Sieboldine A, a novel tetracyclic alkaloid from Lycopoldium sieboldii, inhibiting acetylcholinesterase

Sieboldine A, a novel tetracyclic alkaloid from Lycopoldium sieboldii, inhibiting acetylcholinesterase
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DOI:
10.1021/ol035560s
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发表时间:
2003-10-16
期刊:
影响因子:
5.2
通讯作者:
Kobayashi, J
Kobayashi, J
中科院分区:
化学1区
文献类型:
--
作者:
Hirasawa, Y;Morita, H;Kobayashi, J

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从三叶草石蒜中分离到一种新的石蒜生物碱,该生物碱具有前所未有的融合四环环体系,由一个n -羟基的氮杂环壬烷环、一个环己酮、一个环戊酮和一个四氢呋喃环组成。利用二维核磁共振数据和x射线分析对其结构和相对立体化学性质进行了表征。Sieboldine A(1)表现出对乙酰胆碱酯酶的有效抑制活性和适度的细胞毒性。
A novel Lycopodium alkaloid with an unprecedented fused-tetracyclic ring system consisting of an aza-cyclononane ring having a N-hydroxy group, a cyclohexanone, a cyclopentanone, and a tetrahydrofuran ring, sieboldine A (1), was isolated from the club moss Lycopodium sieboldii. The structure and relative stereochemistry were elucidated on the basis of 2D NMR data and X-ray analysis. Sieboldine A (1) exhibited a potent inhibitory activity against acetylcholinesterase and modest cytotoxicity.