Advertisement

Adsorption

pp 1–9 | Cite as

Concentration of resveratrol at the oil–water interface of corn oil-in-water emulsions

  • Jolanta Narkiewicz-Michalek
  • Marta Szymula
  • Sonia Losada-Barreiro
  • Carlos Bravo-DiazEmail author
Article
  • 8 Downloads

Abstract

Accumulation of polyphenolic antioxidants at the oil–water interfaces of lipid-based emulsions is crucial to improve their oxidative stability. Polyphenolic antioxidants are added to lipid-based emulsions to minimize the lipid peroxidation reaction, a radical reaction that produces harmful products and undesirable off-flavors, and because of their benefits in human health. Antioxidants react with the lipid radicals at the oil–water interface of emulsions, inhibiting or minimizing the lipid oxidation reaction, increasing the oxidative stability of the emulsion, and their efficiency in inhibiting the oxidation of lipids strongly depends on their interfacial concentration. In this work we have evaluated the accumulation of trans-resveratrol (3,4′,5-trihydroxystilbene, TRES) in the interfacial region of a model food-grade emulsion composed of stripped corn oil, acidic water and Tween 20 and analyzed its variation with the surfactant concentration. Results show that TRES distributes between the three regions, but more than 85% of TRES is located in the interfacial region and only a small fraction in the oil and aqueous regions. An increase in emulsifier concentration promotes the incorporation of TRES into the interfacial region, however, its interfacial concentration, which is much higher than the stoichiometric concentration, decrease because of the increase of the interfacial volume. Results obtained should contribute to a better understanding of the antioxidant efficiency in inhibiting lipid oxidation and to the development of new strategies to prepare healthier and more nutritional foods with longer shelf-lives.

Keywords

Emulsions Antioxidants Interfacial concentration 

Notes

Acknowledgements

S. L‐B thanks Xunta de Galicia for a postdoctoral Grant (POS‐B/2016/012). Financial support of the following institutions is also acknowledged: Red de Uso Sostenible de los Recursos Naturales y Agroalimentarios (REDUSO, Xunta de Galicia, Grant number ED431D 2017/18), FEDER (COMPETE) and University of Vigo.

References

  1. Aliaga, C., Bravo-Moraga, F., Danilo, G., Márquez, S., Lürh, S., Mena, G., Rezende, M.C.: Location of TEMPO derivatives in micelles: subtle effect of the probe orientation. Food Chem. 192, 395–401 (2016)CrossRefGoogle Scholar
  2. Almeida, J., Losada-Barreiro, S., Costa, M., Paiva-Martins, F., Bravo-Díaz, C., Romsted, L.S.: Interfacial concentrations of hydroxytyrosol and its lipophilic esters in intact olive oil-in-water emulsions: effects of antioxidant hydrophobicity, surfactant concentration, and the oil-to-water ratio on the oxidative stability of the emulsions. J. Agric. Food Chem. 64, 5274–5283 (2016)CrossRefGoogle Scholar
  3. Amri, A., Chaumeil, J.C., Sfar, S., Charrueau, C.: Administration of resveratrol: what formulation solutions to bioavailability limitations? J. Control Release 158, 182–193 (2012)CrossRefGoogle Scholar
  4. Bravo-Díaz, C., et al.: To model chemical reactivity in heterogeneous emulsions, think homogeneous microemulsions. Langmuir 31, 8961–8979 (2015)CrossRefGoogle Scholar
  5. Bravo Díaz, C.: Diazohydroxides, diazoethers and related species. In: Rappoport, Z., Liebman, J.F. (eds.) Patai’s Chemistry of Functional Groups: The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, vol. 2, p. 853. Wiley, Chichester (2011)Google Scholar
  6. Costa, M., Losada-Barreiro, S., Paiva-Martins, F., Bravo-Diaz, C.: Optimizing the efficiency of antioxidants in emulsions by lipophilization: tuning interfacial concentrations. RSC Adv. 6, 91483–91493 (2016).  https://doi.org/10.1039/C6RA18282H CrossRefGoogle Scholar
  7. Costa, M., Losada-Barreiro, S., Paiva-Martins, F., Bravo-Díaz, C.: Effects of acidity, temperature and emulsifier concentration on the distribution of caffeic acid in stripped corn and olive oil-in-water emulsions. J. Am. Oil Chem. Soc. 90, 1629–1636 (2013)CrossRefGoogle Scholar
  8. Costa, M., Losada-Barreiro, S., Paiva-Martins, F., Bravo-Díaz, C.: Physical evidence that the variations in the efficiency of homologous series of antioxidants in emulsions are a result of differences in their distribution. J. Sci. Food Agric. 97, 564–571 (2017).  https://doi.org/10.1002/jsfa.7765 CrossRefGoogle Scholar
  9. Costa, M., Losada-Barreiro, S., Paiva-Martins, F., Bravo-Díaz, C., Romsted, L.S.: A direct correlation between the antioxidant efficiencies of caffeic acid and its alkyl esters and their concentrations in the interfacial region of olive oil emulsions. The pseudophase model interpretation of the ‘‘cut-off’’ effect. Food Chem. 175, 233–242 (2015)CrossRefGoogle Scholar
  10. Delmas, D.: Resveratrol: Sources. Nova Science Publisher’s, Production and Health Benefits (2012)Google Scholar
  11. Frankel, E.N.: Lipid Oxidation. The Oily Press, PJ Barnes & Associates, Bridgwater (2005)CrossRefGoogle Scholar
  12. Freiría-Gándara, J., Losada-Barreiro, S., Paiva-Martins, F., Bravo-Díaz, C.: Differential partitioning of bioantioxidants in edible oil-water and octanol-water systems: linear free energy relationships. J. Chem. Eng. Data 63, 2999–3007 (2018).  https://doi.org/10.1021/acs.jced.8b00258 CrossRefGoogle Scholar
  13. Galan, A., Losada-Barreiro, S., Bravo-Díaz, C.: A physicochemical study of the effects of acidity on the distribution and antioxidant efficiency of trolox in olive oil-in-water emulsions. ChemPhysChem 17, 296–304 (2016)CrossRefGoogle Scholar
  14. Garcia-Meijide, M.C., Bravo-Diaz, C., Romsted, L.S.: A novel method for monitoring dediazoniations: simultaneous monitoring of rates and product distributions of 4-methylbenzenediazonium tetrafluoroborate. Int. J. Chem. Kinet. 30, 31–39 (1998)CrossRefGoogle Scholar
  15. Gunaseelan, K., Romsted, L.S., Pastoriza-Gallego, M.J., González-Romero, E., Bravo-Díaz, C.: Determining α-tocopherol distributions betweeen the oil, water and interfacial regions of macroemulsions: novel applications of electrocanalytical chemistry and a pseudophase kinetic model. Adv. Colloid Interface Sci. 123–126, 303–311 (2006)CrossRefGoogle Scholar
  16. Keiper, J., Romsted, L.S., Yao, J., Soldi, V.: Interfacial compositions of cationic and mixed non-ionic micelles by chemical trapping: a new method for characterizing the properties of amphiphilic aggregates. Colloids Surf. A 176, 53 (2001)CrossRefGoogle Scholar
  17. Lawrence, M.J.: Surfactant systems: their use in drug delivery. Chem. Soc. Rev. 23, 417–424 (1994)CrossRefGoogle Scholar
  18. Lin, C.-H., Chen, C.-H., Lin, Z.-C., Fang, J.-Y.: Recent advances in oral delivery of drugs and bioactive natural products using solid lipid nanoparticles as the carriers. J. Food Drug Anal. 25, 219–234 (2017).  https://doi.org/10.1016/j.jfda.2017.02.001 CrossRefGoogle Scholar
  19. Losada-Barreiro, S., Bravo-Díaz, C.: Free radicals and polyphenols: the redox chemistry of neurodegenerative diseases. Eur. J. Med. Chem. 133, 379–402 (2017)CrossRefGoogle Scholar
  20. Losada-Barreiro, S., Bravo Díaz, C., Paiva Martins, F., Romsted, L.S.: Maxima in antioxidant distributions and efficiencies with increasing hydrophobicity of gallic acid and its alkyl esters. The pseudophase model interpretation of the “cut-off effect. J. Agric. Food Chem. 61, 6533–6543 (2013)CrossRefGoogle Scholar
  21. Losada-Barreiro, S., Costa, M., Bravo-Díaz, C., Paiva-Martins, F.: Distribution and antioxidant efficiency of resveratrol in stripped corn oil emulsions. Antioxidants 3, 212–228 (2014a)CrossRefGoogle Scholar
  22. Losada-Barreiro, S., Costa, M., Bravo-Díaz, C., Paiva-Martins, F.: Distribution and antioxidant efficiency of resveratrol in stripped corn oil emulsions. Antioxidants 3, 212 (2014b)CrossRefGoogle Scholar
  23. Losada-Barreiro, S., Sánchez-Paz, V., Bravo-Díaz, C.: Transfer of antioxidants at the interfaces of model food emulsions: distributions and thermodynamic parameters. Org. Biomol. Chem. 2008(6), 4004–4011 (2015)Google Scholar
  24. Martinez-Aranda, N., Losada-Barreiro, N., Bravo-Díaz, C., Romsted, L.S.: Influence of temperature on the distribution of catechin in corn oil-in-water emulsions and some relevant thermodynamic parameters. Food Biophys. (2014).  https://doi.org/10.1007/s11483-11014-19332-11489 Google Scholar
  25. McClements, D.J.: Food Emulsions. CRC Press, Boca Raton, FL (2005)Google Scholar
  26. McClements, D.J.: Enhanced delivery of lipophilic bioactives using emulsions: a review of major factors affecting vitamin, nutraceutical, and lipid bioaccessibility. Food Function 9, 22–41 (2018).  https://doi.org/10.1039/C7FO01515A CrossRefGoogle Scholar
  27. McClements, D.J., Decker, E.A., Weiss, J.: Emulsion-based delivery systems for lipophilic bioactive components. J. Food Sci. 72, R109–R124 (2007).  https://doi.org/10.1111/j.1750-3841.2007.00507.x CrossRefGoogle Scholar
  28. Pastoriza-Gallego, M.J., Sánchez-Paz, V., Losada-Barreiro, S., Bravo-Diaz, C., Gunaseelan, K., Romsted, L.S.: Effects of temperature and emulsifier concentration on α-tocopherol distribution in a stirred, fluid, emulsion, thermodynamics of α-tocopherol transfer between the oil and interfacial regions. Langmuir 25, 2646–2653 (2009)CrossRefGoogle Scholar
  29. Romsted, L.S., Bravo-Díaz, C.: Modelling chemical reactivity in emulsions. Curr. Opin. Colloid Interface Sci. 18, 3–14 (2013)CrossRefGoogle Scholar
  30. Sánchez-Paz, V., Pastoriza-Gallego, M.J., Losada-Barreiro, S., Bravo-Diaz, C., Gunaseelan, K., Romsted, L.S.: Quantitative determination of α-tocopherol distribution in a tributyrin/Brij 30/water model food emulsion. J. Colloid Interface Sci. 320, 1–8 (2008)CrossRefGoogle Scholar
  31. Shahidi, F.: Handbook of Antioxidants for Food Preservation, 1st edn. Woodhead Pub, Cambridge (2015)Google Scholar
  32. Silva, R., Losada-Barreiro, S., Paiva-Martins, F., Bravo-Díaz, C.: Partitioning and antioxidative effect of protocatechuates in soybean oil emulsions: relevance of emulsifier concentration. Eur. J. Lipid Sci. Technol. 119, 1600274 (2017).  https://doi.org/10.1002/ejlt.201600274 CrossRefGoogle Scholar
  33. Sjöblom, J.: Emulsions and Emulsion Stability. Taylor & Francis, Boca Raton, FL (2006)Google Scholar
  34. Thadros, T.: Emulsion Science and Technology. Wiley-VCH Verlag GmbH & Co., Weinheim (2009)CrossRefGoogle Scholar
  35. Wang, J., Shi, A., Agyei, D., Wang, Q.: Formulation of water-in-oil-in-water (W/O/W) emulsions containing trans-resveratrol. RSC Advances 7, 35917–35927 (2017).  https://doi.org/10.1039/C7RA05945K CrossRefGoogle Scholar
  36. Wu, J.M., Hsieh, T.C.: Resveratrol: State-Of-The-Art Science and Health Applications: Actionable Targets and Mechanisms of Resveratrol. World Scientific Publishing Company Pte Limited, Singapore (2019)Google Scholar
  37. Yao, J., Romsted, L.S.: Arenediazonium salts: new probes of the compositions of association colloids. 7. Average hydration numbers and Cl concentrations in the surfactant film of nonionic C12E5/Octane/water macroemulsions: temperature and NaCl concentration effects. Langmuir 16, 8771–8779 (2000)CrossRefGoogle Scholar

Copyright information

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

Authors and Affiliations

  1. 1.Faculty of ChemistryMaria Curie-Sklodowska UniversityLublinPoland
  2. 2.Departmento de Química-FísicaUniversidad de VigoVigoSpain

Personalised recommendations