Bipolarsterol A, a steroid with an unprecedented 6/5/6/5 carbon skeleton from the phytopathogenic fungus Bipolaris oryzae†

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-08 DOI:10.1039/d4qo02057j

Meijia Zheng , Xiaotian Zhang , Xinran Zhang , Yingjie Liu , Qin Li , Lidan Mao , Weiguang Sun , Chunmei Chen , Yonghui Zhang , Hucheng Zhu

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Abstract

Bipolarsterols A–H (), eight undescribed steroids, were isolated from Bipolaris oryzae, along with nine known congeners. Their structures and absolute configurations were elucidated by comprehensive spectroscopic techniques, including NMR and ECD calculations. Compound represents 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 is a new member of the rare steroid-phenylpropanoid hybrid class. Compound showed remarkable cytotoxicity against HT29 cells with an IC₅₀ value of 5.8 μM. Compound showed a 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 transcriptional and protein levels as well as the NF-κB pathway.

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双极甾醇A，一种史无前例的具有6/5/6/5碳骨架的甾体化合物，来自植物病原真菌双极真菌

双极甾醇A−H(1−8)，8个未描述的甾体，以及9个已知的同源物。通过综合波谱技术、核磁共振和ECD计算对它们的结构和绝对构型进行了分析。化合物1是19(10→5)-abeo-7(8→9)-abeo-麦角甾烷的第一个例子，具有不寻常的螺旋[4.5]癸烷-6- 1体系，化合物2是罕见的类固醇-苯丙烷杂化物的新成员。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通过抑制转录和蛋白水平的iNOS水平以及NF-κB通路，对RAW264.7的NO生成有显著抑制作用，IC50值为2.7 μM。

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Organic chemistry frontiers : an international journal of organic chemistry

CiteScore

7.80

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0.00%

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