The supramolecular chemistry of lipid oxidation and antioxidation in bulk oils

European Journal of Lipid Science and Technology - Tập 117 Số 8 - Trang 1095-1137 - 2015
Elizabeth S. Budilarto1, Afaf Kamal‐Eldin1
1Department of Food Science United Arab Emirates University Al‐Ain United Arab Emirates

Tóm tắt

The microenvironment formed by surface active compounds is being recognized as the active site of lipid oxidation. Trace amounts of water occupy the core of micro micelles and several amphiphilic minor components (e.g., phospholipids, monoacylglycerols, free fatty acids, etc.) act as surfactants and affect lipid oxidation in a complex fashion dependent on the structure and stability of the microemulsions in a continuous lipid phase such as bulk oil. The structures of the triacylglycerols and other lipid‐soluble molecules affect their organization and play important roles during the course of the oxidation reactions. Antioxidant head groups, variably located near the water‐oil colloidal interfaces, trap and scavenge radicals according to their location and concentration. According to this scenario, antioxidants inhibit lipid oxidation not only by scavenging radicals via hydrogen donation but also by physically stabilizing the micelles at the microenvironments of the reaction sites. There is a cut‐off effect (optimum value) governing the inhibitory effects of antioxidants depending inter alias on their hydrophilic/lipophilic balance and their concentrations. These complex effects, previously considered as paradoxes in antioxidants research, are now better explained by the supramolecular chemistry of lipid oxidation and antioxidants, which is discussed in this review.The evolution of micellar size and number during and after the induction period of lipid oxidation. Amphiphilic compounds, including lipid hydroperoxides, contribute to micelle formation and act as prooxidants. Antioxidants and retarders stabilize micelles and prevent their breakdown.

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Tài liệu tham khảo

10.1007/s11746-999-0105-4

10.1016/j.tifs.2007.08.001

10.1002/ejlt.201000044

Schaich K. M., 2005, Bailey's Industrial Oil and Fat Products, 269

10.1016/j.foodchem.2007.04.029

10.1111/j.1541-4337.2006.00009.x

10.1021/jf102763p

10.1080/10408398.2011.606379

10.1201/9781439822098

10.1007/s11101-009-9142-8

10.1039/jr9430000541

10.1002/1438-9312(200210)104:9/10<661::AID-EJLT661>3.0.CO;2-D

10.1002/1438-9312(200205)104:5<262::AID-EJLT262>3.0.CO;2-B

10.1080/10408390600754248

10.1007/s11746-006-1197-8

10.1007/s11746-008-1274-2

10.1021/jf9026266

10.1007/BF02522884

Wanasundara P. K. J. P. D., 2005, Bailey's Industrial Oil and Fat products, 431

10.1039/c1fo10046g

10.3109/10715769009148569

10.1111/j.1365-2621.2000.tb10596.x

10.1080/10408391003672086

10.1016/j.foodchem.2009.06.004

10.1111/j.1745-4522.1998.tb00119.x

10.1007/BF02545304

10.1007/BF02632143

10.1007/s11746-998-0231-4

Yanishlieva N. V., 2003, Lipid Oxidation Pathways, 85

10.1002/ejlt.200700195

10.1007/BF02677029

10.1016/S0308-8146(98)00082-X

10.1021/jf072071o

10.1016/j.foodchem.2011.11.144

10.1021/jf300138h

10.1007/978-1-4757-9351-2_19

10.1021/jf00087a009

Porter W. L., 1993, Antioxidants: Chemical, Physiological, Nutritional and Toxicological Aspects, 93

10.1021/jf00041a001

10.1021/jf950374p

10.1002/(SICI)1097-0010(199610)72:2<201::AID-JSFA632>3.0.CO;2-Q

10.1021/jf960068r

10.1021/jf991289a

10.1016/j.foodchem.2006.10.034

10.1002/ejlt.200500292

10.1007/s11746-003-0719-8

10.1021/jf010193p

10.1271/bbb.70.457

10.1016/j.foodchem.2009.04.007

10.1021/jf9609744

10.1021/jf060520z

10.1021/jf9023867

10.1021/jf104750m

10.1021/jf00054a007

10.1002/ejlt.200390021

10.1016/S1359-0294(03)00022-0

10.1021/jf990203a

10.1016/j.tifs.2010.11.003

10.1021/jf950777p

10.1021/jf9505685

10.1007/s11746-010-1696-5

10.1021/jf1009928

10.1016/j.cis.2006.05.005

10.1016/j.foodchem.2009.04.078

10.1007/s002170100318

10.1021/jf9806661

10.1016/S0308-8146(97)00058-7

10.1002/1438-9312(200208)104:8<513::AID-EJLT513>3.0.CO;2-9

10.3989/gya.2003.v54.i1.272

10.1134/S1070363208080124

10.1016/S0308-8146(03)00148-1

10.1021/jf058012x

10.1016/j.foodchem.2008.03.045

10.1111/j.1365-2621.2011.02655.x

10.1021/j100169a052

10.1080/02648725.1994.10647914

10.1039/tf9484400376

Surabhi K., 2010, Microemulsions developmental aspects, Res. J. Pharm., Biol. Chem. Sci, 1, 683

Mehta S. K., 2011, Thermodynamics, 381

10.1016/S0169-409X(00)00103-4

Kortenska V. D., 2001, Effect of lipid hydroxy compounds on the phenol antioxidant efficiency in lipid autoxidation, Cr. Acad. Bulg. Sci, 54, 29

Frankel E. N., 1998, Lipid Oxidation

10.1021/la904139b

10.1111/j.1745-4522.2000.tb00167.x

Nicholson M., Additives Improve Fuel Oil Properties. Bunker World: Marine Additives Special

10.3103/S0027131410030193

10.1021/la0103721

Griffin W., 1954, Calculation of HLB values of non‐ionic surfactants, J. Soc. Cosmet. Chem, 5, 249

Davies J. T. A quantitative kinetic theory of emulsion type. 1. Physical chemistry of the emulsifying agent in: Gas/Liquid and Liquid/Liquid Interfaces Proceedings of the 2nd International Congress Surface Activity Vol. 1 Butterworths (London) 1959 pp. 426–438.

10.1039/f29767201525

10.1039/f29817700601

Krei G., 1995, Extraction of α‐amylase using BDBAC reversed micelles, Bioseparation, 5, 175

10.1016/j.seppur.2006.10.001

10.1021/j100166a077

10.1016/0021-9797(91)90350-H

10.1021/la00087a030

10.1021/la00027a010

10.1021/la00036a008

10.1007/BF02543546

10.1246/bcsj.65.679

10.1007/s11746-000-0085-6

10.1002/ejlt.200700265

10.1016/j.procbio.2009.09.005

10.1021/jf101472n

10.1021/jf061340s

10.1007/s11746-997-0178-x

10.1080/01932690802483817

10.1016/0734-9750(88)90002-X

10.1016/0141-0229(86)90020-7

10.1016/S0032-9592(97)00072-1

10.1021/jf980955p

10.5650/jos1956.44.425

Talbot G., 2013, Trans Fatty Acids—The Options

10.1007/BF02641498

10.1007/BF02660573

10.1007/s11746-997-0022-3

10.1007/BF02540655

10.1271/bbb.61.1036

10.11301/jsfe.10.9

Kashima M., 1984, The antioxidant effects of phospholipids on perilla oil, J. Am. Oil Chem. Soc, 61, 950

10.1007/BF02635893

10.5650/jos1956.41.130

10.1016/S0378-5173(97)00168-3

10.1002/1097-0010(200010)80:13<1925::AID-JSFA714>3.0.CO;2-4

10.1002/ejlt.200390000

10.1016/j.foodchem.2004.11.002

Bendini A., 2010, Stability of the sensory quality of virgin olive oil during storage: An overview, Italian Food & Beverage Technology, 5

Gramza‐ Michalowska A., 2010, The antioxidant potential of carotenoid extract from Phaffia Rhodozyma, ACTA Sci. Pol. Technol. Aliment, 9, 171

10.1021/jf2030314

Rukmini A., 2012, Formulation and stability of water‐in‐virgin coconut oil microemulsion using ternary food grade nonionic surfactants, Int. Food Res. J, 19, 259

10.3989/gya.2005.v56.i4.97

10.1021/jf970055t

10.1002/ejlt.200700317

10.1021/jf2026742

10.1002/jsfa.2740470209

10.1007/BF02660609

10.1002/lipi.19930950110

10.1002/jsfa.2740680119

10.1111/j.1365-2621.1987.tb06741.x

10.1021/jf035316f

10.1007/s11746-999-0239-4

10.1111/j.1365-2621.1987.tb06727.x

10.1111/j.1365-2621.1988.tb07869.x

Caponio F, 2011, Do monoacylglycerols act as pro‐oxidants in purified soybean oil? Evidence of a dose‐dependent effect, Itl. J. Food Sci, 239

10.1007/s11746-005-1051-z

10.1007/BF02636106

10.1021/jf0483220

10.1111/j.1750-3841.2008.00852.x

10.1021/jf9504935

10.1007/s11746-998-0232-3

10.1016/S0963-9969(00)00150-2

10.1016/j.foodchem.2011.02.022

10.1007/BF02787440

10.1021/jf00051a044

10.1021/jf060848s

10.1016/j.foodchem.2007.12.082

10.1016/j.foodres.2009.06.001

10.1016/S0308-8146(00)00161-8

10.5650/jos.53.581

10.1016/j.foodchem.2011.02.061

10.1002/jsfa.2740680314

10.1021/jf0111458

10.1007/s11746-005-1049-6

10.1016/j.foodchem.2010.04.080

10.1021/jf049168k

10.1007/s00217-005-0031-0

10.1016/j.foodchem.2006.05.010

10.1016/j.colsurfa.2004.11.040

10.1021/jf0501239

10.1016/0927-7757(94)02743-9

10.1016/S0378-4347(00)00072-4

Wehmeyer K. R., 2004, The application of multiplexed microemulsion electrokinetic chromatography for the rapid determination of log Pow values for neutral and basic compounds, LCGC Asia Pacific, 7, 1078

10.1016/j.theochem.2005.05.030

10.1016/j.theochem.2009.09.011

10.1021/jm000942e

10.1111/j.1745-4522.1997.tb00080.x