Lycoperine A, a novel C27N3-type pentacyclic alkaloid from Lycopodium hamiltonii, inhibiting acetylcholinesterase

被引：35

作者：

Hirasawa, Y ^{[1
]}

Kobayashi, J

Morita, H

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

[2] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 01期

关键词：

D O I：

10.1021/ol052760q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel C27N3-type pentacyclic Lycopodium alkaloid, lycoperine A (1) consisting of two octahydroquinoline rings and a piperidine ring, was isolated from the club moss Lycopodium hamiltonii. The structure and relative stereochemistry were elucidated on the basis of 2D NMR data and chemical transformation. Lycoperine A (1) exhibited an inhibitory activity against acetylcholinesterase.

引用

页码：123 / 126

页数：4

共 21 条

[11] Lyconadin A, a novel alkaloid from Lycopodium complanatum
Kobayashi, J
Hirasawa, Y
Yoshida, N
Morita, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) : 5901 - 5904
[12] Kobayashi Jun'ichi, 2005, Alkaloids Chem Biol, V61, P1, DOI 10.1016/S1099-4831(05)61001-2
[13] A revised structure for the piperidine alkaloid andrachamine
Mill, S
Hootele, C
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (12): : 2434 - 2443
[14] New phlegmarane-type, cernuane-type, and quinolizidine alkaloids from two species of Lycopodium
Morita, H
Hirasawa, Y
Shinzato, T
Kobayashi, J
[J]. TETRAHEDRON, 2004, 60 (33) : 7015 - 7023
[15] Himeradine A, a novel C27N3-type alkaloid from Lycopodium chinense
Morita, H
Hirasawa, Y
Kobayashi, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) : 4563 - 4566
[16] Serratezomines A-C, new alkaloids from Lycopodium serratum var. serratum
Morita, H
Arisaka, M
Yoshida, N
Kobayashi, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6241 - 6245
[17] Senepodine A, a novel C22N2 alkaloid from Lycopodium chinense
Morita, H
Hirasawa, Y
Yoshida, N
Kobayashi, J
[J]. TETRAHEDRON LETTERS, 2001, 42 (25) : 4199 - 4201
[18] Tandem radical cyclizations initiated with α-carbonyl radicals:: First total synthesis of (+)-paniculatine
Sha, CK
Lee, FK
Chang, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (42) : 9875 - 9876
[19] TOTAL SYNTHESIS OF THE LYCOPODIUM ALKALOIDS MAGELLANINE AND MAGELLANINONE BY 3-FOLD ANNULATION OF 2-CYCLOPENTENONE
WILLIAMS, JP
STLAURENT, DR
FRIEDRICH, D
PINARD, E
RODEN, BA
PAQUETTE, LA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) : 4689 - 4696
[20] Yen CF, 2002, ANGEW CHEM INT EDIT, V41, P4090, DOI 10.1002/1521-3773(20021104)41:21<4090::AID-ANIE4090>3.0.CO

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