Two new steroids with cytotoxicities from fungus Acrocalymma cycadis

IF 1.3 4区生物学 Q4 CHEMISTRY, MEDICINAL

Phytochemistry Letters Pub Date : 2024-06-01 DOI:10.1016/j.phytol.2024.03.014

Li-Bin Lin , Deng-Gao Zhu , Ting Yang , Rui Han , Jia-Yao Hu , Wei Shi , Ze-Yi Li , Xiao-Ling Wang , Jian Xiao

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Abstract

Thirteen steroids (1–13), including two undescribed steroids, acrocalysterol C (1) and acrocalysterol D (2), were isolated from cultures of the fungus Acrocalymma cycadis using the OSMAC approach. Compounds 1 and 2 represent highly oxygenated steroids that contain an epoxy fragment. Through NMR and HRESIMS analyses, quantum chemical calculations, and electronic circular dichroism (ECD) experiments, their structures and absolute configurations were characterized. Then, the in vitro cytotoxicity of each compound was evaluated. Compounds 4 and 8-10 exhibited remarkable cytotoxicities against HeLa cells. Obviously, compound 10 exhibited twofold greater activity against HeLa than positive control, with IC₅₀ values of 13.2 ± 1.23 μM. Additionally, compound 2 presented moderate potent cytotoxicity activities against three human cancer cells, comparable to the positive control. Thus, the bioactive metabolites of the strain A. cycadis may serve as a novel resource for development.

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来自苏铁真菌的两种具有细胞毒性的新类固醇

利用 OSMAC 方法从苏铁真菌 Acrocalymma cycadis 的培养物中分离出 13 种类固醇（1-13），其中包括两种未曾描述过的类固醇，即 Acrocalysterol C (1) 和 Acrocalysterol D (2)。化合物 1 和 2 代表含有环氧片段的高含氧类固醇。通过核磁共振和 HRESIMS 分析、量子化学计算和电子圆二色性（ECD）实验，确定了它们的结构和绝对构型。然后，对每种化合物的体外细胞毒性进行了评估。化合物 4 和 8-10 对 HeLa 细胞具有显著的细胞毒性。很明显，化合物 10 对 HeLa 的活性是阳性对照的两倍，其 IC50 值为 13.2 ± 1.23 μM。此外，化合物 2 对三种人类癌细胞具有中等程度的细胞毒性活性，与阳性对照相当。因此，苏铁菌株的生物活性代谢物可作为一种新的开发资源。

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来源期刊

Phytochemistry Letters 生物-生化与分子生物学

CiteScore

3.00

自引率

11.80%

发文量

190

审稿时长

34 days

期刊介绍： Phytochemistry Letters invites rapid communications on all aspects of natural product research including: • Structural elucidation of natural products • Analytical evaluation of herbal medicines • Clinical efficacy, safety and pharmacovigilance of herbal medicines • Natural product biosynthesis • Natural product synthesis and chemical modification • Natural product metabolism • Chemical ecology • Biotechnology • Bioassay-guided isolation • Pharmacognosy • Pharmacology of natural products • Metabolomics • Ethnobotany and traditional usage • Genetics of natural products Manuscripts that detail the isolation of just one new compound are not substantial enough to be sent out of review and are out of scope. Furthermore, where pharmacology has been performed on one new compound to increase the amount of novel data, the pharmacology must be substantial and/or related to the medicinal use of the producing organism.