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Article(id=1153429502572093986, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153429493357203682, articleNumber=null, orderNo=null, doi=10.19812/j.cnki.jfsq11-5956/ts.20241111002, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1731254400000, receivedDateStr=2024-11-11, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1752928623097, onlineDateStr=2025-07-19, pubDate=1741968000000, pubDateStr=2025-03-15, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1752928623097, onlineIssueDateStr=2025-07-19, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1752928623097, creator=13701087609, updateTime=1752928623097, updator=13701087609, issue=Issue{id=1153429493357203682, tenantId=1146029695717560320, journalId=1149652044408987649, year='2025', volume='16', issue='5', pageStart='1', pageEnd='326', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=0, createTime=1752928620900, creator=13701087609, updateTime=1758690311058, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1177595773500932351, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153429493357203682, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1177595773500932352, tenantId=1146029695717560320, journalId=1149652044408987649, issueId=1153429493357203682, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=46, endPage=51, ext={EN=ArticleExt(id=1153429503352234534, articleId=1153429502572093986, tenantId=1146029695717560320, journalId=1149652044408987649, language=EN, title=Determination of 5 kinds of lactose derivatives in milk and dairy products by pre-column derivatization-high performance liquid chromatography, columnId=1153429494888129034, journalTitle=Journal of Food Safety & Quality, columnName=Highlight: Guangzhou Inspection Testing and Certification Group Co., Ltd., runingTitle=null, highlight=null, articleAbstract=

Objective To establish a quantitative analysis method for determining the content of 5 kinds of lactose derivatives (3'-galactosyllactose, 4'-galactosyllactose, 6'-galactosyllactose, 3'-sialyllactose, 6'-sialyllactose) in milk and dairy products by pre-column derivatization-high performance liquid chromatography. Methods The proteins in milk and dairy products were precipitated. The 5 kinds of lactose derivatives were reacted with 2-aminobenzamide at 55 ℃ for 120 min to label the fluorescent groups. The 5 kinds of lactose derivatives were separated by high performance liquid chromatography with an amide column and quantified by external standard method. Results The 5 kinds of lactose derivatives exhibited good linear relationships within the concentration range of 0.025-5.000 mg/L, with correlation coefficients (r) all exceeding 0.999. The limits of detection and quantification for the 5 kinds of lactose derivatives ranged from 3.5 to 7.5 mg/kg and 12.0 to 25.0 mg/kg, respectively. The recovery rates for the 5 kinds of lactose derivatives were between 90.8% and 103.3%, with relative deviations in detection results ranging from 2.8% to 5.3% (n=3). Conclusion This method demonstrates good precision, recovery rate, and sensitivity, making it suitable for determining the content of 5 kinds of lactose derivatives in milk and dairy products.

, correspAuthors=Wei-Qian HUANG, 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=Wei-Qian HUANG, Jun-Fa WU, Tian-Fu QIN, Si-Yi DENG, Zhi-Sen LIANG, Min-Lian WU), CN=ArticleExt(id=1153429531345019286, articleId=1153429502572093986, tenantId=1146029695717560320, journalId=1149652044408987649, language=CN, title=柱前衍生-高效液相色谱法测定乳及乳制品中5种乳糖衍生物, columnId=1153429495039123980, journalTitle=食品安全质量检测学报, columnName=本期重点：广州检验检测认证集团有限公司, runingTitle=null, highlight=null, articleAbstract=

目的 建立柱前衍生-高效液相色谱法测定乳及乳制品中5种乳糖衍生物(3'-半乳糖基乳糖、4'-半乳糖基乳糖、6'-半乳糖基乳糖、3'-唾液酸乳糖、6'-唾液酸乳糖)含量的定量分析方法。方法 乳及乳制品经沉淀蛋白, 于55 ℃下5种乳糖衍生物与2-氨基苯甲酰胺反应120 min, 标记上荧光基团, 经高效液相色谱酰胺柱分离, 外标法定量5种乳糖衍生物的含量。结果 5种乳糖衍生物在0.025~5.000 mg/L质量浓度范围内线性关系良好, 相关系数(r)均大于0.999; 5种乳糖衍生物的检出限和定量限在3.5~7.5 mg/kg和12.0~25.0 mg/kg之间; 5种乳糖衍生物的的回收率在90.8%~103.3%, 检测结果的相对偏差在2.8%~5.3% (n=3)。结论 本方法的精密度和回收率良好, 灵敏度较好, 可用于乳与乳制品中5种乳糖衍生物含量的测定。

, correspAuthors=黄伟乾, authorNote=null, correspAuthorsNote=
* 黄伟乾(1986—), 男, 工程师, 主要研究方向为食品安全质量检验检测。E-mail:
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Grain, Oil and Feed Technology, 2024(3): 231-233., articleTitle=Application of high performance liquid chromatography technology in food detection, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1177619611622195669, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, xref=null, ext=[AuthorCompanyExt(id=1177619611630584278, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, companyId=1177619611622195669, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=Guangzhou Inspection Testing and Certification Group Co., Ltd., Guangzhou 511447, China), AuthorCompanyExt(id=1177619611638972887, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, companyId=1177619611622195669, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=广州检验检测认证集团有限公司, 广州 511447)])], figs=[ArticleFig(id=1177619614239441467, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Fig.1, caption=Effects of temperature on the response value, figureFileSmall=P0hdG2STy62BorTCkox+NA==, figureFileBig=0ZPNnlEr5SETcqro5Jw+Bw==, tableContent=null), ArticleFig(id=1177619614331716160, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=图1, caption=温度对响应值的影响, figureFileSmall=P0hdG2STy62BorTCkox+NA==, figureFileBig=0ZPNnlEr5SETcqro5Jw+Bw==, tableContent=null), ArticleFig(id=1177619614537237060, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Fig.2, caption=Effects of derivative time on the response value, figureFileSmall=jrasoyrnGUXv5OTeahBvJw==, figureFileBig=GdouL/lJJass1JqCi07/nw==, tableContent=null), ArticleFig(id=1177619614646288968, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=图2, caption=衍生时间对响应值的影响, figureFileSmall=jrasoyrnGUXv5OTeahBvJw==, figureFileBig=GdouL/lJJass1JqCi07/nw==, tableContent=null), ArticleFig(id=1177619614717592138, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Fig.3, caption=Effects of derivatization agent concentration on the response value, figureFileSmall=oy+U6ZTpSAKMSLWZ0DqObA==, figureFileBig=b3bnBUDY2sIUCva4Y1XuvQ==, tableContent=null), ArticleFig(id=1177619614814061137, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=图3, caption=衍生剂浓度对响应值的影响, figureFileSmall=oy+U6ZTpSAKMSLWZ0DqObA==, figureFileBig=b3bnBUDY2sIUCva4Y1XuvQ==, tableContent=null), ArticleFig(id=1177619614889558611, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Fig.4, caption=Standard chromatogram of 5 lactose derivatives, figureFileSmall=xhL3NwM2HeLdLUm9CV4lpQ==, figureFileBig=tnS6AjSw7FVE31+GdfsdiA==, tableContent=null), ArticleFig(id=1177619614969250390, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=图4, caption=5种乳糖衍生物的标准色谱图, figureFileSmall=xhL3NwM2HeLdLUm9CV4lpQ==, figureFileBig=tnS6AjSw7FVE31+GdfsdiA==, tableContent=null), ArticleFig(id=1177619615086690905, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Fig.5, caption=Chromatogram of infant formula powder, figureFileSmall=r3P3v5t2ys8G1cJDa/E15g==, figureFileBig=kGB553a2qPu33ESlcTCXxw==, tableContent=null), ArticleFig(id=1177619615174771291, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=图5, caption=婴幼儿配方乳粉的色图谱, figureFileSmall=r3P3v5t2ys8G1cJDa/E15g==, figureFileBig=kGB553a2qPu33ESlcTCXxw==, tableContent=null), ArticleFig(id=1177619615292211807, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Fig.6, caption=Chromatogram of pure milk added sample, figureFileSmall=qDFmVxb8fapiSoUTGqFScA==, figureFileBig=4NnesDKyyWbWBIRq5zNpIw==, tableContent=null), ArticleFig(id=1177619615405458017, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=图6, caption=纯牛奶加标样品的色谱图, figureFileSmall=qDFmVxb8fapiSoUTGqFScA==, figureFileBig=4NnesDKyyWbWBIRq5zNpIw==, tableContent=null), ArticleFig(id=1177619615476761186, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Table 1, caption=

Gradient program of mobile phase elution

, figureFileSmall=null, figureFileBig=null, tableContent=
时间/min 流动相A/% 流动相B/%
0.0 95 5
15.0 95 5
37.0 75 25
42.0 75 25
42.1 40 60
48.0 40 60
48.1 95 5
60.0 95 5
), ArticleFig(id=1177619615552258658, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=表1, caption=

流动相洗脱梯度程序

, figureFileSmall=null, figureFileBig=null, tableContent=
时间/min 流动相A/% 流动相B/%
0.0 95 5
15.0 95 5
37.0 75 25
42.0 75 25
42.1 40 60
48.0 40 60
48.1 95 5
60.0 95 5
), ArticleFig(id=1177619615636144740, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Table 2, caption=

Linear ranges, linear equations, correlation coefficients, MLODs and MLOQs of 5 kinds of lactose derivatives

, figureFileSmall=null, figureFileBig=null, tableContent=
名称 线性范围/(mg/L) 线性方程 r MLODs/(mg/kg) MLOQs/(mg/kg)
4'-GL 0.025~5.000 Y=82586.1X+1826.7 0.9998 4.0 13.0
3'-GL 0.025~5.000 Y=77526.4X+1842.5 0.9999 4.2 14.0
3'-SL 0.025~5.000 Y=64207.8X+1561.7 0.9999 5.4 18.0
6'-GL 0.025~5.000 Y=105996.8X+3493.3 0.9998 3.5 12.0
6'-SL 0.025~5.000 Y=52943.4X+1382.9 0.9998 7.5 25.0
), ArticleFig(id=1177619615703253607, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=表2, caption=

5种乳糖衍生物的线性范围、线性方程、相关系数、MLODs与MLOQs

, figureFileSmall=null, figureFileBig=null, tableContent=
名称 线性范围/(mg/L) 线性方程 r MLODs/(mg/kg) MLOQs/(mg/kg)
4'-GL 0.025~5.000 Y=82586.1X+1826.7 0.9998 4.0 13.0
3'-GL 0.025~5.000 Y=77526.4X+1842.5 0.9999 4.2 14.0
3'-SL 0.025~5.000 Y=64207.8X+1561.7 0.9999 5.4 18.0
6'-GL 0.025~5.000 Y=105996.8X+3493.3 0.9998 3.5 12.0
6'-SL 0.025~5.000 Y=52943.4X+1382.9 0.9998 7.5 25.0
), ArticleFig(id=1177619615799722601, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Table 3, caption=

Recovery and precision determination results of 5 kinds of lactose derivatives (n=3)

, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 添加水平/ (mg/kg) 回收率/% 相对标准偏差/%
4'-GL 25; 100; 600 91.1; 98.3; 101.9 3.9; 3.8; 4.4
3'-GL 25; 100; 600 90.8; 100.8; 102.3 3.6; 3.9; 3.6
3'-SL 25; 100; 600 93.0; 98.7; 103.3 3.9; 3.8; 4.9
6'-GL 25; 100; 600 91.9; 96.1; 100.4 2.8; 2.9; 3.5
6'-SL 25; 100; 600 93.2; 97.5; 99.4 3.9; 4.2; 5.3
), ArticleFig(id=1177619615938134637, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=表3, caption=

5种乳糖衍生物的回收率和精密度测定结果(n=3)

, figureFileSmall=null, figureFileBig=null, tableContent=
化合物 添加水平/ (mg/kg) 回收率/% 相对标准偏差/%
4'-GL 25; 100; 600 91.1; 98.3; 101.9 3.9; 3.8; 4.4
3'-GL 25; 100; 600 90.8; 100.8; 102.3 3.6; 3.9; 3.6
3'-SL 25; 100; 600 93.0; 98.7; 103.3 3.9; 3.8; 4.9
6'-GL 25; 100; 600 91.9; 96.1; 100.4 2.8; 2.9; 3.5
6'-SL 25; 100; 600 93.2; 97.5; 99.4 3.9; 4.2; 5.3
), ArticleFig(id=1177619616013632110, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Table 4, caption=

Test results of 7 samples (mg/kg)

, figureFileSmall=null, figureFileBig=null, tableContent=
样品 4'-GL 3'-GL 3'-SL 6'-GL 6'-SL
婴幼儿配方乳粉1 6.37×103 1.99×103 271 92 2.15×103
婴幼儿配方乳粉2 3.61×103 905 251 <12 1.34×103
婴幼儿配方乳粉3 2.45×103 556 115 48 665
有机纯牛奶4 108 132 273 23 48
脱脂奶粉5 未检出 236 595 未检出 33
巴氏灭菌牛奶6 未检出 未检出 92 未检出 未检出
纯牛奶7 未检出 未检出 67 未检出 未检出
), ArticleFig(id=1177619616118489712, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=表4, caption=

7个乳制品样品的检测结果(mg/kg)

, figureFileSmall=null, figureFileBig=null, tableContent=
样品 4'-GL 3'-GL 3'-SL 6'-GL 6'-SL
婴幼儿配方乳粉1 6.37×103 1.99×103 271 92 2.15×103
婴幼儿配方乳粉2 3.61×103 905 251 <12 1.34×103
婴幼儿配方乳粉3 2.45×103 556 115 48 665
有机纯牛奶4 108 132 273 23 48
脱脂奶粉5 未检出 236 595 未检出 33
巴氏灭菌牛奶6 未检出 未检出 92 未检出 未检出
纯牛奶7 未检出 未检出 67 未检出 未检出
), ArticleFig(id=1177619616223347314, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=EN, label=Table 5, caption=

Test results analysis of 2 methods (mg/kg)

, figureFileSmall=null, figureFileBig=null, tableContent=
样品 方法 4'-GL 3'-GL 3'-SL 6'-GL 6'-SL
婴幼儿配方奶粉8 本方法 35 42 825 20 350
其他方法 / / 790 / 335
/ 无标示值 无标示值 标示值: 770 无标示值 明示值: 280
婴幼儿配方奶粉9 本方法 55 75 785 28 400
其他方法 / / 765 / 408
/ 无标示值 无标示值 标示值: 730 无标示值 明示值: 360
), ArticleFig(id=1177619616307233396, tenantId=1146029695717560320, journalId=1149652044408987649, articleId=1153429502572093986, language=CN, label=表5, caption=

2个方法的测试结果分析(mg/kg)

, figureFileSmall=null, figureFileBig=null, tableContent=
样品 方法 4'-GL 3'-GL 3'-SL 6'-GL 6'-SL
婴幼儿配方奶粉8 本方法 35 42 825 20 350
其他方法 / / 790 / 335
/ 无标示值 无标示值 标示值: 770 无标示值 明示值: 280
婴幼儿配方奶粉9 本方法 55 75 785 28 400
其他方法 / / 765 / 408
/ 无标示值 无标示值 标示值: 730 无标示值 明示值: 360
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柱前衍生-高效液相色谱法测定乳及乳制品中5种乳糖衍生物
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黄伟乾 * , 吴俊发 , 覃天福 , 邓思怡 , 梁志森 , 吴敏莲
食品安全质量检测学报 | 本期重点：广州检验检测认证集团有限公司 2025,16(5): 46-51
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食品安全质量检测学报 | 本期重点：广州检验检测认证集团有限公司 2025, 16(5): 46-51
柱前衍生-高效液相色谱法测定乳及乳制品中5种乳糖衍生物
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黄伟乾* , 吴俊发, 覃天福, 邓思怡, 梁志森, 吴敏莲
作者信息
  • 广州检验检测认证集团有限公司, 广州 511447

通讯作者:

* 黄伟乾(1986—), 男, 工程师, 主要研究方向为食品安全质量检验检测。E-mail:
Determination of 5 kinds of lactose derivatives in milk and dairy products by pre-column derivatization-high performance liquid chromatography
Wei-Qian HUANG* , Jun-Fa WU, Tian-Fu QIN, Si-Yi DENG, Zhi-Sen LIANG, Min-Lian WU
Affiliations
  • Guangzhou Inspection Testing and Certification Group Co., Ltd., Guangzhou 511447, China
出版时间: 2025-03-15 doi: 10.19812/j.cnki.jfsq11-5956/ts.20241111002
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摘要
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目的 建立柱前衍生-高效液相色谱法测定乳及乳制品中5种乳糖衍生物(3'-半乳糖基乳糖、4'-半乳糖基乳糖、6'-半乳糖基乳糖、3'-唾液酸乳糖、6'-唾液酸乳糖)含量的定量分析方法。方法 乳及乳制品经沉淀蛋白, 于55 ℃下5种乳糖衍生物与2-氨基苯甲酰胺反应120 min, 标记上荧光基团, 经高效液相色谱酰胺柱分离, 外标法定量5种乳糖衍生物的含量。结果 5种乳糖衍生物在0.025~5.000 mg/L质量浓度范围内线性关系良好, 相关系数(r)均大于0.999; 5种乳糖衍生物的检出限和定量限在3.5~7.5 mg/kg和12.0~25.0 mg/kg之间; 5种乳糖衍生物的的回收率在90.8%~103.3%, 检测结果的相对偏差在2.8%~5.3% (n=3)。结论 本方法的精密度和回收率良好, 灵敏度较好, 可用于乳与乳制品中5种乳糖衍生物含量的测定。

乳及乳制品  /  高效液相色谱法  /  乳糖衍生物

Objective To establish a quantitative analysis method for determining the content of 5 kinds of lactose derivatives (3'-galactosyllactose, 4'-galactosyllactose, 6'-galactosyllactose, 3'-sialyllactose, 6'-sialyllactose) in milk and dairy products by pre-column derivatization-high performance liquid chromatography. Methods The proteins in milk and dairy products were precipitated. The 5 kinds of lactose derivatives were reacted with 2-aminobenzamide at 55 ℃ for 120 min to label the fluorescent groups. The 5 kinds of lactose derivatives were separated by high performance liquid chromatography with an amide column and quantified by external standard method. Results The 5 kinds of lactose derivatives exhibited good linear relationships within the concentration range of 0.025-5.000 mg/L, with correlation coefficients (r) all exceeding 0.999. The limits of detection and quantification for the 5 kinds of lactose derivatives ranged from 3.5 to 7.5 mg/kg and 12.0 to 25.0 mg/kg, respectively. The recovery rates for the 5 kinds of lactose derivatives were between 90.8% and 103.3%, with relative deviations in detection results ranging from 2.8% to 5.3% (n=3). Conclusion This method demonstrates good precision, recovery rate, and sensitivity, making it suitable for determining the content of 5 kinds of lactose derivatives in milk and dairy products.

milk and dairy products  /  high performance liquid chromatography  /  lactose derivatives
黄伟乾, 吴俊发, 覃天福, 邓思怡, 梁志森, 吴敏莲. 柱前衍生-高效液相色谱法测定乳及乳制品中5种乳糖衍生物. 食品安全质量检测学报, 2025 , 16 (5) : 46 -51 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20241111002
Wei-Qian HUANG, Jun-Fa WU, Tian-Fu QIN, Si-Yi DENG, Zhi-Sen LIANG, Min-Lian WU. Determination of 5 kinds of lactose derivatives in milk and dairy products by pre-column derivatization-high performance liquid chromatography[J]. Journal of Food Safety & Quality, 2025 , 16 (5) : 46 -51 . DOI: 10.19812/j.cnki.jfsq11-5956/ts.20241111002
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0 引言
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母乳[1-2]是婴幼儿最优质的食物, 含有重要的混合低聚糖(如: 母乳寡聚糖), 可促进婴幼儿肠道免疫系统的发育。研究表明低聚半乳糖[3-6]也具有调节免疫系统的功能。且随着对天然的碳水化合物的研究, 特别是乳糖[7]形成的多种聚合物, 发现其对婴幼儿生长发育具有显著作用, 因此添加此类功能性碳水合物的产品也是生产企业宣传的亮点。但目前此类天然功能性乳糖衍生物(如: 3'-半乳糖基乳糖)因缺少相应的标准检测方法, 故无法确定其含量。
3'-半乳糖基乳糖(3'-galactosyllactose, 3'-GL)、4'-半乳糖基乳糖(4'-galactosyl lactose, 4'-GL)与6'-半乳糖基乳糖(6'-galactosyl lactose, 6'-GL)为同分异构体, 是一种重要的母乳寡聚糖(又称母乳低聚糖, human milkoligosaccharides, HMOs)。目前针对3'-GL的报道较多, 研究表明其具有多种生物活性, 包括免疫调节、抗炎症以及保护肠道屏障功能, 能够直接影响免疫细胞, 并有助于调节先天免疫反应, 是一种具有重要生物学意义的低聚糖[8], 对婴儿的健康和发育起着关键作用。4'-GL[9]与6'-GL结构非常类似, 也具有类似的改善肠道健康, 维持免疫平衡等作用。3'-唾液酸乳糖(3'-sialoglactose, 3'-SL)与6'-唾液酸乳糖(6'-sialoglactose, 6'-SL)为同分异构体, 具有调节免疫反应的能力, 因为唾液酸在细胞识别和免疫调节中起着重要作用, 阻止病原体如细菌和病毒黏附到宿主细胞上, 预防感染, 且参与细胞间的信号传递, 影响细胞的生长、分化和凋亡。因此3'-SL和6'-SL在食品工业中被用作添加剂以增强产品的营养价值或功能性[10-13]。
目前报道乳糖类衍生物的研究较少, 主要是母乳低聚糖[14-19]、2'-岩藻基乳糖[20]、低聚半乳糖[21-23]以及其在食品方面的应用。2'-岩藻基乳糖的检测已形成团体标准, 方法是使用β-半乳糖苷酶酶解去除乳糖类干扰物, 再通过离子色谱分离, 外标法定量; 低聚半乳糖、7种HMOs的研究是通过液相色谱-串联质谱法检测, 且已形成标准方法。但鲜少见乳与乳制品中3'-GL[24]、4'-GL、6'-GL等的检测报道, 虽单个的乳糖衍生物[25]含量较低(一般<1%), 但也是重要的营养组成和功能性碳水化合物之一, 是非常有价值的研究对象。
由于乳与乳制品中乳糖衍生物含量低且未见明显的吸光基团, 需通过衍生化方式标识吸光基团, 使用2-氨基苯甲酰胺(2-aminobenzamide, 2-AB)与乳糖衍生物[26]发生还原氨化反应[5]可以增强响应, 引入共轭双键的苯环基团, 同时选择荧光检测器检测, 大大提高了测定灵敏度, 但鲜少有研究应用此技术检测乳糖衍生物。因此, 本研究采用衍生[27-28]法与高效液相色谱分离技术[29-30]检测组合, 建立定量检测乳及乳制品中5种乳糖衍生物的分析方法, 为产品质量的监管提供技术支持。
1 材料与方法
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1.1 材料与试剂
乳制品样品(9批): 广州市售的产品。
标准品: 3'-SL(纯度>99%)、6'-SL(纯度>99%)、3'-GL(纯度>98%)、4'-GL(纯度>96%)、6'-GL(纯度>98%)(上海安谱贸易有限公司)。
乙腈、甲酸铵、甲酸、乙酸(色谱纯, 美国Fisher公司); 二甲基亚砜、2-AB、氰基硼氢化钠(分析纯, 上海安谱科技科技有限公司)。
1.2 仪器与设备
U3000高效液相色谱仪(美国赛默飞世尔科技有限公司); Aquaplore 2S纯水系统(重庆艾科浦颐洋企业发展有限公司); MS204T万分之一分析天平[梅特勒托利多测量设备(上海)有限公司]; HSW-26恒温水浴(上海一恒科学仪器有限公司); MS3涡旋振荡器[艾卡(广州)仪器设备有限公司]; XBridge Amide色谱柱(4.6 mm×150 mm, 3.5 μm, 美国Waters公司); KQ5200E超声波清洗机(昆山市超声仪器有限公司)。
1.3 标准溶液及试剂的配制
混合标准贮备溶液: 精密称量3'-GL、4'-GL、6'-GL、3'-SL、6'-SL标准品各10.0 mg, 加水溶解定容至10.0 mL, 配成质量浓度为1000 mg/L的标准溶液, 置于-18 ℃下保存。
混合标准工作溶液; 移取2.00 mL标准贮备液, 加水定容至10.00 mL, 配成质量浓度为200 mg/L的工作溶液。再分别移取0.025、0.100、0.500、1.000、2.500、5.000 mL再稀释至10.0 mL, 成0.50、2.00、10.00、20.00、50.00、100.00 mg/L系列标准工作溶液。
衍生溶液(0.45 mol/L 2-AB溶液): 分别称取612 mg 2-AB和630 mg氰基硼氢化钠于10 mL容量瓶中, 用二甲基亚砜-乙酸溶液(30:70, V:V)定容(现配现用)。
甲酸铵溶液(0.02 mol/L): 称取1.26 g甲酸铵, 加水溶解, 用甲酸调至pH 4.5±0.1, 加水稀释至1 L, 经0.45 μm滤膜过滤后备用。
1.4 实验方法
1.4.1 前处理步骤
称取样品约1.0~5.0 g(精确至1 mg), 加水约40 mL溶解, 用冰醋酸调节至pH 4.5±0.1沉淀蛋白, 再定容至100 mL, 超声提取5 min, 中速定性滤纸过滤, 移取滤液250 µL于10 mL的离心管中, 再加入250 µL的衍生试剂溶液, 于涡旋振荡器上混合均匀, 将离心管置于55 ℃的水浴中2 h。冷却后, 用甲酸铵溶液乙腈混合液(40:60, V:V)稀释至5.0 mL, 涡旋混匀1 min, 过尼龙0.45 μm滤膜后, 待高效液相色谱仪分析。
1.4.2 计算方法
乳糖衍生物(如: 3'-GL、4'-GL、6'-GL、3'-SL、6'-SL)含量的计算公式(1)如下:
$\text { 乳糖衍生物/(mg/100 g) }=\frac{c \times V \times f}{m} \times \frac{100}{1000}$
式中: c为待测液的质量浓度, mg/L; V为定容体积, mL; m为称样质量, g; f为衍生过程中产生的稀释倍数(20倍)。
1.4.3 色谱分析条件
色谱柱: XBridge Amide分析柱(150 mm×4.6 mm, 3.5 μm); 柱温: 25 ℃; 进样量: 5 µL; 流量: 1.0 mL/min; 激发波长: 350 nm, 发射波长: 430 nm; 流动相A(乙腈), 流动相B (0.02 mol/L甲酸铵溶液, pH 4.5±0.1), 梯度洗脱程序见表1。
1.5 数据处理
实验所得数据以及平行测试3次的相对标准偏差的计算均使用金山WPS 2019进行数据整理以及分析。其中5种乳糖衍生物的检测数据采用自带的仪器控制软件变色龙Chromeleon 7.3.1进行采集和处理, 以外标法计算结果。
2 结果与分析
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2.1 蛋白沉淀剂种类的的确定
蛋白沉淀剂种类的选择实验比较了乙酸锌亚铁氰化钾溶液、80%乙醇水溶液、冰醋酸溶液的沉淀效果。结果表明, 用冰醋酸溶液和乙酸锌亚铁氰化钾作为沉淀剂时, 使蛋白质的溶解性明显降低, 蛋白质凝聚并从溶液中析出, 但乙酸锌亚铁氰化钾带入盐类的较多, 对色谱柱的污染较大。因此, 确定冰醋酸溶液为乳制品样品的蛋白沉淀剂。
2.2 衍生反应关键因素的确定
为了确定适宜的衍生反应, 参考文献[3,12]的研究, 以探究对5种乳糖衍生物的衍化结果的影响, 实验使用纯牛奶样品, 添加水平为400 mg/100 g的混合标准溶液, 按实验方法(1.4)的步骤处理。实验比较了温度50、55、60、65℃, 衍生时间80、100、120、140 min; 衍生剂的浓度0.35、0.40、0.45、0.50 mol/L对衍生物的影响, 对应的响应值都呈现先上升后下降的趋势。由图1~3分析可知, 衍生剂浓度为0.45 mol/L, 衍生温度为55 ℃下, 衍生化时间为120 min的衍生物响应较高。
再以2-AB衍生剂浓度为0.45 mol/L, 衍生温度为55 ℃下, 衍生化时间为120 min, 回收率达到90%以上, 基本能满足方法验证的要求。故直接选用该衍生化条件。
2.3 色谱分离条件的优化
3'-GL、4'-GL、6'-GL为半乳糖基结合到乳糖的3、4、6位上, 互为同分异构体; 3'-SL、6'-SL为唾液酸基结合到乳糖的3、6位上, 也互为同分异构体。由于结构非常相似, 保留时间相近, 分离难度较大。
本研究以甲酸铵+乙腈作为流动相, 比较了多糖类分析柱(Waters XBridge酰胺分析柱、Agilent AdvanceBio Glycan糖谱分析柱、Welch hilic Amide分析柱), 优选后确定为XBridge酰胺分析柱, 经调整洗脱梯度和优化分离度, 得到5种乳糖衍生物的分离效果较佳(分离度R≥1.1)淋洗梯度见表1。5种乳糖衍生物的标准图谱见图4。由图4可知, 5种乳糖衍生物的分离满足要求, 可用于乳与乳制品的测试。
2.4 方法学验证
2.4.1 标准曲线和方法灵敏度
分别移取250 μL系列标准工作溶液进行衍生(衍生后最终质量浓度分别为0.025、0.100、0.500、1.000、2.500、5.000 mg/L), 过滤后供高效液相色谱仪分析, 以质量浓度为横坐标(X, mg/L), 峰面积为纵坐标(Y), 绘制线性方程。相关系数(r)>0.999, 线性良好。以5种乳糖衍生物的仪器响应信噪比(S/N)的3倍和10倍计算仪器检出限和仪器定量限, 结合样品前处理过程的稀释倍数(以2000倍计), 计算得到的方法检出限(the method detection limit, MLOD)和方法定量限(the method quantitation limit, MLOQ)。由表2可知, MLODs在3.5~7.5 mg/kg, MLOQs在12.0~25.0 mg/kg。结果表明本方法灵敏, 可用于乳与乳制品的定量分析。
2.4.2 回收率及精密度实验
为验证实际测定过程中, 方法回收率的稳定性, 对乳制品样品进行3水平的加标回收实验, 水平浓度分别为25、100、600 mg/kg, 分别测定3次, 结果见表3。回收率在90.8%~103.3%之间, 满足GB/T 27417—2017《合格评定 化学分析方法确认和验证指南》附录A的表A.1的要求。相对标准偏差在2.8%~5.3%之间, 表明精密度良好, 该方法可满足乳制品中5种乳糖衍生物的分析测定要求。
2.5 方法的实际应用
为了验证方法是否可应用于实际样品的检测中, 实验使用本方法对市售的7个乳与乳制品进行测定, 结果见表4。婴幼儿配方乳粉3的实验图谱见图5, 纯牛奶7加标实验图谱见图谱见图6。
2.6 方法比较分析
为了验证不同方法间的结果一致性, 实验使用本方法与T/TDSTIA 032—2023 《婴幼儿配方乳粉中7种母乳低聚糖的测定 液相色谱-质谱法》方法对2份配方奶粉进行测试(检测的目标物不包括4'-GL、3'-GL、6'-GL), 并与明示质量指标比较, 测试结果满足标示值的≥80%, 且两方法测试结果基本一致, 测试结果见表5。
3 结论与讨论
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本研究采用2-AB衍生化标记荧光基团, 结合高效液相色谱分离技术, 建立了乳与乳制品中5种乳糖衍生物的定量分析方法。本研究优化了仪器条件分离条件, 以及验证了结果, 并对实际样品7份进行检测。方法学评价结果表明, 方法的灵敏度较高, 精密度及回收率良好, 可较准确地反映了市售乳与乳制品中5种乳糖衍生物的实际情况, 可为定量检测功能性乳糖衍生物提供方法参考。本研究未涉及其他类型的样品检测, 乳类基质类型覆盖较少, 方法间比较的样本量较少, 存在一定的局限性, 还需要进一步研究其适用性。
文献
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2025年第16卷第5期
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doi: 10.19812/j.cnki.jfsq11-5956/ts.20241111002
  • 接收时间：2024-11-11
  • 首发时间：2025-07-19
  • 出版时间：2025-03-15
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  • 收稿日期：2024-11-11
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    广州检验检测认证集团有限公司, 广州 511447

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* 黄伟乾(1986—), 男, 工程师, 主要研究方向为食品安全质量检验检测。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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