Tripodalsporormielones A-C,unprecedented cage-like polyketides with complex polyvdent bridged and fused ring systems

• 作者: Guodong Chen Bingxin Zhao Meijuan Huang Jia Tang Yanbing Li Liangdong Guo Rongrong He Dan Hu Xinsheng Yao Hao Gao
• 来源期刊: 药学学报（英文版）
• 年，卷（期）: 2021,（11）
• 所属期刊栏目: Origimal articles
• 页码范围: 3648-3654
• 页数: 7页
• 语种: 英文

摘要

A chemical investigation on Sporormiella sp.led to the isolation and structural elucidation of tripodalsporormielones A-C(1-3),a new class of polyketide possessing unprecedented cage-like skel-etons with polyvdent bridged and fused ring systems.These polyketides with cage-like skeletons were characterized as a high non-protonated carbon-containing system,which resulted in few HMBC correla-tions observed and made the accurate structures hard to be obtained by NMR.Especially,some signals of non-protonated sp2 carbons are weak and even unobservable in compound 1.In order to establish the structure of 1,the calculated NMR with DP4 evaluation was applied to determine the structure from the plausible structure candidates obtained from the detailed NMR analysis.Based on NMR experiments and calculated NMR,the structures of isolated compounds were established and confirmed by X-ray tech-nology.Through chiral isolation,the optically pure enantiomers of 1 and 3 were obtained,and their ab-solute configurations were determined based on ECD quantum chemical calculation.Based on the isolated compounds and our previous work,1-3 would be derived from 3-methylorcinaldehyde,and their plausible biosynthetic mechanism was proposed.Furthermore,1 exhibited obvious short-term memory improvement activity on an Alzheimer's disease fly model.