从海洋来源真菌sp. SCSIO F452中分离得到的三对新型螺环生物碱对映体

Three Pairs of New Spirocyclic Alkaloid Enantiomers From the Marine-Derived Fungus sp. SCSIO F452.

作者信息

Zhong Weimao, Wang Junfeng, Wei Xiaoyi, Fu Tingdan, Chen Yuchan, Zeng Qi, Huang Zhonghui, Huang Xinan, Zhang Weimin, Zhang Si, Long Lijuan, Wang Fazuo

机构信息

CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China.

College of Earth and Planetary Sciences, University of Chinese Academy of Sciences, Beijing, China.

出版信息

Front Chem. 2019 May 20;7:350. doi: 10.3389/fchem.2019.00350. eCollection 2019.

Three pairs of new spirocyclic alkaloid enantiomers eurotinoids A-C (-), as well as a known biogenetically related racemate dihydrocryptoechinulin D () were isolated from a marine-derived fungus sp. SCSIO F452. Their structures were determined by spectroscopic analyses and electronic circular dichroism (ECD) calculations. Compounds and represent the first two "" products from a non-stereoselective [4 + 2] Diels-Alder cycloaddition presumably between an enone group of a diketopiperazine alkaloid and a diene group of a benzaldehyde derivative via a new head-to-tail coupling mode biosynthetically, while and were "" products. Their enantiomers exhibited different antioxidative and cytotoxic activities. The modes of action were investigated by a preliminary molecular docking study.

从海洋来源的真菌Eurotium sp. SCSIO F452中分离出三对新的螺环生物碱对映体eurotinoids A-C（-），以及一种已知的生源相关外消旋体二氢隐棘霉素D（）。通过光谱分析和电子圆二色性（ECD）计算确定了它们的结构。化合物和代表了可能通过一种新的头对尾偶联模式生物合成的非对映选择性[4 + 2]狄尔斯-阿尔德环加成反应的前两个“”产物，该反应可能发生在二酮哌嗪生物碱的烯酮基团和苯甲醛衍生物的二烯基团之间，而和是“”产物。它们的对映体表现出不同的抗氧化和细胞毒性活性。通过初步的分子对接研究对作用模式进行了研究。