Skip to main content
SpringerLink
Log in

ZIF-based boronic acid functionalized metal-organic frameworks for the enrichment of cis-diol-containing luteolin from food samples prior to  HPLC

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

Abstract

Zeolite imidazole framework-based boronic acid-functionalized metal-organic frameworks (ZIF-67@PDA@BA-Zr-MOFs) were developed as an adsorbent for solid phase extraction (SPE) of luteolin (LTL) from peanut shell samples. Herein, ZIF-67 as a support matrix, polydopamine (PDA) as a coating to introduce amino and hydroxyl groups on the matrix surface to fix metal-organic frameworks (MOFs), zirconium tetrachloride (ZrCl4) as a precursor, terephthalic acid (TPA), and 3-carboxyphenylboronic acid (3-CPBA) as the mutual organic building blocks, and 3-CPBA was also a boronate affinity functional monomer. The effects of synthesis conditions, SPE conditions, selectivity, competitivity, reproducibility, and reusability were evaluated in detail. Under the optimal conditions, the maximum adsorption capacity is 71.4 mg g−1. The utility of ZIF-67@PDA@BA-Zr-MOFs as an adsorbent for SPE of LTL is supported by the presence of the abundant pore structure, as well as the boronate affinity sites facilitated the rapid binding of the adsorbent to the template. The concentration of the extracted LTL was determined by the high-performance liquid chromatography-ultraviolet (HPLC-UV), with calibration plots being linear in the concentration range 0.05–100 mg L−1 and a limit of detection (LOD) of 0.035 mg L−1. The method was applied to determine the LTL in peanut shell samples and recovered the target analyte in the range 85.6% to 99.2% (the standard deviations are less than 3.3%, n = 3). In addition, we incorporated boronate affinity and MOFs material into an SPE system to provide a promising strategy to detect other cis-diol-containing analytes in the complex matrix.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Guo BL, Tong YK, Zhang BY, Tian MM (2021) Double affinity based molecularly imprinted polymers for selective extraction of luteolin: a combination of synergistic metal chelating and boronate affinity. Microchem J 160:105670

    Article  CAS  Google Scholar 

  2. Dean LL (2020) Extracts of peanut skins as a source of bioactive compounds: methodology and applications. Appl Sci 10:8546

    Article  CAS  Google Scholar 

  3. Pan LS, Zhao XY, Zeng S, Xiang FY, Zhao GG, Li YF (2019) Extraction of luteolin from peanut shells by a hydrophilic ionic liquid-based microwave-assisted method. Chemistry Select 4:13589–13595

    CAS  Google Scholar 

  4. Pan JM, Huang XB, Gao L, Peng YX, Liu SC, Gu RX (2017) Experimental investigation of a natural favonoid adsorption on macroporous polymers with intrinsic cis-diol moieties recognition function: Static and dynamic methods. Chem Eng J 312:263–274

    Article  CAS  Google Scholar 

  5. Cao XX, Wang M, Sun LL, Ren XL, Pei GS (2018) Preferential adsorption of flavonoids from peanut shell by amino-modified Fe3O4 nanoparticles (MNP-NH2). J Sci Food Agric 98:3588–3594

    Article  CAS  Google Scholar 

  6. Jia Q, Ma Y, Peng YX, Liu YH, Zhang WL (2018) Selective recognition and separation of luteolin based on the molecular imprinted hollow SnO2 and boronate affinity. Chem Eng J 342:293–303

    Article  CAS  Google Scholar 

  7. Bai X, Liu SC, Liu JX, Ma Y, Zhang WL, Pan JM (2018) Specific uptake luteolin by boronate affinity-based single-hole hollow imprinted polymers sealed in dialysis bags. Chem Eng J 353:911–919

    Article  CAS  Google Scholar 

  8. Liu SC, Pan JM, Zhu HJ, Pan GQ, Qiu FX, Meng MJ, Yao JT, Yuan D (2016) Graphene oxide based molecularly imprinted polymers with double recognition abilities: the combination of covalent boronic acid and traditional non-covalent monomers. Chem Eng J 290:220–231

    Article  CAS  Google Scholar 

  9. Raabová H, Erben J, Chvojka J, Solich P, Švec F, Šatínský D (2020) The role of pKa, log P of analytes, and protein matrix in solid-phase extraction using native and coated nanofibrous and microfibrous polymers prepared via meltblowing and combined meltblowing/electrospinning technologies. J Chromatogr A 1631:461580

    Article  Google Scholar 

  10. Ali MM, Hussain D, Xu B, Sun TQ, Du ZX (2020) Diethylenetriamine assisted functionalization of boronic acid on poly GMA-MAA-DVB for selective enrichment of glycoproteins and glycopeptides. Talanta 219:121178

    Article  Google Scholar 

  11. Deng YN, Gao Q, Ma J, Wang CZ, Wei YM (2018) Preparation of a boronate affinity material with ultrahigh binding capacity for cis-diols by grafting polymer brush from polydopamine-coated magnetized graphene oxide. Microchim Acta 185:189

    Article  Google Scholar 

  12. Ali MM, Hussain D, Tang Y, Sun XC, Shen ZC, Zhang FX, Du ZX (2021) Boronoisophthalic acid as a novel affinity ligand for the selective capture and release of glycoproteins near physiological pH. Talanta 225:121896

    Article  CAS  Google Scholar 

  13. Li DJ, Xia HJ, Wang L (2018) Branched polyethyleneimine-assisted boronic acid-functionalized silica nanoparticles for the selective enrichment of trace glycoproteins. Talanta 184:235–243

    Article  CAS  Google Scholar 

  14. Yao JT, Ma Y, Liu JX, Liu SC, Pan JM (2019) Janus-like boronate affinity magnetic molecularly imprinted nanobottles for specific adsorption and fast separation of luteolin. Chem Eng J 356:436–444

    Article  CAS  Google Scholar 

  15. Muhammad SS, Blagojce J, Parul M, Batool F, Dilshad H, Fahmida J, Muhammad NA, Tara LP, Muhammad NH (2020) Glycosylation heterogeneity and low abundant serum glycoproteins MS analysis by boronic acid immobilized Fe3O4@1,2-Epoxy-5-Hexene/DVB magnetic core shell nanoparticles. Microchem J 159:105351

    Article  Google Scholar 

  16. Zhang RQ, Wang Z, Wang TF, Su P, Yang Y (2020) Boronic acid-decorated metal-organic frameworks modified via a mixed-ligand strategy for the selective enrichment of cis-diol containing nucleosides. Anal Chim Acta 1106:42–51

    Article  CAS  Google Scholar 

  17. Tan W, Chen T, Liu WR, Ye FG, Zhao SL (2021) Design and fabrication of boric acid functionalized hierarchical porous metal-organic frameworks for specific removal of cis-diol-containing compounds from aqueous solution. Appl Surf Sci 535:147714

    Article  CAS  Google Scholar 

  18. Bie ZJ, Huang AL, Zhang YN, Chen Y (2019) Boronate affinity Metal-Organic frameworks for highly efficient cis-diol molecules in-situ enrichment and surface-assisted laser desorption/ionization mass spectrometric detection. Anal Chim Acta 1065:40–48

    Article  CAS  Google Scholar 

  19. Ibrahim AO, Adegoke KA, Adegoke RO, AbdulWahab YA, Oyelami VB, Adesina MO (2021) Adsorptive removal of different pollutants using metal-organic framework adsorbents. J Mol Liq 333:115593

    Article  CAS  Google Scholar 

  20. Wang C, Lin G, Zhao JL, Wang SX, Zhang LB, Xi YH, Li XT, Ying Y (2020) Highly selective recovery of Au(III) from wastewater by thioctic acid modified Zr-MOF: experiment and DFT calculation. Chem Eng J 380:122511

    Article  CAS  Google Scholar 

  21. Abrar M, Dilshad H, Batool F, Muhammad A, Muhammad NA, Muhammad NH (2019) Gallic acid functionalized UiO-66 for the recovery of ribosylated metabolites from human urine samples. Talanta 201:23–32

    Article  Google Scholar 

  22. Khalil A, Muhammad AN, Ahmad KQ, Ejaz H, Tayyaba N, Muhammad SJ, Syed SAS, Muhammad KT, Shahid H, Naseem AK, Habib-ur-Rehman S, Muhammad A (2020) Engineering of Zirconium based metal-organic frameworks (Zr-MOFs) as efficient adsorbents. Mater Sci Eng B Adv 262:114766

    Article  Google Scholar 

  23. Zhu XY, Gu JL, Zhu JY, Li YS, Zhao LM, Shi JL (2015) Metal-organic frameworks with boronic acid suspended and their implication for cis-diol moieties binding. Adv Funct Mater 25:3847–3854

    Article  CAS  Google Scholar 

  24. Xie YQ, Liu QJ, Li Y, Deng CH (2018) Core-shell structured magnetic metal-organic framework composites for highly selective detection of N-glycopeptides based on boronic acid affinity chromatography. J Chromatogr A 1540:87–93

    Article  CAS  Google Scholar 

  25. Liu SC, Ma Y, Gao L, Pan JM (2018) pH-responsive magnetic metal-organic framework nanocomposite: a smart porous adsorbent for highly specific enrichment of cis-diol containing luteolin. Chem Eng J 341:198–207

    Article  CAS  Google Scholar 

  26. Pan YN, Guo XM, Li SS, Liu XY, Zhang HX (2013) Boronate-decorated porous carbon material derived from zinc-based metal-organic framework for enrichment of cis-diol-containing nucleosides. New J Chem 42:2288–2294

    Article  Google Scholar 

  27. Liu SC, Pan JM, Ma Y, Qiu FX, Niu XH, Zhang T, Yang LL (2016) Three-in-one strategy for selective adsorption and effective separation of cis-diol containing luteolin from peanut shell coarse extract using PU/GO/BA-MOF composite. Chem Eng J 306:655–666

    Article  CAS  Google Scholar 

  28. Xia BY, Yan Y, Li N, Wu HB, Lou XW(D), Wang X (2016) A metal-organic framework-derived bifunctional oxygen electrocatalyst. Nat Energy 1:15006

    Article  CAS  Google Scholar 

  29. Gao ZG, Zhang JQ, Zhang SJ, Lan D, Zhao ZH, Kou KC (2020) Strategies for electromagnetic wave absorbers derived from zeolite imidazole framework (ZIF-67) with ferrocene containing polymers. Polymer 202:122679

    Article  CAS  Google Scholar 

  30. Yu ZB, Qian L, Zhong T, Ran Q, Huang J, Hou YP, Li FY, Li MJ, Sun QQ, Zhang HQ (2020) Enhanced visible light photocatalytic activity of CdS through controllable self-assembly compositing with ZIF-67. Mol Catal 485:110797

    Article  CAS  Google Scholar 

  31. Martínez-Pérez-Cejuela H, Mompó-Roselló Ó, Crespí-Sánchez N, Cabello CP, Catalá-Icardo M, Simó-Alfonso EF, Herrero-Martínez JM (1631) Determination of benzomercaptans in environmental complex samples by combining zeolitic imidazolate framework-8-based solid-phase extraction and high-performance liquid chromatography with UV detection. J Chromatogr A 2020:461580

  32. Li YF, Yan XL, Hu XY, Feng R, Zhou M (2019) Trace pyrolyzed ZIF-67 loaded activated carbon pellets for enhanced adsorption and catalytic degradation of Rhodamine B in water. Chem Eng J 375:122003

    Article  CAS  Google Scholar 

  33. Tong YK, Zhang BY, Guo BL, Wu WJ, Jin YX, Geng F, Tian MM (1637) Gallic acid-affinity molecularly imprinted polymer adsorbent for capture of cis-diol containing Luteolin prior to determination by high performance liquid chromatography. J Chromatogr A 2021:461829

  34. Gao D, Yang FQ, Xia ZN, Zhang QH (2016) Molecularly imprinted polymer for the selective extraction of luteolin from Chrysanthemum morifolium Ramat. J Sep Sci 39:2885–3092

    Google Scholar 

  35. Wang N, Zhou XS, Cui B (2019) Synthesis of a polymeric imidazolium-embedded octadecyl ionic liquid-grafted silica sorbent for extraction of flavonoids. J Chromatogr A 1606:460376

    Article  CAS  Google Scholar 

  36. Wang ZB, Sun R, Wang YP, Li N, Lei L, Yang X, Yu AM, Qiu FP, Zhang HQ (2014) Determination of phenolic acids and flavonoids in raw propolis by silica-supported ionic liquid-based matrix solid phase dispersion extraction high performance liquid chromatography-diode array detection. J Chromatogr B 969:205–212

    Article  CAS  Google Scholar 

  37. Hadjmohammadi M, Karimiyan H, Sharifi V (2013) Hollow fibre-based liquid phase microextraction combined with high-performance liquid chromatography for the analysis of flavonoids in Echinophora platyloba DC. and Mentha piperita. Food Chem 141:731–735

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the University Nursing Program for Young Scholars with Creative Talents in Heilongjiang Province, China (No. UNPYSCT-2018179).

Author information

Author notes

  1. Bailin Guo and Xue Chen contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Photochemical Biomaterials and Energy Storage Materials, Heilongjiang Province, College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin, 150025, People’s Republic of China

    Bailin Guo, Xue Chen, Baoyue Zhang, Yukui Tong, Sheng Bi & Miaomiao Tian

  2. Ruyuan Hec Pharm Co., Ltd. Guangdong Province, Shaoguan, 512700, People’s Republic of China

    Jianghua He

Authors
  1. Bailin Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xue Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jianghua He
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Baoyue Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yukui Tong
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Sheng Bi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Miaomiao Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Miaomiao Tian.

Ethics declarations

Conflict of interest

The authors declare that they have no competing interests.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

ESM 1

(DOC 3.46 mb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Guo, B., Chen, X., He, J. et al. ZIF-based boronic acid functionalized metal-organic frameworks for the enrichment of cis-diol-containing luteolin from food samples prior to  HPLC. Microchim Acta 188, 229 (2021). https://doi.org/10.1007/s00604-021-04881-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00604-021-04881-3

Keywords

Search

Navigation