Journal of the American Oil Chemists' Society

, Volume 90, Issue 2, pp 225–232 | Cite as

Comparison of Antioxidant Capacities of Rosmarinate Alkyl Esters in Riboflavin Photosensitized Oil-in-Water Emulsions

  • Jae Hwan Lee
  • Atikorn Panya
  • Mickaël Laguerre
  • Christelle Bayrasy
  • Jérôme Lecomte
  • Pierre Villeneuve
  • Eric A. Decker
Original Paper

Abstract

Effects of the alkyl chain length of rosmarinate alkyl esters on the oxidative stability in photosensitized oil-in-water (O/W) emulsions were determined by lipid hydroperoxides and headspace volatile analyses. Antioxidant capacities of 20 μM rosmarinate esters with alkyl chain length of 0, 4, 8, 12, 18, and 20 were tested in O/W emulsion containing stripped soybean oil, Tween 20 as an emulsifier, and riboflavin as a photosensitizer. Synergistic or antagonistic effects of 20 μM α-tocopherol in the presence of rosmarinate alkyl esters were also determined. Samples containing rosmarinate with 4 and 8 alkyl esters showed lower lipid hydroperoxides and headspace volatiles than those without rosmarinate and those with 0, 12, 18, and 20 alkyl esters, which indicates that phenolic free radical scavengers showed antioxidant capacities non-linearly in riboflavin photosensitized O/W emulsions. Antagonistic rather than synergistic effects were observed in all rosmarinate alkyl esters with α-tocopherol in current conditions although rosmarinates with 4, 8, and 12 alkyl esters showed better antioxidant capacities than those with other alkyl chain length. The results of this study clearly showed that rosmarinates need the proper length of non-polar groups to show optimum antioxidant capacities in O/W emulsions with Tween 20 as an emulsifier under riboflavin photosensitization.

Keywords

Rosmarinate alkyl esters Riboflavin photosensitization Oil-in-water emulsions Oxidative stability Antioxidant capacity 

References

  1. 1.
    McClements DJ, Decker EA (2000) Lipid oxidation in oil-in-water emulsions: impact of molecular environment on chemical reactions in heterogeneous food systems. J Food Sci 65:1270–1282CrossRefGoogle Scholar
  2. 2.
    Chaiyasit W, Elias RJ, McClements DJ, Decker EA (2007) Role of physical structures in bulk oils on lipid oxidation. Crit Rev Food Sci Nutr 47:299–317CrossRefGoogle Scholar
  3. 3.
    Schwarz K, Huang SW, German JB, Tiersch B, Hartmann J, Frankel EN (2000) Activities of antioxidants are affected by colloidal properties of oil-in-water and water-in-oil emulsions and bulk oils. J Agric Food Chem 48:4874–4882CrossRefGoogle Scholar
  4. 4.
    Mei LY, Decker EA, McClements DJ (1998) Evidence of iron association with emulsion droplets and its impact on lipid oxidation. J Agric Food Chem 46:5072–5077CrossRefGoogle Scholar
  5. 5.
    Hu M, McClements DJ, Decker EA (2003) Lipid Oxidation in corn oil-in-water emulsions stabilized by casein, whey protein isolate, and soy protein isolate. J Agric Food Chem 51:1696–1700CrossRefGoogle Scholar
  6. 6.
    Chaiyasit W, McClements DJ, Decker EA (2005) The relationship between the physicochemical properties of antioxidants and their ability to inhibit lipid oxidation in bulk oil and oil-in-water emulsions. J Agric Food Chem 53:4982–4988CrossRefGoogle Scholar
  7. 7.
    Shahidi F, Zhong Y (2011) Revisiting the polar paradox theory: a critical overview. J Agric Food Chem 59:3499–3504CrossRefGoogle Scholar
  8. 8.
    Porter WL, Black ED, Drolet AM (1989) Use of polyamide oxidative fluorescence test on lipid emulsions: contrast in relative effectiveness of antioxidants in bulk versus dispersed systems. J Agric Food Chem 37:615–624CrossRefGoogle Scholar
  9. 9.
    Frankel EN, Huang SW, Kanner J, German JB (1994) Interfacial phenomena in the evaluation of antioxidants: bulk oils vs emulsion. J Agric Food Chem 42:1054–1059CrossRefGoogle Scholar
  10. 10.
    Medina I, Lois S, Alcántara D, Lucas R, Morales JC (2009) Effect of lipophilization of hydroxytyrosol on its antioxidant activity in fish oils and fish oil-in-water emulsions. J Agric Food Chem 57:9773–9779CrossRefGoogle Scholar
  11. 11.
    Panya A, Laguerre M, Bayrasy C, Lecomte J, Villeneuve P, McClements DJ, Decker EA (2012) An investigation of the versatile antioxidant mechanism of action of rosmarinate alkyl esters in oil-in-water emulsions. J Agric Food Chem 60:2692–2700CrossRefGoogle Scholar
  12. 12.
    Panya A, Laguerre M, Lecomte J, Villeneuve P, Weiss J, McClements DJ, Decker EA (2010) Effects of chitosan and rosmarinate esters on the physical and oxidative stability of liposomes. J Agric Food Chem 58:5679–5684CrossRefGoogle Scholar
  13. 13.
    An CB, Li D, Liang R, Bu YZ, Wang S, Zhang EH, Wang P, Ai XC, Zhang JP, Skibsted LH (2011) Chain length effects in isoflavonoid daidzein alkoxy derivatives as antioxidants: a quantum mechanical approach. J Agric Food Chem 59:12652–12657CrossRefGoogle Scholar
  14. 14.
    Tofani D, Balducci V, Gasperi T, Incerpi S, Gambacorta A (2010) Fatty acid hydroxytyrosyl esters: structure/antioxidant activity relationship by ABTS and in cell-culture DCF assays. J Agric Food Chem 58:5292–5299CrossRefGoogle Scholar
  15. 15.
    Laguerre M, Wrutniak-Cabello C, Chabi B, López Giraldo LJ, Lecomte J, Villeneuve P, Cabello G (2011) Does hydrophobicity always enhance antioxidant drugs? A cut-off effect of the chain length of functionalized chlorogenate esters on ROS-overexpressing fibroblasts. J Pharm Pharmacol 63:531–540CrossRefGoogle Scholar
  16. 16.
    Lucas R, Comelles F, Maldonado OS, Curcuroze M, Parra JL, Morales JC (2010) Surface-active properties of lipophilic antioxidants tyrosol and hydroxytyrosol fatty acid esters: a potential explanation for the nonlinear hypothesis of the antioxidant activity in oil-in-water emulsions. J Agric Food Chem 58:8021–8026CrossRefGoogle Scholar
  17. 17.
    Laguerre M, Lopez Giraldo LJ, Lecomte J, Figueroa-Espinoza MC, Barea B, Weiss J, Decker EA, Villeneuve P (2009) Chain length affects antioxidant properties of chlorogenate esters in emulsion: the cutoff theory behind the polar paradox. J Agric Food Chem 57:11335–11342CrossRefGoogle Scholar
  18. 18.
    Laguerre M, Lopez Giraldo LJ, Lecomte J, Figueroa-Espinoza MC, Barea B, Weiss J, Decker EA, Villeneuve P (2010) Relationship between hydrophobicity and antioxidant ability of “Phenolipids” in emulsion: a parabolic effect of the chain length of rosmarinate esters. J Agric Food Chem 58:2869–2876CrossRefGoogle Scholar
  19. 19.
    Sørensen ADM, Nielsen NS, Yang Z, Xu X, Jacobsen C (2012) Lipophilization of dihydrocaffeic acid affects its antioxidative properties in fish-oil-enriched emulsion. Eur J Lipid Sci Technol 114:134–145CrossRefGoogle Scholar
  20. 20.
    Boff JM, Min DB (2002) Chemistry and reaction of singlet oxygen in foods. Compr Rev Food Sci F 1:58–72CrossRefGoogle Scholar
  21. 21.
    Foote CS (1976) Photosensitized oxidation and singlet oxygen. Consequences in biological systems. In: Pryor WA (ed) Free radicals in biology vol. 2. Academic Press, New York, pp 85–133Google Scholar
  22. 22.
    Lee JH, Min DB (2010) Analysis of volatile compounds from chlorophyll photosensitized linoleic acid by headspace solid phase microextraction (HS-SPME). Food Sci Biotechnol 19:611–616CrossRefGoogle Scholar
  23. 23.
    Lee JH, Decker EA (2011) Effects of metal chelator, sodium azide, and superoxide anion dismutase (SOD) on the oxidative stability in riboflavin photosensitized O/W emulsion systems. J Agric Food Chem 59:6271–6276CrossRefGoogle Scholar
  24. 24.
    Lecomte J, Giraldo LJL, Laguerre M, Baréa B, Villeneuve P (2010) Synthesis, characterization and free radical scavenging properties of rosmarinic acid fatty esters. J Am Oil Chem Soc 87:615–620CrossRefGoogle Scholar
  25. 25.
    Waraho T, Cardenia V, Rodriguez-Estrada MT, McClements DJ, Decker EA (2009) Prooxidant mechanisms of free fatty acids in stripped soybean oil-in-water emulsions. J Agric Food Chem 57:7112–7117CrossRefGoogle Scholar
  26. 26.
    Shi J, Qu Q, Kakuda Y, Xue SJ, Jiang Y, Koide S, Shim YY (2007) Investigation of the antioxidant and synergistic activity of lycopene and other natural antioxidants using LAME and AMVN model systems. J Food Compos Anal 20:603–608CrossRefGoogle Scholar
  27. 27.
    Waraho T, McClements DJ, Decker EA (2011) Mechanisms of lipid oxidation in food dispersions. Trends Food Sci Tech 22:3–13CrossRefGoogle Scholar
  28. 28.
    Stöckmann H, Schwarz K, Huynh-Ba T (2000) The influence of various emulsifiers on the partitioning and antioxidant activity of hydroxybenzoic acids and their derivatives in oil-in-water emulsions. J Am Oil Chem Soc 77:535–542CrossRefGoogle Scholar
  29. 29.
    Alamed J, Chaiyasit W, McClements DJ, Decker EA (2009) Relationships between free radical scavenging and antioxidant activity in foods. J Agric Food Chem 57:2969–2976CrossRefGoogle Scholar
  30. 30.
    Sim WLS, Han MY, Huang D (2009) Quantification of antioxidant capacity in a microemulsion system: synergistic effects of chlorogenic acid with α-tocopherol. J Agric Food Chem 57:3409–3414CrossRefGoogle Scholar

Copyright information

© AOCS 2012

Authors and Affiliations

  • Jae Hwan Lee
    • 1
  • Atikorn Panya
    • 3
  • Mickaël Laguerre
    • 2
  • Christelle Bayrasy
    • 2
  • Jérôme Lecomte
    • 2
  • Pierre Villeneuve
    • 2
  • Eric A. Decker
    • 3
  1. 1.Department of Food Science and BiotechnologySungkyunkwan UniversitySuwonKorea
  2. 2.CIRAD, UMR IATEMontpellierFrance
  3. 3.Department of Food ScienceUniversity of MassachusettsAmherstUSA

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