Inhibitory activity of Asian spices on heterocyclic amines formation in cooked beef patties

Heterocyclic amines (HCAs) are mutagenic compounds formed when foods are cooked at high temperatures. Numerous reports have shown that natural antioxidants from spices, fruits, chocolate, and tea can inhibit formation. In this study, we evaluated HCA formation in the presence of 5 of Asian spices: galangal (Alpinia galangal), fingerroot (Boesenbergia pandurata), turmeric (Curcuma longa), cumin (Cuminum cyminum), and coriander seeds (Coriandrum sativum). HCA levels were compared to patties containing rosemary (Rosmarinus officinalis), of which the inhibitory effect is well documented. Inhibition of HCA formation by the spices was evaluated in beef patties cooked at 204 °C (400 °F) for 10 min. All spices were mixed into patties at 0.2% before cooking, and HCAs levels were measured in the final product. All patties, including the control, contained 2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline (MeIQx) and 2-amino-1-methyl -6-phenylimidazo [4,5-b]pyridine (PhIP). The average HCA content of the control patties was 7 ng/g MeIQx and 6.53 ng/g PhIP. Turmeric (39.2% inhibition), fingerroot (33.5% inhibition), and galangal (18.4% inhibition) significantly decreased HCAs compared with the control. But, only turmeric and fingerroot were as effective as rosemary in preventing HCA formation. The HCA inhibition in patties containing spices was significantly correlated to the total phenolic content (R(2) = 0.80) and the scavenging activity (R(2) = 0.84) of the spices as measured by the 2,2-diphenyl-β-picrylhydrazyl assay. Results of this study suggest that addition of Asian spices can be an important factor in decreasing the levels of HCAs in fried beef patties.     

Effects of different types of soy sauce on the formation of heterocyclic amines in roasted chicken

The objective of the study was to determine the effect of different types of soy sauce and marinating time on the formation of heterocyclic amines (HCAs) in roasted chicken. Chicken breast samples were marinated with sweet, salty, light and dark soy sauce at 0, 3, 6 and 12 h (control treatment was the chicken without marinade). The concentrations of free amino acids, sugars and creatinine were determined before roasting while HCA concentrations were determined after roasting. All types of soy sauce significantly increased (p ≤ 0.05) the concentration of HCAs in roasted chicken with increasing marinating time. The highest increment of total concentration of HCAs was found in samples marinated with light soy sauce (887%) followed by dark (375%), salty (193%) and sweet (169%) at 12 h. PhIP (2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine) showed a substantial reduction in samples only momentarily marinated with sweet, salty and dark soy sauce (0 h). Free amino acids were found to be more strongly correlated with the formation of HCAs than reducing sugars or creatinine.     

Effect of Marinades on the Formation of Heterocyclic Amines in Grilled Beef Steaks

ABSTRACT:  Heterocyclic amines (HCAs) are suspected human carcinogens formed in muscle foods during high temperature grilling or cooking. Inhibition of HCAs by commercial marinades rich in polyphenolic antioxidant containing spices was evaluated with beef round steaks cooked at 204 °C (400 °F). Treatment effects on the levels of 4 HCAs were investigated: 2-amino-3,8-dimethylimidazo[4,5- f ]quinoxaline (MeIQx), 2-amino-1-methyl-6-phenyl-imidazo[4,5- b ]pyridine (PhIP), 1-methyl-9H-pyrido[4,3- b ]indol (harman), and 9H-pyrido[4,3- b ]indol (norharman). The marinades were formulated according to the package label instruction in an oil, water, and vinegar mixture, and the steaks were treated for 1 h prior to grilling. All 3 marinades, Caribbean, Southwest, and herb, significantly decreased the imidazo-azaarene HCAs (MeIQx, PhIP) as contrasted to controls and liquid blanks. The Caribbean mixture showed the highest decrease in the total HCA content (88%), followed by the herb (72%) and Southwest (57%). With a few exceptions there were significant decreases in HCAs for treatments with only the marinade bases (ingredients without any spices/herbs). As measured by high-performance liquid chromatography (HPLC), the marinades contained considerable amounts of the polyphenolic antioxidants carnosic acid, carnosol, and rosmarinic acid with Caribbean being the highest. Commonly available spice-containing marinades can be effective inhibitors of HCA formation and provide reduced exposure to some of the carcinogens formed during grilling.     

Influence of natural food ingredients on the formation of heterocyclic amines in fried beef patties and chicken breasts

The effects of natural food ingredients including Korean bramble, onion, and marinade sauce with water extracts of olive and lotus leaf on the formation of 15 heterocyclic amines (HCAs) were evaluated in fried beef patties and chicken breasts. The patties and chicken breasts containing natural food ingredients were fried at 230 and 200°C for 8 min on each side. Addition of 4 g Korean bramble to beef patties reduced the formation of 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ), 9H-pyrido [3,4-b]indole (Norharman), and 2-amino-6-methyldipyrido [1,2-a:3′,2′-d]imidazole (Glu-P-1) by 74, 62, and 39%, respectively. Also, when 2 g onion was added to beef patties, the formation of 2-amino-3,4,8-trimethylimidazo [4,5-f]quinoxaline (4,8-DiMeIQx), Glu-P-1, MeIQ, Norharman, and 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine (PhIP) was inhibited by 100, 96, 88, 74, and 79%, respectively. When marinade sauce containing 2% water extracts of olive and lotus leaf was added to chicken breasts, most HCAs formation was inhibited. Especially, the formation of Glu-P-1, 2-aminodipyrido [1,2-a:3′,2′-d]imidazole (Glu-P-2), and MeIQ were reduced by 100%.     

Comparative mutagenicity studies on fried minced beef,grilled sausage and grilled hamburgers

The mutagenicity of the basic fractions of fried beef patties, grilled hamburgers and grilled sausages was determined in the Ames test using activation systems (S9-mix) derived from untreated and Aroclor-pretreated rats and hamsters, and from rats pretreated with 3-methylcholanthrene or phenobarbitone. In order to indicate whether the mutagenic activity was due to the presence of thermally generated amino imidazo aza-arenes of the type previously identified in heated meat products (i.e. 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,4-dimethylimidazo-[4,5-f]quinoline (MeIQ) and 2-amino-3,8-dimethylimidazo[4,5-f]quin-oxaline), these compounds were assayed under the same conditions. The mutagenicity of the basic fractions of the cooked foods and of the three aza-arenes varied with the activation system used. The activation patterns of the basic fractions from fried beef and grilled sausages resembled that of IQ, whereas that of grilled hamburgers was more similar to that of MeIQ. Interestingly the total mutagenic activity of fried beef patties was greater than that of grilled hamburgers.     

Inhibition of Heterocyclic Amine Formation in Beef Patties by Ethanolic Extracts of Rosemary

ABSTRACT: Heterocyclic amines (HCAs) are mutagenic compounds formed during cooking muscle foods at high temperature. Inhibition of HCAs by rosemary extracts were evaluated with beef patties cooked at 191 °C (375 °F) for 6 min each side and 204 °C (400 °F) for 5 min each side. Five rosemary extracts extracted with different solvents were used in this study: extract 100W (100% water), 10E (10% ethanol), 20E (20% ethanol), 30E (30% ethanol), and 40E (40% ethanol). The 5 extracts were directly added to beef patties at 3 levels (0.05%, 0.2%, and 0.5%) before cooking and HCA contents were extracted and quantified. All of the patties contained 2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP). There was no statistical difference in the inhibition of HCAs in the 0.05%, 0.2%, and 0.5% rosemary extracts. All rosemary extracts significantly decreased the levels of MeIQx and PhIP at both cooking conditions. When cooking at 204 °C (400 °F) for 5 min each side, rosemary extracts 10E and 20E were superior to rosemary extracts 100W, 30E, and 40E in inhibiting HCA formation. Rosemary extract 20E showed the greatest inhibition of MeIQx (up to 91.7%) and PhIP (up to 85.3%). The inhibiting effect of rosemary extracts on HCA formation corresponded to their antioxidant activity based on a DPPH scavenging assay. Rosemary extract 10E and 20E contain a mixture of rosmarinic acid, carnosol, and carnosic acid. It is possible that these compounds might act synergistically in inhibiting the formation of HCAs.     

Determination of Heterocyclic Aromatic Amines in Cooked Commercial Frozen Meat Products by Ultrafast Liquid Chromatography

This paper describes a method for the determination of nine heterocyclic aromatic amines (HCAs) in commercial frozen meat products, which were sold in Turkey by ultrafast liquid chromatography (UFLC) with ultraviolet visible detection. HCAs are separated on a Shim-pack XR-ODS (7.5?×?3 mm, 2.2 μm). Varying levels of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) (up to 1.95 ng/g), 2-amino-3-methylimidazo[4,5-f]quinoxaline (IQx) (up to 4.17 ng/g), 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) (up to 0.69 ng/g), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) (up to 0.83 ng/g), 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx) (up to 0.22 ng/g), 2-amino-3,7,8-trimethylimidazo[4,5-f]quinoxaline (7,8-DiMeIQx) (up to 0.94 ng/g), 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) (up to 4.58 ng/g), 2-amino-9H-pyrido[2,3-b]indole (AαC) (up to 0.57 ng/g), and 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeAαC) (up to 3.51 ng/g) were detected in these commercial frozen meat products of Turkey. The data obtained show clearly that HCAs could be isolated in a very short time (5 min) by using UFLC.     

Simultaneous formation of polycyclic aromatic hydrocarbons (PAHs) and heterocyclic aromatic amines (HCAs) in gas-grilled beef satay at different temperatures

This study investigated the simultaneous formation of polycyclic aromatic hydrocarbons (PAHs) and heterocyclic aromatic amines (HCAs) in gas-grilled beef satay at different temperatures (150, 200, 250, 300, and 350°C). Solid-phase extraction (SPE) was used for sample clean-up. Fifteen PAHs were determined using high performance liquid chromatography with fluorescence detection (HPLC-FLD) and nine HCAs were quantified using liquid chromatography tandem-mass spectrometry (LC-MS/MS) with a gradient programme. The lowest significantly concentrations of PAHs and HCAs were generated at 150°C; the formation of PAHs and HCAs simultaneously increased with temperatures. Benzo[a]pyrene was detected in all samples and increased markedly at 300 and 350°C. The sums of 4 PAHs (PAH4) in marinated beef satay at 300 and 350°C exceeded the maximum level in Commission Regulation (EU) 2015/1125. Significant reductions of polar and non-polar HCAs (except PhIP) were found in marinated beef satay across all temperatures. Overall, PAHs and HCAs showed opposite trends of formation in beef satay with marination.     

Effects of varying degrees of doneness on the formation of Heterocyclic Aromatic Amines in chicken and beef satay

The study was carried out to determine the effect of cooking method on Heterocyclic Aromatic Amines (HAs) concentration in grilled chicken and beef (satay). Six common HAs were investigated: 2-amino-3-methylimidazo[4,5-f]quinolone (IQ), 2amino 3,4dimethylimidazo [4,5f]quinoline (MeIQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3,4,8 trimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx), 2-amino-3,7,8trimethylimidazo [4,5-f]quinoxaline (7,8-DiMeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Chicken and beef satay samples were grilled to medium and well done level of doneness. Charcoal grilled (treatment A), microwave pre-treatment prior to grilling (treatment B), and microwave-deep fried (treatment C) were applied to beef and chicken satay samples. The satay samples which were microwaved prior to grilling (B) showed significantly (p < 0.05) lower HAs concentration as compared to those charcoal grilled (A). Both medium and well done cooked beef and chicken satay samples that were microwaved and deep fried (C) as an alternative method to grilling were proven to produce significantly lesser HAs as compared to charcoal-grilled (A) and microwaved prior to grilling (B).     

Development of a New Extraction Method for Heterocyclic Aromatic Amines Determination in Cooked Meatballs

Heterocyclic aromatic amines (HCAs) are mutagenic and carcinogenic compounds that are produced in meats cooked at high temperature. In this study, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), 9H-pyrido[3,4-b]indole (norharman), and 1-methyl-9H-pyrido[3,4-b]indole (harman) were studied. A new extraction method was developed for the determination of heterocyclic amines with high-performance liquid chromatography (HPLC). Linearity for each HCA was observed with a high regression coefficient (r?=?0.9999, P?<?0.01 for IQ; r?=?0.9990, P?<?0.01 for MeIQx; r?=?0.9989, P?<?0.01 for 4,8-DiMeIQx; r?=?0.9934, P?<?0.05 for PhIP; r?=?1.000, P?<?0.01 for norharman; r?=?0.9991, P?<?0.01 for harman). Limits of detection for various HCAs were found between 0.04 and 1.40 ng/g. Limits of quantification were found in the range of 0.13–4.40 ng/g. Recovery rates varied from 68.9 % to 87.8 %. This method was compared with two different common HCA extraction methods in literature. The optimized new extraction method and the other two methods were used for the determination of HCAs in ten different cooked meatball samples. Sample extraction procedures of HCAs were investigated in more detail, and a rapid, accurate, precise, and reliable extraction method was developed.     

The tenderisation of shin beef using a citrus juice marinade

The effectiveness of organic acids (acetic, citric, lactic) and a citrus juice marinade as tenderising agents in shin beef muscle was investigated. At 0.2 M, citric acid was more effective as a tenderising agent than acetic or lactic acid. Immersion of shin beef strips in citric acid (0-0.05 M) showed that a significant tenderising effect was obtained above a concentration of 0.013 M. When shin beef strips were immersed in the citrus juice marinade (31% orange juice, 31% lemon juice, 38% distilled water) mean pH decreased from 5.7 to 3.1 and mean sample weight increased by ～65%. The mean Warner-Bratzler shear force value decreased from 178 to 44 N cm(-2) following marination while mean sensory analysis scores for tenderness and juiciness increased following marination. A mean total collagen content of 1.4 g/100 g was recorded in shin beef of which 9% was soluble in unmarinated samples and 29% was soluble in marinated samples. The results indicated that the tenderisation of beef samples using a citrus juice marinade could be attributed to marinade uptake by muscle proteins and also to solubilisation of collagen.     

Incorporation of herbs into sandesh, an Indian sweet dairy product, as a source of natural antioxidants

Indian herbs such as turmeric ( Curcuma longa L.), coriander ( Coriandrum sativum L.), curry leaf ( Murraya koenigii L.), spinach ( Spinacia oleracea ) and aonla ( Emblica officinalis ) are good sources of antioxidants. These herbs, as a paste, were incorporated separately at the 10% level into sandesh (a heat-desiccated product of coagulated milk protein mass or chhana, which is analogous to cottage cheese). Their total antioxidative status was assessed in vitro using Randox's method. The antioxidative levels of the various herbs were compared with the synthetic antioxidants TBHQ and BHA: BHT (1:1) at 100 and 200 mg/kg levels. The antioxidative effect of herbal sandesh decreased in the order turmeric > curry leaf > aonla > spinach > coriander leaf. Total antioxidative statuses of herbal sandesh were lower than samples with TBHQ but similar to those with 200 mg/kg BHA: BHT (1:1). The proximate composition of herbal sandesh was comparable with control sandesh. Incorporation of herbs at the level used did not significantly affect the overall acceptability of sandesh. Considering all the findings, it can be concluded that herbal sandesh is a more value-added health food than the control sandesh.     

Cooking with elaborate recipes can reduce the formation of mutagenic heterocyclic amines and promote co-mutagenic amines

Heterocyclic amines (HCAs) are foodborne carcinogens for which their formation is highly dependent on cooking conditions. HCAs have been commonly quantified in food items prepared with simple procedures. This approach is suitable for elucidating HCAs’ formation, but it only partially reflects the contamination in consumed food. In the current investigation, the generation of HCAs has been investigated in fried beef items prepared with elaborated cooking recipes, and their occurrence has been compared with control beef fried without the addition of ingredients other than oil. The food recipes that included a variety of food ingredients had lower yields of mutagenic HCAs (≥47% reduction, with individual HCA levels ranging between 0.01 and 2.22 ng/g) with respect to the control beef. In contrast, the co-mutagens norharman and harman were formed generally at greater levels (up to three times the contamination in the control fried beef) in the items prepared including a greater variety of ingredients.     

Influence of extra virgin olive oil on the formation of heterocyclic amines in roasted beef steak

In this study, heterocyclic anime (HCA) contents were monitored in commonly consumed pan-fried beefsteak based on the highest level of human exposure. Effect of addition of extra virgin olive oil (EVOO) on HCAs formation in fried beef steaks was evaluated. After EVOO was spread on the meat surface, the raw beef was cooked at 200°C for 5 min on each side. The HCAs were extracted from the meat samples and purified using a solid-phase extraction method and then analyzed by liquid chromatography-mass spectrometry (LC-MS). Among the 15 HCAs, 3-amino-1,4-dimethyl-5H-pyrido-[4,3-b]indole (Trp-P-1), 3-amino-1-methyl-5H-pyrido [4,3-b]indole (Trp-P-2), 9H-pyrido [3,4-b]indole (Norharman), 1-methyl-9H-pyrido [3, 4-b]indole (Harman), 2-amino-9H-pyrido [2,3-b]indole (AαC), 2-amino-3-methyl-9H-pyrido [2,3-b]indole (MeAαC), 2-amino-3,8-dimethylimidazo [4,5-f]-quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo [4,5-b]-pyridine (PhIP) were detected in all of the cooked beefsteaks. HCAs formation was significantly reduced (p<0.05) when the EVOO was added to the beef prior to cooking. The addition of 2 and 4 g of EVOO considerably inhibited HCAs formation in the fried beefsteak. However, adding excess amounts of EVOO promoted some HCAs formation.     

Occurrence of heterocyclic amines in cooked meat products

Heterocyclic amines (HCAs), potent mutagens and a risk factor for human cancers, are produced in meats cooked at high temperature. The aim of this study was to determine the HCA content in cooked meat products (beef, chicken, pork, fish) prepared by various cooking methods (pan frying, oven broiling, and oven baking at 170 to 230 °C) that are preferred by U.S. meat consumers. The primary HCAs in these samples were PhIP (2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine) (1.49-10.89 ng/g), MeIQx (2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline) (not detected-4.0 ng/g), and DiMeIQx (2-amino-3,4,8-trimethyl-imidazo [4,5-f]quinoxaline) (not detected-3.57 ng/g). Type and content of HCAs in cooked meat samples were highly dependent on cooking conditions. The total HCA content in well-done meat was 3.5 times higher than that of medium-rare meat. Fried pork (13.91 ng/g) had higher levels of total HCAs than fried beef (8.92 ng/g) and fried chicken (7.00 ng/g). Among the samples, fried bacon contained the highest total HCA content (17.59 ng/g).     

Determination of 3-MCPD in grilled meat using pressurized liquid extraction and gas chromatography–high resolution mass spectrometry

An analytical method for the determination of free 3-monochloropropane-1,2-diol (3-MCPD) in grilled meat using pressurized liquid extraction, derivatisation using phenylboronic acid, and gas chromatography/high resolution mass spectrometry was developed. The limit of quantification was 1???g/kg. Using this method, the contents of 3-MCPD in grilled steaks (collar) were analysed for different grilling conditions. Charcoal, an electric grill, and a gas grill were used for grilling collars. Further parameters investigated were the pre-treatment of meat (untreated, salted, marinated with oil or emulsion marinade), the use of aluminium grill trays, and a lid. For grilled steaks, contents of 3-MCPD in the range of <1 to 365???g/kg (median 16???g/kg) were detected. The highest contamination was found for a steak pre-treated with an oily marinade grilled on a charcoal grill with a closed lid. Consuming such a steak will exhaust the tolerable daily intake of 2???g/kg body weight for 3-MCPD to about 26?%.     

Mycotoxins in spices and herbs–An update

Spices and herbs have been used since ancient times as flavor and aroma enhancers, colorants, preservatives, and traditional medicines. There are more than 30 spices and herbs of global economic and culinary importance. Among the spices, black pepper, capsicums, cumin, cinnamon, nutmeg, ginger, turmeric, saffron, coriander, cloves, dill, mint, thyme, sesame seed, mustard seed, and curry powder are the most popular spices worldwide. In addition to their culinary uses, a number of functional properties of aromatic herbs and spices are also well described in the scientific literature. However, spices and herbs cultivated mainly in tropic and subtropic areas can be exposed to contamination with toxigenic fungi and subsequently mycotoxins. This review provides an overview on the mycotoxin risk in widely consumed spices and aromatic herbs.     

Antioxidant spices reduce the formation of heterocyclic amines in fried meat

 Heterocyclic aromatic amines (HAs) are mutagenic compounds that are formed during heating of meat and fish. These substances are reaction products of creatine with amino acids and carbohydrates. It is recommended that exposure to these probable human carcinogens should be minimised. Five heterocyclic aromatic amines which occur in beef were investigated: 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ), 2-amino-3,4-dimethyl-imidazo[4,5-f]quinoline (MeIQ), 2-amino-3,8-dimethyl-imidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3,4,8-trimethyl-imidazo[4,5-f]quinoxaline (4,8-DiMeIQx), and 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP). Clean-up was done by acid-base partition followed by SPE using blue cotton. HPLC analysis was carried out by using electrochemical detection for IQ- and IQx-type compounds and fluorescence detection for PhIP. The concentrations of the aromatic amines were as follows: IQ, 10.2 μg/kg; MeIQ, 2.46 μg/kg; MeIQx, 13.2 μg/kg; 4,8-DiMeIQx, 2.26 μg/kg; and PhIP, 5.48 μg/kg. The application of spices (rosemary, thyme sage, garlic, brine) reduced the content of the HAs below 60% of the amount found in the control. Received: 23 April 1998     

Influence of fructooligosaccharides and garlic on formation of heterocyclic amines in fried ground beef patties

The effects of fructooligosaccharide (FOS) and garlic on the formation of 15 heterocyclic amines (HCAs) were evaluated in fried beef patties. The HCAs were extracted from the fried meat samples and purified using a solid-phase extraction method and then analyzed on a liquid chromatography-mass spectrometry. Among the 15 HCAs, 3-amino-1, 4-dimethyl-5H-pyrido-[4,3-b]indole (Trp-P-1), 3-amino-1-methyl-5H-pyrido [4,3-b]indole (Trp-P-2), 2-amino-6-methyldipyrido [1,2-a:3′,2′-d]imidazole (Glu-P-1), 2-aminodipyrido [1,2-a:3′,2′-d]imidazole (Glu-P-2), 9H-pyrido [3,4-b]indole (norharman), 1-methyl-9H-pyrido [3,4-b]indole (harman), 2-amino-9H-pyrido [2,3-b]indole (AαC), 2-amino-3,8 dimethylimidazo [4,5-f]-quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo [4,5-b]-pyridine (PhIP) were detected in all of the cooked beef patties. Analysis of variance revealed that the addition of 1 or 3 g of FOS significantly reduced the formation of total amino-carboline type HCAs in the cooked beef patties, and adding the 1 or 3 g of FOS to ground beef patties reduced levels of PhIP and MeIQx (amino-imidazo-azaarenes; AIAs) in the patties. When it is compared with the HCA formation in control, additions of minced garlic (5.0, 10.0, and 15.0 g) to the ground beef patties (100 g) reduced HCA formation in the range of 14 to 100%.     

Formation of heterocyclic amine–amino acid adducts by heating in a model system

Although mutagenic and carcinogenic heterocyclic amines (HCAs) are known to be formed in cooked meat and fish, human HCA exposure and carcinogenic risk have not been elucidated in sufficient detail. In this work, we investigated the formations of HCA–amino acid adducts in a model system by using a liquid chromatography–mass spectrometry to elucidate another source of human HCA exposure. The 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) adduct with glycine was formed easily by heating at 200 °C within 5 min, which is probably based on the dehydration condensation of the amino group of PhIP and carboxyl group of glycine. PhIP and other HCAs such as 2-amino-3-methyl-3H-imidazo[4,5-f]quinolone, 2-amino-3,8-dimethylimidazo[4,5-f]-quinoxaline and 3-amino-1,4-dimethyl-5H-pyrido[3,4-b]indole, also bound with various amino acids by heating. Among these amino acids, proline tends to form adducts with HCAs, but serine, cysteine and lysine hardly bound with HCAs. These results provided a basic understanding of the formation of HCA adducts with amino acids during cooking.