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

被引:84
作者
Hirasawa, Y [1 ]
Morita, H
Shiro, M
Kobayashi, J
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Rigaku Corp, Xray Res Lab, Tokyo 1968666, Japan
关键词
D O I
10.1021/ol035560s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:3991 / 3993
页数:3
相关论文
共 28 条
  • [1] Ayer W.A., 1994, ALKALOIDS, V45, P233, DOI DOI 10.1016/S0099-9598(08)60278-3
  • [2] ALKALOIDS OF LYCOPODIUM-ALOPECUROIDES L .5. STRUCTURE OF ALOPECURIDINE
    AYER, WA
    ALTENKIRK, B
    FUKAZAWA, Y
    [J]. TETRAHEDRON, 1974, 30 (23-2) : 4213 - 4214
  • [3] THE LYCOPODIUM ALKALOIDS
    AYER, WA
    [J]. NATURAL PRODUCT REPORTS, 1991, 8 (05) : 455 - 463
  • [4] Huperzine A, a potential therapeutic agent for treatment of Alzheimer's disease
    Bai, DL
    Tang, XC
    He, XC
    [J]. CURRENT MEDICINAL CHEMISTRY, 2000, 7 (03) : 355 - 374
  • [5] Cassayre K, 2002, ANGEW CHEM INT EDIT, V41, P1783, DOI 10.1002/1521-3773(20020517)41:10<1783::AID-ANIE1783>3.0.CO
  • [6] 2-I
  • [7] Model studies toward the total synthesis of the Lycopodium alkaloid spirolucidine
    Comins, DL
    Williams, AL
    [J]. ORGANIC LETTERS, 2001, 3 (20) : 3217 - 3220
  • [8] IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids:: Asymmetric synthesis of (+)-luciduline
    Comins, DL
    Brooks, CA
    Al-awar, RS
    Goehring, RR
    [J]. ORGANIC LETTERS, 1999, 1 (02) : 229 - 231
  • [9] Asymmetric synthesis of the Lycopodium alkaloid, Na-acetyl-Nb-methylphlegmarine
    Comins, DL
    Libby, AH
    Al-awar, RS
    Foti, CJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) : 2184 - 2185
  • [10] Grierson D., 1990, Org. React, V39, P85, DOI [10.1002/0471264180.or039.02, DOI 10.1002/0471264180.OR039.02]