基于UPLC-Triple TOF MS/MS技术分析苍耳子炒制前后的差异化学成分
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摘要
为探讨苍耳子炒制前后化学成分的变化,采用超高效液相色谱-串联四极杆飞行时间高分辨质谱(UPLC-Triple TOF MS/MS)法,结合多元统计分析技术,对苍耳子炒制前后化学成分的差异性进行分析。通过分析二级串联质谱,针对峰匹配、峰对齐、滤噪处理等进行特征峰提取;采用主成分分析(PCA)和偏最小二乘-判别分析(PLS-DA)法进行数据处理;根据一级质谱精确质荷比和二级质谱碎片信息,结合软件数据库搜索、标准品比对及相关文献数据进行成分鉴定。结果表明,苍耳子炒制前后的化学组成得到了有效区分,初步筛选出44个差异化学成分,并鉴定出其中的41个成分;所分析的样品共有10个差异化学成分,在不同样品中呈现不同的变化规律。该方法可为解析苍耳子药材的品质形成机制提供基础资料,也可为解释苍耳子炒制减毒的科学内涵提供依据。
The method of UPLC-Triple TOF MS/MS combined with multivariate statistical analysis was used to study the differences of chemical compositions in Xanthii Fructus before and after stir-frying.Through the analysis of the multistage tandem mass spectrometry,the characteristic peaks were extracted with mass spectrometry data peak matching,peak alignment,noise filtering.Principal component analysis(PCA)and partial least-squares discriminant analysis(PLS-DA)were used for data processing.Thechemical compositions were identified and tentative presumed according to MS accurate mass and MS/MS spectrometry fragmentation information,combined with the software of database search and comparison with reference standards and literature.The results show that the chemical compositions in Xanthii Fructus before and after stir-frying are clearly distinguished.A total of 44 different chemical compositions are detected in Xanthii Fructus before and after stir-frying,and 41 chemical compositions of which are identified.Among of them,there are 10 kinds of common differential compositions,such as liquiritigenin 4′-O-apiosyl-O-glucoside,3′,4′,5,7-tetramethoxyflavone,chlorogenic acid,deoxyadenosine,4-dicaffeoylquinic acid,1,3-dicaffeoylquinic acid,3,4-dicaffeoylquinic acid,astragalin,4′-desulphate-atractylosid andβ-carotene, which present different change laws.In the 10 differential components,the contents of liquiritigenin 4′-O-apiosyl-O-glucoside,deoxyadenosine,1,3-dicaffeoylquinic acid,3,4-dicaffeoylquinic acid,astragalin,andβ-carotene are much higher in Xanthii Fructus after stir-frying,while the contents of 3′,4′,5,7-tetramethoxyflavone,chlorogenic acid,4-dicaffeoylquinic acid,and 4′-desulphate-atractylosid are lower.This study provides a basic information for revealing the change law of chemical compositions in Xanthii Fructus before and after stir-frying.
The method of UPLC-Triple TOF MS/MS combined with multivariate statistical analysis was used to study the differences of chemical compositions in Xanthii Fructus before and after stir-frying.Through the analysis of the multistage tandem mass spectrometry,the characteristic peaks were extracted with mass spectrometry data peak matching,peak alignment,noise filtering.Principal component analysis(PCA)and partial least-squares discriminant analysis(PLS-DA)were used for data processing.Thechemical compositions were identified and tentative presumed according to MS accurate mass and MS/MS spectrometry fragmentation information,combined with the software of database search and comparison with reference standards and literature.The results show that the chemical compositions in Xanthii Fructus before and after stir-frying are clearly distinguished.A total of 44 different chemical compositions are detected in Xanthii Fructus before and after stir-frying,and 41 chemical compositions of which are identified.Among of them,there are 10 kinds of common differential compositions,such as liquiritigenin 4′-O-apiosyl-O-glucoside,3′,4′,5,7-tetramethoxyflavone,chlorogenic acid,deoxyadenosine,4-dicaffeoylquinic acid,1,3-dicaffeoylquinic acid,3,4-dicaffeoylquinic acid,astragalin,4′-desulphate-atractylosid andβ-carotene, which present different change laws.In the 10 differential components,the contents of liquiritigenin 4′-O-apiosyl-O-glucoside,deoxyadenosine,1,3-dicaffeoylquinic acid,3,4-dicaffeoylquinic acid,astragalin,andβ-carotene are much higher in Xanthii Fructus after stir-frying,while the contents of 3′,4′,5,7-tetramethoxyflavone,chlorogenic acid,4-dicaffeoylquinic acid,and 4′-desulphate-atractylosid are lower.This study provides a basic information for revealing the change law of chemical compositions in Xanthii Fructus before and after stir-frying.
引文
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[2]RODRIGUEZ E,TOWERS G H N,MITCHELL J C.Biological activities of sesquiterpene lactones[J].Biochemical Systematics&Ecology,1986,15:1 573-1 580.
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[4]代英辉,崔征,李建林.苍耳属植物化学成分及药理作用研究进展[J].沈阳药科大学学报,2007,24(12):786-790.DAI Yinghui,CUI Zheng,LI Jianlin.Research progress on chemical constituents and pharmacological activities of the Xanthium sibiricum[J].Journal of Shenyang Pharmaceutical University,2007,24(12):786-790(in Chinese).
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[6]韩婷,李慧梁,胡园,等.苍耳子中酚酸类化合物及不同品种和居群苍耳子中总酚酸含量的测定[J].中国中西医结合学报,2006,4(2):194-198.HAN Ting,LI Huiliang,HU Yuan,et al.Phenolic acids in Frucutus Xanthii and determination of contents of total phenolic acids in diffenert species and populations of Xanthium in China[J].Journal of Chinese Integrative Medicine,2006,4(2):194-198(in Chinese).
[7]宋琳琳,沙靖全,赵宏,等.苍耳草中总酚酸的含量测定及其抗炎作用研究[J].时珍国医国药,2013,24(10):2 331-2 332.SONG Linlin,SHA Jingquan,ZHAO Hong,et al.Determination of TPA content of Xanthium sibiricum Patrin exWidder and anti-inflammatory effect[J].Lishizhen Medicine and Materia Medica Research,2013,24(10):2 331-2 332(in Chinese).
[8]曹亮,周建军.蒽醌类化合物的研究进展[J].西北药学杂志,2009,24(3):237-238.CAO Liang,ZHOU Jianjun.Progress anthraquinone compounds[J].Northwest Pharmaceutical Journa,2009,24(3):237-238(in Chinese).
[9]钟地长,张淑凤,陈振锋,等.天然产物黄酮类化合物的提取、纯化及其金属配合物的研究进展[J].化学世界,2006,47(9):561-564.ZHONG Dichang,ZHANG Shufeng,CHEN Zhenfeng,et al.Research progress on the extraction and purification of natural flavonoides and their metal complexes[J].Chemical World,2006,47(9):561-564(in Chinese).
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[12]朵睿,刘玉红,王明奎,等.HPLC同时测定苍耳子中6个化学成分的含量[J].药物分析杂志,2013,33(1):78-82.DUO Rui,LIU Yuhong,WANG Mingkui,et al.HPLC simultaneous determination of the content of 6constituents in Fructus Xanthii[J].Chinese Journal of Pharmaceutical Analysis,2013,33(1):78-82(in Chinese).
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[14]洪燕,韩燕全,夏伦祝,等.超高效液相色谱法同时测定不同产地苍耳子9种酚酸类成分的含量[J].中国药学杂志,2013,48(13):1 109-1 112.HONG Yan,HAN Yanquan,XIA Lunzhu,et al.Simultaneous determination of nine phenolic acid components in Xanthii Fructus[J].Chinese Pharmaceutical Journal,2013,48(13):1 109-1 112(in Chinese).
[15]刘娟秀,罗益远,刘训红,等.毛细管电泳同时测定苍耳类药材中7种酚酸类成分的含量[J].中国药学杂志,2015,50(4):366-370.LIU Juanxiu,LUO Yiyuan,LIU Xunhong,et al.Simultaneous determination of seven phenolic acids from Xanthii Herba and Xanthii Fructus by HPCE[J].Chinese Pharmaceutical Journal,2015,50(4):366-370(in Chinese).
[16]刘娟秀,罗益远,刘训红,等.衍生化GC-MS同时测定苍耳子中14种脂肪酸的含量[J].天然产物研究与开发,2016,28(1):76-82.LIU Juanxiu,LUO Yiyuan,LIU Xunhong,et al.Simultaneous determination of fourteen fatty acids in Xanthii Fructus by derivatized GC-MS[J].Natural Product Research and Development,2016,28(1):76-82(in Chinese).
[17]刘娟秀,罗益远,刘训红,等.不同采收期苍耳草中酚酸类及蒽醌类成分的动态积累分析[J].中草药,2016,47(7):1 204-1 209.LIU Juanxiu,LUO Yiyuan,LIU Xunhong,et al.Dynamic changes of phenolic acids and anthraquinones in aerial parts of Xanthium sibiricumfrom different collection periods[J].Chinese Tradit Herbal Drugs,2016,47(7):1 204-1 209(in Chinese).
[18]王光忠,安靖,吴慧,等.苍耳子炒制前后毒性部位的高效液相指纹图谱研究[J].时珍国医国药,2013,24(3):663-665.WANG Guangzhong,AN Jing,WU Hui,et al.HPLC fingerprint of toxic sites in Xanthii Fructus before and after stir-frying[J].Lishizhen Medicine and Materia Medica Research,2013,24(3):663-665(in Chinese).
[19]秦泗涟,马利华,王振中,等.UPLC法同时测定炒苍耳子配方颗粒中5种酚酸类成分[J].中成药,2012,34(7):1 393-1 395.QIN Silian,MA Lihua,WANG Zhenzhong,et al.UPLC Determination fried cocklebur Granule 5kinds of phenolic acids[J].Chinese Traditional Patent Medicine,2012,34(7):1 393-1 395(in Chinese).
[20]奇小城,章弘扬,梁琼麟,等.液质联用技术及其在代谢组学研究中的应用[J].中成药,2009,31(1):106-112.QI Xiaocheng,ZHANG Hongyang,LIANG Qionglin,et al.LC-MS technology and the application in metabolomics research[J].Chinese Traditional Patent Medicine,2009,31(1):106-112(in Chinese).
[21]李坤平,高崇凯,李卫民.UPLC/ESI-TOF-MS/MS分析蛇床子提取物中香豆素类化合物[J].中成药,2009,31(4):584-587.LI Kunping,GAO Chongkai,LI Weimin.Analysis of coumarins in extract of Cnidium monnieri by UPLC/ESI-TOF-MS/MS[J].Chinese Traditional Patent Medicine,2009,31(4):584-587(in Chinese).
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