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从内生真菌中提取的三萜类化合物的结构解析及抗肿瘤活性

Structure Elucidation and Anti-Tumor Activities of Trichothecenes from Endophytic Fungus .

机构信息

Department of Medicinal Chemistry and Natural Medicine Chemistry, College of Pharmacy, Harbin Medical University, Harbin 150081, China.

Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China.

出版信息

Biomolecules. 2022 Jun 2;12(6):778. doi: 10.3390/biom12060778.

DOI:10.3390/biom12060778
PMID:35740903
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9220965/
Abstract

The secondary metabolites of , an endophytic fungus with anti-tumor activity isolated from Tsiang, were investigated. Five trichothecenes, including one previously undescribed metabolite, were isolated and identified. Their structures were elucidated by means of extensive spectroscopic methods; the absolute configuration of compound was determined by the ECD method. Surprisingly, 8-n-butyrylneosolaniol () exhibited stronger anti-tumor activity than T-2 toxin against Huh-7 cell line, with an IC value of 265.9 nM. 8-n-butyrylneosolaniol () promoted apoptosis induction in Huh-7 cells. Moreover, cell cycle analysis showed that cell cycle arrest caused by 8-n-butyrylneosolaniol () at the G2/M phase resulted in cell proliferation inhibition and pro-apoptotic activity. Further studies showed a significant decrease in mitochondrial membrane permeabilization and a significant increase in ROS generation, which led to the activation of caspase cascades and subsequent cleavage of PARP fragments. In conclusion, 8-n-butyrylneosolaniol () induced cell apoptosis in Huh-7 cells via the mitochondria-mediated apoptotic signaling pathway, which could be a leading compound for anti-tumor agents.

摘要

从蒋同兴分离得到的具有抗肿瘤活性的内生真菌中，研究了其次生代谢产物。分离并鉴定了五种单端孢霉烯族化合物，包括一种以前未描述的代谢产物。通过广泛的光谱方法阐明了它们的结构；通过 ECD 方法确定了化合物的绝对构型。令人惊讶的是，8-正丁酰基新茄病镰刀菌醇（）对 Huh-7 细胞系的抗肿瘤活性强于 T-2 毒素，IC 值为 265.9 nM。8-正丁酰基新茄病镰刀菌醇（）诱导 Huh-7 细胞凋亡。此外，细胞周期分析表明，8-正丁酰基新茄病镰刀菌醇（）在 G2/M 期引起的细胞周期阻滞导致细胞增殖抑制和促凋亡活性。进一步的研究表明，线粒体膜通透性显著降低，ROS 生成显著增加，导致 caspase 级联的激活和随后 PARP 片段的裂解。总之，8-正丁酰基新茄病镰刀菌醇（）通过线粒体介导的凋亡信号通路诱导 Huh-7 细胞凋亡，它可能是抗肿瘤药物的先导化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/6542f832f271/biomolecules-12-00778-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/ffb5206a43a8/biomolecules-12-00778-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/2abbd1dd2705/biomolecules-12-00778-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/354e52f2d67a/biomolecules-12-00778-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/6b0c88ce1abd/biomolecules-12-00778-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/4efb3f2268b4/biomolecules-12-00778-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/776f4a5af176/biomolecules-12-00778-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/6542f832f271/biomolecules-12-00778-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/ffb5206a43a8/biomolecules-12-00778-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/2abbd1dd2705/biomolecules-12-00778-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/354e52f2d67a/biomolecules-12-00778-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/6b0c88ce1abd/biomolecules-12-00778-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/4efb3f2268b4/biomolecules-12-00778-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/776f4a5af176/biomolecules-12-00778-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e565/9220965/6542f832f271/biomolecules-12-00778-g007.jpg

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