Gentisides C-K: Nine new neuritogenic compounds from the traditional Chinese medicine Gentiana rigescens Franch
Gentisides C-K: Nine new neuritogenic compounds from the traditional Chinese medicine Gentiana rigescens Franch
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龙胆苷 C-K：中药龙胆中的九种新的致神经炎化合物
DOI：
10.1016/j.bmc.2010.08.020
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发表时间：
2010-10-01
影响因子：
3.5
通讯作者：
Qi, Jianhua
中科院分区：
文献类型：
--
作者：
Gao, Lijuan;Xiang, Lan;Qi, Jianhua
从中药滇龙胆（Gentiana rigescens Franch）中分离得到9个新的2，3-二羟基苯甲酸烷基酯化合物，命名为龙胆苷C-K。通过波谱方法和与龙胆苷B的比旋光度比较，确定了它们的结构和立体化学。这些代谢产物是龙胆苷的额外成员，龙胆苷属于一类新的神经元生成化合物。它们在结构上彼此不同，因为它们具有不同的烷基链长度，在烷基链的末端具有或不具有异丁基或异丙基。这些化合物是PC 12细胞上神经突生长的有效诱导剂。龙胆苷C具有最短的烷基链长度表现出最高的神经轴突活性在所有的龙胆苷。龙胆苷C在1 μ M时对PC 12细胞显示出显著的神经突生成活性，与40 ng/mL的最佳神经生长因子（NGF）浓度所见的活性相当。此外，当用浓度低至0.03 μ M的龙胆苷C处理时，在细胞中观察到明显的神经突发生活性。龙胆皂苷A-K的构效关系表明，烷基链的长度对活性很重要，但烷基链末端的结构多样性对活性不重要。(C)2010爱思唯尔有限公司保留所有权利。
Nine new alkyl 2,3-dihydroxybenzoates, gentisides C-K, were isolated from the traditional Chinese medicine Gentiana rigescens Franch. Their structures and stereochemistry were elucidated by spectroscopic methods, and comparison of the specific rotation with that of the gentiside B. These metabolites are additional members of the gentisides which belong to a novel class of neuritogenic compounds. They are structurally different from one another because they possess varying alkyl chain lengths, with or without an isobutyl or isopropyl group at the end of the alkyl chain. These compounds are potent inducers of neurite outgrowth on PC12 cells. The gentiside C possessing the shortest alkyl chain length exhibited the highest neuritogenic activity among all of the gentisides. Gentiside C showed a significant neuritogenic activity at 1 mu M against PC12 cells comparable to that seen for the best nerve growth factor ( NGF) concentration of 40 ng/mL. In addition, evident neuritogenic activity was observed in the cells when treated with gentiside C at a concentration as low as 0.03 mu M. The structure-activity relationships within the gentisides A-K revealed that alkyl chain length is important for the activity, but structure diversity at the end of the alkyl chain is not. (C) 2010 Elsevier Ltd. All rights reserved.