Characterization of the aroma profile of novel Brazilian wines by solid-phase microextraction using polymeric ionic liquid sorbent coatings

Abstract

In this study, a series of polymeric ionic liquid (PIL) sorbent coatings is evaluated for the extraction of polar volatile organic compounds (VOCs) from Brazilian wines using headspace solid-phase microextraction (HS-SPME), including samples from ‘Isabella’ and ‘BRS Magna’ cultivars—the latter was recently introduced by the Brazilian Agricultural Research Corporation – National Grape & Wine Research Center. The structurally tuned SPME coatings were compared to the commercial SPME phases, namely poly(acrylate) (PA) and divinylbenzene/carboxen/poly(dimethylsiloxane) (DVB/CAR/PDMS). The separation, detection and identification of the aroma profiles were obtained using comprehensive two-dimensional gas chromatography mass spectrometry (GC×GC-MS). The best performing PIL-based SPME fiber, namely 1-hexadecyl-3-vinylimidazolium bis[(trifluoromethyl)sulfonyl]imide with 1,12-di(3-vinylimidazolium)dodecane dibis[(trifluoromethyl)sulfonyl]imide incorporated cross-linker supported on an elastic nitinol wire, exhibited superior performance to DVB/CAR/PDMS regarding the average number of extracted peaks and extracted more polar analytes providing additional insight into the aroma profile of ‘BRS Magna’ wines. Four batches of wine were evaluated, namely ‘Isabella’ and ‘BRS Magna’ vintages 2015 and 2016, using highly selective PIL-based SPME coatings and enabled the detection of 350+ peaks. Furthermore, this is the first report evaluating the aroma of ‘BRS Magna’ wines. A hybrid approach that combined pixel-based Fisher ratio and peak table-based data comparison was used for data handling. This proof-of-concept experiment provided reliable and statistically valid distinction of wines that may guide regulation agencies to create high sample throughput protocols to screen wines exported by Brazilian vintners.

Highly selective extraction of wine aroma using polymeric ionic liquid.

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References

  1. 1.

    Flamini R, Traldi P. Mass spectrometry in grape and wine chemistry. 1st ed. Hoboken: Wiley; 2009.

    Google Scholar 

  2. 2.

    Arcari SG, Caliari V, Sganzerla M, Godoy HT. Volatile composition of Merlot red wine and its contribution to the aroma: optimization and validation of analytical method. Talanta. 2017;174:752–66.

    Article  CAS  PubMed  Google Scholar 

  3. 3.

    De Fátima Alpendurada M. Solid-phase microextraction: a promising technique for sample preparation in environmental analysis. J Chromatogr A. 2000;889:3–14.

    Article  Google Scholar 

  4. 4.

    Sajid M, Płotka-Wasylka J. Combined extraction and microextraction techniques: recent trends and future perspectives. TrAC - Trends Anal Chem. 2018;103:74–86.

    Article  CAS  Google Scholar 

  5. 5.

    Boyaci E, Rodríguez-Lafuente Á, Gorynski K, Mirnaghi F, Souza-Silva ÉA, Hein D, et al. Sample preparation with solid phase microextraction and exhaustive extraction approaches: comparison for challenging cases. Anal Chim Acta. 2015;873:14–30.

    Article  CAS  PubMed  Google Scholar 

  6. 6.

    de Grazia S, 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  CAS  PubMed  Google Scholar 

  7. 7.

    Reyes-Garcés N, Gionfriddo E, Gómez-Ríos GA, Alam MN, Boyaci E, Bojko B, et al. Advances in solid phase microextraction and perspective on future directions. Anal Chem. 2018;90:302–60.

    Article  CAS  PubMed  Google Scholar 

  8. 8.

    Cordero C, Kiefl J, Schieberle P, Reichenbach SE, Bicchi C. Comprehensive two-dimensional gas chromatography and food sensory properties: potential and challenges. Anal Bioanal Chem. 2015;407:169–91.

    Article  CAS  PubMed  Google Scholar 

  9. 9.

    Zhang C, Ingram IC, Hantao LW, Anderson JL. Identifying important structural features of ionic liquid stationary phases for the selective separation of nonpolar analytes by comprehensive two-dimensional gas chromatography. J Chromatogr A. 2015;1386:89–97.

    Article  CAS  PubMed  Google Scholar 

  10. 10.

    Zhao F, Meng Y, Anderson JL. Polymeric ionic liquids as selective coatings for the extraction of esters using solid-phase microextraction. J Chromatogr A. 2008;1208:1–9.

    Article  CAS  PubMed  Google Scholar 

  11. 11.

    Ho TD, Canestraro AJ, Anderson JL. Ionic liquids in solid-phase microextraction: a review. Anal Chim Acta. 2011;695:18–43.

    Article  CAS  PubMed  Google Scholar 

  12. 12.

    Toledo BR, Hantao LW, Ho TD, Augusto F, Anderson JL. A chemometric approach toward the detection and quantification of coffee adulteration by solid-phase microextraction using polymeric ionic liquid sorbent coatings. J Chromatogr A. 2014;1346:1–7.

    Article  CAS  PubMed  Google Scholar 

  13. 13.

    Cagliero C, Nan H, Bicchi C, Anderson JL. Matrix-compatible sorbent coatings based on structurally-tuned polymeric ionic liquids for the determination of acrylamide in brewed coffee and coffee powder using solid-phase microextraction. J Chromatogr A. 2016;1459:17–23.

    Article  CAS  PubMed  Google Scholar 

  14. 14.

    Yu H, Ho TD, Anderson JL. Ionic liquid and polymeric ionic liquid coatings in solid-phase microextraction. TrAC Trends Anal Chem. 2013;45:219–32.

    Article  CAS  Google Scholar 

  15. 15.

    Ho TD, Zhang C, Hantao LW, Anderson JL. Ionic liquids in analytical chemistry: fundamentals, advances, and perspectives. Anal Chem. 2014;86:262–85.

    Article  CAS  PubMed  Google Scholar 

  16. 16.

    Patinha DJS, Tomé LC, Isik M, Mecerreyes D, Silvestre AJD, Marrucho IM. Expanding the applicability of poly(ionic liquids) in solid phase microextraction: pyrrolidinium coatings. Materials. 2017;10:1094.

    Article  PubMed Central  Google Scholar 

  17. 17.

    Ho TD, Cole WTS, Augusto F, Anderson JL. Insight into the extraction mechanism of polymeric ionic liquid sorbent coatings in solid-phase microextraction. J Chromatogr A. 2013;1298:146–51.

    Article  CAS  PubMed  Google Scholar 

  18. 18.

    Ryan D, Shellie R, Tranchida P, Casilli A, Mondello L, Marriott P. Analysis of roasted coffee bean volatiles by using comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry. J Chromatogr A. 2004;1054:57–65.

    Article  CAS  PubMed  Google Scholar 

  19. 19.

    Adahchour M, Beens J, Vreuls R, Brinkman U. Recent developments in comprehensive two-dimensional gas chromatography (GC×GC)III. Applications for petrochemicals and organohalogens. TrAC Trends Anal Chem. 2006;25:726–41.

    Article  CAS  Google Scholar 

  20. 20.

    Seeley JV, Seeley SK. Multidimensional gas chromatography: fundamental advances and new applications. Anal Chem. 2013;85:557–78.

    Article  CAS  PubMed  Google Scholar 

  21. 21.

    Chin S-T, Marriott PJ. Multidimensional gas chromatography beyond simple volatiles separation. Chem Commun. 2014;50:8819.

    Article  CAS  Google Scholar 

  22. 22.

    Edwards M, Mostafa A, Gorecki T. Modulation in comprehensive two-dimensional gas chromatography: 20 years of innovation. Anal Bioanal Chem. 2011;401:2335–49.

    Article  CAS  PubMed  Google Scholar 

  23. 23.

    Tranchida PQ, Purcaro G, Dugo P, Mondello L, Purcaro G. Modulators for comprehensive two-dimensional gas chromatography. TrAC Trends Anal Chem. 2011;30:1437–61.

    Article  CAS  Google Scholar 

  24. 24.

    Nicolli KP, Biasoto ACT, Souza-Silva ÉA, Guerra CC, dos Santos HP, Welke JE, et al. Sensory, olfactometry and comprehensive two-dimensional gas chromatography analyses as appropriate tools to characterize the effects of vine management on wine aroma. Food Chem. 2018;243:103–17.

    Article  CAS  PubMed  Google Scholar 

  25. 25.

    Robinson AL, Boss PK, Heymann H, Solomon PS, Trengove RD. Development of a sensitive non-targeted method for characterizing the wine volatile profile using headspace solid-phase microextraction comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry. J Chromatogr A. 2011;1218:504–17.

    Article  CAS  PubMed  Google Scholar 

  26. 26.

    Welke JE, Manfroi V, Zanus M, Lazarotto M, Alcaraz ZC. Characterization of the volatile profile of Brazilian Merlot wines through comprehensive two dimensional gas chromatography time-of-flight mass spectrometric detection. J Chromatogr A. 2012;1226:124–39.

    Article  CAS  PubMed  Google Scholar 

  27. 27.

    Bordiga M, Rinaldi M, Locatelli M, Piana G, Travaglia F, Coïsson JD, et al. Characterization of Muscat wines aroma evolution using comprehensive gas chromatography followed by a post-analytic approach to 2D contour plots comparison. Food Chem. 2013;140:57–67.

    Article  CAS  PubMed  Google Scholar 

  28. 28.

    Dugo G, Franchina FA, Scandinaro MR, Bonaccorsi I, Cicero N, Tranchida PQ, et al. Elucidation of the volatile composition of Marsala wines by using comprehensive two-dimensional gas chromatography. Food Chem. 2014;142:262–8.

    Article  CAS  PubMed  Google Scholar 

  29. 29.

    Nicolli KP, Welke JE, Closs M, Caramão EB, Costa G, Manfroi V, et al. Characterization of the volatile profile of Brazilian moscatel sparkling wines through solid phase microextraction and gas chromatography. J Braz Chem Soc. 2015;26:1411–30.

    Google Scholar 

  30. 30.

    Carlin S, Vrhovsek U, Franceschi P, Lotti C, Bontempo L, Camin F, et al. Regional features of northern Italian sparkling wines, identified using solid-phase micro extraction and comprehensive two-dimensional gas chromatography coupled with time-of-flight mass spectrometry. Food Chem. 2016;208:68–80.

    Article  CAS  PubMed  Google Scholar 

  31. 31.

    Lago LO, Nicolli KP, Marques AB, Zini CA, Welke JE. Influence of ripeness and maceration of the grapes on levels of furan and carbonyl compounds in wine – simultaneous quantitative determination and assessment of the exposure risk to these compounds. Food Chem. 2017;230:594–603.

    Article  CAS  PubMed  Google Scholar 

  32. 32.

    Vestner J, Malherbe S, Du Toit M, Nieuwoudt HH, Mostafa A, Górecki T, et al. Investigation of the volatile composition of pinotage wines fermented with different malolactic starter cultures using comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry (GC×GC-TOF-MS). J Agric Food Chem. 2011;59:12732–44.

    Article  CAS  PubMed  Google Scholar 

  33. 33.

    Bordiga M, Piana G, Coïsson JD, Travaglia F, Arlorio M. Headspace solid-phase micro extraction coupled to comprehensive two-dimensional with time-of-flight mass spectrometry applied to the evaluation of Nebbiolo-based wine volatile aroma during ageing. Int J Food Sci Technol. 2014;49:787–96.

    Article  CAS  Google Scholar 

  34. 34.

    Welke JE, Manfroi V, Zanus M, Lazzarotto M, Zini CA. Differentiation of wines according to grape variety using multivariate analysis of comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometric detection data. Food Chem. 2013;141:3897–905.

    Article  CAS  PubMed  Google Scholar 

  35. 35.

    Ritschel P, Ritschel P, Dimas J, Maia G, Camargo UA, Zanus MC, et al. ‘BRS MAGNA’—a novel grape cultivar for juice making, with wide climatic adaptation. Crop Breed Appl Biotechnol. 2014;14:266–9.

    Article  Google Scholar 

  36. 36.

    Pierce KM, Parsons BA, Synovec RE. Pixel-level data analysis methods for comprehensive two-dimensional chromatography. Data Handl Sci Technol. 2015;29:427–63.

    Article  Google Scholar 

  37. 37.

    Parsons BA, Marney LC, Siegler WC, Hoggard JC, Wright BW, Synovec RE. Tile-based fisher ratio analysis of comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry (GC × GC–TOFMS) data using a null distribution approach. Anal Chem. 2015;87:3812–9.

    Article  CAS  PubMed  Google Scholar 

  38. 38.

    Pinkerton DK, Pierce KM, Synovec RE. Chemometric resolution of complex higher order chromatographic data with spectral detection. Data Handl Sci Technol. 2016;30:333–52.

    Article  Google Scholar 

  39. 39.

    Watson NE, Parsons BA, Synovec RE. Performance evaluation of tile-based Fisher ratio analysis using a benchmark yeast metabolome dataset. J Chromatogr A. 2016;1459:101–11.

    Article  CAS  PubMed  Google Scholar 

  40. 40.

    Reaser BC, Wright BW, Synovec RE. Using receiver operating characteristic curves to optimize discovery-based software with comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry. Anal Chem. 2017;89:3606–12.

    Article  CAS  PubMed  Google Scholar 

  41. 41.

    Lubes G, Goodarzi M. Analysis of volatile compounds by advanced analytical techniques and multivariate chemometrics. Chem Rev. 2017;117:6399–422.

    Article  CAS  PubMed  Google Scholar 

  42. 42.

    Ho TD, Yu H, Cole WTS, Anderson JL. Ultraviolet photoinitiated on-fiber copolymerization of ionic liquid sorbent coatings for headspace and direct immersion solid-phase microextraction. Anal Chem. 2012;84:9520–8.

    Article  CAS  PubMed  Google Scholar 

  43. 43.

    Ho TD, Toledo BR, Hantao LW, Anderson JL. Chemical immobilization of crosslinked polymeric ionic liquids on nitinol wires produces highly robust sorbent coatings for solid-phase microextraction. Anal Chim Acta. 2014;843:18–26.

    Article  CAS  PubMed  Google Scholar 

  44. 44.

    Jiang R, Pawliszyn J. Thin-film microextraction offers another geometry for solid-phase microextraction. TrAC Trends Anal Chem. 2012;39:245–53.

    Article  CAS  Google Scholar 

  45. 45.

    Joshi MD, Ho TD, Cole WTS, Anderson JL. Determination of polychlorinated biphenyls in ocean water and bovine milk using crosslinked polymeric ionic liquid sorbent coatings by solid-phase microextraction. Talanta. 2014;118:172–9.

    Article  CAS  PubMed  Google Scholar 

  46. 46.

    Hantao LW, Toledo BR, De Lima Ribeiro FA, Pizetta M, Pierozzi CG, Furtado EL, et al. Comprehensive two-dimensional gas chromatography combined to multivariate data analysis for detection of disease-resistant clones of Eucalyptus. Talanta. 2013;116:1079–84.

    Article  CAS  PubMed  Google Scholar 

  47. 47.

    López-darias J, Anderson JL, Pino V, Afonso AM. Developing qualitative extraction profiles of coffee aromas utilizing polymeric ionic liquid sorbent coatings in headspace solid-phase microextraction gas chromatography–mass spectrometry. Anal Bioanal Chem. 2011;401:2965–76.

    Article  CAS  PubMed  Google Scholar 

  48. 48.

    Trujillo-Rodríguez MJ, Pino V, Psillakis E, Anderson JL, Ayala JH, Yiantzi E, et al. Vacuum-assisted headspace-solid phase microextraction for determining volatile free fatty acids and phenols. Investigations on the effect of pressure on competitive adsorption phenomena in a multicomponent system. Anal Chim Acta. 2017;962:41–51.

    Article  CAS  PubMed  Google Scholar 

  49. 49.

    Zhang C, Cagliero C, Pierson SA, Anderson JL. Rapid and sensitive analysis of polychlorinated biphenyls and acrylamide in food samples using ionic liquid-based in situ dispersive liquid-liquid microextraction coupled to headspace gas chromatography. J Chromatogr A. 2017;1481:1–11.

    Article  CAS  PubMed  Google Scholar 

  50. 50.

    Rivellino SR, Hantao LW, Risticevic S, Carasek E, Pawliszyn J, Augusto F. Detection of extraction artifacts in the analysis of honey volatiles using comprehensive two-dimensional gas chromatography. Food Chem. 2013;141:1828–33.

    Article  CAS  PubMed  Google Scholar 

  51. 51.

    Santos BR, Elias AM, Coelho GLV. Use of HS-SPME for analysis of the influence of salt concentration and temperature on the activity coefficient at infinite dilution of ethanol-water-salt systems. Fluid Phase Equilib. 2016;429:21–6.

    Article  CAS  Google Scholar 

  52. 52.

    Baltazar QQ, Leininger SK, Anderson JL. Binary ionic liquid mixtures as gas chromatography stationary phases for improving the separation selectivity of alcohols and aromatic compounds. J Chromatogr A. 2008;1182:119–27.

    Article  CAS  PubMed  Google Scholar 

  53. 53.

    Meng Y, Pino V, Anderson JL. Role of counteranions in polymeric ionic liquid-based solid-phase microextraction coatings for the selective extraction of polar compounds. Anal Chim Acta. 2011;687:141–9.

    Article  CAS  PubMed  Google Scholar 

  54. 54.

    Zhang C, Park RA, Anderson JL. Crosslinked structurally-tuned polymeric ionic liquids as stationary phases for the analysis of hydrocarbons in kerosene and diesel fuels by comprehensive two-dimensional gas chromatography. J Chromatogr A. 2016;1440:160–71.

    Article  CAS  PubMed  Google Scholar 

  55. 55.

    Jiang B, Xi Z, Luo M, Zhang Z. Comparison on aroma compounds in Cabernet Sauvignon and Merlot wines from four wine grape-growing regions in China. Food Res Int. 2013;51:482–9.

    Article  CAS  Google Scholar 

  56. 56.

    Culleré L, Escudero A, Cacho J, Ferreira V. Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium quality Spanish aged red wines. J Agric Food Chem. 2004;52:1653–60.

    Article  CAS  PubMed  Google Scholar 

  57. 57.

    Robinson AL, Boss PK, Solomon PS, Trengove RD, Heymann H, Ebeler SE. Origins of grape and wine aroma. Part 1. Chemical components and viticultural impacts. Am J Enol Vitic. 2014;65:1–24.

    Article  Google Scholar 

  58. 58.

    Parr WV, Heatherbell D, White KG. Demystifying wine expertise: olfactory threshold, perceptual skill and semantic memory in expert and novice wine judges. Chem Senses. 2002;27:747–55.

    Article  PubMed  Google Scholar 

  59. 59.

    Zalacain A, Marín J, Alonso GL, Salinas MR. Analysis of wine primary aroma compounds by stir bar sorptive extraction. Talanta. 2007;71:1610–5.

    Article  CAS  PubMed  Google Scholar 

  60. 60.

    Selli S, Kürkçüoǧlu M, Kafkas E, Cabaroglu T, Demirci B, Başer KHC, et al. Volatile flavour components of mandarin wine obtained from clementines (Citrus reticula Blanco) extracted by solid-phase microextraction. Flavour Fragr J. 2004;19:413–6.

    Article  CAS  Google Scholar 

  61. 61.

    Parsons BA, Pinkerton DK, Wright BW, Synovec RE. Chemical characterization of the acid alteration of diesel fuel: non-targeted analysis by two-dimensional gas chromatography coupled with time-of-flight mass spectrometry with tile-based Fisher ratio and combinatorial threshold determination. J Chromatogr A. 2016;1440:179–90.

    Article  CAS  PubMed  Google Scholar 

  62. 62.

    Marney LC, Christopher Siegler W, Parsons BA, Hoggard JC, Wright BW, Synovec RE. Tile-based Fisher-ratio software for improved feature selection analysis of comprehensive two-dimensional gas chromatography–time-of-flight mass spectrometry data. Talanta. 2013;115:887–95.

    Article  CAS  PubMed  Google Scholar 

  63. 63.

    Oliveira LF, Braga SCGN, Augusto F, Hashimoto JC, Efraim P, Poppi RJ. Differentiation of cocoa nibs from distinct origins using comprehensive two-dimensional gas chromatography and multivariate analysis. Food Res Int. 2016;90:133–8.

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

We are indebted to Danilo Pierone and Alexandre Bogdanovic (Nova Analítica Imp. Exp.) for establishing our laboratory (L. Hantao) by generously providing Thermo Scientific instruments. Camila Frias and Sabrina Homma are thanked for assisting in the initial SPME method development. The National Council for Scientific and Technological Development (CNPq 400182/2016-5), São Paulo Research Foundation (FAPESP 2015/05059-9), and Unicamp (FAEPEX 519.292) are acknowledged for funding our research. J. Crucello and V. Ferreira thank the Coordination for the Improvement of Higher Education Personnel (CAPES) and CNPq for research fellowships. J. Anderson acknowledges funding from the Chemical Measurement and Imaging Program of the National Science Foundation (CHE-1709372).

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Correspondence to Leandro W. Hantao.

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Published in the topical collection Ionic Liquids as Tunable Materials in (Bio)Analytical Chemistry with guest editors Jared L. Anderson and Kevin D. Clark.

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Crucello, J., Miron, L.F.O., Ferreira, V.H.C. et al. Characterization of the aroma profile of novel Brazilian wines by solid-phase microextraction using polymeric ionic liquid sorbent coatings. Anal Bioanal Chem 410, 4749–4762 (2018). https://doi.org/10.1007/s00216-018-1134-3

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Keywords

  • Biomarkers
  • Flavor and aroma
  • Food chemistry
  • Foodomics
  • Sensomics