Formation Of Heterocyclic Aromatic Amines Research Articles

The construction of garlic diallyl disulfide nano-emulsions and their effect on the physicochemical properties and heterocyclic aromatic amines formation in roasted pork

Garlic diallyl disulfide (DAD) nano-emulsions consisting of soy proteins were constructed, and their effects on physicochemical properties and heterocyclic aromatic amines (HAAs) formation in roasted pork were investigated. DAD was well encapsulated by soy proteins with a mean particle of 400–700 nm. Applying DAD nano-emulsions to pork patties significantly altered the color and texture of roasted pork, with a slight increase in brightness and decreases in redness and yellowness. The flavor determination demonstrated that sulfur-containing compound levels in encapsulated DAD were significantly reduced, particularly 7S group compounds, indicating an effective shielding effect on the irritating odor of garlic oil by protein. The levels of three HAAs (MeIQx, PhIP, and Harman) were significantly reduced by DAD nano-emulsion exposure (51.84 %, 76.80 %, and 48.70 %, respectively). This study provides a new method for inhibiting HAA formation and improving the sensory qualities of meat products.

Inhibitory effects of hydrocolloids on the formation of heterocyclic aromatic amines in smoked chicken drumsticks and the underlying mechanism

This study aims to investigate the inhibitory effects of hydrocolloids on heterocyclic aromatic amine (HAA) formation in chemical model systems and smoked chicken drumsticks. In chemical model systems I and II, xanthan gum (XG) and carboxymethyl cellulose sodium (CMC-Na) effectively inhibited the 2-amino-1-methyl-6-phenylimidazo[4,5- b ]pyridine (PhIP), 1-methyl-9H-pyrido[3,4- b ]indole (Harman), and 9H-pyrido[3,4- b ]indole (Norharman) formation in comparison with the control sample ( P < 0.05). Arabic gum (AG) inhibited the PhIP and Harman formation ( P < 0.05), but its inhibitory action against Norharman formation was not significant ( P > 0.05). Further mechanism investigation of chemical model system I showed that the formation of PhIP was mainly inhibited via trapping phenylalanine and creatinine by glyoxal and methyglyoxal. A mechanistic investigation of chemical model system II suggested the inhibition of Harman and Norharman formation by XG and CMC-Na could be through trapping tryptophan by glyoxal and methyglyoxal. In smoked chicken drumsticks, CMC-Na had a dose-dependent inhibitory effect against the PhIP, Harman, and Norharman formation in comparison with the control sample ( P < 0.05), and 2.0% CMC-Na had the highest inhibitory rates of 45.83%, 21.82%, and 30.92%, respectively. Moreover, CMC-Na effectively inhibited the formation of PhIP, Harman, and Norharman precursors and intermediates in smoked chicken drumsticks, which further confirmed the above inhibition mechanism of CMC-Na. These results could provide an effective approach to reduce HAA formation in smoked meat products by incorporating hydrocolloids. • XG and CMC-Na inhibit PhIP, Harman, and Norharman formation in chemical model system. • AG inhibit the formation of PhIP and Harman in chemical model system. • 2.0% CMC-Na is the most promising inhibitor of HAAs in smoked chicken drumsticks. • Hydrocolloids can inhibit HAAs by trapping their precursors and intermediates.

Inhibitory effects of 25 spices on heterocyclic aromatic amines formation in cooked pork patties

Inhibitory effects of 25 spices on heterocyclic aromatic amines formation in cooked pork patties

Application of High-Performance Liquid Chromatography with Fluorescence Detection for Non-Polar Heterocyclic Aromatic Amines and Acridine Derivatives Determination in Pork Loin Roasted in a Roasting Bag.

Heat treatment of meat can lead to the formation of carcinogenic organic compounds. The influence of dried fruits on the formation of non-polar heterocyclic aromatic amines (carbolines) and nitrogen derivatives of polycyclic aromatic hydrocarbons (azaarenes) in roasted pork loin was elucidated. Two hundred grams of fruit per 1 kg of meat were used as stuffing. Carbolines, derivatives of pyridoimidazole and pyridoindole, and azaarenes (benzoacridines and dibenzoacridines) were determined by means of high-performance liquid chromatography with fluorescence detection. The total concentration of six δ-, γ- and α-carbolines in roasted pork loin was 1.3 ng/g. This content decreased by 64%, 58%, and 54% in pork loin stuffed with prunes, apricots, and cranberries, respectively. Concentrations of β-carbolines (harmane and norharmane) increased under the influence of added fruits. The norharmane content increased the most, from 2.2 ng/g in the control sample to 12.3 ng/g in meat prepared with cranberries. The harmane content increased from 1.0 ng/g to 3.6 ng/g in meat with prunes. The total concentration of azaarenes (two benzoacridines and dibenzo[a,c]acridine), which was close to 0.1 ng/g, decreased in dishes with prunes and apricots by 54% and 12%, respectively. Azaarenes were not found in samples of meat stuffed with cranberries.

The Effects of the Marination Process with Different Vinegar Varieties on Various Quality Criteria and Heterocyclic Aromatic Amine Formation in Beef Steak

Herein, the effect of the dipping (static) marination process (at 4 °C for 2 h) with different types of vinegar (balsamic, pomegranate, apple, and grape) on various quality properties, including texture and protein profile of beef steaks and the formation of heterocyclic aromatic amines (HAAs) in beef steaks cooked on a hot plate (at 200 °C for 24 min), were determined. The results showed that 3.12–4.13% of the marinate liquids were absorbed by beef steak as a result of the marination process. No significant differences (p > 0.05) were observed between the marinated and cooked beef steaks in terms of water content, cooking loss, thiobarbituric acid reactive substances (TBARS) value, hardness, cohesiveness, and chewiness. However, significant differences were detected in terms of pH value and color values (L*, a*, and b*) (p < 0.01), and springiness, 2-amino-3,8-dimethylimidazo (4,5-f) quinoxaline (MeIQx) and total HAA content (p < 0.05). The marination with pomegranate vinegar resulted in the formation of darker steak, while a lighter one was obtained when apple vinegar was used in the marination. The use of balsamic and grape vinegar in the marination process decreased the springiness value compared to the control group. The myofibrillar proteins of beef steaks marinated with different types of vinegar generally showed a similar sodium dodecyl-sulfate polyacrylamide gel electrophoresis (SDS-PAGE) profile. However, some differences were observed in the band density of some proteins depending on the trial and the type of marination. In this study, of the nine examined HAAs, only two (2-amino-3-methylimidazo (4,5-f) quinoline (IQ) and MeIQx) could be detected and quantified. IQ was detected only in the control group steak (up to 0.51 ng/g), while MeIQx was detected in all treatment groups (up to 2.22 ng/g). The total HAA content varied between 0.59–2.22 ng/g. It was determined that the marination process with different vinegar types had different effects on the total HAA content of the steaks. Using balsamic and apple vinegar in the marination process decreased the total HAA content compared to the control group, but this decrease was not statistically significant (p > 0.05). On the other hand, using grape and pomegranate vinegar in the marination process increased the total HAA content, but this increase was only significant (p < 0.05) in the marination with pomegranate vinegar.

Effect of the fortification with astaxanthin on the quality parameters and heterocyclic amines content of meatballs

SummaryHerein, effects of astaxanthin usage on some quality parameters of meatballs and heterocyclic aromatic amines (HAAs) formation were investigated. The water content of meatballs with 1% of astaxanthin exhibited significantly (P &lt; 0.05) lower water content than other groups. The pH values of the samples were significantly (P &lt; 0.05) reduced due to astaxanthin addition; the higher the concentration used, the lower the pH value. Astaxanthin addition improved the oxidative stability and the colour properties of meatballs since the fortified samples exhibited significantly (P &lt; 0.05) lower thiobarbituric acid reactive substances and L* values and higher a* and b* values than the control samples in a non‐dose dependent manner. Only MeIQx was detected in meatballs cooked at 150 °C, the major compound in the other groups. The total HAAs content of meatballs ranged from 0.18 to 7.28 ng g−1, and it increased with increasing the cooking temperature. Astaxanthin addition inhibited or promoted HAAs formation depending on the cooking temperature. An increase (94–244%) in the total HAAs content was observed in the meatballs cooked at 150 °C, whereas a reduction of 47–54% in the total HAAs of those cooked at 200 °C was observed. Thus, astaxanthin could be recommended in producing of meatballs that will be cooked at 200 °C.

Propolis extract reduces heterocyclic aromatic amine formation in chicken thigh meat

ABSTRACT 1. The objective of the present study was to examine the effect of propolis extract on reducing the formation of carcinogenic/mutagenic heterocyclic aromatic amines (HAAs), thereby minimising dietary exposure in human consumers. 2. Chicken thigh meat samples were marinated with various concentrations (0%, 0.25%, 0.5% and 1%) of propolis extract, and cooked in a pan at 150°C or 200°C. Proximate composition, pH, lipid oxidation, creatine, creatinine content and twelve HAA levels of samples were analysed. 3. Varying levels of IQx (≤35.44 ng/g), MeIQx (≤0.58 ng/g), MeIQ (≤1.60 ng/g), 7,8-DiMeIQx (≤0.83 ng/g), 4,8-DiMeIQx (≤0.75 ng/g), Harman (≤5.54 ng/g), Trp-P-2 (≤1.77 ng/g), PhIP (≤1.61 ng/g) and AαC (≤0.93 ng/g) were quantified in control samples. Total HAA levels ranged between 2.83 and 47.26 ng/g across all samples. Propolis extract decreased the levels of total HAAs by 41.2–89.4% and 49.4–91.4% at 150°C and 200°C, respectively. 4. The results demonstrated that propolis extract marination might be an effective strategy to reduce the dietary exposure of HAAs via mitigating their formation in chicken thigh meat.

Reduction of heterocyclic aromatic amines formation in chicken thigh meat by Vaccinium myrtillus L. extract

This study aimed to examine the effects of Vaccinium myrtillus L. extract (VME) on the formation of heterocyclic aromatic amines (HAAs) in chicken thigh meat. Samples were marinated with different concentrations (0%, 0.25%, 0.5%, and 1%) of VME and cooked at 150 or 200°C in a pan. Twelve HAAs (IQ, IQx, MeIQ, MeIQx, 4,8-DiMeIQx, 7,8-DiMeIQx, Harman, Norharman, Trp-P-2, PhIP, AαC, and MeAαC) were analyzed, and total HAA levels ranged between 0.11 and 42.4 ng/g across all samples. A higher level of total HAAs was formed at higher cooking temperature, and the types and amounts of HAAs formed in the samples varied according to the temperature and the presence of VME. Reduction rate of VME on total HAA formation was 86.7%–99.3% and 50.5%–98.1% at 150 and 200°C, respectively. Moreover, VME reduced the lipid oxidation in chicken thigh meat. In conclusion, VME significantly mitigated the levels of HAAs in chicken samples. Practical Applications This study is the first to investigate the effects of Vaccinium myrtillus L. extract (VME) on the formation of heterocyclic aromatic amines (HAAs) in chicken meat. Formation of total and individual HAAs and lipid oxidation were effectively mitigated by VME marinades, and VME did not alter the organoleptic quality of chicken thigh meat according to the preliminary sensory evaluation. Therefore, this study suggests that marination with VME might be implicated to domestic and food service food preparation and cooking practices to reduce the formation and dietary intake of carcinogenic/mutagenic HAAs.

The Inhibitory Effect of Six Traditional Spices on the Formation of Heterocyclic Aromatic Amines in Fried Beef Patties

The Inhibitory Effect of Six Traditional Spices on the Formation of Heterocyclic Aromatic Amines in Fried Beef Patties

Study of meat content and frying process on the formation of polar heterocyclic aromatic amines in heated sausage samples: Optimization and method validation of three‐phase EME coupled with RP‐HPLC

Study of meat content and frying process on the formation of polar heterocyclic aromatic amines in heated sausage samples: Optimization and method validation of three‐phase <scp>EME</scp> coupled with <scp>RP‐HPLC</scp>

Cyanidin and rutin inhibit the formation of heterocyclic aromatic amines in chemical modeling systems and smoked chicken drumsticks

This study aims to evaluate the heterocyclic aromatic amine (HAA) formation inhibited by cyanidin and rutin in chemical modeling systems and smoked chicken drumsticks. In the PhIP and β-carboline chemical modeling systems, cyanidin inhibited the PhIP, Harman, and Norharman formation while rutin inhibited the PhIP formation but promoted the Harman and Norharman formation compared with control sample (P < 0.05). A mechanistic investigation confirmed that inhibiting the PhIP formation by cyanidin was mainly through trapping phenylalanine, creatine, creatinine, glucose, phenylacetaldehyde, and an aldol condensation product. In the smoked chicken drumsticks, cyanidin inhibited the PhIP, Harman, and Norharman formation dose-dependently compared to the control sample (P < 0.05), with 2.0 % (w/v) cyanidin having the highest inhibitory effect. Moreover, cyanidin inhibited the formation of PhIP precursors and intermediates in the smoked chicken drumsticks. These results provide evidence for using phenolic compounds to reduce HAA formation in smoked meat products.

Sucuk Örneklerinin Heterosiklik Aromatik Amin İçeriğine Pişme Yönteminin Etkisi

In this study, we aimed to find the influence of different levels of doneness (rare, medium, over-cooked) on the formation of heterocyclic aromatic amines (HCAs) in Turkish fermented beef sausages (sucuk) cooked by pan-frying method. Six types of HCAs were determined at three different temperatures. Determination of HCA was made using a high performance liquid chromatography (HPLC). IQ, MeIQx and 4,8-DiMeIQx were detected and quantified with DAD detector and PhIP, norharman and harman were determined with fluorescence detector. External standard and recovery methods were both used for the calculation amount of HCAs to obtain results that are more accurate. HCA and soluble protein analyses were performed in rare, medium and over-cooked sucuk samples. Moisture, ash, protein, lipid contents and pH analyses were performed in raw sucuk samples. Total HCA content of sucuk samples was found between 0.65 and 17.90 ng/g. Total HCA content of over-cooked sucuk samples were higher than rare-cooked sucuk samples (P

Formation of heterocyclic aromatic amines in grilled pork depending on the pre-thermal treatment method

Electric grilled pork pretreated using four methods was analyzed for heterocyclic aromatic amines: 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline (MeIQx) and 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP). It was found that pre-thermal treatment of pork led to both a decrease and an increase in the content of heterocyclic aromatic amines in grilled steaks. In contrast to the control sample, the sample pretreated with an oil-based marinade exhibited a 3.2-fold decrease in the amount of MeIQx and 4.82-fold decrease in the amount of PhIP. The sample pretreated with a water-based marinade exhibited a 1.75-fold decrease in the amount of PhIP and a 3.81-fold increase in the amount of MeIQx. The sample pretreated with a dry curing mixture with red hot pepper exhibited a 3.5-fold increase in the amount of MeIQx and a 2.44-fold increase in the amount of PhIP. The sample pretreated with a dry curing mixture with paprika showed a 8.21-fold increase in the amount of MeIQx and a 3.65-fold increase in the amount of PhIP compared to the control sample. The study has shown that pretreatment of meat leads to both an increase and a decrease in the amount of heterocyclic aromatic amines formed during high-temperature thermal treatment depending on the non-meat ingredients used.

Effect of tea polyphenols on the inhibition of heterocyclic aromatic amines in grilled mutton patties

The inhibitory effects of tea polyphenols (TP) on heterocyclic aromatic amine (HAA) formation in grilled mutton patties at two temperatures (220 and 250°C) were investigated. TP at all the application levels (0.03%–0.5%) significantly increased antioxidant potential of patty samples. At a 0.5% application level, TP reduced the generation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-1-methyl-6-phenylimidazo[4,5b] pyridine (PhIP), and 2-amino-3,4,8-trimethylimidazo[4,5-f]-quinoxaline (4,8-DiMeIQx) at 220°C by 16.7%, 64.7%, and 31.1% (p < .05), respectively. However, at lower TP concentrations (0.03%–0.3%) or at 250°C, higher amounts of HAAs were detected in grilled meat, indicating a complex chemical, temperature-dependent behavior of phenolic compounds. The results suggest that TP at a 0.5% level was a strong antioxidant to mitigate HAA formation in grilled mutton patties at 220°C, but TP was promotive of HAA production under other conditions. Novelty impact statement Heterocyclic aromatic amines formation in grilled mutton patties at 220°C but not at 250°C was significantly inhibited by 0.5% tea polyphenols. The inhibition level reached up to 31% for MeIQx, PhIP, and 4,8-DiMeIQx, which was correlated to phenolic radical scavenging activity. The finding indicates the potential to improve food safety of grilled mutton patties by antioxidative tea extract.

The Effects of Cooking Temperatures and Times on the Formation of Aromatic Amines of Meatballs Derived from Sivas Province

In this study, nine different experimental groups were prepared by cooking meatball samples 5, for 7,5 and 10 minutes at 150, 200 and 250 ℃. Some chemical analysis including fat, protein, thiobarbituric acid contents and pH were applied to samples. The amount of Heterocyclic Aromatic Amines (HAA) of the samples treated byheat at 250 ℃ for 7,5 minutes had highest value, 0.42 ng/g. IQ (2-amino-3-metilimidazo[4,5-f]kinolin) and PhIP (2-amino-1-metil-6-fenilimidazo[4,5-b] piridin) were detected for the samples subjected to 250 ℃ heat treatment. HAA was not detected in the samples cooked at 7,5 for 10 minutes and 200 ℃, whereas MeQIx was found to be 0.17 ng/g for the samples baked for 5 minutes. Consequently, it was detected that the amount of HAA in all groups was below the 1 ng/g. which makespossible to comment chosen parameters for cooking meatballs is appropriate for formation of HAA.

Changes in flavor, heterocyclic aromatic amines, and quality characteristics of roasted chicken drumsticks at different processing stages

This study evaluated changes in flavor, heterocyclic aromatic amines (HAAs), and quality characteristics of roasted chicken drumsticks at three different processing stages: marinating (MS), low-temperature roasting (LRS), and high-temperature roasting (HRS). Raw chicken drumsticks (RC) served as the control. Water content and L*-value were significantly highest (P < 0.05), whereas a*-value and b*-value were significantly lowest (P < 0.05) in the HRS sample. Furthermore, the HRS sample had a significantly higher (P < 0.05) pH value than the RC, MS, and LRS samples. A total of 48 different volatile compounds were detected and electronic nose results indicated similar odor profiles between the MS and LRS samples. The LRS and HRS samples had significantly higher (P < 0.05) contents of PhIP, Harman, and Norharman than the RC and MS samples, which can be explained by the higher contents of precursors phenylalanine, tryptophan, and creatinine in the LRS and HRS samples compared to those in the RC and MS samples. Correlation analysis result indicated that the aldehydes and ketones are responsible for the PhIP, Harman, and Norharman formation. These results provide guidance for revealing the flavor and HAA formation of roasted chicken during processing.

Inhibitory effects of carob and propolis extracts on the formation of heterocyclic aromatic amines in beef meatballs cooked with different methods

The aim of this study was to evaluate the inhibitory effects of propolis extract (PE) and carob extract (CE) on the formation of heterocyclic aromatic amines (HCAs) in beef meatballs cooked by pan-frying and oven methods. All samples were cooked at 150°C, 200°C and 250°C. 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,8-dimethylimidazo[4,5-]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), 1-methyl-9Hpyrido[4,3-b]indole (harman) and 9H-pyrido[4,3b]indole (norharman) were detected and quantified by high performance liquid chromatography (HPLC). CE had the highest inhibition effect on total HCA content. The inhibitory effects of CE and PE at 1% and 2% concentrations on total HCAs levels were found to be 43.27-85.57% and 27.36-82.00% in cooked meatballs, respectively. HCA amounts in meatballs generally increased by increasing cooking temperature. In particular, the inhibitory effect on HCAs related with the antioxidant activity of extracts. Our results indicated that PE and CE might be used as a natural food additive for reducing HCAs in meatballs.

Effect of woodchip types on heterocyclic aromatic amine formation and quality characteristics of smoked bacon

The impact of different woodchips (beech, oak, pear, and apple) on the contents of heterocyclic aromatic amines (HAAs) and quality characteristics of smoked bacon was investigated. The results indicated that the contents of total HAAs and non-polar HAAs in beech- and oak-smoked bacon were lower than that in pear- and apple-smoked bacon (P < 0.05). There were no HAAs detectable in control (non-smoking) sample. The smoking process promoted the formation of free amino acids (FAA) in the smoked bacon. The total contents of FAA in beech- and oak-smoked bacon were higher than these in the pear- and apple-smoked bacons (P < 0.05). The beech-smoked bacon had the highest L*-value (P < 0.05), and oak-smoked bacon had the lowest thiobarbituric acid-reactive substance (TBARS) value and carbonyl content (P < 0.05). Additionally, woodchip types had no significant influence on a*-value, b*-value, moisture content, aw, T20, T21 and T22 (P > 0.05). PCA of the HAA contents and quality characteristics could effectively differentiate that were unsmoked and smoked bacon. Therefore, woodchip types had a great influence on HAA contents and quality of smoked bacon.

Influence of different ratios of sucrose and green tea leaves on heterocyclic aromatic amine formation and quality characteristics of smoked chicken drumsticks

This study evaluated the heterocyclic aromatic amine (HAA) content in chicken drumsticks smoked with different ratios of sucrose and green tea leaves (GT). The results revealed that water content was similar in all treatments ( P > 0.05). The samples smoked with combined sucrose and GT showed significantly lower pH, L *-value, and b *-value than the control sample (smoked with sucrose only ( P < 0.05), and color parameters L *-value and a *-value decreased and increased, respectively, as the proportion of GT increased ( P < 0.05). Sensory evaluation results indicated that smoking with a high proportion of GT led to higher color and smoky scores than the other smoked samples ( P < 0.05). The levels of IQx, 7,8-DiMeIQx, 4,8-DiMeIQx, PhIP, AαC, MeAαC in low GT sample were 2.99, 4.21, 1.69, 13.58, 1.93, 8.00 ng/g, respectively, which were significantly higher than those in the other samples ( P < 0.05). The levels of Harman and Norharman significantly increased from 5.76 ng/g to 18.88 ng/g and from 43.15 ng/g to 128.46 ng/g, respectively, with the increase in ratio of GT ( P < 0.05). The contents of apolar HAAs and total HAAs significantly increased from 59.81 ng/g to 150.12 ng/g and from 84.96 ng/g to 160.71 ng/g, respectively, as the proportion of GT increased. Overall, the chicken drumsticks smoked with combined sucrose and GT have an improved sensory profile but increased HAA content. Therefore, a low ratio of GT to sucrose may be more appropriate for smoked chicken. • Sample smoked with high proportion of GT received highest color and smoky scores. • The polar HAAs first increased and then decreased as the proportion of GT increased. • The apolar HAAs and total HAAs increased with the increased proportion of GT. • The free amino acids, creatine, and glucose were related to the HAA formation.

Comparison of the reducing effects of blueberry and propolis extracts on heterocyclic aromatic amines formation in pan fried beef

This study was aimed to examine the effects of natural antioxidant-based marinades on the formation of heterocyclic aromatic amines (HAAs) in cooked beef. Samples were marinated overnight with different concentrations (0, 0.25, 0.5 and 1%) of blueberry or propolis extracts, and pan fried at 150 and 200 °C for a total of 10 min. Individual and total HAAs were detected at different levels according to the cooking temperature, extract type and concentration. Total HAA levels increased as the cooking temperature increased (P < 0.01), and ranged from non detectable levels to 38.27 ng/g across all samples analysed. Mitigation up to 61.2% and 100% in total HAA levels were achieved by propolis and blueberry extracts, respectively. The inhibitory effects of blueberry extract on total HAAs formation were significantly higher than propolis extract (P < 0.01). Thereby, this study showed that natural antioxidant-based marinades containing blueberry and propolis extracts had mitigating effects on HAAs formation in beef samples pan-fried at 150 and 200 °C.