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通过液相色谱-串联质谱引导,从来源于 的内生真菌TE-739D中发现两种新的环己缩肽——日本酰胺C和D。

LC-MS/MS-guided discovery of japonamides C and D, two new cyclohexadepsipeptides, from the -derived endophytic fungus TE-739D.

作者信息

Wang Haisu, Hao Xianwei, Dong Chen, Yuan Xiaolong, Zhang Peng, Gu Gan

机构信息

Research Center for Plant Functional Components, Tobacco Research Institute of Chinese Academy of Agricultural Sciences, Qingdao, China.

Technological Center, China Tobacco Zhejiang Industrial Co., Ltd., Hangzhou, China.

出版信息

Front Microbiol. 2025 May 8;16:1595569. doi: 10.3389/fmicb.2025.1595569. eCollection 2025.

DOI:10.3389/fmicb.2025.1595569
PMID:40406348
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12095196/
Abstract

Endophytic fungi belonging to the genus have received substantial attention due to their notable secondary metabolic potential. In this study, chemical investigations using LC-MS/MS-based molecular networking on the endophytic fungus TE-739D led to the discovery of two new cyclohexadepsipeptides, namely japonamides C () and D (), along with three known cyclodipeptides (-). Their structures, including the absolute configurations of the amino acid residues, were elucidated through spectroscopic data analysis and an optimized Marfey's method. The newly discovered compounds, japonamides C () and D (), were screened for broad-spectrum cell proliferation inhibitory activity against 20 different human cell lines. The results indicated that both compounds displayed broad-spectrum antiproliferative activity against MKN-45, HCT116, TE-1, 5,637, CAL-62, and A-637 cells, with inhibition rates ranging from 55.0 to 72.3%. Moreover, the antibacterial activity of compounds - against two Gram-positive bacteria and two Gram-negative bacteria was also evaluated.

摘要

该属内生真菌因其显著的次生代谢潜力而受到广泛关注。在本研究中,对内生真菌TE - 739D进行基于液相色谱-串联质谱的分子网络化学研究,发现了两种新的环己缩肽,即日本酰胺C( )和D( ),以及三种已知的环二肽( - )。通过光谱数据分析和优化的马尔费伊法阐明了它们的结构,包括氨基酸残基的绝对构型。对新发现的化合物日本酰胺C( )和D( )进行了针对20种不同人类细胞系的广谱细胞增殖抑制活性筛选。结果表明,这两种化合物对MKN - 45、HCT116、TE - 1、5637、CAL - 62和A - 637细胞均表现出广谱抗增殖活性,抑制率在55.0%至72.3%之间。此外,还评估了化合物 - 对两种革兰氏阳性菌和两种革兰氏阴性菌的抗菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/05637459ee51/fmicb-16-1595569-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/a51bc2f04771/fmicb-16-1595569-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/2322315ae05a/fmicb-16-1595569-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/529f451ca7ec/fmicb-16-1595569-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/f12d79ea13f7/fmicb-16-1595569-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/fc6dc958feb6/fmicb-16-1595569-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/05637459ee51/fmicb-16-1595569-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/a51bc2f04771/fmicb-16-1595569-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/2322315ae05a/fmicb-16-1595569-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/529f451ca7ec/fmicb-16-1595569-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/f12d79ea13f7/fmicb-16-1595569-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/fc6dc958feb6/fmicb-16-1595569-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d962/12095196/05637459ee51/fmicb-16-1595569-g005.jpg

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本文引用的文献

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Cyclopeptide Avellanins D-O with Antimalarial Activity from the Mariana Trench Anemone-Derived MSC5.来自马里亚纳海沟海葵衍生的MSC5的具有抗疟活性的环肽Avellanins D - O
J Nat Prod. 2024 Dec 27;87(12):2695-2708. doi: 10.1021/acs.jnatprod.4c00740. Epub 2024 Nov 27.
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Ergone Derivatives from the Deep-Sea-Derived Fungus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells.
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