Microascones, Decahydrofluorene-Class Alkaloids from the Marine-Derived Fungus Microascus sp. SCSIO 41821

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-03-01 DOI:10.1021/acs.jnatprod.3c00984

Fei-Hua Yao, Xiao Liang, Wen-Bin Shen, Xin-Hua Lu, Guo-Chao Li and Shu-Hua Qi*,

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Abstract

Eight new decahydrofluorene-class alkaloids, microascones A and B (1 and 2), 2,3-epoxyphomapyrrolidone C (3), 14,16-epiascomylactam B (4), 24-hydroxyphomapyrrolidone A (5), and microascones C–E (6–8), along with five known analogs (9–13) were isolated from the marine-derived fungus Microascus sp. SCSIO 41821. Compounds 1 and 2 have an unprecedented complex macrocyclic alkaloid skeleton with a 6/5/6/5/6/5/13 polycyclic system. Their structures and absolute configurations were determined by spectroscopic analysis, quantum chemical calculations of ECD spectra, and ¹³C NMR chemical shifts. Compounds 10–13 showed selective enzyme inhibitory activity against PTPSig, PTP1B, and CDC25B, and 4, 9, and 10 exhibited strong antibacterial activity against seven tested pathogens. Their structure–bioactivity relationship was discussed, and a plausible biosynthetic pathway for 1–8 was also proposed.

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来自海洋真菌 Microascus sp. SCSIO 41821 的十氢芴类生物碱 Microascones

从海洋源真菌 Microascus sp. SCSIO 41821 中分离出了八种新的十氢芴类生物碱，即微囊苷 A 和 B（1 和 2）、2,3-环氧磷吡咯烷酮 C（3）、14,16-epiascomylactam B（4）、24-羟基磷吡咯烷酮 A（5）和微囊苷 C-E（6-8），以及五种已知的类似物（9-13）。化合物 1 和 2 具有前所未有的复杂大环生物碱骨架，其多环体系为 6/5/6/5/6/5/13。它们的结构和绝对构型是通过光谱分析、ECD 光谱的量子化学计算和 13C NMR 化学位移确定的。化合物 10-13 对 PTPSig、PTP1B 和 CDC25B 具有选择性酶抑制活性，而化合物 4、9 和 10 则对七种测试病原体具有很强的抗菌活性。研究人员讨论了这些化合物的结构与生物活性之间的关系，并提出了 1-8 化合物的合理生物合成途径。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.