{"title":"Bipolaristeroid A, a 5,6-seco-9,10-seco-steroid with cytotoxic activity from the fungus Bipolaris maydis.","authors":"Yong Shen, Lianghu Gu, Qun Zhou, Mengru Yu, Qin Li, Yu Liang, Chunmei Chen, Yonghui Zhang, Hucheng Zhu","doi":"10.1016/j.phytochem.2024.114303","DOIUrl":null,"url":null,"abstract":"<p><p>Eleven undescribed steroids, bipolaristeroids A-K, and one known compound, demethylincisterol A<sub>3</sub>, were isolated from the fungus Bipolaris maydis. Bipolaristeroid A is a 5,6-seco-9,10-seco-steroid with a rearranged B ring, in which the A and C rings are connected by an ester bond. Bipolaristeroid B is a rearranged 1(10→6)-abeosteroid with an aromatic B ring. Their planar structures and absolute configuration were determined using NMR, HRESIMS, DP4+ analysis, ECD calculation, and single-crystal X-ray diffraction. Bipolaristeroid A shows excellent inhibitory effects against the cancer cell lines HepG2, A549, SW620, and C4-2B with IC<sub>50</sub> values of 7.94, 5.11, 5.13, and 3.83 μM, respectively.</p>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1016/j.phytochem.2024.114303","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
Eleven undescribed steroids, bipolaristeroids A-K, and one known compound, demethylincisterol A3, were isolated from the fungus Bipolaris maydis. Bipolaristeroid A is a 5,6-seco-9,10-seco-steroid with a rearranged B ring, in which the A and C rings are connected by an ester bond. Bipolaristeroid B is a rearranged 1(10→6)-abeosteroid with an aromatic B ring. Their planar structures and absolute configuration were determined using NMR, HRESIMS, DP4+ analysis, ECD calculation, and single-crystal X-ray diffraction. Bipolaristeroid A shows excellent inhibitory effects against the cancer cell lines HepG2, A549, SW620, and C4-2B with IC50 values of 7.94, 5.11, 5.13, and 3.83 μM, respectively.
从真菌 Bipolaris maydis 中分离出了 11 种未曾描述过的类固醇（双极甾醇 A-K）和一种已知化合物（去甲基双极甾醇 A3）。双极性甾体 A 是一种 5,6-seco-9,10-seco-甾体，具有重新排列的 B 环，其中 A 环和 C 环通过酯键连接。双极性类固醇 B 是一种重新排列的 1(10→6)-类固醇，带有一个芳香的 B 环。利用核磁共振、HRESIMS、DP4+分析、ECD计算和单晶X射线二折射测定了它们的平面结构和绝对构型。双极性甾体A对HepG2、A549、SW620和C4-2B癌细胞株有很好的抑制作用，IC50值分别为7.94、5.11、5.13和3.83 μM。
期刊介绍：
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.
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