Linekosides C-E, three new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata
Linekosides C-E, three new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata
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DOI：
10.1016/j.bmc.2004.04.049
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发表时间：
2004-08-01
影响因子：
3.5
通讯作者：
Sakagami, Y
中科院分区：
文献类型：
--
作者：
Qi, JH;Ojika, M;Sakagami, Y
从冲绳海海星Linckia laevigata中分离得到三个新的甾体苷类化合物，命名为linckosides C-E。通过光谱法和化学衍生化方法确定了它们的结构和部分立体化学。这些代谢物是先前发现的一类新的致神经突化合物linckosides的额外成员。它们中的每一个在多羟基化甾体糖苷配基的C-3和侧链（C-28或C-29）处具有两个单糖单元。Linkosides C和D是第一个在侧链的C-24处具有羟基异丙基取代基的类固醇。这些化合物不仅是PC 12细胞上神经突生长的有效诱导剂，而且是神经生长因子（NGF）诱导神经突生长的显著增强剂。linckosides内的结构-活性关系表明，在侧链上的吡喃木糖的存在是重要的，而不是阿拉伯呋喃糖，但侧链碳骨架的多样性不是。(C)2004爱思唯尔有限公司保留所有权利。
Three new steroid glycosides, linckosides C-E, were isolated from the Okinawan starfish Linckia laevigata. Their structures and partial stereochemistry were elucidated by spectroscopic methods and chemical derivatization. These metabolites are additional members of the linckosides that were previously discovered as a novel class of neuritogenic compounds. Each of them possesses two monosaccharide units at C-3 of a polyhydroxylated steroidal aglycon and at the side chain (C-28 or C-29). Linckosides C and D are the first steroids that possess a hydroxyisopropyl substituent at C-24 of the side chain. These compounds are not only potent inducers of neurite outgrowth on PC12 cells but also significant enhancers of nerve growth factor (NGF) to induce the neurite outgrowth. The structure-activity relationships within the linckosides revealed that the presence of xylopyranose at the side chain was important rather than arabinofuranose, but that the diversity of the side chain carbon skeleton was not. (C) 2004 Elsevier Ltd. All rights reserved.