Complanadine B, obscurumines A and B, new alkaloids from two species of Lycopodium

被引：52

作者：

Morita, H

Ishiuchi, K

Haganuma, A

Hoshino, T

Obara, Y

Nakahata, N

Kobayashi, J ^{[1
]}

机构：

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

[2] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2005年 / 61卷 / 08期

关键词：

Lycopodium; alkaloid; dimer; neurotrophic factors; astrocytoma cells;

D O I：

10.1016/j.tet.2005.01.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new dirtier of C16N2 type alkaloid, complanadine B (1), and two new C16N type alkaloids, obscurumines A (2) and B (3), have been isolated from the club moss Lycopodium complanatum and L obscurum, respectively. The structures and stereochemistry of 1-3 were elucidated by combination of 2D NMR spectra and chemical transformation. Complanadine A (4) isolated together with 1 induced secretion of neurotrophic factors from human astrocytoma cells. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1955 / 1960

页数：6

共 39 条

[11] 2-I
[12] A classical paradigm of alkaloid biogenesis revisited: Acetonedicarboxylic acid as a biosynthetic precursor of lycopodine
Hemscheidt, T
Spenser, ID
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) : 1799 - 1800
[13] BIOSYNTHESIS OF LYCOPODINE - INCORPORATION OF ACETATE VIA AN INTERMEDIATE WITH C(2V)SYMMETRY
HEMSCHEIDT, T
SPENSER, ID
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) : 3020 - 3021
[14] Nankakurine A, a novel C16N2-type alkaloid from Lycopodium hamiltonii
Hirasawa, Y
Morita, H
Kobayashi, J
[J]. ORGANIC LETTERS, 2004, 6 (19) : 3389 - 3391
[15] Sieboldine A, a novel tetracyclic alkaloid from Lycopoldium sieboldii, inhibiting acetylcholinesterase
Hirasawa, Y
Morita, H
Shiro, M
Kobayashi, J
[J]. ORGANIC LETTERS, 2003, 5 (21) : 3991 - 3993
[16] Senepodines B-E, new C22N2 alkaloids from Lycopodium chinense
Hirasawa, Y
Morita, H
Kobayashi, J
[J]. TETRAHEDRON, 2003, 59 (20) : 3567 - 3573
[17] Lyconesidines A-C, new alkaloids from Lycopodium chinense
Hirasawa, Y
Morita, H
Kobayashi, J
[J]. TETRAHEDRON, 2002, 58 (27) : 5483 - 5488
[18] 1ST TOTAL SYNTHESIS OF LYCOPODIUM ALKALOIDS OF THE MAGELLANANE GROUP - ENANTIOSELECTIVE TOTAL SYNTHESES OF (-)-MAGELLANINE AND (+)-MAGELLANINONE
HIRST, GC
JOHNSON, TO
OVERMAN, LE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) : 2992 - 2993
[19] Kaiser E., 1954, MONATSH CHEM, V85, P896
[20] Complanadine A, a new dimeric alkaloid from Lycopodium complanatum
Kobayashi, J
Hirasawa, Y
Yoshida, N
Morita, H
[J]. TETRAHEDRON LETTERS, 2000, 41 (47) : 9069 - 9073

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