Lycophlegmarinines A–F, new Lycopodium alkaloids from Phlegmariurus phlegmaria

Six new Lycopodium alkaloids, named lycophlegmarinines A–F (1–6), were isolated from whole plants of Phlegmariurus phlegmaria. Their structures were determined based on spectroscopic data analysis, quantum-chemical NMR calculations, and single-crystal X-ray crystallography. Lycophlegmarinine A (1) p...

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Bibliographic Details
Published in:Tetrahedron 2022-05, Vol.114, p.132782, Article 132782
Main Authors: Jiang, Jia-Meng, Xia, Dan, Zhu, Xin-Liu, Zhu, Dan, Yang, Xue-Wen, Pan, Ke
Format: Article
Language:English
Subjects:
Anti-acetylcholinesterase
Lycophlegmarinine
Lycopodium alkaloids
NMR calculations
Phlegmariurus phlegmaria
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Summary:Six new Lycopodium alkaloids, named lycophlegmarinines A–F (1–6), were isolated from whole plants of Phlegmariurus phlegmaria. Their structures were determined based on spectroscopic data analysis, quantum-chemical NMR calculations, and single-crystal X-ray crystallography. Lycophlegmarinine A (1) possesses a novel C15N skeleton with a 9/5/5 ring system, and its plausible biosynthetic pathway is proposed. Compounds 2 and 3 showed inhibitory activity against acetylcholinesterase, with IC50 values of 6.9 μM and 35.2 μM, respectively. [Display omitted] •Six new Lycopodium alkaloids were isolated from the whole plants of Phlegmariurus phlegmaria.•Compound 1 possesses a novel C15N skeleton with a 9/5/5 ring system.•Plausible biosynthetic pathway of 1 was speculated.•Compounds 2 and 3 showed inhibitory activity against acetylcholinesterase.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2022.132782