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高效液相色谱-四极杆/轨道阱质谱法在白花蛇舌草乙酸乙酯部位抗癌成分检测与鉴定中的应用

Application of HPLC-Q/orbitrap MS in the detection and identification of anticancer constituents in ethyl acetate components from Hedyotis diffusa.

作者信息

Chen Xi, Zhao Baojin, Zhang Mengjiao, Dong Min, Li Yunlan, Li Qingshan

机构信息

School of Pharmaceutical Science, Shanxi Medical University, Taiyuan 030001, P. R. China.

出版信息

Anal Methods. 2020 Aug 28;12(32):4037-4047. doi: 10.1039/d0ay00531b. Epub 2020 Aug 4.

Abstract

A feasible analytical method based on high performance liquid chromatography-quadrupole/electrostatic field orbitrap high-resolution mass spectrometry (HPLC-Q/orbitrap MS) has been established for the identification and characterization of anticancer constituents in ethyl acetate components from Hedyotis diffusa in our work. The mass spectrometer provided significant fragment information both in the full MS scan and data-dependent MS modes. Sixty-two possible compounds were analyzed and identified from the above results. Of the above 62 compounds, 12 have good separation in the positive ion mode, and 27 compounds have good separation in the anion mode. Currently, 39 have been reported in the literature related to the chemical composition of the plant, while the other 23 of the 62 compounds have not been reported. Fifteen tentatively identified compounds were given detailed descriptions. Four representative compounds from the ethyl acetate extract among the fifteen were actually isolated in good yield with silica gel column chromatography. Meanwhile, their structures were unambiguously identified as scopoletin, vanillic acid, p-coumaric acid and E-6-O-p-coumaroyl scandoside methyl ester using H NMR, C NMR, IR and UV spectroscopy. The purity of the ethyl acetate extracts, the total flavonoids, from Hedyotis diffusa could reach 65.6%. The inhibitory effect on HepG-2 cells of the total flavonoids was up to 66.2 ± 2.7%. Amentoflavone, quercetin, naringenin, and rutin were selected from the total flavonoids. The amentoflavone and quercetin had better hepatoprotective activity. The inhibition rates of 500 μmol L amentoflavone and quercetin on HepG-2 cells could reach 56.2 ± 8.1% and 78.0 ± 9.3%, respectively. The EtOAc extracts could induce apoptosis in HepG2 cells by blocking the cell cycle in the G0/G1 phase. To the best of our knowledge, this is the first time that Q-orbitrap HRMS was applied to detect potential anticancer compounds in Hedyotis diffusa. This analytical method proved to be a feasible approach for the rapid detection of the potential anticancer compounds from Hedyotis diffusa.

摘要

在我们的工作中,已建立了一种基于高效液相色谱 - 四极杆/静电场轨道阱高分辨率质谱(HPLC - Q/轨道阱MS)的可行分析方法,用于鉴定和表征白花蛇舌草乙酸乙酯部位中的抗癌成分。该质谱仪在全扫描质谱和数据依赖型质谱模式下均提供了重要的碎片信息。根据上述结果分析并鉴定出62种可能的化合物。在上述62种化合物中,12种在正离子模式下具有良好的分离效果,27种在负离子模式下具有良好的分离效果。目前,在与该植物化学成分相关的文献中已报道了39种,而这62种化合物中的其他23种尚未见报道。对15种初步鉴定的化合物进行了详细描述。通过硅胶柱色谱法从这15种化合物中实际分离得到了乙酸乙酯提取物中的4种代表性化合物,且产率良好。同时,利用¹H NMR、¹³C NMR、IR和UV光谱明确鉴定了它们的结构,分别为东莨菪内酯、香草酸、对香豆酸和E - 6 - O - 对香豆酰东莨菪苷甲酯。白花蛇舌草乙酸乙酯提取物中总黄酮的纯度可达65.6%。总黄酮对HepG - 2细胞的抑制作用高达66.2±2.7%。从总黄酮中选取了穗花杉双黄酮、槲皮素、柚皮素和芦丁。穗花杉双黄酮和槲皮素具有较好的保肝活性。500 μmol/L穗花杉双黄酮和槲皮素对HepG - 2细胞的抑制率分别可达56.2±8.1%和78.0±9.3%。乙酸乙酯提取物可通过阻断HepG2细胞周期于G0/G1期诱导其凋亡。据我们所知,这是首次将Q - 轨道阱高分辨质谱应用于检测白花蛇舌草中的潜在抗癌化合物。该分析方法被证明是一种快速检测白花蛇舌草中潜在抗癌化合物的可行方法。

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