Targeted Isolation of Asperheptatides from a Coral-Derived Fungus Using LC-MS/MS-Based Molecular Networking and Antitubercular Activities of Modified Cinnamate Derivatives
Targeted Isolation of Asperheptatides from a Coral-Derived Fungus Using LC-MS/MS-Based Molecular Networking and Antitubercular Activities of Modified Cinnamate Derivatives
复制标题
使用基于 LC-MS/MS 的分子网络和修饰肉桂酸酯衍生物的抗结核活性，从珊瑚源真菌中靶向分离曲庚肽。
DOI：
10.1021/acs.jnatprod.0c00804
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发表时间：
2021-01-22
影响因子：
5.1
通讯作者：
Shao, Chang-Lun
中科院分区：
文献类型：
--
作者：
Chao, Rong;Hou, Xue-Mei;Shao, Chang-Lun
在MS/MS分子网络技术的指导下，从珊瑚真菌Aspergillus versicolor中分离得到4个新的环七肽，即asperheptatides A-D（1-4）和3个已知的类似物asperversiamide A-C（5-7）。通过综合光谱数据分析确定了两个主要化合物asperheptatides A和B（1和2）的平面结构。氨基酸残基的绝对构型用改进的马氏法确定。通过ESI-MS/MS裂解方法表征了两种结构相关的痕量代谢物，曲霉七肽C和D（3和4）。本文半合成了一系列新的曲霉酰胺A（5）衍生物（8-26）。还评价了化合物1、2和5-26对结核分枝杆菌H37 Ra的抗结核活性。化合物9、13、23和24显示出中等活性，MIC值为12.5 μ M，代表了一类潜在的新型抗结核药物。
Under the guidance of MS/MS-based molecular networking, four new cycloheptapeptides, namely, asperheptatides A-D (1-4), were isolated together with three known analogues, asperversiamide A-C (5-7), from the coral-derived fungus Aspergillus versicolor. The planar structures of the two major compounds, asperheptatides A and B (1 and 2), were determined by comprehensive spectroscopic data analysis. The absolute configurations of the amino acid residues were determined by advanced Marfey's method. The two structurally related trace metabolites, asperheptatides C and D (3 and 4), were characterized by ESI-MS/MS fragmentation methods. A series of new derivatives (8-26) of asperversiamide A (5) were semisynthesized. The antitubercular activities of 1, 2, and 5-26 against Mycobacterium tuberculosis H37Ra were also evaluated. Compounds 9, 13, 23, and 24 showed moderate activities with MIC values of 12.5 mu M, representing a potential new class of antitubercular agents.