Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A, and 3,4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp.

被引：35

作者：

Yamada, Mika ^{[1
]}

Takahashi, Yohei ^{[1
]}

Kubota, Takaaki ^{[1
]}

Fromont, Jane ^{[2
]}

Ishiyama, Aki ^{[3
,4
]}

Otoguro, Kazuhiko ^{[3
,4
]}

Yamada, Haruki ^{[3
,4
]}

Omura, Satoshi ^{[3
,4
]}

Kobayashi, Jun'ichi ^{[1
]}

机构：

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

[2] Western Australian Museum, Welshpool Dc, WA 6986, Australia

[3] Kitasato Univ, Res Ctr Trop Dis, Kitasato Inst, Minato Ku, Tokyo 1088641, Japan

[4] Kitasato Univ, Kitasato Inst Life Sci, Kitasato Inst, Minato Ku, Tokyo 1088641, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 11期

关键词：

Sponge; Manzamine alkaloid; Zamamidine C; 3,4-Dihydro-6-hydroxy-10,11-epoxymanzamine A; 3,4-Dihydromanzamine J N-oxide; Antitrypanosomal activity; Antimalarial activity; MARINE NATURAL-PRODUCTS;

D O I：

10.1016/j.tet.2009.01.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New manzamine alkaloids, zamamidine C (1), 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2), and 3,4-dihydromanzamine J N-oxide (3). have been isolated from an Okinawan marine sponge Amphimedon species. The Structures and stereochemistries of 1-3 were elucidated from the spectroscopic data and chemical derivatization. Zamamidine C (1) is a new manzamine alkaloid possessing a second beta-carboline ring via an ethylene unit at N-2 of manzamine D, while 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2) is the first manzamine alkaloid possessing an epoxide ring at C-10 and C-11. Zamamidine C (1) showed significant antitrypanosomal activity against Trypanosoma brucei brucei, the parasite associated with sleeping sickness, and antimalarial activity against Plasmodium falciparum, the causative agent of malaria in vitro. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2313 / 2317

页数：5