Antitumor Activities of Six Quassinoids from Ailanthus altissima

Wang, Ruxing; Mao, Xiaoxia; Zhou, Jian‐Liang; Zhang, Manli; Wu, Yibing; Huo, Changhong; Shi, Qing; Sauriol, Françoise; Gu, Yu‐Cheng

doi:10.1007/s10600-017-1903-9

Cited by 10 publications

(4 citation statements)

References 12 publications

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“…In traditional Chinese medicine, different parts of Ailanthus altissima have been extensively used for the treatment of ascariasis, diarrhea, spermatorrhea, bleeding, and gastrointestinal diseases . Pharmacological studies indicated that the extracts of this plant have a broad range of bioactivities such as antitumor, antiviral, antimalarial, and antimicrobial actions …”

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confidence: 99%

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Structurally Diverse Highly Oxygenated Triterpenoids from the Roots of Ailanthus altissima and Their Cytotoxicity

et al. 2018

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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 IC value of 8.2 μM in vitro.

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confidence: 99%

“…Previous phytochemical investigations reported that the main secondary metabolites of A. altissima were quassinoids, β-carboline alkaloids, sterols, and lipids . However, investigation of the triterpenoids, the precursors of quassinoids, drew less attention .…”

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Structurally Diverse Highly Oxygenated Triterpenoids from the Roots of Ailanthus altissima and Their Cytotoxicity

et al. 2018

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“…The structures of the known compounds were identified by the comparison of their spectroscopic data with the data from the corresponding values in the literature as 2‐dihydroailanthone ( 6 ), shinjudilactone C ( 7 ), respectively. [ 15‐16 ]…”

Section: Resultsmentioning

confidence: 99%

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

Bai

et al. 2021

Chin. J. Chem.

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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.

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“…Other antitumor products have been characterized from A. altissima (Figure 2), such as altissinol A (Y. Wang et al, 2013), ailantinol derivatives (Kubota et al, 1996; Tamura, Fukamiya, Okano, Koyama, & Koike, 2006; Tamura et al, 2003; R. W. Wang et al, 2017), 2‐dihydroailanthone (R. Wang et al, 2016), shinjulactone derivatives (Tamura et al, 2002; X. L. Yang, Yuan, Zhang, Li, & Ye, 2014) endowed with antibacterial, antitumor, antifungal, or antiviral activities (Cho, Jeong, Jang, & Choi, 2018). The plant contains canthin‐6‐one alkaloids, notably 1‐methoxy‐canthin‐6‐one, which displays potent proapoptotic properties (Ammirante et al, 2006; De Feo et al, 2005) and the β‐carbolin alkaloid 9‐hydroxycanthin‐6‐one which inhibits the activation of tumor‐associated macrophages (Jeong et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Anticancer properties and mechanism of action of the quassinoid ailanthone

Bailly

2020

Phytotherapy Research

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Ailanthone (AIT) is a quassinoid natural product isolated from the worldwide‐distributed plant Ailanthus altissima. The drug displays multiple pharmacological properties, in particular significant antitumor effects against a variety of cancer cell lines in vitro. Potent in vivo activities have been evidenced in mice bearing hepatocellular carcinoma, nonsmall cell lung cancer and castration‐resistant prostate cancer. This review focusses on the mechanism of action of AIT, notably to highlight the capacity of the drug to activate DNA damage responses, to inhibit the Hsp90 co‐chaperone p23 and to modulate the expression of several microRNA. The interconnexion between these effects is discussed. The unique capacity of AIT to downregulate oncogenic miR‐21 and to upregulate the tumor suppressor miRNAs miR‐126, miR‐148a, miR‐195, and miR‐449a is presented. AIT exploits several microRNAs to exert its anticancer effects in distinct tumor types. AIT is one of the rare antitumor natural products that binds to and strongly inhibits cochaperone p23, opening interesting perspectives to treat cancers. However, the toxicity profile of the molecule may limit its development as an anticancer drug, unless it can be properly formulated to prevent AIT‐induced gastro‐intestinal damages in particular. The antitumor properties of AIT and analogs are underlined, with the aim to encourage further pharmacological studies with this underexplored natural product and related quassinoids. Highlights Ailanthone (AIT) is an anticancer quassinoid isolated from Ailanthus altissima It inhibits proliferation and induces cell death of many cancer cell types The drug activates DNA damage response and targets p23 cochaperone Up or downregulation of several microRNA by AIT contributes to the anticancer activity Analogs or specific formulations must be developed to prevent the toxicity of AIT

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Antitumor Activities of Six Quassinoids from Ailanthus altissima

Cited by 10 publications

References 12 publications

Structurally Diverse Highly Oxygenated Triterpenoids from the Roots of Ailanthus altissima and Their Cytotoxicity

Structurally Diverse Highly Oxygenated Triterpenoids from the Roots of Ailanthus altissima and Their Cytotoxicity

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

Anticancer properties and mechanism of action of the quassinoid ailanthone

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