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Article(id=1198622902603055932, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198622898320671473, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2022-1007, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1661097600000, receivedDateStr=2022-08-22, revisedDate=1667923200000, revisedDateStr=2022-11-09, acceptedDate=null, acceptedDateStr=null, onlineDate=1763703569317, onlineDateStr=2025-11-21, pubDate=1673452800000, pubDateStr=2023-01-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1763703569317, onlineIssueDateStr=2025-11-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1763703569317, creator=13701087609, updateTime=1763703569317, 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=201, endPage=207, ext={EN=ArticleExt(id=1198622903399973741, articleId=1198622902603055932, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Simultaneous determination of seven components and their distribution in Anoectochilus roxburghii by UHPLC-MS/MS, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Based on ultra high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS), a rapid and simultaneous quantitative method for the measurement of seven components (kinsenoside; rutin; kaempferol-3-O-rutinoside; quercimeritrin; narcissin; isorhamnetin-3-O-glucoside; quercetin) of A. roxburghii was established. The separation was performed over 8.0 minutes on a Waters Acquity UPLC BEH Shield RP18 (2.1 mm×100 mm; 1.7 μm) with a mobile phase consisting of acetonitrile (A) and 0.1% formic acid water solution (B) with gradient elution at a flow rate of 0.2 mL·min-1; the column temperature was 30℃ and the injection volume was 2 μL. Electrospray spray ionization source (ESI source) was used for mass spectrometry, and positive and negative ion modes were detected at the same time. The results showed good linearity (R2 ≥ 0.998 0), with good precision, repeatability and stability, and the average recovery was 97.71%-103.33%. Through cluster heat map and redundancy analysis, we found that kinsenoside was mainly distributed in stems, followed by leaves, and the lowest content in roots. The content of kinsenoside increased significantly in the stems of plants 6 months, but less change was evident in the roots and leaves. Flavonoids and flavonoid glycosides were mainly distributed in leaves. The UHPLC-MS/MS method established in this paper can be used for the quality control of A. roxburghii and provides a reference for establishing a more comprehensive quality detection method for this medicinal.

, authors=null, authorsList=Xin-kai LÜ, Hai-xin DIAO, Li-si ZHOU, Shun-xing GUO, authorCompany=null, correspAuthors=Li-si ZHOU, Shun-xing GUO, 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=1198622904876368869, articleId=1198622902603055932, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=UHPLC-MS/MS同时测定金线兰中7种成分含量及其分布规律研究, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

基于液质联用（UHPLC-MS/MS）技术，建立快速同时定量金线兰[Anoectochilus roxburghii（Wall.）Lindl.]中7种不同极性成分（金线莲苷、水仙苷、槲皮素、芦丁、异鼠李素-3-O-葡萄糖苷、槲皮素-7-O-葡萄糖苷、山柰酚-3-O-芸香糖苷）的方法。采用Waters Acquity UPLC BEH Shield RP18（2.1 mm×100 mm；1.7 μm）色谱柱，以乙腈为流动相A，0.1%甲酸-水溶液为流动相B，0.2 mL·min-1的流速进行梯度洗脱，柱温为30℃，进样量为2 μL，分析时间为8 min。质谱以电喷雾电离源（electron spray ionization，ESI），正、负离子模式同时检测，优化各成分最佳质谱条件。结果发现，7种成分在测定浓度范围内线性关系良好，相关系数均≥ 0.998 0，稳定性、精密度和重复性良好，平均加样回收率为97.71%~103.33%。经聚类热图和RDA（redundancy analysis）分析，发现金线莲苷主要分布在茎中，叶中次之，根中最少。生长6个月的金线兰茎中金线莲苷含量增长显著，而根与叶中增长较少。黄酮及黄酮苷类成分主要分布在叶。本文所建立的液质联用方法准确且灵敏，稳定性与重复性好，可用于金线兰的质量控制，并为建立更全面的金线莲药材质量检测方法提供参考。

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*周丽思, E-mail: ;
郭顺星, E-mail:
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Quim Nova, 2010, 33: 1320-1324., articleTitle=Determination of rutin and narcissin in marigold extract and topical formulations by liquid chromatography: applicability in skin penetration studies, refAbstract=null)], funds=[Fund(id=1198702084569793156, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, awardId=81973426, language=CN, fundingSource=国家自然科学基金资助项目(81973426), fundOrder=null, country=null), Fund(id=1198702085710643851, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, awardId=81903749, language=CN, fundingSource=国家自然科学基金资助项目(81903749), fundOrder=null, country=null), Fund(id=1198702085895193239, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, awardId=2021-I2M-1-031, 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-1-031), fundOrder=null, country=null)], companyList=[AuthorCompany(id=1198702077137486021, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, xref=null, ext=[AuthorCompanyExt(id=1198702077162651847, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, companyId=1198702077137486021, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China), AuthorCompanyExt(id=1198702077175234763, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, companyId=1198702077137486021, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=中国医学科学院、北京协和医学院 药用植物研究所, 北京 100193)])], figs=[ArticleFig(id=1198702082132902404, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=bXADaEhOrKBm6bPa6yJzWw==, figureFileBig=FQvGF6PN7X/HynuwMcrZ7Q==, tableContent=null), ArticleFig(id=1198702082262925831, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Figure 1, caption= Two varieties of <i>A. roxburghii</i> at different cultivation ages. V: Variety. C means tissue culture for 3 months, M for 6 months and D for 9 months , figureFileSmall=bXADaEhOrKBm6bPa6yJzWw==, figureFileBig=FQvGF6PN7X/HynuwMcrZ7Q==, tableContent=null), ArticleFig(id=1198702082439086615, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=cONZcbWYwCQdXQcp8yfDcw==, figureFileBig=AK6yglv1Mbunsm/GJ9YsUQ==, tableContent=null), ArticleFig(id=1198702082573304353, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Figure 2, caption= The representative MRM chromatograms of the seven reference standards (A) and samples of <i>A. roxburghii</i> (B). 1: Kinsenoside; 2: Rutin; 3: Kaempferol-3-<i>O</i>-rutinoside; 4: Quercimeritrin; 5: Narcissin; 6: Isorhamnetin-3-<i>O</i>-glucoside; 7: Quercetin , figureFileSmall=cONZcbWYwCQdXQcp8yfDcw==, figureFileBig=AK6yglv1Mbunsm/GJ9YsUQ==, tableContent=null), ArticleFig(id=1198702082715910697, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=ZO9AWDyGysVdDTA7f0HyQA==, figureFileBig=HDClVGEx6B3K3SSDc8u6dw==, tableContent=null), ArticleFig(id=1198702082808185388, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Figure 3, caption= Cluster heat map analysis of 7 components in roots, stems and leaves of two varieties of <i>A. roxburghii</i> at different cultivation ages , figureFileSmall=ZO9AWDyGysVdDTA7f0HyQA==, figureFileBig=HDClVGEx6B3K3SSDc8u6dw==, tableContent=null), ArticleFig(id=1198702082908848693, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=+S6xQsdbqAcc4gKU4/E8Cg==, figureFileBig=ohMG4R+vFxWNSd+XWhxYlQ==, tableContent=null), ArticleFig(id=1198702083022094907, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Figure 4, caption= Redundancy analysis of 7 components in roots, stems and leaves of two varieties of <i>A. roxburghii</i> at different cultivation ages , figureFileSmall=+S6xQsdbqAcc4gKU4/E8Cg==, figureFileBig=ohMG4R+vFxWNSd+XWhxYlQ==, tableContent=null), ArticleFig(id=1198702083298918985, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Sample No. Tissue culture age Variety
Variety 1-C 3 months 1
Variety 1-M 6 months 1
Variety 1-D 9 months 1
Variety 2-C 3 months 2
Variety 2-M 6 months 2
Variety 2-D 9 months 2
), ArticleFig(id=1198702083466691146, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Table 1, caption=

Original information of A. roxburghii

, figureFileSmall=null, figureFileBig=null, tableContent=
Sample No. Tissue culture age Variety
Variety 1-C 3 months 1
Variety 1-M 6 months 1
Variety 1-D 9 months 1
Variety 2-C 3 months 2
Variety 2-M 6 months 2
Variety 2-D 9 months 2
), ArticleFig(id=1198702083588325971, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Compound Ionization mode m/z DP/V EP/V CE/V CXP/V Ion
Parent ion Daughter ion
Kinsenoside ESI+ 264.9 103.1 33 10 14 15 QuanI
264.9 167.0 52 10 9 15 QualI
264.9 145.0 12 10 13 15 QualI
Narcissin ESI+ 625.1 316.9 171 10 25 15 QuanI
625.1 479.0 171 10 17 15 QualI
Rutin ESI- 608.7 300.1 -286 -10 -44 -15 QuanI
608.7 151.1 -286 -10 -54 -15 QualI
Quercetin ESI- 300.5 150.8 -129 -10 -28 -15 QuanI
300.5 178.9 -112 -10 -24 -15 QualI
Quercimeritrin ESI- 462.9 300.9 -284 -10 -35 -15 QuanI
462.9 151.1 -294 -10 -32 -15 QualI
Isorhamnetin-3-O-glucoside ESI- 477.0 313.9 -297 -10 -37 -15 QuanI
477.0 271.0 -294 -10 -38 -15 QualI
Kaempferol-3-O-rutinoside ESI- 593.1 284.8 -200 -10 -42 -15 QuanI
593.1 254.8 -205 -10 -65 -15 QualI
), ArticleFig(id=1198702083739320922, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Table 2, caption=

Parameters of MS analysis of 7 components in A. roxburghii. ESI: Electrospray ionization; DP: Declustering potential; EP: Entrance potential; CE: Collision energy; CXP: Collision cell exit potential; QuanI: Quantitative ion; QualI: Qualitative ion

, figureFileSmall=null, figureFileBig=null, tableContent=
Compound Ionization mode m/z DP/V EP/V CE/V CXP/V Ion
Parent ion Daughter ion
Kinsenoside ESI+ 264.9 103.1 33 10 14 15 QuanI
264.9 167.0 52 10 9 15 QualI
264.9 145.0 12 10 13 15 QualI
Narcissin ESI+ 625.1 316.9 171 10 25 15 QuanI
625.1 479.0 171 10 17 15 QualI
Rutin ESI- 608.7 300.1 -286 -10 -44 -15 QuanI
608.7 151.1 -286 -10 -54 -15 QualI
Quercetin ESI- 300.5 150.8 -129 -10 -28 -15 QuanI
300.5 178.9 -112 -10 -24 -15 QualI
Quercimeritrin ESI- 462.9 300.9 -284 -10 -35 -15 QuanI
462.9 151.1 -294 -10 -32 -15 QualI
Isorhamnetin-3-O-glucoside ESI- 477.0 313.9 -297 -10 -37 -15 QuanI
477.0 271.0 -294 -10 -38 -15 QualI
Kaempferol-3-O-rutinoside ESI- 593.1 284.8 -200 -10 -42 -15 QuanI
593.1 254.8 -205 -10 -65 -15 QualI
), ArticleFig(id=1198702083907093087, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Compound LOD/ng·mL-1 LOQ/ng·mL-1 Regressive equation R2 Linear range/ng·mL-1
Kinsenoside 70.83 212.50 Y = 134.97 X + 1 104.70 0.999 9 212.50-8 500.00
Narcissin 4.28 8.55 Y = 1 831.60 X + 8 658.60 0.998 9 8.55-173.75
Quercetin 1.86 7.42 Y = 792.78 X - 1 698.10 0.999 2 7.42-475.00
Rutin 35.47 70.94 Y = 116.43 X - 517.20 0.999 7 70.94-2 837.50
Quercimeritrin 3.16 6.33 Y = 498.19 X + 2 480.60 0.998 9 6.32-1 012.50
Isorhamnetin-3-O-glucoside 7.51 15.02 Y = 34.12 X + 573.54 0.998 0 30.04-961.25
Kaempferol-3-O-rutinoside 4.65 9.30 Y = 1 262.70 X + 14 373.00 0.999 8 9.30-1 487.50
), ArticleFig(id=1198702084104225382, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Table 3, caption=

Limit of detection (LOD), limit of quantitation (LOQ), regressive equations, correlation coefficients and linear ranges of 7 components

, figureFileSmall=null, figureFileBig=null, tableContent=
Compound LOD/ng·mL-1 LOQ/ng·mL-1 Regressive equation R2 Linear range/ng·mL-1
Kinsenoside 70.83 212.50 Y = 134.97 X + 1 104.70 0.999 9 212.50-8 500.00
Narcissin 4.28 8.55 Y = 1 831.60 X + 8 658.60 0.998 9 8.55-173.75
Quercetin 1.86 7.42 Y = 792.78 X - 1 698.10 0.999 2 7.42-475.00
Rutin 35.47 70.94 Y = 116.43 X - 517.20 0.999 7 70.94-2 837.50
Quercimeritrin 3.16 6.33 Y = 498.19 X + 2 480.60 0.998 9 6.32-1 012.50
Isorhamnetin-3-O-glucoside 7.51 15.02 Y = 34.12 X + 573.54 0.998 0 30.04-961.25
Kaempferol-3-O-rutinoside 4.65 9.30 Y = 1 262.70 X + 14 373.00 0.999 8 9.30-1 487.50
), ArticleFig(id=1198702084200694381, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
Sample No. Kinsenoside /mg·g-1 Narcissin /μg·g-1 Quercetin /μg·g-1 Quercimeritrin /μg·g-1 Isorhamnetin-3-O- glucoside/μg·g-1 Kaempferol-3-O- rutinoside/μg·g-1 Rutin /μg·g-1
V1-C-R 28.78 ± 1.1 1.7 ± 1.15 - - - - -
V1-C-S 47.59 ± 2.15 2.25 ± 0.06 - - 10.61 ± 1.77 1.63 ± 0.1 -
V1-C-L 38.51 ± 1.37 13.8 ± 2.15 5.31 ± 0.67 35.61 ± 1.68 113.47 ± 8.5 20.06 ± 0.93 11.19 ± 1.64
V1-M-R 17.27 ± 2.76 12.91 ± 0.44 - - - - -
V1-M-S 145.88 ± 6.62 436.78 ± 6.7 - - 28.44 ± 4.68 2.83 ± 0.3 -
V1-M-L 39.62 ± 2.64 145.14 ± 3.42 6.72 ± 0.84 40.13 ± 2.92 96.15 ± 1.11 12.48 ± 0.22 23.12 ± 1.61
V1-D-R 31.53 ± 1.61 21.27 ± 2.29 - - - - -
V1-D-S 60.2 ± 1.29 196.1 ± 2.72 - - 5.34 ± 2.47 0.91 ± 0.05 -
V1-D-L 56.16 ± 1.16 1 401.71 ± 27.06 - 36.44 ± 1.78 78.94 ± 13.6 11.82 ± 0.6 22.12 ± 0.97
V2-C-R 23.42 ± 1.85 7.08 ± 0.51 - - - - -
V2-C-S 74.78 ± 4.81 122.14 ± 9.56 - - 19.64 ± 1.84 2.49 ± 0.11 -
V2-C-L 47.89 ± 3.25 1 187.56 ± 27.82 11.79 ± 0.27 41.28 ± 2.88 268 ± 28.47 25.84 ± 1.22 35.16 ± 10.95
V2-M-R 44.72 ± 6.46 9.75 ± 0.73 - - - - -
V2-M-S 176.42 ± 12.23 203.05 ± 22.27 - - 25.89 ± 5.61 2.48 ± 0.12 -
V2-M-L 55.16 ± 2.94 958.65 ± 3.51 3.53 ± 0.18 54.88 ± 3.58 111.6 ± 15.6 16.43 ± 1.01 18.18 ± 2.86
V2-D-R 26.42 ± 0.63 15.85 ± 0.62 - - - - -
V2-D-S 74.88 ± 5.27 234.45 ± 0.32 - - 8.02 ± 1.34 1.96 ± 0.06 -
V2-D-L 56.89 ± 0.43 1 115.58 ± 8.51 2.13 ± 0.28 66.83 ± 3.2 126.28 ± 4.88 15.44 ± 0.57 12.84 ± 1.75
), ArticleFig(id=1198702084330717816, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198622902603055932, language=CN, label=Table 4, caption=

The contents of 7 components in roots (R), stems (S) and leaves (L) of two varieties of A. roxburghii at different cultivation ages. - means lower than LOQ

, figureFileSmall=null, figureFileBig=null, tableContent=
Sample No. Kinsenoside /mg·g-1 Narcissin /μg·g-1 Quercetin /μg·g-1 Quercimeritrin /μg·g-1 Isorhamnetin-3-O- glucoside/μg·g-1 Kaempferol-3-O- rutinoside/μg·g-1 Rutin /μg·g-1
V1-C-R 28.78 ± 1.1 1.7 ± 1.15 - - - - -
V1-C-S 47.59 ± 2.15 2.25 ± 0.06 - - 10.61 ± 1.77 1.63 ± 0.1 -
V1-C-L 38.51 ± 1.37 13.8 ± 2.15 5.31 ± 0.67 35.61 ± 1.68 113.47 ± 8.5 20.06 ± 0.93 11.19 ± 1.64
V1-M-R 17.27 ± 2.76 12.91 ± 0.44 - - - - -
V1-M-S 145.88 ± 6.62 436.78 ± 6.7 - - 28.44 ± 4.68 2.83 ± 0.3 -
V1-M-L 39.62 ± 2.64 145.14 ± 3.42 6.72 ± 0.84 40.13 ± 2.92 96.15 ± 1.11 12.48 ± 0.22 23.12 ± 1.61
V1-D-R 31.53 ± 1.61 21.27 ± 2.29 - - - - -
V1-D-S 60.2 ± 1.29 196.1 ± 2.72 - - 5.34 ± 2.47 0.91 ± 0.05 -
V1-D-L 56.16 ± 1.16 1 401.71 ± 27.06 - 36.44 ± 1.78 78.94 ± 13.6 11.82 ± 0.6 22.12 ± 0.97
V2-C-R 23.42 ± 1.85 7.08 ± 0.51 - - - - -
V2-C-S 74.78 ± 4.81 122.14 ± 9.56 - - 19.64 ± 1.84 2.49 ± 0.11 -
V2-C-L 47.89 ± 3.25 1 187.56 ± 27.82 11.79 ± 0.27 41.28 ± 2.88 268 ± 28.47 25.84 ± 1.22 35.16 ± 10.95
V2-M-R 44.72 ± 6.46 9.75 ± 0.73 - - - - -
V2-M-S 176.42 ± 12.23 203.05 ± 22.27 - - 25.89 ± 5.61 2.48 ± 0.12 -
V2-M-L 55.16 ± 2.94 958.65 ± 3.51 3.53 ± 0.18 54.88 ± 3.58 111.6 ± 15.6 16.43 ± 1.01 18.18 ± 2.86
V2-D-R 26.42 ± 0.63 15.85 ± 0.62 - - - - -
V2-D-S 74.88 ± 5.27 234.45 ± 0.32 - - 8.02 ± 1.34 1.96 ± 0.06 -
V2-D-L 56.89 ± 0.43 1 115.58 ± 8.51 2.13 ± 0.28 66.83 ± 3.2 126.28 ± 4.88 15.44 ± 0.57 12.84 ± 1.75
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UHPLC-MS/MS同时测定金线兰中7种成分含量及其分布规律研究
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吕欣锴 , 刁海欣 , 周丽思 * , 郭顺星 *
药学学报 | 研究论文 2023,58(1): 201-207
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药学学报 |研究论文 2023 , 58 (1) : 201 -207
UHPLC-MS/MS同时测定金线兰中7种成分含量及其分布规律研究
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吕欣锴, 刁海欣, 周丽思* , 郭顺星*
作者信息
  • 中国医学科学院、北京协和医学院 药用植物研究所, 北京 100193
通讯作者:
*周丽思, E-mail: ;
郭顺星, E-mail:
Simultaneous determination of seven components and their distribution in Anoectochilus roxburghii by UHPLC-MS/MS
Xin-kai LÜ, Hai-xin DIAO, Li-si ZHOU* , Shun-xing GUO*
Affiliations
  • Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China
出版时间: 2023-01-12 doi: 10.16438/j.0513-4870.2022-1007
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摘要
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基于液质联用（UHPLC-MS/MS）技术，建立快速同时定量金线兰[Anoectochilus roxburghii（Wall.）Lindl.]中7种不同极性成分（金线莲苷、水仙苷、槲皮素、芦丁、异鼠李素-3-O-葡萄糖苷、槲皮素-7-O-葡萄糖苷、山柰酚-3-O-芸香糖苷）的方法。采用Waters Acquity UPLC BEH Shield RP18（2.1 mm×100 mm；1.7 μm）色谱柱，以乙腈为流动相A，0.1%甲酸-水溶液为流动相B，0.2 mL·min-1的流速进行梯度洗脱，柱温为30℃，进样量为2 μL，分析时间为8 min。质谱以电喷雾电离源（electron spray ionization，ESI），正、负离子模式同时检测，优化各成分最佳质谱条件。结果发现，7种成分在测定浓度范围内线性关系良好，相关系数均≥ 0.998 0，稳定性、精密度和重复性良好，平均加样回收率为97.71%~103.33%。经聚类热图和RDA（redundancy analysis）分析，发现金线莲苷主要分布在茎中，叶中次之，根中最少。生长6个月的金线兰茎中金线莲苷含量增长显著，而根与叶中增长较少。黄酮及黄酮苷类成分主要分布在叶。本文所建立的液质联用方法准确且灵敏，稳定性与重复性好，可用于金线兰的质量控制，并为建立更全面的金线莲药材质量检测方法提供参考。

金线兰  /  开唇兰属  /  金线莲苷  /  UHPLC-MS/MS  /  含量测定  /  分布规律

Based on ultra high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS), a rapid and simultaneous quantitative method for the measurement of seven components (kinsenoside; rutin; kaempferol-3-O-rutinoside; quercimeritrin; narcissin; isorhamnetin-3-O-glucoside; quercetin) of A. roxburghii was established. The separation was performed over 8.0 minutes on a Waters Acquity UPLC BEH Shield RP18 (2.1 mm×100 mm; 1.7 μm) with a mobile phase consisting of acetonitrile (A) and 0.1% formic acid water solution (B) with gradient elution at a flow rate of 0.2 mL·min-1; the column temperature was 30℃ and the injection volume was 2 μL. Electrospray spray ionization source (ESI source) was used for mass spectrometry, and positive and negative ion modes were detected at the same time. The results showed good linearity (R2 ≥ 0.998 0), with good precision, repeatability and stability, and the average recovery was 97.71%-103.33%. Through cluster heat map and redundancy analysis, we found that kinsenoside was mainly distributed in stems, followed by leaves, and the lowest content in roots. The content of kinsenoside increased significantly in the stems of plants 6 months, but less change was evident in the roots and leaves. Flavonoids and flavonoid glycosides were mainly distributed in leaves. The UHPLC-MS/MS method established in this paper can be used for the quality control of A. roxburghii and provides a reference for establishing a more comprehensive quality detection method for this medicinal.

Anoectochilus roxburghii  /  Anoectochilus  /  kinsenoside  /  UHPLC-MS/MS  /  content determination  /  distribution
吕欣锴, 刁海欣, 周丽思, 郭顺星. UHPLC-MS/MS同时测定金线兰中7种成分含量及其分布规律研究. 药学学报, 2023 , 58 (1) : 201 -207 . DOI: 10.16438/j.0513-4870.2022-1007
Xin-kai LÜ, Hai-xin DIAO, Li-si ZHOU, Shun-xing GUO. Simultaneous determination of seven components and their distribution in Anoectochilus roxburghii by UHPLC-MS/MS[J]. Acta Pharmaceutica Sinica, 2023 , 58 (1) : 201 -207 . DOI: 10.16438/j.0513-4870.2022-1007
正文
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金线兰[Anoectochilus roxburghii (Wall.) Lindl.], 又名花叶开唇兰, 是兰科开唇兰属药用植物, 全草入药, 具有降血脂、降血糖、抗炎、保肝等功效[1, 2]。作为药材“金线莲”的基源植物之一, 其分布和组培量远高于另一基源植物台湾银线兰(Anoectochilus formosanus Hayata)。金线兰主要分布在我国的福建省、浙江省、广东省、贵州省等南部省份。因其具有生长时期长、繁殖率低、环境要求严格等特点, 野生金线兰资源稀缺, 被《濒危野生动植物种国际贸易公约》(CITES) 列为附录Ⅱ的保护物种, 被《国家重点保护野生植物名录》(第二批) 列为二级保护植物[3]。目前市场主要流通的金线兰是应用组织培养技术规模化生产的无性繁殖组培苗[4]。
金线兰中化学成分众多, 主要包括金线莲苷、黄酮及黄酮苷类、有机酸类、三萜及甾体类等[5]。其中金线莲苷作为含量最高的成分, 具有良好的降血糖[6]、肝脏保护活性[7], 被广泛认为是金线兰最具代表的活性成分[8]。此外, 金线兰中黄酮及黄酮苷类丰富, 主要包括异鼠李素、槲皮素、芦丁等, 发挥抗炎及抗氧化应激等功效[9-11]。传统检测金线莲苷和黄酮类成分多采用高效液相色谱仪。紫外检测器可检测黄酮类成分, 但由于金线莲苷无紫外吸收, 因此一般采用蒸发光散射检测器检测[12, 13]。因此, 若同时检测这两大类成分, 使用液质联用技术更方便、快捷、灵敏度更高。
不同次生代谢产物在药用植物中分布存在一定规律。金线兰为全草入药, 但对其中活性成分的组织分布及随生长时间变化规律研究较少。本研究通过测定金线兰不同组织、不同生长时期的活性成分含量, 旨在阐明金线兰中金线莲苷及黄酮类活性成分在不同组织结构中分布规律以及不同生长时期积累及变化特征, 为金线兰的质量控制提供依据。
材料与方法
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仪器  岛津LC-20A型超高效液相色谱仪(日本岛津公司, 包括DGU-30A3型在线真空脱气机, LC-20AD型二元泵, SIL-20AC型自动进样器, CTO-20A型柱温箱); 5500 QTRAP三重四极杆线性离子阱质谱仪(配备电喷雾电离源) 和Analyst数据分析软件(美国AB SCIEX公司); LGJ-18真空冷冻干燥机(北京松源华兴科技发展有限公司); MM400冷冻研磨仪(德国Retsch公司); KQ-700DE超声仪(昆山市超声仪器有限公司)。
试剂  金线莲苷(批号DJ005301, 纯度≥ 98%)、水仙苷(批号BWB50839, 纯度≥ 98%)、槲皮素(批号BWB50375, 纯度≥ 98%)、芦丁(批号BWB51607, 纯度≥ 98%)、异鼠李素-3-O-葡萄糖苷(批号BWB50966, 纯度≥ 98%)、槲皮素-7-O-葡萄糖苷(批号BWB51675, 纯度≥ 98%) 均购于北京世纪奥科生物技术有限公司, 山柰酚-3-O-芸香糖苷(批号AF8112493, 纯度≥ 98%)购于成都埃法生物科技有限公司; 乙腈、甲醇均为色谱级(美国Thermo Fisher Scientific公司); 超纯水(美国Watsons公司); 甲酸为分析级(北京化工厂)。
样品信息  金线兰样品信息见表 1, 不同时期金线兰样品见图 1。经北京协和医学院药用植物研究所郭顺星研究员鉴定, 均为金线兰。
色谱条件  色谱柱: Waters Acquity UPLC BEH Shield RP18 (100 mm × 2.1 mm; 1.7 μm, 美国Waters公司); 流速0.2 mL·min-1; 柱温30 ℃, 进样量2 μL。流动相A为乙腈, B为0.1%甲酸-水溶液, 梯度洗脱(0~2 min, 5%~10% A; 2~2.5 min, 10%~45% A; 2.5~5.5 min, 45%~95% A; 5.5~6 min, 95% A; 6~7 min, 95%~5% A; 7~8 min, 5% A)。
质谱条件  离子源为电喷雾电离源(ESI); 扫描方式为多重反应监测(multiple reaction monitoring, MRM), 正离子模式(ESI+) 与负离子模式(ESI-) 监测; 喷雾气与干燥气均为氮气; 帘气(curtain gas, CUR) 为25 psi; 源温度为550 ℃, 源喷射电压为+5 500/-4 500 V, 喷雾气(GS1, N2) 为55 psi, 辅助气(GS2, N2) 为55 psi。待测化合物的定量离子对(quantitative ion; QuanI)、定性离子对(qualitative ion; QualI)、去簇电压(declustering potential, DP)、入口电压(entrance potential, EP)、碰撞能量(collision energy, CE)、碰撞室出口电压(collision cell exit potential, CXP), 见表 2。
对照品溶液的制备  精密称取7种对照品适量, 甲醇定容, 超声溶解后摇匀, 配制成单一对照品储备液。分别吸取适量单一对照品储备液, 甲醇定容, 摇匀, 即得混合对照品溶液, 其中金线莲苷、水仙苷、槲皮素、芦丁、异鼠李素-3-O-葡萄糖苷、槲皮素-7-O-葡萄糖苷和山柰酚-3-O-芸香糖苷质量浓度分别为8.50、10.95、9.50、11.35、19.23、8.10和11.90 μg·mL-1。
样品制备  将金线兰样品的根、茎、叶分开, 保存于-80 ℃, 采用真空冷冻干燥机将其干燥。在冷冻研磨仪中粉碎15~90 s, 功率为25~30 W。精密称取样品20 mg, 用3 mL甲醇浸泡12 h, 再用3 mL甲醇、70%甲醇、水, 分别超声提取一次, 每次超声15 min, 5 000 r·min-1离心10 min。合并提取液, 用甲醇定容至10 mL, 即得供试液。每个样品平行提取3次, 平行进样2针。
方法学考察
专属性  分别精密吸取混合对照品溶液和供试品溶液各1 μL, 按上述液质联用条件进样分析, 利用GraphPad软件, 将各化合物MRM色谱图汇总, 得到混合对照品与供试品溶液MRM色谱图, 比较混合对照品溶液和供试品溶液的色谱图与保留时间。
线性关系与定量范围考察  用甲醇将混合对照品储备液梯度稀释至适宜倍数, 经0.22 μm微孔滤膜, 按上述液质联用条件进样分析。以峰面积为纵坐标, 浓度为横坐标, 进行线性回归分析。将混合对照品溶液不断稀释, 直至信噪比为3, 以此作为检测限(limit of detection, LOD), 同理, 以信噪比为10时作为定量限(limit of quantitation, LOQ)。
稳定性  按上述样品制备方法制备供试品溶液, 分别于室温放置0、2、4、8、12、24、36和48 h时, 按上述液质联用条件进样分析, 记录峰面积并计算RSD值。
精密度  选取稀释40倍的混标稀释液, 按上述液质联用条件连续进样6次, 记录峰面积并计算RSD值。
重复性  按上述样品制备方法制备6份供试品溶液, 按上述液质联用条件进样分析, 记录峰面积并计算RSD值。
加样回收率  精密称取已知含量的金线兰V1-M-L样品9份, 每份取20 mg, 按每3份为一组, 每组精密加入对照品金线莲苷、水仙苷、槲皮素、芦丁、异鼠李素- 3-O-葡萄糖苷、槲皮素-7-O-葡萄糖苷、山柰酚-3-O-芸香糖苷的量相当于金线兰样品中各对照品含量的50%、100%、150%, 按“样品制备”项下方法制备供试品溶液, 精密吸取各供试品溶液1 μL, 按上述液质联用条件进样分析, 记录峰面积, 计算平均加样回收率和RSD值。
金线兰中7种化合物分布规律研究
含量测定  按照上述样品制备方法, 分别制备出V1-C、V1-M、V1-D、V2-C、V2-M和V2-D的根、茎和叶共18个样品的提取液, 根据对照品线性范围将提取液稀释至适宜浓度, 用0.22 μm微孔滤膜过滤后, 按上述液质联用条件进样分析。
聚类热图分析  采用Z-Score法将7种化合物的含量数据标准化, 从而将不同量级的含量数据转化成统一量度[14]。使用OmicStudio平台构建聚类热图, 采用层次聚类法, 使用欧式距离计算不同类别数据点间的距离。
RDA分析  采用Z-Score法将7种化合物的含量数据标准化, 以生长时间(3、6、9个月)、品种(V1与V2)、组织(根、茎、叶) 作为三种环境因子。利用Tutools平台进行RDA分析, 评估金线兰中7种成分含量与三种环境因子之间的关联性。
结果
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1 方法学考察
1.1 专属性考察
混合对照品与供试品溶液MRM色谱图见图 2。被测成分峰形良好, 无其他干扰, 供试品溶液中7种待测成分保留时间与混合对照品基本相同, 表明该方法专属性良好。
1.2 线性关系与定量范围考察
7种成分的检测限和定量限结果见表 3; 以峰面积为纵坐标, 浓度为横坐标, 进行线性回归分析, 结果见表 3。
1.3 稳定性
48 h内供试品溶液金线莲苷、水仙苷、槲皮素、芦丁、槲皮素-7-O-葡萄糖苷、异鼠李素-3-O-葡萄糖苷和山柰酚-3-O-芸香糖苷的峰面积RSD分别为1.82%、3.82%、2.31%、2.90%、2.38%、4.25%和4.31%, 表明供试品溶液在48 h内稳定性良好。
1.4 精密度
6次连续进样的对照品溶液中金线莲苷、水仙苷、槲皮素、芦丁、槲皮素-7-O-葡萄糖苷、异鼠李素-3-O-葡萄糖苷和山柰酚-3-O-芸香糖苷的峰面积RSD分别为3.21%、1.30%、3.19%、1.57%、2.85%、1.98%和2.86%, 表明仪器精密度良好。
1.5 重复性
6份同一方法制备的供试品溶液中金线莲苷、水仙苷、槲皮素、芦丁、槲皮素-7-O-葡萄糖苷、异鼠李素-3-O-葡萄糖苷和山柰酚-3-O-芸香糖苷的峰面积RSD分别为3.42%、1.79%、3.54%、2.54%、2.86%、3.06%和3.17%, 表明该方法重复性良好。
1.6 加样回收率
金线莲苷、水仙苷、槲皮素、芦丁、槲皮素-7-O-葡萄糖苷、异鼠李素-3-O-葡萄糖苷和山柰酚-3-O-芸香糖苷平均加样回收率分别为97.71%、100.73%、99.81%、101.54%、103.33%、101.19%和99.57%。RSD分别为2.82%、2.68%、1.13%、4.20%、2.97%、2.09%和3.08%, 表明该方法准确度良好。
2 金线兰中7种化合物分布规律研究
2.1 样品含量测定
18份样品中金线莲苷、水仙苷、槲皮素、芦丁、槲皮素-7-O-葡萄糖苷、异鼠李素-3-O-葡萄糖苷和山柰酚-3-O-芸香糖苷的含量见表 4。
2.2 聚类热图分析
聚类热图分析结果见图 3。当含量大于平均值时, 标准化后为正数, 否则为负数。由横坐标聚类分析, 发现金线莲苷与其余的6种黄酮及黄酮苷类成分可显著区分。金线莲苷主要分布在茎中, 叶次之, 根中最少。此外, 无论品种1还是品种2, 均在M期(6个月) 金线莲苷的含量达到顶峰。由纵坐标聚类分析, 发现两个品种金线兰的叶均可聚为一类, 主要由于6种黄酮及黄酮苷几乎全部分布在叶中。
2.3 RDA分析
RDA分析结果见图 4。坐标轴代表不同的环境因子, 长度越长表示该环境因子影响越大; 坐标轴之间的夹角为锐角时表示两个环境因子之间呈正相关, 钝角时呈负相关[15, 16]。根据RDA分析可知, 7种成分含量与其组织分布最为相关, 而品种对其影响最小。在单一成分分析中, 发现取样组织部位不同与金线莲苷含量差异最相关; 水仙苷含量则受生长时间影响最大; 异鼠李素-3-O-葡萄糖苷、槲皮素-7-O-葡萄糖苷含量则受品种差异影响较大; 而其余成分与各环境因子相关性无明显规律。此外, 三种环境因子间无显著相关。
讨论
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金线莲苷为金线兰的主要活性成分, 高温时不稳定, 因此本样品采用冷冻干燥法低温研磨。有研究[17]证实, 使用该方法处理后药材的金线莲苷含量可比烘干法高30%以上。因其高极性, 一般采用水提法提取金线莲苷, 提取率可达乙醇提取的两倍。本研究同时考虑对黄酮及黄酮苷类化合物的提取效率, 因此采用甲醇、70%甲醇、水, 三种不同极性溶剂分别进行提取然后合并, 同时扩大提取溶剂体积(每次150倍), 以保证充分提取。
金线莲苷仅有紫外末端吸收, 常规配备紫外检测器的液相色谱很难对其进行检测。目前主要采用蒸发光散射检测器进行检测。但蒸发光散射检测器灵敏度较低、易受环境影响, 并且线性范围较窄, 多成分检测受一定限制[18]。因此本研究采用液质联用进行多成分检测, 并对7个化合物各质谱参数进行优化。首先在正离子或负离子模式下, 针泵连续进样, 手动调谐模式下找到母离子和子离子。随后在MRM模式下, 优化离子对参数, 包括DP、EP、CE、CXP值, 得到每个化合物的最优电离参数, 以保证峰形较好、响应较高。该方法可同时检测金线兰中7种主要化合物, 对于色谱柱未完全分离、极性相似的黄酮及黄酮苷类也可依据其特征离子进行定量, 增加检测准确性、稳定性与灵敏度的同时, 还可极大提高检测效率。
金线兰暂未被收录入《中华人民共和国药典》, 2013年发行的《地理标志产品永安金线莲》 (DB35/T 1388-2013) 将总多糖和总黄酮含量作为金线兰质量控制指标, 但缺乏对其特征性有效成分金线莲苷含量的考察。2022年实施的《福建省食品安全地方标准金线莲》 (DBS35/006-2022) 则将金线莲苷作为质量评价指标, 要求每100 g金线兰干品中金线莲苷含量≥ 10 g。根据本研究含量测定结果, 发现两个品种仅生长6个月的金线兰茎可满足要求。提示若超过6个月继续培养, 应考虑关键营养元素的补充。此外, 金线兰中水仙苷的含量最高可达1 mg·g-1, 显著高于其他黄酮和黄酮苷。水仙苷具有良好的抗氧化活性[19], 可考虑将其作为金线兰质量评价参考指标之一。
作为名贵的药用植物, 金线兰野生资源稀缺, 目前市场中主要为人工无性繁殖组培品。本研究选取了市面上常见的两个无性繁殖品种进行7种成分分布规律研究。根据实验结果, 发现两个品种各成分含量差异较小, 含量随组织与时间分布规律趋于一致。通过分析其组织分布, 发现金线莲苷主要分布在茎中, 叶中次之, 根中最少。两个品种生长6个月的金线兰茎中金线莲苷含量增长显著, 分别相当于生长3个月的2.3和3倍, 而根与叶的含量变化较小。
综上所述, 本研究所建立的同时测定金线兰中7种成分含量的UHPLC-MS/MS方法专属性强, 重复性良好, 检测灵敏度高, 检测时间短, 可为金线兰的质量控制提供依据, 也为其成药研究提供借鉴。同时, 分析了7种成分在金线兰不同组织部位、培养时间、品种的分布规律, 为优化金线兰人工培育与采收提供参考。
作者贡献: 吕欣锴负责实验及文章撰写; 刁海欣负责实验; 周丽思负责实验材料收集、文章选题、修改文章; 郭顺星指导实验方法、负责文章选题、审阅文章。
利益冲突: 无任何利益冲突。
基金
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  • 国家自然科学基金资助项目(81973426)
  • 国家自然科学基金资助项目(81903749)
  • 中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-031)
文献
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2023年第58卷第1期
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doi: 10.16438/j.0513-4870.2022-1007
  • 接收时间：2022-08-22
  • 首发时间：2025-11-21
  • 出版时间：2023-01-12
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  • 收稿日期：2022-08-22
  • 修回日期：2022-11-09
基金
国家自然科学基金资助项目(81973426)
国家自然科学基金资助项目(81903749)
中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-031)
作者信息
    中国医学科学院、北京协和医学院 药用植物研究所, 北京 100193

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*周丽思, E-mail: ;
郭顺星, E-mail:
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2种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
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
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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