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来自青灰叶下珠的新细胞毒性木脂素糖苷。

New cytotoxic lignan glycosides from Phyllanthus glaucus.

作者信息

Yu Shan, Lv Jun-Jiang, Zhao Jian-Qiang, Li Yan, Wang Dong, Yang Chong-Ren, Xu Min, Zhang Ying-Jun

机构信息

a State Key Laboratory of Phytochemistry & Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Lanhei Road 132#, Kunming 650201 , People's Republic of China.

b University of Chinese Academy of Sciences , Beijing 100049 , People's Republic of China.

出版信息

Nat Prod Res. 2016;30(4):419-25. doi: 10.1080/14786419.2015.1023198. Epub 2015 Mar 20.

DOI:10.1080/14786419.2015.1023198
PMID:25791206
Abstract

During the process of exploring bioactive lead compounds from Phyllanthus species, two new glycosides including an arylnaphthalene lignan, diphyllin 4-O-α-L-arabinopyranosyl-(1 → 3)-α-L-arabinopyranoside (1), and a phenolic compound, 3,4,5-trimethoxybenzyl alcohol 7-O-α-L-arabinofuranosyl-(1 → 6)-β-D-glucopyranoside (2), were isolated from the methanol extract of the whole plants of Phyllanthus glaucus Wall. ex Müll. Arg. In addition, 31 known compounds, including 19 lignan derivatives (3-21), four phenylpropanoids (22-25), seven simple phenolics (26-32) and one monoterpenoid (33) were obtained. Their structures were determined on the basis of the HR-ESI-MS, 1D and 2D NMR spectroscopic analysis, and pre-column derivative/chiral HPLC analysis in case of 1 for the absolute configurations. All these compounds were obtained from P. glaucus for the first time. Moreover, the known lignan glycoside, phyllanthusmin C (5) showed in vitro cytotoxicities against HL-60, MCF-7 and SW480 cells with IC50 values of 9.2 ± 0.2, 19.2 ± 1.7 and 20.5 ± 0.9, respectively.

摘要

在从叶下珠属植物中探索生物活性先导化合物的过程中,从青灰叶下珠(Phyllanthus glaucus Wall. ex Müll. Arg.)全株的甲醇提取物中分离出两种新的糖苷,包括一种芳基萘木脂素,双叶素4-O-α-L-阿拉伯吡喃糖基-(1→3)-α-L-阿拉伯吡喃糖苷(1)和一种酚类化合物,3,4,5-三甲氧基苄醇7-O-α-L-阿拉伯呋喃糖基-(1→6)-β-D-葡萄糖吡喃糖苷(2)。此外,还获得了31种已知化合物,包括19种木脂素衍生物(3-21)、4种苯丙素类化合物(22-25)、7种简单酚类化合物(26-32)和1种单萜类化合物(33)。通过高分辨电喷雾电离质谱(HR-ESI-MS)、一维和二维核磁共振光谱分析以及对于化合物1绝对构型的柱前衍生化/手性高效液相色谱分析确定了它们的结构。所有这些化合物均首次从青灰叶下珠中获得。此外,已知的木脂素糖苷叶下珠素C(5)对HL-60、MCF-7和SW480细胞显示出体外细胞毒性,IC50值分别为9.2±0.2、19.2±1.7和20.5±0.9。

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