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来自土壤真菌粗糙卷枝毛霉的具有细胞毒性的细胞松弛素和苔色酸衍生物。

Cytochalasins and orsellinic acid derivatives with cytotoxicity from the soil-derived fungus Trichocladium asperum.

作者信息

Zhai Yi-Jie, Zhao Shu-Hui, Gao Jin-Ming, Han Wen-Bo

机构信息

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, China; College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi, China.

Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, China.

出版信息

Phytochemistry. 2025 Mar;231:114340. doi: 10.1016/j.phytochem.2024.114340. Epub 2024 Nov 26.

Abstract

Four undescribed cytochalasins (1-4), three undescribed orsellinic acid derivatives (5-7) and two known metabolites including methyl lecanorate (8) and methyl orsellinate (9) were isolated from the solid-state cultivation of a soil-derived fungus Trichocladium asperum SQ2-3 collected in Qinghai-Tibet Plateau. Their structures were elucidated by analysis of NMR (1D and 2D) and mass spectrometry data. The absolute configurations of 1-7 were assigned by a combination of the modified Mosher's method, microscale derivatization and Mo(OAc)-induced circular dichroism experiment. Compounds 1, 2, 3 and 6 showed significant cytotoxicity against HL-60, A3494, SMMC-7721, MDA-MB-231 and SW480 cell lines with IC values ranging from 4.74 to 15.84 μM, respectively. Meanwhile, compound 1 could obviously damage mitochondrial membrane potential and induce G2/M cell cycle arrest in A549 cells.

摘要

从青藏高原采集的土壤来源真菌粗糙枝霉(Trichocladium asperum)SQ2 - 3的固态培养物中分离得到了4种未描述的细胞松弛素(1 - 4)、3种未描述的苔色酸衍生物(5 - 7)以及2种已知代谢产物,包括落叶松萝酸甲酯(8)和苔色酸甲酯(9)。通过对核磁共振(一维和二维)及质谱数据的分析阐明了它们的结构。通过改良的莫舍尔法、微量衍生化和钼(乙酸盐)诱导圆二色性实验相结合的方法确定了1 - 7的绝对构型。化合物1、2、3和6对HL - 60、A3494、SMMC - 7721、MDA - MB - 231和SW480细胞系显示出显著的细胞毒性,IC值分别为4.74至15.84 μM。同时,化合物1可明显破坏A549细胞的线粒体膜电位并诱导G2/M期细胞周期阻滞。

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