Neocomplanines A and B, a Complanine Family Isolated from the Marine Fireworm

Neocomplanines A and B, a Complanine Family Isolated from the Marine Fireworm
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DOI:
10.1021/np900694j
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发表时间:
2010-03-01
影响因子:
5.1
通讯作者:
Uemura, Daisuke
Uemura, Daisuke
中科院分区:
生物学2区
文献类型:
--
作者:
Nakamura, Kazuhiko;Tachikawa, Yu;Uemura, Daisuke

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沙蚕碱家族的两个新成员,新沙蚕碱 A (2) 和 B (3),作为“海洋火虫”Eurythoe complanata 甲醇提取物的次要成分被分离出来。通过光谱分析,新沙蚕素的结构被揭示为具有饱和碳链的三甲基铵单元。以环氧氯丙烷为起始原料,通过全合成成功证实了新沙蚕素A和B的平面结构。在体外存在 Ca(2+) 的情况下,新沙蚕素显示出炎症活性,并且与 TPA 结合可增强 PKC 活性;两者都与Complanine (1) 的作用相似。讨论了沙蚕碱相关化合物作用的分子机制。
Two new members of the complanine family, neocomplanines A (2) and B (3), were isolated as minor components of the methanolic extract of the "marine fireworm" Eurythoe complanata. The structures of the neocomplanines were revealed spectroscopically to be a trimethylammonium unit with a saturated carbon chain. The planar structures of neocomplanines A and B were confirmed successfully through total syntheses that used epichlorohydrin as a starting material. The neocomplanines show inflammatory activity and also enhanced PKC activity in combination with TPA in the presence of Ca(2+) in vitro; both arc similar to the effects of complanine (1). The molecular mechanism of the effects of complanine-related compounds is discussed.