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Analytical and Bioanalytical Chemistry

, Volume 411, Issue 7, pp 1409–1419 | Cite as

Development of a nitrogen-rich hyperbranched polymer as adsorbent for enrichment and determination of auxins in plants

  • Rui Zhang
  • Shanshan Li
  • Xiaoyan LiuEmail author
  • Haixia Zhang
Research Paper

Abstract

In this study, a novel nitrogen-rich hyperbranched polymer was designed and synthesized via one-step precipitation copolymerization strategy. As possessing the lone-pair-electron-containing nitrogen atoms and positive-charged amine groups, as well as π electron–conjugated system, the prepared polymer displayed a strong tendency to adsorb protons acid, and negative-charged and conjugated compounds according to acid–base interaction, electrostatic interaction, and π–π stacking interaction. Based on these properties, a novel approach for assembling the proposed polymer coupled with high-performance liquid chromatography was successfully employed for selective enrichment and determination of auxins in plants. The extraction and desorption conditions were evaluated and the limits of detection and the limits of quantification of the proposed method were in the range of 0.15–0.29 μg L−1 and 0.49–0.98 μg L−1 for the four auxins based on the signal-to-noise ratio of 3:1 and 10:1, respectively. The recoveries of the target auxins from spiked plant samples were in the range from 85.0 to 116.3% with relative standard deviations lower than 9.6%. This study presented an inspiring thought for the construction of the versatile polymer adsorbent with highly efficient capturing of analytes from complex samples.

Graphical abstract

Keywords

Hyperbranched polymer Solid-phase extraction Auxins High-performance liquid chromatography 

Notes

Funding information

The authors received support from the National Natural Science Foundation of China (NSFC) Fund (No. 21575055) and the Fundamental Research Funds for the Central Universities (lzujbky–2017–k09).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

216_2018_1571_MOESM1_ESM.pdf (1.2 mb)
ESM 1 (PDF 1189 kb)

References

  1. 1.
    Ulger S, Sonmez S, Karkacier M, Ertoy N, Akdesir O, Aksu M. Determination of endogenous hormones, sugars and mineral nutrition levels during the induction, initiation and differentiation stage and their effects on flower formation in olive. Plant Growth Regul. 2004;42:89–95.CrossRefGoogle Scholar
  2. 2.
    Way JM. In, New York, NY, 1969. Residue reviews / Rückstands-Berichte. Springer New York, pp. 37–62.Google Scholar
  3. 3.
    Esparza X, Moyano E, Cosialls JR, Galceran MT. Determination of naphthalene-derived compounds in apples by ultra-high performance liquid chromatography-tandem mass spectrometry. Anal Chim Acta. 2013;782:28–36.CrossRefGoogle Scholar
  4. 4.
    Susawaengsup C, Rayanakorn M, Wongpornchai S, Wangkarn S. Investigation of plant hormone level changes in shoot tips of longan (Dimocarpus longan Lour.) treated with potassium chlorate by liquid chromatography-electrospray ionization mass spectrometry. Talanta. 2011;85:897–905.CrossRefGoogle Scholar
  5. 5.
    Liu JF, Ding J, Yuan BF, Feng YQ. Magnetic solid phase extraction coupled with in situ derivatization for the highly sensitive determination of acidic phytohormones in rice leaves by UPLC-MS/MS. Analyst. 2014;139:5605–13.CrossRefGoogle Scholar
  6. 6.
    Lu Q, Chen L, Lu M, Chen G, Zhang L. Extraction and analysis of auxins in plants using dispersive liquid-liquid microextraction followed by high-performance liquid chromatography with fluorescence detection. J Agric Food Chem. 2010;58:2763–70.CrossRefGoogle Scholar
  7. 7.
    Brenner ML. Modern methods for plant growth substance analysis. Annu Rev Plant Physiol. 1981;32:511–38.CrossRefGoogle Scholar
  8. 8.
    Ridgway K, Lalljie SP, Smith RM. Sample preparation techniques for the determination of trace residues and contaminants in foods. J Chromatogr A. 2007;1153:36–53.CrossRefGoogle Scholar
  9. 9.
    Tobiszewski M, Mechlińska A, Zygmunt B, Namieśnik J. Green analytical chemistry in sample preparation for determination of trace organic pollutants. TrAC Trends Anal Chem. 2009;28:943–51.CrossRefGoogle Scholar
  10. 10.
    Cai Y, Yan Z, Yang M, Huang X, Min W, Wang L, et al. Polydopamine decorated 3D nickel foam for extraction of sixteen polycyclic aromatic hydrocarbons. J Chromatogr A. 2016;1478:2–9.CrossRefGoogle Scholar
  11. 11.
    Sun Y, Lv Z, Sun Z, Wu C, Ji Z, You J. Determination of thiophenols with a novel fluorescence labelling reagent: analysis of industrial wastewater samples with SPE extraction coupled with HPLC. Anal Bioanal Chem. 2016;408:3527–36.CrossRefGoogle Scholar
  12. 12.
    Lhotská I, Šatínský D, Havlíková L, Solich P. A fully automated and fast method using direct sample injection combined with fused-core column on-line SPE–HPLC for determination of ochratoxin A and citrinin in lager beers. Anal Bioanal Chem. 2016;408:3319–29.CrossRefGoogle Scholar
  13. 13.
    Speltini A, Maraschi F, Sturini M, Contini M, Profumo A. Dispersive multi-walled carbon nanotubes extraction of benzenesulfonamides, benzotriazoles, and benzothiazoles from environmental waters followed by microwave desorption and HPLC-HESI-MS/MS. Anal Bioanal Chem. 2017;409:6709–18.CrossRefGoogle Scholar
  14. 14.
    Cai BD, Yin J, Hao YH, Li YN, Yuan BF, Feng YQ. Profiling of phytohormones in rice under elevated cadmium concentration levels by magnetic solid-phase extraction coupled with liquid chromatography tandem mass spectrometry. J Chromatogr A. 2015;1406:78–86.CrossRefGoogle Scholar
  15. 15.
    Luo XT, Cai BD, Chen X, Feng YQ. Improved methodology for analysis of multiple phytohormones using sequential magnetic solid-phase extraction coupled with liquid chromatography-tandem mass spectrometry. Anal Chim Acta. 2017;983:112–20.CrossRefGoogle Scholar
  16. 16.
    Yan Z, Wu M, Hu B, Yao M, Zhang L, Lu Q, et al. Electrospun UiO-66/polyacrylonitrile nanofibers as efficient sorbent for pipette tip solid phase extraction of phytohormones in vegetable samples. J Chromatogr A. 2018;1542:19–27.CrossRefGoogle Scholar
  17. 17.
    Chen J, Cao S, Zhu M, Xi C, Zhang L, Li X, et al. Fabrication of a high selectivity magnetic solid phase extraction adsorbent based on beta-cyclodextrin and application for recognition of plant growth regulators. J Chromatogr A. 2018;1547:1–13.CrossRefGoogle Scholar
  18. 18.
    Yan H, Wang F, Han D, Yang G. Simultaneous determination of four plant hormones in bananas by molecularly imprinted solid-phase extraction coupled with high performance liquid chromatography. Analyst. 2012;137:2884–90.CrossRefGoogle Scholar
  19. 19.
    Ishizu K, Takahashi D, Takeda H. Novel synthesis and characterization of hyperbranched polymers. Polymer. 2000;41:6081–6.CrossRefGoogle Scholar
  20. 20.
    Lee S, Eom Y, Park J, Lee J, Kim SY. Micro-hydrogel particles consisting of hyperbranched polyamidoamine for the removal of heavy metal ions from water. Sci Rep. 2017;7:10012.CrossRefGoogle Scholar
  21. 21.
    Bendjelloul M, Elandaloussi EH, de Ménorval L-C, Bentouami A. Quaternized triethanolamine-sebacoyl moieties in highly branched polymer architecture as a host for the entrapment of acid dyes in aqueous solutions. J Water Reuse Desalin. 2017;7:53–65.CrossRefGoogle Scholar
  22. 22.
    Qiu Z-L, Kong X, Yuan J-J, Shen Y-J, Zhu B-K, Zhu L-P, et al. Cross-linked PVC/hyperbranched polyester composite hollow fiber membranes for dye removal. React Funct Polym. 2018;122:51–9.CrossRefGoogle Scholar
  23. 23.
    Huang Z, Wang D, Zhu Y, Zeng W, Hu Y. The influence of mesoporous silica modified with phosphorus and nitrogen-containing hyperbranched molecules on thermal stability, combustion behavior, and toxic volatiles of epoxy resin. Polym Adv Technol. 2018;29:372–83.CrossRefGoogle Scholar
  24. 24.
    Yue X, Jiang F, Zhang D, Lin H, Chen Y. Preparation of adsorbent based on cotton fiber for removal of dyes. Fibers Polym. 2017;18:2102–10.CrossRefGoogle Scholar
  25. 25.
    Lin H, Han S, Dong Y, He Y. The surface characteristics of hyperbranched polyamide modified corncob and its adsorption property for Cr(VI). Appl Surf Sci. 2017;412:152–9.CrossRefGoogle Scholar
  26. 26.
    Zhang C, Li G, Zhang Z. A hydrazone covalent organic polymer based micro-solid phase extraction for online analysis of trace Sudan dyes in food samples. J Chromatogr A. 2015;1419:1–9.CrossRefGoogle Scholar
  27. 27.
    Liu X, Li H, Xu Z, Peng J, Zhu S, Zhang H. Development of hyperbranched polymers with non-covalent interactions for extraction and determination of aflatoxins in cereal samples. Anal Chim Acta. 2013;797:40–9.CrossRefGoogle Scholar
  28. 28.
    Wei W, Lu R, Xie H, Zhang Y, Bai X, Gu L, et al. Selective adsorption and separation of dyes from an aqueous solution on organic–inorganic hybrid cyclomatrix polyphosphazene submicro-spheres. J Mater Chem A. 2015;3:4314–22.CrossRefGoogle Scholar
  29. 29.
    He G, Peng H, Liu T, Yang M, Zhang Y, Fang Y. A novel picric acid film sensor via combination of the surface enrichment effect of chitosan films and the aggregation-induced emission effect of siloles. J Mater Chem. 2009;19:7347–53.CrossRefGoogle Scholar
  30. 30.
    Anasthas HM, Gaikar VG. Adsorption of acetic acid on ion-exchange resins in non-aqueous conditions. React Funct Polym. 2001;47:23–35.CrossRefGoogle Scholar
  31. 31.
    Zhang Y, Li Y, Hu Y, Li G, Chen Y. Preparation of magnetic indole-3-acetic acid imprinted polymer beads with 4-vinylpyridine and beta-cyclodextrin as binary monomer via microwave heating initiated polymerization and their application to trace analysis of auxins in plant tissues. J Chromatogr A. 2010;1217:7337–44.CrossRefGoogle Scholar
  32. 32.
    Wang M, Chang X, Wu X, Yan H, Qiao F. Water-compatible dummy molecularly imprinted resin prepared in aqueous solution for green miniaturized solid-phase extraction of plant growth regulators. J Chromatogr A. 2016;1458:9–17.CrossRefGoogle Scholar
  33. 33.
    Wang Z-H, Xia J-F, Han Q, Shi H-N, Guo X-M, Wang H, et al. Multi-walled carbon nanotube as a solid phase extraction adsorbent for analysis of indole-3-butyric acid and 1-naphthylacetic acid in plant samples. Chin Chem Lett. 2013;24:588–92.CrossRefGoogle Scholar
  34. 34.
    Fan S, Wang X, Li P, Zhang Q, Zhang W. Simultaneous determination of 13 phytohormones in oilseed rape tissues by liquid chromatography-electrospray tandem mass spectrometry and the evaluation of the matrix effect. J Sep Sci. 2011;34:640–50.CrossRefGoogle Scholar
  35. 35.
    Liu L, Xia L, Wu C, Qu F, Li G, Sun Z, et al. Zirconium (IV)-based metal organic framework (UIO-67) as efficient sorbent in dispersive solid phase extraction of plant growth regulator from fruits coupled with HPLC fluorescence detection. Talanta. 2016;154:23–30.CrossRefGoogle Scholar
  36. 36.
    You L, He M, Chen B, Hu B. One-pot synthesis of zeolitic imidazolate framework-8/poly (methyl methacrylate-ethyleneglycol dimethacrylate) monolith coating for stir bar sorptive extraction of phytohormones from fruit samples followed by high performance liquid chromatography-ultraviolet detection. J Chromatogr A. 2017;1524:57–65.CrossRefGoogle Scholar
  37. 37.
    Liu H-T, Li Y-F, Luan T-G, Lan C-Y, Shu W-S. Simultaneous determination of phytohormones in plant extracts using SPME and HPLC. Chromatographia. 2007;66:515–20.CrossRefGoogle Scholar
  38. 38.
    Wang W, He M, Chen B, Hu B. Simultaneous determination of acidic phytohormones in cucumbers and green bean sprouts by ion-pair stir bar sorptive extraction-high performance liquid chromatography. Talanta. 2017;170:128–36.CrossRefGoogle Scholar
  39. 39.
    Cui K, Lin Y, Zhou X, Li S, Liu H, Zeng F, et al. Comparison of sample pretreatment methods for the determination of multiple phytohormones in plant samples by liquid chromatography–electrospray ionization-tandem mass spectrometry. Microchem J. 2015;121:25–31.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Rui Zhang
    • 1
  • Shanshan Li
    • 1
  • Xiaoyan Liu
    • 1
    Email author
  • Haixia Zhang
    • 1
  1. 1.State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province and College of Chemistry and Chemical EngineeringLanzhou UniversityLanzhouChina

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