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Highly sensitive analysis of low-molecular-mass aldehydes in beverages using a hydroxylamine reagent by high-performance liquid chromatography with fluorescence detection

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Abstract

In this study, a fluorescent reagent, 4-((aminooxy)methyl)-7-hydroxycoumarin (AOHC), was for the first time applied to label the low-molecular-mass aldehydes (LMMAs) through reductive oxyamination reaction to afford single N,O-substituted oxyamine derivatives at room temperatures with derivatization efficiencies as high as 96.8%. In the following high-performance liquid chromatography with fluorescence detection analysis, 12 LMMAs, including furfurals, aromatic aldehydes, and aliphatic aldehydes, were baseline-separated on an ODS column and detected with low limits of detection (LODs) (0.2–50 nM), and good precisions (intraday relative standard deviations [RSDs] were 2.40–4.68%, and interday RSDs were 4.65–8.91%). This approach was then adopted to analyze six alcoholic beverages and five dairy products, and nine LMMAs with concentrations in the 0.28–798.16 μM range were successfully detected with excellent accuracies (recoveries were 92.2–106.2%). Finally, the results were statistically analyzed and discussed. The proposed method has several advantages, including high sensitivity, room-temperature labeling, and the avoidance of further extraction and/or enrichment procedures, demonstrating its great utility for monitoring LMMAs in various complex matrices.

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References

  1. Medina-Navarro R, Nieto-Aguilar R, Alvares-Aguilar C. Protein conjugated with aldehydes derived from lipid peroxidation as an independent parameter of the carbonyl stress in the kidney damage. Lipids Health and Dis. 2011;10:201. https://doi.org/10.1186/1476-511X-10-201.

    Article  CAS  Google Scholar 

  2. Lovell MA, Xie C, Markesbery WR. Acrolein is increased in Alzheimer’s disease brain and is toxic to primary hippocampal cultures. Neurobiol Aging. 2001;22(2):187–94. https://doi.org/10.1016/S0197-4580(00)00235-9.

    Article  CAS  PubMed  Google Scholar 

  3. Secretan B, Straif K, Baan R, Grosse Y, El Ghissassi F, Bouvard V, et al. A review of human carcinogens-Part E: tobacco, areca nut, alcohol, coal smoke, and salted fish. Lancet Oncol. 2009;10(11):1033–4. https://doi.org/10.1016/S1470-2045(09)70326-2.

    Article  PubMed  Google Scholar 

  4. Xu ML, Yu Y, Ramaswamy HS, Zhu SM. Characterization of Chinese liquor aroma components during aging process and liquor age discrimination using gas chromatography combined with multivariable statistics. Sci Rep. 2017;7:39671. https://doi.org/10.1038/srep39671.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Shetty SA, Rangiah K. Simple click chemistry-based derivatization to quantify endogenous formaldehyde in milk using ultra-high-performance liquid chromatography/tandem mass spectrometry in selected reaction monitoring mode. Rapid Commun Mass Sp. 2020;34(19):e8865. https://doi.org/10.1002/rcm.8865.

    Article  CAS  Google Scholar 

  6. Demirhan BE, Demirhan SC, Torul H, et al. Short communication: determination of potential 5-hydroxymethyl-2-furaldehyde and 2-furaldehyde compounds in follow-on milks and infant formulas using the high-performance liquid chromatography method. J Dairy Sci. 2015;98(2):818–22. https://doi.org/10.3168/jds.2014-8761.

    Article  CAS  PubMed  Google Scholar 

  7. Wang W, Qing-Feng YU, Xiao Y, Hua HE. University CP Rapid determination of long-chain aliphatic aldehyde in gutter oil by fluorescent derivatization-high performance liquid chromatography. Chinese J Anal Chem. 2017;45(5):770–6. https://doi.org/10.11895/j.issn.0253-3820.160893.

    Article  CAS  Google Scholar 

  8. Wietstock PC, Kunz T, Methner FJ. Relevance of oxygen for the formation of strecker aldehydes during beer production and storage. J Agr Food Chem. 2016;64(42):8035–44. https://doi.org/10.1021/acs.jafc.6b03502.

    Article  CAS  Google Scholar 

  9. Mina M, Tsaltas D. Contribution of yeast in wine aroma and flavour. In: Antonio Morata, editors. Yeast-Industrial Applications. U.S.A; 2017. Chapter 5. https://doi.org/10.5772/intechopen.70656.

  10. Rodríguez DMO, Wrobel K, Wrobel K. Determination of aldehydes in tequila by high-performance liquid chromatography with 2,4-dinitrophenylhydrazine derivatization. Eur Food Res Technol. 2005;221(6):798–802. https://doi.org/10.1007/s00217-005-0038-6.

    Article  CAS  Google Scholar 

  11. Donnarumma F, Wintersteiger R, Schober M, Greilberger J, Matzi V, Maier A, et al. Simultaneous quantitation of alpha-ketoglutaric acid and 5-hydroxymethylfurfural in plasma by HPLC with UV and fluorescence detection. Anal Sci. 2013;29(12):1177–82. https://doi.org/10.2116/analsci.29.1177.

    Article  CAS  PubMed  Google Scholar 

  12. Zhang A, Guan ZB, Cai HW, Huang YY, Lin YW, Hu XS. Nitrone formation: a new strategy for the derivatization of aldehydes and its application on the determination of furfurals in foods by high performance liquid chromatography with fluorescence detection. Talanta. 2018;178:834–41. https://doi.org/10.1016/j.talanta.2017.10.027.

    Article  CAS  PubMed  Google Scholar 

  13. Resconi VC, Campo MM, Montossi F, Ferreira V, Sanudo C, Escudero A. Relationship between odour-active compounds and flavour perception in meat from lambs fed different diets. Meat Sci. 2010;85(4):700–6. https://doi.org/10.1016/j.meatsci.2010.03.027.

    Article  CAS  PubMed  Google Scholar 

  14. Ding MM, Guan ZB, Cai HW, Huang YY, Lin YW, Hu XS. Reductive oxyamination: a method for the qualitative and quantitative analysis of monosaccharides with a new aminooxy reagent using high-performance liquid chromatography with fluorescence detection. Anal Bioanal Chem. 2018;410(1):79–89. https://doi.org/10.1007/s00216-017-0693-z.

    Article  CAS  PubMed  Google Scholar 

  15. Guo P, Yan SY, Hu JL, Xing XW, Wang CC, Xu XW, et al. Selective detection of 5-formyl-2’-deoxycytidine in DNA using a fluorogenic hydroxylamine reagent. Org Lett. 2013;15(13):3266–9. https://doi.org/10.1021/ol401290d.

    Article  CAS  PubMed  Google Scholar 

  16. Chen L, Fu YJ, Fang WL, Guo XF, Wang H. Screening of a highly effective fluorescent derivatization reagent for carbonyl compounds and its application in HPLC with fluorescence detection. Talanta. 2018;186:221–8. https://doi.org/10.1016/j.talanta.2018.04.017.

    Article  CAS  PubMed  Google Scholar 

  17. Brouwer AM. Standards for photoluminescence quantum yield measurements in solution. Pure Appl Chem. 2011;83(12):2213–28. https://doi.org/10.1351/PAC-REP-10-09-31.

    Article  CAS  Google Scholar 

  18. Brodie RR, Hill HM. Validation issues arising from the new FDA guidance for industry on bioanalytical method validation. Chromatographia. 2002;55:S91–4. https://doi.org/10.1007/BF02493361.

    Article  CAS  Google Scholar 

  19. Uchiyama S, Inaba Y, Matsumoto M, Suzuki G. Reductive amination of aldehyde 2,4 dinitorophenylhydrazones using 2-picoline borane and high-performance liquid chromatographic analysis. Anal Chem. 2009;81(1):485–9. https://doi.org/10.1021/ac802163y.

    Article  CAS  PubMed  Google Scholar 

  20. Crisalli P, Kool ET. Water-soluble organocatalysts for hydrazone and oxime formation. J Org Chem. 2013;78(3):1184–9. https://doi.org/10.1002/chin.201325125.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Palvolgyi AM, Scharinger F, Schnurch M, Bica-Schroder K. Chiral phosphoric acids as versatile tools for organocatalytic asymmetric transfer hydrogenations. Eur J Org Chem. 2021;2021(38):5367–81. https://doi.org/10.1002/ejoc.202100894.

    Article  CAS  Google Scholar 

  22. Wu JY, Shi ZG, Feng YQ. Determination of 5-hydroxymethylfurfural using derivatization combined with polymer monolith microextraction by high-performance liquid chromatography. J Agr Food Chem. 2009;57(10):3981–8. https://doi.org/10.1021/jf900434n.

    Article  CAS  Google Scholar 

  23. Carrillo G, Bravo A, Zufall C. Application of factorial designs to study factors involved in the determination of aldehydes present in beer by on-fiber derivatization in combination with gas chromatography and mass spectrometry. J Agr Food Chem. 2011;59(9):4403–11. https://doi.org/10.1021/jf200167h.

    Article  CAS  Google Scholar 

  24. Moreira N, Meireles S, Brandao T, de Pinho PG. Optimization of the HS-SPME–GC–IT/MS method using a central composite design for volatile carbonyl compounds determination in beers. Talanta. 2013;117(22):523–31. https://doi.org/10.1016/j.talanta.2013.09.027.

    Article  CAS  PubMed  Google Scholar 

  25. Hernandes KC, Souza-Silva EA, Assumpcao CF, Zini CA, Welke JE. Validation of an analytical method using HS-SPME-GC/MS-SIM to assess the exposure risk to carbonyl compounds and furan derivatives through beer consumption. Food Addit Contam A. 2019;36(12):1808-21-1808–21.

    Article  Google Scholar 

  26. Gernat DC, Brouwer E, Ottens M. Aldehydes as wort off-flavours in alcohol-free beers-origin and control. Food Bioprocess Tech. 2020;13(2):195–216. https://doi.org/10.1007/s11947-019-02374-z.

    Article  CAS  Google Scholar 

  27. Perederii MA, Tsodikov MV, Uvarov VI. Purification of aqueous alcohol solutions in two-bed adsorber filters. Solid Fuel Chem. 2011;45(1):34–8. https://doi.org/10.3103/S0361521911010101.

    Article  CAS  Google Scholar 

  28. Paiano V, Bianchi G, Davoli E, Negri E, Fanelli R, Fattore E. Risk assessment for the Italian population of acetaldehyde in alcoholic and non-alcoholic beverages. Food Chem. 2014;154:26–31. https://doi.org/10.1016/j.foodchem.2013.12.098.

    Article  CAS  PubMed  Google Scholar 

  29. Chavez-Servin JL, Castellote AI, Lopez-Sabater MC. Analysis of potential and free furfural compounds in milk-based formulae by high-performance liquid chromatography - Evolution during storage. J Chromatogr A. 2005;1076(1–2):133–40. https://doi.org/10.1016/j.chroma.2005.04.046.

    Article  CAS  PubMed  Google Scholar 

  30. Abraham K, Gurtler R, Berg K, Heinemeyer G, Lampen A, Appel KE. Toxicology and risk assessment of 5-hydroxymethylfurfural in food. Mol Nutr Food Res. 2011;55(5):667–78. https://doi.org/10.1002/mnfr.201000564.

    Article  CAS  PubMed  Google Scholar 

  31. Milani MI, Rossini EL, Castoldi K, Pezza L, Pezza HR. Paper platform for reflectometric determination of furfural and hydroxymethylfurfural in sugarcane liquor. Microchem J. 2017;133:286–92. https://doi.org/10.1016/j.microc.2017.03.046.

    Article  CAS  Google Scholar 

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Funding

We received financial support from the Preventive Medicine (MY19M01 and WJ2019H303 to Y. Lin) and the Fundamental Research Funds for the Central Universities (WUT: 2021IA003 and WUT: 2020IB026 to X. Hu).

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Authors and Affiliations

  1. Department of Chemistry, School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan, 430070, China

    Ran Liu, Long Mao, Zhaobing Guan, Chengsheng Wang, Jing Xu, Lujie Huang, Peike Wang, Guolin Xin, Rui Hu, Chuyu Zhang, Zihan Zhao, Yawei Lin & Xiaosong Hu

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  1. Ran Liu
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  2. Long Mao
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  3. Zhaobing Guan
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Correspondence to Yawei Lin or Xiaosong Hu.

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Liu, R., Mao, L., Guan, Z. et al. Highly sensitive analysis of low-molecular-mass aldehydes in beverages using a hydroxylamine reagent by high-performance liquid chromatography with fluorescence detection. Anal Bioanal Chem 414, 5009–5022 (2022). https://doi.org/10.1007/s00216-022-04132-1

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