Graphene Oxide-Ionic Liquid Used As Solid-Phase Microextraction Coating For Polyphenolic Compounds' Extraction And Determination With GC-MS After On-Fiber Derivatization In Wine

Abstract

We describe the use of a home-made fiber coated by graphene oxide modified by an ionic liquid having methylimidazolium cation with an amino-functional group for the extraction of polyphenolic compounds (P.C.s). We then performed the determination by gas chromatography coupled with mass spectrometry after on-fiber derivatization. The authors optimized the main parameters influencing the extraction and derivatization processes. The on-fiber derivatization was employed within 15 min at 60 ºC using 20 µL of trimethylsilyl reagents. Under the optimized conditions, the calibration curves for 12 P.C.s were linear from 0.1 to 1000 µg/L, and the detection limits were between 0.02 and 0.1 µg/L. We determined the single fiber repeatability obtained for all calibration points and the fiber to fiber reproducibility for 100 µg/L to be < 14.82% and < 5.87%, respectively. The extraction efficacy of the home-made fiber due to high intermolecular and electrostatic attractions was much better than the commercial fibers. We successfully applied the method to the analysis of P.C.s in wine samples with the recoveries from 72.8 to 99.9%.

Keywords

• GO APMIM NTf2 coated fiber,SPME-GC-MS,polyphenolic compounds,derivatization on-fiber,wine sample

References

1. 1. Pourcel L, Routaboul J, Cheynier V, Lepiniec L, Debeaujon I. Flavonoid oxidation in plants: from biochemical properties to physiological functions. Trends in Plant Science. 2007 Jan;12(1):29–36.
2. 2. Lesschaeve I, Noble AC. Polyphenols: factors influencing their sensory properties and their effects on food and beverage preferences. The American Journal of Clinical Nutrition. 2005 Jan 1;81(1):330S-335S.
3. 3. Cardona F, Andrés-Lacueva C, Tulipani S, Tinahones FJ, Queipo-Ortuño MI. Benefits of polyphenols on gut microbiota and implications in human health. The Journal of Nutritional Biochemistry. 2013 Aug;24(8):1415–22.
4. 4. Klatsky AL. Wine, Liquor, Beer, and Mortality. American Journal of Epidemiology. 2003 Sep 15;158(6):585–95.
5. 5. Nave F, Cabrita MJ, da Costa CT. Use of solid-supported liquid–liquid extraction in the analysis of polyphenols in wine. Journal of Chromatography A. 2007 Oct;1169(1–2):23–30.
6. 6. Denderz N, Lehotay J. Using of molecularly imprinted polymers for determination of gallic and protocatechuic acids in red wines by high performance liquid chromatography. Journal of Chromatography A. 2014 Dec;1372:72–80.
7. 7. Cacho JI, Campillo N, Viñas P, Hernández-Córdoba M. Stir bar sorptive extraction with gas chromatography–mass spectrometry for the determination of resveratrol, piceatannol and oxyresveratrol isomers in wines. Journal of Chromatography A. 2013 Nov;1315:21–7.
8. 8. Aresta A, Cotugno P, Massari F, Zambonin C. Determination of Trans-resveratrol in Wines, Spirits, and Grape Juices Using Solid-Phase Micro Extraction Coupled to Liquid Chromatography with UV Diode-Array Detection. Food Anal Methods. 2018 Feb;11(2):426–31.

9. 9. Arthur CL, Pawliszyn Janusz. Solid phase microextraction with thermal desorption using fused silica optical fibers. Anal Chem. 1990 Oct;62(19):2145–8.
10. 10. Souza-Silva ÉA, Jiang R, Rodríguez-Lafuente A, Gionfriddo E, Pawliszyn J. A critical review of the state of the art of solid-phase microextraction of complex matrices I. Environmental analysis. TrAC Trends in Analytical Chemistry. 2015 Sep;71:224–35.
11. 11. Dreyer DR, Park S, Bielawski CW, Ruoff RS. The chemistry of graphene oxide. Chem Soc Rev. 2010;39(1):228–40.
12. 12. Ye N, Shi P. Applications of Graphene-Based Materials in Solid-Phase Extraction and Solid-Phase Microextraction. Separation & Purification Reviews. 2015 Jul 3;44(3):183–98.
13. 13. Dahaghin Z, Mousavi HZ, Sajjadi SM. Synthesis and Application of Magnetic Graphene Oxide Modified with 8-Hydroxyquinoline for Extraction and Preconcentration of Trace Heavy Metal Ions. ChemistrySelect. 2017 Jan 23;2(3):1282–9.
14. 14. Anderson JL, Armstrong DW, Wei G-T. Ionic Liquids in Analytical Chemistry. Anal Chem. 2006 May;78(9):2892–902.
15. 15. Berthod A, Ruiz-Ángel MJ, Carda-Broch S. Recent advances on ionic liquid uses in separation techniques. Journal of Chromatography A. 2018 Jul;1559:2–16.
16. 16. Hou X, Guo Y, Liang X, Wang X, Wang L, Wang L, et al. Bis(trifluoromethanesulfonyl)imide-based ionic liquids grafted on graphene oxide-coated solid-phase microextraction fiber for extraction and enrichment of polycyclic aromatic hydrocarbons in potatoes and phthalate esters in food-wrap. Talanta. 2016 Jun;153:392–400.
17. 17. Li G, Ho Row K. Ionic liquid based on imidazolium cation to modify functional materials on separation of active compounds. Journal of Liquid Chromatography & Related Technologies. 2018 Oct 2;41(15–16):937–48.
18. 18. Tashakkori P, Erdem P, Merdivan M, Bozkurt SS. Determination of Phthalate Esters in Water and Coffee by Solid-Phase Microextraction Using Vinyl Terminated Imidazolium Based Ionic Liquid Grafted on Graphene Oxide Coatings. ChemistrySelect. 2019 Feb 28;4(8):2307–13.
19. 19. Tian Y, Gou X, Niu P, Sun L, Guo Y. Multivariate Data Analysis of the Physicochemical and Phenolic Properties of Not from Concentrate Apple Juices to Explore the Alternative Cultivars in Juice Production. Food Anal Methods. 2018 Jun;11(6):1735–47.
20. 20. Anli E, Vural N, Demiray S, Özkan M. Trans- resveratrol and Other Phenolic Compounds in Turkish Red Wines with HPLC. Journal of Wine Research. 2006 Aug;17(2):117–25.
21. 21. Viñas P, Campillo N, Hernández-Pérez M, Hernández-Córdoba M. A comparison of solid-phase microextraction and stir bar sorptive extraction coupled to liquid chromatography for the rapid analysis of resveratrol isomers in wines, musts and fruit juices. Analytica Chimica Acta. 2008 Mar;611(1):119–25.
22. 22. Mirnaghi FS, Mousavi F, Rocha SM, Pawliszyn J. Automated determination of phenolic compounds in wine, berry, and grape samples using 96-blade solid phase microextraction system coupled with liquid chromatography–tandem mass spectrometry. Journal of Chromatography A. 2013 Feb;1276:12–9.
23. 23. 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.
24. 24. Canini A, Alesiani D, D’Arcangelo G, Tagliatesta P. Gas chromatography–mass spectrometry analysis of phenolic compounds from Carica papaya L. leaf. Journal of Food Composition and Analysis. 2007 Nov;20(7):584–90.
25. 25. Bustamante L, Cárdenas D, von Baer D, Pastene E, Duran-Sandoval D, Vergara C, et al. Evaluation of microextraction by packed sorbent, liquid-liquid microextraction and derivatization pretreatment of diet-derived phenolic acids in plasma by gas chromatography with triple quadrupole mass spectrometry. J Sep Sci. 2017 Sep;40(17):3487–96.
26. 26. Montes R, García-López M, Rodríguez I, Cela R. Mixed-mode solid-phase extraction followed by acetylation and gas chromatography mass spectrometry for the reliable determination of trans-resveratrol in wine samples. Analytica Chimica Acta. 2010 Jul;673(1):47–53.
27. 27. Cacho JI, Campillo N, Viñas P, Hernández-Córdoba M. Stir bar sorptive extraction with gas chromatography–mass spectrometry for the determination of resveratrol, piceatannol and oxyresveratrol isomers in wines. Journal of Chromatography A. 2013 Nov;1315:21–7.
28. 28. Viñas P, Campillo N, Martínez-Castillo N, Hernández-Córdoba M. Solid-phase microextraction on-fiber derivatization for the analysis of some polyphenols in wine and grapes using gas chromatography–mass spectrometry. Journal of Chromatography A. 2009 Feb;1216(9):1279–84.
29. 29. Cai L, Koziel JA, Dharmadhikari M, (Hans) van Leeuwen J. Rapid determination of trans-resveratrol in red wine by solid-phase microextraction with on-fiber derivatization and multidimensional gas chromatography–mass spectrometry. Journal of Chromatography A. 2009 Jan;1216(2):281–7.
30. 30. Citová I, Sladkovský R, Solich P. Analysis of phenolic acids as chloroformate derivatives using solid phase microextraction–gas chromatography. Analytica Chimica Acta. 2006 Jul;573–574:231–41.
31. 31. Angioni A, Pintore GAM, Caboni P. Determination of Wine Aroma Compounds by Dehydration Followed by GC/MS. Journal of AOAC INTERNATIONAL. 2012 May 1;95(3):813–9.
32. 32. Erdem P, Tashakkori P, Merdivan M, Bozkurt SS. Ionic liquid-based graphene oxide-coated fiber for headspace-solid phase microextraction of polycyclic aromatic hydrocarbons in water samples. Turkish Journal of Chemistry. 2019;43:1383–97.
33. 33. Yang H, Shan C, Li F, Han D, Zhang Q, Niu L. Covalent functionalization of polydisperse chemically-converted graphene sheets with amine-terminated ionic liquid. Chem Commun. 2009;(26):3880.
34. 34. Yuan S, Liu Z, Lian H, Yang C, Lin Q, Yin H, et al. Simultaneous determination of eleven estrogenic and odorous chloro- and bromo-phenolic compounds in surface water through an automated online headspace SPME followed by on-fiber derivatization coupled with GC-MS. Anal Methods. 2017;9(33):4819–27.
35. 35. Proestos C, Sereli D, Komaitis M. Determination of phenolic compounds in aromatic plants by RP-HPLC and GC-MS. Food Chemistry. 2006 Mar;95(1):44–52.
36. 36. Xie L, Liu S, Han Z, Jiang R, Liu H, Zhu F, et al. Preparation and characterization of metal-organic framework MIL-101(Cr)-coated solid-phase microextraction fiber. Analytica Chimica Acta. 2015 Jan;853:303–10.