Hupserrine A, a Caged Lycopodium Alkaloid with a 6/6/5/6/7 Pentacyclic Skeleton from Huperzia serrata.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-07 DOI:10.1021/acs.orglett.5c02271

Shuai Jiang,Yu-Fei Ou,Wen-Yan Li,Zai-Feng Yuan,Xiao-Nian Li,Xiao Cheng,Qin-Shi Zhao

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.

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石杉碱A是一种笼型石杉属生物碱，具有6/6/5/6/7五环骨架。

石柏碱A(1)是石柏属生物碱，具有新颖的笼状6/6/5/6/7五环骨架。化合物1具有史无前例的2-氮杂四环[6.5.0.03,11.05,10]三烷烃单元。通过高分辨率电喷雾电离质谱（hresms）、核磁共振（NMR）和x射线衍射分析对其结构进行了分析。提出了一种可行的1的生物合成途径。化合物1对5-HT3AR具有显著的高选择性拮抗活性，IC50值为10.6±2.58 μM。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

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.