The biologically and ecologically important natural products from the Chinese sea hare Bursatella leachii:structures,stereochemistry and beyond  

作　　者：ZHANG Xinyuan SU Mingzhi ZHU Mingxin CHEN Sha GAO Zhen GUO Yuewei LI Xuwen 

机构地区：[1]School of Chinese Materia Medica,Nanjing University of Chinese Medicine,Nanjing 210023,China [2]State Key Laboratory of Chemical Biology,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China [3]Shandong Laboratory of Yantai Drug Discovery,Bohai Rim Advanced Research Institute for Drug Discovery,Yantai 264117,China

出　　处：《Chinese Journal of Natural Medicines》2024年第11期1030-1039,共10页中国天然药物（英文版）

基　　金：supported by the National Key Research andDevelopment ProgramofChina(Nos.2021YFF0502400,2022YFC2804100);the Natural Science Foundation of China(Nos.82022069,42076099);Shandong Laboratory Program(No.SYS202205);the“Youth Innovation Promotion Association”of CAS(No.Y202065);the Fundamental Research Projects of Science&Technology In-novation and development Plan in Yantai City(No.2023JCYJ057);the CAS Youth Interdisciplinary Team,the Shandong Science and Technology Major Project of Innovation and Entrepreneurship Community with Antibodydrug(No.E321020);Youth Fund from Natural Science Foundation of Shandong Province(No.ZR2023QD162)。

摘　　要：A novel amide alkaloid,bursatamide A(1),featuring an unprecedented propyl-hexahydronaphthalene carbon frame-work,was isolated from the infrequently studied sea hare Bursatella leachi,alongside a new 3-phenoxypropanenitrile alkaloid,bursatellin B(2),and twelve known compounds.The structures of 1 and 2 were elucidated through comprehensive spectroscopic data analyses,while their relative and absolute configurations(ACs)were established through total synthesis and a series of quantum chem-ical calculations,including calculated electronic circular dichroism(ECD)spectra,optical rotatory dispersion(ORD)methods,and DP4^(+) probability analyses.Bursatamide A(1)demonstrated inhibitory effects against the human pathogenic bacteria Listeria monocyt-ogenes and Vibrio cholerae.Erythro-bursatellin B(21),a diastereoisomer of 2,exhibited notable antibacterial activity against the fish pathogenic bacterium Streptococcus parauberis FP KSP28,with an MIC90 value of 0.0472 μg·mL^(-1).

关 键 词：Bursatella leachii Marine natural product ALKALOID Sea hare Antibacterial activity 

分 类 号：R914[医药卫生—药物化学]