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 

机构地区：[1]Institute of Traditional Chinese Medicine&Natural Products,College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research,Jinan University,Guangzhou 510632,China [2]Department of Chemistry,College of Chemistry and Materials Science,Jinan University,Guangzhou 510632,China [3]Guangdong Engineering Research Center of Chinese Medicine&Disease Susceptibility,Jinan University,Guangzhou 510632,China [4]State Key Laboratory of Mycology,Institute of Microbiology,Chinese Academy of Sciences,Beijing 100190,China

出　　处：《Acta Pharmaceutica Sinica B》2021年第11期3648-3654,共7页药学学报（英文版）

基　　金：financially supported by grants from National Key Research and Development Program of China(2018YF A0903200/2018YFA0903201);the National Natural Science Foundation of China(81925037 and 81973213);Chang Jiang Scholars Program(Young Scholar)from the Ministry of Education of China(Hao Gao,2017);National High-level Personnel of Special Support Program(2017RA2259,China);the 111 Project of Ministry of Education of the People’s Republic of China(B13038);the Guangdong Natural Science Funds for Distinguished Young Scholar(2017A03036027,China);Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(2017BT01Y036,China);K.C.Wong Education Foundation(Hao Gao,2016,China)。

摘　　要：A chemical investigation on Sporormiella sp.led to the isolation and structural elucidation of tripodalsporormielones Ae C(1-3),a new class of polyketide possessing unprecedented cage-like skeletons 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 correlations observed and made the accurate structures hard to be obtained by NMR.Especially,some signals of non-protonated sp;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 technology.Through chiral isolation,the optically pure enantiomers of 1 and 3 were obtained,and their absolute 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.

关 键 词：Tripodalsporormielones Cage-like polyketides 3-Methylorcinaldehyde Alzheimer’s disease 

分 类 号：R284[医药卫生—中药学]