Symbioimine and neosymbioimine, amphoteric iminium metabolites from the symbiotic marine dinoflagellate Symbiodinium sp.*

被引：43
作者：
Kita, M
Ohishi, N
Washida, K
Kondo, M
Koyama, T
Yamada, K
Uemura, D [1 ]
机构：
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Grad Sch Sci, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2005年 / 13卷 / 17期
关键词：
symbioimine; neosymbioimine; iminium metabolite; inhibition of osteoclasts differentiation; COX-2;
D O I：
10.1016/j.bmc.2005.05.064
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Two amphoteric iminium metabolites, symbioimine (1) and neosymbioimine (2), were isolated from a cultivated symbiotic marine dinoflagellate Symbiodinium sp. Compounds I and 2 have a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. The plausible biogenetic pathway of I and 2 can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization. Symbioimine (1) inhibited the differentiation of RAW264 cells into osteoclasts (EC50 = 44 mu M), and significantly inhibited cyclooxygenase-2 activity at 10 mu M. Thus, symbioimine is a potent anti-resorptive and anti-inflammatory drug. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5253 / 5258
页数：6
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