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Article(id=1198622900287800064, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198622898320671473, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2022-0782, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1656432000000, receivedDateStr=2022-06-29, revisedDate=1666972800000, revisedDateStr=2022-10-29, acceptedDate=null, acceptedDateStr=null, onlineDate=1763703568764, onlineDateStr=2025-11-21, pubDate=1673452800000, pubDateStr=2023-01-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1763703568764, onlineIssueDateStr=2025-11-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1763703568764, creator=13701087609, updateTime=1763703568764, updator=13701087609, issue=Issue{id=1198622898320671473, tenantId=1146029695717560320, journalId=1189982191388893191, year='2023', volume='58', issue='1', pageStart='1', pageEnd='234', issueExtLink='null', onlineDate='null', pubDate='1673452800000', pubDateStr='2023-01-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1763703568296, creator='13701087609', updateTime=1763703697615, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1198623440782586642, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198622898320671473, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1198623440782586643, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198622898320671473, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=186, endPage=192, ext={EN=ArticleExt(id=1198622900602372875, articleId=1198622900287800064, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Structure identification and content analysis of active components in Xiaoyao pills, columnId=null, journalTitle=Acta Pharmaceutica Sinica, columnName=null, runingTitle=null, highlight=null, articleAbstract=

Xiaoyao pills are a famous traditional Chinese medicine collected in Welfare Pharmacy, which is a classic prescription for treating liver depression and spleen deficiency. However, its composition is complex. In order to better control the quality of Xiaoyao pills, in this study, HPLC-ion-trap time-of-flight mass spectrometry (LC-IT-TOF/MS) was used to identify the main ingredients of Xiaoyao pills, paeoniflorin, albiflorin, glycyrrhizic acid, saikosaponin A and saikosaponin B2. Then a liquid chromatography tandem mass spectrometry (LC-MS/MS) was developed for simultaneous determination and quantification of the main compounds. Fragmentation pathways of five active components were obtained. The method was validated. Five active ingredients in Xiaoyao pills had a good linear relationship, and the values of RSD (%) of repeatability were all less than 5%, the recovery ranges were between 90% and 115%, and the values of RSD (%) of each substance were less than 10% after the sample solution is placed for 24 hours. Three batches of Xiaoyao pills (concentrated pellets) and two batches of Xiaoyao pills (water pellets) were determined, the contents of paeoniflorin in concentrated pills were more than 4.0 mg·g-1, and those in water pills were more than 2.5 mg·g-1, which was accordance with Chinese Pharmacopoeia. However, other compounds behave differently. This method has high sensitivity and reliable measurement results, which provides basis for quality control of Xiaoyao pills and material basis for pharmacology research.

, authors=null, authorsList=Jie FU, Jin-bo YU, Lin CONG, Zhen-xiong ZHAO, Yan WANG, authorCompany=null, correspAuthors=Yan WANG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2023 Acta Pharmaceutica Sinica. All rights reserved., copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, fund=null), CN=ArticleExt(id=1198622903005709135, articleId=1198622900287800064, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=逍遥丸活性成分的结构鉴定及含量分析, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

逍遥丸源自《太平惠民和剂局方》，是治疗肝郁脾虚证的经典方，但是其成分复杂，为更好地进行逍遥丸的质量控制，本研究采用LC-IT-TOF/MS方法对逍遥丸中的芍药苷、芍药内酯苷、甘草酸、柴胡皂苷A和柴胡皂苷B2等5种有效成分进行了定性研究，采用LC-MS/MS方法对上述5种有效成分进行了定量研究，并进行了方法学验证。结果表明，通过高分辨质谱可以得到5种有效成分的质谱裂解规律。测定逍遥丸中5种有效成分含量的分析方法，线性关系良好、重复性的RSD均小于5%、回收率范围在90%~115%之间、样品溶液放置24 h测定各物质RSD小于10%。对3批逍遥丸（浓缩丸）和2批逍遥丸（水丸）样品进行测定，表明3批浓缩丸中含有的芍药苷含量大于4 mg·g-1，2批水丸中含有的芍药苷含量大于2.5 mg·g-1，符合2020年版中国药典规定，但是不同批次其他成分的含量存在差异。该方法灵敏度高，测定结果可靠，为逍遥丸的质量控制研究提供依据，为深入研究逍遥丸的药效物质基础提供了有价值的科学依据。

, authors=null, authorsList=符洁, 于金波, 丛林, 赵朕雄, 王琰, authorCompany=null, correspAuthors=王琰, authorNote=null, correspAuthorsNote=
*王琰, Tel: 86-10-63165238, E-mail:
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Rapid Commun Mass Spectrom, 2010, 24: 3261-3270., articleTitle=Structural characterization and identification of oleanane-type triterpene saponins in Glycyrrhiza uralensis Fischer by rapid-resolution liquid chromatography coupled with time-of-flight mass spectrometry, refAbstract=null)], funds=[Fund(id=1198702083470885454, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, awardId=81973290, language=CN, fundingSource=国家自然科学基金(81973290), fundOrder=null, country=null), Fund(id=1198702083579937361, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, awardId=82173888, language=CN, fundingSource=国家自然科学基金(82173888), fundOrder=null, country=null), Fund(id=1198702083730932315, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, awardId=Z141102004414062, language=CN, fundingSource=北京市创新药物非临床药物代谢及药代/药效研究重点实验室(Z141102004414062), fundOrder=null, country=null), Fund(id=1198702083919675999, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, awardId=2021-I2M-1-028, language=CN, fundingSource=中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-028), fundOrder=null, country=null), Fund(id=1198702084091642468, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, awardId=2021-I2M-1-007, language=CN, fundingSource=中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-007), fundOrder=null, country=null), Fund(id=1198702084213277295, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, awardId=2022-I2M-2-002, language=CN, fundingSource=中国医学科学院医学与健康科技创新工程项目(2022-I2M-2-002), fundOrder=null, country=null)], companyList=[AuthorCompany(id=1198702075405238405, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, xref=null, ext=[AuthorCompanyExt(id=1198702075417821316, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, companyId=1198702075405238405, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing 100050, China), AuthorCompanyExt(id=1198702075426209926, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, companyId=1198702075405238405, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=中国医学科学院药物研究所, 天然药物活性物质与功能国家重点实验室, 北京 100050)])], figs=[ArticleFig(id=1198702081612808673, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=EN, label=null, caption=null, figureFileSmall=sNOTkEd7+lYM1/Wva16DHA==, figureFileBig=Ly+grgq7hBOG6zuZtZoxMg==, tableContent=null), ArticleFig(id=1198702081734443499, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=CN, label=Figure 1, caption= Fragmentation pathways of paeoniflorin (A), albiflorin (B), glycyrrhizic acid (C), saikosaponin A (D) and saikosaponin B2 (E) , figureFileSmall=sNOTkEd7+lYM1/Wva16DHA==, figureFileBig=Ly+grgq7hBOG6zuZtZoxMg==, tableContent=null), ArticleFig(id=1198702081881244150, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=EN, label=null, caption=null, figureFileSmall=Adzd71Ovj1tjXrF4FZW3dw==, figureFileBig=yQryTir6tSySORF8xgUXWg==, tableContent=null), ArticleFig(id=1198702081986101756, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=CN, label=Figure 2, caption= The samples extracted by different extraction solvent (A) and ultrasonic time (B) , figureFileSmall=Adzd71Ovj1tjXrF4FZW3dw==, figureFileBig=yQryTir6tSySORF8xgUXWg==, tableContent=null), ArticleFig(id=1198702082128708100, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=EN, label=null, caption=null, figureFileSmall=QISCFsFFnIhmuOXceeQcEw==, figureFileBig=5AUbpSSxTMZ9X3kOoMnAbg==, tableContent=null), ArticleFig(id=1198702082325840399, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=CN, label=Figure 3, caption= The MRM chromatograms of five active ingredients. 1: Paeoniflorin; 2: Albiflorin; 3: Glycyrrhizic acid; 4: Saikosaponin A; 5: Saikosaponin B2 , figureFileSmall=QISCFsFFnIhmuOXceeQcEw==, figureFileBig=5AUbpSSxTMZ9X3kOoMnAbg==, tableContent=null), ArticleFig(id=1198702082443280919, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Peak No. Compound name tR/min Molecular ion m/z Fragment ion MS2 Fragment ion MS3 Diff/ppm
1 Paeoniflorin 21.90 503.156 7 381.112 4, 324.096 2, 219.063 0, 185.047 3 2.58
2 Albiflorin 21.24 481.167 3 319.116 0, 197.082 8 179.068 3, 161.063 9 -6.44
3 Glycyrrhizic acid 37.45 823.426 3, 453.340 6 407.329 2 389.319 3 -3.16
4 Saikosaponin A 39.19 779.464 2 617.410 5 -6.42
5 Saikosaponin B2 39.19 779.464 2 617.410 5 -6.42
), ArticleFig(id=1198702082556527134, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622900287800064, language=CN, label=Table 1, caption=

Retention time and the mass data for five active ingredients

, figureFileSmall=null, figureFileBig=null, tableContent=
Peak No. Compound name tR/min Molecular ion m/z Fragment ion MS2 Fragment ion MS3 Diff/ppm
1 Paeoniflorin 21.90 503.156 7 381.112 4, 324.096 2, 219.063 0, 185.047 3 2.58
2 Albiflorin 21.24 481.167 3 319.116 0, 197.082 8 179.068 3, 161.063 9 -6.44
3 Glycyrrhizic acid 37.45 823.426 3, 453.340 6 407.329 2 389.319 3 -3.16
4 Saikosaponin A 39.19 779.464 2 617.410 5 -6.42
5 Saikosaponin B2 39.19 779.464 2 617.410 5 -6.42
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Compound name Calibration curve Range/ng·mL-1 r LOD/ng·mL-1 LOQ/ng·mL-1
Paeoniflorin Y = 65.153 x + 227.530 10-1 000 0.999 2 1 2
Albiflorin Y = 210.599 x + 261.776 10-1 000 0.999 6 2 10
Glycyrrhizic acid Y = 260.907 x - 99.748 5-500 0.999 5 1 2
Saikosaponin A Y = 232.795 x + 135.147 5-500 0.999 4 0.5 1
Saikosaponin B2 Y = 244.611 x + 106.570 5-500 0.999 0 0.5 1
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The calibration curves, linear ranges and correlation coefficients for regression, LODs and LOQs for the compounds

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Compound name Calibration curve Range/ng·mL-1 r LOD/ng·mL-1 LOQ/ng·mL-1
Paeoniflorin Y = 65.153 x + 227.530 10-1 000 0.999 2 1 2
Albiflorin Y = 210.599 x + 261.776 10-1 000 0.999 6 2 10
Glycyrrhizic acid Y = 260.907 x - 99.748 5-500 0.999 5 1 2
Saikosaponin A Y = 232.795 x + 135.147 5-500 0.999 4 0.5 1
Saikosaponin B2 Y = 244.611 x + 106.570 5-500 0.999 0 0.5 1
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Content/mg·g-1 SX20170209 ZJ170907 JZT201703001 SY10917060114 KH20161206
Paeoniflorin 7.23 8.07 7.74 5.24 5.57
Albiflorin 3.13 3.29 2.56 2.02 1.60
Glycyrrhizic acid 1.53 0.23 0.06 < LOQ < LOQ
Saikosaponin A 0.07 0.04 0.03 1.04 0.29
Saikosaponin B2 0.13 0.32 0.03 0.22 0.01
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The mean contents of five active compounds in Xiaoyao pills (n = 6). SX20170209: Shanxi Tianyang Pharmaceutical Co., Ltd.; ZJ170907: Zhongjing Wanxi Pharmaceutical Co., Ltd.; JZT20170300: Jiuzhitang Co., Ltd.; KH20161206: Heilongjiang Sunflower Pharmaceutical Co., Ltd.; SY10917060114: Hebei Yongfeng Pharmaceutical Co., Ltd.

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Content/mg·g-1 SX20170209 ZJ170907 JZT201703001 SY10917060114 KH20161206
Paeoniflorin 7.23 8.07 7.74 5.24 5.57
Albiflorin 3.13 3.29 2.56 2.02 1.60
Glycyrrhizic acid 1.53 0.23 0.06 < LOQ < LOQ
Saikosaponin A 0.07 0.04 0.03 1.04 0.29
Saikosaponin B2 0.13 0.32 0.03 0.22 0.01
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逍遥丸活性成分的结构鉴定及含量分析
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符洁 , 于金波 , 丛林 , 赵朕雄 , 王琰 *
药学学报 | 研究论文 2023,58(1): 186-192
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药学学报 |研究论文 2023 , 58 (1) : 186 -192
逍遥丸活性成分的结构鉴定及含量分析
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符洁, 于金波, 丛林, 赵朕雄, 王琰*
作者信息
  • 中国医学科学院药物研究所, 天然药物活性物质与功能国家重点实验室, 北京 100050
通讯作者:
*王琰, Tel: 86-10-63165238, E-mail:
Structure identification and content analysis of active components in Xiaoyao pills
Jie FU, Jin-bo YU, Lin CONG, Zhen-xiong ZHAO, Yan WANG*
Affiliations
  • State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing 100050, China
出版时间: 2023-01-12 doi: 10.16438/j.0513-4870.2022-0782
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摘要
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逍遥丸源自《太平惠民和剂局方》，是治疗肝郁脾虚证的经典方，但是其成分复杂，为更好地进行逍遥丸的质量控制，本研究采用LC-IT-TOF/MS方法对逍遥丸中的芍药苷、芍药内酯苷、甘草酸、柴胡皂苷A和柴胡皂苷B2等5种有效成分进行了定性研究，采用LC-MS/MS方法对上述5种有效成分进行了定量研究，并进行了方法学验证。结果表明，通过高分辨质谱可以得到5种有效成分的质谱裂解规律。测定逍遥丸中5种有效成分含量的分析方法，线性关系良好、重复性的RSD均小于5%、回收率范围在90%~115%之间、样品溶液放置24 h测定各物质RSD小于10%。对3批逍遥丸（浓缩丸）和2批逍遥丸（水丸）样品进行测定，表明3批浓缩丸中含有的芍药苷含量大于4 mg·g-1，2批水丸中含有的芍药苷含量大于2.5 mg·g-1，符合2020年版中国药典规定，但是不同批次其他成分的含量存在差异。该方法灵敏度高，测定结果可靠，为逍遥丸的质量控制研究提供依据，为深入研究逍遥丸的药效物质基础提供了有价值的科学依据。

逍遥丸  /  LC-IT-TOF/MS  /  LC-MS/MS  /  结构鉴定  /  含量分析

Xiaoyao pills are a famous traditional Chinese medicine collected in Welfare Pharmacy, which is a classic prescription for treating liver depression and spleen deficiency. However, its composition is complex. In order to better control the quality of Xiaoyao pills, in this study, HPLC-ion-trap time-of-flight mass spectrometry (LC-IT-TOF/MS) was used to identify the main ingredients of Xiaoyao pills, paeoniflorin, albiflorin, glycyrrhizic acid, saikosaponin A and saikosaponin B2. Then a liquid chromatography tandem mass spectrometry (LC-MS/MS) was developed for simultaneous determination and quantification of the main compounds. Fragmentation pathways of five active components were obtained. The method was validated. Five active ingredients in Xiaoyao pills had a good linear relationship, and the values of RSD (%) of repeatability were all less than 5%, the recovery ranges were between 90% and 115%, and the values of RSD (%) of each substance were less than 10% after the sample solution is placed for 24 hours. Three batches of Xiaoyao pills (concentrated pellets) and two batches of Xiaoyao pills (water pellets) were determined, the contents of paeoniflorin in concentrated pills were more than 4.0 mg·g-1, and those in water pills were more than 2.5 mg·g-1, which was accordance with Chinese Pharmacopoeia. However, other compounds behave differently. This method has high sensitivity and reliable measurement results, which provides basis for quality control of Xiaoyao pills and material basis for pharmacology research.

Xiaoyao pills  /  LC-IT-TOF/MS  /  LC-MS/MS  /  structure identification  /  content analysis
符洁, 于金波, 丛林, 赵朕雄, 王琰. 逍遥丸活性成分的结构鉴定及含量分析. 药学学报, 2023 , 58 (1) : 186 -192 . DOI: 10.16438/j.0513-4870.2022-0782
Jie FU, Jin-bo YU, Lin CONG, Zhen-xiong ZHAO, Yan WANG. Structure identification and content analysis of active components in Xiaoyao pills[J]. Acta Pharmaceutica Sinica, 2023 , 58 (1) : 186 -192 . DOI: 10.16438/j.0513-4870.2022-0782
正文
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逍遥丸是由《太平惠民合剂局方》中收载的名方逍遥散改变剂型而来, 处方中含有柴胡、当归、白芍、白术、茯苓、甘草等中药, 其中柴胡是君药, 当归和白芍为臣药, 白术、茯苓为佐药, 甘草为使药。逍遥丸具有调和肝脾、疏肝解郁、养血健脾的功效, 用于治疗肝郁脾虚所致的郁闷不舒、胸胁胀痛、头晕目眩、食欲减退、月经不调等疾病, 近年来逍遥丸的抗抑郁作用也被广泛报道[1-9]。逍遥丸作为复方药物, 化学成分复杂, 其中柴胡中的柴胡皂苷、白芍中的芍药苷、芍药内酯苷以及甘草中的甘草酸均为其活性成分, 具有抗炎、抗病毒、神经调节、免疫调节、保护肝脏等作用[10-15]。在2020年版中国药典, 逍遥丸的质量控制项下含量测定采用高效液相色谱法, 并且质量控制物质仅有芍药苷一种物质[1]。对于一个复方制剂, 仅仅控制一个指标成分难以做到有效地控制药品的质量。目前, 文献[16-24]报道了多种逍遥丸的质量控制研究方法, 如HPLC法、毛细管电泳法、气相色谱法、GC-MS法等。其中, 高效液相色谱法以其稳定、可靠、高效的特点广泛地应用于中药成分分析中, 但是在定性研究中高效液相色谱峰能提供的信息相当局限, 在含量分析研究中高效液相色谱法需要将各个化合物成分完全分离, 而且目标成分如果是紫外末端吸收, 那么基线易漂移, 因此这些特点对分析中药复杂成分高效液相色谱法表现出了局限性。而液相质谱联用技术, 在色谱分离的基础上能够提供化合物精确的分子离子峰甚至多级离子碎片, 为解析化合物的结构提供部分依据, 而更高的灵敏度对分析微量成分更具优势。结合逍遥丸成分多样, 并且君药柴胡中柴胡皂苷A最大吸收波长210 nm属于末端吸收, 本研究将采用LC-IT-TOF/MS对逍遥丸中的主要成分进行定性研究, 依据准确的MSn谱中的分子量和片段信息, 鉴定逍遥丸中化学成分。然后采用液相色谱串联质谱法(LC-MS/MS) 同时对芍药苷、芍药内酯苷、甘草酸、柴胡皂苷A和柴胡皂苷B2等5种化合物进行定量分析, 并对该方法进行了方法学验证。利用建立含量分析方法的分析比较了5批不同厂家生产的逍遥丸中5种化合物的含量, 得到不同工艺条件下制成的逍遥丸主要成分的差别, 为逍遥丸的质量控制研究提供科学依据。
材料与方法
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仪器  岛津高效液相-电喷雾-离子阱-飞行时间质谱仪、岛津LCMS-8050高效液相色谱-电喷雾-三重四极杆串联质谱仪[日本岛津企业管理(中国) 有限公司], METTLER TOLEDO XS105分析天平(瑞士METTLER公司), 超声波清洗机(北京天林恒泰科技有限公司)。
药品与材料  芍药苷(含量: 98.57%)、芍药内酯苷(含量: 98.32%)、甘草酸(含量: 99.35%)、柴胡皂苷A (含量: 99.54%) 和柴胡皂苷B2 (含量: 99.86%), 均购自索莱宝生物科技有限公司(北京); 乙腈、甲醇(HPLC级), 美国Fisher Scientific公司; 水为娃哈哈纯净水; 其他化学试剂均为分析级(中国北京国药控股化学试剂有限公司)。3批逍遥丸(浓缩丸) 分别产自陕西天洋制药有限责任公司(批号20170209)、仲景宛西制药股份有限公司(批号170907) 和九芝堂股份有限公司(批号201703001); 2批逍遥丸(水丸) 分别产自黑龙江葵花药业股份有限公司(批号20161206) 和石药控股集团河北永丰药业有限公司(批号10917060114)。
LC-IT-TOF/MS检测方法  液相条件: 流动相: 0.1甲酸水溶液(A)-乙腈(B) 梯度洗脱, 梯度条件如下: 0~10 min, 5% B; 10~15 min, 5%~20% B; 15~45 min, 20%~60% B; 45~60 min, 60%~85% B; 60~65 min, 5% B。色谱柱: Alltima C18 (250 mm × 4.6 mm, 5 μm); 流速: 0.8 mL·min-1; 柱温: 35 ℃。柱后质谱与废液的分流比3∶5, 质谱条件: 离子化模式: ESI源, 分析模式: 正负离子切换模式扫描, 雾化气流: 1.5 L·min-1, CDL温度: 200 ℃, 加热模块温度: 200 ℃, 检测器电压: 1.75 kV, 碰撞能量: 50%, 干燥气压力: 115 kPa, 质谱一级数据采集范围: m/z 100~1 000, 多级数据采集采用自动模式。进样量20 μL。
LC-MS/MS检测方法  液相条件: 色谱柱Alltima HP C18柱(2.1 mm × 100 mm, 5 μm), 流动相: 0.1%甲酸水溶液(A)-甲醇和乙腈混合液(比例为2∶1) (B), 梯度洗脱0~1 min, 20% B; 1~3 min, 20%~40% B; 3~6 min, 40%~70% B; 6~8.5 min, 70% B; 8.5~12 min, 20% B。流速: 0.3 mL·min-1, 柱温35 ℃, 进样量1 μL。质谱条件为离子源: ESI源; 雾化气(nebulizing): 2.9 L·min-1; 干燥气(drying gas): 10 L·min-1; 加热气流(heating gas): 10 L·min-1; 接口(interface) 温度: 300 ℃; DL温度: 250 ℃; 加热块温度: 400 ℃; CID气流(CID gas): 270 kPa; 检测方式: 正离子模式检测; 扫描方式: 多反应监测模式, 用于定量分析离子反应对为: 芍药内酯苷m/z 481.00→104.95 (CE: -22 eV); 芍药苷m/z 503.05→219.25 (CE: -40.0 eV), 甘草酸m/z 844.90→493.05 (CE: -40 eV); 柴胡皂苷A m/z 803.10→330.85 (CE: -53 eV); 柴胡皂苷B2 m/z 803.10→330.90 (CE: -50 eV)。
样品制备
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定性用供试品溶液的制备  取逍遥丸适量, 研细, 取约0.5 g, 精密称定, 置于具塞锥形瓶中, 加入甲醇10 mL, 密塞, 称定重量, 超声处理(功率250 W, 频率30 kHz) 1 h, 放冷, 再称重, 甲醇补足减少的重量, 摇匀, 过0.45 μm的滤膜, 取续滤液待分析。
定量用供试品溶液的配制  取逍遥丸适量, 研细, 精密称定约50.0 mg置于250 mL量瓶中, 加入甲醇适量, 超声处理(功率250 W, 频率30 kHz) 3 h, 放冷, 加甲醇至刻线, 摇匀, 过0.45 μm的滤膜, 取续滤液用于检测芍药内酯苷、甘草酸、柴胡皂苷A和柴胡皂苷B2的分析。将此溶液稀释4倍, 用于检测芍药苷。
对照品储备液配制  精密称取对照品芍药内酯苷、芍药苷、甘草酸、柴胡皂苷A和柴胡皂苷B2各10.0 mg分别置于100 mL量瓶中, 加甲醇并定容至刻度, 制成各单一成分的对照品储备液。
线性关系考察标准系列溶液的配制  精密吸取芍药内酯苷和芍药苷对照品储备液各2.5 mL, 甘草酸、柴胡皂苷A和柴胡皂苷B2对照品储备液各1.25 mL, 置于250 mL量瓶中, 加入甲醇定容稀释得到混合对照品储备溶液, 将混合对照品储备溶液稀释2倍、5倍、10倍、20倍、100倍得到芍药内酯苷和芍药苷的系列浓度为: 1 000、500、200、100、50和10 ng·mL-1; 甘草酸、柴胡皂苷A和柴胡皂苷B2的系列浓度为: 500、250、100、50、25和5 ng·mL-1。
仪器精密度溶液配制  配制6份含有芍药内酯苷和芍药苷质量浓度为100 ng·mL-1, 甘草酸、柴胡皂苷A和柴胡皂苷B2质量浓度为50 ng·mL-1的混合溶液。
回收率考察溶液的配制  精密称取供试品(批号: SX20170209) 9份, 每份约50 mg, 分别置9个250 mL量瓶中, 加甲醇适量, 超声处理3 h, 冷却后, 精密量取对照品混合溶液1.0、1.25和1.5 mL各3份, 分别置上述9个250 mL量瓶中, 用甲醇稀释至刻度, 摇匀, 过滤, 作为供试品溶液。
结果
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1 逍遥丸主要成分鉴定
通过逍遥丸样品与单一对照品的色谱和质谱比对方式, 鉴定了5个活性成分, 分别是芍药苷、芍药内酯苷、甘草酸、柴胡皂苷A和柴胡皂苷B2, 表 1列出了5个活性物质的多级质谱信息。
对5个活性成分的多级质谱裂解过程进行分析:
芍药苷和芍药内酯苷是同分异构体, 分子式为C23H28O11。在质谱裂解上二者表现出不同的裂解方式。质谱结果显示芍药苷在m/z 503.151 7处为准分子离子峰, 为[M+Na]+。母离子失去122 Da得到二级碎片离子381.112 4, 即[M+Na-C6H5CO-H2O]+, 进而二级碎片离子381.112 4失去162 Da得到碎片离子219.063 0, 这是因为糖苷键的断裂即[M+Na-C6H5CO-H2O-C6H11O5]+。芍药内酯苷在m/z 481.201 0处为准分子离子峰, 为[M+H]+。母离子失去162 Da得到二级碎片离子319.116 0, 裂解方式是糖苷键断裂, 即[M+H-C6H11O5]+。二级碎片离子197.082 5是由于母离子481.201 0失去284 Da [M+H-C6H5CO-C6H11O5-H2O]+, 与芍药苷不同的是芍药内酯苷的二级碎片离子197.082 5失去一分子H2O, 得到三级碎片179.068 3, 即[M+H-C6H5CO-C6H11O5-H2O-H2O]+。裂解过程与文献[25]一致。
据文献[26]甘草中三萜皂苷类化合物质谱裂解规律, 解析甘草酸的多级质谱规律。甘草酸, 分子式为C42H62O16, 在m/z 823.420 2处为准分子离子峰, 为[M+H]+母离子中性丢失370 Da得到碎片453.340 6, 即失去2个葡萄糖醛酸得到[M+H-2GlcA]+, 碎片离子453.340 6中性失去46 Da, 即[M+H-2GlcA-HCOOH]+, 得到碎片离子407.329 2, 碎片离子407.329 2中性丢失18 Da, [M+H-2GlcA-HCOOH-H2O]+即得到碎片389.319 3。
柴胡皂苷A和柴胡皂苷B2为同分异构体, 分子式为C42H68O13, 在m/z 779.464 2处为准分子离子峰, 为[M-H]-, 两个化合物均只得到了二级碎片617.410 6, 是由母离子一个糖苷键的断裂得到, 即[M-H-C6H11O5]-。在结构鉴定的研究中未区分开此对同分异构体, 在含量分析中, 通过改变色谱分离条件, 将柴胡皂苷A和柴胡皂苷B2进行分离从而得到鉴定。
以上各化合物的裂解过程见图 1。
2 逍遥丸含量分析研究
2.1 样品提取的优化
考察甲醇不同浓度及不同超声时间对提取逍遥丸成分的影响, 采用LC-IT-TOF/MS法和LC-MS/MS法分别测定, 比较提取化合物的种类和5个主要成分的含量选择100%甲醇超声3 h提取的方法, 不同时间和甲醇浓度提取下的结果如图 2所示。
2.2 方法学验证
2.2.1 专属性
分别向LC-MS/MS注入空白溶剂、混合对照品溶液及逍遥丸样品溶液。结果表明各个化合物的分离效果良好, 如图 3所示。
2.2.2 线性关系
以溶液的浓度(x) 为横坐标, 峰面积(Y) 为纵坐标绘制回归曲线, 芍药苷、芍药内酯苷线性范围10~1 000 ng·mL-1, 甘草酸、柴胡皂苷A和柴胡皂苷B2的线性范围为5~500 ng·mL-1, 相关系数均大于0.999。回归方程、线性范围和相关系数如表 2所示。
2.2.3 仪器精密度
结果表明, 芍药苷、白芍苷、甘草酸、柴胡皂苷A、柴胡皂苷B2的RSD (%) 值分别为3.44%、3.50%、4.24%、4.22%、3.80%, 均小于5.00%。该方法对化合物的检测精度较高。
2.2.4 定量限和检出限
芍药内酯苷和甘草酸的检出限为1 ng·mL-1, 柴胡皂苷A和柴胡皂苷B2为0.5 ng·mL-1, 芍药苷为2 ng·mL-1。表明方法对逍遥丸5种成分的检测灵敏度较高。定量限和检出限的数据见表 2。
2.2.5 回收率
芍药苷在高、中、低浓度下回收率分别为104.44%、102.80%和97.37%, RSD值分别为7.42%、8.10%和5.17%; 芍药内酯苷在高、中、低浓度下回收率分别为109.60%、109.21%和99.46%, RSD值分别为3.85%、4.18%和3.77%; 甘草酸在高、中、低浓度下回收率分别为102.08%、108.88%和101.04%, RSD值分别为5.42%、6.28%和2.43%; 柴胡皂苷A在高、中、低浓度下回收率分别为113.54%、106.23%和103.3%, RSD值分别为3.82%、5.60%和1.70%; 柴胡皂苷B2在高、中、低浓度下回收率分别为107.65%、102.06%和104.69%, RSD值分别为4.17%、1.06%和4.93%, 以上结果表明方法准确度较好。
2.2.6 稳定性
将逍遥丸样品溶液和标准溶液分别置于室温。分别在0、2、6、12、18和24 h测定稳定性, 各化合物的RSD值均低于10%。
3 样品测定
将上述定量研究方法用于5批逍遥丸样品的检测, 结果如表 3所示, 得到3批浓缩丸的芍药苷含量大于4.0 mg·g-1, 2批水丸中的芍药苷含量大于2.5 mg·g-1, 均符合中国药典规定, 但是其他成分的含量存在一定的差异。
讨论
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为能够充分将逍遥丸中的成分提取出来便于准确的定量研究, 考察了不同的甲醇比例的溶剂分别为25%、50%、75%、100%进行超声, 发现甲醇比例增加能够提取出的化合物种类增多, 因此选择100%的甲醇进行超声处理, 同时也考察了用100%甲醇超声时间1、2、3和4 h对5种成分的提取效果, 由HPLC图可以看出2、3和4 h提取的种类和峰面积相当, 但是从LC-MS/MS法定量分析发现3 h后甘草酸的含量比2 h有增加, 从实验节能角度选择超声时间3 h。
从逍遥丸样品检测结果得到所有的样品按现有的质量控制指标都是合格产品, 另外, 发现柴胡皂苷A在浓缩丸中的含量远低于在水丸中的含量, 芍药内酯苷、芍药苷和甘草酸在浓缩丸中的含量高于其在水丸中的含量, 浓缩丸和水丸可能因为制法不同会出现成分含量的差异, 同时也发现来自3个不同厂家的浓缩丸(SX20170209、ZJ170907和JZT201703001) 的甘草酸和柴胡皂苷B2的含量出现明显差异, 两个不同厂家的水丸的柴胡皂苷A、柴胡皂苷B2的一批样品(批号SY10917060114) 明显高于另一批样品(批号KH20161206), 出现成分含量差异的原因, 可能跟中药原药材的质量相关, 也可能与制备丸剂的工艺等因素相关, 比如药材粉碎细度不同, 导致提取效果不同。本研究提示同样是逍遥丸因成分含量不同而导致实际的药效可能不同, 因此中药复方的质量控制研究需要多个成分同时作为质控指标, 本研究可为逍遥丸的质量评价提供依据。
作者贡献: 符洁负责进行实验实施、数据收集、结果分析、撰写、修改文章; 于金波、丛林和赵朕雄参与实验实施; 王琰负责指导整个实验实施以及指导文章的撰写和修改。
利益冲突: 所有作者均声明不存在利益冲突。
基金
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  • 国家自然科学基金(81973290)
  • 国家自然科学基金(82173888)
  • 北京市创新药物非临床药物代谢及药代/药效研究重点实验室(Z141102004414062)
  • 中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-028)
  • 中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-007)
  • 中国医学科学院医学与健康科技创新工程项目(2022-I2M-2-002)
文献
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参考文献 引证文献
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2023年第58卷第1期
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doi: 10.16438/j.0513-4870.2022-0782
  • 接收时间：2022-06-29
  • 首发时间：2025-11-21
  • 出版时间：2023-01-12
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  • 收稿日期：2022-06-29
  • 修回日期：2022-10-29
基金
国家自然科学基金(81973290)
国家自然科学基金(82173888)
北京市创新药物非临床药物代谢及药代/药效研究重点实验室(Z141102004414062)
中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-028)
中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-007)
中国医学科学院医学与健康科技创新工程项目(2022-I2M-2-002)
作者信息
    中国医学科学院药物研究所, 天然药物活性物质与功能国家重点实验室, 北京 100050

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鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
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红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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