FORMATION AND INHIBITION OF HETEROCYCLIC AMINES IN MEAT PRODUCTS by ... PDF
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FORMATION AND INHIBITION OF HETEROCYCLIC AMINES IN MEAT PRODUCTS by KANITHAPORN PUANGSOMBAT B.S., Kasetsart University, Bangkok, Thailand, 2001 M.S., Kasetsart University, Bangkok, Thailand, 2004 AN ABSTRACT OF A DISSERTATION submitted in partial fulfilment of the requirements for the degree DOCTOR OF PHILOSOPHY Food Science KANSAS STATE UNIVERSITY Manhattan, Kansas 2010 ABSTRACT Heterocyclic amines (HCAs) are produced in meats cooked at high temperature, which are potent mutagens and a risk factor for human cancers. Occurrence of HCAs in ready-to-eat (RTE) meat products and cooked meat products based on prevalence of various cooking methods that are preferred among U.S. meat consumers were investigated. The primary HCAs detected in samples were PhIP (2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine), MeIQx (2-amino-3,8- dimethylimidazo [4,5-f]quinoxaline), and DiMeIQx (2-amino-3,4,8-trimethyl-imidazo [4,5- f]quinoxaline). RTE meat products were ranked in the following order of increasing total HCA content: pepperoni (0.05 ng/g) < hot dogs and deli meat products (0.5 ng/g) < fully cooked bacon (1.1 ng/) < rotisserie chicken meat (1.9 ng/g) < rotisserie chicken skin (16.3 ng/g). In cooked meat products, high levels of total HCAs were found in fried pork (13.91 ng/g), fried fish (14.91 ng/g), and fried bacon (17.91 ng/g). Inhibition of HCAs by rosemary extracts, which were extracted with different solvents, were evaluated in cooked beef patties. Five rosemary extracts were 100W (100% water), 10E (10% ethanol), 20E (20% ethanol), 30E (30% ethanol), and 40E (40% ethanol). Rosemary extract 20E containing a mixture of rosmarinic acid (27.3 mg/g), carnosol (72.9 mg/g), and carnosic acid (4.2 mg/g) showed the greatest inhibition of MeIQx (up to 91.7%) and PhIP (up to 85.3%). The effect of enhancement and marination on HCA formation in meat products was investigated. The addition of salt and phosphate greatly improved the water-holding capacity and decreased HCA formation (up to 58%) in enhanced fresh meat products. An greater reduction of HCAs (up to 79%) was found in marinated fresh meat; the enhancement solution for this meat contained ingredients that exhibited good antioxidant properties. FORMATION AND INHIBITION OF HETEROCYCLIC AMINES IN MEAT PRODUCTS by KANITHAPORN PUANGSOMBAT B.S., Kasetsart University, Bangkok, Thailand, 2001 M.S., Kasetsart University, Bangkok, Thailand, 2004 A DISSERTATION submitted in partial fulfilment of the requirements for the degree DOCTOR OF PHILOSOPHY Food Science KANSAS STATE UNIVERSITY Manhattan, Kansas 2010 Approved by: Major Professor J. Scott Smith ABSTRACT Heterocyclic amines (HCAs) are produced in meats cooked at high temperature, which are potent mutagens and a risk factor for human cancers. Occurrence of HCAs in ready-to-eat (RTE) meat products and cooked meat products based on prevalence of various cooking methods that are preferred among U.S. meat consumers were investigated. The primary HCAs detected in samples were PhIP (2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine), MeIQx (2-amino-3,8- dimethylimidazo [4,5-f]quinoxaline), and DiMeIQx (2-amino-3,4,8-trimethyl-imidazo [4,5- f]quinoxaline). RTE meat products were ranked in the following order of increasing total HCA content: pepperoni (0.05 ng/g) < hot dogs and deli meat products (0.5 ng/g) < fully cooked bacon (1.1 ng/) < rotisserie chicken meat (1.9 ng/g) < rotisserie chicken skin (16.3 ng/g). In cooked meat products, high levels of total HCAs were found in fried pork (13.91 ng/g), fried fish (14.91 ng/g), and fried bacon (17.91 ng/g). Inhibition of HCAs by rosemary extracts, which were extracted with different solvents, were evaluated in cooked beef patties. Five rosemary extracts were 100W (100% water), 10E (10% ethanol), 20E (20% ethanol), 30E (30% ethanol), and 40E (40% ethanol). Rosemary extract 20E containing a mixture of rosmarinic acid (27.3 mg/g), carnosol (72.9 mg/g), and carnosic acid (4.2 mg/g) showed the greatest inhibition of MeIQx (up to 91.7%) and PhIP (up to 85.3%). The effect of enhancement and marination on HCA formation in meat products was investigated. The addition of salt and phosphate greatly improved the water-holding capacity and decreased HCA formation (up to 58%) in enhanced fresh meat products. An greater reduction of HCAs (up to 79%) was found in marinated fresh meat; the enhancement solution for this meat contained ingredients that exhibited good antioxidant properties. Table of Contents LIST OF FIGURES .......................................................... xii LIST OF TABLES ........................................................... xiv ACKNOWLEDGMENTS .................................................... xvii PART I. REVIEW OF LITERATURE ...........................................1 INTRODUCTION .......................................................1 CLASSIFICATION AND FORMATION OF HETEROCYCLIC AMINES .......... 3 Non-polar heterocyclic amines .......................................5 Polar heterocyclic amines ...........................................7 HETEROCYCLIC AMINES AND HUMAN HEALTH ........................12 Epidemiological studies ...........................................12 Colorectal cancer ...........................................13 Breast cancer ..............................................14 Prostate cancer .............................................14 Pancreatic cancer ...........................................15 Uncertainties associated to epidemiological results ................. 15 Bioavailability of heterocyclic amines in humans ........................16 Metabolic bioactivation of heterocyclic amines .........................16 DNA adduct formation ............................................ 19 Carcinogenicity ..................................................21 v Mutagenicity ...................................................23 Chemopreventive of heterocyclic amines in human ......................25 Occurrence of heterocyclic amines in foods ............................26 HUMAN INTAKE OF HETEROCYCLIC AMINES ...........................28 FACTORS AFFECTING HETEROCYCLIC AMINE FORMATION ..............31 Temperature and time of cooking ....................................31 Cooking methods .................................................35 Concentration of precursors .........................................36 Creatine and creatinine.......................................37 Sugar ....................................................37 Amino acids ...............................................38 Moisture contents .................................................38 Lipid .... ...................................................... 39 Meat characteristics ...............................................40 Presence of other compounds ....................................... 42 INHIBITION OF HETEROCYCLIC AMINE FORMATION ....................42 Modifying cooking methods ........................................43 Improving water-holding capacity ....................................43 Marination ......................................................44 Addition of Antioxidants ...........................................46 Synthetic Antioxidants .......................................46 Natural Antioxidants ........................................47 vi ANALYSIS OF HETEROCYCLIC AMINES IN FOODS .......................49 Extraction and clean-up ............................................49 Identification and quantitation .......................................51 REFERENCES ........................................................53 PART II. HETEROCYCLIC AMINE CONTENT IN COMMERCIAL READY TO EAT MEAT PRODUCTS ....................66 ABSTRACT ...........................................................66 MATERIALS AND METHODS ...........................................68 Materials .......................................................68 Chemicals .......................................................68 Sample preparation methods ........................................70 Chemical analyses ................................................71 Extraction and analysis of HCAs ....................................73 Quantitation, recovery, and spectral matching ...........................74 Statistical analyses ................................................75 RESULTS AND DISCUSSION ...........................................76 CONCLUSIONS ....................................................... 87 REFERENCES ........................................................88 vii PART III. OCCURRENCE OF HETEROCYCLIC AMINES IN COOKED MEAT PRODUCTS .......................................91 ABSTRACT ...........................................................91 INTRODUCTION ......................................................92 MATERIALS AND METHODS ...........................................93 Chemicals .......................................................93 Fresh meat samples ...............................................94 Chemical analyses ................................................94 Cooking procedure and cooking loss ................................. 95 Extraction and analysis of HCAs ...................................100 Quantitation, recovery, and spectral matching ..........................101 Statistical analyses ...............................................102 RESULTS AND DISCUSSION ..........................................102 Chemical analyses ...............................................103 Identification and quantification of HCAs .............................103 CONCLUSIONS ...................................................... 117 REFERENCES .......................................................118 PART IV. INHIBITION OF HETEROCYCLIC AMINE FORMATION IN BEEF PATTIES BY ETHANOLIC EXTRACTS OF ROSEMARY .................121 ABSTRACT ..........................................................121 INTRODUCTION .....................................................122 viii MATERIAL AND METHODS ...........................................124 Materials ......................................................124 Preparation of Ground Beef Patty Samples ............................125 Comparison of Volatile Compounds in Dried Rosemary Leaves and Rosemary Extracts by SPME-GC-MS ..................................125 Extraction, Identification, and Quantification of Phenolic Antioxidants in Rosemary Extracts .........................................126 Determination of Total Phenolic Content in Rosemary Extracts ............ 127 DPPH Radical Scavenging Activity Assay ............................128 Extraction and Analysis of HCAs ...................................128 Standard Curves, Recovery, and Spectral Matching .....................130 Statistical Analyses ..............................................130 RESULTS AND DISCUSSION ..........................................131 Characterization of Phenolic Antioxidants in Rosemary Extracts ........... 131 Total Phenolic Content and Antioxidant Activity .......................134 Comparison of Volatile Compounds in Dried Rosemary Leaves and Rosemary Extracts by SPME-GC-MS ..................................135 Effects of Rosemary Extracts on HCAs Formation in Cooked Beef Patties ...139 CONCLUSIONS ...................................................... 145 REFERENCES .......................................................146 ix PART V. HETEROCYCLIC AMINE CONTENT IN ENHANCED AND MARINATED MEAT PRODUCTS ........................150 ABSTRACT ..........................................................150 INTRODUCTION .....................................................151 MATERIALS AND METHODS ..........................................153 Chemicals ......................................................153 Commercial meat products ........................................154 Sample preparation ..............................................155 Chemical analyses ...............................................158 pH measurement ..........................................158 Creatine determination ......................................158 Total phenolic content determination ..........................159 DPPH radical scavenging activity ............................. 159 Cooking procedure and cooking loss ................................. 160 Extraction and analysis of HCAs ...................................160 Quantitation, recovery, and spectral matching ..........................162 Statistical analyses ...............................................163 RESULTS AND DISCUSSION ..........................................163 Commercial meat products ........................................163 Beef products .............................................163 Pork products .............................................166 Chicken products ..........................................169 x
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