高效液相色谱和Q-Exactive四极杆-静电场轨道阱高分辨质谱仪联用鉴定半枝莲的化学成分

doi:10.5246/jcps.2015.10.081

中国药学(英文版) ›› 2015, Vol. 24 ›› Issue (10): 635-646.DOI: 10.5246/jcps.2015.10.081

• 【研究论文】 • 下一篇

高效液相色谱和Q-Exactive四极杆-静电场轨道阱高分辨质谱仪联用鉴定半枝莲的化学成分

李茹¹, 宋玮¹, 乔雪¹, 刘佳², 梁鸿¹, 叶敏^1*

1. 北京大学药学院天然药物及仿生药物国家重点实验室, 北京 100191
2. 北京大学基础医学院系统生物学研究所, 北京 100191

收稿日期:2015-05-13 修回日期:2015-06-28 出版日期:2015-10-21 发布日期:2015-07-05
通讯作者: Tel.: 86-10-82802024, E-mail: yemin@bjmu.edu.cn
基金资助:
National Natural Science Foundation of China (Grant No. 81222054 and 21305005), the Program for New Century Excellent Talents in University from Chinese Ministry of Education (Grant No. NCET-11-0019), and National Science and Technology Mega Project for Primary Drug Innovation of China (Grant No. 2014ZX09304-307).

Chemical profiling of Scutellaria barbata by ultra high performance liquid chromatography coupled with hybrid quadrupole-orbitrap mass spectrometry

Ru Li¹, Wei Song¹, Xue Qiao¹, Jia Liu², Hong Liang¹, Min Ye^1*

1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China
2. Institute of Systems Biomedicine, Beijing Key Laboratory of Tumor Systems Biology, School of Basic Medical Sciences, Peking University Health Science Center, Peking University, Beijing 100191, China

Received:2015-05-13 Revised:2015-06-28 Online:2015-10-21 Published:2015-07-05
Contact: Tel.: 86-10-82802024, E-mail: yemin@bjmu.edu.cn
Supported by:
National Natural Science Foundation of China (Grant No. 81222054 and 21305005), the Program for New Century Excellent Talents in University from Chinese Ministry of Education (Grant No. NCET-11-0019), and National Science and Technology Mega Project for Primary Drug Innovation of China (Grant No. 2014ZX09304-307).

摘要/Abstract

摘要：

利用高效液相色谱和Q-Exactive四极杆-静电场轨道阱高分辨质谱仪联用的方法对中药半枝莲的化学成分进行分析, 药材粉末经70%甲醇提取后采用Agilent Eclipse Plus C₁₈ column (1.8 μm, 150 mm×2.1 mm)色谱柱分离, 流动相为甲醇–乙腈–0.1%甲酸水溶液, 采用梯度洗脱, 流速为0.25 mL/min。质谱采用负离子监测模式、采用全扫描及自动触发二级质谱扫描的功能, 通过高分辨数据共鉴定了56个成分, 包括黄酮苷元类20个, 黄酮氧苷类20个, 黄酮碳苷类2个, 苯乙醇苷类成分4个, 以及10个小分子的苯酚类成分, 其中8个黄酮类成分和2个苯乙醇苷类成分经对照品比对确证。本研究表明, Q-Exactive四级杆-静电场轨道阱高分辨质谱可以高效地鉴定复杂植物提取物的未知化学成分。

关键词: 半枝莲, 化学成分分析, Q-Exactive四极杆-静电场轨道阱高分辨质谱, 黄酮

Abstract:

An ultrahigh performanceliquid chromatographycoupled with hybrid quadrupole-orbitrap mass spectrometry (UHPLC-quadrupole-orbitrap MS) method was developed to systematically analyze chemical constituents of Scutellaria barbata D. Don. The 70% methanol extract was separated on an Agilent Eclipse Plus C₁₈ column (1.8 μm, 150 mm×2.1 mm), and eluted with a gradient of methanol–acetonitrile–water containing 0.1% formic acid at a flow rate of 0.25 mL/min. Constituents were identified by HRMS in the negative ion mode using both full scan and two-stage threshold-triggered mass modes. A total of 56 compounds, including 20 free flavonoids, 20 flavonoid O-glycosides, 2 flavonoid C-glycosides, 4 phenylethanoid glycosides, and 10 phenolic compoundswere identified by analyzing their high resolution mass spectral data.Among them, 8 flavonoids and 2 phenylethanoid glycosides were unambiguously identified by comparing with reference standards. This study demonstrates that hybrid quadrupole-orbitrap mass spectrometry is a powerful tool in structural identification of unknown compounds in complicated herbal extracts.

Key words: Scutellaria barbata, Chemical analysis, Quadrupole-orbitrap mass spectrometry, Flavonoids

中图分类号:

R284

Supporting:

李茹, 宋玮, 乔雪, 刘佳, 梁鸿, 叶敏. 高效液相色谱和Q-Exactive四极杆-静电场轨道阱高分辨质谱仪联用鉴定半枝莲的化学成分[J]. 中国药学(英文版), 2015, 24(10): 635-646.

Ru Li, Wei Song, Xue Qiao, Jia Liu, Hong Liang, Min Ye . Chemical profiling of Scutellaria barbata by ultra high performance liquid chromatography coupled with hybrid quadrupole-orbitrap mass spectrometry [J]. Journal of Chinese Pharmaceutical Sciences, 2015, 24(10): 635-646.

参考文献

[1] Shang, X.F.; He, X.R.; He, X.Y.; Li, M.X.; Zhang, R.X.; Fan, P.C.; Zhang, Q.L.; Jia, Z.P. J. Ethnopharmacol. 2010, 128, 279-313.

[2] Chinese Pharmacopoeia Commission. Pharmacopoeia of the People’s Republic of China. Version 2010. Vol.1. Beijing: China medicine science and technology press, 2010, 109-110.

[3] Sato, Y.; Suzaki, S.; Nishikawa, T.; Kihara, M.; Shibata, H.; Higuti, T. J. Ethnopharmacol. 2000, 72, 483-488.

[4] Chen, V.; Staub, R.E.; Baggett, S.; Chimmani, R.; Tagliaferri, M.; Cohen, I.; Shtivelman, E. PLoS One. , 7, e30107.2012

[5] Ha, N.; Xuan, B.; Tang, P.M.K.; Wong, C.K.; Fung, K.P. J. Ethnopharmacol. 2010, 131, 95-103.

[6] Qiao, S.; Shi, R.; Liu, M.; Zhang, C.; Yang, W.; Shi, X.; Jiang, X.; Wang, C.; Wang, Q. Food Chem. 2011, 129, 1297-1304.

[7] Wei, M.C.; Yang, Y.C.; Chiu, H.F.; Hong, S.J. J. Chromatogr. B. 2013, 940, 126-134.

[8] Hu, X.L.; You, J.Y.; Bao, C.L.; Zhang, H.R.; Meng, X.Z.; Xiao, T.T.; Zhang, K.; Wang, Y.T.; Wang, H.M.; Zhang, H.Q.; Yu, A.M. Anal. Chim. Acta. 2008, 610, 217-223.

[9] Nijveldt, R.J.; Nood, E.V.; Hoorn, D.E.V.; Boelens, P.G.; Norren, K.V.; Leeuwen, P.A.V. Am. J. Clin. Nutr. 2001, 74, 418-425.

[10] Ji, S.G.; Liu, Y.; Mao, F.; Li, X.; Chai, Y.F. J. Pharm. Pract. 2012, 6, 437-440.

[11] Zhang, Z.F.; He, L.L.; Lu, L.Y.; Liu, Y.; Dong, G.T.; Miao, J.H.; Luo, P. J. Pharm. Biomed. Anal. 2015, 109, 62-66.

[12] Wang, Y.P.; Xue, X.Z.; Zhang, X.L.; Jin, Y.; Zhang, F.F.; Liang, X.M. J. Chin. Mass Spectrom. Soc. 2009, 30, 129-138.

[13] Hu, Q.Z.; Noll, R.J.; Li, H.Y.; Makarov, A.; Hadman, M.; Cooks, R.G. J. Mass Spectrom. 2005, 40, 430-443.

[14] Heeft, E.; Bolck, Y.J.C; Beumer, B.; Nijrolder, A.W.J.M.; Stolker, A.A.M.; Nielen, M.W.F. J. Am. Soc. Mass Spectrom. 2009, 20, 451-463.

[15] Yang, Y.; Wang, H.J.; Yang, J.; Brantner, A.H. J. Chromatogr. A. 2013, 1321, 88-99.

[16] Cao, G.; Li, Q.; Cai, H.; Tu, S.; Cai, B. Evid-Based Complement. Alternat. Med. 2014, Article ID 170959.

[17] Cuyckens, F.; Claeys, M. J. Mass Spectrom. , 39, 1-15. 2004

[18] Fabre, N.; Rustan, I.; Hoffmann, E.; Quetin-Leclercq, J. J. Am. Soc. Mass Spectrom. 2001, 12, 707-715.

[19] Yang, W.Z.; Ye, M.; Qiao, X.; Wang, Q.; Bo, T.; Guo, D.A. Eur. J. Mass Spectrom. 2012, 18, 493-503.

[20] Tomimori, T.; Miyaichi, Y.; Imoto, Y.; Kizu, H.; Namba, T. Chem. Pharm. Bull. 1986, 34, 406-408.

[21] Zhang, Y.Y.; Guo, Y.Z.; Onda, M.; Hashimoto, K.; Ikeya, Y.; Okada, M.; Maruno, M. Phytochemistry. 1994, 35, 511-514.

[22] Ponce, M.A.; Scervino, J.M.; Erra-Balsells, R.; Ocampo, J.A.; Godeas, A.M. Phytochemistry. 2004, 65, 1925-1930.

[23] Matsuura, Y.; Miyaichi, Y.; Tomimori, T. Yakugaku Zasshi. 1994, 114, 775-788.

[24] Marques, M.R.; Stüker, C.; Kichik, N.; Tarragó. T.; Giralt, E.; Morel, A.F.; Dalcol, I.I. Fitoterapia. 2010, 81, 552-556.

[25] Zhou, Y.; Hirotani, M.; Yoshikawa, T.; Furuya, T. Phytochemistry. 1997, 44, 83-87.

[26] Singh, U.V.; Udupa, Ratcliff, J.T.; Tackley, P.J.; Schubert, G.; Zebib, A.; Esquivel, B.; Calderon, J.S.; Sanchez, A.; Zarate, M.; Sanchez, L. Phytochemistry. 1997, 3, 781-783.

[27] Vukics, V.; Guttman, A. Mass Spectrom. Rev. 2010, 29, 1-16.

[28] Liu, G.Z.; Rajesh, N.; Wang, X.S.; Zhang, M.S.; Wu, Q.; Li, S.J. Chen, B.; Yao, S.Z. J. Chromatogr. B. 2011, 879, 1023-1028.

[29] Zhou, Z.H.; Yang, C.R. Acta Bot. Yunnanica. 2000, 22, 475-481.

[30] Cuong, T.D.; Hung, T.M.; Lee, J.S.; Weon, K.Y.; Woo, M.H.; Min, B.S. Bioorg. Med. Chem. Lett. 2015, 25, 1129-1134.

[31] Miyaichi, Y.; Imoto, Y.; Tomimori, T.; Namba, T. Chem. Pharm. Bull. 1988, 36, 2371-2376.

[32] Qi, W.Y.; Matsuzaki, K.; Takahashi, K.; Okuyama, T.; Shibata, S. Chem. Pharm. Bull. 1988, 36, 3206-3209.

[33] Wu, W.; Yuan, C.; Li, L.; Liu, Z.Q.; Liu, S.Y. J. Chromatogr. A. 2004, 1047, 213-220.

[34] Li, P. Master Thesis, Shenyang Pharmaceutical University. 2008.

[35] Ostrowski, W.; Wojakowska, A.; Grajzer, M.; Stobiecki, M. J. Chromatogr. B. 2014, 967, 21-27.

高效液相色谱和Q-Exactive四极杆-静电场轨道阱高分辨质谱仪联用鉴定半枝莲的化学成分

Chemical profiling of Scutellaria barbata by ultra high performance liquid chromatography coupled with hybrid quadrupole-orbitrap mass spectrometry

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	乔自鹏, 王奇志, 刘建福, 王明元. 胜红蓟内生真菌乙酸乙酯提取物的抗氧化及抑菌活性研究[J]. 中国药学(英文版), 2021, 30(5): 421-433.
[2]	陈佳倩, 金晨, 徐博伦, 詹煌, 付容容, 李风琴, 黄慧莲. 菝葜总黄酮主成分鉴定及苯酚胶浆诱导大鼠盆腔炎的抗炎作用评价[J]. 中国药学(英文版), 2021, 30(2): 157-168.
[3]	徐方方, 孙彪, 张晓琦, 刘博. 北枳椇子中的黄酮碳苷类成分[J]. 中国药学(英文版), 2020, 29(11): 813-818.
[4]	花一鸣, 张晓雯, 曾克武, 张庆英, 屠鹏飞. 蛇婆子地上部分化学成分研究[J]. 中国药学(英文版), 2019, 28(7): 468-475.
[5]	程士轩, 马迎聪, 刘瑜洁, 庞宁, 李骥, 沙勐, 任汝通, Nuramatjan Ablat, 曹静, 孙懿, 蒲小平, 叶敏, 齐宪荣. 红花抗帕金森病有效成分滴丸的制备和表征[J]. 中国药学(英文版), 2019, 28(1): 27-39.
[6]	张圃铭, 章宸, 曾克武, 姜勇, 屠鹏飞. 山蒿中木脂素和黄酮类化学成分研究[J]. 中国药学(英文版), 2018, 27(6): 429-435.
[7]	赵一帆, 张东, 梁彩霞, 杨立新, 孙鹏, 马悦, 王坤, 常小强, 杨岚. 维药洋甘菊化学成分研究I[J]. 中国药学(英文版), 2018, 27(5): 324-331.
[8]	蔡雁, 戴巍, 钦富华, 孙洁胤, 魏瑞龙. 染料木黄酮泊洛沙姆P407/P403混合胶束的制备及药动学研究[J]. 中国药学(英文版), 2018, 27(5): 342-351.
[9]	张兰军, 毕德文, 王吉华, 夏光惠, 王利勤. 九羽见血飞枝叶的化学成分[J]. 中国药学(英文版), 2018, 27(12): 864-870.
[10]	房芯羽, 王蓉蓉, 孙世伟, 刘晓晓, 刘小红, 王炜, 岡田嘉仁, 王威. Cistus parviflorus叶化学成分研究[J]. 中国药学(英文版), 2018, 27(1): 40-50.
[11]	王俊杰, 王超, 吕鹏, 牛彦, 李宏月, 黄文慧, 李灿, 许凤荣, 梁磊, 徐萍. 异黄酮类CLR/RAMP1拮抗剂的设计、合成及生物活性评价[J]. 中国药学(英文版), 2017, 26(7): 504-511.
[12]	江海秀, 管颜青, 张笑天, 韩雅, 郭宁宁, 王弘, 陈世忠. 双黄连注射剂中四种黄酮类半抗原成分与牛血清白蛋白作用机制研究[J]. 中国药学(英文版), 2017, 26(5): 366-371.
[13]	梁公文, 李娜, 马丽萍, 赵立波, 史录文. 高效液相色谱-串联质谱法检测小鼠血浆和脑组织中沙奎那韦[J]. 中国药学(英文版), 2017, 26(2): 106-114.
[14]	赵一懿, 郭洪祝, 陈有根, 傅欣彤. 基于UPLC-QTOF-MSE代谢组学方法对银杏叶提取物中黄酮醇苷、萜类内酯、酚类及羧酸类成分含量差异研究[J]. 中国药学(英文版), 2017, 26(11): 789-804.
[15]	舒任庚, 严喜鸾, 李莎莎, 屠鹏飞. 高效液相色谱法同时测定山蜡梅叶中的l-洋蜡梅碱、槲皮素和山奈酚的含量[J]. 中国药学(英文版), 2017, 26(11): 805-810.