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Article(id=1248600569011659456, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1248600564427280576, articleNumber=1001-2494(2024)05-0446-05, orderNo=null, doi=null, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1688486400000, receivedDateStr=2023-07-05, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1775619173528, onlineDateStr=2026-04-08, pubDate=1709827200000, pubDateStr=2024-03-08, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1775619173528, onlineIssueDateStr=2026-04-08, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1775619173528, creator=13701087609, updateTime=1775619173528, updator=13701087609, issue=Issue{id=1248600564427280576, tenantId=1146029695717560320, journalId=1190317699101192196, year='2024', volume='59', issue='5', pageStart='377', pageEnd='468', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1775619172436, creator=13701087609, updateTime=1775619904979, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1248603637019202091, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1248600564427280576, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1248603637023396396, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1248600564427280576, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=446, endPage=450, ext={EN=ArticleExt(id=1248600570680992456, articleId=1248600569011659456, tenantId=1146029695717560320, journalId=1190317699101192196, language=EN, title=Determination of Relative Correction Factor Based on Quantitative Nuclear Magnetic Resonance and Chromatography, columnId=null, journalTitle=Chinese Pharmaceutical Journal, columnName=null, runingTitle=null, highlight=null, articleAbstract=

OBJECTIVE To establish a method for determining the relative correction factor (RCF) based on quantitative nuclear magnetic resonance (qNMR) and chromatography, and explore the suitability and accuracy of the method. METHODS The spectral constants of all excited atoms are the same in the qNMR experiment. The ratio of the amount of the substances was calculated by qNMR, and the chromatographic peak area was determined by chromatography. Then the RCF was calculated from the above two results. Taking the correction factor of dimethyl terephthalate relative to coumarin as an example, the reliability of the method was verified. Then the method was used to calculate the RCF of pre-vitamin D3. RESULTS The RCF values obtained by slope ratio method, multi-point method, fusion technology were the same. The experimental result verified the reliability of the method. In addition, this method was used to determine the RCF of pre-vitamin D3 relative to vitamin D3. The results were consistent with those reported in the literature, which further proved that the calculation method was accurate and reliable. CONCLUSION This method provides a new idea for calculating RCF in the absence of reference substance, and solves the problem of difficult determination of RCF of compounds with unstable properties or unavailable standards.

, correspAuthors=Yingchao WANG, 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=Jiaojiao WANG, Zhiwei GE, Shiyan LU, Jingqun YUAN, yu TANG, Yingchao WANG), CN=ArticleExt(id=1248600571767317234, articleId=1248600569011659456, tenantId=1146029695717560320, journalId=1190317699101192196, language=CN, title=基于定量核磁共振与色谱含量测定相结合的相对校正因子测定技术研究, columnId=1190352405612040510, journalTitle=中国药学杂志, columnName=论著, runingTitle=null, highlight=null, articleAbstract=

目的 建立基于定量核磁共振(qNMR)与色谱融合的相对校正因子(RCF)测定方法,探讨方法的可行性与准确性。方法 充分利用qNMR同一次测定中,所有激发原子的光谱常数相同的特点,由核磁信号计算化合物的物质的量之比,运用色谱技术测定色谱峰面积之比,进而将两者结果融合,计算出RCF;以对苯二甲酸二甲酯相对于香豆素的校正因子为例,验证方法的可靠性,并将该方法用于前维生素D3的RCF的计算。结果 实验结果显示,斜率比值法、多点法、融合技术3种方法测得的RCF值相同,验证了方法的可靠性。此外使用该方法测定了前维生素D3相对于维生素D3的RCF,测定结果与文献报道的结果一致,进一步证明了该计算方法准确可靠。结论 液相色谱与定量核磁共振融合技术,为在缺乏对照品的情况下,计算化合物RCF提供了新思路,解决了性质不稳定、对照品不易获得的化合物RCF测定难的问题。

, correspAuthors=王迎超, authorNote=null, correspAuthorsNote=
*王迎超,男,硕士,副研究员 研究方向:药物分析与药物质量控制的研究 Tel: (0571)88982871
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王娇娇,女,硕士研究生,实验师 研究方向:药品和食品质量控制

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王娇娇,女,硕士研究生,实验师 研究方向:药品和食品质量控制

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Drug Stand China (中国药品标准), 2020, 21(2):107-113., articleTitle=Investigation on the calculation methods of Vitamin D assay by HPLC, refAbstract=null), Reference(id=1248642349945999516, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, doi=null, pmid=null, pmcid=null, year=2003, volume=null, issue=11, pageStart=691, pageEnd=693, url=null, language=null, rfNumber=[15], rfOrder=14, authorNames=JIN X L, YANG X P, YANG L, journalName=J Chem Res, refType=null, unstructuredReference=JIN X L, YANG X P, YANG L, et al. Thermal Isomerisation of Vitamin D3 in Dimethyl Sulfoxide[J]. J Chem Res, 2003 (11): 691-693., articleTitle=Thermal Isomerisation of Vitamin D3 in Dimethyl Sulfoxide, refAbstract=null)], funds=[Fund(id=1248642348268277850, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, awardId=LTGY23H290006, language=CN, fundingSource=浙江省自然科学基金项目资助(LTGY23H290006), fundOrder=null, country=null), Fund(id=1248642348364746844, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, awardId=SYBJS202210, language=CN, fundingSource=浙江大学2022年实验技术研究项目资助(SYBJS202210), fundOrder=null, country=null)], companyList=[AuthorCompany(id=1248642344304661325, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, xref=1, ext=[AuthorCompanyExt(id=1248642344313049935, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, companyId=1248642344304661325, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=1 Analysis Center of Agrobiology and Environmental Sciences, Zhejiang University, Hangzhou 310058, China), AuthorCompanyExt(id=1248642344321438544, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, companyId=1248642344304661325, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=1 浙江大学农生环测试中心, 杭州 310058)]), AuthorCompany(id=1248642344396936020, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, xref=2, ext=[AuthorCompanyExt(id=1248642344405324629, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, companyId=1248642344396936020, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=2 College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China), AuthorCompanyExt(id=1248642344413713238, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, companyId=1248642344396936020, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=2 浙江大学药学院, 杭州 310058)])], figs=[ArticleFig(id=1248642347047735309, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=EN, label=Fig.1, caption=Calculation method of chromatographic relative correction factor based on the fusion of quantitative nuclear magnetic resonance and chromatography technology.

cA,cB-the concentration of compound A and B; f-the relative correction factor of compound A relative to B; fA-the correction factor of compound A;fB-the correction factor of compound B; AA,AB-the peak areas of compound A and compound B in the chromatogram; nA,nB-the molar of compound A and B; IA,IB-represent the integral area of the designated peak of compound A and compound B in the hydrogen spectrum; NA,NB -the number of hydrogen atoms represented by the designated peak of compound A and compound B in the hydrogen spectrum.

, figureFileSmall=n7h1ZC1LHaE9pJh3mZcPkA==, figureFileBig=RQLDtUoIQTki1K9PCX6y1A==, tableContent=null), ArticleFig(id=1248642347119038483, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=CN, label=图1, caption=定量核磁共振(qNMR)与色谱融合的色谱相对校正因子(RCF)计算

cA、cB-化合物A和B的物质的量浓度; f-化合物A相对于B的RCF;fA-化合物A的校正因子;fB-化合物B的校正因子;AA、AB-色谱图中化合物A和化合物B的峰面积; nA、nB-化合物A和化合物B的物质的量;IA、IB-氢谱中化合物A和化合物B指定峰的积分面积;NA、NB-氢谱中化合物A和化合物B指定峰代表的氢原子数。

, figureFileSmall=n7h1ZC1LHaE9pJh3mZcPkA==, figureFileBig=RQLDtUoIQTki1K9PCX6y1A==, tableContent=null), ArticleFig(id=1248642347219701787, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=EN, label=Fig.2, caption=Structures of vitamin D3 and pre-vitamin D3, figureFileSmall=oX5wpX/Bjcfw5fxUpLROYw==, figureFileBig=imGloOfD2mH5a/XaUhucrg==, tableContent=null), ArticleFig(id=1248642347324559393, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=CN, label=图2, caption=维生素D3(Vit D3)及前维生素D3(pre-Vit D3)结构, figureFileSmall=oX5wpX/Bjcfw5fxUpLROYw==, figureFileBig=imGloOfD2mH5a/XaUhucrg==, tableContent=null), ArticleFig(id=1248642347437805612, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=EN, label=Fig.3, caption=Chromatogram of Vit D3 solution before and after heating at 80 ℃ (A) and after heating at different temperatures(B) under the condition of avoiding light and isolating air, figureFileSmall=3Qrc9/9a6VjWxM/xc6KJ6Q==, figureFileBig=RpLHXvaTQraPlF6icWVhrA==, tableContent=null), ArticleFig(id=1248642347521691697, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=CN, label=图3, caption=Vit D3溶液避光隔绝空气条件下,80℃加热前、后(A)及不同温度下加热后(B)的色谱图, figureFileSmall=3Qrc9/9a6VjWxM/xc6KJ6Q==, figureFileBig=RpLHXvaTQraPlF6icWVhrA==, tableContent=null), ArticleFig(id=1248642347613966388, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=EN, label=Fig.4, caption=1H-NMR spectra of Vit D3和pre-Vit D3, figureFileSmall=+Z73uv/1RtWXg+IR6ACXNQ==, figureFileBig=nlloZlqvMaxfRZ/AP4ofog==, tableContent=null), ArticleFig(id=1248642347706241087, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=CN, label=图4, caption=Vit D3和pre-Vit D3的1H-NMR谱图, figureFileSmall=+Z73uv/1RtWXg+IR6ACXNQ==, figureFileBig=nlloZlqvMaxfRZ/AP4ofog==, tableContent=null), ArticleFig(id=1248642347773349954, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=EN, label=Tab.1, caption=

The calculated results of RCF of dimethyl terephthalate relative to coumarin.

, figureFileSmall=null, figureFileBig=null, tableContent=
Sample c/μmol·L-1 RCF
Dimethyl terephthalate Coumarin The slope-rate method The multipoint method Fusion technique
ST1 13 17 0.52 0.53
ST2 26 34 0.52 0.51
ST3 39 51 0.52 0.52 0.51
ST4 51 68 0.52 0.52
ST5 77 103 0.52 0.52
Average - - - 0.52 0.52
), ArticleFig(id=1248642347882401862, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=CN, label=表1, caption=

对苯二甲酸二甲酯相对于香豆素的RCF测定结果

, figureFileSmall=null, figureFileBig=null, tableContent=
Sample c/μmol·L-1 RCF
Dimethyl terephthalate Coumarin The slope-rate method The multipoint method Fusion technique
ST1 13 17 0.52 0.53
ST2 26 34 0.52 0.51
ST3 39 51 0.52 0.52 0.51
ST4 51 68 0.52 0.52
ST5 77 103 0.52 0.52
Average - - - 0.52 0.52
), ArticleFig(id=1248642347991453773, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=EN, label=Tab.1, caption=

The calculated results of RCF of pre-Vit D3 relative to Vit D3

, figureFileSmall=null, figureFileBig=null, tableContent=
m(Vit D3)/mg RCF Average RSD/%
0 2.11
1 2.11
2 2.08
3 2.07 2.1 1.2
4 2.09
5 2.05
6 2.05
), ArticleFig(id=1248642348083728463, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1248600569011659456, language=CN, label=表2, caption=

Pre-Vit D3相对于Vit D3的RCF测定结果

, figureFileSmall=null, figureFileBig=null, tableContent=
m(Vit D3)/mg RCF Average RSD/%
0 2.11
1 2.11
2 2.08
3 2.07 2.1 1.2
4 2.09
5 2.05
6 2.05
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基于定量核磁共振与色谱含量测定相结合的相对校正因子测定技术研究
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王娇娇 1 , 葛志伟 1 , 陆诗燕 1 , 袁京群 1 , 唐宇 2 , 王迎超 2, *
中国药学杂志 | 论著 2024,59(5): 446-450
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中国药学杂志 | 论著 2024, 59(5): 446-450
基于定量核磁共振与色谱含量测定相结合的相对校正因子测定技术研究
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王娇娇1, 葛志伟1, 陆诗燕1, 袁京群1, 唐宇2, 王迎超2, *
作者信息
  • 1 浙江大学农生环测试中心, 杭州 310058
  • 2 浙江大学药学院, 杭州 310058

    • 王娇娇,女,硕士研究生,实验师 研究方向:药品和食品质量控制

通讯作者:

*王迎超,男,硕士,副研究员 研究方向:药物分析与药物质量控制的研究 Tel: (0571)88982871
Determination of Relative Correction Factor Based on Quantitative Nuclear Magnetic Resonance and Chromatography
Jiaojiao WANG1, Zhiwei GE1, Shiyan LU1, Jingqun YUAN1, yu TANG2, Yingchao WANG2, *
Affiliations
  • 1 Analysis Center of Agrobiology and Environmental Sciences, Zhejiang University, Hangzhou 310058, China
  • 2 College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China
出版时间: 2024-03-08
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摘要
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目的 建立基于定量核磁共振(qNMR)与色谱融合的相对校正因子(RCF)测定方法,探讨方法的可行性与准确性。方法 充分利用qNMR同一次测定中,所有激发原子的光谱常数相同的特点,由核磁信号计算化合物的物质的量之比,运用色谱技术测定色谱峰面积之比,进而将两者结果融合,计算出RCF;以对苯二甲酸二甲酯相对于香豆素的校正因子为例,验证方法的可靠性,并将该方法用于前维生素D3的RCF的计算。结果 实验结果显示,斜率比值法、多点法、融合技术3种方法测得的RCF值相同,验证了方法的可靠性。此外使用该方法测定了前维生素D3相对于维生素D3的RCF,测定结果与文献报道的结果一致,进一步证明了该计算方法准确可靠。结论 液相色谱与定量核磁共振融合技术,为在缺乏对照品的情况下,计算化合物RCF提供了新思路,解决了性质不稳定、对照品不易获得的化合物RCF测定难的问题。

定量核磁共振  /  液相色谱法  /  相对校正因子  /  维生素D3  /  前维生素D3

OBJECTIVE To establish a method for determining the relative correction factor (RCF) based on quantitative nuclear magnetic resonance (qNMR) and chromatography, and explore the suitability and accuracy of the method. METHODS The spectral constants of all excited atoms are the same in the qNMR experiment. The ratio of the amount of the substances was calculated by qNMR, and the chromatographic peak area was determined by chromatography. Then the RCF was calculated from the above two results. Taking the correction factor of dimethyl terephthalate relative to coumarin as an example, the reliability of the method was verified. Then the method was used to calculate the RCF of pre-vitamin D3. RESULTS The RCF values obtained by slope ratio method, multi-point method, fusion technology were the same. The experimental result verified the reliability of the method. In addition, this method was used to determine the RCF of pre-vitamin D3 relative to vitamin D3. The results were consistent with those reported in the literature, which further proved that the calculation method was accurate and reliable. CONCLUSION This method provides a new idea for calculating RCF in the absence of reference substance, and solves the problem of difficult determination of RCF of compounds with unstable properties or unavailable standards.

quantitative nuclear magnetic resonance  /  liquid chromatography  /  relative correction factor  /  vitamin D3  /  pre-vitamin D3
王娇娇, 葛志伟, 陆诗燕, 袁京群, 唐宇, 王迎超. 基于定量核磁共振与色谱含量测定相结合的相对校正因子测定技术研究. 中国药学杂志, 2024 , 59 (5) : 446 -450 .
Jiaojiao WANG, Zhiwei GE, Shiyan LU, Jingqun YUAN, yu TANG, Yingchao WANG. Determination of Relative Correction Factor Based on Quantitative Nuclear Magnetic Resonance and Chromatography[J]. Chinese Pharmaceutical Journal, 2024 , 59 (5) : 446 -450 .
正文
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目前文献报道的相对校正因子(relative correction factor,RCF)常用计算方法有:斜率比值法、多点法、吸光系数比值法[1]。这些方法建立时都需要用到对照品,但以下3类对照品不仅难以购买而且价格昂贵:①不易获得化合物,例如低含量植物活性成分、药物杂质等;②不稳定化合物,如受到光、热等作用易发生构型转化的顺反异构体等;③个性化需求的特殊化合物,如特殊催化剂、荧光传感器等。
不同于常用的含量测定仪器分析手段色谱法(如液相色谱法和气相色谱法)、光谱法(如紫外吸收光谱法和荧光光谱法)、质谱法以及各种联用技术[2-3],定量核磁共振(quantitative nuclear magnetic,qNMR)的分析对象为原子,不需要和分析物完全相同的参考物质,无需制作标准曲线,只需含有相同原子的化合物做内标即可实现绝对定量,已广泛用于药物分析[4-6]、食品分析[7]和参考物质质量控制[3]等领域。根据国际计量委员会对基准分析方法的定义,qNMR已满足基准定量方法的要求[8-11]。
鉴于qNMR同一次测定中,所有激发原子的光谱常数相同的特点,可采用稳定价廉的化合物或体系中其他化合物作为内标,由核磁信号计算其与待测化合物的物质的量之比,运用色谱技术测定内标与待测化合物的色谱峰面积之比,进而将两者结果融合,即可计算出待测有机化合物的色谱RCF,从而达到由易得、稳定、价廉的化合物来测定不稳定、不易获得、昂贵的化合物RCF的目的。
活性维生素D类化合物具有共轭三烯结构,可热异构化为前维生素D[12-13],且在避光、无氧、加热80 ℃条件下,部分维生素D类化合物定量转化为前维生素D,无其他杂质产生[14]。原型结构与前体结构是一对异构体,在溶液中发生可逆的异构化,这与温度和时间有关,因此前维生素D的制备及定量测定在维生素D类化合物含量测定中都是共性的难点问题[12]。
本研究首先分别使用斜率比值法、多点法、液相色谱与定量核磁共振氢谱(1H-qNMR)融合技术3种方法测定了对苯二甲酸二甲酯相对于香豆素的校正因子,验证了方法的可行性。在此基础上,采用融合技术测定了前维生素D3(pre-Vit D3)相对于维生素D3(Vit D3)的RCF,结果与文献一致。本方法通过色谱技术和定量核磁共振技术的融合为RCF的测定提供了新思路,同时解决了不稳定、不易获得、昂贵的化合物测定难的问题。
1 仪器与试剂
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JNM-ECZ500R/M1型全数字化超导核磁共振波谱仪(日本JEOL公司);LC-20AD型高效液相色谱仪(日本岛津公司);AL104型万分之一天平(德国METTLER TOLEDO公司);DHG-9053A型电热恒温鼓风干燥箱。
氘代二甲基亚砜(DMSO-d6,99.9% D+0.03% TMS,美国剑桥同位素实验室公司);甲醇(色谱纯);对苯二甲酸二甲酯、香豆素(分析纯);Vit D3(98%,上海阿拉丁生化科技股份有限公司);实验用水为超纯水。
2 方法
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2.1 融合技术方法验证
2.1.1 方法验证样本制备
准确称取对苯二甲酸二甲酯和香豆素各5 mg溶于1 mL DMSO-d6中,随后用DMSO-d6稀释成不同浓度标准溶液(样品浓度见表1)用于1H-qNMR测定。同时将系列标准溶液用乙腈稀释100倍后用液相色谱测定各化合物色谱峰面积。
2.1.2 1H-qNMR测定
1H-qNMR采集条件:脉冲宽度6.527 μs,脉冲角度90°,弛豫时间40 s,扫描次数16次。数据使用JEOL Delta 6.0.0软件处理,线宽因子0.2 Hz,进行手动相位校正和基线校正,积分时,选定积分区域,每个峰积分3~5次,相对标准偏差(RSD)小于1%时取平均值[5]。
2.1.3 高效液相色谱条件
岛津 InertSustain C18柱(4.6 mm×250 mm,5 μm);流动相:体积分数80%乙腈水溶液;流速:1.0 mL·min-1;柱温:40 ℃;检测波长254 nm;进样量:10 μL。
2.2 pre-Vit D3的RCF测定
2.2.1 供试品溶液制备
精密称取Vit D3 10 mg,置于棕色小瓶中,加入1.0 mL DMSO-d6,充氮气排除空气,置于80 ℃电热恒温鼓风干燥箱中,避光加热1 h后取出,迅速冷却,用于1H-qNMR测定。同时用甲醇稀释100倍后用液相色谱测定Vit D3和pre-Vit D3的色谱峰面积。
2.2.2 1H-qNMR测定
1H-qNMR采集条件:脉冲宽度6.527 μs,脉冲角度90°,弛豫时间10 s,扫描次数64次。数据使用JEOL Delta 6.0.0软件处理,线宽因子0.2 Hz,进行手动相位校正和基线校正,积分时,选定积分区域,每个峰积分3~5次,相对标准偏差(RSD)小于1%时取平均值[5]。
2.2.3 高效液相色谱条件
YMC Carotenoid柱(4.6 mm×250 mm,5 μm);流动相:体积分数98%甲醇水溶液;流速:1.0 mL·min-1;柱温:40 ℃;检测波长265 nm;进样量:10 μL。
3 结果与讨论
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3.1 qNMR与色谱融合的色谱相对RCF计算简介
一般常用的气相色谱和液相色谱的检测器对不同物质的响应值不同,但在1H-qNMR同一次测定中,所有激发氢原子的光谱常数相同。通过1H-qNMR中峰面积的比值和代表的原子数,可以得到溶液中不同化合物的物质的量之比,结合色谱测定的峰面积之比,进而计算RCF(无特殊说明情况下,本研究RCF均为相对摩尔校正因子)。从而达到由易得、稳定、价廉的化合物来测定不稳定、不易获得、昂贵的化合物RCF的目的,见图1。
3.2 融合技术方法验证
3.2.1 实验参数的影响
分别考察了不同脉冲角度、弛豫时间、扫描次数对1H-qNMR积分面积的影响。当脉冲角度为90°,弛豫时间≥40 s,扫描次数≥16次时,信噪比>150且指定信号积分面积之比趋于稳定。
3.2.2 不同方法测定的RCF值比较
运用传统的斜率比值法、多点法以及本研究提出的融合技术测定的对苯二甲酸二甲酯相对于香豆素的RCF均为0.52,结果见表1。表明将qNMR与色谱技术融合用于RCF测定的方案是可行的,测定结果是准确的。
3.3 pre-Vit D3相对校正因子计算
3.3.1 pre-Vit D3制备条件优化
Vit D3具有共轭三烯结构,避光隔绝空气条件下能够热异构化为pre-Vit D3(图2)。Vit D3与pre-Vit D3之间的转变是可逆的,升高温度有利于pre-Vit D3的生成,但Vit D3为优势构象,而pre-Vit D3为非优势构象,溶液中非优势构象易向优势构象转化,最终达到动态平衡[12]。考察了在避光隔绝空气条件下,不同温度加热不同时间时溶液中Vit D3热异构化的比例。结果显示,分别在60、80、120 ℃条件下加热1.5 h后溶液中pre-Vit D3峰面积占Vit D3和pre-Vit D3面积总和的比例分别为2.1%、8.2%、8.2%,但是120 ℃条件下加热样品的色谱图中出现较多杂峰(图3),据文献[15]报道100~180 ℃时Vit D3会不可逆地生成焦胆钙化甾醇、异焦胆钙化甾醇、异维生素D3、异速甾醇等。随后将样品在避光、隔绝空气、80 ℃下加热1、2、3 h,经液相色谱分析发现,随着加热时间的增加,pre-Vit D3峰面积占Vit D3和pre-Vit D3峰面积总和的比例均为8.2%。因此,pre-Vit D3制备的最佳条件为:避光、隔绝空气、80 ℃下加热1 h。
3.3.2 1H-qNMR中定量峰选择
在进行qNMR分析前先对其质子峰进行归属,明确每个信号峰所对应的质子数,根据文献[15]及谱图分析,将氢原子δ 6.17、5.95和5.02分别归属为Vit D3的H-6、H-7、H-19质子信号峰,将氢原子δ5.89、5.63和5.45分别归属为pre-Vit D3的H-6、H-7、H-9质子信号峰(图4)。qNMR分析优先选择耦合裂分较少且与相邻质子峰分离较好的峰作为定量峰,综合考虑选择Vit D3的H-19(δ5.02)和pre-Vit D3的H-9(δ5.45)作为定量峰。
3.3.3 1H-qNMR实验参数优化
弛豫时间对核磁共振信号积分结果的准确性影响较大,qNMR实验的弛豫时间通常设定不低于纵向弛豫时间的5倍,采用反转恢复法测定化合物质子的纵向弛豫时间,Vit D3的H-19和pre-Vit D3的H-9的弛豫时间分别为0.91、1.35 s。弛豫时间设定过长会增加分析时间,在保证采样质子能够得到充分弛豫的同时兼顾分析时间,选择纵向弛豫时间为10 s。扫描次数增加会提高信号峰的信噪比和稳定性但延长测试时间,考虑到Vit D3和pre-Vit D3的稳定性。本研究确定的扫描次数为64次,每次分析需15 min左右。
3.3.4 pre-Vit D3的RCF计算结果
按照“2.3”项下方法制备6份样品并根据图1中的公式计算pre-Vit D3相对于Vit D3RCF,平均值为2.1,RSD为1.5%,表明方法重复性良好。
为了验证方法准确度,向含有pre-Vit D3和Vit D3的溶液中加入不同量的Vit D3,并根据图1中的公式计算pre-Vit D3相对于Vit D3的RCF。具体操作为:称取Vit D3 50 mg,置于棕色小瓶中,加入5.0 mL DMSO-d6,充氮气排出空气,置于80 ℃电热恒温鼓风干燥箱中,避光加热1 h后取出,迅速冷却,平行取上述溶液0.6 mL7份,分别加入0、1、2、3、4、5、6 mg Vit D3,之后测定并计算RCF,结果见表2,7份样品计算的RCF平均值为2.1,RSD为1.2%。表明方法准确可靠,且结果与文献[14]报道一致。
4 结论
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目前,基于qNMR与色谱融合的有机化合物RCF测定技术的研究未见报道,该技术为难以获得对照品、制备成本高、不稳定、个性化的特殊化合物RCF的测定提供了新思路,同时该方法操作简单,便于实现,拓展了qNMR技术的使用范围,有望解决药物中间体、药物制剂中无对照品化合物含量测定的难题。此外,该技术还有望用于中药“一测多评”中RCF的测定。
基金
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  • 浙江省自然科学基金项目资助(LTGY23H290006)
  • 浙江大学2022年实验技术研究项目资助(SYBJS202210)
文献
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参考文献 引证文献
排序方式：
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2024年第59卷第5期
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  • 接收时间：2023-07-05
  • 首发时间：2026-04-08
  • 出版时间：2024-03-08
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  • 收稿日期：2023-07-05
基金
浙江省自然科学基金项目资助(LTGY23H290006)
浙江大学2022年实验技术研究项目资助(SYBJS202210)
作者信息
    1 浙江大学农生环测试中心, 杭州 310058
    2 浙江大学药学院, 杭州 310058

通讯作者:

*王迎超,男,硕士,副研究员 研究方向:药物分析与药物质量控制的研究 Tel: (0571)88982871
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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
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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
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