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Bipolarsterol A, a steroid with an unprecedented 6/5/6/5 carbon skeleton from the phytopathogenic fungus Bipolaris oryzae
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-12-19 , DOI: 10.1039/d4qo02057j
Meijia Zheng, Xiaotian Zhang, Xinran Zhang, Yingjie Liu, Qin Li, Lidan Mao, Weiguang Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu

Bipolarsterols A−H (18), eight undescribed steroids were isolated from Bipolaris oryzae, along with nine known congeners. Their structures and absolute configurations were elucidated by comprehensive spectroscopic techniques, NMR and ECD calculations. Compound 1 presents the first example of a 19(l0→5)-abeo-7(8→9)-abeo-ergostane, featuring an unusual spiro[4.5]decan-6-one system, and compound 2 is a new member of the rare steroid-phenylpropanoid hybrid. Compound 5 showed remarkable cytotoxicity against HT29 cells with an IC50 value of 5.8 μM. Compound 8 showed significant inhibitory effect on NO production in RAW264.7 with an IC50 value of 2.7 μM, through the inhibition of iNOS levels at the transcription and protein levels as well as the NF-κB pathway.

中文翻译:


双极甾醇 A,一种类固醇,具有前所未有的 6/5/6/5 碳骨架,来自植物病原真菌米极



米双极甾醇 A-H (1-8) 中分离出 8 种未描述的类固醇,以及 9 种已知的同系物。它们的结构和绝对构型通过综合光谱技术、NMR 和 ECD 计算阐明。化合物 1 提出了 19(l0→5)-abeo-7(8→9)-abeo-ergostane 的第一个例子,具有不寻常的螺[4.5]癸-6-酮系统,化合物 2 是稀有的类固醇-苯丙烷杂交的新成员。化合物 5 对 HT29 细胞具有显著的细胞毒性,IC50 值为 5.8 μM。化合物 8 对 RAW264.7 中 NO 的产生具有显着抑制作用,IC50 值为 2.7 μM,通过在转录和蛋白水平以及 NF-κB 通路抑制 iNOS 水平。
更新日期:2024-12-19
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