Synthesis and biological properties of Pachastrissamine ( jaspine B) and diastereoisomeric jaspines
Synthesis and biological properties of Pachastrissamine ( jaspine B) and diastereoisomeric jaspines
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DOI：
10.1016/j.bmc.2008.11.026
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发表时间：
2009-01-01
影响因子：
3.5
通讯作者：
Delgado, Antonio
中科院分区：
文献类型：
--
作者：
Canals, Daniel;Mormeneo, David;Delgado, Antonio
本文报道了在类鞘氨醇主链C_3和C_4位上具有不同构型的植物鞘氨醇分子内环化反应，合成了同分异构的碧玉碱（脱水植物鞘氨醇）。天然茉莉花碱B是对A549细胞最具细胞毒性的异构体，它以剂量依赖性方式诱导细胞死亡。jaspine B的细胞毒性与细胞内二氢神经酰胺的显著增加相关，其似乎在自噬中起积极作用。(c)2008爱思唯尔有限公司保留所有权利。
The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different con. gurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role in autophagy. (c) 2008 Elsevier Ltd. All rights reserved.