Amiaspochalasins A-H, Undescribed Aspochalasins with a C-21 Ester Carbonyl from Aspergillus micronesiensis
Amiaspochalasins A-H, Undescribed Aspochalasins with a C-21 Ester Carbonyl from Aspergillus micronesiensis
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Amiaspochalasins A-H，来自密克罗尼曲霉的具有 C-21 酯羰基的未描述的 Aspochalasins
DOI：
10.1021/acs.joc.9b00440
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发表时间：
2019
影响因子：
3.6
通讯作者：
Zhang Yonghui
中科院分区：
文献类型：
--
作者：
Wu Zhaodi;Zhang Xiaotian;Al Anbari Weaam Hasan;Zhang Mi;Chen Xia;Luo Zengwei;Li Xiao Nian;Chen Chunmei;Liu Junjun;Wang Jianping;Zhu Hucheng;Zhang Yonghui
Amiaspochalasins A-H(1-8)，8个未知的aspochalasins，和已知的类似物Trichalasin D(9)，是从曲霉固体培养物中分离得到的。化合物1-9是具有C-21酯基的松果体素，其结构经光谱分析、X-射线晶体分析、电子圆二色谱计算和化学方法确定。化合物1中的CH3-25位于C-16，而不是以前报道的aspochalasins中的C-14，赋予化合物1一个意想不到的碳骨架。化合物2和3是具有史无前例的5/6/6/8四环系统的松果体素的第一个例子。化合物4和5分别是松果体素I和J的非对映异构体。化合物6和7是第一个具有长开链体系的松果体素，通过比较化合物4和5的水解物和甲酯化产物的核磁共振数据，讨论了它们的绝对构型。化合物8是9的异构体。测定了1-9的细胞毒性和抑菌作用。
Amiaspochalasins A–H (1–8), eight undescribed aspochalasins, and trichalasin D (9), a known analogue, were isolated from the solid culture ofAspergillus micronesiensis. Compounds1–9are aspochalasins with a C-21 ester carbonyl, and their structures were determined by spectroscopic data, X-ray crystallographic analyses, electronic circular dichroism calculations, and chemical methods. The CH3-25 in compound1is located at C-16 rather than C-14 in the previously reported aspochalasins, endowing1with an unexpected carbon skeleton. Compounds2and3are the first examples of aspochalasins with an unprecedented 5/6/6/8 tetracyclic ring system. Compounds4and5are diastereomers of aspochalasins I and J, respectively. Compounds6and7are the first aspochalasins featuring a long open-chain system, and their absolute configurations were discussed by comparing the NMR data of the hydrolysis and methyl esterification products of4and5. Compound8is an isomeride of9. The cytotoxic and antimicrobial effects of1–9were tested.