1932

Abstract

Docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), both abundant in fish oil, are known to have significant biochemical and physiological effects primarily linked to the improvement of human health, especially cardiovascular and brain health. However, the incorporation of fish oil into foods and beverages is often challenging, as fish oil is very easily oxidized and can cause undesirable flavors. This review discusses this rapid formation of the fishy and metallic off-flavors, focusing especially on an early stage of fish oil oxidation. Although oxidative stability and quality of commercialized fish oil have improved over the past few years, there is a still a problem with its application: Flavor deterioration can be found even at very low oxidation levels. This review also notes the effective way to inhibit the formation of the volatile compounds responsible for the flavor deterioration.

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2018-03-25
2024-12-13
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Literature Cited

  1. Aidos I, Jacobsen C, Jensen B, Luten JB, van der Padt A. et al. 2002. Volatile oxidation products formed in crude herring oil under accelerated oxidative conditions. Eur. J. Lipid Sci. Technol. 104:808–18 [Google Scholar]
  2. Allayee H, Roth N, Hodis HN. 2009. Polyunsaturated fatty acids and cardiovascular disease: implications for nutrigenetics. J. Nutrigenet. Nutrigenom. 2:140–48 [Google Scholar]
  3. Anwar SH, Kunz B. 2011. The influence of drying methods on the stabilization of fish oil microcapsules: comparison of spray granulation, spray drying, and freeze drying. J. Food Eng. 105:367–78 [Google Scholar]
  4. Backes J, Anzalone D, Hilleman D, Catini J. 2016. The clinical relevance of omega-3 fatty acids in the management of hypertriglyceridemia. Lipids Health Dis 15:118 [Google Scholar]
  5. Bandarra N, Campos R, Batista I, Nunes ML, Empis J. 1999. Antioxidant synergy of α-tocopherol and phospholipids. J. Am. Oil Chem. Soc. 76:905–13 [Google Scholar]
  6. Benjamin BA, Cameron-Smith D, Hofman PL, Cutfield WS. 2013. Oxidation of marine omega-3 supplements and human health. Biomed. Res. Int. 2013:464921 [Google Scholar]
  7. Bernardi DM, Bertol TM, Pflanzer SB, Sgarbieria VC, Pollonio MAR. 2016. ω-3 in meat products: benefits and effects on lipid oxidative stability. J. Sci. Food Agric 96:2620–34 [Google Scholar]
  8. Bersuder P, Hole M, Smith G. 2001. Antioxidants from a heated histidine-glucose model system. Investigation of the copper(II) binding ability. J. Am. Oil Chem. Soc. 78:1079–82 [Google Scholar]
  9. Bhale SD, Xu Z, Prinyawiwatkul W, King JM, Godber JS. 2007. Oregano and rosemary extracts inhibit oxidation of long-chain n-3 fatty acids in menhaden oil. J. Food Sci. 72:C504–8 [Google Scholar]
  10. Bosa DJ, van Montforta SJT, Oranjea B, Durstona S, Smeets PAS. 2016. Effects of omega-3 polyunsaturated fatty acids on human brain morphology and function: What is the evidence?. Eur. Neuropsychopharmacol 26:546–61 [Google Scholar]
  11. Boyd LC, Nwosu VC, Young CL, MacMillian L. 1998. Monitoring lipid oxidation and antioxidant effects of phospholipids by headspace gas chromatographic analyses of rancimat trapped volatiles. J. Food Lipids 5:269–82 [Google Scholar]
  12. Bylaite E, Meyer AS. 2006. Characterisation of volatile aroma compounds of orange juices by three dynamic and static headspace gas chromatography techniques. Eur. Food Res. Technol. 222:176–84 [Google Scholar]
  13. Calder PC. 2004. n-3 Fatty acids and cardiovascular disease: evidence explained and mechanisms explored. Clin. Sci. 107:1–11 [Google Scholar]
  14. Cavalli J-F, Fernandez X, Lizzani-Cuvelier L, Loiseau A-M. 2003. Comparison of static headspace, headspace solid phase microextraction, headspace sorptive extraction, and direct thermal desorption techniques on chemical composition of French olive oils. J. Agric. Food Chem. 51:7709–16 [Google Scholar]
  15. Chiesa G, Busnelli M, Manzini S, Parolini C. 2016. Nutraceuticals and bioactive components from fish for dyslipidemia and cardiovascular risk reduction. Mar. Drugs 14:113 [Google Scholar]
  16. Cho SY, Joo DS, Choi HG, Nara E, Miyashita K. 2001. Oxidative stability of lipids from squid tissues. Fish. Sci. 67:738–43 [Google Scholar]
  17. Cho S-Y, Miyashita K, Miyazawa T, Fujimoto K, Kaneda T. 1987.a Autoxidation of ethyl eicosapentaenoate and docosahexaenoate. J. Am. Oil Chem. Soc. 64:876–79 [Google Scholar]
  18. Cho S-Y, Miyashita K, Miyazawa T, Fujimoto K, Kaneda T. 1987.b Autoxidation of ethyl eicosapentaenoate and docosahexaenoate under light irradiation. Nippon Suisan Gakkaishi 53:813–17 [Google Scholar]
  19. Cosgrove JP, Church DF, Pryor WA. 1987. The kinetics of the autoxidation of polyunsaturated fatty acids. Lipids 22:299–304 [Google Scholar]
  20. Cui L, Decker EA. 2016. Phospholipids in foods: prooxidants or antioxidants?. J. Sci. Food Agric. 96:18–31 [Google Scholar]
  21. Cui L, McClements DJ, Decker EA. 2015. Impact of phosphatidylethanolamine on the antioxidant activity of α-tocopherol and trolox in bulk oil. J. Agric. Food Chem. 63:3288–94 [Google Scholar]
  22. De Backer G, Ambrosioni E, Borch-Johnsen K, Brotons C, Cifkova R. et al. 2003. European guidelines on cardiovascular disease prevention in clinical practice. Third Joint Task Force of European and Other Societies on Cardiovascular Disease Prevention in Clinical Practice. Eur. Heart. J 24:1601–10 [Google Scholar]
  23. Dehaut A, Himber C, Mulak V, Grard T, Krzewinski F. et al. 2014. Evolution of volatile compounds and biogenic amines throughout the shelf life of marinated and salted anchovies (Engraulis encrasicolus). J. Agric. Food Chem 62:8014–22 [Google Scholar]
  24. Doert M, Jaworska K, Moersel J-T, Kroh L. 2012. Synergistic effect of lecithins for tocopherols: lecithin-based regeneration of α-tocopherol. Eur. Food Res. Technol. 235:915–28 [Google Scholar]
  25. Drusch S, Serfert Y, Van Den Heuvel A, Schwarz K. 2006. Physicochemical characterization and oxidative stability of fish oil encapsulated in an amorphous matrix containing trehalose. Food Res. Int. 39:807–15 [Google Scholar]
  26. Endo Y, Hayashi C, Yamanaka T, Takayose K, Yamaoka M. et al. 2013. Linolenic acid as the main source of acrolein formed during heating of vegetable oils. J. Am. Oil Chem. Soc. 90:959–64 [Google Scholar]
  27. Erdmann ME, Zeeb B, Salminen H, Gibis M, Lautenschlaeger R, Weiss J. 2015. Influence of droplet size on the antioxidant activity of rosemary extract loaded oil-in-water emulsions in mixed systems. Food Funct. 6793–804
  28. Frankel EN. 1987. Secondary products of lipid oxidation. Chem. Phys.Lipids 44:73–85 [Google Scholar]
  29. Frankel EN. 1993. Formation of headspace volatiles by thermal decomposition of oxidized fish oils vs. oxidized vegetable oils. J. Am. Oil Chem. Soc. 70:767–72 [Google Scholar]
  30. Frankel EN. 1998. Free radical oxidation, hydroperoxide formation. In Lipid Oxidation. EN Frankel 13–41 Dundee, Scotland: Oily Press
  31. Frankel EN, Huang S-W. 1996. Evaluation of antioxidant activity of rosemary extracts, carnosol and carnosic acid in bulk vegetable oils and fish oil and their emulsions. J. Sci. Food Agric 172:201–8 [Google Scholar]
  32. Frankel EN, Huang S-W, Aeschbach R, Prior E. 1996. Antioxidant activity of a rosemary extract and its constituents, carnosic acid, carnosol, and rosmarinic acid, in bulk oil and oil-in-water emulsion. J. Agric. Food Chem. 44:131–35 [Google Scholar]
  33. Garg ML, Wood LG, Singh H, Moughan PJ. 2006. Means of delivering recommended levels of long chain n-3 polyunsaturated fatty acids in human diets. J. Food Sci. 71:R66–71 [Google Scholar]
  34. Glück T, Alter P. 2016. Marine omega-3 highly unsaturated fatty acids: from mechanisms to clinical implications in heart failure and arrhythmias. Vasc. Pharmacol 82:11–19 [Google Scholar]
  35. Gómez-Cortés P, Sacks GL, Brenna JT. 2015. Quantitative analysis of volatiles in edible oils following accelerated oxidation using broad spectrum isotope standards. Food Chem 174:310–18 [Google Scholar]
  36. Grosch W. 1987. Reactions of hydroperoxides: products of low molecular weight. In Autoxidation of Unsaturated Lipids. HWS Chan 95–139 London: Academic
  37. Gunstone FD, Hilditch TP. 1945. The union gaseous oxygen with methyl oleate, linoleate, and linolenate. J. Chem. Soc.836–41 [Google Scholar]
  38. Guth H, Grosch W. 1993. Identification of potent odourants in static headspace samples of green and black tea powders on the basis of aroma extract dilution analysis (AEDA). Flavor Fragr. J. 8:173–78 [Google Scholar]
  39. Hallahan B, Ryan T, Hibbeln JR, Murray IT, Glynn S. et al. 2016. Efficacy of omega-3 highly unsaturated fatty acids in the treatment of depression. Br. J. Psychiatry 209:192–201 [Google Scholar]
  40. Hartvigsen K, Lund P, Hansen LF, Holmer G. 2000. Dynamic headspace gas chromatography/mass spectrometry characterization of volatiles produced in fish oil–enriched mayonnaise during storage. J. Agric. Food Chem. 48:4858–67 [Google Scholar]
  41. Hidalgo FJ, León MM, Zamora R. 2006. Antioxidative activity of amino phospholipids and phospholipid/amino acid mixtures in edible oils as determined by the rancimat method. J. Agric. Food Chem. 54:5461–67 [Google Scholar]
  42. Hidalgo FJ, León MM, Zamora R. 2007. Effect of tocopherols in the antioxidative activity of oxidized lipid-amine reaction products. J. Agric. Food Chem. 55:4436–42 [Google Scholar]
  43. Hidalgo FJ, Nogales F, Zamora R. 2005. Changes produced in the antioxidative activity of phospholipids as a consequence of their oxidation. J. Agric. Food Chem. 53:659–62 [Google Scholar]
  44. Hirayama T, Yamaguchi M, Nakata T, Okumura M, Yamasaki T. et al. 1989. Formation of acrolein by the autoxidation of unsaturated fatty acid methyl esters. Eisei Kagaku 35:303–6 From Japanese [Google Scholar]
  45. Holman RT, Elmer OC. 1947. The rates of oxidation of unsaturated fatty acids and esters. J. Am. Oil Chem. Soc. 24:127–29 [Google Scholar]
  46. Horiuchi M, Umano K, Shibamoto T. 1998. Analysis of volatile compounds formed from fish oil heated with cysteine and trimethylamine oxide. J. Agric. Food Chem. 46:5232–37 [Google Scholar]
  47. Hsieh TCY, Williams SS, Vejaphan W, Meyers SP. 1989. Characterization of volatile components of menhaden fish (Brevoortia tyrannus) oil. J. Am. Oil Chem. Soc. 66:114–17 [Google Scholar]
  48. Iglesias J, Lois S, Medina I. 2007. Development of a solid-phase microextraction method for determination of volatile oxidation compounds in fish oil emulsions. J. Chromatogr. A 1163:277–87 [Google Scholar]
  49. Jacobsen C. 1999. Sensory impact of lipid oxidation in complex food systems. Eur. J. Lipid Sci. Technol. 101:484–92 [Google Scholar]
  50. Jacobsen C, Hartvigsen K, Lund P, Adler-Nissen J, Hølmer G. et al. 2000. Oxidation in fish-oil-enriched mayonnaise 2. Assessment of the efficacy of different tocopherol antioxidant systems by discriminant partial least squares regression analysis. Eur. Food Res. Technol. 210:242–57 [Google Scholar]
  51. Jacobsen C, Hartvigsen K, Lund P, Meyer AS, Adler-Nissen J. et al. 1999. Oxidation in fish-oil-enriched mayonnaise 1. Assessment of propyl gallate as an antioxidant by discriminant partial least squares regression analysis. Eur. Food Res. Technol. 210:13–30 [Google Scholar]
  52. Jacobsen C, Hartvigsen K, Lund P, Thomsen MK, Skibsted LH. et al. 2001.a Oxidation in fish oil–enriched mayonnaise: 4. Effect of tocopherol concentration on oxidative deterioration. Eur. Food Res. Technol. 212:308–18 [Google Scholar]
  53. Jacobsen C, Hartvigsen K, Thomsen MK, Hansen LF, Lund P. et al. 2001.b Lipid oxidation in fish oil enriched mayonnaise: calcium disodium ethylenediaminetetraacetate, but not gallic acid, strongly inhibited oxidative deterioration. J. Agric. Food Chem. 49:1009–19 [Google Scholar]
  54. Jacobsen C, Timm M, Meyer AS. 2001.c Oxidation in fish oil enriched mayonnaise: ascorbic acid and low pH increase oxidative deterioration. J Agric. Food Chem. 49:3947–56 [Google Scholar]
  55. Jan F, Stevens JF, Maier CS. 2008. Acrolein: sources, metabolism, and biomolecular interactions relevant to human health and disease. Mol. Nutr. Food Res. 52:7–25 [Google Scholar]
  56. Jiang J, Li K, Wang F, Yang B, Fu Y. et al. 2016. Effect of marine-derived n-3 polyunsaturated fatty acids on major eicosanoids: a systematic review and meta-analysis from 18 randomized controlled trials. PLOS ONE 11:e0147351 [Google Scholar]
  57. Karahadian C, Lindsay RC. 1989. Evaluation of compounds contributing characterizing fishy flavors in fish oils. J. Am. Oil Chem. Soc. 66:953–60 [Google Scholar]
  58. King MF, Boyd LC, Sheldon BW. 1992. Effects of phospholipids on lipid oxidation of a salmon oil model system. J. Am. Oil Chem. Soc. 69:237–42 [Google Scholar]
  59. Kris-Etherton PM, Harris WS, Appel LJ. 2002. Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation 106:2747–57 [Google Scholar]
  60. Leaf A, Kang JX, Xiao Y-F. 2008. Fish oil fatty acids as cardiovascular drugs. Curr. Vasc. Pharmacol. 6:1–12 [Google Scholar]
  61. Lee H, Kizito SA, Weese SJ, Craig-Schmidt MC, Lee Y. et al. 2003. Analysis of headspace volatile and oxidized volatile compounds in DHA-enriched fish oil on accelerated oxidative storage. J. Food Sci. 68:2169–77 [Google Scholar]
  62. Lee JH, Decker EA. 2011. Effects of metal chelator, sodium azide, and superoxide dismutase on the oxidative stability in riboflavin-photosensitized oil-in-water emulsion systems. J. Agric. Food Chem. 59:6271–76 [Google Scholar]
  63. LoPachin RM, Gavin T. 2014. Molecular mechanisms of aldehyde toxicity: a chemical perspective. Chem. Res. Toxicol. 27:1081–91 [Google Scholar]
  64. Lorenzo IM, Pavón JLP, Laespada MEF, Pinto CG, Cordero BM. 2002.a Detection of adulterants in olive oil by headspace-mass spectrometry. J. Chromatogr. A 945:221–30 [Google Scholar]
  65. Lorenzo IM, Pavón JLP, Laespada MEF, Pinto CG, Cordero BM. et al. 2002.b Application of headspace–mass spectrometry for differentiating sources of olive oil. Anal. Bioanal. Chem. 374:1205–11 [Google Scholar]
  66. Lu FSH, Nielsen NS, Baron CP, Jacobsen C. 2012. Oxidative degradation and non-enzymatic browning due to the interaction between oxidised lipids and primary amine groups in different marine PL emulsions. Food Chem 135:2887–96 [Google Scholar]
  67. Lu FSH, Nielsen NS, Timm-Heinrich M, Jacobsen C. 2011. Oxidative stability of marine phospholipids in the liposomal form and their applications. Lipids 46:3–23 [Google Scholar]
  68. Maqsood S, Benjakul S, Abushelaibi A, Alam A. 2014. Phenolic compounds and plant phenolic extracts as natural antioxidants in prevention of lipid oxidation in seafood: a detailed review. Compr. Rev. Food Sci. Food Saf. 13:1125–40 [Google Scholar]
  69. 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. 65:1270–82 [Google Scholar]
  70. Miyashita K. 2008. Oxidation of long-chain fatty acids. In Lipid Oxidation Pathways. A Kamal-Eldin, D Min 54–78 Champaign, IL: AOCS Press
  71. Miyashita K, Frankel EN, Neff WE, Awl RA. 1990. Autoxidation of polyunsaturated triacylglycerols. III. Syntheytic triacylglycerols containing linoleate and linolenate. Lipids 25:48–53 [Google Scholar]
  72. Miyashita K, Takagi T. 1986. Study on the oxidative rate and prooxidant activity of free fatty acids. J. Am. Oil Chem. Soc. 63:1380–84 [Google Scholar]
  73. Moghe A, Ghare S, Lamoreau B, Mohammad M, Barve S. et al. 2015. Molecular mechanisms of acrolein toxicity: relevance to human disease. Toxicol. Sci. 143:242–55 [Google Scholar]
  74. Morales FJ, Jimenez-Perez S. 2001. Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence. Food Chem 72:119–25 [Google Scholar]
  75. Moriya H, Kuniminato T, Hosokawa M, Fukunaga K, Nishiyama T. et al. 2007. Oxidative stability of salmon and herring roe lipids and their dietary effect on plasma cholesterol levels of rats. Fish. Sci. 73:668–74 [Google Scholar]
  76. Nordvi B, Langsrud Ø, Egelandsdal B, Slinde E, Vogt G. et al. 2007. Characterization of volatile compounds in a fermented and dried fish product during cold storage. J. Food Sci. 72:S373–80 [Google Scholar]
  77. O'Dwyer SP, O'Beirne D, Ní Eidhin D, O'Kennedy BT. 2012. Effects of green tea extract and α-tocopherol on the lipid oxidation rate of omega-3 oils, incorporated into table spreads, prepared using multiple emulsion technology. J. Food Sci. 77:N58–65 [Google Scholar]
  78. Ohshima T, Fujita Y, Koizumi C. 1993. Oxidative stability of sardine and mackerel lipids with reference to synergism between phospholipids and α-tocopherol. J. Am. Oil Chem. Soc. 170:269–76 [Google Scholar]
  79. Pegg AE. 2013. Toxicity of polyamines and their metabolic products. Chem. Res. Toxicol. 26:1782–800 [Google Scholar]
  80. Polavarapu S, Oliver CM, Ajlouni S, Augustin MA. 2011. Physicochemical characterisation and oxidative stability of fish oil and fish oil-extra virgin olive oil microencapsulated by sugar beet pectin. Food Chem 127:1694–705 [Google Scholar]
  81. Porter NA, Galdwell SE, Mills KA. 1995. Mechanisms of free radical oxidation of unsaturated lipids. Lipids 30:277–90 [Google Scholar]
  82. Pourashouri P, Shabanpour B, Abad ZNH, Zahiri S. 2016. Antioxidant effects of wild pistacia (P. atlantica), rosemary (Rosmarinus officinalis L.) and green tea extracts on the lipid oxidation rate of fish oil-in-water emulsions. Turk. J. Fish Aquat. Sci. 16:729–37 [Google Scholar]
  83. Refsgaard HHF, Brockhoff PB, Jensen B. 1998. Sensory and chemical changes in farmed Atlantic salmon (Salmo salar) during frozen storage. J. Agric. Food Chem. 46:3473–79 [Google Scholar]
  84. Refsgaard HHF, Haahr AM, Jensen B. 1999. Isolation and quantification of volatiles in fish by dynamic headspace sampling and mass spectrometry. J. Agric. Food Chem. 47:1114–18 [Google Scholar]
  85. Ritter JCS, Budge SM. 2012. Key lipid oxidation products can be used to predict sensory quality of fish oils with different levels of EPA and DHA. Lipids 47:1169–79 [Google Scholar]
  86. Russo GL. 2010. Dietary n-6 and n-3 polyunsaturated fatty acids: from biochemistry to clinical implications in cardiovascularprevention. Biochem. Pharmacol. 235:785–95 [Google Scholar]
  87. Sae-leaw T, Benjakul S. 2014. Fatty acid composition, lipid oxidation, and fishy odour development in seabass (Lates calcarifer) skin during iced storage. Eur. J. Lipid Sci. Technol. 116:885–94 [Google Scholar]
  88. Saito H, Ishihara K. 1997. Antioxidant activity and active sites of phospholipids as antixoxidants. J. Am. Oil Chem. Soc. 74:1531–36 [Google Scholar]
  89. Schaich KM. 2005. Lipid oxidation in fats and oils: theoretical aspects. Bailey's Industrial Fats and Oils F Shahidi 2681–767 New York: John Wiley. , 6th ed.. [Google Scholar]
  90. Schaich KM. 2013. Challenges in elucidating lipid oxidation mechnisms. Lipid Oxidation A Logan, U Nienaber, X Pan 1–52 Urbana, IL: AOCS Press [Google Scholar]
  91. Segawa T, Hara S, Totani Y. 1994. Antioxidative behavior of phospholipids for polyunsaturated fatty acids of fish oil. II. synergistic effect of phospholipids for tocopherol. J. Jpn. Oil Chem. Soc. 43:515–19 [Google Scholar]
  92. Segawa T, Kamata M, Hara S, Totani Y. 1995. Antioxidative behavior of phospholipids for polyunsaturated fatty acids of fish oil. III. Synergistic mechanism of nitrogen including phospholipids for tocopherol. J. Jpn. Oil Chem. Soc 44:36–42 [Google Scholar]
  93. Serfert Y, Drusch S, Schwarz K. 2010. Sensory odour profiling and lipid oxidation status of fish oil and microencapsulated fish oil. Food Chem 123:968–75 [Google Scholar]
  94. Serra A, Buccioni A, Rodriguez-Estrada MT, Conte G, Cappucci A. et al. 2014. Fatty acid composition, oxidation status and volatile organic compounds in “Colonnata” lard from Large White or Cinta Senese pigs as affected by curing time. Meat Sci 97:504–12 [Google Scholar]
  95. Sghaier L, Vial J, Sassiat P, Thiebaut D, Watiez M. et al. 2016. An overview of recent developments in volatile compounds analysis from edible oils: technique-oriented perspectives. Eur. J. Lipid Sci. Technol. 118:1853–79 [Google Scholar]
  96. Shah MA, Bosco SJD, Mir SA. 2014. Plant extracts as natural antioxidants in meat and meat products. Meat Sci 98:21–33 [Google Scholar]
  97. Shibamoto T. 2006. Analytical methods for trace levels of reactive carbonyl compounds formed in lipid peroxidation systems. J. Pharm. Biomed. Anal 41:12–25 [Google Scholar]
  98. Shibata A, Uemura M, Hosokawa M, Miyashita K. 2015. Formation of acrolein in the autoxidation of triacylglycerols with different fatty acid compositions. J. Am. Oil Chem. Soc. 92:1661–70 [Google Scholar]
  99. Shimajiri J, Shiota M, Hosokawa M, Miyashita K. 2013. Synergistic antioxidant activity of milk sphingomyeline and its sphingoid base with α-tocopherol on fish oil triacylglycerol. J. Agric. Food Chem. 61:7969–75 [Google Scholar]
  100. Singh M, Nam DT, Arseneault M, Ramassamy C. 2010. Role of by-products of lipid oxidation in Alzheimer's disease brain: a focus on acrolein. J. Alzheimer's Dis. 21:741–56 [Google Scholar]
  101. Smith SC, Allen J, Blair SN, Bonow RO, Brass LM. et al. 2006. AHA/ACC guidelines for secondary prevention for patients with coronary and other atherosclerotic vascular disease: 2006 update. Circulation 113:2363–72 [Google Scholar]
  102. Snyder JM, Frankel EN, Selke E, Warner K. 1988. Comparison of gas chromatographic methods for volatile lipid oxidation compounds in soybean oil. J. Am. Oil Chem. Soc. 65:1617–20 [Google Scholar]
  103. Song C, Shieh C-H, Wu Y-S, Kalueff A, Gaikwad S. et al. 2016. The role of omega-3 polyunsaturated fatty acids eicosapentaenoic and docosahexaenoic acids in the treatment of major depression and Alzheimer's disease: acting separately or synergistically?. Prog. Lipid Res. 62:41–54 [Google Scholar]
  104. Sørensen A-DM, Nielsen NS, Jacobsen C. 2010. Oxidative stability of fish oil–enriched mayonnaise-based salads. Eur. J. Lipid Sci. Technol. 112:476–87 [Google Scholar]
  105. Suárez-Jiménez GM, López-Saiz CM, Ramírez-Guerra HE, Ezquerra-Brauer JM, Ruiz-Cruz S. et al. 2016. Role of endogenous and exogenous tocopherols in the lipid stability of marine oil systems: a review. Int. J. Mol. Sci. 17:e1968 [Google Scholar]
  106. Sugino H, Ishikawa M, Nitoda T, Koketsu M, Juneja LR. et al. 1997. Antioxidative activity of egg yolk phospholipids. J. Agric. Food Chem. 45:551–54 [Google Scholar]
  107. Takenaka A, Hosokawa M, Miyashita K. 2007. Unsaturated phosphatidylethanolamine as effective synergist in combination with α-tocopherol. J. Oleo Sci. 56:511–16 [Google Scholar]
  108. Takeoka G, Perrino C, Buttery R. 1996. Volatile constituents of used frying oils. J. Agric. Food Chem. 44:654–60 [Google Scholar]
  109. Takeuchi M, Hara S, Totani Y, Hibino H, Tanaka Y. 1997. Antioxidative behavior of polyunsaturated phospholipids. I. Oxidative stability of marine oil containing polyunsaturated phospholipids. J. Jpn. Oil Chem. Soc. 46:175–81 [Google Scholar]
  110. Takeungwongtrakul S, Benjakul S. 2014. Oxidative stability of lipids from hepatopancreas of Pacific white shrimp (Litopenaeus vannamei) as affected by essential oils incorporation. Eur. J. Lipid Sci. Technol. 116:987–95 [Google Scholar]
  111. Taneja A, Singh H. 2012. Challenges for the delivery of long-chain n-3 fatty acids in functional foods. Annu. Rev. Food Sci. Technol. 3:105–23 [Google Scholar]
  112. Uemura M, Shibata A, Hosokawa M, Iwashima-Suzuki A, Shiota M, Miyashita K. 2016. Inhibitory effect of dihydrosphingosine with α-tocopherol on volatile formation during the autoxidation of polyunsaturated triacylglycerols. J. Oleo Sci. 65:713–22 [Google Scholar]
  113. Ueno HM, Shiota M, Ueda N, Isogai T, Kobayashi T. 2012. Iron-lactoferrin complex reduces iron-catalyzed off-flavor formation in powdered milk with added fish oil. J. Food Sci. 77:C853–58 [Google Scholar]
  114. Venkateshwarlu G, Let MB, Meyer AS, Jacobsen C. 2004.a Chemical and olfactometric characterization of volatile flavor compounds in a fish oil enriched milk emulsion. J. Agric. Food Chem. 52:311–17 [Google Scholar]
  115. Venkateshwarlu G, Let MB, Meyer AS, Jacobsen C. 2004.b Modeling the sensory impact of defined combinations of volatile lipid oxidation products on fishy and metallic off-flavors. J. Agric. Food Chem. 52:1635–41 [Google Scholar]
  116. Walker R, Deckera EA, McClements DJ. 2015. Development of food-grade nanoemulsions and emulsions for delivery of omega-3 fatty acids: opportunities and obstacles in the food industry. Food Funct 6:42–55 [Google Scholar]
  117. Wang B, Adhikari B, Barrow CJ. 2014. Optimisation of the microencapsulation of tuna oil in gelatin-sodium hexametaphosphate using complex coacervation. Food Chem 158:358–65 [Google Scholar]
  118. Wang C, Harris WS, Chung M, Lichtenstein AH, Balk EM. et al. 2006. Fatty acids from fish or fish-oil supplements, but not alpha-linolenic acid, benefit cardiovascular disease outcomes in primary- and secondary-prevention studies: a systematic review. Am. J. Clin. Nutr. 84:5–17 [Google Scholar]
  119. Wardencki W, Michulec M, Curyło J. 2004. A review of theoretical and practical aspects of solid-phase microextraction in food analysis. Int. J. Food Sci. Technol. 39:703–17 [Google Scholar]
  120. Wenzl T, Lankmayr E. 2002. Comparative studies of the static and dynamic headspace extraction of saturated short chain aldehydes from cellulose-based packaging materials. Anal. Bioanal. Chem. 372:649–53 [Google Scholar]
  121. Wijewickreme AN, Krejpcio Z, Kitts DD. 1999. Hydroxyl scavenging activity of glucose, fructose, and ribose-lysine model Maillard products. J. Food Sci. 64:457–61 [Google Scholar]
  122. Wilkes JG, Conte ED, Kim Y, Holcomb M, Sutherland JB. et al. 2000. Sample preparation for the analysis of flavors and off-flavors in foods. J. Chromatogr. A 880:3–33 [Google Scholar]
  123. Yang K-M, Cheng M-C, Chen C-W, Tseng C-Y, Lin L-Y. et al. 2017. Characterization of volatile compounds with HS-SPME from oxidized n-3 PUFA rich oils via Rancimat tests. J. Oleo Sci. 66:113–22 [Google Scholar]
  124. Yang Z-H, Emma-Okon B, Remaley AT. 2016. Dietary marine-derived long-chain monounsaturated fatty acids and cardiovascular disease risk: a mini review. Lipids Health Dis 15:201 [Google Scholar]
  125. Yilmaz Y, Toledo R. 2005. Antioxidant activity of water-soluble Maillard reaction products. Food Chem 93:273–78 [Google Scholar]
  126. Yoshimura Y, Iijima T, Watanabe T, Nakazawa H. 1997. Antioxidative effect of Maillard reaction products using glucose-glycine model system. J. Agric. Food Chem. 45:4106–9 [Google Scholar]
  127. Zamora R, Hidalgo FJ. 2005. Coordinate contribution of lipid oxidation and Maillard reaction to the nonenzymatic food browning. Crit. Rev. Food Sci. Nutr. 45:49–59 [Google Scholar]
  128. Zamora R, Nogales F, Hidalgo FJ. 2005. Phospholipid oxidation and nonenzymatic browning development in phosphatidylethanolamine/ribose/lysine model systems. Eur. Food Res. Technol. 220:459–65 [Google Scholar]
  129. Zhu Q, Liang C-P, Cheng K-W, Peng X, Lo C-Y. 2009. Trapping effects of green and black tea extracts on peroxidation-derived carbonyl substances of seal blubber oil. J. Agric. Food Chem. 57:1065–69 [Google Scholar]
/content/journals/10.1146/annurev-food-030117-012320
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  • Article Type: Review Article
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