were observed by phase-contrast microscopy. Hoechst 33258 staining was performed to assess apoptotic nuclear morphology. , …”

Discovery of Michael reaction acceptors from the leaves of Ai-lanthus altissima by a modified tactic

“…In our previous work on the Simaroubaceae family, a series of MRAs containing α ,β -unsaturated ketone were isolated and identified. [20][21][22][23] In this study, to discover more MRAs, we turned our focus toward the leaves of Ailanthus altissima . This effort resulted in the isolation of seven undescribed MRAs.…”