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Microascones, Decahydrofluorene-Class Alkaloids from the Marine-Derived Fungus Microascus sp. SCSIO 41821
Journal of Natural Products ( IF 5.1 ) Pub Date : 2024-03-01 , DOI: 10.1021/acs.jnatprod.3c00984
Fei-Hua Yao 1, 2 , Xiao Liang 1, 3 , Wen-Bin Shen 4 , Xin-Hua Lu 4 , Guo-Chao Li 4 , Shu-Hua Qi 1, 3
Affiliation  

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 (68), along with five known analogs (913) 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 1013 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 18 was also proposed.

中文翻译:

微囊泡素,来自海洋衍生真菌微囊泡菌属的十氢芴类生物碱。SCSIO 41821

八种新的十氢芴类生物碱,微囊果酮 A 和 B(12)、2,3-环氧磷马吡咯烷酮 C(3)、14,16-表子囊内酰胺 B(4)、24-羟基磷马吡咯烷酮 A(5)和微囊果酮 C–E ( 68 ) 以及五种已知的类似物 ( 913 ) 从海洋来源的真菌微子囊菌属中分离出来。SCSIO 41821。化合物12具有前所未有的复杂大环生物碱骨架,具有6/5/6/5/6/5/13多环系统。它们的结构和绝对构型通过光谱分析、ECD 光谱的量子化学计算和13 C NMR 化学位移确定。化合物10-13对PTPSig、PTP1B和CDC25B表现出选择性酶抑制活性,4、9和10对7测试的病原体表现出强抗菌活性讨论了它们的结构-生物活性关系,并提出了18的合理生物合成途径。
更新日期:2024-03-01
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