Structural Elucidation and Total Synthesis of Trichodermotin A,A Natural α-Glucosidase Inhibitor from Trichoderma asperellum  

作　　者：Muyuan Yu Fengqing Wang Si Yao Yi Zang Chong Dai Yu Liang Mi Zhang Lianghu Gu Hucheng Zhu Yonghui Zhang 

机构地区：[1]Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation,School of Pharmacy,Tongji Medical College,Huazhong University of Science and Technology,Wuhan,Hubei,430030 China [2]National Institutes for Food and Drug Control(NIFDC),No.2,Tiantan Xili Dongcheng District,Beijing,100050 China

出　　处：《Chinese Journal of Chemistry》2022年第18期2219-2225,共7页中国化学（英文版）

基　　金：supported by the Program for Changiiang Scholars of Ministry of Education of the People's Republic of China(No.T2016088);the National Natural Science Foundation for Distinguished Young Scholars(No.81725021);the National Natural Science Foundation for Excellent Young Scholars(No.81922065);the Innovative Research Groups of the National Natural Science Foundation of China(No.81721005);the National Natural Science Foundation of China(No.81903461);the Science and Technology Major Project of Hubei Province(No.2021ACA012);the Research and Development Program of Hubei Province(No.2020BCA058);the Fundamental Research Funds for the Centural Universities(No.2019kfyXJJS168).

摘　　要：A pair of alkaloid enantiomers possessing a novel 1-oxaspiro[4.4]non-3-ene-2,7-dione skeleton,trichodermotin A(1),was obtained from the fungus Trichoderma asperellum.Spectroscopic data,X-ray diffraction,and ECD calculations were used to establish its structure and absolute configuration.(−)-1 showed significantα-glucosidase inhibitory activity(IC_(50)=10.1μmol/L vs.60.1μmol/L of positive control).A plausible biosynthetic pathway originating from L-β-phenylalanine was proposed,and a facile total synthesis was further accomplished.The key reaction of our synthetic strategy was a domino aza-Michael/lactonization in one pot,leading to the pivotal 4-amino-oxaspiro[4.4]octane scaffold.

关 键 词：Trichoderma asperellum ALKALOID α-Glucosidase inhibitory activity Molecular docking Total synthesis 

分 类 号：O62[理学—有机化学]