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- Title
Asperchalasine A, a Cytochalasan Dimer with an Unprecedented Decacyclic Ring System, from Aspergillus flavipes.
- Authors
Zhu, Hucheng; Chen, Chunmei; Xue, Yongbo; Tong, Qingyi; Li, Xiao‐Nian; Chen, Xintao; Wang, Jianping; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui
- Abstract
Asperchalasine A ( 1), the first cytochalasan dimer featuring a unique decacyclic 5/6/11/5/5/6/5/11/6/5 ring system consisting of 20 chiral centers, was isolated from the culture broth of Aspergillus flavipes. Three biogenetically related intermediates, asperchalasines B-D ( 2- 4), were also isolated. Their structures, including their absolute configurations, were elucidated using a combination of HRESIMS, NMR, ECD, molecular modeling, and single-crystal X-ray diffraction techniques. Compound 1, which possesses an unprecedented 13-oxatetracyclo[7.2.1.12,5.01,6]tridec-8,12-dione core structure, is the first example of a dimeric cytochalasan alkaloid. The biogenetic pathways of 1- 4 were described starting from the co-isolated compounds 5 and 6. More importantly, 1 induced significant G1-phase cell cycle arrest by selectively inhibiting cyclin A, CDK2 and CDK6 in cancerous, but not normal, cells, highlighting it as a potentially selective cell cycle regulator against cancer cells.
- Subjects
DIMERS; OLIGOMERS; ASPERGILLUS; X-ray diffraction; CANCER cells
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 45, p13374
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201506264