Anti-viral and cytotoxic norbisabolane sesquiterpenoid glycosides from Phyllanthus emblica and their absolute configurations
Anti-viral and cytotoxic norbisabolane sesquiterpenoid glycosides from Phyllanthus emblica and their absolute configurations
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余甘子中的抗病毒和细胞毒性降红没药烷倍半萜糖苷及其绝对构型。
DOI：
10.1016/j.phytochem.2015.06.001
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发表时间：
2015-09-01
期刊：
影响因子：
3.8
通讯作者：
Zhang, Ying-Jun
中科院分区：
文献类型：
--
作者：
Lv, Jun-Jiang;Yu, Shan;Zhang, Ying-Jun
为鉴定余甘子属（Phyllanthus emblica Linn）的抗病毒和细胞毒性化合物，从余甘子根（phyllaemblicins h1 ~ h14）和余甘子苷（phyllaemblicins B、C、glochicococcinoside d）中分离得到了14个高氧合降双abolane倍半萜类化合物，通过详细的光谱分析和化学方法对其结构进行了鉴定。利用时间依赖密度泛函理论（TDDFT）计算电子圆二色（ECD）光谱，并对单糖进行柱前衍生物/手性高效液相色谱（HPLC）分析，确定了化合物的绝对构型。已知的环椒苷D对甲型流感病毒H3N2株和手足口病毒EV71株具有较强的抑制活性，IC50值分别为4.5 +/- 0.6和2.6 +/- 0.7 μ g/ml。Phyllaemblicin H1对人癌细胞A-549和SMMC-7721表现出中等的细胞毒性，IC50值分别为4.7 +/- 0.7和9.9 +/- 1.3 μ M。(C) 2015 Elsevier Ltd.版权所有。
In an effort to identify anti-viral and cytotoxic compounds from Phyllanthus spp., 14 highly oxygenated norbisabolane sesquiterpenoids, phyllaemblicins H1-H14, were isolated from the roots of Phyllanthus emblica Linn, along with phyllaemblicins B and C and glochicoccinoside D. Their structures were determined on the basis of detailed spectroscopic analysis and chemical methods. Determination of absolute configurations of these compounds was facilitated by theoretical calculations of electronic circular dichroism (ECD) spectra using time-dependent density functional theory (TDDFT) for the aglycone components, and pre-column derivative/chiral HPLC analysis for the monosaccharides. The known glochicoccinoside D displayed potent activity against influenza A virus strain H3N2 and hand, foot and mouth virus EV71, with IC50 values of 4.5 +/- 0.6 and 2.6 +/- 0.7 mu g/ml, respectively. Phyllaemblicin H1 showed moderate cytotoxicity against human cancer cell lines A-549 and SMMC-7721, with IC50 values of 4.7 +/- 0.7 and 9.9 +/- 1.3 mu M, respectively. (C) 2015 Elsevier Ltd. All rights reserved.