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Article(id=1153433638973726792, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153433633999282214, articleNumber=null, orderNo=null, doi=10.19812/j.cnki.jfsq11-5956/ts.20241213003, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1734019200000, receivedDateStr=2024-12-13, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1752929609291, onlineDateStr=2025-07-19, pubDate=1742832000000, pubDateStr=2025-03-25, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1752929609291, onlineIssueDateStr=2025-07-19, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1752929609291, creator=13701087609, updateTime=1752929609291, updator=13701087609, issue=Issue{id=1153433633999282214, tenantId=1146029695717560320, journalId=1149652044408987649, year='2025', volume='16', issue='6', pageStart='1', pageEnd='322', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=0, createTime=1752929608105, creator=13701087609, updateTime=1758086445549, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1175062977960096080, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153433633999282214, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1175062977960096081, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153433633999282214, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=275, endPage=283, ext={EN=ArticleExt(id=1153433641016352896, articleId=1153433638973726792, tenantId=1146029695717560320, journalId=1149652044408987649, language=EN, title=Metabolite composition analysis of leaves and stems of Platycodon grandiflorus based on ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry, columnId=1151895321388347923, journalTitle=Journal of Food Safety & Quality, columnName=Food Analysis and Detection, runingTitle=null, highlight=null, articleAbstract=

Objective To analyse the types and content of metabolites in the stems and leaves of Platycodon grandiflorus by ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry (UPLC-Q/Orbitrap HRMS). Methods Stems and leaves of two-year-old purple flowered Platycodon grandiflorus from different sources was used as experimental materials. UPLC-Q/Orbitrap HRMS technology was used to analyze the extracts of Platycodon grandiflorus stems and leaves in negative ion mode, using orbitrap for MS1 full scan and data dependent acquisition ion trap for MS2 scan, and screen for differential metabolites of Platycodon grandiflorum stems and leaves from different sources. Results A total of 18 metabolites were detected in the stems and leaves of Platycodon grandiflorum, including 4 flavonoids, 2 alkynyl glycosides, and 12 saponins (1 metabolite that had not been reported). The basic structure of this unknown compound was polygalacic acid-glucose- xylose/arabic glycoside. Through comparative analysis, differences in chemical composition of Platycodon grandiflorus among different sources were discovered. The 6 differential metabolites of Platycodon grandiflorus from China and South Korea and 1 differential metabolite of Platycodon grandiflorus from Yanbian area were screened. Conclusion The comprehensive analysis results indicate that the stems and leaves of Platycodon grandiflorus have rich chemical components, and the stems and leaves of Platycodon grandiflorus from different sources have compound differences, which have high development and utilization prospects, providing theoretical basis for the development and utilization of aboveground resources of Platycodon grandiflorus.

, correspAuthors=Xiang-Min PIAO, Chun-Mei LIN, authorNote=null, correspAuthorsNote=null, copyrightStatement=null, 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, authorCompany=null, fund=null, authors=null, authorsList=Chang-An BI, Jun-Mei LIAN, Yan YAN, Xiang-Min PIAO, Chun-Mei LIN), CN=ArticleExt(id=1153433663317468001, articleId=1153433638973726792, tenantId=1146029695717560320, journalId=1149652044408987649, language=CN, title=基于超高效液相色谱-串联四极杆/轨道阱高分辨质谱法分析桔梗茎叶代谢物, columnId=1151895321958773274, journalTitle=食品安全质量检测学报, columnName=食品分析与检测, runingTitle=null, highlight=null, articleAbstract=

目的 基于超高效液相色谱-串联四极杆/轨道阱高分辨质谱法(ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry, UPLC-Q/Orbitrap HRMS)分析桔梗茎叶中代谢物的种类和含量。方法 本研究以来源不同的两年生紫花桔梗茎叶为实验材料, 利用UPLC-Q/Orbitrap HRMS, 在负离子模式下, 采用轨道阱一级全扫描和数据依赖型离子阱二级扫描对桔梗茎叶的提取物进行分析, 筛选不同来源的桔梗茎叶差异代谢物。结果 桔梗茎叶中共检测到18个代谢产物, 其中包括黄酮类化合物4个, 炔苷类成分2个, 皂苷类成分12个(未见报道的代谢物1个), 并且推断出该未知化合物基本结构为远志酸型皂苷元-葡萄糖-木糖/阿拉伯糖苷。通过比较分析, 发现了不同来源的桔梗在化学成分上的差异, 筛选了6个中韩桔梗差异代谢物及1个延边地区桔梗差异代谢物。结论 桔梗茎叶具有丰富的化学成分, 不同来源的桔梗茎叶具有化合物差异性, 具有较高的开发利用前景, 为桔梗地上部资源的开发利用提供理论依据。

, correspAuthors=朴向民, 林春梅, authorNote=null, correspAuthorsNote=
* 朴向民(1983—), 女, 博士, 讲师, 主要研究方向为药用植物种质资源与开发研究。E-mail:
林春梅(1982—), 女, 博士, 讲师, 主要研究方向为中药资源开发利用研究。E-mail:
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#毕长安和连俊美为共同第一作者

毕长安(2001—), 男, 硕士研究生, 主要研究方向为桔梗种质资源评价研究。E-mail:

连俊美(2000—), 女, 硕士研究生, 主要研究方向为药用植物种质资源评价研究。E-mail:

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毕长安(2001—), 男, 硕士研究生, 主要研究方向为桔梗种质资源评价研究。E-mail:

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毕长安(2001—), 男, 硕士研究生, 主要研究方向为桔梗种质资源评价研究。E-mail:

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连俊美(2000—), 女, 硕士研究生, 主要研究方向为药用植物种质资源评价研究。E-mail:

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连俊美(2000—), 女, 硕士研究生, 主要研究方向为药用植物种质资源评价研究。E-mail:

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Sustainability, 2022, 14(10): 6285., articleTitle=Changes in the platycodin content and physiological characteristics during the fruiting stage of Platycodon grandiflorum under drought stress, refAbstract=null), Reference(id=1175086871060295983, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, doi=null, pmid=null, pmcid=null, year=2024, volume=16, issue=3, pageStart=392, pageEnd=400, url=null, language=null, rfNumber=[31], rfOrder=45, authorNames=SHI L, CUI T, WANG XY, journalName=Chinese Herbal Medicines, refType=null, unstructuredReference=SHI L, CUI T, WANG XY, et al. Biotransformation and pharmacological activities of platycosides from Platycodon grandiflorum roots[J]. Chinese Herbal Medicines, 2024, 16(3): 392-400., articleTitle=Biotransformation and pharmacological activities of platycosides from Platycodon grandiflorum roots, refAbstract=null), Reference(id=1175086871148376369, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, doi=null, pmid=null, pmcid=null, year=2024, volume=271, issue=null, pageStart=132617, pageEnd=null, url=null, language=null, rfNumber=[32], rfOrder=46, authorNames=ZHANG Y, SUN M, HE Y, journalName=International Journal of Biological Macromolecules, refType=null, unstructuredReference=ZHANG Y, SUN M, HE Y, et al. Polysaccharides from Platycodon grandiflorum: A review of their extraction, structures, modifications, and bioactivities[J]. International Journal of Biological Macromolecules, 2024, 271: 132617., articleTitle=Polysaccharides from Platycodon grandiflorum: A review of their extraction, structures, modifications, and bioactivities, refAbstract=null), Reference(id=1175086871265816883, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, doi=null, pmid=null, pmcid=null, year=2020, volume=82, issue=null, pageStart=153442, pageEnd=null, url=null, language=null, rfNumber=[33], rfOrder=47, authorNames=HSU WC, RAMESH S, SHIBU MA, journalName=Phytomedicine, refType=null, unstructuredReference=HSU WC, RAMESH S, SHIBU MA, et al. Platycodin D reverses histone deacetylase inhibitor resistance in hepatocellular carcinoma cells by repressing ERK1/2-mediated cofilin-1 phosphorylation[J]. Phytomedicine, 2020, 82: 153442., articleTitle=Platycodin D reverses histone deacetylase inhibitor resistance in hepatocellular carcinoma cells by repressing ERK1/2-mediated cofilin-1 phosphorylation, refAbstract=null)], funds=[Fund(id=1175086866975043776, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, awardId=20210402050GH, language=CN, fundingSource=吉林省科技发展计划项目(20210402050GH), fundOrder=null, country=null), Fund(id=1175086867058929857, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, awardId=20220204082YY, language=CN, fundingSource=吉林省科技发展计划项目(20220204082YY), fundOrder=null, country=null), Fund(id=1175086867130233026, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, awardId=202310193051, language=CN, fundingSource=2023年大学生创新创业训练计划项目(202310193051), fundOrder=null, country=null)], companyList=[AuthorCompany(id=1175086863573463178, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, xref=null, ext=[AuthorCompanyExt(id=1175086863577657483, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, companyId=1175086863573463178, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=College of Traditional Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, China), AuthorCompanyExt(id=1175086863586046092, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, companyId=1175086863573463178, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=吉林农业大学中药材学院, 长春 130118)])], figs=[ArticleFig(id=1175086865540591790, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=EN, label=Fig.1, caption=Chromatogram analysis of stems and leaves of two-year-old purple flowered Platycodon grandiflorum from China and South Korea, figureFileSmall=fIIiKbV9COZStP35QcCOQg==, figureFileBig=zzdR2HxgZoczvbln7MziWw==, tableContent=null), ArticleFig(id=1175086865737724079, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=CN, label=图1, caption=中国和韩国两年生紫花桔梗茎叶色谱图分析

注: 1. 木犀草素-葡萄糖-鼠李糖苷; 2. 木犀草素-7-O-葡萄糖苷; 3. 芹菜素-葡萄糖-鼠李糖苷; 4. 芹菜素-葡萄糖苷; 5. 党参苷I; 6. 党参炔苷; 7. platysaponin A; 8. Mal-platysaponin A; 9. 远志酸型皂苷元-葡萄糖-木糖/阿拉伯糖苷; 10. Ac-platysaponin A; 11. 3’-O-乙酰基-桔梗皂苷D2或同分异构体; 12. 乙酰基-桔梗皂苷D或其同分异构体; 13. 3”-O-乙酰基-远志皂苷D3或同分异构体; 14. 桔梗皂苷L或同分异构体; 15. 3’-O-乙酰基-桔梗皂苷D2或同分异构体; 16. 乙酰基-桔梗皂苷D或同分异构体; 17. 3”-O-乙酰基-远志皂苷D3或同分异构体; 18. 桔梗皂苷L或同分异构体。

, figureFileSmall=fIIiKbV9COZStP35QcCOQg==, figureFileBig=zzdR2HxgZoczvbln7MziWw==, tableContent=null), ArticleFig(id=1175086865834193072, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=EN, label=Fig.2, caption=PLS-DA analysis of metabolites in stems and leaves of Platycodon grandiflorum, figureFileSmall=N2pKzwQpdJTD2Bs09zURqQ==, figureFileBig=X9f8YKXhuPBrSICzWA/mNA==, tableContent=null), ArticleFig(id=1175086865909690545, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=CN, label=图2, caption=紫花桔梗茎叶代谢物PLS-DA分析, figureFileSmall=N2pKzwQpdJTD2Bs09zURqQ==, figureFileBig=X9f8YKXhuPBrSICzWA/mNA==, tableContent=null), ArticleFig(id=1175086865964216498, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=EN, label=Fig.3, caption=Heatmap analysis of metabolites in stems and leaves of two-year-old purple flowered Platycodon grandiflorum from different sources, figureFileSmall=75cCnUN+/bawQztYjNJIHw==, figureFileBig=KgtUDMk4eB7hd1suyFCp0g==, tableContent=null), ArticleFig(id=1175086866027131059, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=CN, label=图3, caption=不同来源的二年生紫花桔梗茎叶代谢物热图分析, figureFileSmall=75cCnUN+/bawQztYjNJIHw==, figureFileBig=KgtUDMk4eB7hd1suyFCp0g==, tableContent=null), ArticleFig(id=1175086866115211444, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=EN, label=Fig.4, caption=Metabolite analysis of significant differences in stems and leaves of purple flowered Platycodon grandiflorum between South Korea and China, figureFileSmall=QHBMCHEP0ZbhCUvNQcbXiA==, figureFileBig=wVF5mypLls+Sq1BTiZaXow==, tableContent=null), ArticleFig(id=1175086866228457653, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=CN, label=图4, caption=韩国与中国紫花桔梗茎叶显著差异代谢物分析, figureFileSmall=QHBMCHEP0ZbhCUvNQcbXiA==, figureFileBig=wVF5mypLls+Sq1BTiZaXow==, tableContent=null), ArticleFig(id=1175086866316538038, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=EN, label=Table 1, caption=

Source information of Platycodon grandiflorum samples

, figureFileSmall=null, figureFileBig=null, tableContent=
序号 样品号 来源地 收集时间/年
1 HG-1 韩国全罗南道 2017
2 HG-2 韩国全罗南道 2017
3 HG-3 韩国春川 2017
4 HG-4 韩国阴城 2017
5 HG-5 韩国阴城 2019
6 HG-6 韩国仁川 2019
7 ZG-1 中国安国 2018
8 ZG-2 中国延边 2019
9 ZG-3 中国安国 2018
10 ZG-4 中国赤峰 2019
11 ZG-5 中国赤峰 2019
12 ZG-6 中国赤峰 2018
13 ZG-7 中国赤峰 2018
14 ZG-8 中国安国 2019
15 ZG-9 中国延边 2018
16 ZG-10 中国延边 2018
), ArticleFig(id=1175086866392035511, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=CN, label=表1, caption=

桔梗样品来源信息

, figureFileSmall=null, figureFileBig=null, tableContent=
序号 样品号 来源地 收集时间/年
1 HG-1 韩国全罗南道 2017
2 HG-2 韩国全罗南道 2017
3 HG-3 韩国春川 2017
4 HG-4 韩国阴城 2017
5 HG-5 韩国阴城 2019
6 HG-6 韩国仁川 2019
7 ZG-1 中国安国 2018
8 ZG-2 中国延边 2019
9 ZG-3 中国安国 2018
10 ZG-4 中国赤峰 2019
11 ZG-5 中国赤峰 2019
12 ZG-6 中国赤峰 2018
13 ZG-7 中国赤峰 2018
14 ZG-8 中国安国 2019
15 ZG-9 中国延边 2018
16 ZG-10 中国延边 2018
), ArticleFig(id=1175086866505281721, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=EN, label=Table 2, caption=

Elution gradient program

, figureFileSmall=null, figureFileBig=null, tableContent=
时间/min 流速/(mL/min) A (0.1%甲酸/水)/% B(乙腈)/%
0~2 0.3 90 10
2~8 0.3 90~50 10~50
8~30 0.3 50~30 50~70
30~31 0.3 30~2 70~98
31~32 0.3 2 98
32~33 0.3 2~90 98~10
33~35 0.3 90 10
), ArticleFig(id=1175086866572390587, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=CN, label=表2, caption=

洗脱梯度程序

, figureFileSmall=null, figureFileBig=null, tableContent=
时间/min 流速/(mL/min) A (0.1%甲酸/水)/% B(乙腈)/%
0~2 0.3 90 10
2~8 0.3 90~50 10~50
8~30 0.3 50~30 50~70
30~31 0.3 30~2 70~98
31~32 0.3 2 98
32~33 0.3 2~90 98~10
33~35 0.3 90 10
), ArticleFig(id=1175086866656276669, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=EN, label=Table 3, caption=

Metabolites detected in the stems and leaves of Platycodon grandiflorum

, figureFileSmall=null, figureFileBig=null, tableContent=
编号 保留时间
/min		 一质谱数据
(m/z)		 加和离子 二级离子
信息		 鉴定结果 化合物
类别		 功效作用
化合物1 4.57 593.15 [M-H]- 447.13-285.04 木犀草素-葡萄糖-鼠李糖苷 黄酮 抗炎、抗菌、抗肿瘤、抗氧化和抗病毒等[12]
化合物2 4.75 447.10 [M-H]- 285.04 木犀草素-7-O-葡萄糖苷* 黄酮 抗炎、抗菌、抗肿瘤、抗氧化和抗病毒等[12]
化合物3 7.15 577.16 [M-H]- 431.10-269.05 芹菜素-葡萄糖-鼠李糖苷 黄酮 抗氧化、抗癌等[13]
化合物4 7.56 431.10 [M-H]- 269.05 芹菜素-葡萄糖苷 黄酮 抗氧化、抗癌等[13]
化合物5 8.12 723.51 [M+COOH]- 677.12-497.17-453.17-
291.12		 党参苷I* 炔苷 抗溃疡、抗氧化、抗疟疾、抗心律失常、抗癌、保护心脏和肾等[14]
化合物6 11.04 441.17 [M+COOH]- 441.17-305.12-215.10-
185.09-179.05		 党参炔苷* 炔苷 抗溃疡、抗氧化、抗疟疾、抗心律失常、抗癌、保护心脏和肾等[14]
化合物7 13.00 827.45 [M-H]- 665.39-441.33-390.39 platysaponin A 皂苷 桔梗皂苷具有抗氧化、祛痰止咳、抗炎、镇痛解热等功效。目前对于桔梗皂苷单体化合物的药理研究大部分集中在桔梗皂苷D, 其他桔梗皂苷单体的药理作用几乎未见报道[15-20]
合物8 16.50 913.45 [M-H]- 869.46-827.44-665.40-
441.33		 Mal-platysaponin A 皂苷
化合物9 17.19 797.44 [M-H]- 665.39-503.40 远志酸型皂苷元-葡萄糖-木糖/阿拉伯糖苷 皂苷
化合物10 18.40 869.40 [M-H]- 827.44-665.39-441.33-
390.39		 Ac-platysaponin A 皂苷
化合物11 23.86 1473.64 [M+COOH]- 1427.63-1367.62-1222.49-
885.44-843.44-663.37-
519.33-469.15		 3’-O-乙酰基-桔梗皂苷D2或同分异构体 皂苷
化合物12 24.21 1265.53 [M-H]- 1265.58-1223.57-1133.54-
987.49-795.43-681.39-
469.16-457.33		 乙酰基-桔梗皂苷D或同分异构体 皂苷
化合物13 24.63 1411.64 [M-H]- 1411.63-1351.64-1279.59-
911.48-827.44-647.38-
541.18-469.16		 3”-O-乙酰基-远志皂苷D3或同分异构体 皂苷
化合物14 25.78 1279.56 [M-H]- 1279.56-1237.55-1147.52-
937.44-827.40-695.36-
519.33-469.16		 桔梗皂苷L或同分异构体 皂苷
化合物15 26.70 1473.64 [M+COOH]- 1427.63-1367.62-1222.49-
885.44-843.44-663.37-
519.33-469.15		 3’-O-乙酰基-桔梗皂苷D2或同分异构体 皂苷
化合物16 27.14 1265.58 [M-H]- 1265.58-1223.57-1115.52-
795.42-681.39-469.16-
457.33		 乙酰基-桔梗皂苷D或同分异构体 皂苷
化合物17 27.50 1411.64 [M-H]- 1411.63-1351.64-1279.59-
911.48-827.44-647.38-
541.18-469.15		 3”-O-乙酰基-远志皂苷D3或同分异构体 皂苷
化合物18 28.86 1279.56 [M-H]- 1279.56-1249.54-1207.54-
1069.49-895.42-727.38-
621.37-485.29		 桔梗皂苷L或同分异构体 皂苷
), ArticleFig(id=1175086866786300095, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153433638973726792, language=CN, label=表3, caption=

紫花桔梗茎叶中检测到的代谢物

, figureFileSmall=null, figureFileBig=null, tableContent=
编号 保留时间
/min		 一质谱数据
(m/z)		 加和离子 二级离子
信息		 鉴定结果 化合物
类别		 功效作用
化合物1 4.57 593.15 [M-H]- 447.13-285.04 木犀草素-葡萄糖-鼠李糖苷 黄酮 抗炎、抗菌、抗肿瘤、抗氧化和抗病毒等[12]
化合物2 4.75 447.10 [M-H]- 285.04 木犀草素-7-O-葡萄糖苷* 黄酮 抗炎、抗菌、抗肿瘤、抗氧化和抗病毒等[12]
化合物3 7.15 577.16 [M-H]- 431.10-269.05 芹菜素-葡萄糖-鼠李糖苷 黄酮 抗氧化、抗癌等[13]
化合物4 7.56 431.10 [M-H]- 269.05 芹菜素-葡萄糖苷 黄酮 抗氧化、抗癌等[13]
化合物5 8.12 723.51 [M+COOH]- 677.12-497.17-453.17-
291.12		 党参苷I* 炔苷 抗溃疡、抗氧化、抗疟疾、抗心律失常、抗癌、保护心脏和肾等[14]
化合物6 11.04 441.17 [M+COOH]- 441.17-305.12-215.10-
185.09-179.05		 党参炔苷* 炔苷 抗溃疡、抗氧化、抗疟疾、抗心律失常、抗癌、保护心脏和肾等[14]
化合物7 13.00 827.45 [M-H]- 665.39-441.33-390.39 platysaponin A 皂苷 桔梗皂苷具有抗氧化、祛痰止咳、抗炎、镇痛解热等功效。目前对于桔梗皂苷单体化合物的药理研究大部分集中在桔梗皂苷D, 其他桔梗皂苷单体的药理作用几乎未见报道[15-20]
合物8 16.50 913.45 [M-H]- 869.46-827.44-665.40-
441.33		 Mal-platysaponin A 皂苷
化合物9 17.19 797.44 [M-H]- 665.39-503.40 远志酸型皂苷元-葡萄糖-木糖/阿拉伯糖苷 皂苷
化合物10 18.40 869.40 [M-H]- 827.44-665.39-441.33-
390.39		 Ac-platysaponin A 皂苷
化合物11 23.86 1473.64 [M+COOH]- 1427.63-1367.62-1222.49-
885.44-843.44-663.37-
519.33-469.15		 3’-O-乙酰基-桔梗皂苷D2或同分异构体 皂苷
化合物12 24.21 1265.53 [M-H]- 1265.58-1223.57-1133.54-
987.49-795.43-681.39-
469.16-457.33		 乙酰基-桔梗皂苷D或同分异构体 皂苷
化合物13 24.63 1411.64 [M-H]- 1411.63-1351.64-1279.59-
911.48-827.44-647.38-
541.18-469.16		 3”-O-乙酰基-远志皂苷D3或同分异构体 皂苷
化合物14 25.78 1279.56 [M-H]- 1279.56-1237.55-1147.52-
937.44-827.40-695.36-
519.33-469.16		 桔梗皂苷L或同分异构体 皂苷
化合物15 26.70 1473.64 [M+COOH]- 1427.63-1367.62-1222.49-
885.44-843.44-663.37-
519.33-469.15		 3’-O-乙酰基-桔梗皂苷D2或同分异构体 皂苷
化合物16 27.14 1265.58 [M-H]- 1265.58-1223.57-1115.52-
795.42-681.39-469.16-
457.33		 乙酰基-桔梗皂苷D或同分异构体 皂苷
化合物17 27.50 1411.64 [M-H]- 1411.63-1351.64-1279.59-
911.48-827.44-647.38-
541.18-469.15		 3”-O-乙酰基-远志皂苷D3或同分异构体 皂苷
化合物18 28.86 1279.56 [M-H]- 1279.56-1249.54-1207.54-
1069.49-895.42-727.38-
621.37-485.29		 桔梗皂苷L或同分异构体 皂苷
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基于超高效液相色谱-串联四极杆/轨道阱高分辨质谱法分析桔梗茎叶代谢物
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毕长安 # , 连俊美 # , 闫艳 , 朴向民 * , 林春梅 *
食品安全质量检测学报 | 食品分析与检测 2025,16(6): 275-283
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食品安全质量检测学报 | 食品分析与检测 2025, 16(6): 275-283
基于超高效液相色谱-串联四极杆/轨道阱高分辨质谱法分析桔梗茎叶代谢物
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毕长安# , 连俊美# , 闫艳, 朴向民* , 林春梅*
作者信息
  • 吉林农业大学中药材学院, 长春 130118

    • 毕长安(2001—), 男, 硕士研究生, 主要研究方向为桔梗种质资源评价研究。E-mail:

    连俊美(2000—), 女, 硕士研究生, 主要研究方向为药用植物种质资源评价研究。E-mail:

通讯作者:

* 朴向民(1983—), 女, 博士, 讲师, 主要研究方向为药用植物种质资源与开发研究。E-mail:
林春梅(1982—), 女, 博士, 讲师, 主要研究方向为中药资源开发利用研究。E-mail:
Metabolite composition analysis of leaves and stems of Platycodon grandiflorus based on ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry
Chang-An BI , Jun-Mei LIAN , Yan YAN, Xiang-Min PIAO* , Chun-Mei LIN*
Affiliations
  • College of Traditional Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, China
出版时间: 2025-03-25 doi: 10.19812/j.cnki.jfsq11-5956/ts.20241213003
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摘要
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目的 基于超高效液相色谱-串联四极杆/轨道阱高分辨质谱法(ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry, UPLC-Q/Orbitrap HRMS)分析桔梗茎叶中代谢物的种类和含量。方法 本研究以来源不同的两年生紫花桔梗茎叶为实验材料, 利用UPLC-Q/Orbitrap HRMS, 在负离子模式下, 采用轨道阱一级全扫描和数据依赖型离子阱二级扫描对桔梗茎叶的提取物进行分析, 筛选不同来源的桔梗茎叶差异代谢物。结果 桔梗茎叶中共检测到18个代谢产物, 其中包括黄酮类化合物4个, 炔苷类成分2个, 皂苷类成分12个(未见报道的代谢物1个), 并且推断出该未知化合物基本结构为远志酸型皂苷元-葡萄糖-木糖/阿拉伯糖苷。通过比较分析, 发现了不同来源的桔梗在化学成分上的差异, 筛选了6个中韩桔梗差异代谢物及1个延边地区桔梗差异代谢物。结论 桔梗茎叶具有丰富的化学成分, 不同来源的桔梗茎叶具有化合物差异性, 具有较高的开发利用前景, 为桔梗地上部资源的开发利用提供理论依据。

紫花桔梗  /  茎叶  /  化学成分  /  超高效液相色谱-串联四极杆/轨道阱高分辨质谱法

Objective To analyse the types and content of metabolites in the stems and leaves of Platycodon grandiflorus by ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry (UPLC-Q/Orbitrap HRMS). Methods Stems and leaves of two-year-old purple flowered Platycodon grandiflorus from different sources was used as experimental materials. UPLC-Q/Orbitrap HRMS technology was used to analyze the extracts of Platycodon grandiflorus stems and leaves in negative ion mode, using orbitrap for MS1 full scan and data dependent acquisition ion trap for MS2 scan, and screen for differential metabolites of Platycodon grandiflorum stems and leaves from different sources. Results A total of 18 metabolites were detected in the stems and leaves of Platycodon grandiflorum, including 4 flavonoids, 2 alkynyl glycosides, and 12 saponins (1 metabolite that had not been reported). The basic structure of this unknown compound was polygalacic acid-glucose- xylose/arabic glycoside. Through comparative analysis, differences in chemical composition of Platycodon grandiflorus among different sources were discovered. The 6 differential metabolites of Platycodon grandiflorus from China and South Korea and 1 differential metabolite of Platycodon grandiflorus from Yanbian area were screened. Conclusion The comprehensive analysis results indicate that the stems and leaves of Platycodon grandiflorus have rich chemical components, and the stems and leaves of Platycodon grandiflorus from different sources have compound differences, which have high development and utilization prospects, providing theoretical basis for the development and utilization of aboveground resources of Platycodon grandiflorus.

purple flowered Platycodon grandiflorum  /  leaves and stems  /  chemical composition  /  ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry
毕长安, 连俊美, 闫艳, 朴向民, 林春梅. 基于超高效液相色谱-串联四极杆/轨道阱高分辨质谱法分析桔梗茎叶代谢物. 食品安全质量检测学报, 2025 , 16 (6) : 275 -283 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20241213003
Chang-An BI, Jun-Mei LIAN, Yan YAN, Xiang-Min PIAO, Chun-Mei LIN. Metabolite composition analysis of leaves and stems of Platycodon grandiflorus based on ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry[J]. Journal of Food Safety & Quality, 2025 , 16 (6) : 275 -283 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20241213003
正文
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0 引言
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桔梗(Platycodon grandiflorum), 为桔梗科(Campanulaceae)桔梗属(Platycodon)多年生植物。在我国东北、华北地区以及日本、韩国、俄罗斯等多个地区有分布[1]。桔梗含有皂苷、黄酮、甾醇、聚乙炔、酚类、挥发油、脂肪酸和氨基酸等多种化学成分, 具有祛痰、镇咳、抗炎、抗氧化、抗癌、保护心血管和改善血脂等作用[2‒6]。2002年, 桔梗被我国卫计委列入第一批药食同源名录; 2021年, 桔梗以蔬菜类别被列为国家农产品地理标志产品[7]。桔梗是朝鲜、韩国及我国东北地区的经典腌菜制品之一, 其根、茎、叶、花均对人们的健康有益处[1,8], 在食品及保健食品开发方面有巨大的开发潜力。在我国, 桔梗作为食品和药品的原料, 其利用历史久远且用途广阔, 但是目前市场上的桔梗产品大多是以根为原料的[9‒10], 桔梗的地上部作为桔梗植物的重要组成部分, 其利用率非常低。现代研究表明, 桔梗茎叶中存在大量黄酮类活性成分, 使用浸提物法提取的桔梗茎叶中的化合物具有抗炎、抗氧化等功效, 与桔梗根部相比, 桔梗茎叶资源具有更加丰富的黄酮类化合物[1,8,11], 桔梗地上部资源具有广阔的开发利用前景, 但是目前关于桔梗茎叶代谢物的研究相对较少, 特别是关于桔梗茎叶皂苷类化合物鉴定的相关研究更是十分有限, 在本研究发现桔梗茎叶中含有丰富的皂苷类化学成分, 桔梗皂苷作为桔梗中重要的功效成分, 具有很高的研究价值。因此, 基于现代科学技术深入研究桔梗茎叶的代谢物成分, 将桔梗茎叶合理开发利用, 为进一步开发多样化的桔梗食品, 对桔梗资源的精深加工以及避免桔梗资源浪费具有重要意义。
本研究以来源地不同的桔梗茎叶为研究对象, 采用超高效液相色谱-串联四极杆/轨道阱高分辨质谱(ultra performance liquid chromatography-Quadrupole/Orbitrap high-resolution mass spectrometry, UPLC-Q/Orbitrap HRMS)技术结合Xcalibur 2.1软件进行数据处理, 并结合特征离子、裂解规律和文献参考对其代谢物成分进行成分鉴定, 为研究桔梗化学成分的鉴定提供了一种高效的方法, 不仅可以更深入地了解桔梗茎叶的代谢物成分, 还可以为桔梗地上部的资源开发、利用和保护提供科学依据和理论支持。
1 材料与方法
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1.1 材料与试剂
实验材料为10份国产紫花桔梗与6份韩国产紫花桔梗种子, 其采集地如表1所示。所有收集的种子材料均于2020年在吉林省左家镇实验基地进行穴播, 小区行长3 m, 宽1.2 m, 播种密度为10 cm×20 cm, 每份材料设3组小区重复, 田间管理与当地种植生产相同。
木犀草素-7-O-葡萄糖苷、党参苷、党参炔苷(纯度均大于98%, 上海源叶生物科技有限公司); 甲醇、乙腈、纯水(质谱级, 美国赛默飞世尔科技公司)。
1.2 仪器与设备
FSN10450轨道阱三合一高分辨质谱仪、Vanquish3000液相色谱系统、Hypersil GLOD VANQUISH aQ色谱柱(100 mm×2.1 mm, 1.9 μm)(美国赛默飞世尔科技公司)。
1.3 实验方法
1.3.1 桔梗地上部样品提取
采取两年生桔梗的茎叶清洗干净并于‒70 ℃冻干后, 研磨成粉末, 过40目筛, 精确称量各0.5 g, 放入15 mL离心管中, 添加4 mL的80%甲醇溶液, 在室温条件下超声(100 W, 40 kHz)进行30 min提取, 然后10000 r/min离心15 min, 取其上清液。连续提取3次, 合并上清液, 经0.22 μm的滤膜将其过滤, 取出滤液, 放入样品瓶中, 待用。
1.3.2 对照品溶液制备
精密称取木犀草素-7-O-葡萄糖苷、党参苷、党参炔苷对照品适量, 将其放入50 mL棕色量瓶中, 加甲醇制成质量浓度分别为53.8、55.2、56.3 μg/mL的混合对照品溶液。
1.3.3 色谱条件
柱温箱温度: 35 ℃; 洗脱梯度程序见表2; 进样量1 μL。
1.3.4 质谱条件
质谱检测为负离子模式2700 V。每份样品分别采用轨道阱一级全扫描和数据依赖型离子阱二级扫描进行定量, 定性分析。离子源条件: 鞘气流速40 Arb; 辅助气流速5 Arb; 离子传输管温度320 ℃; 雾化器温度320 ℃; 扫描范围350~1500 m/z; 高能碰撞解离(high energy collision dissociation, HCD)碰撞能40%; 轨道阱分辨率60000。
1.4 数据处理
使用中国知网、万方、PubChem等数据平台查找桔梗茎叶的化学成分、质谱碎片信息, 并创建包括化合物名称、分子式、二级质谱碎片等信息的桔梗相关质谱数据库, 其中包含对照标准品、已报道的化合物的质谱数据和相应的离子信息。使用Compound Discoverer 3.0结合Xcalibur 2.1软件进行质谱数据的处理、分析。结合保留时间、准确的分子质量、二级碎片信息和离子裂解规律, 可准确鉴定和分析样品中的化合物。在本研究中差异代谢物的筛选依据Metabo analyst 6.0在线数据分析系统, 主要通过偏最小二乘法分析(orthogonal partial least squares-discriminant analysis, OPLS-DA)、单因素方差分析(one-way analysis of variance, One-way ANOVA)检验进行筛选。首先对各组数据进行正交OPLS-DA, 根据OPLS-DA分析变量投影重要度(variable importance for the projection, VIP), 选择VIP大于1且通过One-way ANOVA检验差异显著(P<0.05)即为差异代谢物。
2 结果与分析
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2.1 两年生桔梗茎叶中检测到的代谢物成分分析
本研究采用UPLC-Q/Orbitrap HRMS技术, 取不同来源的两年生紫花桔梗茎叶提取物进行进样分析; 图1为中韩紫花桔梗茎叶提取物在负离子模式下的总离子流色谱图, 由图1可看出, 中韩桔梗的色谱图分离效果较好, 响应值高, 两组样品的相似度比较高, 化合物峰3、4、5、8、9、10的重叠度比较小, 说明不同来源的桔梗茎叶中的代谢物种类和含量都有所差异。在紫花桔梗的总离子流色谱图中, 对负离子模式下的主要峰进行标记, 并对主要峰进行统计, 总共获得23个峰, 在电喷雾质谱一级结构中获得标记峰的相对质荷比信息, 通过质谱二级碎片信息分析并结合标准品保留时间及非标准品的相关文献信息对各主要分子离子峰进行指认, 最终鉴定出18个化合物, 对应的离子峰的相关信息见表3, 其中包含黄酮类化合物4个(化合物1~4), 炔苷类成分2个(化合物5、6), 皂苷类成分12个(化合物7~18), 其中发现未见报道的代谢物1个(化合物9)。皂苷类成分中发现丙二酰基类皂苷1个(化合物8), 乙酰基类皂苷7个(化合物10~13、15~17)。根据未知化合物二级离子碎片的裂解规律, 推断出其基本结构为远志酸型皂苷元(碎片离子503)-葡萄糖(碎片离子162)-木糖/阿拉伯糖苷(碎片离子132), 具体化学结构有待进一步研究确定。以上结果可以看出, 黄酮和皂苷类化合物为紫花桔梗茎叶中主要的化学成分, 并且相对于桔梗根部, 桔梗茎叶中含有更加丰富的乙酰基化桔梗皂苷类成分。
2.2 二年生中国与韩国紫花桔梗茎叶中的代谢物OPLS-DA分析
为确定中韩紫花桔梗茎叶之间的代谢物是否存在差异, 本研究进行了OPLS-DA分析, OPLS-DA判别模型如图2所示, 中韩桔梗之间存在明显的分离, 分别形成两个不同的类群, 表明中韩两种桔梗茎叶的代谢物存在明显差异。来源不同的国产桔梗分析显示: 延边桔梗和安国桔梗可各自集为一个类群, 而赤峰桔梗未能得到有效的分离。如图2A所示, 模型使用5个主成分时拟合效果最好, Q2为0.7543, 说明模型预测能力较强, R2X和R2Y分别为0.8334和0.9012, 说明模型对不同来源的桔梗茎叶代谢物成分总体变异贡献的百分比较高。OPLS-DA模型中VIP常用筛选差异物质, VIP越大, 表明该变量对组间差异的贡献越大。本研究将VIP大于1的物质认定为差异代谢物, 筛选出6种差异化合物, 如图2B所示: 按照VIP大小分别为: 化合物4、3、10、9、8、7。由于来源不同的桔梗资源是在相同环境下生长, 样本之间的显著分布差异可能与它们的品种特性相关。
2.3 二年生紫花桔梗茎叶代谢物热图分析
经过对数转换的差异代谢物丰度数据聚类分析热图, 如图3所示, 其中每一行代表一个特定的化合物, 每一列代表一个样本(红色代表安国样本, 绿色代表赤峰样本, 深蓝色代表延边样本, 浅蓝色代表韩国样本), 颜色的变化表示化合物丰度的不同水平。颜色越深, 代表丰度值越高; 颜色越浅, 丰度值越低。从图3中可以看到, 与OPLS-DA分析结果一致, 从中韩两国的桔梗茎叶中可筛选出6个差异代谢物, 化合物3在韩国桔梗茎叶中丰度较高, 而化合物4、7~10在国产桔梗茎叶中的丰度较高。筛选一个化合物(化合物6)用来区分延边地区和其他地区的紫花桔梗, 其在延边桔梗茎叶中的丰度较高。
2.4 显著差异代谢物violin-plot分析
为更加明显地显示不同来源的桔梗茎叶代谢物之间的差异, 对筛选出来的差异代谢物进行了violin-plot分析, 结果如图4所示。在韩国桔梗茎叶(图中蓝色图形)中化合物3峰面积的中位值、最高值、最低值均高于国内桔梗(红色、绿色和紫色图形), 而化合物4、8~10化合物峰面积在中国桔梗中的中位值、最高值、最低值均高于韩国桔梗。中国桔梗化合物7的中位值高于韩国桔梗。化合物6在延边桔梗中的中位值高于安国和赤峰桔梗。通过化合物二级碎片离子信息(表1), 进一步分析得出这些差异代谢物是母核为芹菜素类化合物(化合物3、4, 都具有269的离子碎片), 及platysaponin A的丙二酰基化及乙酰基化的衍生物(化合物7~10, 都具有665的离子碎片)。这些发现为中韩两国桔梗茎叶代谢物的合理利用提供了宝贵线索, 这些代谢物可能具有保健功效, 具有潜在的食品和保健食品开发利用前景, 进一步为我国桔梗向韩国市场输出提供理论支持。
3 讨论与结论
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生长在不同地区的同种植物会形成不同的生态型, 这是因为植物的遗传、形态和生理代谢会在与环境的长期相互作用中发生变化, 且植物的生长范围越广, 变异性就越大[9‒11]。在本研究中, 收集不同来源地的紫花桔梗种子, 在同一环境下进行播种, 以在完全相同的生长条件下的桔梗茎叶为研究对象, 增加了样本的多样性, 这将有助于更好地了解不同来源地的紫花桔梗的化学成分的差异及其影响因素, 为进一步研究其是否会产生特定的保健功效奠定基础。
本研究采用了UPLC-Q/Orbitrap HRMS技术, 对中韩紫花桔梗茎叶中的化学成分进行分析, 共鉴定了18个主要代谢物。过去的研究大部分集中于对桔梗根的研究, 充分利用桔梗根部的营养物质[21‒25], 而通过本研究, 发现桔梗茎叶中也含有丰富的黄酮类、皂苷类、炔苷类成分。在桔梗的生长发育过程中, 由于茎叶的生长需要营养物质, 可能与根系发生竞争, 进而会使根的产量受到影响, 增加了种植管理成本[26], 因此建议可以将桔梗茎叶利用起来, 对桔梗全株的开发利用是具有可行性和必要性的。在本研究中发现桔梗茎叶中的主要代谢产物在不同来源地的桔梗中有显著的差异, 这为桔梗地上部资源的开发和利用提供了依据。以往的研究表明, 桔梗皂苷是桔梗的主要功效成分[27‒30], 通过本次研究, 发现桔梗茎叶中也存在丰富的皂苷成分, 并且比起根部, 桔梗茎叶中含有更加丰富的乙酰基化桔梗皂苷类型, 可能具有一些特殊的功效作用, 因此可以推测桔梗茎叶中的有效成分能够在未来的食品及保健食品研发中发挥极大的潜力。另外, 本研究中发现在桔梗茎叶中含有1个未见报道的化合物, 通过对其离子碎片的分析, 可以确认该化合物基本结构为远志酸型皂苷元-葡萄糖-木糖/阿拉伯糖苷, 根据以往研究结果, 该化合物可能具有抗炎、抗氧化、抗菌/抗真菌、抗肿瘤、神经保护和心血管保护等多种药理作用[30‒33]。药食同源是中医药学特有的健康理论, 是饮食文化与中医药文化共同发展的成果, 以药食同源理念养生, 必将成为大健康产业的发展趋势。桔梗作为药食同源代表性药材之一, 充分利用其地上部资源, 开发出更多满足现代人群健康需求的新的桔梗资源食品和保健食品, 以期为提高我国桔梗健康品的产品创新能力和市场竞争力提供理论依据。
基金
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  • 吉林省科技发展计划项目(20210402050GH)
  • 吉林省科技发展计划项目(20220204082YY)
  • 2023年大学生创新创业训练计划项目(202310193051)
文献
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2025年第16卷第6期
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doi: 10.19812/j.cnki.jfsq11-5956/ts.20241213003
  • 接收时间：2024-12-13
  • 首发时间：2025-07-19
  • 出版时间：2025-03-25
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  • 收稿日期：2024-12-13
基金
吉林省科技发展计划项目(20210402050GH)
吉林省科技发展计划项目(20220204082YY)
2023年大学生创新创业训练计划项目(202310193051)
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    吉林农业大学中药材学院, 长春 130118

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* 朴向民(1983—), 女, 博士, 讲师, 主要研究方向为药用植物种质资源与开发研究。E-mail:
林春梅(1982—), 女, 博士, 讲师, 主要研究方向为中药资源开发利用研究。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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