Skip to main content
SpringerLink
Log in

Quantification of hydroxycinnamic derivatives in wines by UHPLC-MRM-MS

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

A UHPLC-MS/MS method was developed for the quantification of the main compounds involved in oxidation reactions occurring in white musts and wines such as hydroxycinnamic acids, their glutathione and cysteinylglycine adducts (GRP, GRP2, 5-(S-glutathionyl)-trans-caftaric acid, 2-(S-cysteinylglycyl)-trans-caftaric acid, and 2-(S-glutathionyl)-trans-caffeic acid), and reduced and oxidized glutathione (GSH, GSSG) in wine. Since oxidation is the main concern in white wine-making, directly affecting its quality, the developed method was then applied in a series of white wines made with different pre-fermentation treatments to limit oxidation at must stage. The glucose esters and/or glucosides of hydroxycinnamic acids were quantified as glucogallin equivalent. The developed method led to an overall improvement in the limits of detection (LODs) and quantification (LOQs) for all the compounds studied in comparison to other methods such as high-performance liquid chromatography with fluorescence detection (HPLC-FLD) or diode array UV detection (HPLC-DAD). LOD values ranged from 0.0002 to 0.0140 mg/L and LOQs from 0.0005 to 0.0470 mg/L. The recoveries ranged between 80 and 110% in wines, and the relative standard deviation (RSD) for precision intra- and inter-day was below 15%. The accuracy and intra- and inter-day precision met the acceptance criteria of the AOAC international norms. As far as we know, this study is the first report of quantification of GRP, 2-(S-cysteinylglycyl)-trans-caftaric acid, and 2-(S-glutathionyl)-trans-caffeic acid using these non-commercially available compounds as external standards. Those compounds represent a significant proportion of hydroxycinnamic acid derivatives in wines. The methodology described is suitable for the analysis of hydroxycinnamic derivatives in wines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Artero A, Artero A, Tarín JJ, Cano A. The impact of moderate wine consumption on health. Maturitas. 2015;80:3–13.

    Article  CAS  PubMed  Google Scholar 

  2. Singleton VL, Timberlake CF, Lea AGH. The phenolic cinnamates of white grapes and wine. J Sci Food Agric. 1978;29(4):403–10.

    Article  CAS  Google Scholar 

  3. Singleton VL, Zaya J, Trousdale E, Salgues M. Caftaric acid in grapes and conversion to a reaction product during processing. Vitis. 1984;23(2):113–20.

    CAS  Google Scholar 

  4. Singleton VL, Salgues M, Zaya J, Trousdale E. Caftaric acid disappearance and conversion to products of enzymatic oxidation in grape must and wine. Am J Enol Vitic. 1985;36(1):50–6.

    CAS  Google Scholar 

  5. Cheynier VF, Trousdale EK, Singleton VL, Salgues MJ, Wylde R. Characterization of 2-S-glutathionyl caftaric acid and its hydrolysis in relation to grape wines. J Agric Food Chem. 1986;34(2):217–21.

    Article  CAS  Google Scholar 

  6. Salgues M, Cheynier V, Gunata Z, Wylde R. Oxidation of grape juice 2-S-glutathionyl caffeoyl tartaric acid by Botrytis cinerea laccase and characterization of a new substance: 2,5-di-S-glutathionyl caffeoyl tartaric acid. J Food Sci. 1986;51(5):1191–4.

    Article  CAS  Google Scholar 

  7. Cheynier VF, Van Hulst MWJ. Oxidation of trans-caftaric acid and 2-S-glutathionyl caftaric acid model solutions. J Agric Food Chem. 1988;36(1):10–5.

    Article  CAS  Google Scholar 

  8. Cejudo-Bastante MJ, Perez-Coello MS, Hermosín-Gutiérrez I. Identification of new derivatives of 2-S-glutathionylcaftaric acid in aged white wines by HPLC-DAD-ESI-MSn. J Agric Food Chem. 2010;58(21):11483–92.

    Article  CAS  PubMed  Google Scholar 

  9. Ferreira-Lima N, Vallverdú-Queralt A, Meudec E, Mazauric JP, Sommerer N, Bordignon-Luiz MT, et al. Synthesis, identification, and structure elucidation of adducts formed by reactions of hydroxycinnamic acids with glutathione or cysteinylglycine. J Nat Prod. 2016;79(9):2211–22.

    Article  CAS  PubMed  Google Scholar 

  10. Vallverdú-Queralt A, Verbaere A, Meudec E, Cheynier V, Sommerer N. Straightforward method to quantify GSH, GSSG, GRP, and hydroxycinnamic acids in wines by UPLC-MRM-MS. J Agric Food Chem. 2015;63(1):142–9.

    Article  CAS  PubMed  Google Scholar 

  11. FDA, Food and Drug Administration. U. S. Department of Health and Human Services, Center for Drug Evaluation and Research. In: Bioanalytical Method Validation. FDA. 2013;1–28. Available at: http://www.fda.gov/downloads/drugs/guidancecomplianceregulatoryinformation/guidances/ucm368107.pdf. Accessed 02 Nov 2016.

  12. Baderschneider B, Winterhalter P. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity. J Agric Food Chem. 2001;49(6):2788–98.

    Article  CAS  PubMed  Google Scholar 

  13. Alberts P, Applications of liquid chromatography–tandem mass spectrometry to wine analysis: targeted analysis and compound identification. In: PhD thesis, Stellenbosch University, Stellenbosch, South Africa. 2012. https://scholar.sun.ac.za/handle/10019.1/71693. Accessed Nov 2016.

  14. Janeš L, Lisjak K, Vanzo A. Determination of glutathione content in grape juice and wine by high-performance liquid chromatography with fluorescence detection. Anal Chim Acta. 2010;674(2):239–42.

    Article  CAS  PubMed  Google Scholar 

  15. Porgalı E, Büyüktuncel E. Determination of phenolic composition and antioxidant capacity of native red wines by high performance liquid chromatography and spectrophotometric methods. Food Res Int. 2012;45(1):145–54.

    Article  CAS  Google Scholar 

  16. Anastasiadi M, Pratsinis H, Kletsas D, Skaltsounis AL, Haroutounian SA. Bioactive non-colored polyphenols content of grapes, wines and vinification by-products: evaluation of the antioxidant activities of their extracts. Food Res Int. 2010;43(3):805–13.

    Article  CAS  Google Scholar 

  17. Silva CL, Pereira J, Wouter VG, Giró C, Câmara JSA. Fast method using a new hydrophilic-lipophilic balanced sorbent in combination with ultra-high performance liquid chromatography for quantification of significant bioactive metabolites in wines. Talanta. 2011;86(30):82–90.

    Article  CAS  PubMed  Google Scholar 

  18. Cheynier V, Rigaud J, Moutounet M. Oxidation kinetics of trans-caffeoyltartrate and its glutathione derivatives in grape musts. Phytochemistry. 1990;29(6):1751–3.

    Article  CAS  Google Scholar 

  19. Sonni F, Clark AC, Prenzler PD, Riponi C, Scollary GR. White wine antioxidant action of glutathione and the ascorbic acid/glutathione pair in a model. J Agric Food Chem. 2011;59(8):3940–9.

    Article  CAS  PubMed  Google Scholar 

  20. Danilewicz JC. Reactions involving iron in mediating catechol oxidation in model wine. Am J Enol Vitic. 2013;64(1):316–24.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge Coordenção de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) for the financial support of a doctoral sandwich program at Plateforme Polyphénols, UMR SPO, INRA, for N. Ferreira-Lima. Funding for this work was provided by the Instituto de Salud Carlos III, ISCIII (CIBEROBN). Financial support from GIS Infrastructures en Biologie Santé et Agronomie (IBiSA), Région Languedoc Roussillon, and INRA CNOC for funding of the UHPLC-MS and NMR equipment is also acknowledged.

Author information

Authors and Affiliations

  1. Plateforme Polyphénols, SPO, INRA, Montpellier SupAgro, Université de Montpellier, 2 place Viala, 34060, Montpellier, France

    Nayla Ferreira-Lima, Anna Vallverdú-Queralt, Emmanuelle Meudec, Lucie Pinasseau, Arnaud Verbaere, Christine Le Guernevé, Véronique Cheynier & Nicolas Sommerer

  2. Departamento de Ciência e Tecnologia de Alimentos CAL/CCA, Universidade Federal de Santa Catarina, Rod. Admar Gonzaga, 1346, Itacorubi, Florianópolis, SC, 88034-001, Brazil

    Nayla Ferreira-Lima & Marilde T. Bordignon-Luiz

Authors
  1. Nayla Ferreira-Lima
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anna Vallverdú-Queralt
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Emmanuelle Meudec
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lucie Pinasseau
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Arnaud Verbaere
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Marilde T. Bordignon-Luiz
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Christine Le Guernevé
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Véronique Cheynier
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Nicolas Sommerer
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Nayla Ferreira-Lima or Anna Vallverdú-Queralt.

Ethics declarations

Conflict of interest

The authors declare that they have no conflicts of interest.

Additional information

Published in the topical collection Discovery of Bioactive Compounds with guest editors Aldo Laganà, Anna Laura Capriotti and Chiara Cavaliere.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ferreira-Lima, N., Vallverdú-Queralt, A., Meudec, E. et al. Quantification of hydroxycinnamic derivatives in wines by UHPLC-MRM-MS. Anal Bioanal Chem 410, 3483–3490 (2018). https://doi.org/10.1007/s00216-017-0759-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-017-0759-y

Keywords

Search

Navigation