Abstract
Association colloids formed by surface active minor components play an important role in the oxidative stability of bulk oils. To imitate the formation of nanostructures in refined oils, multiple surface active minor components including phospholipids, free fatty acids, diacylglycerols and sterols were added to stripped corn oil. The critical micelle concentration (CMC) of the mixed components was determined. The impact of mixed minor components at below and above their CMC on oxidative stability of bulk oil and on antioxidant activity of α-tocopherol and Trolox was investigated. The CMC of the mixed surface active components in bulk oil was 20 µmol/kg oil in the presence of 383 ± 2 ppm of water. 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) played an important role on the formation of association colloids since it was the most important component in forming the association colloids as confirmed by CMC and fluorescence probe studies. The association colloids formed by the mixed components showed prooxidative activity in bulk oil as determined by monitoring the formation of lipid hydroperoxide and hexanal. The activity of α-tocopherol or Trolox was not changed by mixed components association colloids. These results suggest that association colloids both physically and chemically impacted the oxidative stability and activity of antioxidants in bulk oil.
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Chaiyasit W, Elias RJ, McClements DJ, Decker EA (2007) Role of physical structures in bulk oils on lipid oxidation. Crit Rev Food Sci Nutr 47:299–317
Chen BC, McClements DJ, Decker EA (2011) Minor components in food oils: a critical review of their roles on lipid oxidation chemistry in bulk oils and emulsions. Crit Rev Food Sci Nutr 51:901–916
Shrestha LK, Shrestha RG, Aramaki K (2009) Self-assembled structures of diglycerol monolaurate- and monomyristate in olive oil. J Disper Sci Technol 30:1525–1532
Chen BC, Han A, McClements DJ, Decker EA (2010) Physical structures in soybean oil and their impact on lipid oxidation. J Agric Food Chem 58:11993–11999
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 44:131–135
Frankel EN, Huang S-W, Prior E, Aeschbach R (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 72:201–208
Frankel EN, Huang S-W, Kanner J, German JB (1994) Interfacial phenomena in the evaluation of antioxidants: bulk oils vs emulsions. J Agric Food Chem 42:1054–1059
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 37:615–624
Chen BC, Han A, Laguerre M, McClements DJ, Decker EA (2011) Role of reverse micelles on lipid oxidation in bulk oils: impact of phospholipids on antioxidant activity of alpha-tocopherol and Trolox. Food Funct 2:302–309
Shrestha LK, Dulle M, Glatter O, Aramaki K (2010) Structure of polyglycerol oleic acid ester nonionic surfactant reverse micelles in decane: growth control by headgroup size. Langmuir 26:7015–7024
Seddon JM (1990) Structure of the inverted hexagonal (HII) phase, and non-lamellar phase-transitions of lipids. Biochim Biophys Acta 1031:1–69
Waraho T, McClements DJ, Decker EA (2011) Mechanisms of lipid oxidation in food dispersions. Trends Food Sci Technol 22:3–13
Chen B, McClements DJ, Decker EA (2014) Impact of diacylglycerol and monoacylglycerol on the physical and chemical properties of stripped soybean oil. Food Chem 142:365–372
Boon CS, Xu Z, Yue X, McClements DJ, Weiss J, Decker EA (2008) Factors affecting lycopene oxidation in oil-in-water emulsions. J Agric Food Chem 56:1408–1414
Song B, Springer J (1996) Determination of interfacial tension from the profile of a pendant drop using computer-aided image processing: 1. Theoretical. J Colloid Interf Sci 184:64–76
Kanamoto R, Wada Y, Miyajima G, Kito M (1981) Phospholipid-phospholipid interaction in soybean oil. J Am Oil Chem Soc 58:1050–1053
Harrabi S, Herchi W, Kallel H, Mayer PM, Boukhchina S (2009) Liquid chromatographic–mass spectrometric analysis of glycerophospholipids in corn oil. Food Chem 114:712–716
Laguerre M, Chen BC, Lecomte J, Villeneuve P, McClements DJ, Decker EA (2011) Antioxidant properties of chlorogenic acid and its alkyl esters in stripped corn oil in combination with phospholipids and/or water. J Agric Food Chem 59:10361–10366
Chattopadhyay A, Mukherjee S, Raghuraman H (2002) Reverse micellar organization and dynamics: a wavelength-selective fluorescence approach. J Phys Chem B 106:13002–13009
Shantha NC, Decker EA (1994) Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids. J AOAC Int 77:421–424
Ferrari RA, Schulte E, Esteves W, Brühl L, Mukherjee KD (1996) Minor constituents of vegetable oils during industrial processing. J Am Oil Chem Soc 91:453–462
Ferrari RA, Schulte E, Esteves W, Brühl L, Mukherjee KD (1996) Minor constituents of vegetable oils during industrial processing. J Am Oil Chem Soc 73:587–592
Ghazani SM, Garcia-Llatas G, Marangoni AG (2013) Minor constituents in canola oil processed by traditional and minimal refining methods. J Am Oil Chem Soc 90:743–756
Rosen MJ, Kunjappu JT (2012) Surfactants and interfacial phenomena, 4th edn. John Wiley & Sons, Hoboken
Kalogianni EP, Karapantsios TD, Miller R (2011) Effect of repeated frying on the viscosity, density and dynamic interfacial tension of palm and olive oil. J Food Eng 105:169–179
Gil B, Handel AP (1995) The effect of surfactants on the interfacial tension of frying fat. J Am Oil Chem Soc 72:951–955
Reis P, Miller R, Leser M, Watzke H, Fainerman VB, Holmberg K (2008) Adsorption of polar lipids at the water-oil interface. Langmuir 24:5781–5786
Cercaci L, Rodriguez-Estrada MT, Lercker G, Decker EA (2007) Phytosterol oxidation in oil-in-water emulsions and bulk oil. Food Chem 102:161–167
McClements DJ (2004) Food emulsions: Principles, practices and techniques, 2nd edn. CRC Press, Boca Raton
Casimir C, Akoh DBM (2008) Food lipids: chemistry, nutrition, and biotechnology. CRC Press, Boca Raton
Manjula S, Kobayashi I, Subramanian R (2011) Characterization of phospholipid reverse micelles in nonaqueous systems in relation to their rejection during membrane processing. Food Res Int 44:925–930
Haldar S, Chattopadhyay A (2013) Application of NBD-labeled lipids in membrane and cell biology. In: Mély Y, Duportail G (eds) Fluorescent methods to study biological membranes. Springer, Berlin Heidelberg, pp 37–50
Fery-Forgues S, Fayet J-P, Lopez A (1993) Drastic changes in the fluorescence properties of NBD probes with the polarity of the medium: involvement of a TICT state? J Photochem Photobiol A: Chem 70:229–243
Mukherjee S, Raghuraman H, Dasgupta S, Chattopadhyay A (2004) Organization and dynamics of N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)-labeled lipids: a fluorescence approach. Chem Phys Lipids 127:91–101
Holvoet P, Perez G, Zhao Z, Brouwers E, Bernar H, Collen D (1995) Malondialdehyde-modified low-density lipoproteins in patients with atherosclerotic disease. J Clin Invest 95:2611–2619
Wood L, Fitzgerald D, Gibson P, Cooper D, Garg M (2000) Lipid peroxidation as determined by plasma isoprostanes is related to disease severity in mild asthma. Lipids 35:967–974
Cohn JS (2002) Oxidized fat in the diet, postprandial lipaemia and cardiovascular disease. Curr Opin Lipidol 13:19–24
Bartsch H, Nair J (2004) Oxidative stress and lipid peroxidation-derived DNA-lesions in inflammation driven carcinogenesis. Cancer Detect Prev 28:385–391
Kittipongpittaya K, Panya A, McClements D, Decker E (2014) Impact of free fatty acids and phospholipids on reverse micelles formation and lipid oxidation in bulk oil. J Am Oil Chem Soc 91:453–462
Chen BC, Panya A, McClements DJ, Decker EA (2012) New insights into the role of iron in the promotion of lipid oxidation in bulk oils containing reverse micelles. J Agric Food Chem 60:3524–3532
Huang S-W, Frankel EN, Aeschbach R, German JB (1997) Partition of selected antioxidants in corn oil − water model systems. J Agric Food Chem 45:1991–1994
Huang S-W, Hopia A, Schwarz K, Frankel EN, German JB (1996) Antioxidant activity of α-tocopherol and trolox in different lipid substrates: bulk oils vs oil-in-water emulsions. J Agric Food Chem 44:444–452
Koga T, Terao J (1994) Antioxidant activity of a novel phosphatidyl derivative of vitamin E in lard and its model system. J Agric Food Chem 42:1291–1294
King MF, Boyd LC, Sheldon BW (1992) Effects of phospholipids on lipid oxidation of a salmon oil model system. J Am Oil Chem Soc 69:237–242
King MF, Boyd LC, Sheldon BW (1992) Antioxidant properties of individual phospholipids in a salmon oil model system. J Am Oil Chem Soc 69:545–551
Miyashita K, Takagi T (1986) Study on the oxidative rate and prooxidant activity of free fatty acids. J Am Oil Chem Soc 63:1380–1384
Frega N, Mozzon M, Lercker G (1999) Effects of free fatty acids on oxidative stability of vegetable oil. J Am Oil Chem Soc 76:325–329
Mistry BS, Min DB (1987) Effects of fatty acids on the oxidative stability of soybean oil. J Food Sci 52:831–832
Mistry BS, Min DB (1988) Prooxidant effects of monoglycerides and diglycerides in soybean oil. J Food Sci 53:1896–1897
Nakatsugawa K, Ohashi K, Shimada A (2001) Comparison of oxidative stability of diacylglycerol and triacylglycerol. Nippon Shokuhin Kagaku Kaishi 48:429–436
Nyström L, Achrenius T, Lampi A-M, Moreau RA, Piironen V (2007) A comparison of the antioxidant properties of steryl ferulates with tocopherol at high temperatures. Food Chem 101:947–954
Wang T, Hicks KB, Moreau R (2002) Antioxidant activity of phytosterols, oryzanol, and other phytosterol conjugates. J Am Oil Chem Soc 79:1201–1206
Winkler JK, Warner K (2008) The effect of phytosterol concentration on oxidative stability and thermal polymerization of heated oils. Eur J Lipid Sci Technol 110:455–464
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Kittipongpittaya, K., Panya, A., Cui, L. et al. Association Colloids Formed by Multiple Surface Active Minor Components and Their Effect on Lipid Oxidation in Bulk Oil. J Am Oil Chem Soc 91, 1955–1965 (2014). https://doi.org/10.1007/s11746-014-2541-z
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DOI: https://doi.org/10.1007/s11746-014-2541-z