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Cytotoxic Physalins from Aeroponically Grown Physalis acutifolia
Journal of Natural Products ( IF 5.1 ) Pub Date : 2021-02-14 , DOI: 10.1021/acs.jnatprod.0c00380
Guo-Bo Xu 1 , Ya-Ming Xu 2 , E M Kithsiri Wijeratne 2 , Fatemeh Ranjbar 2 , Manping X Liu 2 , A A Leslie Gunatilaka 2
Affiliation  

Aeroponically grown Physalis acutifolia afforded five new and six known withanolides including 10 physalins. The structures of the new withanolides, acutifolactone (1), 5β,6β-epoxyphysalin C (2), 5α-chloro-6β-hydroxyphysalin C (3), and an inseparable mixture of 5β,6β-epoxy-2,3-dihydrophysalin F-3β-O-sulfate (4) and 5β,6β-epoxy-2,3-dihydrophysalin C-3β-O-sulfate (5), were elucidated by analysis of their spectroscopic data and chemical interconversions. The known withanolides were identified as physalins B (6), D (7), F (8), H (9), I (10), and U (11) by comparison of their spectroscopic data with those reported. Evaluation of 111 and the derivatives, 13 and 13a, obtained from 4 and 5 against a panel of four human cancer cell lines [NCI-H460 (non-small-cell lung), SF-268 (CNS glioma), PC-3 (prostate adenocarcinoma), and MCF-7 (breast adenocarcinoma)] and normal human lung fibroblast (WI-38) cells revealed that physalins 2, 3, 8, and 9 exhibited selective cytotoxic activity to at least one of the cancer cell lines tested compared to the normal cells and that 7, 10, and 11 were inactive up to a concentration of 10.0 μM. These data provided some preliminary structure–activity relationships and suggested that the mechanism of cytotoxic activity of physalins may differ from other classes of withanolides.

中文翻译:

来自气培生长的酸浆的细胞毒性酸浆

气培生长的酸浆提供了 5 种新的和 6 种已知的 withanolides,包括 10种酸浆。新的withanolides、acutifolactone ( 1 )、 5β,6β-epoxyphysalin C ( 2 )、 5α-chloro-6β-hydroxyphysalin C ( 3 ) 和不可分离的5β,6β-epoxy-2,3-dihydrophysalin 混合物的结构F-3β- O-硫酸盐 ( 4 ) 和 5β,6β-epoxy-2,3-dihydrophysalin C-3β- O-硫酸盐 ( 5 ) 通过光谱数据和化学互变分析得到阐明。已知的withanolides 被确定为physalins B ( 6 ), D ( 7 ), F ( 8 ), H ( 9 ))、I ( 10 ) 和 U ( 11 ) 通过将它们的光谱数据与报道的数据进行比较。评估111以及从45获得的衍生物1313a对一组四种人类癌细胞系 [NCI-H460(非小细胞肺)、SF-268(CNS 神经胶质瘤)、PC- 3(前列腺腺癌)和 MCF-7(乳腺腺癌)]和正常人肺成纤维细胞 (WI-38) 细胞显示,酸2389到癌细胞系中的至少一个显示出选择性的细胞毒活性测试的相比于正常细胞和710,和11无活性高达10.0μM的浓度。这些数据提供了一些初步的结构-活性关系,并表明 physalins 的细胞毒活性机制可能与其他类别的 withanolides 不同。
更新日期:2021-02-26
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