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Increased cytotoxic potential of infrequent triterpenoid saponins of Cephalaria taurica obtained through alkaline hydrolysis
Phytochemistry ( IF 3.8 ) Pub Date : 2018-08-01 , DOI: 10.1016/j.phytochem.2018.04.015
Ozgur Ozer , Nazli Boke Sarikahya , Ayse Nalbantsoy , Suheyla Kirmizigul

Phytochemical investigations of the aerial parts of the plant Cephalaria taurica Szabó. (Caprifoliaceae) have resulted in the isolation of nine oleanane-type triterpenoid saponins, of which two still remain undescribed. The structures of tauricosides A and B were characterized based on NMR analysis, HRESIMS spectrometry, and chemical evaluations. The saponins tauricosides A and B have been rarely reported in the literature due to the presence of eight sugar moieties, and this is also the first report of saponins containing eight sugar moieties in the Caprifoliaceae family. The cytotoxic activities of tauricosides A and B, their undescribed prosapogenins, aglycone hederagenin, and n-butanol extract of C. taurica against the cancerous cells A-549, HeLa, PANC-1, and SH-SY5Y and the noncancerous HEK-293 cells were evaluated by the MTT method. Although tauricosides A and B and the crude n-butanol extract did not exhibit any activity at the tested concentrations on all the tested cells, after alkaline hydrolysis, the cytotoxic activity potential of the compounds was obviously improved. The most active compound, obtained after the alkaline hydrolysis of tauricoside B, showed a significant inhibitory effect, which was higher than that of the standard, commercially available drug doxorubicin, on the cancerous A-549, HeLa, PANC-1, and SH-SY5Y cells with IC50 values of 9.04, 8.75, 6.87, and 4.32 μM, respectively. In addition, prosapogenin, obtained after the alkaline hydrolysis of tauricoside A, exhibited considerable cytotoxic activity on the cancerous A-549, HeLa, PANC-1, and SH-SY5Y cells, with IC50 values of 13.19, 10.32, 11.91, and 7.49 μM, respectively. In conclusion, the alkaline hydrolysis of the saponins (tauricosides A and B) obviously improved their cytotoxic activity potential.

中文翻译:

通过碱性水解获得的稀有三萜皂苷的细胞毒性潜力增加

植物 Cephalaria taurica Szabó 地上部分的植物化学研究。(忍冬科)已分离出九种齐墩果烷型三萜皂苷,其中两种仍未被描述。基于 NMR 分析、HRESIMS 光谱法和化学评价表征了金黄苷 A 和 B 的结构。皂苷金黄皂苷A和B由于含有8个糖基,在文献中鲜有报道,这也是忍冬科含8个糖基的皂苷的首次报道。金牛黄苷 A 和 B、它们未描述的前皂苷元、糖苷元常春藤苷配基和正丁醇提取物对癌细胞 A-549、HeLa、PANC-1 和 SH-SY5Y 以及非癌性 HEK-293 细胞的细胞毒活性采用 MTT 法进行评价。尽管金牛黄苷A和B以及正丁醇粗提物在测试浓度下对所有测试细胞均未表现出任何活性,但碱水解后,化合物的细胞毒活性潜力明显提高。牛磺酸B碱水解后获得的活性最强的化合物对癌性A-549、HeLa、PANC-1和SH-表现出显着的抑制作用,其抑制作用高于标准的市售药物多柔比星。 SY5Y 细胞的 IC50 值分别为 9.04、8.75、6.87 和 4.32 μM。此外,牛磺苷 A 碱性水解后获得的前皂苷元对癌性 A-549、HeLa、PANC-1 和 SH-SY5Y 细胞表现出相当大的细胞毒活性,IC50 值为 13.19、10.32、11.91 和 7.49 μM , 分别。综上所述,
更新日期:2018-08-01
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