Bioactive carbazole and quinoline alkaloids from Clausena dunniana
Bioactive carbazole and quinoline alkaloids from Clausena dunniana
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DOI：
10.1016/j.phytochem.2018.03.009
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发表时间：
2018-07-01
期刊：
影响因子：
3.8
通讯作者：
Jiang, Yong
中科院分区：
文献类型：
--
作者：
Cao, Nankai;Chen, Yuemei;Jiang, Yong
从黄皮(Clausena Dunniana)叶和茎中分离得到9个未见文献报道的咔唑和喹啉生物碱，命名为Dunnines A-E和14个已知类似物。在综合分析核磁共振和高分辨质谱学数据的基础上，确定了它们的结构，并通过比较它们的比旋光度和ECD计算数据和实验数据，确定了它们的绝对构型。(+/-)-丹宁A-C和(+/-)-黄皮糖A是四对双咔唑对映体，(+/-)-丹宁D是一对二氢吡喃并咔唑对映体。通过手性高效液相色谱分离得到光学纯度较高的化合物。3个化合物对脂多糖刺激的BV-2小胶质细胞(IC50>；50 mU M)产生一氧化氮有微弱的抑制作用；5个化合物在40 mU M时能显著促进HIT-T15细胞(是对照的1.9-3.1倍，p<；0.01)胰岛素的分泌；9个化合物能抑制6-羟基多巴胺诱导的PC12细胞的凋亡，IC50在10.9-47.2 mU M(C)2018爱思唯尔有限公司。版权所有。
Nine undescribed carbazole and quinoline alkaloids, named dunnines A-E, and 14 known analogues were isolated from the leaves and stems of Clausena dunniana. Their structures were elucidated on the basis of comprehensive analysis of NMR and HRMS spectroscopic data, and the absolute configurations were assigned via comparison of their specific rotations and calculated and experimental ECD data. (+/-)-Dunnines A-C and (+/-)-clausenawalline A are four pairs of biscarbazole atropisomers and (+/-)-dunnine D is a pair of dihydropyranocarbazole enantiomers. They were separated by chiral HPLC to obtain the optically pure compounds. Three compounds showed weak inhibitory effects on nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells (IC50 > 50 mu M); five compounds could significantly promote insulin secretion in HIT-T15 cell line (1.9-3.1-fold of the control, p < 0.01) at 40 mu M, and nine compounds could inhibit the apoptosis of PC12 cell induced by 6-hydroxydopamine with IC50 values in the range of 10.9-47.2 mu M. (C) 2018 Elsevier Ltd. All rights reserved.