Skip to main content
SpringerLink
Log in

Migration of phenolic compounds from different cork stoppers to wine model solutions: antioxidant and biological relevance

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

Considering the enological interest of cork, this study aimed to identify and quantify the phenolic compounds able to migrate from different classes (natural cork stoppers “Flor” and “Third” quality and microagglomerate cork stopper) of cork stoppers into bottled wine model solutions. Another aim was to evaluate some antioxidant and biological features of cork phenolics that migrated into the wine model solutions. The main phenolic acids and aldehydes detected were as follows: gallic and protocatechuic acid detected both around 3.5 mg/L and vanillin and protocatechuic aldehyde detected around 2.5 and 1.5 mg/L after 27 months of bottling, respectively. Trace amounts of more complex polyphenols, namely hydrolysable tannins (castalagin/vescalagin and mongolicain A/B), were also detected. Two antioxidant features of the wine model solutions bottled with different wine cork stoppers were studied, namely the antiradical capacity and the reducing capacity, being the natural cork stoppers the ones with the higher activities. The intestinal absorption of the compounds in each wine model solution after 27 months in bottled was evaluated. The simpler phenolic compounds were able to cross Caco-2 cell model. The antiproliferative activity of the same wine model solutions was also evaluated against gastric and breast cancer cells. All samples were active against the two cell lines, which highlight the possible health outcomes of wine sealed with cork stoppers.

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
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Casey J (1994) Is cork a good seal for wine? Aust Grapegrow Winemak 372:39–41

    Google Scholar 

  2. Jung R, Hamatscheck J (1992) Structure and characteristics of natural cork in relation to its use as closure material for bottles. Wein-Wiss 47:226–234

    Google Scholar 

  3. Oliveira V, Knapic S, Pereira H (2013) Classification modeling based on surface porosity for the grading of natural cork stoppers for quality wines. Food Bioprod Process. doi:10.1016/j.fbp.2013.11.004

  4. Gonzalez-Adrados JR, Pereira H (1996) Classification of defects in cork planks using image analysis. Wood Sci Technol 30(3):207–215

    Article  CAS  Google Scholar 

  5. Pereira H, Lopes F, Graça J (1996) The evaluation of the quality of cork planks by image analysis. Holzforschung 50(2):111–115

    Article  CAS  Google Scholar 

  6. Oliveira V, Knapic S, Pereira H (2012) Natural variability of surface porosity of wine cork stoppers of different commercial classes. J Int des Sci de la Vigne et du Vin 46(4):331–340

    Google Scholar 

  7. Karbowiak T, Gougeon RD, Alinc JB, Brachais L, Debeaufort F, Voilley A, Chassagne D (2010) Wine oxidation and the role of cork. Crit Rev Food Sci Nutr 50(1):20–52. doi:10.1080/10408390802248585

    Article  CAS  Google Scholar 

  8. Pereira H (1988) Chemical composition and variability of cork from Quercus suber L. Wood Sci Technol 22(3):211–218

    Article  CAS  Google Scholar 

  9. Rocha SM, Ganito S, Barros A, Carapuça HM, Delgadillo I (2005) Study of cork (from Quercus suber L.)-wine model interactions based on voltammetric multivariate analysis. Anal Chim Acta 528(2):147–156

    Article  CAS  Google Scholar 

  10. Varea S, Garcia-Vallejo MC, Cadahia E, de Simon BF (2001) Polyphenols susceptible to migrate from cork stoppers to wine. Eur Food Res Technol 213(1):56–61

    Article  CAS  Google Scholar 

  11. Schwarz M, Jerz G, Winterhalter P (2003) Isolation and structure of Pinotin A, a new anthocyanin derivative from Pinotage wine. Vitis 42(2):105–106

    CAS  Google Scholar 

  12. Oliveira J, de Freitas V, Silva AMS, Mateus N (2007) Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins. J Agric Food Chem 55(15):6349–6356. doi:10.1021/jf070968f

    Article  CAS  Google Scholar 

  13. Marin AB, Jorgensen EM, Kennedy JA, Ferrier J (2007) Effects of bottle closure type on consumer perceptions of wine quality. Am J Enol Vitic 58(2):182–191

    Google Scholar 

  14. Fernandes A, Fernandes I, Cruz L, Mateus N, Cabral M, de Freitas V (2009) Antioxidant and biological properties of bioactive phenolic compounds from Quercus suber L. J Agric Food Chem 57(23):11154–11160. doi:10.1021/jf902093m

    Article  CAS  Google Scholar 

  15. Azevedo J, Fernandes I, Faria A, Oliveira J, Fernandes A, de Freitas V, Mateus N (2009) Antioxidant properties of anthocyanidins, anthocyanidin-3-glucosides and respective portisins. Food Chem 119(2):518–523. doi:10.1016/j.foodchem.2009.06.050

    Article  Google Scholar 

  16. Benzie IF, Strain JJ (1996) The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Anal Biochem 239(1):70–76

    Article  CAS  Google Scholar 

  17. Fernandes I, Faria A, Azevedo J, Soares S, Calhau C, de Freitas V, Mateus N (2010) Influence of anthocyanins, derivative pigments and other catechol and pyrogallol-type phenolics on breast cancer cell proliferation. J Agric Food Chem 58(6):3785–3792. doi:10.1021/jf903714z

    Article  CAS  Google Scholar 

  18. Sefton MA, Simpson RF (2005) Compounds causing cork taint and the factors affecting their transfer from natural cork closures to wine–a review. Aust J Grape Wine Res 11(2):226–240. doi:10.1111/j.1755-0238.2005.tb00290.x

    Article  CAS  Google Scholar 

  19. Fernandes A, Sousa A, Mateus N, Cabral M, de Freitas V (2011) Analysis of phenolic compounds in cork from Quercus suber L. by HPLC–DAD/ESI–MS. Food Chem 125(4):1398–1405. doi:10.1016/j.foodchem.2010.10.016

    Article  CAS  Google Scholar 

  20. Manach C, Williamson G, Morand C, Scalbert A, Rémésy C (2005) Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr 81(1):230S–242S

    CAS  Google Scholar 

  21. Williamson G, Clifford M (2010) Colonic metabolites of berry polyphenols: the missing link to biological activity? Br J Nutr 104:S48–S66. doi:10.1017/S0007114510003946

    Article  CAS  Google Scholar 

  22. Kroon PA, Clifford MN, Crozier A, Day AJ, Donovan JL, Manach C, Williamson G (2004) How should we assess the effects of exposure to dietary polyphenols in vitro? Am J Clin Nutr 80(1):15–21

    CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by FCT (Fundação para a Ciência e Tecnologia) (POCI, FEDER, POPH, QREN) by the studentship grant (SFRH/BPD/86173/2012). The authors also want to thank BIOCORK Project no. 11430 for the financial support.

Conflict of interest

None.

Compliance with Ethics Requirements

This article does not contain any studies with human or animal subjects.

Author information

Authors and Affiliations

  1. Centro de Investigação em Química (CIQ), Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007, Porto, Portugal

    J. Azevedo, I. Fernandes, N. Mateus & V. Freitas

  2. Amorim e Irmãos S.A, Rua dos Corticeiros 830, 4536-904, Santa Maria de Lamas, Portugal

    P. Lopes, I. Roseira & M. Cabral

Authors
  1. J. Azevedo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. Fernandes
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. Lopes
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. Roseira
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Cabral
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. N. Mateus
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. V. Freitas
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. Freitas.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Azevedo, J., Fernandes, I., Lopes, P. et al. Migration of phenolic compounds from different cork stoppers to wine model solutions: antioxidant and biological relevance. Eur Food Res Technol 239, 951–960 (2014). https://doi.org/10.1007/s00217-014-2292-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-014-2292-y

Keywords

Search

Navigation