Quinolinecarboxylic Acid-linked Covalent Organic Framework Microsphere for On-line Solid Phase Extraction of Four Aflatoxins

WANG Rong-yu; LIU Jie; ZHOU Jing; LI Tao; WANG Xiao; JI Wen-hua

doi:10.12452/j.fxcsxb.240720244

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Quinolinecarboxylic Acid-linked Covalent Organic Framework Microsphere for On-line Solid Phase Extraction of Four Aflatoxins

Scientific Papers | 更新时间：2025-01-03

- Quinolinecarboxylic Acid-linked Covalent Organic Framework Microsphere for On-line Solid Phase Extraction of Four Aflatoxins
- Journal of Instrumental Analysis Vol. 44, Issue 1, Pages: 163-171(2025)
- 作者机构：
  
  1.齐鲁工业大学（山东省科学院）山东省分析测试中心天然产物分离提取共性技术创新与应用山东省工程研究中心，山东济南 250014
  2.山东明仁福瑞达制药股份有限公司，山东济南 250014
  3.山东蓝城分析测试有限公司，山东济南 250100
- 作者简介：
- 基金信息：
- DOI：10.12452/j.fxcsxb.240720244
  CLC： O657.7;TS207.3
- Published：15 January 2025，
  
  Received：20 July 2024，
  
  Revised：27 August 2024，
- 稿件说明：
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王荣雨,刘杰,周静,李涛,王晓,纪文华.喹啉羧酸共价有机框架微球在线固相萃取4种黄曲霉毒素[J].分析测试学报,2025,44(01):163-171.

WANG Rong-yu,LIU Jie,ZHOU Jing,LI Tao,WANG Xiao,JI Wen-hua.Quinolinecarboxylic Acid-linked Covalent Organic Framework Microsphere for On-line Solid Phase Extraction of Four Aflatoxins[J].Journal of Instrumental Analysis,2025,44(01):163-171.
王荣雨,刘杰,周静,李涛,王晓,纪文华.喹啉羧酸共价有机框架微球在线固相萃取4种黄曲霉毒素[J].分析测试学报,2025,44(01):163-171. DOI： 10.12452/j.fxcsxb.240720244.

WANG Rong-yu,LIU Jie,ZHOU Jing,LI Tao,WANG Xiao,JI Wen-hua.Quinolinecarboxylic Acid-linked Covalent Organic Framework Microsphere for On-line Solid Phase Extraction of Four Aflatoxins[J].Journal of Instrumental Analysis,2025,44(01):163-171. DOI： 10.12452/j.fxcsxb.240720244.

摘要

以1，3，5-三（4-氨基苯基）苯、联苯二甲醛、丙酮酸为合成反应单体，氨基磺酸为催化剂，利用Doebner串联反应成功制备了具有喹啉羧酸骨架的共价有机框架（QCA-COF）微球。通过优化反应条件发现，采用1，4-二氧六环-乙腈溶液（1∶4，体积比）作为反应溶剂时，可获得具有微米级粒径的微球。采用扫描电子显微镜、红外光

谱、X射线粉末衍射、N

吸脱附实验对QCA-COF微球的结构进行表征。由于QCA-COF微球具有芳环、喹啉基团、羧基等官能团，可通过氢键、π-π等多重相互作用与黄曲霉毒素进行吸附，其吸附能力优于C

、PSA以及GCB等商用材料。将QCA-COF材料作为在线固相萃取柱的填料，详细优化了在线固相萃取条件。将在线固相萃取柱与高效液相色谱联用，建立了4种黄曲霉毒素的检测方法，检出限为0.024~0.030 ng·g

-1

。经方法学验证，该方法具有较好的回收率（82.5%~105%）和精密度（4.3%~10%，

=6），适用于花生、小麦、陈皮、杏仁、决明子等食品与中药材中4种黄曲霉毒素的测定。

Abstract

In this study，on-line solid phase extraction（SPE） based on quinolinecarboxylic acid-linked covalent organic framework（QCA-COF） microsphere was developed. On-line SPE coupled with high performance liquid chromatography（HPLC） was used for the determination of four aflatoxins（AFs） in food samples and Chinese medicinal herbs，including AFB

，AFB

，AFG

and AFG

. QCA-COF microsphere was successfully synthesized via the Doebner multicomponent reaction. For this process，1，3，5-tris（4-aminophenyl）benzene，4，4’-biphenyldicarboxaldehyde and pyruvic acid were used as the synthetic monomer under the catalysis of sulfamic acid. QCA-COF microsphere was characterized by scanning electron microscope，Fourier transform infrared spectroscopy，powder X-ray diffraction，and N

adsorption-desorption isotherms. The results showed that micro-sized QCA-COF microsphere was obtained in a solution of 1，4-dioxane-acetonitrile（1∶4，volume ratio）. The structure of QCA-COF has aromatic rings，pyridine groups and —COOH groups，which permits multiple binding interactions with aflatoxins. Based on their binding groups，QCA-COF exhibited excellent on-line SPE capability compared to the commercial materials，such as C

，PSA and GCB. The extraction parameters of the adsorption and elution processes were optimized in detail，including flow rates of loading，eluting solvent，volume of eluting solvent，and flow rates of elution. The optimal conditions were shown as follows：loading flow rate，0.4 mL·min

-1

；eluting solvent，300 μL of 0.1% acetic acid in methanol；elution flow rate，0.2 mL

·min

-1

. Under the optimized conditions，the developed on-line SPE coupled with HPLC method provided good recovery（82.5%-105%），good precision（4.3%-10%，

=6），and low limit of detection（0.024-0.030 ng·g

-1

）. The introduced method was successfully used to analyze four AFs in peanuts，wheat，orange peel，almonds and cassia seed.

关键词

黄曲霉毒素在线固相萃取共价有机框架高效液相色谱

Keywords

aflatoxinson-line solid phase extractioncovalent organic frameworkhigh performance liquid chromatography

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