Unusual chaetoglobosins and a new type of ferroptosis inducer from an endophytic fungus Chaetomium sp. UJN-EF006

IF 5.1 2区医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioorganic Chemistry Pub Date : 2025-05-01 Epub Date: 2025-03-06 DOI:10.1016/j.bioorg.2025.108342

Yin-Yin Wang , Yu-Song Wang , Jun-Jiang Li , Ze-Yi Wan , Hua Zhang

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Abstract

Seven unreported chaetoglobosin-type alkaloids, namely brachaetoglobosin A (1), chaetochalasins BF (2–6) and armochaeglobine C (7), together with the formerly described cytoglobosin C (8) and chaetoglobosin E (9), were obtained from an endophytic fungus Chaetomium sp. UJN-EF006 isolated from the leaves of Vaccinium bracteatum. Their structures were characterized through various spectral techniques including MS, NMR, X-ray crystallography and electronic circular dichroism. Also, this is only the second record of novel chaetochalasin and armochaeglobine skeletons of the cytochalasin super family, after 27 and 10 years of the first report, respectively. Compound 9 showed significant cytotoxic effect against two human tumor cell lines (MDA-MB231 and A549) and was identified as a new type of ferroptosis inducer (toward A549 cells) that could be used as a molecular tool in future related research.

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内生真菌Chaetomium sp. UJN-EF006中不同寻常的毛球蛋白和一种新型铁下沉诱导剂

从一种从苞片vacinium brteteatum叶片分离的内生真菌Chaetomium sp. ujt - ef006中分离得到7种未报道的毛球蛋白型生物碱，即brachaetoglobosin A(1)、chaetochalasins BF（2-6）和armochaegloine C(7)，以及先前报道的胞球蛋白C(8)和chaetoglobosin E(9)。通过质谱、核磁共振、x射线晶体学和电子圆二色等多种光谱技术对其结构进行了表征。此外，这是继第一次报道27年和10年之后，第二次记录细胞松弛素超家族的新型chatochalasin和armochaegloine骨架。化合物9对两种人肿瘤细胞系MDA-MB231和A549具有显著的细胞毒作用，是一种新型的（针对A549细胞的）铁下垂诱导剂，可作为今后相关研究的分子工具。

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来源期刊

Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

9.70

自引率

3.90%

发文量

679

审稿时长

31 days

期刊介绍： Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry. For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature. The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.