Skip to main content
SpringerLink
Log in

Selective extraction of 3,4-dihydroxybenzoic acid in Ilex chinensis Sims by meticulous mini-solid-phase microextraction using ternary deep eutectic solvent-based molecularly imprinted polymers

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

A ternary deep eutectic solvent (TDES) was used as both template and functional monomer in the synthesis of TDES-based molecularly imprinted polymers (TDES-MIPs). A meticulous miniaturized solid-phase microextraction (mini-SPME) method followed by high-performance liquid chromatography (HPLC) were used for the optimal speciation of 3,4-dihydroxybenzoic acid (3,4-DHBA) in the needle of a syringe system with response surface methodology (RSM). Under the optimal conditions for the determination of 3,4-DHBA (amount of adsorbent (2 mg), sample volume (1 mL), cycles for adsorption and desorption (6)), the actual extraction amount was 8.46 μg g−1. The limits of detection (LODs, S/N = 3) for 3,4-DHBA in Ilex chinensis Sims were 0.26–0.31 μg mL−1, and the intra-day and inter-day precision (relative standard deviations, n = 4) after spiking with 5 μg mL−1, 100 μg mL−1, and 200 μg mL−1 were both less than 4.21%. The meticulous method (TDES-MIP-mini-SPME) combined with RSM offers a significant advance over existing methods, because of the meticulous operation and excellent selectivity of 3,4-DHBA from complex samples.

ᅟ

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
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Xia WQ, Li RF, Liu JB, Cui BS, Hou Q, Sun H, et al. Triterpenoids from the leaves of Ilex chinensis. Phytochemistry. 2018;148:113–21.

    Article  CAS  Google Scholar 

  2. Zhang AL, Ye Q, Li BG, Qi HY, Zhnag GL. Phenolic and triterpene glycosides from the stems of Ilex litseaefolia. J Nat Prod. 2005;68(1):1531–5.

    Article  CAS  Google Scholar 

  3. Li LJ, Zhang Y, Zhang P, Pi HF, Ruan HL, Wu JZ. Flavans from the leaf of Ilex centrochinensis. J Asian Nat Prod Res. 2011;13(04):367–72.

    Article  CAS  Google Scholar 

  4. Son JH, Kim SY, Jang HH, Lee SN, Ahn KJ. Protective effect of protocatechuic acid against inflammatory stress induced in human dermal fibroblasts. Biomed Dermatol. 2018;2(1):9–14.

    Article  Google Scholar 

  5. Musa M, Ibrahim WAW, Marsin FM, Keyon ASA, Nodeh HR. Graphene-magnetite as adsorbent for magnetic solid phase extraction of 4-hydroxybenzoic acid and 3,4-dihydroxybenzoic acid in stingless bee honey. Food Chem. 2018;265:165–72.

    Article  CAS  Google Scholar 

  6. Mateos R, Espartero JL, Trujillo M, Ríos JJ, León-Camacho M, Alcudia F, et al. Determination of phenols, flavones, and lignans in virgin olive oils by solid-phase extraction and high-performance liquid chromatography with diode array ultraviolet detection. J Agric Food Chem. 2001;49(5):2185–92.

    Article  CAS  Google Scholar 

  7. Shalash M, Makahleh A, Salhimi SM, Saad B. Vortex-assisted liquid-liquid-liquid microextraction followed by high performance liquid chromatography for the simultaneous determination of fourteen phenolic acids in honey, iced tea and canned coffee drinks. Talanta. 2017;174:428–35.

    Article  CAS  Google Scholar 

  8. Hou X, Lu X, Tang S, Wang L, Guo Y. Graphene oxide reinforced ionic liquid-functionalized adsorbent for solid-phase extraction of phenolic acids. J Chromatogr B. 2018;1072:123–9.

    Article  CAS  Google Scholar 

  9. Tafazoli Z, Azar PA, Tehrani MS, Husain SW. Facile preparation of multifunctional carbon nanotube/magnetite/polyaniline nanocomposite offering a strong option for efficient solid-phase microextraction coupled with GC-MS for the analysis of phenolic compounds. J Sep Sci. 2018;41(13):2736–42.

    Article  CAS  Google Scholar 

  10. De GS, Gionfriddo E, Pawliszyn J. A new and efficient solid phase microextraction approach for analysis of high fat content food samples using a matrix-compatible coating. Talanta. 2017;167:754–60.

    Article  Google Scholar 

  11. Trabalón L, Nadal M, Borrull F, Pocurull E. Determination of benzothiazoles in seafood species by subcritical water extraction followed by solid-phase microextraction-gas chromatography-tandem mass spectrometry: estimating the dietary intake. Anal Bioanal Chem. 2017;409(23):5513–22.

    Article  Google Scholar 

  12. Chen L, Huang X. Preparation and application of a poly (ionic liquid)-based molecularly imprinted polymer for multiple monolithic fiber solid-phase microextraction of phenolic acids in fruit juice and beer samples. Analyst. 2017;142(21):4039–47.

    Article  CAS  Google Scholar 

  13. Liu YC, Liu YJ, Liu ZM, Hu XZ, Xu ZG. β-Cyclodextrin molecularly imprinted solid-phase microextraction coatings for selective recognition of polychlorophenols in water samples. Anal Bioanal Chem. 2018;410(2):509–19.

    Article  CAS  Google Scholar 

  14. Li G, Row KH. Recent applications of molecularly imprinted polymers (MIPs) on micro-extraction techniques. Sep Purif Rev. 2018;47(1):1–18.

    Article  CAS  Google Scholar 

  15. Shishov A, Bulatov A, Locatelli M, Carradori S, Andruch V. Application of deep eutectic solvents in analytical chemistry: a review. Microchem J. 2017;135:33–8.

    Article  CAS  Google Scholar 

  16. Panhwar AH, Tuzen M, Kazi TG. Deep eutectic solvent based advance microextraction method for determination of aluminum in water and food samples: multivariate study. Talanta. 2018;178:588–93.

    Article  CAS  Google Scholar 

  17. Sutton AT, Fraige K, Leme GM, Bolzani VS, Hilder EF, Cavalheiro AJ. Natural deep eutectic solvents as the major mobile phase components in high-performance liquid chromatography—searching for alternatives to organic solvents. Anal Bioanal Chem. 2018;410(16):3705–13.

    Article  CAS  Google Scholar 

  18. Alhassan Y, Pali HS, Kumar N, Bugaje IM. Co-liquefaction of whole Jatropha curcas seed and glycerol using deep eutectic solvents as catalysts. Energy. 2017;138:48–59.

    Article  CAS  Google Scholar 

  19. Liang S, Yan H, Cao J, Han Y, Shen S, Bai L. Molecularly imprinted phloroglucinol-formaldehyde-melamine resin prepared in a deep eutectic solvent for selective recognition of clorprenaline and bambuterol in urine. Anal Chim Acta. 2017;95:68–77.

    Article  Google Scholar 

  20. Fu N, Li L, Liu X, Fu N, Zhang C, Hu L, et al. Specific recognition of polyphenols by molecularly imprinted polymers based on a ternary deep eutectic solvent. J Chromatogr A. 2017;1530:23–34.

    Article  CAS  Google Scholar 

  21. Liu Y, Wang Y, Dai Q, Zhou Y. Magnetic deep eutectic solvents molecularly imprinted polymers for the selective recognition and separation of protein. Anal Chim Acta. 2016;936:168–78.

    Article  CAS  Google Scholar 

  22. Xu K, Wang Y, Wei X, Chen J, Xu P, Zhou Y. Preparation of magnetic molecularly imprinted polymers based on a deep eutectic solvent as the functional monomer for specific recognition of lysozyme. Microchim Acta. 2018;185(2):146–53.

    Article  Google Scholar 

  23. Díaz-de-Cerio E, Arráez-Román D, Segura-Carretero A, Ferranti P, Nicoletti R, Perrotta GM, et al. Establishment of pressurized-liquid extraction by response surface methodology approach coupled to HPLC-DAD-TOF-MS for the determination of phenolic compounds of myrtle leaves. Anal Bioanal Chem. 2018;410(15):3547–57.

    Article  Google Scholar 

  24. Li G, Zhu T, Lei Y. Choline chloride-based deep eutectic solvents as additives for optimizing chromatographic behavior of caffeic acid. Korean J Chem Eng. 2015;32(10):2103–8.

    Article  CAS  Google Scholar 

  25. Zeković Z, Vidović S, Vladić J, Radosavljević R, Cvejin A, Elgndi M, et al. Optimization of subcritical water extraction of antioxidants from Coriandrum sativum seeds by response surface methodology. J Supercrit Fluid. 2014;95:560–6.

    Article  Google Scholar 

  26. Aybastıer Ö, Işık E, Şahin S, Demir C. Optimization of ultrasonic-assisted extraction of antioxidant compounds from blackberry leaves using response surface methodology. Ind Crop Prod. 2013;44:558–65.

    Article  Google Scholar 

  27. Dmitrienko SG, Irkha VV, Duisebaeva TB, Mikhailik YV, Zolotov YA. Synthesis and study of the sorption properties of 4-hydroxybenzoic acid-imprinted polymers. J Anal Chem. 2006;61(1):14–9.

    Article  CAS  Google Scholar 

  28. You QP, Peng MJ, Zhang YP, Guo JF, Shi SY. Preparation of magnetic dummy molecularly imprinted polymers for selective extraction and analysis of salicylic acid in Actinidia chinensis. Anal Bioanal Chem. 2014;406(3):831–9.

    Article  CAS  Google Scholar 

  29. Klejdus B, Plaza M, Šnóblová M, LeaLojková L. Development of new efficient method for isolation of phenolics from sea algae prior to their rapid resolution liquid chromatographic–tandem mass spectrometric determination. J Pharmaceut Biomed. 2017;135:87–96.

    Article  CAS  Google Scholar 

  30. Du Y, Wang Z, Wang L, Gao M, Wang L, Gan C, et al. Simultaneous determination of seven phenolic acids in rat plasma using UHPLC-ESI-MS/MS after oral administration of Echinacea purpurea extract. Molecules. 2017;22(9):1494–509.

    Article  Google Scholar 

  31. Mattonai M, Parri E, Querci D, Degano L, Ribechini E. Development and validation of an HPLC-DAD and HPLC/ESI-MS2 method for the determination of polyphenols in monofloral honeys from Tuscany (Italy). Microchem J. 2016;126:220–9.

    Article  CAS  Google Scholar 

Download references

Funding

This study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2015R1A4A1042434).

Author information

Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Inha University, Incheon, 402751, South Korea

    Guizhen Li & Kyung Ho Row

Authors
  1. Guizhen Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kyung Ho Row
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kyung Ho Row.

Ethics declarations

Conflict of interest

The authors declare that they have no competing interests.

Electronic supplementary material

ESM 1

(PDF 967 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, G., Row, K.H. Selective extraction of 3,4-dihydroxybenzoic acid in Ilex chinensis Sims by meticulous mini-solid-phase microextraction using ternary deep eutectic solvent-based molecularly imprinted polymers. Anal Bioanal Chem 410, 7849–7858 (2018). https://doi.org/10.1007/s00216-018-1406-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-018-1406-y

Keywords

Search

Navigation