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J Chromatogr A. 2019 Oct 25;1604:460467. doi: 10.1016/j.chroma.2019.460467. Epub 2019 Aug 20.

Validation of an ultra-high-performance liquid chromatography-mass spectrometry method for the quantification of cysteinylated aldehydes and application to malt and beer samples.

Author information

1
KU Leuven, Department of Microbial and Molecular Systems (M²S), Cluster for Bioengineering Technology (CBeT), Laboratory of Enzyme, Fermentation and Brewing Technology (EFBT), Technology Campus Ghent, Gebroeders De Smetstraat 1, B-9000 Ghent, Belgium. Electronic address: paula.bustillotrueba@kuleuven.be.
2
Ghent University, Faculty of Bioscience Engineering, Department of Biotechnology, Laboratory for Brewing Science & Technology, Valentin Vaerwyckweg 1, B-9000 Ghent, Belgium. Electronic address: barbara.jaskulagoiris@kuleuven.be.
3
Ghent University, Faculty of Bioscience Engineering, Department of Biotechnology, Laboratory for Brewing Science & Technology, Valentin Vaerwyckweg 1, B-9000 Ghent, Belgium; University College Ghent, Faculty of Science and Technology, Department of Biosciences and Food Sciences, Laboratory for Brewing Science & Technology, Valentin Vaerwyckweg 1, B-9000 Ghent, Belgium. Electronic address: jessika.declippeleer@ugent.be.
4
KU Leuven, Department of Microbial and Molecular Systems (M²S), Cluster for Bioengineering Technology (CBeT), Laboratory of Enzyme, Fermentation and Brewing Technology (EFBT), Technology Campus Ghent, Gebroeders De Smetstraat 1, B-9000 Ghent, Belgium.
5
KU Leuven, Department of Microbial and Molecular Systems (M²S), Cluster for Bioengineering Technology (CBeT), Laboratory of Enzyme, Fermentation and Brewing Technology (EFBT), Technology Campus Ghent, Gebroeders De Smetstraat 1, B-9000 Ghent, Belgium. Electronic address: TPraet@kalsec.com.
6
KU Leuven, Department of Chemistry, Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Celestijnenlaan 200F, B-3001 Heverlee, Belgium. Electronic address: usharma81@gmail.com.
7
KU Leuven, Department of Chemistry, Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Celestijnenlaan 200F, B-3001 Heverlee, Belgium; Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, Moscow, 117198 Russian Federation. Electronic address: erik.vandereycken@kuleuven.be.
8
Wageningen University, Laboratory of Food Chemistry, P.O. Box 17, 6700 AA Wageningen, the Netherlands. Electronic address: mark.sanders@wur.nl.
9
Wageningen University, Laboratory of Food Chemistry, P.O. Box 17, 6700 AA Wageningen, the Netherlands. Electronic address: jean-paul.vincken@wur.nl.
10
KU Leuven, Department of Microbial and Molecular Systems (M²S), Cluster for Bioengineering Technology (CBeT), Laboratory of Enzyme, Fermentation and Brewing Technology (EFBT), Technology Campus Ghent, Gebroeders De Smetstraat 1, B-9000 Ghent, Belgium. Electronic address: jos.debrabanter@kuleuven.be.
11
KU Leuven, Department of Microbial and Molecular Systems (M²S), Cluster for Bioengineering Technology (CBeT), Laboratory of Enzyme, Fermentation and Brewing Technology (EFBT), Technology Campus Ghent, Gebroeders De Smetstraat 1, B-9000 Ghent, Belgium. Electronic address: gert.derouck@kuleuven.be.
12
KU Leuven, Department of Microbial and Molecular Systems (M²S), Cluster for Bioengineering Technology (CBeT), Laboratory of Enzyme, Fermentation and Brewing Technology (EFBT), Technology Campus Ghent, Gebroeders De Smetstraat 1, B-9000 Ghent, Belgium. Electronic address: guido.aerts@kuleuven.be.
13
KU Leuven, Department of Microbial and Molecular Systems (M²S), Cluster for Bioengineering Technology (CBeT), Laboratory of Enzyme, Fermentation and Brewing Technology (EFBT), Technology Campus Ghent, Gebroeders De Smetstraat 1, B-9000 Ghent, Belgium. Electronic address: luc.decooman@kuleuven.be.

Abstract

This paper describes the method validation for the simultaneous determination of seven cysteinylated aldehydes, i.e. 2-substituted 1,3-thiazolidines-4-carboxylic acids, using ultra-high-performance liquid chromatography-mass spectrometry (UHPLC-MS). Authentic reference compounds were first synthesized for identification and quantification purposes. Moreover, nuclear magnetic resonance (1H NMR and 13C NMR) was applied for verification of their structure, while ultra-high-performance liquid chromatography-mass spectrometry (UHPLC-MS) was applied for estimation of the purity. The method for quantification of cysteinylated aldehydes in model solutions has been validated according to the criteria and procedures described in international standards. The synthesized compounds were successfully identified via UHPLC-MS by comparing retention time and MS spectra with the commercial reference compounds. Method validation revealed good linearity (R2 > 0.995) over the range of 0.4-2.2 µg/L to approximately 1000 µg/L, depending on the analyte. The limits of quantification varied from 0.9 to 4.3 µg/L depending on the nature of the compound. Furthermore, evaluation of the method showed good accuracy and stability of the standard solutions. Reported chromatographic recoveries ranged from 112 to 120%. Consequently, the currently described method was applied on malt and beer samples. For the first time, quantification of cysteinylated aldehydes was obtained in malt. In contrast, in fresh beers unambiguous identification of these compounds was not achieved.

KEYWORDS:

2-substituted 1,3-thiazolidine-4-carboxylic acids; Beer; Cysteinylated aldehydes; Liquid chromatography-mass spectrometry; Malt; Method validation

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