AsperflavipineA: A Cytochalasan Heterotetramer Uniquely Defined by a Highly Complex Tetradecacyclic Ring System from Aspergillus flavipes QCS12
Zhu, Hucheng1; Chen, Chunmei1; Tong, Qingyi1; Yang, Jing2; Wei, Guangzheng1; Xue, Yongbo1; Wang, Jianping1; Luo, Zengwei1; Zhang, Yonghui1
2017-05-02
发表期刊ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷号56期号:19页码:5242-5246
摘要AsperflavipinesA (1) and B (2), two structurally complex merocytochalasans, were isolated from Aspergillus flavipes. AsperflavipineA (1), which contains two cytochalasan moieties and two epicoccine moieties, is the first cytochalasan heterotetramer to be discovered. It is uniquely defined by 5/6/11/5/6/5/6/5/6/5/5/11/6/5 fused tetradecacyclic rings with three continuous bridged ring systems. AsperflavipineB (2) is a cytochalasan heterotrimer containing a cytochalasan and two epicoccine moieties with a 5/6/11/5/5/6/5/6/5 nonacyclic ring system. The hypothetical biosynthesis of 1 and 2 is proposed to involve Diels-Alder and [3+2] cycloaddition reactions as key steps and reveals unparalleled plasticity in the biosynthesis of merocytochalasans. The existence of 1 adds a new dimension to the diversity of the cytochalasan family. Compound 1 showed moderate cytotoxicity and induced apoptosis in Jurkat, NB4, and HL60 cells through the activation of caspase-3 and degradation of poly(ADP-ribose) polymerase (PARP).
关键词Biological Activity Heterotetramers Heterotrimers Natural Products Structure Elucidation
资助信息National Natural Science Foundation of China(81573316; Changjiang Scholars Program; China Postdoctoral Science Foundation(2015M580647; 21602068; 2016T90695); 31370372; 21502057; 31570361; 31670354)
DOI10.1002/anie.201701125
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Multidisciplinary
WOS记录号WOS:000399951200013
引用统计
被引频次:10[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/51187
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Peoples R China
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Zhu, Hucheng,Chen, Chunmei,Tong, Qingyi,et al. AsperflavipineA: A Cytochalasan Heterotetramer Uniquely Defined by a Highly Complex Tetradecacyclic Ring System from Aspergillus flavipes QCS12[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017,56(19):5242-5246.
APA Zhu, Hucheng.,Chen, Chunmei.,Tong, Qingyi.,Yang, Jing.,Wei, Guangzheng.,...&Zhang, Yonghui.(2017).AsperflavipineA: A Cytochalasan Heterotetramer Uniquely Defined by a Highly Complex Tetradecacyclic Ring System from Aspergillus flavipes QCS12.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,56(19),5242-5246.
MLA Zhu, Hucheng,et al."AsperflavipineA: A Cytochalasan Heterotetramer Uniquely Defined by a Highly Complex Tetradecacyclic Ring System from Aspergillus flavipes QCS12".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.19(2017):5242-5246.
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