Separation of the potential G-quadruplex ligands from the butanol extract of Zanthoxylum ailanthoides Sieb. & Zucc. by countercurrent chromatography and preparative high performance liquid chromatography

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	Separation of the potential G-quadruplex ligands from the butanol extract of Zanthoxylum ailanthoides Sieb. & Zucc. by countercurrent chromatography and preparative high performance liquid chromatography
	Han, Tian 1; Cao, Xueli 1; Xu, Jing 1; Pei, Hairun 1; Zhang, Hong 2; Tang, Yalin 2
刊名	JOURNAL OF CHROMATOGRAPHY A
	2017-07-21
卷号	1507 页码:104-114
关键词	Zanthoxylum Ailanthoides Sieb. & Zucc Anti-tumor Activity G-quadruplex Ligands Alkaloids Ph-zone Refining Counter Current Chromatography (Ccc)
英文摘要	G-quadruplex DNA structure is considered to be a very attractive target for antitumor drug design due to its unique role in maintaining telomerase activities. Therefore, discovering ligands with high stability of G-quadruplex structure is of great interest. In this paper, pH-zone refining counter current chromatography (CCC) and preparative high performance liquid chromatography (HPLC) were employed for the separation of potent G-quadruplex ligands from the n-butanol fraction of the crude extract of Zanthoxylum ailanthoides, which is a traditional Chinese medicine recently found to display high inhibitory activity against several human cancer cells. The 75% aqueous ethanol extract of the stem bark of Z. ailanthoides and its fractions with petroleum ether, ethyl acetate and n-butanol displayed almost the same G-quadruplex stabilization ability. Here, pH-zone refining CCC was used for the separation of the alkaloids from the n-butanol fraction by a seldom used solvent system composed of dichloromethane-methanol-water (4:1:2.5) with 10 mM TEA in the organic stationary phase as retainer and 10 mM HCl in the aqueous mobile phase as eluter. Compounds I, II and III were obtained, with purity greater than 95%, in the quantities of 31.2, 94.0, and 26.4 mg respectively from 300 mg of lipophilic fraction within 80 min, which were identified as three tetrahydroprotoberberines isolated for the first time in this plant. In addition, a phenylpropanoid glycoside compound IV (Syringin), an isoquinoline (Magnoflorine, V), and two lignin isomers (+)-Iyoniresiol-3 alpha-O-beta-D-glucopyranoside (VI) and (-)-lyoniresinol 3 alpha-O-beta-D glucopyranoside (VII) were isolated by traditional CCC together with preparative HPLC. Compounds IV, V, VI and VII were obtained, with purity greater than 95%, in the quantities of 4.0, 13.2, 6.7, and 6.5 mg respectively from 960 mg of hydrophilic fraction. Among the seven isolated compounds, tetrahydroprotoberberine I, II and III were found to display remarkable stabilization effects on G-quadruplex by increasing G-quadruplex's T-m approximately 10 degrees C, which may be the most potent G-quadruplex ligands in Z. ailanthoides. (C) 2017 Elsevier B.V. All rights reserved.
语种	英语
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/38939]
专题	化学研究所_分子动态与稳态结构实验室
作者单位	1.BTBU, Beijing Adv Innovat Ctr Food Nutr & Human Hlth, Beijing 100048, Peoples R China 2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Han, Tian,Cao, Xueli,Xu, Jing,et al. Separation of the potential G-quadruplex ligands from the butanol extract of Zanthoxylum ailanthoides Sieb. & Zucc. by countercurrent chromatography and preparative high performance liquid chromatography[J]. JOURNAL OF CHROMATOGRAPHY A,2017,1507:104-114.
APA	Han, Tian,Cao, Xueli,Xu, Jing,Pei, Hairun,Zhang, Hong,&Tang, Yalin.(2017).Separation of the potential G-quadruplex ligands from the butanol extract of Zanthoxylum ailanthoides Sieb. & Zucc. by countercurrent chromatography and preparative high performance liquid chromatography.JOURNAL OF CHROMATOGRAPHY A,1507,104-114.
MLA	Han, Tian,et al."Separation of the potential G-quadruplex ligands from the butanol extract of Zanthoxylum ailanthoides Sieb. & Zucc. by countercurrent chromatography and preparative high performance liquid chromatography".JOURNAL OF CHROMATOGRAPHY A 1507(2017):104-114.