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Article(id=1217845645432509146, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1217845635080962613, articleNumber=null, orderNo=null, doi=10.19812/j.cnki.jfsq11-5956/ts.20250217007, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1739721600000, receivedDateStr=2025-02-17, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1768286628348, onlineDateStr=2026-01-13, pubDate=1756051200000, pubDateStr=2025-08-25, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1768286628348, onlineIssueDateStr=2026-01-13, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1768286628348, creator=13701087609, updateTime=1768286628348, updator=13701087609, issue=Issue{id=1217845635080962613, tenantId=1146029695717560320, journalId=1149652044408987649, year='2025', volume='16', issue='16', pageStart='1', pageEnd='324', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=1, specialIssue=null, createTime=1768286625881, creator=13701087609, updateTime=1768287480278, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1217849218753024879, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1217845635080962613, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1217849218753024880, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1217845635080962613, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=44, endPage=50, ext={EN=ArticleExt(id=1217845646074237699, articleId=1217845645432509146, tenantId=1146029695717560320, journalId=1149652044408987649, language=EN, title=Determination of patulin in rice bran by ultra performance liquid chromatography-tandem mass spectrometry, columnId=1151895322692776479, journalTitle=Journal of Food Safety & Quality, columnName=Special Topic: Analysis and Monitoring of Toxic and Harmful Substances in Food, runingTitle=null, highlight=null, articleAbstract=

Objective To establish a method for determination of patulin in rice bran by ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Methods The patulin from rice bran samples were extracted with ethyl acetate, purified by a solid phase extraction cartridge, eluted with the mobile phase of 0.1% formic acid solution and acetonitrile, separated on the Luna®Omega Polar C18 column (100 mm×2.1 mm, 3 μm), then analyzed in positive and negative ion mode of electrospray ionization source under multiple reaction monitoring mode, quantified by matrix matching curve external standard. Results In the range of 25.0-250.0 μg/L, the peak area of patulin was linearly correlated with the content, and the correlation coefficient (r2) was 0.9993. The limit of detection was 3.0 μg/kg, limit of quantitation was 10.0 μg/kg. Meanwhile, the average recoveries of patulin in rice bran were 86.7%-96.5% with the maximum relative standard deviations of 6.2% at the spiked concentration of 25.0, 50.0, 250.0 μg/kg. Conclusion This study establishes an efficient detection method for patulin in rice bran. This method has high precision and accuracy, and is simple to operate and has high analytical efficiency at the same time. The research results provide technical support for formulating the determination standard of patulin in rice bran and related quality control specifications.

, correspAuthors=Xiu-Qin XU, 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=Xiu-Qin XU, Hao ZHANG, Yong ZHU), CN=ArticleExt(id=1217845647919731637, articleId=1217845645432509146, tenantId=1146029695717560320, journalId=1149652044408987649, language=CN, title=超高效液相色谱-串联质谱法测定米糠中展青霉素, columnId=1151923892102197877, journalTitle=食品安全质量检测学报, columnName=专题：食品中有毒有害物质分析与监测, runingTitle=null, highlight=null, articleAbstract=

目的 建立超高效液相色谱-串联质谱法(ultra performance liquid chromatography-tandem mass spectrometry, UPLC-MS/MS)测定米糠中展青霉素的方法。方法 米糠中的展青霉素用乙酸乙酯提取, 经固相净化柱净化, 以Luna®Omega Polar C18色谱柱(100 mm×2.1 mm, 3 μm)分离, 乙腈-0.1%甲酸水为流动相进行梯度洗脱, 采用电喷雾正、负离子模式采集的多反应监测模式, 进行定性和定量分析。结果 展青霉素在25.0~250.0 μg/L范围内, 峰面积与含量呈线性相关, 相关系数(r2)为0.9993。检出限为3.0 μg/kg, 定量限为10.0 μg/kg。在25.0、50.0、250.0 μg/kg的加标水平下, 展青霉在米糠中的回收率为86.7%~96.5%, 最大相对标准偏差为6.2%。结论 本研究建立了一种米糠中展青霉素的高效检测方法, 该方法具有较高的精密度和准确度, 同时操作简便、分析效率高。研究结果为制定米糠中展青霉素的测定标准及相关质量控制规范提供技术支持。

, correspAuthors=许秀琴, authorNote=null, correspAuthorsNote=
* 许秀琴(1980—), 女, 博士, 高级工程师, 主要研究方向为农产品质量安全。E-mail:
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许秀琴(1980—), 女, 博士, 高级工程师, 主要研究方向为农产品质量安全。E-mail:

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articleId=1217845645432509146, language=EN, orderNo=2, keyword=patulin), Keyword(id=1217864257585201267, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=EN, orderNo=3, keyword=rice bran), Keyword(id=1217864257702641784, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=CN, orderNo=1, keyword=超高效液相色谱-串联质谱法), Keyword(id=1217864257862025347, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=CN, orderNo=2, keyword=展青霉素), Keyword(id=1217864257975271568, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=CN, orderNo=3, keyword=米糠)], refs=[Reference(id=1217864262060523942, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, doi=null, pmid=null, pmcid=null, year=2007, volume=19, issue=2, pageStart=165, pageEnd=166, url=null, language=null, rfNumber=[1], 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Critical Reviews in Analytical Chemistry, 2016, 46(2): 93-105., articleTitle=Biological matrix effects in quantitative tandem mass spectrometry-based analytical methods: Advancing biomonitoring, refAbstract=null), Reference(id=1217864270214251328, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, doi=null, pmid=null, pmcid=null, year=2015, volume=168, issue=null, pageStart=445, pageEnd=453, url=null, language=null, rfNumber=[30], rfOrder=42, authorNames=RAHMAN MM, EL-ATY AMA, CHOI JH, journalName=Food Chemistry, refType=null, unstructuredReference=RAHMAN MM, EL-ATY AMA, CHOI JH, et al. Consequences of the matrix effect on recovery of dinotefuran and its metabolites in green tea during tandem mass spectrometry analysis[J]. 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Analysis and summary of matrix effects in gas chromatography- mass spectrometry (GC-MS) and liquid chromatography- tandem mass spectrometry (LC-MS/MS)[J]. Agrochemicals, 2017, 56(3): 162-167., articleTitle=Analysis and summary of matrix effects in gas chromatography- mass spectrometry (GC-MS) and liquid chromatography- tandem mass spectrometry (LC-MS/MS), refAbstract=null), Reference(id=1217864270570767196, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, doi=null, pmid=null, pmcid=null, year=2003, volume=75, issue=13, pageStart=3019, pageEnd=3030, url=null, language=null, rfNumber=[32], rfOrder=45, authorNames=MATUSZEWSKI BK, CONSTANZER ML, CHAVEZ-ENG CM, journalName=Analytical Chemistry, refType=null, unstructuredReference=MATUSZEWSKI BK, CONSTANZER ML, CHAVEZ-ENG CM. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS[J]. 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Gradient elution procedures

, figureFileSmall=null, figureFileBig=null, tableContent=
时间/min 流速/(mL/min) A/% B/%
0 0.5 97 3
0.2 0.5 97 3
1.0 0.5 20 80
1.5 0.5 2 98
4.0 0.5 2 98
4.1 0.5 97 3
6.0 0.5 97 3
), ArticleFig(id=1217864260823204124, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=CN, label=表1, caption=

梯度洗脱程序

, figureFileSmall=null, figureFileBig=null, tableContent=
时间/min 流速/(mL/min) A/% B/%
0 0.5 97 3
0.2 0.5 97 3
1.0 0.5 20 80
1.5 0.5 2 98
4.0 0.5 2 98
4.1 0.5 97 3
6.0 0.5 97 3
), ArticleFig(id=1217864260944838955, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=EN, label=Table 2, caption=

Recoveries of patulin purified with different solid-phase extraction cartridges (n=6)

, figureFileSmall=null, figureFileBig=null, tableContent=
固相萃取柱 添加质量浓度/(µg/L) 回收率/% RSDs/%
Copure® 228多功能净化柱 200 93 7.8
ProElut PXA混合型强阴离子固相萃取柱 200 55 9.6
Anavo® PWAX 固相萃取柱 200 51 8.0
MAX混合型阴离子交换柱 200 82 8.3
), ArticleFig(id=1217864261045502264, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=CN, label=表2, caption=

展青霉素在不同固相萃取柱中的回收率(n=6)

, figureFileSmall=null, figureFileBig=null, tableContent=
固相萃取柱 添加质量浓度/(µg/L) 回收率/% RSDs/%
Copure® 228多功能净化柱 200 93 7.8
ProElut PXA混合型强阴离子固相萃取柱 200 55 9.6
Anavo® PWAX 固相萃取柱 200 51 8.0
MAX混合型阴离子交换柱 200 82 8.3
), ArticleFig(id=1217864261221663052, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=EN, label=Table 3, caption=

Conditions of MRM

, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 保留时间/min 母离子(m/z) 子离子(m/z) 驻留时间/s 锥孔电压/V 碰撞电压/eV
展青霉素 1.69 154.962 70.926* 0.050 18.0 10.0
展青霉素 1.69 154.962 98.919 0.050 18.0 10.0
展青霉素内标 1.69 159.904 85.964 0.050 -12.0 -6.0
), ArticleFig(id=1217864261343297878, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1217845645432509146, language=CN, label=表3, caption=

MRM条件

, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 保留时间/min 母离子(m/z) 子离子(m/z) 驻留时间/s 锥孔电压/V 碰撞电压/eV
展青霉素 1.69 154.962 70.926* 0.050 18.0 10.0
展青霉素 1.69 154.962 98.919 0.050 18.0 10.0
展青霉素内标 1.69 159.904 85.964 0.050 -12.0 -6.0
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超高效液相色谱-串联质谱法测定米糠中展青霉素
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许秀琴 * , 章豪 , 朱勇
食品安全质量检测学报 | 专题：食品中有毒有害物质分析与监测 2025,16(16): 44-50
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食品安全质量检测学报 | 专题：食品中有毒有害物质分析与监测 2025, 16(16): 44-50
超高效液相色谱-串联质谱法测定米糠中展青霉素
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许秀琴* , 章豪, 朱勇
作者信息
  • 宁波市农业科学研究院, 宁波市特色农产品质量安全检测与控制重点实验室, 宁波 315040

    • 许秀琴(1980—), 女, 博士, 高级工程师, 主要研究方向为农产品质量安全。E-mail:

通讯作者:

* 许秀琴(1980—), 女, 博士, 高级工程师, 主要研究方向为农产品质量安全。E-mail:
Determination of patulin in rice bran by ultra performance liquid chromatography-tandem mass spectrometry
Xiu-Qin XU* , Hao ZHANG, Yong ZHU
Affiliations
  • Ningbo Academy of Agricultural Sciences, Ningbo Key Laboratory of Testing and Control for Characteristic Agro-product Quality and Safety, Ningbo 315040, China
出版时间: 2025-08-25 doi: 10.19812/j.cnki.jfsq11-5956/ts.20250217007
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摘要
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目的 建立超高效液相色谱-串联质谱法(ultra performance liquid chromatography-tandem mass spectrometry, UPLC-MS/MS)测定米糠中展青霉素的方法。方法 米糠中的展青霉素用乙酸乙酯提取, 经固相净化柱净化, 以Luna®Omega Polar C18色谱柱(100 mm×2.1 mm, 3 μm)分离, 乙腈-0.1%甲酸水为流动相进行梯度洗脱, 采用电喷雾正、负离子模式采集的多反应监测模式, 进行定性和定量分析。结果 展青霉素在25.0~250.0 μg/L范围内, 峰面积与含量呈线性相关, 相关系数(r2)为0.9993。检出限为3.0 μg/kg, 定量限为10.0 μg/kg。在25.0、50.0、250.0 μg/kg的加标水平下, 展青霉在米糠中的回收率为86.7%~96.5%, 最大相对标准偏差为6.2%。结论 本研究建立了一种米糠中展青霉素的高效检测方法, 该方法具有较高的精密度和准确度, 同时操作简便、分析效率高。研究结果为制定米糠中展青霉素的测定标准及相关质量控制规范提供技术支持。

超高效液相色谱-串联质谱法  /  展青霉素  /  米糠

Objective To establish a method for determination of patulin in rice bran by ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Methods The patulin from rice bran samples were extracted with ethyl acetate, purified by a solid phase extraction cartridge, eluted with the mobile phase of 0.1% formic acid solution and acetonitrile, separated on the Luna®Omega Polar C18 column (100 mm×2.1 mm, 3 μm), then analyzed in positive and negative ion mode of electrospray ionization source under multiple reaction monitoring mode, quantified by matrix matching curve external standard. Results In the range of 25.0-250.0 μg/L, the peak area of patulin was linearly correlated with the content, and the correlation coefficient (r2) was 0.9993. The limit of detection was 3.0 μg/kg, limit of quantitation was 10.0 μg/kg. Meanwhile, the average recoveries of patulin in rice bran were 86.7%-96.5% with the maximum relative standard deviations of 6.2% at the spiked concentration of 25.0, 50.0, 250.0 μg/kg. Conclusion This study establishes an efficient detection method for patulin in rice bran. This method has high precision and accuracy, and is simple to operate and has high analytical efficiency at the same time. The research results provide technical support for formulating the determination standard of patulin in rice bran and related quality control specifications.

ultra performance liquid chromatography-tandem mass spectrometry  /  patulin  /  rice bran
许秀琴, 章豪, 朱勇. 超高效液相色谱-串联质谱法测定米糠中展青霉素. 食品安全质量检测学报, 2025 , 16 (16) : 44 -50 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20250217007
Xiu-Qin XU, Hao ZHANG, Yong ZHU. Determination of patulin in rice bran by ultra performance liquid chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality, 2025 , 16 (16) : 44 -50 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20250217007
正文
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0 引言
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展青霉素是一种内酯类化合物, 化学名称为4-羟基-4-氢-呋喃[-3,2c]-吡喃-2(6)-酮, 其分子量为154, 分子结构式如图1。
它是由扩展青霉、丝衣霉、曲霉等霉菌产生的多聚乙酰内酯类真菌毒素[1-2], 在免疫、生殖、细胞、致癌等方面均有急性或慢性毒作用[3-6]。另外, 展青霉素还会造成DNA分子交联形成核质桥, 激活有丝分裂蛋白酶原, 导致纺锤体加倍, 从而具有非常强的遗传毒性[7]。同时, 展青霉素还可以在食物链中富集, 严重危害人类的健康。我国现行的GB 2761—2017《食品安全国家标准 食品中真菌毒素限量》, 明确规定果汁、苹果酒、苹果醋中展青霉素的限量为50 μg/kg, 婴幼儿食品中的限量为10 μg/kg。
米糠是由大米加工产生的副产物, 我国每年生产的米糠远超1200万t[8]。米糠中含有90%以上人体必需的维生素、氨基酸和矿物质等, 同时还含有大量的生物活性物质如谷蛋白、植物甾醇、α-生育酚、γ-谷维素、酚酸、黄酮类化合物、生育三烯酚、生物阿魏酸等[9-13]。这些活性物质具有广泛的抗炎、抗氧化、祛斑美白、保湿、抗癌、抗病毒等功能[14], 在食品、饲料、化妆品、医药等领域均具有广泛的应用前景[15-20]。米糠富含淀粉、糖类等营养物质, 这种高营养密度的环境为青霉属等产毒真菌的增殖提供了物质基础且米糠中细菌含量可达每克百万级, 霉菌含量达万级。展青霉素产生菌的最适生长条件为25 ℃、95%湿度, 这与米糠储存中常见的散装堆积导致的局部高温高湿环境高度吻合。此外, 米糠在运输过程中若遭遇通风不良或温度波动, 会进一步加速霉菌代谢活动。因此, 在米糠的生产、运输或储存过程中, 通常会产生展青霉素等生物毒素, 严重危害人类的健康[21-22]。但目前关于检测米糠中展青霉素的研究较少[23]。
目前, 展青霉素常用的检测方法有酶联免疫吸附测定法(enzyme-linked immunosorbent assay, ELISA)、高效液相色谱法(high performance liquid chromatography, HPLC)、高效液相色谱-串联质谱法(high performance liquid chromatography-tandem mass spectrometry, HPLC-MS/MS)、气相色谱法(gas chromatography, GC)、气相色谱-串联质谱法(gas chromatography-tandem mass spectrometry, GC-MS/MS)等。ELISA是基于特异性抗原抗体专一性结合原理的检测方法, 灵敏度较高, 然而展青霉素是一种小分子化合物, 其抗体制备较难, 这从一定程度上限制了免疫分析法在展青霉素检测中的应用[24]; GC及GC-MS/MS用于展青霉素的测定需要先将展青霉素衍生化, 前处理过程比较复杂[25]; HPLC具有选择性好、准确度高的特点, 目前在实验室中的应用也比较普及, 但是HPLC检测所需的前处理过程对展青霉素的稳定性存在一定的影响, 且其检出限要远远低于液相色谱-串联质谱法[26]。近几年, 由于HPLC-MS/MS适用于复杂食品基质中真菌毒素的定性、定量检测, 且仪器的检出限、定量限相对较低, 已被广泛应用于食品中多种真菌毒素的测定[27]。HERRERA等[28]采用多功能柱为净化手段, 同位素稀释液相色谱-串联质谱法来测定水果及其制品中的展青霉素, 获得了较低的定量限和较高的回收率; 我国现行GB 5009.185—2016《食品安全国家标准 食品中展青霉素的测定》, 针对果汁、果泥、山楂片等建立了液相色谱-串联质谱法与HPLC的测定方法。样品经过乙酸乙酯提取、固相净化柱净化、浓缩5倍后上机测定, 液相色谱-串联质谱法最低检出限可达到3.0 μg/kg, 而液相色谱法仅可达到6.0 μg/kg。
鉴于此, 本研究应用乙酸乙酯提取、固相萃取(solid-phase extraction, SPE)净化柱净化后, 超高效液相色谱-串联质谱法(ultra performance liquid chromatography- tandem mass spectrometry, UPLC-MS/MS)进行测定, 以期实现米糠中展青霉素快速定性和精确定量的测定, 为我国制定相关标准提供技术及数据支持。
1 材料与方法
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1.1 试剂与材料
展青霉素标准品、13C7-展青霉素同位素内标标准品(7个C原子被13C同位素取代, 纯度>99%, 上海安普科学仪器公司); 甲酸、乙酸乙酯、乙腈(色谱纯, 美国莫克公司); 冰乙酸(分析纯, 国药集团上海有限公司); 实验用水为Mili-Q超纯水仪所制超纯水。
米糠为市售样品。
1.2 仪器与设备
Acquity UPLC-MS/MS超高效液相色谱串联质谱仪(美国Waters公司); SIGMA3K15离心机(北京博励行有限公司); Mili Q超纯水仪(美国Millipore公司); KS4000ic恒温振荡器、GENIUS3旋涡混合器(德国IKA公司); N-EVAPTM 112氮吹仪(美国Organomation公司); XPE205十万分之一电子天平(瑞士Mettler Toledo公司); Luna®Omega Polar C18色谱柱(100 mm×2.1 mm, 3 μm, 美国飞诺美公司); 展青霉素固相净化柱(Copure® 228多功能净化柱多功能固相净化柱, 北京中检维康生物技术有限公司)。
1.3 实验方法
1.3.1 标准溶液的配制
(1)标准储备液
称取展青霉素、展青霉素内标标准品10.0 mg定容至100 mL, 质量浓度为100 mg/L, 与-18 ℃保存, 保质期为6个月。
准确量取展青霉素、展青霉素内标标准溶液(100.00 mg/L) 0.10 mL用乙腈定容至10.00 mL, 得到质量浓度为1.00 mg/L的标准储备液, 于-18 ℃保存, 保质期为3个月。
(2)标准工作液
用流动相(乙腈:0.1%甲酸水=3:97, V:V)稀释标准储备液1.0 mg/L的展青霉素分别为25.0、50.0、100.0、200.0、250.0 μg/L的标准工作液, 于标准工作液中添加25.0 μg/L展青霉素内标, 现配现用。
1.3.2 样品前处理
(1)样品提取
准确称取1.00 g(精确至0.01 g)米糠样品置于50 mL具塞离心管中, 加入50 μL同位素内标溶液, 静置片刻后, 加入10 mL乙酸乙酯溶液, 涡旋混合5 min, 9500 r/min离心5 min, 移取乙酸乙酯层至100 mL梨型瓶; 再用乙酸乙酯提取一次, 合并两次提取液, 在40 ℃水浴锅中旋转浓缩至干, 以5.0 mL 4%乙酸溶液溶解残留物, 待净化。
(2)样品净化
将提取液加入到固相净化柱中, 将净化柱带橡胶头的一端插入试管, 向下压至试管底端, 净化后的液体通过填料到达净化柱顶端, 将液体倒出, 于40 ℃水浴中氮吹至近干, 用4%乙酸溶液定容至1 mL, 涡旋30 s溶解残留物, 用0.22 μm滤膜过滤, 供HPLC- MS/MS测定。
1.3.3 仪器条件
(1)液相色谱条件
色谱柱Luna®Omega Polar C18色谱柱(100 mm×2.1 mm, 3 μm); 柱温箱温度: 40 ℃; 进样量2 μL, 流动相: 0.1%甲酸水(A)-乙腈(B)(梯度洗脱), 见表1。
(2)质谱条件
检测模式: 多反应监测(multi-reaction monitoring, MRM); 毛细管电压: 3.5 kV; 离子源温度: 150 ℃; 去溶剂温度: 500 ℃; 脱溶剂气流速: 1000 L/Hr; 展青霉素电离方式: 电喷雾电离(electrospray ionization, ESI), 正离子源ESI(+): 展青霉素定量离子对154.962>70.926(碰撞能量:10.0 V, 锥孔电压: 18.0 V); 展青霉素定性离子对154.962>98.919(碰撞能量:10.0 V, 锥孔电压: 18.0 V); 展青霉素内标电离方式: ESI(-), 展青霉素内标定量离子对159.904>85.964(碰撞能量: 12.0 V, 锥孔电压: 6.0 V)。
1.3.4 添加回收实验
准确称取1.00 g样品, 添加2个水平的展青霉素标准物质(分别为25.0、50.0、250.0 μg/kg), 进行提取、净化、每个添加水平进行3次重复, 进行定量分析, 分别计算回收率和相对标准偏差(relative standard deviation, RSD)。
1.4 数据处理
采用Masslynx 4.1软件直接处理分析检测数据并导出结果。采用WPS 2019进行标准曲线拟合和数据整理。
2 结果与分析
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2.1 样品前处理过程的优化
2.1.1 提取溶剂的选择
展青霉素是一种中性物质, 易溶于水、乙醇、丙酮、乙酸乙酯和氯仿, 微溶于乙醚和苯, 不溶于石油醚。米糠样品基质中含有蛋白质、脂肪、糖分、矿物质等, 基质非常复杂, 在样品的前处理过程中, 提取溶剂的选择对于展青霉素的测定至关重要。根据相关研究[25-28], 展青霉素的提取试剂主要为乙酸乙酯、乙腈、丙酮等。本研究考察了甲醇、乙腈、水、乙醇、丙酮、乙酸乙酯对展青霉素的提取效果, 其3次重复实验平均回收率如图2所示。实验结果表明, 提取溶剂的选择对展青霉素的回收率影响非常显著。以乙酸乙酯为提取液, 提取杂质较少, 且容易过柱, 回收率最高, 为95%; 其次以乙腈为提取液, 回收率也较高, 为81%。因为乙腈和水互溶, 需要先在米糠样品中添加纯净水, 乙腈提取后经过盐析分离水分, 这种前处理方法提取后杂质较多; 以甲醇、水、乙醇、丙酮作为提取试剂, 展青霉素的回收率均不高, 为40%~70%之间。展青霉素虽然易溶于甲醇、水、乙醇、丙酮, 但是由于其分子结构中的内酯环, 在酸性条件下稳定而在中性和碱性条件下容易分解。所以用甲醇、水、乙醇、丙酮提取展青霉素, 会由于展青霉素的不稳定性而导致回收率降低。最终选择乙酸乙酯为提取溶剂。
2.1.2 固相净化柱的选择
取1.0 mg/L的展青霉素的标准溶液1.0 mL, 用5 mL乙酸溶液稀释后考察展青霉素在不同净化柱中的净化效果。选取几种不同类型的阴离子固相净化柱(Copure® 228多功能净化柱、ProElut PXA混合型强阴离子固相萃取柱、Anavo® PWAX固相萃取柱、MAX混合型阴离子交换柱)进行净化, 按照1.3.2(1)进行提取, 1.3.2(2)进行净化, 净化后的回收率见表2。
Copure® 228是混合型多功能净化柱, 适用于中等极性或非极性化合物的净化, 可一步法去除米糠基质中的脂肪、蛋白质等物质, 净化后可显著降低基质干扰, 色谱图背景干净, 加标回收率最高, 可达93%, 效果最好; ProElut PXA属于混合型弱阴离子交换反相柱, 常用于酸性化合物, 而展青霉素在溶液中表现为中性分子, 只有在特定的碱性条件下解离为阴离子, 故虽然ProElut PXA的pH耐受性较宽, 且兼容酸性或碱性样品, 然而在净化展青霉素的表现中, 回收率较低, 仅为55%; Anavo® PWAX固相萃取柱属于弱阴离子交换柱, 适用于弱酸性化合物的净化, 而展青霉素不属于弱酸性化合物, 所以该小柱表现出了较低的回收率, 回收率仅为51%; MAX混合型阴离子交换柱具有较高的交换容量和极端的pH耐受性, 稳定性强。该小柱属于强阴离子交换柱, 在展青霉素的净化过程中表现一般, 回收率为82%。研究结果表明, 应用Copure® 228多功能净化柱净化米糠基质中的展青霉素, 回收率最高, 效果最好, 故选择Copure® 228多功能净化柱进行实验。
2.1.3 样品稳定性
展青霉素在酸性条件下非常稳定, 而在碱性条件下易发生水解或开环反应, 导致分子结构破坏。乙酸乙酯作为极性有机溶剂, 能够有效溶解展青霉素的分子结构, 同时其酸性环境有助于维持展青霉素的化学稳定性。本研究对提取净化后的样品稳定性进行了探索, 研究结果发现, 展青霉素在乙酸溶液中的化学稳定性较好, 在提取、净化过程中是否避光对结果影响不大, 进样溶液于15 ℃下放置12 h后, 展青霉素及其内标降解率小于5%。
2.2 基质效应
在UPLC-MS/MS检测过程中, 样品中的非挥发性组分和待测目标离子通过色谱柱后, 通过喷雾针进入质谱仪, 对电荷产生竞争, 使得待测目标离子电离数量减少, 同时阻碍雾滴分裂, 产生离子抑制效应。所以, 在液相色谱-串联质谱分析中, 相同含量的目标分析物, 在基质中的响应要低于纯溶剂中的响应, 表现为基质减弱效应[29]。基质效应产生的因素复杂, 且与目标物的化学性质密切相关[30]。有研究表明, 当目标分析物中含有-OH、P=O、-N=、-O-CO-NH-等特定功能团时, 该目标化合物的基质效应比较明显[31], 而展青霉素的分子结构中含有-OH功能团, 理论上会在测定过程中产生较强的基质效应。本研究采用固相萃取柱净化以消除或降低基质效应。以空白米糠样品为基质, 采取样品提取后应用标准加入法来评价基质效应[32], 即样品经过乙酸乙酯提取, 净化柱净化后, 加入展青霉素及其同位素标准溶液。展青霉素及其同位素的基质效应因子(matrix factor, MF)以其在基质中与在溶剂中的响应峰峰面积的比值来表示。展青霉素的基质效应因子与其同位素的基质效应因子的比值被称为内标归一化基质效应因子, 因为展青霉素及其同位素的绝对基质效应相近, 可用两者基质效应的比值来抵消展青霉素的基质效应。其变异系数(variable coefficient, CV)[32]是样品中内标归一化基质效应因子的相对标准偏差, 用于评价在样品中采用同位素内标校正基质效应的准确性, CV越小说明基质对结果准确度影响较小, 方法越可靠。本研究中CV为4.1%, 小于15%, 符合欧洲药品管理局指导原则[32]的规定, 因此该方法适合米糠样品中展青霉素的测定, 其基质干扰可用同位素内标来校正。
2.3 仪器条件优化
分别对质量浓度为1.0 mg/L的展青霉素及其内标进行全扫描。用针泵直接进样, 在ESI正负电离模式下对展青霉素及其内标标准溶液进行MS全扫描分析, 找到其母离子。结果表明, 在正离子模式下, 展青霉素能够获得较高强度的[M+H]分子离子峰, 而展青霉素内标在ESI负离子模式下有较高的分子离子峰响应值。同步优化离子源温度、锥孔电压、脱溶剂气温度、脱溶剂气流速、毛细管电压等参数, 最终确定离子源温度为150 ℃、去溶剂温度为500 ℃、脱溶剂气流速为1000 L/Hr、锥孔电压为18 V。在20 eV 碰撞能量下, 对碎片离子进行二级质谱扫描, 选择丰度较高的两个碎片离子分别作为定性和定量离子, 并优化相应的碰撞能, 使仪器的灵敏度、稳定性处于最佳状态, 质谱条件见表3。在优化完质谱方法后, 对液相方法进行优化。在0.1%甲酸-甲醇体系中, 展青霉素及其内标在正、负离子模式下的响应均较低, 而在0.1%甲酸-乙腈体系中, 这两种物质均获得了良好的响应。这是因为在Polar C18色谱柱中, 展青霉素及其内标更容易被乙腈洗脱而得到良好的响应。最终, 本研究选择0.1%甲酸-乙腈作为流动相, 最终梯度洗脱程序见表1。
2.4 定性与定量分析
选择50 µg/L展青霉素标准溶液与25 µg/L同位素内标(13C7-展青霉素), 采用表1的流动相进行梯度洗脱, 得到的展青霉素及其内标色谱图见图3。如图3所示, 展青霉素在Luna®Omega Polar C18色谱柱上的保留时间为1.69 min, 表现出快速洗脱特性。这是由于展青霉素是极性较大的小分子化合物且含多个羟基和羰基, 导致在反相色谱柱中的保留能力较弱, 易受基质干扰而出现基线波动。然而, 其同位素内标采用ESI(-)模式检测, 有效地降低了基质效应, 使内标基线平稳性显著优于目标物。针对米糠基质样品(加标浓度100 µg/kg), 经Copure® 228固相萃取柱净化后, 得到加标样品的色谱图, 见图4。由图4可知, 目标物在1.68 min出峰, 其保留时间与标准溶液高度吻合, 表明前处理方法有效去除了米糠中复杂的脂类及色素干扰。实验结果显示, 加标样品谱图中杂峰响应值低, 方法灵敏度高, 回收率较好, 特别适用于高色素、高油脂的米糠基质分析。
2.5 方法学考察
2.5.1 检出限、定量限和线性范围
在空白米糠样品中添加3.0 μg/kg的展青霉素标准品进行检测, 由谱图计算信噪比, 以3倍信噪比和10倍信噪比确定仪器的检出限(limit of detection, LOD)和定量限(limit of quantitation, LOQ)。根据谱图的信噪比, 确定检出限为3.0 μg/kg, 定量限为10.0 μg/kg。应用25.0、50.0、100.0、200.0、250.0 μg/L的展青霉素的标准溶液做标准曲线溶液, 外标法定量。以展青霉素的峰面积和展青霉素内标峰面积的比值为纵坐标(Y), 以展青霉素的质量浓度为横坐标(X, μg/L), 绘制标准曲线, 其相应的回归方程为Y=1.78453X+8.75172, 相关系数r2=0.9993。表明展青霉素质量浓度在25.0~250.0 μg/L范围内线性关系良好。
2.5.2 准确度和精密度
采用加标回收的方法来验证实验的准确度和精密度。准确称取1.00 g样品, 添加3个水平的展青霉素标准物质(分别为25.0、50.0、250.0 μg/kg), 进行提取、净化、每个添加水平平行测定2次, 每个浓度重复进样3次, 进行定量分析, 平均回收率范围在86.7%~96.5%之间, 精密度CV在1.3%~6.2%之间, 准确度高, 重复性好, 满足实验要求。
2.6 实际样品的检测
采用本研究建立的方法, 对市场购买的20批次米糠样品进行筛查分析。检测结果显示, 有5批次米糠样品检出展青霉素, 含量为3.6~980.0 μg/kg之间; 其余批次样品均未检出。为验证本方法的可靠性, 采用GB 5009.185— 2016对这20批次米糠样品进行验证, 测得的展青霉素含量为3.2%~920%之间, 所得结果稍低于本研究所得结果, 两者的相对标准偏差为6.3%~11.8%之间。因此, 本研究建立的方法较国标法更加准确、方便、省时、回收率更高。
3 结论
收起
本研究通过系统优化前处理条件, 建立了基于同位素内标校正的米糠中展青霉素检测新方法。在提取溶剂筛选中发现, 传统乙腈提取法存在基质干扰明显、操作流程烦琐等局限性, 而乙酸乙酯因其与目标物中性特征的适配性, 既可避免酸性条件下的分解风险, 又能实现更优的提取效率, 最终获得95%的回收率。针对米糠基质复杂性, 创新性采用Copure® 228多功能净化柱替代常规ProElut PXA阴离子交换柱, 通过特异性吸附作用将基质干扰降低至可接受水平, 使净化回收率提升至93%。方法学验证表明, 同位素内标校正策略可将基质效应CV有效控制在4.1%以内, 显著提升了方法抗干扰能力。与现行国标方法相比, 本方法在检测灵敏度、准确度和操作便捷性等方面均展现出显著优势。特别值得关注的是, 该方法对复杂基质的强适应性, 为拓展应用于谷物、饲料及农产品等多样化基质的真菌毒素检测提供了新思路。另外, 后续可开展展青霉素在不同储存条件下(温湿度、时间梯度)的稳定性研究, 为建立科学规范的样品保存方案提供理论依据。本研究不仅完善了米糠基质中展青霉素的检测技术体系, 更为相关食品安全标准的修订提供了可靠的技术支撑。
基金
收起
  • 宁波市科技特派员项目(2024S205)
  • 宁波市公益性研究计划项目(2024S011)
文献
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2025年第16卷第16期
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doi: 10.19812/j.cnki.jfsq11-5956/ts.20250217007
  • 接收时间：2025-02-17
  • 首发时间：2026-01-13
  • 出版时间：2025-08-25
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  • 收稿日期：2025-02-17
基金
宁波市科技特派员项目(2024S205)
宁波市公益性研究计划项目(2024S011)
作者信息
    宁波市农业科学研究院, 宁波市特色农产品质量安全检测与控制重点实验室, 宁波 315040

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* 许秀琴(1980—), 女, 博士, 高级工程师, 主要研究方向为农产品质量安全。E-mail:
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2种不同金属材料的力学参数
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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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