Skip to main content
SpringerLink
Log in

Determination of Sulfonamide Residues in Honey and Milk by HPLC Coupled with Novel Graphene Oxide/Polypyrrole Foam Material-Pipette Tip Solid Phase Extraction

  • Published:
Food Analytical Methods Aims and scope Submit manuscript

Abstract

A rapid, sensitive, and economical pipette tip solid phase extraction (PT-SPE) based on graphene oxide/polypyrrole (GO/PPy) coupled with high performance liquid chromatography (HPLC) was developed for the extraction and determination of sulfonamides (SAs) in honey and milk samples. The PT-SPE procedure involved only 3.0 mg of adsorbent, 3 min adsorptive extraction time, and less than 1.0 mL of solvent consumption (sample, washing, or eluent). Under the optimal conditions, good linearities (0.01–10.00 μg mL−1) were obtained with correlation coefficients (r) > 0.9996. The limits of detection (S/N = 3) were in the range of 1.04–1.50 ng mL−1. Meanwhile, the proposed method was successfully applied for the analysis of SAs in honey and milk with average recoveries within 62.3–109.0% and relative standard deviations less than 11.2%. The results demonstrated that the developed PT-SPE-HPLC method was suitable for the analysis of SAs in complex matrix due to its high sensitivity and accuracy.

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

Similar content being viewed by others

References

  • Abdallah H, Arnaudguilhem C, Jaber F, Lobinski R (2014) Multiresidue analysis of 22 sulfonamides and their metabolites in animal tissues using quick, easy, cheap, effective, rugged, and safe extraction and high resolution mass spectrometry (hybrid linear ion trap-Orbitrap). J Chromatogr A 1355:61–72

    Article  CAS  PubMed  Google Scholar 

  • Chullasat K, Nurerk P, Kanatharana P, Kueseng P, Sukchuay T, Bunkoed O (2017) Hybrid monolith sorbent of polypyrrole-coated graphene oxide incorporated into a polyvinyl alcohol cryogel for extraction and enrichment of sulfonamides from water samples. Anal Chim Acta 961:59–66

    Article  CAS  PubMed  Google Scholar 

  • Commission Regulation (European Union, EU), No 37/2010: 2009, On pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin

  • Council Directive (2002) 2001/110/EC of 20 December relating to honey. Off J Eur Commun L10:47–52

    Google Scholar 

  • Dasenaki ME, Thomaidis NS (2010) Multi-residue determination of seventeen sulfonamides and five tetracyclines in fish tissue using a multi-stage LC–ESI–MS/MS approach based on advanced mass spectrometric techniques. Anal Chim Acta 672:93–102

    Article  CAS  PubMed  Google Scholar 

  • de Oliveira HL, da Silva Anacleto S, da Silva ATM, Pereira AC, de Souza Borges W, Figueiredo EC, Borges KB (2016) Molecularly imprinted pipette-tip solid phase extraction for selective determination of fluoroquinolones in human urine using HPLC-DAD. J Chromatogr B 1033:427–439

  • Dmitrienko SG, Kochuk EV, Tolmacheva VV, Apyari VV, Zolotov YA (2015) Determination of the total content of some sulfonamides in milk using solid-phase extraction coupled with off-line derivatization and spectrophotometric detection. Food Chem 188:51–56

    Article  CAS  PubMed  Google Scholar 

  • Gao Q, Luo D, Bai M, Chen Z-W, Feng Y-Q (2011) Rapid determination of estrogens in milk samples based on magnetite nanoparticles/polypyrrole magnetic solid-phase extraction coupled with liquid chromatography–tandem mass spectrometry. J Agr Food Chem 59:8543–8549

    Article  CAS  Google Scholar 

  • Gu Z, Li C, Wang G, Zhang L, Li X, Wang W, Jin S (2010) Synthesis and characterization of polypyrrole/graphite oxide composite by in situ emulsion polymerization. J Polym Sci Pol Phys 48:1329–1335

    Article  CAS  Google Scholar 

  • Guillén I, Guardiola L, Almela L, Núñez-Delicado E, Gabaldón JA (2017) Simultaneous determination of nine sulphonamides by LC-MS for routine control of raw honey samples. Food Anal Method 10:1430–1441

    Article  Google Scholar 

  • Hoff RB, Pizzolato TM, Peralba MCR, Díaz-Cruz MS, Barceló D (2015) Determination of sulfonamide antibiotics and metabolites in liver, muscle and kidney samples by pressurized liquid extraction or ultrasound-assisted extraction followed by liquid chromatography–quadrupole linear ion trap-tandem mass spectrometry (HPLC–QqLIT-MS/MS). Talanta 134:768–778

    Article  CAS  PubMed  Google Scholar 

  • Hou X-L, Wu Y-L, Yang T, Du X-D (2013) Multi-walled carbon nanotubes–dispersive solid-phase extraction combined with liquid chromatography–tandem mass spectrometry for the analysis of 18 sulfonamides in pork. J Chromatogr B 929:107–115

    Article  CAS  Google Scholar 

  • Huertas-Pérez JF, Arroyo-Manzanares N, Havlíková L, Gámiz-Gracia L, Solich P, García-Campaña AM (2016) Method optimization and validation for the determination of eight sulfonamides in chicken muscle and eggs by modified QuEChERS and liquid chromatography with fluorescence detection. J Pharmaceut Biomed 124:261–266

    Article  CAS  Google Scholar 

  • Ibarra IS, Miranda JM, Rodriguez JA, Nebot C, Cepeda A (2014) Magnetic solid phase extraction followed by high-performance liquid chromatography for the determination of sulphonamides in milk samples. Food Chem 157:511–517

    Article  CAS  PubMed  Google Scholar 

  • Ji L, Chen W, Zheng S, Xu Z, Zhu D (2009) Adsorption of sulfonamide antibiotics to multiwalled carbon nanotubes. Langmuir 25:11608–11613

    Article  CAS  PubMed  Google Scholar 

  • Karageorgou E, Manousi N, Samanidou V, Kabir A, Furton KG (2016) Fabric phase sorptive extraction for the fast isolation of sulfonamides residues from raw milk followed by high performance liquid chromatography with ultraviolet detection. Food Chem 196:428–436

    Article  CAS  PubMed  Google Scholar 

  • Kazemi E, Dadfarnia S, Haji Shabani AM, Abbasi A, Rashidian Vaziri MR, Behjat A (2016) Iron oxide functionalized graphene oxide as an efficient sorbent for dispersive micro-solid phase extraction of sulfadiazine followed by spectrophotometric and mode-mismatched thermal lens spectrometric determination. Talanta 147:561–568

    Article  CAS  PubMed  Google Scholar 

  • Li S, Lu X, Xue Y, Lei J, Zheng T, Wang C (2012) Fabrication of polypyrrole/graphene oxide composite nanosheets and their applications for Cr(VI) removal in aqueous solution. PLoS One 7:e43328

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Li Y, Wu X, Li Z, Zhong S, Wang W, Wang A, Chen J (2015) Fabrication of CoFe2O4–graphene nanocomposite and its application in the magnetic solid phase extraction of sulfonamides from milk samples. Talanta 144:1279–1286

    Article  CAS  PubMed  Google Scholar 

  • Li Y, Li Z, Wang W, Zhong S, Chen J, Wang A-J (2016) Miniaturization of self-assembled solid phase extraction based on graphene oxide/chitosan coupled with liquid chromatography for the determination of sulfonamide residues in egg and honey. J Chromatogr A 1447:17–25

    Article  CAS  PubMed  Google Scholar 

  • Louppis AP, Kontominas MG, Papastephanou C (2017) Determination of antibiotic residues in honey by high-performance liquid chromatography with electronspray ionization tandem mass spectrometry. Food Anal Method 10:3385–3397

    Article  Google Scholar 

  • Luo Y-B, Chen X-J, Zhang H-F, Jiang X-Y, Li X, Li X-Y, Zhu F-P, Pang Y-Q, Hou H-W (2016) Simultaneous determination of polycyclic aromatic hydrocarbons and tobacco-specific N-nitrosamines in mainstream cigarette smoke using in-pipette-tip solid-phase extraction and on-line gel permeation chromatography-gas chromatography–tandem mass spectrometry. J Chromatogr A 1460:16–23

    Article  CAS  PubMed  Google Scholar 

  • Marcano DC, Kosynkin DV, Berlin JM, Sinitskii A, Sun Z, Slesarev A, Alemany LB, Lu W, Tour JM (2010) Improved synthesis of graphene oxide. ACS Nano 4:4806–4814

    Article  CAS  PubMed  Google Scholar 

  • Mistri HN, Jangid AG, Pudage A, Shah A, Shrivastav PS (2010) Simultaneous determination of sulfamethoxazole and trimethoprim in microgram quantities from low plasma volume by liquid chromatography–tandem mass spectrometry. Microchem J 94:130–138

    Article  CAS  Google Scholar 

  • Rahimi Z, Shahbazi Y, Ahmadi F (2017) Polypyrrole as an efficient solid-phase extraction sorbent for determination of chloramphenicol residue in chicken liver, kidney, and meat. Food Anal Method 10:955–963

    Article  Google Scholar 

  • Rao CNR, Sood AK, Subrahmanyam KS, Govindaraj A (2009) Graphene: the new two-dimensional nanomaterial. Angew Chem Int Edit 48:7752–7777

    Article  CAS  Google Scholar 

  • Shan L, Chen X, Tian X, Chen J, Zhou Z, Jiang M, Xu X, Hui D (2015) Fabrication of polypyrrole/nano-exfoliated graphite composites by in situ intercalation polymerization and their microwave absorption properties. Compos Part B-Eng 73:181–187

    Article  CAS  Google Scholar 

  • Shi Z, Hu J, Li Q, Zhang S, Liang Y, Zhang H (2014) Graphene based solid phase extraction combined with ultra high performance liquid chromatography–tandem mass spectrometry for carbamate pesticides analysis in environmental water samples. J Chromatogr A 1355:219–227

    Article  CAS  PubMed  Google Scholar 

  • Sun N, Han Y, Yan H, Song Y (2014) A self-assembly pipette tip graphene solid-phase extraction coupled with liquid chromatography for the determination of three sulfonamides in environmental water. Anal Chim Acta 810:25–31

    Article  CAS  PubMed  Google Scholar 

  • Tahmasebi E, Yamini Y, Seidi S, Rezazadeh M (2013) Extraction of three nitrophenols using polypyrrole-coated magnetic nanoparticles based on anion exchange process. J Chromatogr A 1314:15–23

    Article  CAS  PubMed  Google Scholar 

  • Van Eeckhaut A, Lanckmans K, Sarre S, Smolders I, Michotte Y (2009) Validation of bioanalytical LC–MS/MS assays: evaluation of matrix effects. J Chromatogr B 877:2198–2207

    Article  CAS  Google Scholar 

  • Wang C, Feng C, Gao Y, Ma X, Wu Q, Wang Z (2011) Preparation of a graphene-based magnetic nanocomposite for the removal of an organic dye from aqueous solution. Chem Eng J 173:92–97

    Article  CAS  Google Scholar 

  • Wang J, Tsuzuki T, Tang B, Hou X, Sun L, Wang X (2012) Reduced graphene oxide/ZnO composite: reusable adsorbent for pollutant management. ACS Appl Mater Inter 4:3084–3090

    Article  CAS  Google Scholar 

  • Wang L, Wang M, Yan H, Yuan Y, Tian J (2014) A new graphene oxide/polypyrrole foam material with pipette-tip solid-phase extraction for determination of three auxins in papaya juice. J Chromatogr A 1368:37–43

    Article  CAS  PubMed  Google Scholar 

  • Wang Z, He M, Jiang C, Zhang F, Du S, Feng W, Zhang H (2015) Matrix solid-phase dispersion coupled with homogeneous ionic liquid microextraction for the determination of sulfonamides in animal tissues using high-performance liquid chromatography. J Sep Sci 38:4127–4135

    Article  CAS  PubMed  Google Scholar 

  • Wang N, Xin H, Zhang Q, Jiang Y, Wang X, Shou D, Qin L (2017) Carbon nanotube-polymer composite for effervescent pipette tip solid phase microextraction of alkaloids and flavonoids from Epimedii herba in biological samples. Talanta 162:10–18

    Article  CAS  PubMed  Google Scholar 

  • Yan H, Sun N, Liu S, Row KH, Song Y (2014a) Miniaturized graphene-based pipette tip extraction coupled with liquid chromatography for the determination of sulfonamide residues in bovine milk. Food Chem 158:239–244

    Article  CAS  PubMed  Google Scholar 

  • Yan H, Yang C, Sun Y, Row KH (2014b) Ionic liquid molecularly imprinted polymers for application in pipette-tip solid-phase extraction coupled with gas chromatography for rapid screening of dicofol in celery. J Chromatogr A 1361:53–59

    Article  CAS  PubMed  Google Scholar 

  • Yao W, Ni T, Chen S, Li H, Lu Y (2014) Graphene/Fe3O4@polypyrrole nanocomposites as a synergistic adsorbent for Cr(VI) ion removal. Compos Sci Technol 99:15–22

    Article  CAS  Google Scholar 

  • Zhang C, Zhang Z, Li G (2014a) Preparation of sulfonated graphene/polypyrrole solid-phase microextraction coating by in situ electrochemical polymerization for analysis of trace terpenes. J Chromatogr A 1346:8–15

    Article  CAS  PubMed  Google Scholar 

  • Zhang YD, Zheng N, Han RW, Zheng BQ, Yu ZN, Li SL, Zheng SS, Wang JQ (2014b) Occurrence of tetracyclines, sulfonamides, sulfamethazine and quinolones in pasteurized milk and UHT milk in China's market. Food Control 36:238–242

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This project was financially supported by the National Natural Science Foundation of China (Nos. 21305128, 21275130 and 21275131) and a project of Natural Science Foundation of Zhejiang Province of China (No. LY17B050002).

Author information

Authors and Affiliations

  1. College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua, 321004, China

    Mengyu Qi, Chunyan Tu, Zhaoqian Li & Weiping Wang

  2. College of Geography and Environmental Sciences, Zhejiang Normal University, Jinhua, 321004, China

    Jianrong Chen & Ai-Jun Wang

Authors
  1. Mengyu Qi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chunyan Tu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhaoqian Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Weiping Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jianrong Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ai-Jun Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Weiping Wang.

Ethics declarations

Conflict of Interest

Mengyu Qi declares that she has no conflict of interest. Chunyan Tu declares that she has no conflict of interest. Zhaoqian Li declares that she has no conflict of interest. Weiping Wang declares that she has no conflict of interest. Jianrong Chen declares that he has no conflict of interest. Ai-Jun Wang declares that he has no conflict of interest.

Ethical Approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Informed Consent

Informed consent is not applicable for the nature of this study.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Qi, M., Tu, C., Li, Z. et al. Determination of Sulfonamide Residues in Honey and Milk by HPLC Coupled with Novel Graphene Oxide/Polypyrrole Foam Material-Pipette Tip Solid Phase Extraction. Food Anal. Methods 11, 2885–2896 (2018). https://doi.org/10.1007/s12161-018-1271-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12161-018-1271-5

Keywords

Search

Navigation