Chemical, biological, and functional aspects of food lipids

Chemical, Biological, and Functional Aspects of Food Lipids, Second Edition......Page 1
Chemical and Functional Properties of Food Components Series......Page 2
Chemical, Biological, and Functional Aspects of Food Lipids, Second Edition......Page 3
Contents......Page 5
Preface......Page 8
Editors......Page 10
Contributors......Page 11
1.1 Introduction......Page 13
1.2.1 General Features......Page 14
1.2.4 Polyene Fatty A......Page 17
1.2.6 Oxygenated Fatty A......Page 19
1.3 Acylglycerols......Page 20
1.3.2 Diacylglycerols......Page 21
1.3.4 Phospholipids......Page 22
1.5.1 Introduction......Page 24
1.5.2.1 Structural Nomenclature of Steroids......Page 26
1.5.2.2.2 Aldehydes, Ketones, and Ethers......Page 28
1.5.2.2.3 Alcohols and Derivatives Esters and Ethers......Page 29
1.5.2.2.4 Unsaturation and Skeletal Modifications......Page 30
1.5.3 Carotenoids......Page 31
1.5.3.2 Stereochemistry of Carotenoids......Page 33
References......Page 34
2.1.1 Introduction......Page 35
2.1.2.3 Oxidative R eactions......Page 36
TABLE 2.1 Effect of U nsaturation on the Iodine Value of Individual Fatty A cids......Page 37
2.2.1 Introduction......Page 39
TABLE 2.3 Examples of L ipid Classes L isted in O rder from Most Polar to Least Polar......Page 40
2.2.5 Melting Point......Page 41
2.2.6 Refractive Index......Page 42
TABLE 2.4 Ultraviolet A bsorption Values for C ommon L ipid Functionalities......Page 43
TABLE 2.5 Infrared A bsorption B ands of C ommon L ipid Functionalities......Page 44
References......Page 45
TABLE 2.2 Physical and C hemical Properties of L ipids from D ifferent S ources......Page 38
Contents......Page 46
3.2.2 Solvent Extraction......Page 47
3.2.3 Supercritical Fluid Extraction......Page 49
3.2.4 Accelerated Solvent Extraction......Page 50
3.3.1 Introduction......Page 53
3.3.2 Solvent Fractionation......Page 54
3.3.3.1 Introduction......Page 55
3.3.3.2 Column Chromatography......Page 57
3.3.3.3 Thin-Layer Chromatography......Page 58
3.4.1 Introduction......Page 60
3.4.2 Thin Layer Chromatography?Flame Ionization Detection......Page 61
3.4.3 High- Performance Liquid Chromatography......Page 64
3.4.4.1 Introduction......Page 65
3.4.4.3 Chemical Ionization......Page 66
3.4.4.4 Fast Atom Bombardment......Page 68
3.5.1 Gas Chromatography?Mass Spectrometry......Page 69
3.5.1.2 Fatty Acids......Page 70
3.5.2 Liquid Chromatography?Mass Spectrometry......Page 74
3.5.2.3 Phospholipids......Page 75
3.5.2.5 Tandem Mass Spectrometry......Page 76
3.6 Final Remarks......Page 77
References......Page 79
4.1 Introduction......Page 81
TABLE 4.1 Proximate C ontents of Fat in Food R aw Materials and Products......Page 82
4.2.2.1 Structural Lipids and Depot Fats......Page 83
4.3.1 Nutritional Benefits......Page 84
4.3.2 Food Lipids Posing Health Hazards......Page 85
4.4.1 Introduction......Page 86
4.4.3 The Role of Lipids in Food Texture......Page 87
4.4.4 Lipids and Food Flavor......Page 88
References......Page 89
5.1.1 Cereal Lipids......Page 91
5.1.2 Cotyledon Lipids?Their Role in Seed Structure and Quality......Page 93
5.2.1 Fat in Spreads......Page 94
5.2.2 Fat in Dairy Products......Page 96
5.2.3 Fat in Food Emulsions......Page 100
5.2.4 Emulsified Meat Products......Page 102
References......Page 103
6.1 Introduction......Page 106
6.2.1 Chemical Structure of Phospholipids......Page 107
6.2.3 Structure of Gangliosides......Page 109
TABLE 6.1 Distribution of L ipid C lasses in D ifferent Phospholipid C oncentrates......Page 110
TABLE 6.3 Composition of Major Fatty A cids in 1- and 2- Positions in Phosphatidylcholine %......Page 111
6.4.2 Functions of Phospholipids in Original Food Materials......Page 112
6.5.1 Manufacture of Phospholipid Concentrates......Page 113
TABLE 6.4 Specification of C ommercial L ecithin......Page 114
6.6 Role of Phospholipi ds i n Food Quality......Page 116
6.7 Changes of Phospholipi ds during Food Processing......Page 118
References......Page 119
TABLE 6.5 Fatty A cid C omposition of S oybean L ecithin Determined after E xtraction with D ifferent Solvents % T otal Phospholipids......Page 115
7.1 Introduction......Page 122
7.2.1 Structure and Occurrence......Page 123
7.2.2 Methods of Reducing Cholesterol in Foods......Page 124
7.2.3 Cholesterol and Its Relationship to Atherosclerosis......Page 125
7.2.4 Oxidation of Cholesterol......Page 126
7.3.1 Structure and Occurrence......Page 129
7.3.1.1 Plant Sterols in Food Products......Page 132
7.3.1.2 Food Products E nriched in Phytosterols and Phytostanols......Page 133
7.3.3.1 Oxidation......Page 134
7.3.3.3 Thermal Degradation......Page 136
References......Page 139
8.1 Introduction......Page 144
8.2.1 Structure......Page 145
8.2.2 Metabolism and Functions......Page 146
8.2.3 Deficiency and Excess......Page 147
8.3.1 Structure......Page 148
8.3.2 Metabolism and Functions......Page 149
8.4.1 Structure......Page 150
8.4.2 Metabolism and Functions......Page 152
8.5.1 Structure......Page 154
8.5.2 Metabolism and Functions......Page 155
8.5.3 Deficiency and Excess......Page 156
8.6.2 Occurrence......Page 157
8.6.3 Food Processing......Page 160
8.7 Antioxidant Concurrency......Page 163
References......Page 165
9.2 Free Radicals and Reactive Oxygen Species......Page 171
9.3.1 Free Radical Oxidation......Page 176
9.3.2 Photooxidation......Page 177
9.3.3 Lipoxygenases......Page 178
9.3.4 Secondary Oxidation Products......Page 179
9.3.5 Transition Metals in Lipid Oxidation......Page 180
9.4 Role of ROS in Diseases......Page 181
9.5 Effects of Oxidized Lipids in Nutrition......Page 184
9.6 Methods for Determination of Lipid Oxidation......Page 185
References......Page 189
10.1 Introduction......Page 193
10.2.2 Enzymatic Antioxidants......Page 194
10.2.4.1 Hydrophilic ROS Scavengers......Page 197
10.2.4.2 Hydrophobic ROS Scavengers......Page 198
10.4 Other Actions of Antioxidants......Page 199
10.5.2.1 Food of Plant Origin......Page 200
10.5.2.2 Foods of Animal Origin......Page 204
10.5.2.3 Combining Meat and Fish with Vegetables......Page 206
10.5.3 Antioxidants Formed in Food during Processing......Page 207
10.5.4 Antioxidants Added to Foods......Page 208
10.5.5 Designer Foods with Antioxidants......Page 209
10.6.2 HAT - Based Methods......Page 210
10.6.3 SET Mechanism- Based Methods......Page 211
10.6.4 Other Methods......Page 212
10.7 Final Remarks......Page 213
References......Page 214
11.1 Introduction......Page 218
11.2.1 Coronary Heart Disease......Page 219
11.2.2 Risk Factors......Page 220
11.3.1 Lipids Rich in Saturated Fatty Acids......Page 221
11.3.3 Lipids Rich in PUFA......Page 223
11.3.4 Trans- Fatty Acids......Page 226
11.4 Endogenous and Dietary Cholesterol......Page 227
11.5 T he Clinician\'s View on the Effectiveness of Dietary Supplements......Page 228
References......Page 230
12.1.1 Lipids as a Source of Energy for Growth and Developm ent......Page 234
12.1.2 Dietary Fats as a Source of Bodybuilding Materials......Page 235
12.1.4.2 Influence on H uman H omeostasis and C ardiovascular S ystem......Page 236
12.1.4.3 Proper Functioning of the B rain and R etina......Page 237
12.2 Clinical Importance of PUFAs in Pediatric Diseases......Page 238
12.3.1 Lipid Composition in Human Milk and Artificial Form......Page 239
12.3.2 Proper Fat Intake in Infancy, in School Children, and Adolescents......Page 240
12.3.3 Special Needs for Premature Babies......Page 241
12.4.1 Obesity and Metabolic Syndrome as a Consequence of Junk Food Consump tion......Page 242
12.4.2 Low- Fat Diets......Page 243
References......Page 244
13.2 The Metabolic Aspects of Vision......Page 246
13.3.1 The Lens......Page 247
13.3.3 The Retina......Page 248
13.4.1 The Retina......Page 249
13.4.2 The Lens......Page 251
13.4.3 The Cornea......Page 252
References......Page 253
14.1 Introduction......Page 256
14.2.2 Plant Waxes......Page 257
14.2.3 Storage Lipids in Seeds......Page 258
14.3 Effect of Plant Species on Lipid Composition and Quality......Page 260
14.4.1 Fatty Acid Composition of Traditional Edible Plant Oil\r......Page 261
14.4.2 Oils Containing Unusual or Specific Fatty Acids......Page 263
14.4.3 Oils with Modified Fatty Acid Comp osition......Page 264
14.5.1 Changes during Ripening of Plant Seeds......Page 266
14.5.2 Postharvest Changes of Plant Lipids......Page 267
14.6.1 Changes during the Processing of Oilseeds or Oil-Bearing Fruit Pericarp......Page 268
14.6.3 Changes of Lipids during Culinary Food Preparation......Page 270
14.7 Role and Changes of Plant Lipids in Processed Foods......Page 271
14.8.2 Fractionation of Lipids for Use in Food......Page 272
14.8.3 Hydrogenation of Lipids for Use in Food......Page 273
14.8.4 New Oils Produced by Breeding or Genetic Manipulation......Page 274
14.8.5 Reduced and Zero-Energy Lipids in Foods......Page 275
References......Page 276
Contents......Page 279
15.1 Introduction......Page 280
15.2 Lipid Content......Page 281
15.3 Lipid Composition: Lipid Classes......Page 282
15.4.1 Fatty Acid Groups......Page 284
TABLE 15.1 Atheriosclerosis Index? Ratio S FA.+ MUFA/ PUFA of Fish L ipids......Page 285
15.4.3 n-3/n-6 Ratio......Page 287
15.5.1 Lipid Content......Page 288
15.5.2 Seasonal Variations......Page 289
15.5.5 Diet......Page 290
15.6 Susceptibility to Oxidation......Page 291
15.7.1.1 Chilling......Page 292
15.7.1.2 Frozen S torage......Page 294
15.7.2.1 General Changes of Lipids......Page 298
15.7.2.2 Cooking Methods......Page 299
15.7.2.3 Frying......Page 300
15.7.2.4 Effects of Fish Freshness on Lipid C hanges during Cooking......Page 301
15.7.2.5 Storage of Precooked Fish......Page 302
15.7.3 Canned Fish......Page 303
15.7.4 Smoking......Page 306
15.7.5 Salting......Page 307
15.7.6 Marinading......Page 308
15.8 Dietary Supplements and Food Enrichment with Fish Oil......Page 309
15.9 Final Remarks......Page 310
References......Page 311
Contents......Page 319
16.2.2 Fatty Acids......Page 320
16.2.3 Triacylglycerols......Page 321
16.2.5 Sterols......Page 322
16.2.8 Flavor Compounds......Page 324
16.3.1 Milk Fat Globule Membrane......Page 325
16.3.3 Lipolysis......Page 326
16.4.2 Modification of Properties......Page 327
16.5.2.1 Oleic, Linoleic, and Linolenic A cids......Page 328
References......Page 329
17.1 Introduction......Page 332
17.3 The Fatty Acid Composition of Meat Lipids......Page 333
17.4 The Nutritive Value of Meat Lipids......Page 336
17.5.1 Introduction......Page 337
17.5.2 The Effect of Lipids on Color......Page 338
17.5.3.2 Cooked Meat Flavor......Page 340
17.5.4 Lipids and the Rheological Properties of Meat and Meat Products......Page 342
17.6 Final Remarks......Page 343
References......Page 344
TABLE 17.2 The Formulation for Frankfurter S ausage  United S tates with D ifferent C ontents of Fat......Page 334
TABLE 17.4 Proximate C omposition of the Fatty- Acid R esidues in the L ipids of R ed Meat and Poultry......Page 335
18.1 Egg Shell and Albumen Lipids......Page 346
18.2.1 Introduction......Page 349
18.2.2 Triacylglycerols of Egg Yolk......Page 352
18.2.4 Phospholipids......Page 353
18.2.6 The Lipid Component of Lipoproteins......Page 356
18.2.7 Influence of Diet on the Lipid Composition......Page 360
18.2.8 Positions of Fatty Acids in the Glycerol Molecule......Page 365
18.3.1 Introduction......Page 366
18.3.2 Autoxidation of Cholesterol......Page 368
18.3.3 Technological Dependencies for the Formation of Oxidation Products of Cholesterol......Page 374
18.3.4.1 Influencing Cholesterol Content by Genetic Selection, Hens\' Diet, or Drugs......Page 376
18.3.4.2 Reduction of Egg Yolk Cholesterol through Enzymatic Methods......Page 380
18.3.4.3 Removing Cholesterol by Physical Treatments and Effects on Functional Properties of Egg Yolk......Page 381
References......Page 382
19.1 Introduction......Page 388
19.2 Characteristic of Fat Replacers......Page 391
19.3.1 Modified Vegetable Oils......Page 393
19.3.2 Fat Modified by Feeding of Animals......Page 395
19.4.1 Blends......Page 396
19.4.2 Fractionation......Page 397
19.4.3 Hydrogenation......Page 398
19.4.4 Chemical Interesterification......Page 399
19.5.1 Enzymatic Modification of Fats and Oils......Page 402
19.5.2 Lipids from Genetically Modified Organisms......Page 405
19.5.3 Alternative Fats and Oils......Page 406
19.6 Modified Triacylglycerols and Fat Replacers and Their Effects on Food Quality......Page 409
References......Page 410
20.1 Introduction......Page 414
20.2 Biological Activity of Lipids Containing Polyenoic and Conjugated Fatty Acids......Page 416
20.3 Antimicrobial and Surface Activity of Lipids......Page 420
20.4 Modification of Phospholipids and Their Role......Page 422
20.5.2 Gamma-Linolenic Acid......Page 426
20.5.3 Fish Oils as a Material for Synthesis of sTAG......Page 428
References......Page 429
Contents......Page 433
21.1 Introduction......Page 434
21.2.2 Types of Oils Used for Frying......Page 435
21.3.3 Chemical Reactions......Page 436
21.3.4 Interactions between Frying Oil and Food Comp onents......Page 438
21.3.5 Desirable and Undesirable Changes Due to Deep-Fat Frying......Page 439
21.4.2 The Importance of FA Composition......Page 440
21.4.4 Stabilization of Frying Oils with Synthetic and Natural Antioxidants......Page 441
21.4.5.1 Introduction......Page 442
21.4.5.2 Heating of Olive Oil and Phenolic Compounds......Page 443
21.5.1 Introduction......Page 444
21.5.2 Traditional and Standardized Methods......Page 445
21.5.4 Total Polar Compounds and Polymers......Page 446
21.5.5 Polymerized TAG and Other Approaches......Page 447
21.6.2 Intake of Fat......Page 448
21.6.4 Frying Oils as Sources of Natural Antioxidants......Page 449
21.6.5.1 Thermally O xidized Fats and O xidative S tress......Page 450
21.6.5.3 Polar Compounds......Page 451
21.6.5.4 Acrylamide......Page 452
21.6.6 Conclusions......Page 453
References......Page 454
22.1 Introduction......Page 459
22.2.1 Dispersible Lipoproteins......Page 460
22.2.2 Lipoprotein Membranes......Page 461
22.3.2 Changes of Food Lipoproteins during Frying......Page 462
22.3.3 Effect of Oxidized Lipoproteins on Other Food Comp onents......Page 463
22.4.1 Effect on the Nutritional Value of Food......Page 465
22.4.2 Effect on the Sensory Value of Fried Food......Page 466
22.5.1 Reactions of Lipids and Oxidized Lipids with Saccharides......Page 467
22.5.2 Amylose and Lipid......Page 468
22.5.4 Effects of Lipid Freshness on Lipid?Saccharide Interactions......Page 469
22.6 Final Remarks......Page 470
References......Page 472
23.2 Trace Metals......Page 476
23.3 Pesticides......Page 479
23.5 Polycyclic A romatic H ydrocarbons......Page 481
23.6 Fungal T oxins......Page 483
23.7 Plasticizers......Page 484
References......Page 485