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Development and Validation of a GC-MS/MS Method for cis- and trans-Resveratrol Determination: Application to Portuguese Wines

  • Sílvia Rocha
  • Ana Margarida Araújo
  • Agostinho Almeida
  • Paula Guedes de Pinho
  • Eduarda FernandesEmail author
Article

Abstract

Resveratrol is a naturally occurring phytoalexin produced by the Vitis vinifera L. plant. It exists as two isomers (cis and trans), both present in wines. This work describes the development and validation of a GC-MS/MS analytical procedure for their determination in wines, which include five steps for sample preparation: pre-treatment, SPE extraction, acetyl derivatization, liquid/liquid extraction, and sample concentration. The developed GC-MS/MS method showed to be linear, with coefficients of determination higher than 0.99 for both isomers, and sensible in the range from 1.0 to 2000.0 μg/L for cis-resveratrol and 5.0 to 2000.0 μg/L for trans-resveratrol. Intra- and inter-day precision evaluation resulted in coefficient of variation values (CV) lower than 15%. The validated methodology was then applied in the determination of resveratrol in 33 red wines (from 8 Portuguese Protected Geographical Indications). For cis-resveratrol the content ranged from 45.8 to 2439.5 μg/L, while for trans-resveratrol it ranged from 45.8 to 2385.0 μg/L. No statistically significant differences were found between the studied regions.

Keywords

Wine Portuguese wine Resveratrol GC-MS/MS Analytical method Validation 

Notes

Funding

This study was funded by the European Union (FEDER funds POCI/01/0145/FEDER/007265) and National Funds (FCT/MEC, Fundação para a Ciência e Tecnologia and Ministério da Educação e Ciência) under the Partnership Agreement PT2020 UID/QUI/50006/2013, and “Programa Operacional Competitividade e Internacionalização” (COMPETE) (PTDC/QEQ-QAN/1742/2014 – POCI-01-0145-FEDER-016530; POCI-01-0145-FEDER-029253), and under the framework of QREN (NORTE-01-0145-FEDER-000024). A. M. Araújo thanks to FCT for her PhD fellowship (SFRH/BD/107708/2015).

Compliance with Ethical Standards

Conflict of Interest

Sílvia Rocha declares that she has no conflict of interest. Ana Margarida Araújo declares that she has no conflict of interest. Agostinho Almeida declares that he has no conflict of interest. Paula Guedes de Pinho declares that she has no conflict of interest. Eduarda Fernandes declares that she has no conflict of interest.

Ethical Approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Informed Consent

Not applicable.

References

  1. Aggarwal BB, Shishodia S (2005) Resveratrol in health and disease, 1st edn. Boca Raton, FloridaGoogle Scholar
  2. Alonso AM, Domínguez C, Guillén DA, Barroso CG (2002) Determination of antioxidant power of red and white wines by a new electrochemical method and its correlation with polyphenolic content. J Agric Food Chem 50(11):3112–3115CrossRefGoogle Scholar
  3. Athar M, Back JH, Tang X, Kim KH, Kopelovich L, Bickers DR, Kim AL (2007) Resveratrol: a review of preclinical studies for human cancer prevention. Toxicol Appl Pharmacol 224(3):274–283CrossRefGoogle Scholar
  4. Baptista JAB, Tavares JFP, Carvalho RCB (2001) Comparison of polyphenols and aroma in red wines from Portuguese mainland versus Azores Islands. Food Res Int 34(4):345–355CrossRefGoogle Scholar
  5. Bertelli AA, Das DK (2009) Grapes, wines, resveratrol, and heart health. J Cardiovasc Pharmacol 54(6):468–476CrossRefGoogle Scholar
  6. Budić-Leto I, Lovrić T, Pezo I, Kljusurić JG (2005) Study of dynamics of polyphenol extraction during traditional and advanced maceration processes of the Babić grape variety. Food Technol Biotechnol 43(1):47–53Google Scholar
  7. Cai L, Koziel JA, Van Leeuwen JH (2009) Rapid determination of trans-resveratrol in red wine by solid-phase microextraction with on-fiber derivatization and multidimensional gas chromatography–mass spectrometry. J Chromatogr A 1216(2):281–287CrossRefGoogle Scholar
  8. Cravero M, Bonello E, Tsolakis C, Piano E, Borsa D (2012) Comparison between Nero d'Avola wines produced with grapes grown in Sicily and Tuscany. Italian Food Bev Technol 73:14–18Google Scholar
  9. Geana EI, Dinca OR, Ionete RE, Artem V, Niculescu VC (2015) Monitoring trans-resveratrol in grape berry skins during ripening and in corresponding wines by HPLC. Food Technol Biotechnol 53(1):73–80CrossRefGoogle Scholar
  10. Goldberg DM, Yan J, Ng E, Diamandis EP, Karumanchiri A, Soleas G, Waterhouse AL (1994) Direct injection gas chromatographic mass spectrometric assay for trans-resveratrol. Anal Chem 66(22):3959–3963CrossRefGoogle Scholar
  11. Goldberg DM, Yan J, Ng E, Diamandis EP, Karumanchiri A, Soleas G, Waterhouse AL (1995) A global survey of trans-resveratrol concentrations in commercial wines. Am J Enol Vitic 46(2):159–165Google Scholar
  12. Guideline IHT (2005) Validation of analytical procedures: text and methodology. Q2(R1):1Google Scholar
  13. Hübschmann HJ (2015) Handbook of GC-MS: fundamentals and applications. vol 1, 2nd edn. Wiley, WeinheimGoogle Scholar
  14. InfoVini. (2017). Produzir Viticultura - Castas Tintas. In: Castas, vol 2017. InfoViniGoogle Scholar
  15. Jeandet P, Bessis R, Gautheron B (1991) The production of resveratrol (3, 5, 4′-trihydroxystilbene) by grape berries in different developmental stages. Am J Enol Vitic 42(1):41–46Google Scholar
  16. Jeandet P, Bessis R, Maume BF, Meunier P, Peyron D, Trollat P (1995) Effect of enological practices on the resveratrol isomer content of wine. J Agric Food Chem 43(2):316–319CrossRefGoogle Scholar
  17. Klenar I, Berovič M, Wondra M (2004) Phenolic compounds from the fermentation of cultivars Cabernet Sauvignon and Merlot from the Slovenian coastal region. Food Technol Biotechnol 42(1):11–17Google Scholar
  18. Lima MTR, Waffo-Téguo P, Teissedre PL, Pujolas A, Vercauteren J, Cabanis JC, Mérillon JM (1999) Determination of stilbenes (trans-astringin, cis- and trans-piceid, and cis- and trans-resveratrol) in Portuguese wines. J Agric Food Chem 47(7):2666–2670CrossRefGoogle Scholar
  19. Montes R, García-López M, Rodríguez I, Cela R (2010) Mixed-mode solid-phase extraction followed by acetylation and gas chromatography mass spectrometry for the reliable determination of trans-resveratrol in wine samples. Anal Chim Acta 673(1):47–53CrossRefGoogle Scholar
  20. Nave F, Cabrita MJ, Costa CT (2007) Use of solid-supported liquid–liquid extraction in the analysis of polyphenols in wine. J Chromatogr A 1169(1):23–30CrossRefGoogle Scholar
  21. Obreque-Slier E a, Peña-Neira A l, López-Solís R, Zamora-Marín F, Ricardo-da Silva JM, Laureano O (2010) Comparative study of the phenolic composition of seeds and skins from Carménère and Cabernet Sauvignon grape varieties (Vitis vinifera L.) during ripening. J Agric Food Chem 58(6):3591–3599CrossRefGoogle Scholar
  22. OIV (2015) Compendium of international methods of wine and must analysis, vol 2. Paris, FranceGoogle Scholar
  23. Paixão N, Pereira V, Marques JC, Câmara JS (2008) Quantification of polyphenols with potential antioxidant properties in wines using reverse phase HPLC. J Sep Sci 31(12):2189–2198CrossRefGoogle Scholar
  24. Paulo L, Ferreira S, Gallardo E, Queiroz JA, Domingues F (2010) Antimicrobial activity and effects of resveratrol on human pathogenic bacteria. World J Microbiol Biotechnol 26(8):1533–1538CrossRefGoogle Scholar
  25. Paulo L, Domingues F, Queiroz JA, Gallardo E (2011) Development and validation of an analytical method for the determination of trans- and cis-resveratrol in wine: analysis of its contents in 186 Portuguese red wines. J Agric Food Chem 59(6):2157–2168CrossRefGoogle Scholar
  26. Pereira V, Câmara JS, Cacho J, Marques JC (2010) HPLC-DAD methodology for the quantification of organic acids, furans and polyphenols by direct injection of wine samples. J Sep Sci 33(9):1204–1215Google Scholar
  27. Ratola N, Faria JL, Alves A (2004) Analysis and quantification of trans-resveratrol in wines from Alentejo region (Portugal). Food Technol Biotechnol 42(2):125–130Google Scholar
  28. Renaud S d, de Lorgeril M (1992) Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 339(8808):1523–1526CrossRefGoogle Scholar
  29. Revel G, Hogg T, Santos C (1996) Analysis of cis-and trans-resveratrol in Portuguese wines. OENO One 30(1):31–37CrossRefGoogle Scholar
  30. Ribeiro B, de Pinho PG, Andrade PB, Baptista P, Valentão P (2009) Fatty acid composition of wild edible mushrooms species: a comparative study. Microchem J 93(1):29–35CrossRefGoogle Scholar
  31. Rodríguez-Cabo T, Rodríguez I, Cela R (2012) Determination of hydroxylated stilbenes in wine by dispersive liquid–liquid microextraction followed by gas chromatography mass spectrometry. J Chromatogr A 1258:21–29CrossRefGoogle Scholar
  32. Sánchez JJ, Corral EC, Delgado MS, Orea J, Ureña AG (2005) Analysis of trans-resveratrol by laser ionization mass spectrometry and HPLC with fluorescence detection: comparison between both techniques. J Chromatogr A 1074(1–2):133–138CrossRefGoogle Scholar
  33. Soleas GJ, Diamandis EP, Karumanchiri A, Goldberg DM (1997) A multiresidue derivatization gas chromatographic assay for fifteen phenolic constituents with mass selective detection. Anal Chem 69(21):4405–4409CrossRefGoogle Scholar
  34. Sun B, Ferrão C, Spranger MI (2003) Effect of wine style and winemaking technology on resveratrol levels in wines. Ciencia e Tecnica Vitivinicola 18(2):77–91Google Scholar
  35. Sun B, Ribes AM, Leandro MC, Belchior AP, Spranger MI (2006) Stilbenes: quantitative extraction from grape skins, contribution of grape solids to wine and variation during wine maturation. Anal Chim Acta 563(1):382–390CrossRefGoogle Scholar
  36. Tarola A, Milano F, Giannetti V (2007) Simultaneous determination of phenolic compounds in red wines by HPLC-UV. Anal Lett 40(12):2433–2445CrossRefGoogle Scholar
  37. Tříska J, Vrchotová N, Balík J, Soural I, Sotolář R (2017) Variability in the content of trans-resveratrol, trans-ε-Viniferin and R2-Viniferin in grape cane of seven Vitis vinifera L. varieties during a three-year study. Molecules 22(6):928–938CrossRefGoogle Scholar
  38. Vian MA, Tomao V, Gallet S, Coulomb P, Lacombe J (2005) Simple and rapid method for cis-and trans-resveratrol and piceid isomers determination in wine by high-performance liquid chromatography using Chromolith columns. J Chromatogr A 1085(2):224–229CrossRefGoogle Scholar
  39. Vinas P, Campillo N, Martínez-Castillo N, Hernández-Córdoba M (2009) Solid-phase microextraction on-fiber derivatization for the analysis of some polyphenols in wine and grapes using gas chromatography–mass spectrometry. J Chromatogr A 1216(9):1279–1284CrossRefGoogle Scholar
  40. Vlase L, Kiss B, Leucuta SE, Gocan S (2009) A rapid method for determination of resveratrol in wines by HPLC-MS. J Liq Chromatogr Relat Technol 32(14):2105–2121CrossRefGoogle Scholar
  41. Zhu Y, Coury L, Long H, Duda C, Kissinger CB, Kissinger PT (2000) Liquid chromatography with multi-channel electrochemical detection for the determination of resveratrol in wine, grape juice, and grape seed capsules with automated solid phase extraction 23(10):1555–1564Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.LAQV, REQUIMTE, Laboratory of Applied Chemistry, Department of Chemical Sciences, Faculty of PharmacyUniversity of PortoPortoPortugal
  2. 2.UCIBIO, REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of PharmacyUniversity of PortoPortoPortugal

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