Acrylamide and Other Hazardous Compounds in Heat-treated Foods

Contents......Page 6
Contributor contact details......Page 14
Foreword......Page 18
Introduction......Page 20
Part I Formation and analysis of hazardous compounds in heat-treated foods......Page 24
1.1 Introduction......Page 26
1.2 The chemistry of the Maillard reaction......Page 27
1.3 Acrylamide and the Maillard reaction......Page 30
1.4 The formation of other potentially toxic compounds in the Maillard reaction......Page 38
1.5 Conclusions......Page 41
1.6 References......Page 42
2.1 Introduction......Page 46
2.2 Formation and possible mitigation strategies......Page 47
2.3 Coffee......Page 57
2.4 Conclusion......Page 60
2.5 References......Page 61
3.1 Introduction......Page 64
3.2 Acrylamide and the raw material......Page 65
3.3 Acrylamide and potato processing......Page 72
3.4 Conclusion......Page 78
3.5 References......Page 79
4.1 Introduction......Page 83
4.2 Formation of PhIP......Page 84
4.3 Conclusions......Page 88
4.4 References......Page 89
5.1 Introduction......Page 91
5.2 Extraction of HCAs and sample preparation......Page 95
5.3 Chromatographic analysis......Page 113
5.4 Identification and quantification methods......Page 130
5.5 Conclusions......Page 133
5.6 References......Page 134
6.1 The analytical task......Page 140
6.3 Sampling requirements......Page 141
6.4 Extraction procedures......Page 143
6.5 Determination by GC-MS after bromination of acrylamide......Page 145
6.6 Determination by GC-MS with no derivatisation......Page 147
6.7 Determination ly LC-MS......Page 148
6.8 Other instrumental methods......Page 150
6.10 Conclusions......Page 151
6.11 References......Page 152
7.1 Introduction to molecular modelling......Page 155
7.2 Development of a (Q)SAR model......Page 158
7.4 Prediction of chemical toxicity by expert systems......Page 161
7.5 The use of the (Q)SAR approach to identify potential toxicants in heat treated foods......Page 163
7.6 Conclusions......Page 181
7.7 References......Page 182
Part II Health risks of acrylamide and other hazardous compounds in heat-treated foods......Page 184
8.1 Introduction......Page 186
8.2 Metabolism and reactivity......Page 187
8.3 Chemical biomarkers, methods and experimental results......Page 190
8.4 Application of biomonitoring in human exposure situations......Page 204
8.5 Comparison with other methods for exposure assessment......Page 207
8.6 Usefulness of biomarkers in risk assessment......Page 209
8.7 Future trends......Page 211
8.9 References......Page 212
9.1 Introduction......Page 218
9.2 Different models to estimate dietary exposure to food contaminants......Page 220
9.3 Dietary AA exposure assessments......Page 222
9.4 Reduction of AA levels in foods: implications......Page 226
9.5 Exposure to AA in relation to reported toxicity......Page 229
9.6 Discussion and European funded research projects......Page 231
9.7 References......Page 233
10.1 Rationale of exposure assessment......Page 237
10.2 Difficulties in exposure assessment of acrylamide......Page 238
10.3 Overview of dietary acrylamide exposure levels......Page 241
10.5 Bioavailability......Page 243
10.7 Biomarkers of acrylamide exposure......Page 244
10.9 References......Page 248
11.1 Introduction......Page 254
11.2 Biomonitoring......Page 256
11.3 Food frequency questionnaires and doneness classification......Page 258
11.5 Conclusion......Page 263
11.7 References......Page 264
12.1 Introduction......Page 270
12.2 Bioactivation of HCAs, DNA adduct formation, mutagenesis, and carcinogenesis......Page 271
12.3 HCA-protein adduct formation with hemoglobin and serum albumin......Page 276
12.4 Analysis of HCAs and their metabolites in human urine......Page 279
12.6 Future trends......Page 285
12.7 Sources of further information......Page 286
12.8 References......Page 287
13.1 Introduction......Page 298
13.2 Exposure assessments......Page 300
13.3 Hazard identification: neurotoxicity, genotoxicity, development and reproductive toxicity......Page 302
13.4 Hazard identification: carcinogenicity......Page 306
13.5 Hazard characterisation: dose response analysis for various effects......Page 309
13.6 Risk characterisation......Page 311
13.8 Acknowledgements......Page 312
13.9 References......Page 313
14.1 Introduction......Page 319
14.2 Formation of HCAs......Page 323
14.3 In vitro and in vivo mutagenicity of HCAs......Page 325
14.4 Metabolism of HCAs......Page 326
14.5 Carcinogenicity of HCAs in rodents......Page 329
14.6 Modulation of carcinogenic activity......Page 332
14.7 Estimation of human intake and exposure to HCAs......Page 333
14.8 Epidemiological studies......Page 336
14.9 Risk of development of human cancer from HCAs......Page 337
14.11 References......Page 338
15.1 Introduction......Page 351
15.2 Occurrence of HMF in foods and other consumer products......Page 352
15.3 Absorption, biotransformation and elimination of HMF......Page 354
15.5 Acute and chronic toxicity of HMF and SMF......Page 359
15.6 Genotoxicity of HMF, SMF and CMF......Page 360
15.7 Carcinogenicity of HMF, SMF and CMF......Page 365
15.8 Other furan derivatives formed from carbohydrates......Page 366
15.9 Conclusions......Page 373
15.11 Acknowledgement......Page 375
15.12 References......Page 376
16 Metabolic factors affecting the mutagenicity of heterocyclic amines......Page 381
16.2 Genotoxicity and carcinogenicity of HCAs in standard models......Page 382
16.3 Biotransformation pathways......Page 393
16.4 Overview of enzyme super-families involved in the biotransformation of HCAs......Page 400
16.5 Identification of specific human enzyme forms involved in the activation and inactivation of individual HCAs......Page 405
16.6 Knockout and transgenic mouse models for HCA-metabolising enzymes......Page 414
16.7 Genetic polymorphism of human enzymes involved in the activation and inactivation of HCAs......Page 415
16.9 Sources of further information......Page 417
16.11 References......Page 418
Part III Minimising the formation of hazardous compounds in foods during heat treatment......Page 428
17.2 Chemical structures......Page 430
17.3 Precursors......Page 431
17.5 Daily intake of HCAs......Page 432
17.7 Effects of varying levels of natural precursors in meat......Page 434
17.8 Cooking methods and ingredients......Page 437
17.9 Conclusions and recommendations......Page 441
17.10 References......Page 442
18 Dietary compounds which protect against heterocyclic amines......Page 448
18.2 Mechanisms of protection......Page 449
18.3 Methodological aspects......Page 454
18.4 Protective effects of different foods and of individual food components......Page 460
18.5 Conclusions and implications for food producers......Page 467
18.7 References......Page 468
19.1 Introduction......Page 482
19.2 Acrylamide formation and ways to reduce its content in bakery products......Page 483
19.3 Conclusions......Page 496
19.4 References......Page 497
20.2 General considerations......Page 501
20.3 Technological approaches for reducing acrylamide and other hazardous materials......Page 504
20.4 Conclusion......Page 510
20.5 Sources of further information......Page 511
20.6 References......Page 512
Appendix I List of abbreviations of heterocyclic amines......Page 517
Appendix II Molecular structures of heterocyclic amines......Page 518
Index......Page 522