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- Title
Epicochalasines A and B: Two Bioactive Merocytochalasans Bearing Caged Epicoccine Dimer Units from Aspergillus flavipes.
- Authors
Zhu, Hucheng; Chen, Chunmei; Tong, Qingyi; Li, Xiao‐Nian; Yang, Jing; Xue, Yongbo; Luo, Zengwei; Wang, Jianping; Yao, Guangmin; Zhang, Yonghui
- Abstract
Two bioactive merocytochalasans, epicochalasines A ( 1) and B ( 2), a new class of cytochalasans bearing unexpected scaffolds consisting of fused aspochalasin and epicoccine dimer moieties, were isolated from the liquid culture broth of Aspergillus flavipes. Both 1 and 2 possess a hendecacyclic 5/6/11/5/6/5/6/5/6/6/5 ring system containing an adamantyl cage and as many as 19 stereogenic centers; however, the fusion patterns of 1 and 2 differ greatly, thus resulting in different carbon skeletons. The absolute configurations of 1 and 2 were determined by X-ray diffraction and calculated ECD, respectively. The biogenetic pathways of 1 and 2 are proposed to involve Diels-Alder and nucleophilic addition reactions. Both 1 and 2 induced significant G2/M-phase cell-cycle arrest. Furthermore, we found that merocytochalasans induce apoptosis in leukemia cells through the activation of caspase-3 and the degradation of PARP.
- Subjects
CYTOCHALASINS; DIMERS; ASPERGILLUS flavus; DIELS-Alder reaction; NUCLEOPHILIC addition (Chemistry)
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 10, p3486
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201511315