{"title":"Hupserrine A, a Caged Lycopodium Alkaloid with a 6/6/5/6/7 Pentacyclic Skeleton from Huperzia serrata.","authors":"Shuai Jiang,Yu-Fei Ou,Wen-Yan Li,Zai-Feng Yuan,Xiao-Nian Li,Xiao Cheng,Qin-Shi Zhao","doi":"10.1021/acs.orglett.5c02271","DOIUrl":null,"url":null,"abstract":"Hupserrine A (1), a Lycopodium alkaloid featuring a novel caged 6/6/5/6/7 pentacyclic skeleton, was isolated from Huperzia serrata. Compound 1 possesses an unprecedented 2-azatetracyclo[6.5.0.03,11.05,10]tridecane unit. Its structure was elucidated by high-resolution electrospray ionization mass spectrometry (HRESIMS), nuclear magnetic resonance (NMR), and X-ray diffraction analyses. A plausible biosynthetic pathway for 1 is proposed. Compound 1 demonstrated significant and highly selective antagonistic activity against the 5-HT3AR with an IC50 value of 10.6 ± 2.58 μM.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"30 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-07-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c02271","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Hupserrine A (1), a Lycopodium alkaloid featuring a novel caged 6/6/5/6/7 pentacyclic skeleton, was isolated from Huperzia serrata. Compound 1 possesses an unprecedented 2-azatetracyclo[6.5.0.03,11.05,10]tridecane unit. Its structure was elucidated by high-resolution electrospray ionization mass spectrometry (HRESIMS), nuclear magnetic resonance (NMR), and X-ray diffraction analyses. A plausible biosynthetic pathway for 1 is proposed. Compound 1 demonstrated significant and highly selective antagonistic activity against the 5-HT3AR with an IC50 value of 10.6 ± 2.58 μM.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.