利用HPLC-IT-TOF-MS表征通关藤化学轮廓
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摘要
目的利用HPLC-IT-TOF-MS对通关藤的化学轮廓进行全面地解析。方法通关藤甲醇超声提取后,采用Waters AcquityUPLCHSST3色谱柱,乙腈-0.1%甲酸水溶液梯度洗脱;采用正、负离子自动多级质谱模式检测。利用多个孕甾烷类对照品推导该类化合物的质谱裂解规律。结果通过与对照品比对,准确归属了6个绿原酸类化合物和15个孕甾烷衍生物;通过相关文献数据结合质谱裂解规律推导,初步鉴定了100个孕甾烷类衍生物、4个黄酮类化合物和2个绿原酸类化合物。结论利用HPLC-IT-TOF-MS技术能快速、准确地对通关藤的化学轮廓进行全面解析,为通关藤及其制剂消癌平的质量标准及体内药效物质研究提供有效信息。
Objective To in depth analyze the chemical profile of Marsdenia tenacissima using HPLC-IT-TOF-MS.Methods The pulverized materials were exacted with methanol in an ultrasonication manner and then separated on a Waters Acquity UPLC HSS T3 column(100 mm×2.1 mm,1.8 μm,Milford,MA,USA) that was eluted in gradient with 0.1% formic acid-acetonitrile.The data was collected using automatically triggered tandem mass spectrometric mode in positive/negative ionization polarities.The mass fragmentation patterns of polyoxypregnane derivatives were proposed using some authentic compounds.Results Six chlorogenic acid derivatives and 15 polyoxypregnane derivatives were definitely assigned by referring to reference components,whereas the other signals,including 100 polyoxypregnane derivatives,four flavonoids,and two chlorogenic acid derivatives were tentatively annotated via matching the acquired information with those achieved information and the proposed mass fragmentation rules.Conclusion The research efficiently and accurately analyzed the chemical profile of M.tenacissima using HPLC-IT-TOF-MS,which will provide meaningful information for the quality evaluation and the therapeutic mechanism investigation of M.tenacissima as well as its preparation Xiao-Ai-Ping.
Objective To in depth analyze the chemical profile of Marsdenia tenacissima using HPLC-IT-TOF-MS.Methods The pulverized materials were exacted with methanol in an ultrasonication manner and then separated on a Waters Acquity UPLC HSS T3 column(100 mm×2.1 mm,1.8 μm,Milford,MA,USA) that was eluted in gradient with 0.1% formic acid-acetonitrile.The data was collected using automatically triggered tandem mass spectrometric mode in positive/negative ionization polarities.The mass fragmentation patterns of polyoxypregnane derivatives were proposed using some authentic compounds.Results Six chlorogenic acid derivatives and 15 polyoxypregnane derivatives were definitely assigned by referring to reference components,whereas the other signals,including 100 polyoxypregnane derivatives,four flavonoids,and two chlorogenic acid derivatives were tentatively annotated via matching the acquired information with those achieved information and the proposed mass fragmentation rules.Conclusion The research efficiently and accurately analyzed the chemical profile of M.tenacissima using HPLC-IT-TOF-MS,which will provide meaningful information for the quality evaluation and the therapeutic mechanism investigation of M.tenacissima as well as its preparation Xiao-Ai-Ping.
引文
[1]魏文静,刘同祥.民族药乌骨藤抗肿瘤药理活性及机制研究进展[J].时珍国医国药,2013,24(7):1717-1719.
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[10]Zhang J Y,Zhang Q,Li N,et al.Diagnostic fragment-ion-based and extension strategy coupled to DFIs intensity analysis for identification of chlorogenic acids isomers in Flos Lonicerae Japonicae by HPLC-ESI-MS(n)[J].Talanta,2013,104(2):1-9.
[11]Yang W Z,Ye M,Qiao X,et al.Collision-induced dissociation of 40 flavonoid aglycones and differentiation of the common flavonoid subtypes using electrospray ionization ion-trap tandem mass spectrometry and quadrupole time-of-flight mass spectrometry[J].Eur JMass Spectrom(Chichester),2012,18(6):493-503.
[12]Mc Garvey B D,Liao H,Ding K,et al.Dereplication of known pregnane glycosides and structural characterization of novel pregnanes in Marsdenia tenacissima by high-performance liquid chromatography and electrospray ionization-tandem mass spectrometry[J].J Mass Spectrom,2012,47(6):687-693.
[13]Yan Y,Song Q,Chen X,et al.Simultaneous determination of components with wide polarity and content ranges in Cistanche tubulosa using serially coupled reverse phase-hydrophilic interaction chromatography-tandem mass spectrometry[J].JChromatogr A,2017,1501:39-50.
[14]陈纪军,张壮鑫,周俊.通光藤甙F,G,H和I结构[J].云南植物研究,1999,21(3):369-377.
[15]杨仁洲,杨崇仁,周俊.通光藤苷元甲、乙和丙的结构[J].云南植物研究,1981,3(3):271-278.
[16]廖辉,单晓庆,王林,等.通关藤中甾体化合物的电喷雾质谱裂解规律研究[J].质谱学报,2010,31(2):103-109.
[17]Wang X L,Peng S L,Li-Sheng,et al.Further polyoxypregnane glycosides from Marsdenia tenacissima[J].J Asian Nat Prod Res,2010,12(8):654-661.
[18]Yao S,To K K,Wang Y Z,et al.Polyoxypregnane steroids from the stems of Marsdenia tenacissima[J].JNat Prod,2014,77(9):2044-2053.
[19]Chen J J,Li X Y,Sun C R,et al.Identification of polyoxypregnane glycosides from the stems of Marsdenia tenacissima by high-performance liquid chromatography/tandem mass spectrometry[J].Talanta,2008,77(1):152-159.
[20]Deng J,Liao Z X,Chen D F.Three new polyoxypregnane glycosides from Marsdenia tenacissima[J].Helv Chim Acta,2010,92(10):2111-2117.
[21]Pang X,Kang L P,Yu H S,et al.New polyoxypregnane glycosides from the roots of Marsdenia tenacissima[J].Steroids,2015,93:68-76.
[22]邢旺兴,陈斌,宓鹤鸣,等.通光藤中两个新C21甾体苷类成分[J].药学学报,2004,39(4):272-275.
[23]Deng J,Liao Z X,Chen D F.Marsdenosides A-H,polyoxypregnane glycosides from Marsdenia tenacissima[J].Phytochemistry,2005,66(9):1040-1051.
[24]Luo S Q,Lin L Z,Cordell G A,et al.Polyoxypregnanes from Marsdenia tenacissima[J].Phytochmistry,1993,34(6):1615-1620.
[25]Xia Z H,Mao S L,Lao A N,et al.Five new pregnane glycosides from the stems of Marsdenia tenacissima[J].JAsian Nat Prod Res,2011,13(6):477-485.
[26]Yao S,To K K,Ma L,et al.Polyoxypregnane steroids with an open-chain sugar moiety from Marsdenia tenacissima and their chemoresistance reversal activity[J].Phytochemistry,2016,126:47-58.
[27]Li Q F,Wang X L,Ding L S,et al.Polyoxypregnanes from the stems of Marsdenia tenacissima[J].Chin Chem Lett,2007,18(7):831-834.
[28]Miyakawa S,Yamaura K,Hayashi K,et al.Five glycosides from the Chinese drug‘TONG-GUANG-SAN’:The stems of Marsdenia tenacissima[J].Phytochemistry,1986,25(12):2861-2865.
[2]王艳艳,王威,李红岩,等.牛奶菜属植物化学成分研究进展[J].天然产物研究与开发,2009,21(24):163-170.
[3]陈静,马明芳,格桑顿珠,等.牛奶菜属植物化学成分及药理活性研究进展[J].西藏大学学报,2012,27(1):40-50.
[4]Wang P L,Sun Z,Lv X J,et al.A homologues prediction strategy for comprehensive screening and characterization of C21 steroids from Xiao-ai-ping injection by using ultra high performance liquid chromatography coupled with high resolution hybrid quadrupole-orbitrap mass spectrometry[J].J Pharm Biomed Anal,2018,148:80-88.
[5]Chen J,Li X,Sun C,et al.Identification of polyoxypregnane glycosides from the stems of Marsdenia tenacissima by high-performance liquid chromatography tandem mass spectrometry[J].Talanta,2008,77(1):152-159.
[6]Su X Q,Song Y L,Zhang J,et al.Dihydrochalcones and homoisoflavanes from the red resin of Dracaena cochinchinensis(Chinese dragon’s blood)[J].Fitoterapia,2014,99:64-71.
[7]Sun J,Song Y L,Zhang J,et al.Characterization and quantitative analysis of phenylpropanoid amides in eggplant(Solanum melongena L.)by high performance liquid chromatography coupled with diode array detection and hybrid ion trap time-of-flight mass spectrometry[J].JAgric Food Chem,2015,63(13):3426-3436.
[8]Sun J,Song Y,Sun H,et al.Characterization and quantitative analysis of phenolic derivatives in Longxuetongluo Capsule by HPLC-DAD-IT-TOF-MS[J].J Pharm Biomed Anal,2017,145:462-472.
[9]Zhang J Y,Wang Z J,Li Y,et al.A strategy for comprehensive identification of sequential constituents using ultra-high-performance liquid chromatography coupled with linear ion trap-orbitrap mass spectrometer,application study on chlorogenic acids in Flos Lonicerae Japonicae[J].Talanta,2016,147(62):16-27.
[10]Zhang J Y,Zhang Q,Li N,et al.Diagnostic fragment-ion-based and extension strategy coupled to DFIs intensity analysis for identification of chlorogenic acids isomers in Flos Lonicerae Japonicae by HPLC-ESI-MS(n)[J].Talanta,2013,104(2):1-9.
[11]Yang W Z,Ye M,Qiao X,et al.Collision-induced dissociation of 40 flavonoid aglycones and differentiation of the common flavonoid subtypes using electrospray ionization ion-trap tandem mass spectrometry and quadrupole time-of-flight mass spectrometry[J].Eur JMass Spectrom(Chichester),2012,18(6):493-503.
[12]Mc Garvey B D,Liao H,Ding K,et al.Dereplication of known pregnane glycosides and structural characterization of novel pregnanes in Marsdenia tenacissima by high-performance liquid chromatography and electrospray ionization-tandem mass spectrometry[J].J Mass Spectrom,2012,47(6):687-693.
[13]Yan Y,Song Q,Chen X,et al.Simultaneous determination of components with wide polarity and content ranges in Cistanche tubulosa using serially coupled reverse phase-hydrophilic interaction chromatography-tandem mass spectrometry[J].JChromatogr A,2017,1501:39-50.
[14]陈纪军,张壮鑫,周俊.通光藤甙F,G,H和I结构[J].云南植物研究,1999,21(3):369-377.
[15]杨仁洲,杨崇仁,周俊.通光藤苷元甲、乙和丙的结构[J].云南植物研究,1981,3(3):271-278.
[16]廖辉,单晓庆,王林,等.通关藤中甾体化合物的电喷雾质谱裂解规律研究[J].质谱学报,2010,31(2):103-109.
[17]Wang X L,Peng S L,Li-Sheng,et al.Further polyoxypregnane glycosides from Marsdenia tenacissima[J].J Asian Nat Prod Res,2010,12(8):654-661.
[18]Yao S,To K K,Wang Y Z,et al.Polyoxypregnane steroids from the stems of Marsdenia tenacissima[J].JNat Prod,2014,77(9):2044-2053.
[19]Chen J J,Li X Y,Sun C R,et al.Identification of polyoxypregnane glycosides from the stems of Marsdenia tenacissima by high-performance liquid chromatography/tandem mass spectrometry[J].Talanta,2008,77(1):152-159.
[20]Deng J,Liao Z X,Chen D F.Three new polyoxypregnane glycosides from Marsdenia tenacissima[J].Helv Chim Acta,2010,92(10):2111-2117.
[21]Pang X,Kang L P,Yu H S,et al.New polyoxypregnane glycosides from the roots of Marsdenia tenacissima[J].Steroids,2015,93:68-76.
[22]邢旺兴,陈斌,宓鹤鸣,等.通光藤中两个新C21甾体苷类成分[J].药学学报,2004,39(4):272-275.
[23]Deng J,Liao Z X,Chen D F.Marsdenosides A-H,polyoxypregnane glycosides from Marsdenia tenacissima[J].Phytochemistry,2005,66(9):1040-1051.
[24]Luo S Q,Lin L Z,Cordell G A,et al.Polyoxypregnanes from Marsdenia tenacissima[J].Phytochmistry,1993,34(6):1615-1620.
[25]Xia Z H,Mao S L,Lao A N,et al.Five new pregnane glycosides from the stems of Marsdenia tenacissima[J].JAsian Nat Prod Res,2011,13(6):477-485.
[26]Yao S,To K K,Ma L,et al.Polyoxypregnane steroids with an open-chain sugar moiety from Marsdenia tenacissima and their chemoresistance reversal activity[J].Phytochemistry,2016,126:47-58.
[27]Li Q F,Wang X L,Ding L S,et al.Polyoxypregnanes from the stems of Marsdenia tenacissima[J].Chin Chem Lett,2007,18(7):831-834.
[28]Miyakawa S,Yamaura K,Hayashi K,et al.Five glycosides from the Chinese drug‘TONG-GUANG-SAN’:The stems of Marsdenia tenacissima[J].Phytochemistry,1986,25(12):2861-2865.