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Article(id=1153986648326001184, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153986642063905290, articleNumber=null, orderNo=null, doi=10.19812/j.cnki.jfsq11-5956/ts.20240902001, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1725206400000, receivedDateStr=2024-09-02, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1753061456996, onlineDateStr=2025-07-21, pubDate=1739548800000, pubDateStr=2025-02-15, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1753061456996, onlineIssueDateStr=2025-07-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1753061456996, creator=13701087609, updateTime=1753061456996, updator=13701087609, issue=Issue{id=1153986642063905290, tenantId=1146029695717560320, journalId=1149652044408987649, year='2025', volume='16', issue='3', pageStart='1', pageEnd='316', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=0, createTime=1753061455502, creator=13701087609, updateTime=1760070725729, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1183385652272968023, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153986642063905290, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1183385652272968024, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153986642063905290, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=169, endPage=175, ext={EN=ArticleExt(id=1153986648766403106, articleId=1153986648326001184, tenantId=1146029695717560320, journalId=1149652044408987649, language=EN, title=Determination of advanced glycation end products and 5-hydroxymethylfurfural in loquat fruit paste by high performance liquid chromatography-tandem mass spectrometry, columnId=1153433635433730748, journalTitle=Journal of Food Safety & Quality, columnName=Special Topic: Comprehensive Utilization and Quality Safety of Agricultural Products, runingTitle=null, highlight=null, articleAbstract=

Objective To establish a method for the determination of advanced glycation end products (AGEs) and 5-hydroxymethylfurfural (5-HMF) in loquat fruit paste by high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). Methods AGEs solution was obtained by extracting loquat fruit paste with pure water and treating with ultrasonic, centrifugation, solid-phase extraction and ammonia methanol solution elution, then separated by using gradient elution with 0.1% formic acid in water and methanol as the mobile phase. The detection method employed multi-reaction monitoring with positive ion. The 5-HMF solution was obtained by extracting the fruit paste in pure water, followed a liquid-liquid extraction with ethyl acetate, solid-phase extraction and 10% methanol elution. The extracts were analyzed at 30 ℃ with 10% methanol in water as mobile phase. Results It was found that the linearity of all the targets was good in the concentration range. The limits of detection and limits of quantification of each target substance were lower than 1 [AGEs/(ng/mL); 5-HMF/(µg/mL)], which could fulfill the requirements of detecting trace substances. The relative standard deviations (RSDs) of all the substances were less than 10%, and lower than 0.6% in the range of 16 hours of sample waiting time. The recoveries of all the substances were higher than 85%. Conclusion Results indicate that the method meet the basic requirement for quantitative analysis and has good accuracy and stability, which offers a detection means of studying on quality and safety of heat-processed fruit and vegetables.

, correspAuthors=Sheng-Min LU, 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=Zi-Xin HUANG, Yang TAO, Yong-Bin HAN, Sheng-Min LU), CN=ArticleExt(id=1153986678873117056, articleId=1153986648326001184, tenantId=1146029695717560320, journalId=1149652044408987649, language=CN, title=高效液相色谱-串联质谱法测定枇杷果膏中晚期糖基化终末产物和5-羟甲基糠醛, columnId=1153433635601502912, journalTitle=食品安全质量检测学报, columnName=本期专题：农产品综合利用及质量安全, runingTitle=null, highlight=null, articleAbstract=

目的 建立高效液相色谱-串联质谱法(high performance liquid chromatography-tandem mass spectrometer, HPLC-MS/MS)检测果膏中晚期糖基化终末产物(advanced glycation end products, AGEs)和5-羟甲基糠醛(5-hydroxymethylfurfural, 5-HMF)的方法。方法 枇杷果膏以纯水浸提、超声处理后, 再经离心、固相萃取、氨水-甲醇溶液洗脱得到AGEs提取液, 以0.1%甲酸水和甲醇为流动相, 梯度洗脱, 采用多反应监测正离子源模式检测; 果膏经纯水浸提、乙酸乙酯提取、固相萃取、10%甲醇洗脱得到5-HMF提取液, 以体积比10%甲醇水为流动相, 在柱温30 ℃下检测。结果 3种目标物在浓度范围内均线性关系良好; 检出限和定量限均小于1 [AGEs/(ng/mL); 5-HMF/(µg/mL)], 可满足痕量物质的检测要求; 相对标准偏差(relative standard deviations, RSDs)均小于10%, 且在16 h样品待测时间范围内低于0.6%; 加标回收率均大于85%。结论 本研究优化的方法可满足定量分析的基本要求, 具有良好的准确性和稳定性, 为热加工果蔬产品质量与安全研究提供了检测手段。

, correspAuthors=陆胜民, authorNote=null, correspAuthorsNote=
* 陆胜民(1969—), 男, 博士, 研究员, 主要研究方向为果品加工质量与安全控制。E-mail:
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黄子馨(2001—), 女, 硕士研究生, 主要研究方向为食品安全检测。E-mail:

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黄子馨(2001—), 女, 硕士研究生, 主要研究方向为食品安全检测。E-mail:

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黄子馨(2001—), 女, 硕士研究生, 主要研究方向为食品安全检测。E-mail:

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Food Chemistry, 2024, 447: 138930., articleTitle=Simultaneous determination of advanced glycation end products and heterocyclic amines in roast/grilled meat by UPLC-MS/MS, refAbstract=null), Reference(id=1183428191596200701, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, doi=null, pmid=null, pmcid=null, year=2023, volume=48, issue=12, pageStart=281, pageEnd=289, url=null, language=null, rfNumber=[27], rfOrder=31, authorNames=周海鹏, 岳振峰, 赵凤娟, journalName=食品科技, refType=null, unstructuredReference=周海鹏, 岳振峰, 赵凤娟. 兽药残留检测技术最新进展[J]. 食品科技, 2023, 48(12): 281-289., articleTitle=兽药残留检测技术最新进展, refAbstract=null), Reference(id=1183428191763972862, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, doi=null, pmid=null, pmcid=null, year=2023, volume=48, issue=12, pageStart=281, pageEnd=289, url=null, language=null, rfNumber=[27], rfOrder=32, authorNames=ZHOU HP, YUE ZF, ZHAO FJ, journalName=Food Science and Technology, refType=null, unstructuredReference=ZHOU HP, YUE ZF, ZHAO FJ. The latest development of veterinary drug residues detection technology[J]. Food Science and Technology, 2023, 48(12): 281-289., articleTitle=The latest development of veterinary drug residues detection technology, refAbstract=null), Reference(id=1183428191852053247, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, doi=null, pmid=null, pmcid=null, year=2022, volume=385, issue=null, pageStart=132697, pageEnd=null, url=null, language=null, rfNumber=[28], rfOrder=33, authorNames=CHEN Q, LI Y, DONG LZ, journalName=Food Chemistry, refType=null, unstructuredReference=CHEN Q, LI Y, DONG LZ, et al. Quantitative determination of Nε-(carboxymethyl)lysine in sterilized milk by isotope dilution UPLC-MS/MS method without derivatization and ion pair reagents[J]. Food Chemistry, 2022, 385: 132697., articleTitle=Quantitative determination of Nε-(carboxymethyl)lysine in sterilized milk by isotope dilution UPLC-MS/MS method without derivatization and ion pair reagents, refAbstract=null), Reference(id=1183428191944327936, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, doi=null, pmid=null, pmcid=null, year=2016, volume=37, issue=22, pageStart=90, pageEnd=93, url=null, language=null, rfNumber=[29], rfOrder=34, authorNames=刘慧琳, 穆琳, 陈晓默, journalName=食品工业科技, refType=null, unstructuredReference=刘慧琳, 穆琳, 陈晓默, 等. 固相萃取-高效液相色谱法检测食品中吡咯素的研究[J]. 食品工业科技, 2016, 37(22): 90-93, 102., articleTitle=固相萃取-高效液相色谱法检测食品中吡咯素的研究, refAbstract=null), Reference(id=1183428192032408321, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, doi=null, pmid=null, pmcid=null, year=2016, volume=37, issue=22, pageStart=90, pageEnd=93, url=null, language=null, rfNumber=[29], rfOrder=35, authorNames=LIU HL, MU L, CHEN XM, journalName=Science and Technology of Food Industry, refType=null, unstructuredReference=LIU HL, MU L, CHEN XM, et al. Determination of trace pyrraline in food samples using solid phase extraction and high performance liquid chromatography[J]. Science and Technology of Food Industry, 2016, 37(22): 90-93, 102., articleTitle=Determination of trace pyrraline in food samples using solid phase extraction and high performance liquid chromatography, refAbstract=null), Reference(id=1183428192145654530, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, doi=null, pmid=null, pmcid=null, year=2023, volume=201, issue=null, pageStart=106004, pageEnd=null, url=null, language=null, rfNumber=[30], rfOrder=36, authorNames=BARROSO TLCT, SGANZERLA WG, CASTRO LEN, journalName=Journal of Supercritical Fluids, refType=null, unstructuredReference=BARROSO TLCT, SGANZERLA WG, CASTRO LEN, et al. Removal of 5-hydroxymethylfurfural from brewer's spent grains hydrolysates obtained by subcritical water hydrolysis: An approach using liquid-liquid extraction[J]. 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注: 流速0.40 mL/min, 进样量2 µL。

, figureFileSmall=40SZPFHqwtO7Tckx/QJJKw==, figureFileBig=9ep7tKGht1wuymWECEPiJQ==, tableContent=null), ArticleFig(id=1183428187812938450, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=EN, label=Fig.3, caption=HPLC chromatogram of 5-HMF, figureFileSmall=ZUwMK05bM+er30W4/xT/LQ==, figureFileBig=L7bpxpZXahCShqYr/LIRCg==, tableContent=null), ArticleFig(id=1183428187896824531, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=CN, label=图3, caption=5-HMF的HPLC色谱图

注: 流速1.00 mL/min, 进样量10 µL。

, figureFileSmall=ZUwMK05bM+er30W4/xT/LQ==, figureFileBig=L7bpxpZXahCShqYr/LIRCg==, tableContent=null), ArticleFig(id=1183428187980710612, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=EN, label=Fig.4, caption=Effects of eluent concentration on content of AGEs extracted by SPE from loquat fruit paste (n=3), figureFileSmall=loiA/25MQooc7f+qXXKGPg==, figureFileBig=e6jwlSK30SNxsj0PT7dTew==, tableContent=null), ArticleFig(id=1183428188123316949, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=CN, label=图4, caption=洗脱液浓度对SPE枇杷果膏中AGEs含量的影响(n=3), figureFileSmall=loiA/25MQooc7f+qXXKGPg==, figureFileBig=e6jwlSK30SNxsj0PT7dTew==, tableContent=null), ArticleFig(id=1183428188186231510, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=EN, label=Fig.5, caption=Effects of solution ratio of sample to extractant on content of 5-HMF extracted by solid-liquid extraction from loquat fruit paste (n=3), figureFileSmall=09+DjwAo6BoGGMfjSxwgiA==, figureFileBig=V24nXCvvUxjcJh6eWHfXrQ==, tableContent=null), ArticleFig(id=1183428188274311895, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=CN, label=图5, caption=液液比对固液萃取枇杷果膏中5-HMF的影响(n=3), figureFileSmall=09+DjwAo6BoGGMfjSxwgiA==, figureFileBig=V24nXCvvUxjcJh6eWHfXrQ==, tableContent=null), ArticleFig(id=1183428188333032152, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=EN, label=Table 1, caption=

Linear ranges, linear regression equations and correlation coefficients (r2) of 3 kinds of hazardous substances

, figureFileSmall=null, figureFileBig=null, tableContent=
危害物 线性范围 回归方程 r2
CML 5.00~2500.00 ng/mL Y=3579.76508X+1583.81934 0.99999
CEL 5.00~2500.00 ng/mL Y=5226.58057X-672.78032 0.99928
5-HMF 0.25~5.00 µg/mL Y=15301.9X 0.99910
), ArticleFig(id=1183428188404335321, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=CN, label=表1, caption=

3种危害物的线性范围、线性回归方程和相关系数(r2)

, figureFileSmall=null, figureFileBig=null, tableContent=
危害物 线性范围 回归方程 r2
CML 5.00~2500.00 ng/mL Y=3579.76508X+1583.81934 0.99999
CEL 5.00~2500.00 ng/mL Y=5226.58057X-672.78032 0.99928
5-HMF 0.25~5.00 µg/mL Y=15301.9X 0.99910
), ArticleFig(id=1183428188492415706, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=EN, label=Table 2, caption=

LOD and LOQ of 3 kinds of hazardous substances (n=3)

, figureFileSmall=null, figureFileBig=null, tableContent=
危害物 LODs LOQs
CML 0.159 ng/mL 0.531 ng/mL
CEL 0.113 ng/mL 0.378 ng/mL
5-HMF 0.010 µg/mL 0.040 µg/mL
), ArticleFig(id=1183428188563718875, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153986648326001184, language=CN, label=表2, caption=

3种危害物的LODs和LOQs (n=3)

, figureFileSmall=null, figureFileBig=null, tableContent=
危害物 LODs LOQs
CML 0.159 ng/mL 0.531 ng/mL
CEL 0.113 ng/mL 0.378 ng/mL
5-HMF 0.010 µg/mL 0.040 µg/mL
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高效液相色谱-串联质谱法测定枇杷果膏中晚期糖基化终末产物和5-羟甲基糠醛
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黄子馨 1, 2 , 陶阳 1 , 韩永斌 1 , 陆胜民 1, 2, *
食品安全质量检测学报 | 本期专题：农产品综合利用及质量安全 2025,16(3): 169-175
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食品安全质量检测学报 | 本期专题：农产品综合利用及质量安全 2025, 16(3): 169-175
高效液相色谱-串联质谱法测定枇杷果膏中晚期糖基化终末产物和5-羟甲基糠醛
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黄子馨1, 2 , 陶阳1, 韩永斌1, 陆胜民1, 2, *
作者信息
  • 1.南京农业大学食品科技学院, 南京 210095
  • 2.浙江省农业科学院食品科学研究所, 农产品质量安全危害因子与风险防控国家重点实验室, 杭州 310021

    • 黄子馨(2001—), 女, 硕士研究生, 主要研究方向为食品安全检测。E-mail:

通讯作者:

* 陆胜民(1969—), 男, 博士, 研究员, 主要研究方向为果品加工质量与安全控制。E-mail:
Determination of advanced glycation end products and 5-hydroxymethylfurfural in loquat fruit paste by high performance liquid chromatography-tandem mass spectrometry
Zi-Xin HUANG1, 2 , Yang TAO1, Yong-Bin HAN1, Sheng-Min LU1, 2, *
Affiliations
  • 1. College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China
  • 2. State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products, Institute of Food Science, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, China
出版时间: 2025-02-15 doi: 10.19812/j.cnki.jfsq11-5956/ts.20240902001
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摘要
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目的 建立高效液相色谱-串联质谱法(high performance liquid chromatography-tandem mass spectrometer, HPLC-MS/MS)检测果膏中晚期糖基化终末产物(advanced glycation end products, AGEs)和5-羟甲基糠醛(5-hydroxymethylfurfural, 5-HMF)的方法。方法 枇杷果膏以纯水浸提、超声处理后, 再经离心、固相萃取、氨水-甲醇溶液洗脱得到AGEs提取液, 以0.1%甲酸水和甲醇为流动相, 梯度洗脱, 采用多反应监测正离子源模式检测; 果膏经纯水浸提、乙酸乙酯提取、固相萃取、10%甲醇洗脱得到5-HMF提取液, 以体积比10%甲醇水为流动相, 在柱温30 ℃下检测。结果 3种目标物在浓度范围内均线性关系良好; 检出限和定量限均小于1 [AGEs/(ng/mL); 5-HMF/(µg/mL)], 可满足痕量物质的检测要求; 相对标准偏差(relative standard deviations, RSDs)均小于10%, 且在16 h样品待测时间范围内低于0.6%; 加标回收率均大于85%。结论 本研究优化的方法可满足定量分析的基本要求, 具有良好的准确性和稳定性, 为热加工果蔬产品质量与安全研究提供了检测手段。

枇杷果膏  /  晚期糖基化终末产物  /  5-羟甲基糠醛  /  高效液相色谱-串联质谱法  /  高效液相色谱法

Objective To establish a method for the determination of advanced glycation end products (AGEs) and 5-hydroxymethylfurfural (5-HMF) in loquat fruit paste by high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). Methods AGEs solution was obtained by extracting loquat fruit paste with pure water and treating with ultrasonic, centrifugation, solid-phase extraction and ammonia methanol solution elution, then separated by using gradient elution with 0.1% formic acid in water and methanol as the mobile phase. The detection method employed multi-reaction monitoring with positive ion. The 5-HMF solution was obtained by extracting the fruit paste in pure water, followed a liquid-liquid extraction with ethyl acetate, solid-phase extraction and 10% methanol elution. The extracts were analyzed at 30 ℃ with 10% methanol in water as mobile phase. Results It was found that the linearity of all the targets was good in the concentration range. The limits of detection and limits of quantification of each target substance were lower than 1 [AGEs/(ng/mL); 5-HMF/(µg/mL)], which could fulfill the requirements of detecting trace substances. The relative standard deviations (RSDs) of all the substances were less than 10%, and lower than 0.6% in the range of 16 hours of sample waiting time. The recoveries of all the substances were higher than 85%. Conclusion Results indicate that the method meet the basic requirement for quantitative analysis and has good accuracy and stability, which offers a detection means of studying on quality and safety of heat-processed fruit and vegetables.

loquat fruit paste  /  advanced glycation end products  /  5-hydroxymethylfurfural  /  high performance liquid chromatography-tandem mass spectrometry  /  high performance liquid chromatography
黄子馨, 陶阳, 韩永斌, 陆胜民. 高效液相色谱-串联质谱法测定枇杷果膏中晚期糖基化终末产物和5-羟甲基糠醛. 食品安全质量检测学报, 2025 , 16 (3) : 169 -175 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20240902001
Zi-Xin HUANG, Yang TAO, Yong-Bin HAN, Sheng-Min LU. Determination of advanced glycation end products and 5-hydroxymethylfurfural in loquat fruit paste by high performance liquid chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality, 2025 , 16 (3) : 169 -175 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20240902001
正文
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0 引言
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枇杷肉质细腻、清甜可口, 含有多酚类、黄酮类、皂苷类、三萜类等化合物[1], 具有抗炎、镇咳、止喘、化痰、抗肿瘤和增强机体免疫力等功效, 是一种食药同源型水果[2]。枇杷果膏是一种由枇杷鲜果榨汁浓缩制成的口感酸甜、香气清新的膏状饮品, 具有润肺清热、化痰止咳的功效[3]。果汁中含有的氨基酸、蛋白质等氨基化合物和还原糖等羰基化合物在高温浓缩过程中会发生美拉德反应和焦糖化反应, 在赋予果膏独特风味的同时, 也会产生甲基咪唑[4]、晚期糖基化终末产物(advanced glycation end products, AGEs)[5]、5-羟甲基糠醛(5-hydroxymethylfurfural, 5-HMF)[6]等热加工伴生危害物。AGEs作为非酶蛋白质和脂质糖基化以及脂质氧化的终产物, 包括羧甲基赖氨酸(Nε-carboxymethyl-lysine, CML)、羧乙基赖氨酸(Nε-carboxyethyl-lysine, CEL)、吡咯素和戊糖素等。前二者是研究最为广泛的AGEs, 通常被用作人体和食品中AGEs的标记物[7-8]。研究表明, AGEs的过度积累与机体炎症、动脉粥样硬化、神经退行性病变和糖尿病并发症的发生高度相关[9-11]。此外, 摄入过多外源性AGEs会诱导产生内源性AGEs[12]。而5-HMF摄入体内会被代谢转换成具有毒性、致癌和致突变作用的5-磺基氧甲基糠醛(5-sulfooxymethylfurfural, 5-SMF)[13]。5-SMF的磺酸基是一种良好的离去基团, 它会加速5-SMF与DNA之间的亲核加成反应, 生成加合产物, 进而对人体健康造成威胁[14]。
目前, 食品中AGEs的检测方法按照原理的不同可分为荧光光谱分析法、免疫分析法和色谱-串联质谱法。其中, 荧光光谱分析法能检测具有荧光特性的AGEs, 如戊糖素等, 方法简便易行, 但对缺乏荧光特性的CML、CEL、吡咯素等的测定具有局限性。免疫分析法具有简便快速的优点, 但现有的研究表明该法更适用于AGEs含量较高的液体样品的测定[15], 对食品样品的检测不具备普适性, 且食品基质中的脂质和淀粉等都会对检测结果造成影响[16]。食品中5-HMF最常用的检测方法包括分光光度法[17-18]、高效液相色谱-串联质谱法(high performance liquid chromatography-tandem mass spectrometer, HPLC-MS/ MS)[19-20]和气相色谱-质谱法[21]。与色谱法相比, 分光光度法具有成本低、时间短、操作简单的优势, 但色谱分析法的选择性更好, 检测灵敏度更高, 更适用于痕量样品的检测。
目前国内外有关AGEs的检测大多集中于鱼、肉、烘焙食品、调味品、咖啡、奶制品等产品, 而对于果膏、果酱、浓缩果汁等水果制品中AGEs和5-HMF的检测研究较少, 方法仍不完善。本研究拟建立枇杷果膏中AGEs和5-HMF的提取、分离、纯化及检测方法, 为开展热浓缩型或干制果蔬制品中AGEs和5-HMF的分析测定提供参考, 满足产品质量与安全管理的需要。
1 材料与方法
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1.1 材料、试剂与仪器
大红袍枇杷: 浙江省杭州市临平区塘栖镇枇杷基地提供。
纤维素酶(30000 U/g)、果胶酶(20000 U/g)(河南万邦化工科技有限公司); 白砂糖(太古糖业有限公司); 5-HMF(色谱纯, 纯度≥99.0%, 上海源叶生物科技有限公司); 甲醇(色谱纯, 纯度≥99.9%)、氨水(25%~28%)(上海麦克林生化科技股份有限公司); 乙酸乙酯(色谱纯, 纯度≥99.0%, 美国Sigma-Aldrich公司); 甲酸(色谱纯, 纯度≥99.0%, 美国Thermo Fisher Scientific公司); 娃哈哈纯净水(杭州娃哈哈集团有限公司); CML(纯度≥97.0%)、CEL(纯度≥96.0%)(加拿大TRC公司)。
FE28 pH计、Quick-Brix 90手持式折光仪(Mettler Toledo仪器上海有限公司); DK-500S型水浴锅(上海精宏试验设备有限公司); JYZ-V907榨汁机(九阳股份有限公司); C21-L85电磁灶(杭州九阳生活电器有限公司); KQ-500DB数控超声波清洗器(昆山市超声仪器有限公司); MCX、HLB固相萃取(solid phase extraction, SPE)小柱(常德比克曼生物科技有限公司); SHZ-D(Ⅲ)循环水式多用真空泵(上海秋佐科学仪器有限公司); MD200-1氮吹仪(杭州奥盛仪器有限公司); 0.22 μm水系微孔滤膜过滤器(杭州欧翼仪器设备有限公司); 0.22 μm有机系微孔滤膜过滤器(兰杰柯科技有限公司); 1 mL无菌注射器(镇江康利医疗器械有限公司); Megafuge 11R台式离心机(Thermo Fisher Scientific中国有限公司); XH-C旋涡混合器、LC-2030C 3D Plus高效液相色谱仪(日本Shimadzu公司); Sun Fire C18色谱柱(250 mm× 4.6 mm, 5 µm, 美国Waters公司); RE-52AA旋转蒸发仪(上海亚荣生化仪器厂); FA1004N万分之一电子分析天平(常州幸运电子有限公司); SCIEX 5500+高效液相三重四极杆串联质谱仪(美国SCIEX公司); Zorbax Eclipse Plus C18色谱柱(100 mm×3 mm, 1.8 µm, 美国Agilent科技公司); NDJ-79A旋转粘度计(上海昌吉地质仪器有限公司)。
1.2 实验方法
1.2.1 标准溶液的配制
准确称取1.0 mg CML、CEL标准品, 分别置于10 mL棕色容量瓶中, 加入纯水定容, 配制成100 µg/mL的标准储备液, 于-19 ℃下保存备用。检测时用纯水稀释标准溶液, 配制成不同浓度的CML、CEL标准工作液。准确称取10.0 mg 5-HMF标准品, 置于10 mL棕色容量瓶中, 加入纯水定容, 配制成1.0 mg/mL的标准储备液, 于-20 ℃下保存备用。检测时取出在4 ℃缓慢解冻, 用纯水稀释标准溶液, 配制成不同浓度的5-HMF标准工作液(保持4 ℃)。
1.2.2 检测方法
(1) HPLC-MS/MS检测
色谱条件: 色谱柱为Zorbax Eclipse Plus C18色谱柱(100 mm×3 mm, 1.8 µm); 柱温25 ℃; 进样量设置为1~3 μL; 流动相为0.1%甲酸水(A)和甲醇(B); 流速设置为0.15~0.40 mL/min。梯度洗脱程序为: 0~1.0 min, 95% A; 1.0~4.0 min, 95%~10% A; 4.0~6.0 min, 10% A; 6.0~6.1 min, 10%~95% A; 6.1~8.0 min, 95% A。质谱条件: 离子源模式: 电喷雾离子源正离子(electro spray ionization, ESI+); 扫描方式为多反应监测(multiple reaction monitoring, MRM)模式; 干燥气温度350 ℃; 干燥气流速10 L/min; 喷雾器压力25 psi; 鞘气温度300 ℃; 鞘气流速9 L/min; 毛细管电压3500 V; 喷嘴电压400 V; CML、CEL的碰撞能量分别为25 V和32 V; CML、CEL的定量离子分别是m/z 205.1→84.1和m/z 219.2→84。
(2) HPLC检测
色谱柱: Sun Fire C18色谱柱(250 mm×4.6 mm, 5 µm); 检测器: 二极管阵列检测器(photo-diode array detector, PAD); 检测波长285 nm; 流动相: 甲醇:水=10:90 (V:V); 流速为0.5~1.5 mL/min; 柱温30 ℃; 进样量为5~20 μL。
1.2.3 样品制备
参照严燕[22]、李红梅等[23]的方法制备果膏(图1)。挑选无机械损伤、无病虫害的枇杷鲜果, 清洗干净并沥干水分, 去除果核和果柄, 以榨汁机榨汁。用0.2%复合酶(纤维素酶:果胶酶=1:3, m:m)在40 ℃下水浴处理果浆60 min。酶解后用100目滤布过滤2~3遍, 以无肉眼可见果渣为标准。过滤后的枇杷果汁转入不锈钢锅中, 电磁炉加热至沸腾后换小火慢熬, 当果汁体积浓缩至原体积的2/3时加入10%白砂糖(以过滤后果汁质量计)继续熬制。熬制过程中需缓慢连续搅拌, 以防糊锅。浓度每升高5°Brix, 采用旋转粘度计在室温下测定经浓缩后得到的枇杷果膏所对应的黏度, 观察浓缩过程中枇杷果膏的黏度随糖度值变化的趋势, 找出枇杷果膏黏度突变点。此时枇杷果膏达到浓缩终点, 用玻璃瓶(使用前沸水浴15 min, 烘干备用)灌装。灌装后在沸水浴中保持3 min以灭菌, 放入4 ℃冰箱备用。制备3个平行样品。
1.2.4 枇杷果膏样品前处理
(1) CML、CEL SPE方法优化
精确称取1 g枇杷果膏样品于10 mL离心管中, 加入8 mL纯水进行浸提, 使用旋涡仪振荡30 s充分混匀后静置10 min, 超声(200 W)处理10 min。提取液于7000 r/min、4 ℃下离心10 min。取上清液上样过柱[选用60 mg、3 mL的MCX SPE小柱, 依次用3 mL甲醇和3 mL纯水活化平衡], 弃去流出液, 用9 mL纯水分3次过柱淋洗, 弃去淋洗液。分别用9 mL含有0%、5%、10%、15%、20%氨水的氨水-甲醇溶液分3次洗脱, 用15 mL离心管收集洗脱液, 氮吹至干, 用2 mL纯水复溶, 涡旋30 s混匀, 过0.22 μm水系微孔滤膜, 进行HPLC-MS/MS检测。
(2) 5-HMF液液萃取方法优化
对MACDONALD等[24]的方法进行优化, 并按照优化后的方法对枇杷果膏进行前处理。精确称取1 g枇杷果膏样品于15 mL离心管中, 加入10 mL纯水进行浸提, 使用旋涡仪振荡30 s充分混匀后静置10 min。转移至60 mL分液漏斗中, 分别以液液比=1:1.0、1:1.5、1:2.0、1:2.5、1:3.0的比例加入乙酸乙酯进行萃取。萃取过程重复3次, 弃去水相, 收集全部有机相, 转移至100 mL圆底烧瓶, 使用旋转蒸发仪于50 ℃下旋蒸至干, 加入10 mL 10%甲醇水复溶。收集至15 mL离心管, 涡旋30 s混匀, 使用HLB SPE柱(60 mg、3 mL)纯化富集: 首先分别使用3 mL甲醇和3 mL纯水活化平衡HLB柱; 再将复溶后溶液过柱, 弃去流出液; 然后用9 mL纯水分3次淋洗, 弃去淋洗液; 最后用10 mL 10%甲醇水溶液洗脱, 收集洗脱液。洗脱液过0.22 μm水系微孔滤膜, 进行HPLC检测。
1.2.5 方法学验证
(1)线性关系
稀释标准储备液, 配制质量浓度在5、10、25、50、100、250、500、1000、1500、2000、2500 ng/mL的CML和CEL混合标准溶液以及0.25、0.50、0.75、1.00、1.25、1.50、2.00、2.50、5.00 µg/mL的5-HMF标准溶液。过0.22 µm水系滤膜后按照1.2.2所述方法上样测定。实验重复3次。分别计算标准品响应强度下的积分面积。以标准品的质量浓度为横坐标, 峰面积为纵坐标, 绘制标准曲线, 进行线性回归分析, 从而可计算样液中目标物质的含量。
(2)检出限和定量限
将标准品溶液逐级降低浓度后进样, 根据信噪比S/N=3:1确定检出限(limit of detection, LOD), 10倍信噪比(S/N=10)所对应的标准品浓度作为定量限(limit of quantification, LOQ), AGEs和5-HMF的单位分别为ng/mL和µg/mL。
(3)精密度和稳定性
为考察方法的准确度和重现性, 需对其精密度进行测定。取标准溶液在同一天内连续进样6次, 记录其数据, 用所得相对标准偏差(relative standard deviation, RSD)表示其日内精密度; 对同一标准溶液连续5 d测定其峰面积, 所得RSD即为其日间精密度。取同一供试标准溶液分别于放置0、2、4、6、8、10、12、14、16 h后测定, 记录数据, 根据该组数据的RSD值来判断该方法在样品处理后的待测时间范围内的稳定程度。
(4)加标回收率
准确称取0.5 g枇杷果膏样品9份, 分别加入低、中、高3个不同浓度水平的标准溶液, 按照1.2.4的方法对样品进行前处理, 并按1.2.2的方法测定目标物质的含量。以不加标的样品为对照, 加标样品测定值减去对照组测定值, 再除以加标量, 乘100即为该方法的加标回收率。
以上所有实验均进行3次平行操作。
1.3 数据处理
使用Microsoft Office Excel 2016处理实验数据, IBM SPSS Statistics 26进行单因素方差分析(analysis of variance, ANOVA)分析, 事后多重比较采用Duncan法, P<0.05定义为显著水平, 用Origin 2021(美国OriginLab公司)作图。
2 结果与分析
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2.1 检测方法优化
2.1.1 进样量的选择
对于CML、CEL, 在进样量分别为1、2、3 µL的条件下, 观察两峰的保留时间、分离情况以及信号响应值高低。结果发现, 随着进样量的增加, 色谱峰响应值也升高。当进样量为1 µL时, 色谱峰存在拖尾现象, 而进样量为3 µL时, 两色谱峰存在部分重叠, 分离效果较差。进样量为2 µL时, 两峰面积与进样量为3 µL时接近, 且峰形对称, 故选择CML、CEL进样量为2 µL。
对于5-HMF, 在进样量为5、10、20 µL的条件下, 色谱峰响应值也随着进样量增加而增加。当进样量为10 µL时, 色谱峰峰形尖锐易于积分, 响应值适中, 而进样量5 µL时, 难以区分目标峰和杂质峰; 进样量20 µL时, 峰形反而不如进样量为10 µL时的好且浪费标准品。综合考虑, 选择5-HMF的进样量为10 µL。
2.1.2 流动相流速的选择
在流速分别为0.15、0.25、0.40 mL/min条件下, 考察CML、CEL物质峰的分离程度和响应情况。结果发现当流速为0.15 mL/min时, 保留时间长, 两峰分离效果较差, 且响应值较流速为0.25和0.40 mL/min时的低; 当流速为0.25 mL/min时, 两峰存在一定的分离度, 但考虑到食品基质的复杂性, 在实际检测过程中会存在一定的基质干扰, 故在二者峰面积相近的情况下, 选择分离度更高的流速(0.40 mL/min)。
在流速分别为0.50、1.00、1.50 mL/min条件下, 考察5-HMF目标峰的峰形和响应情况。结果发现, 当流速为0.50 mL/min时, 未检测到明显的色谱峰; 随着流速的增大, 目标峰的保留时间会缩短, 但同时也会使色谱柱压力增大, 进而降低色谱柱的使用寿命。当流速为1.00 mL/min时, 峰形对称, 尖锐狭窄, 便于对峰面积进行积分。LEE等[25]采用高效液相色谱法测定市售果汁中5-HMF含量, 选择流速为0.80 mL/min时的LOD和LOQ分别为0.46 µg/mL和1.40 µg/mL, 均高于本研究中5-HMF测定方法的LOD和LOQ (0.01 µg/mL和0.04 µg/mL)。综合考虑, 选择流速为1.00 mL/min。
优化后AGEs的HPLC-MS/MS色谱图和5-HMF的HPLC色谱图分别见图2和图3。
2.2 前处理条件优化
食品样品基质复杂多样, 在样品的前处理过程中, 应尽量消除其复杂成分带来的基体效应, 降低检测过程中的基质干扰以及富集组分带来的离子抑制作用, 以提高检测的准确性和可信度。因此, 本研究对枇杷果膏样品进行前处理优化, 以提高痕量危害物的检测准确性。
2.2.1 SPE条件优化
AGEs是羰基化合物和氨基化合物发生羰氨反应的产物。果品中游离氨基酸和蛋白质含量较肉品、烘焙食品少, AGEs含量低, 仅以ng/mL计, 且果膏样品基质复杂, 杂质干扰大。SPE的原理是使样液流经吸附剂时, 被测物质被保留在吸附剂中, 用溶液淋洗可除去吸附剂中的杂质, 而被测组分被富集, 再以另一溶液将其洗脱下来, 即可有效降低复杂基质带来的基体效应, 减少基质噪声对检测结果的不良影响。CML和CEL是强极性的两性离子化合物。MCX SPE小柱填料是在高度交联的聚苯乙烯-二乙烯基苯共聚物表面键合磺酸基团的混合型强阳离子吸附剂, 能同时截留干扰物和选择性离子交换截留AGEs, 最后通过离子交换置换出吸附剂中的AGEs[26-27]。研究表明, 它比表面积大, 离子交换容量大, 吸附效率强, 具有反向和阳离子交换两种性能, 对样品中AGEs具有较高的回收率[28]。本研究对MCX SPE小柱洗脱液比例进行优化, 并对样品中AGEs含量进行测定。
如图4所示, 随着洗脱液中氨水浓度增加, 目标物响应值均呈现先升高后下降的趋势。这表明氨水-甲醇的组合使用可以破坏目标物与吸附剂之间的库仑力和非极性相互作用, 但过高浓度的氨水会改变吸附体系的酸碱性, 从而对洗脱效果产生影响, 导致洗脱不彻底[29]。其中CML(图4A)的检测值在氨水洗脱液浓度为5%时达到峰值, 而CEL(图4B)的检测值在氨水浓度为10%时达到顶峰。值得注意的是, 当氨水浓度分别为5%和10%时, CML含量相差不大。综合考虑, 最终选用10%氨水-甲醇洗脱液。在该条件下, 枇杷果膏中的CML和CEL含量分别测得为3.87 μg/kg和31.09 μg/kg。
2.2.2 液液萃取条件优化
HLB SPE小柱采用的吸附剂是一种具有强吸附能力和高回收率的大孔共聚物, 可分为亲水性的N-乙烯基吡咯烷酮和疏水性的二乙烯基苯, 前者可保留极性化合物, 而后者保留非极性化合物, pH适用范围广。本研究采用乙酸乙酯液液萃取串联HLB SPE的方法对样品进行前处理, 富集净化5-HMF组分, 以便测定其含量。
如图5所示, 随着萃取溶剂比例的升高, 5-HMF萃取效率均不断升高, 且5-HMF含量在样液:萃取液=1:2.5 (V:V)时达到峰值。这表明乙酸乙酯的大量存在会增加5-HMF向其相扩散的动力[30]。考虑到避免试剂浪费、降低实验成本的原则, 选择1:2.0 (V:V)的液液萃取比例。在该条件下, 枇杷果膏中的5-HMF含量测得为6.13 mg/kg。
2.3 方法学验证
2.3.1 线性关系
以3种危害物标准品的质量浓度为横坐标, 峰面积为纵坐标, 分别绘制标准曲线并进行线性回归分析。结果如表1所示, 相关系数(r2)均大于0.999, 这表明所有目标物在浓度范围内均线性关系良好。
2.3.2 LOD和LOQ
根据信噪比S/N=3:1和S/N=10:1确定了所有目标物质的LOD和LOQ。其中CML、CEL、5-HMF的LOD分别为0.159 ng/mL、0.113 ng/mL和0.010 µg/mL; LOQ分别为0.531 ng/mL、0.378 ng/mL和0.040 µg/mL(表2)。所有目标物质的LOD和LOQ值均小于1 [AGEs/(ng/mL); 5-HMF/(µg/mL)], 这反映该检测方法具有较灵敏的痕量物质定量检测能力。
2.3.3 精密度和稳定性
CML的稳定性为0.58%, 日内精密度为8.72%, 日间精密度为8.91%; CEL稳定性为0.33%, 日内精密度为5.62%, 日间精密度为6.79%; 5-HMF稳定性为0.45%, 日内精密度2.94%, 日间精密度8.79%。所有物质的RSDs均小于10%, 且在16 h样品待测时间范围内低于0.6%, 说明该方法具有良好的准确性和稳定性。
2.3.4 加标回收率
所有物质的加标回收率均大于85%, 说明该方法可满足定量分析的基本要求。
3 结论
收起
本研究建立了枇杷果膏中AGEs和5-HMF的提取、分离纯化与检测分析方法, 分别采用HPLC-MS/MS和HPLC分析, 研究了不同检测参数及前处理方法对AGEs和5-HMF检测效果的影响。方法学验证表明, 3种目标物在浓度范围内均线性关系良好。CML、CEL、5-HMF的LOQ分别为0.531 ng/mL、0.378 ng/mL和0.040 µg/mL, 可满足检测痕量物质的检测要求, 且具有良好的准确性和稳定性, 能满足定量分析的基本要求。下一步将本方法应用于更多果蔬制品中AGEs和5-HMF含量的检测, 扩大其样本容量, 验证该方法的广泛适应性, 为后续果蔬制品中AGEs和5-HMF形成影响因素及其控制研究奠定基础, 以保障公众对果蔬浓缩制品和干制品质量与安全状况的知情权和对营养健康食品的需求。
基金
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  • 省部共建农产品质量危害因子与风险防控国家重点实验室资助项目(2021DG700024-ZZ202210)
  • 浙江省“三农六方”科技协作计划项目(2021SNLF013)
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doi: 10.19812/j.cnki.jfsq11-5956/ts.20240902001
  • 接收时间：2024-09-02
  • 首发时间：2025-07-21
  • 出版时间：2025-02-15
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  • 收稿日期：2024-09-02
基金
省部共建农产品质量危害因子与风险防控国家重点实验室资助项目(2021DG700024-ZZ202210)
浙江省“三农六方”科技协作计划项目(2021SNLF013)
作者信息
    1.南京农业大学食品科技学院, 南京 210095
    2.浙江省农业科学院食品科学研究所, 农产品质量安全危害因子与风险防控国家重点实验室, 杭州 310021

通讯作者:

* 陆胜民(1969—), 男, 博士, 研究员, 主要研究方向为果品加工质量与安全控制。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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