Racemic phenylpropanoids from the root barks of Ailanthus altissima (Mill.) Swingle with cytotoxicity against hepatoma cells

Yan, Zhiyang; Chen, Jingjie; Duan, Zhi-Kang; Yao, Guo-Dong; Lin, Bin; Wang, Xiaobo; Huang, Xiao‐Xiao; Song, Shao‐Jiang

doi:10.1016/j.fitote.2018.09.006

Cited by 13 publications

(2 citation statements)

References 25 publications

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“…The specific optical rotation was calculated by density functional theory (DFT) at the B3LYP/6–311++ G (2d, p) level with the Conductor-like polarizable continuum model (CPCM) solvation model, where MeOH was used as the solvent to match the experimental conditions, and the stated wavelength was 589.3 nm [40].…”

Section: Methodsmentioning

confidence: 99%

Benzophenones from Anemarrhena asphodeloides Bge. Exhibit Anticancer Activity in HepG2 Cells via the NF-κB Signaling Pathway

Liao

Chen

et al. 2019

Molecules

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A chemical investigation of the fibrous roots of Anemarrhena asphodeloides Bge. led to the isolation of four benzophenones, including one new compound (1) and three known ones (2–4). Comprehensive 1D, 2D NMR and HRESIMS data established the structures of the isolated compounds. The absolute configurations were determined by comparison of the calculated optical rotation (OR) with experimental data. All the isolates were evaluated for their cytotoxicities on hepatocellular carcinoma cell lines (HepG2 and Hep3B). Compound 1 showed strong cytotoxicity against HepG2 and Hep3B cells, with IC50 values at 153.1 and 180.6 nM. Through MTT assay, flow cytometry and Western blot analysis, compound 1 demonstrated the ability to stimulate apoptosis via the NF-κB signaling pathway in HepG2 cells. These benzophenones are potential lead compounds for the development of better treatments for hepatocellular carcinoma.

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Section: Methodsmentioning

confidence: 99%

Benzophenones from Anemarrhena asphodeloides Bge. Exhibit Anticancer Activity in HepG2 Cells via the NF-κB Signaling Pathway

Liao

Chen

et al. 2019

Molecules

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“…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). Different cytotoxic triterpenoids and phenylpropanoids have also been characterized from the bark of A. altissima (Bai et al, 2018; Cho et al, 2018; Du et al, 2019; Hong et al, 2013; Lavhale, Kumar, Mishra, & Sitasawad, 2009; Yan et al, 2018). Terpenylated coumarins of interest for some age‐related disorders have been characterized (Dao et al, 2012).…”

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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Chemical constituents from Ailanthus altissima (Mill.) Swingle and chemotaxonomic significance

Zhang

Bai

Yan

et al. 2020

Biochemical Systematics and Ecology

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Racemic phenylpropanoids from the root barks of Ailanthus altissima (Mill.) Swingle with cytotoxicity against hepatoma cells

Cited by 13 publications

References 25 publications

Benzophenones from Anemarrhena asphodeloides Bge. Exhibit Anticancer Activity in HepG2 Cells via the NF-κB Signaling Pathway

Benzophenones from Anemarrhena asphodeloides Bge. Exhibit Anticancer Activity in HepG2 Cells via the NF-κB Signaling Pathway

Anticancer properties and mechanism of action of the quassinoid ailanthone

Chemical constituents from Ailanthus altissima (Mill.) Swingle and chemotaxonomic significance

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