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Rapid Analysis of 27 Volatile Sulfur Compounds in Wine by Headspace Solid-Phase Microextraction Gas Chromatography Tandem Mass Spectrometry

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Abstract

Volatile sulfur-containing compounds (VSCs) play an important role in wine aroma conferring at high concentrations unpleasant odors but also participating positively at low concentration. A large number of VSCs are formed at different stages of winemaking and storage. To monitor this phenomenon, a HS-SPME-GC-MS/MS method has been developed. The method is proposed in order to quantify 27 different sulfur-containing compounds. SPME extraction was performed using a carboxen-polydimethylsiloxane (CAR-PDMS) fiber, which resulted the most effective fiber coating. Time and temperature extraction conditions were optimized using response surface methodology. The selectivity and sensitivity of the method were considerably increased using triple-quadrupole in multiple reaction monitoring (MRM) mode. The number of VSCs analyzed in a single run was higher than in any other method previously reported using single-quadrupole MS or other detectors. The overall process was successfully applied to identify and quantify sulfur compounds both in white and red wines.

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References

  • Bolaños PP, Moreno JL, Shtevera DD, Frenich AG, Vidal JL (2007) Development and validation of a multiresidue method for the analisis of 151 pesticide residues in strawberry by gas chromatography coupled to a triple quadrupole analyser. Rapid Commun Mass Spectrom 21:2282–2294. doi:10.1002/rcm.3091

    Article  Google Scholar 

  • Bourdat-Deschamps M, Daudin JJ, Barriuso E (2007) An experimental design approach to optimise the determination of polycyclic aromatic hydrocarbons from rainfall water using stir bar sorptive extraction and high performance liquid chromatography-fluorescence detection. J Chromatogr a 1167:143–153. doi:10.1016/j.chroma.2007.08.025

    Article  CAS  Google Scholar 

  • Burin VM, Marchand S, de Revel G, Bordignon-Luiz MT (2013) Development and validation of method for heterocyclic compounds in wine: optimization of HS-SPME conditions applying a response surface methodology. Talanta 117:87–93. doi:10.1016/j.talanta.2013.08.037

    Article  CAS  Google Scholar 

  • Cervera MI, Medina C, Portoles T, Pitarch E, Beltran J, Serrahima E, Pineda L, Muñoz G, Centrich F, Hernández F (2010) Multi-residue determination of 130 multiclass pesticides in fruits and vegetables by gas chromatography coupled to triple quadrupole tandem mass spectrometry. Anal Bioanal Chem 397:2873–2891. doi:10.1007/s00216-010-3597-8

    Article  CAS  Google Scholar 

  • Commission of the European Communities, Commission Decision 2002/657/EC implementing Council Directive 96/23/EC, concerning the performance of analytical methods and the interpretation of results.

  • Derringer G, Suich R (1980) Simultaneous optimization of several response variables. J Qual Technol 12:214–219

    Google Scholar 

  • Escudero A, Campo E, Farina L, Cacho J, Ferreira V (2007) Analytical characterization of the aroma of five premium red wines. Insights into the Role of Odorfamilies and the Concept of Fruitiness of Wines J Agric Food Chem 55:4501–4510. doi:10.1021/jf0636418

    CAS  Google Scholar 

  • Fang Y, Qian MC (2005) Sensitive quantification of sulfur compounds in wine by headspace solid-phase microextraction technique. J Chromatogr a 1080:177–185. doi:10.1016/j.chroma.2005.05.024

    Article  CAS  Google Scholar 

  • Fedrizzi B, Magno F, Moser S, Nicolini G, Versini G (2007) Concurrent quantification of light and heavy sulphur volatiles in wine by headspace solid-phase microextraction coupled with gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom 21:707–714. doi:10.1002/rcm.2893

    Article  CAS  Google Scholar 

  • Franco-Luesma E, Ferreira V (2014) Quantitative analysis of free and bonded forms of volatile sulfur compouds in wine. Basic methodologies and evidences showing the existence of reversible cation-complexed forms. J Chromatogr a 1359:8–15. doi:10.1016/j.chroma.2014.07.011

    Article  CAS  Google Scholar 

  • Gandolfi F, Malleret L, Sergent M, Doumenq P (2015) Parameters optimization using experimental design for headspace solid phase micro-extraction analysis of short-chain chlorinated paraffins in waters under the European water framework directive. J Chromatogr a 1406:59–67. doi:10.1016/j.chroma.2015.06.030

    Article  CAS  Google Scholar 

  • Genovese A, Dimaggio R, Lisanti MT, Piombino P, Moio L (2005) Aroma composition of red wines by different extraction methods and gas chromatography-SIM/mass spectrometry analysis. Ann Chim 95:383–394. doi:10.1002/adic.200590045

    Article  CAS  Google Scholar 

  • Herszage J, Ebeler SE (2011) Analysis of volatile organic sulfur compounds in wine using headspace solid-phase microextraction gas chromatography with sulfur chemiluminescence detection. Am J Enol Vitic 62:1–8. doi:10.5344/ajev.2010.10099

    Article  CAS  Google Scholar 

  • Jofré PV, Assof MV, Fanzone ML, Goicoechea HC, Martínez LD, Silva MF (2010) Optimization of ultrasound assisted-emulsification-dispersive liquid–liquid microextraction by experimental design methodologies for the determination of sulfur compounds in wines by gas chromatography–mass spectrometry. Anal Chim Acta 683:126–135. doi:10.1016/j.aca.2010.10.010

    Article  Google Scholar 

  • Kinzurik MI, Herbst-Johnstone M, Gardner RC, Fedrizzi B (2015) Evolution of volatile sulfur compounds during wine fermentation. J Agric Food Chem 63:8017–8024. doi:10.1021/acs.jafc.5b02984

    Article  CAS  Google Scholar 

  • Landaud S, Helinck S, Bonnarme P (2008) Formation of volatile sulfur compounds and metabolism of methionine and other sulfur compounds in fermented food. Appl Microbiol Biotechnol 77:1191–1205. doi:10.1007/s00253-007-1288-y

    Article  CAS  Google Scholar 

  • Leardi R (2009) Experimental design in chemistry: a tutorial. Anal Chim Acta 652:161–172. doi:10.1016/j.aca.2009.06.015

    Article  CAS  Google Scholar 

  • Ledauphin J, Basset B, Cohen S, Payot T, Barillier D (2006) Identification of trace volatile compounds in freshly distilled calvados and cognac: carbonyl and sulphur compounds. J Food Compos Anal 19:28–40. doi:10.1016/j.jfca.2005.03.001

    Article  CAS  Google Scholar 

  • Leppanen OA, Denslow J, Ronkainen PP (1980) Determination of thiolacetates and some other volatile sulfur compounds in alcoholic beverages. J Agric Food Chem 28:359–362. doi:10.1021/jf60228a028

    Article  CAS  Google Scholar 

  • Lopez R, Lapena AC, Cacho J, Ferreira V (2007) Quantitative determination of wine highly volatile sulfur compounds by using automated headspace solid-phase microextraction and gas chromatography-pulsed flame photometric detection critical study and optimization of a new procedure. J Chromatogr a 1143:8–15. doi:10.1016/j.chroma.2006.12.053

    Article  CAS  Google Scholar 

  • Loubser GJ, Du Plessis CS (1976) The quantitative determination and some values of dimethyl sulphide in white table wines. Vitis 15:248–252

    CAS  Google Scholar 

  • Majcenovic AB, Schneider R, Lepoutre JP, Lempereur V, Baumes R (2002) Synthesis and stable isotope dilution assay of ethanethiol and diethyl disulfide in wine using solid phase microextraction. Effect of Aging on their Levels in Wine J Agric Food Chem 50:6653–6658. doi:10.1021/jf020478h

    CAS  Google Scholar 

  • Martínez-Vidal JL, Arrebola-Liebanas FJ, González-Rodríguez MJ, Garrido-Frenich A, Fernández-Moreno JL (2006) Validation of a gas chromatography/triple quadrupole mass spectrometry based method for the quantification of pesticides in food commodities. Rapid Commun Mass Spectrom 20:365–375. doi:10.1002/rcm.2315

    Article  Google Scholar 

  • Masuda M, Nishimura K (1982) Changes in volatile sulfur compounds of whisky during aging. J Food Sci 47:101–105. doi:10.1111/j.1365-2621.1982.tb11037.x

    Article  Google Scholar 

  • Mateo-Vivaracho L, Cacho J, Ferreira V (2007) Quantitative determination of wine polyfunctional mercaptans at nanogram per liter level by gas chromatography-negative ion mass spectrometric analysis of their pentafluorobenzyl derivatives. J Chromatogr a 1146:242–250. doi:10.1016/j.chroma.2007.02.003

    Article  CAS  Google Scholar 

  • Mestres M, Busto O, Guasch J (1997) Chromatographic analysis of volatile sulphur compounds in wines using the static headspace technique with flame photometric detection. J Chromatogr a 773:261–269. doi:10.1016/S0021-9673(97)00188-X

    Article  CAS  Google Scholar 

  • Mestres M, Busto O, Guasch J (2000a) Analysis of organic sulfur compounds in wine aroma. J Chromatogr a 881:569–581. doi:10.1016/S0021-9673(00)00220-X

    Article  CAS  Google Scholar 

  • Mestres M, Martí MP, Busto O, Guasch J (2000b) Analysis of low-volatility organic sulphur compounds in wines by solid-phase microextraction and gas chromatography. J Chromatogr a 881:583–590. doi:10.1016/S0021-9673(00)00326-5

    Article  CAS  Google Scholar 

  • Mestres M, Sala C, Martí MP, Busto O, Guasch J (1999) Headspace solid-phase microextraction of sulphides and disulphides using carboxen–polydimethylsiloxane fibers in the analysis of wine aroma. J Chromatogr a 849:137–144. doi:10.1016/S0021-9673(98)01050-4

    Article  Google Scholar 

  • Moreno JLF, Frenich AG, Bolaños PP, Vidal JLM (2008) Multiresidue method for the analysis of more than 140 pesticide residues in fruits and vegetables by gas chromatography coupled to triple quadrupole mass spectrometry. J Mass Spectrom 43:1235–1254. doi:10.1002/jms.1400

    Article  CAS  Google Scholar 

  • Nguyen D-D, Nicolau L, Dykes SI, Kilmartin PA (2010) Influence of microoxygenation on reductive sulfur off-odors and color development in a cabernet sauvignon wine. Am J Enol Vitic 61:457–464

    Article  Google Scholar 

  • Nguyen DDN, Nicolau L, Kilmartin PA (2012) Application of an automated headspace solid phase micro-extraction for the GC–MS detection and quantification of reductive sulfur compounds in wines. In: Salih B (ed) Gas chromatography in plant science, wine technology, toxicology and some specific applications. InTech, Rijeka. Chapter 9, pp 171–195

    Google Scholar 

  • Park SK, Boulton RB, Bartra E, Noble AC (1994) Incidence of volatile sulfur compounds in California wines. A preliminary survey. Am J Enol Vitic 45:341–344

    CAS  Google Scholar 

  • Pripis-Nicolau L, De Revel G, Bertrand A, Lonvaud-Funel A (2004) Methionine catabolism and production of volatile sulphur compounds by OEnococcus oeni. J Appl Microbiol 96:1176–1184. doi:10.1111/j.1365-2672.2004.02257.x

    Article  CAS  Google Scholar 

  • Rauhut D, Kurbel H, MacNamara K, Grossmann M (1998) Headspace GC-SCD monitoring of low volatile sulfur compounds during fermentation and in wine. Analusis 26:142–145. doi:10.1051/analusis:1998124

    Article  CAS  Google Scholar 

  • Rodriguez-Bencomo JJ, Muñoz-González C, Martín-Álvarez PJ, Lázaro E, Mancebo R, Castañé X, Pozo-Bayón MA (2012) Optimization of a HS-SPME-GC-MS procedure for beer volatile profiling using response surface methodology: application to follow aroma stability of beers under different storage conditions. Food Anal Methods 5:1386–1397. doi:10.1007/s12161-012-9390-x

    Article  Google Scholar 

  • Sadoughi N, Schmidtke LM, Antalick G, Blackman JW, Steel CC (2015) Gas chromatography−mass spectrometry method optimized using response surface modeling for the quantitation of fungal off-flavors in grapes and wine. J Agric Food Chem 63:2877–2885. doi:10.1021/jf505444r

    Article  CAS  Google Scholar 

  • Segurel MA, Razungles AJ, Riou C, Salles M, Baumes RL (2004) Contribution of dimethyl sulfide to the aroma of syrah and Grenache noir wines and estimation of its potential in grapes of these varieties. J Agric Food Chem 52:7084–7093. doi:10.1021/jf049160a

    Article  CAS  Google Scholar 

  • Swan HB (2000) Determination of existing and potential dimethyl sulphide in red wines by gas chromatography atomic emission spectroscopy. J Food Compos Anal 13:207–217. doi:10.1006/jfca.2000.0888

    Article  CAS  Google Scholar 

  • Tominaga T, Darriet P, Dubourdieu D (1998) Development of a method for analyzing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. Cv. Sauvignon Blanc. J Agric Food Chem 46:1044–1048. doi:10.1021/jf970782o

    Article  CAS  Google Scholar 

  • Zhang Y, Zhang J (2008) Optimization of headspace solid-phase microextraction for analysis of ethyl carbamate in alcoholic beverages using a face-centered cube central composite design. Anal Chim Acta 627:212–218. doi:10.1016/j.aca.2008.08.014

    Article  CAS  Google Scholar 

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  1. Centro Trasferimento Tecnologico, Fondazione E. Mach, via E. Mach 1, 38010, San Michele all’Adige, TN, Italy

    Davide Slaghenaufi, Loris Tonidandel, Sergio Moser, Tomás Román Villegas & Roberto Larcher

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  1. Davide Slaghenaufi
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  2. Loris Tonidandel
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  3. Sergio Moser
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  4. Tomás Román Villegas
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  5. Roberto Larcher
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Correspondence to Davide Slaghenaufi.

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Dr. Davide Slaghenaufi declares that he has no conflict of interest. Dr. Loris Tonidandel declares that he has no conflict of interest. Dr. Sergio Moser declares that he has no conflict of interest. Dr. Tomás Romanán Villegas declares that he has no conflict of interest. Dr. Roberto Larcher declares that he has no conflict of interest.

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Slaghenaufi, D., Tonidandel, L., Moser, S. et al. Rapid Analysis of 27 Volatile Sulfur Compounds in Wine by Headspace Solid-Phase Microextraction Gas Chromatography Tandem Mass Spectrometry. Food Anal. Methods 10, 3706–3715 (2017). https://doi.org/10.1007/s12161-017-0930-2

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