Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College , Huazhong University of Science and Technology , Wuhan 430030 , Hubei Province , People's Republic of China.
J Org Chem. 2019 May 3;84(9):5483-5491. doi: 10.1021/acs.joc.9b00440. Epub 2019 Apr 25.
Amiaspochalasins A-H (1-8), eight undescribed aspochalasins, and trichalasin D (9), a known analogue, were isolated from the solid culture of Aspergillus micronesiensis. Compounds 1-9 are 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 CH-25 in compound 1 is located at C-16 rather than C-14 in the previously reported aspochalasins, endowing 1 with an unexpected carbon skeleton. Compounds 2 and 3 are the first examples of aspochalasins with an unprecedented 5/6/6/8 tetracyclic ring system. Compounds 4 and 5 are diastereomers of aspochalasins I and J, respectively. Compounds 6 and 7 are 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 of 4 and 5. Compound 8 is an isomeride of 9. The cytotoxic and antimicrobial effects of 1-9 were tested.
阿米阿索查林 A-H（1-8）、八种未描述的阿索查林和三爪素 D（9）是从米氏曲霉的固体培养物中分离得到的。化合物 1-9 是具有 C-21 酯羰基的阿索查林，其结构通过光谱数据、X 射线晶体学分析、电子圆二色性计算和化学方法确定。化合物 1 中的 CH-25 位于 C-16 而不是先前报道的阿索查林中的 C-14，这使 1 具有意想不到的碳骨架。化合物 2 和 3 是具有前所未有的 5/6/6/8 四环系统的阿索查林的第一个例子。化合物 4 和 5 分别是阿索查林 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系统的阿索查林，通过比较 4 和 5 的水解和甲酯化产物的 NMR 数据讨论了它们的绝对构型。化合物 8 是 9 的异构体。测试了 1-9 的细胞毒性和抗菌作用。
