Constituents of the stem barks of Ailanthus altissima and their potential to inhibit LPS-induced nitric oxide production

Kim, Hye Mi; Kim, Su Jung; Kim, Hayeong; Ryu, Byeol; Kwak, Hokwang; Hur, Jonghyun; Choi, Jung‐Hye; Jang, Dae Sik

doi:10.1016/j.bmcl.2015.01.034

Cited by 39 publications

(20 citation statements)

References 16 publications

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“…Ailanthone Aila-11,20-Epoxy-1,11,12-trihydroxypicrasa-3,13(21)-diene-2,16dione] is a natural active compound isolated from the plant Ailanthus altissima (Bray et al, 1987). Aila has a wide spectrum of biological activities, it is traditionally used to treat ascariasis, diarrhoea, spermatorrhoea, bleeding and gastrointestinal diseases, and it has been found to have antiinflammatory activity (Kim et al, 2015). Aila inhibitory effect against several cancer cell lines (Wang R. et al, 2016), but the mechanisms involved in the antiproliferative activity of Aila are not completely elucidated and they seem to be related to the cancer cell type.…”

Section: Introductionmentioning

confidence: 99%

Ailanthone inhibits cell growth and migration of cisplatin resistant bladder cancer cells through down-regulation of Nrf2, YAP, and c-Myc expression.

et al. 2019

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Background: Ailanthone (Aila) is a natural active compound isolated from the Ailanthus altissima,-inhibitory effect against several cancer cell lines. Advanced bladder cancer is a common disease characterized by a frequent onset of resistance to cisplatin-based therapy. The cisplatin (CDDP) resistance is accompanied by an increase in Nrf2 protein expression which contributes to conferring resistance. Recently, we demonstrated a crosstalk between Nrf2 and YAP. YAP has also been demonstrated to play an important role in chemoresistance of bladder cancer. Purpose: We analyzed the antitumor effect of Aila in sensitive and CDDP-resistant bladder cancer cells and the molecular mechanisms involved in Aila activity. Study design: Sensitive and CDDP-resistant 253J B-V and 253J bladder cancer cells, and intrinsically CDDP-resistant T24 bladder cancer cells were used. Cells were treated with diverse concentrations of Aila and proliferation, cell cycle, apoptosis and gene expressions were determined. Methods: Aila toxicity and proliferation were determined by MTT and colony forming methods, respectively. Cell cycle was determined at cytofluorimeter by PI staining method Apoptosis was detected using Annexin V and PI double staining followed by quantitative flow cytometry. Expressions of Nrf2, Yap, c-Myc, and housekeeping genes were determined by western blot with specific antibodies. Cell migration was detected by wound healing and Boyden chamber analysis. Results: Aila inhibited growth of sensitive and CDDP-resistant bladder cancer cells with the same effectiveness, and reduced cell migration with higher effectiveness in CDDP resistant cells. Interestingly, Aila strongly reduced Nrf2 expression in all cell lines. Cell cycle analysis revealed an accumulation of Aila-treated cells in G0/G1 phase. Moreover, Aila significantly reduced YAP and c-Myc protein expression. The random and the oriented migration were strongly inhibited by Aila treatment, in particular in CDDP-resistant cells. Conclusions: Aila, inhibited proliferation and invasiveness of bladder cancer cells. Its high effectiveness in CDDP resistant cells could be related to the inhibition of Nrf2 , YAP and c-Myc expressions. Aila could represent a new tool to overcome CDDP resistance in bladder cancer.

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Section: Introductionmentioning

confidence: 99%

Ailanthone inhibits cell growth and migration of cisplatin resistant bladder cancer cells through down-regulation of Nrf2, YAP, and c-Myc expression.

et al. 2019

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“…observed IC50 value of 10.69 μM. By comparison with our previous study, two methoxy groups at C-3 and C-5 might be the bioactive groups for sinapaldehyde (9) [16]. Morever, sinapaldehyde (9) has shown significant inhibitory activity on TNF-α-induced NF-κB transcriptional activity in HepG2 cells, ascribing the symmetrical methoxyl group a more important role in NF-κB inhibition [32].…”

Section: Anti-inflammatory Activity Of Isolated Compounds 1-15 From Tmentioning

confidence: 49%

“…Among the isolates, sinapaldehyde (9) was found to have the most potent inhibitory effect with an observed IC 50 value of 5.92 µM, and erythro-guaiacylglycerol-β-O-4 1 -coniferyl ether (11) also showed a significant inhibitory effect with an observed IC 50 value of 10.69 µM. By comparison with our previous study, two methoxy groups at C-3 and C-5 might be the bioactive groups for sinapaldehyde (9) [16]. Morever, sinapaldehyde (9) has shown significant inhibitory activity on TNF-α-induced NF-κB transcriptional activity in HepG2 cells, ascribing the symmetrical methoxyl group a more important role in NF-κB inhibition [32].…”

Section: Anti-inflammatory Activity Of Isolated Compounds 1-15 From Tmentioning

confidence: 56%

“…Recently it was reported that some quassinoids from the stem barks of A. altissima inhibited the production of nitric oxide in RAW 264.7 cells [16]. In our continuing study to search for antiinflammatory agents from this plant, a new canthinone-type alkaloid (1), as well as 14 known compounds (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15), was isolated further from the EtOAc-and BuOH-soluble fractions of the EtOH extract of the stem barks of A. altissima (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle

et al. 2016

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Abstract:The present investigation of the chemical constituents of the stem barks of Ailanthus altissima has resulted in the isolation of six canthinone-type alkaloids, including a new compound, (R)-5-(1-hydroxyethyl)-canthine-6-one (1), and five known compounds (2-6). Moreover, four phenyl propanoids (7-10), two lignans (11 and 12), two triterpenoids (13 and 14) and a fatty acid (15) having previously known chemical structures were isolated during the same course of this study. The structure of the new compound was elucidated by physical (m.p., [α] D ) and spectroscopic data ( 1 H-NMR, 13 C-NMR, 2D NMR, and HR-DART-MS) interpretation and its absolute configuration was determined by electronic circular dichroism (ECD) data and quantum chemical calculations. The inflammatory activities of the isolates were screened on lipopolysaccharide (LPS)-induced nitric oxide (NO), a proinflammatory mediator, in RAW 264.7 cells. Among these isolated compounds, six compounds exhibited significant inhibition of NO production, with IC 50 values in the range of 5.92˘0.9 to 15.09˘1.8 µM.

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“…For example, Q. amara extracts showed significant inhibition of iNOS and COX-2 protein through prevention of nuclear translocation of NF-κB (Verma et al 2009). Studies on chemical constituent has identified that few quassinoids such as bruceines B and bruceines E from B. javanica (Liu et al 2012) and ailanthone from A. altissima (Kim et al 2015) displayed an active inhibitory effects on NO production. However, β-carbolines alkaloids isolated from P. quassioides were contributed to the antiinflammatory activities of the plant extract (Jiao et al 2011).…”

Section: Discussionmentioning

confidence: 99%

Evaluation of Antiinflammatory, Antioxidant and Antiproliferative Activities of Quassia borneensis Noot. (Simaroubaceae) Extracts

Kamarulzaman

Nuddin

Lim

et al. 2017

JSKM

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Constituents of the stem barks of Ailanthus altissima and their potential to inhibit LPS-induced nitric oxide production

Cited by 39 publications

References 16 publications

Ailanthone inhibits cell growth and migration of cisplatin resistant bladder cancer cells through down-regulation of Nrf2, YAP, and c-Myc expression.

Ailanthone inhibits cell growth and migration of cisplatin resistant bladder cancer cells through down-regulation of Nrf2, YAP, and c-Myc expression.

A New Canthinone-Type Alkaloid Isolated from Ailanthus altissima Swingle

Evaluation of Antiinflammatory, Antioxidant and Antiproliferative Activities of Quassia borneensis Noot. (Simaroubaceae) Extracts

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