Heterocyclic Aromatic Amines Content Research Articles

Theoretical exploration of the phenolic compounds’ inhibition mechanism of heterocyclic aromatic amines in roasted beef patties by density functional theory

The ability of spices (bay leaf, star anise, and red pepper) and their characteristic phenolic compounds (quercetin, kaempferol, and capsaicin) to inhibit Heterocyclic aromatic amines (HAAs) in roasted beef patties were compared. Density functional theory (DFT) was used to reveal phenolic compounds interacting with HAAs-related intermediates and free radicals to explore possible inhibitory mechanisms for HAAs. 3 % red chili and 0.03 % capsaicin reduced the total HAAs content by 57.09 % and 68.79 %, respectively. DFT demonstrated that this was due to the stronger interaction between capsaicin and the β-carboline HAAs intermediate (Ebind = –32.95 kcal/mol). The interaction between quercetin and phenylacetaldehyde was found to be the strongest (Ebind = −17.47 kcal/mol). Additionally, DFT indicated that capsaicin reduced the carbonyl content by transferring hydrogen atoms (HAT) to eliminate HO·, HOO·, and carbon-centered alkyl radicals. This study provided a reference for the development of DFT in the control of HAAs.

Comparing application methods of reishi mushroom (Ganoderma lucidum) extract in deep-fried meatballs: impact on heterocyclic aromatic amine formation.

The present research was conducted to investigate the impact of reishi mushroom extract (RME) on the formation of heterocyclic aromatic amines (HAAs) in meatballs. Sample preparations involved applying RME using either the spreading or addition method, with varying concentrations (0%, 0.25%, 0.5%, and 1% of RME), followed by deep-frying at temperatures of 150 and 190 °C for 3 min. The types and levels of HAAs varied based on the frying temperature, method of extract application, and the extract concentration. Notably, total HAA contents increased with rising the frying temperature (P < 0.01) and varied from undetectable levels to 4.91 ng g-1 across all analyzed meatballs. The addition method was more effective than the spreading method (P < 0.01), and among the concentrations tested 0.25% RME exhibited the highest efficacy in reducing total HAAs (P < 0.05). Furthermore, the addition method inhibited lipid oxidation more efficiently compared to the surface spreading method (P < 0.05). This study demonstrated that RME had mitigating effects on HAAs depending on the concentration and frying conditions in deep-fried meatball samples. © 2024 Society of Chemical Industry.

Effect of simultaneous application of antioxidants in oil and in chicken on heterocyclic aromatic amine formation in deep-fat fried chicken breast

This study aimed to estimate the effects of simultaneous application of antioxidants in meat and in oil on heterocyclic aromatic amine (HAA) formation in fried chicken during 40 deep-fat frying cycles. The experiment was carried out by adding Adinandra nitida leaf extract (ANE) (200 mg/100 g) to chicken while adding tea polyphenols (TP) (40 mg/100 g), sesamol (SL) (40 mg/100 g), or rosemary extract (RE) (40 mg/100 g) to soybean oil. It was found that the addition of TP, SL or RE in oil reduced the lipid oxidation and the formation of total HAAs in meats. Adding ANE alone to meat reduced total HAA contents in meats by 11.98%–38.00%; simultaneously adding TP, SL or RE to oil reduced total HAA contents in meats by 33.98%–61.46%, 15.86%–44.94%, and 25.22%–48.01%, respectively, during 40 frying cycles. Pearson correlation analysis revealed significant correlations (all absolute values of correlation coefficients > 0.53) between HAA formation and oxidation indices. This research supplies evidence that adding antioxidants to both meat and oil inhibits HAA formation during deep-fat frying.

Impact of Cumin (Cuminum cyminum) Incorporation on the Generation of Heterocyclic Aromatic Amines in Meatballs

In the current study, the impacts of using cumin (0.5% and 1%, w/w) in beef meatballs on heterocyclic aromatic amines (HAAs) formation and some quality characteristics when cooked at 150 and 250 °C were investigated. It was found that using of cumin at different ratios in beef meatballs showed a significant (p &lt; 0.01) effect on pH, thiobarbituric acid reactive (TBARS) value, and total HAA. The cooking process significantly (p &lt; 0.01) affected the meatballs’ water content, pH, and TBARS values, while the cooking loss and total HAA content of meatballs were significantly (p &lt; 0.01) affected by cooking temperature. It was found that the cumin usage rate in meatballs increased the pH value, while it was found to decrease the TBARS value. As expected, the cooking process was associated with a reduction in water, while it was found to result in an increase in the pH and TBARS values. On the other hand, both cooking temperature and cumin addition to meatballs led to an increase in their total HAA content. Diverse samples exhibited detectable levels of IQx, MeIQx, MeIQ, and PhIP compounds. The presence of MeIQx compound was found in all samples, except for the control group cooked at 150 °C. Additionally, the use of 0.5% and 1% cumin in meatballs cooked at temperature of 250 °C had an inhibitory effect on MeIQx compound. Our results revealed that the incorporation of cumin in the meatballs resulted in an increase in the total HAA content, likely due to its prooxidant effect. However, it was found that the use of cumin at certain rates could reduce the formation of MeIQx compound with an antioxidant effect. However, in this study found that even if 100 g of meatballs with the highest concentration of total HAA were consumed, the maximum HAA exposure limit value (0–15 µg/day) was not exceeded.

Effects of volatile organic compounds of smoke from different woods on the heterocyclic amine formation and quality changes in pork patty

This study investigated the effects of smoke derived from cypress (CY), mulberry (MU), metasequoia (ME), pine (PI), and camphor (CA) on the heterocyclic aromatic amines (HAs), flavor, and sensory attributes of smoked pork patty. The results showed that the smoke derived from the five kinds of wood and the flavor of the corresponding smoked meat were classified into three types. Moreover, the smoke of CY and PI, and the smoke of MU and ME can be classified into one category respectively, which significantly improved the flavor of the smoked meat. Both free and protein-bound HAs were detected in smoked meat, while the smoking process significantly increased the HAs content, especially free Norharman (3.26 ng/g in control meat, and 82.24 ng/g in meat smoked with CY). Correlation analysis showed that various volatile organic compounds (VOCs) and HAs were closely associated. Future research should pay attention to the VOCs in smoked meat including vanillin, Close attention should be paid to tridecane and crotonic acid, as well as tetradecane and α-Dehydro-ar-himachalene in smoke, which were consistently correlated with various HAs and may participate in HAs formation. These results may reveal how the smoking process influences the formation of HAs and which factors should be targeted to inhibit HAs in smoked meat products.

Evaluation of Chinese Prickly Ash and Cinnamon to Mitigate Heterocyclic Aromatic Amines in Superheated Steam-Light Wave Roasted Lamb Meat Patties Using QuEChERS Method Coupled with UPLC-MS/MS

Chinese prickly ash and cinnamon contain many antioxidants, which scavenge free radicals and can reduce many harmful compounds, such as heterocyclic aromatic amines (HAAs). Modern technologies used for cooking, such as the use of superheated steam roasting, are beneficial in decreasing the development of HAAs. The current study was based on the use of these two spices in roasted lamb patties to mitigate the formation of HAAs in superheated steam roasted patties. Results exhibited significant differences (p &lt; 0.05) in the content of both polar and non-polar HAAs as compared to control patties. In cinnamon roasted patties, polar HAAs were reduced from 23.76 to 10.56 ng g−1, and non-polar HAAs were reduced from 21.34 to 15.47 ng g−1. In Chinese prickly ash patties, polar and non-polar HAAs were 43.60 ng g−1 and 35.74 ng g−1, respectively. Similarly, cinnamon-treated patties showed a significantly higher (p &lt; 0.05) reduction in polar HAAs (23.52 to 12.41 ng g−1) than non-polar (16.08 to 9.51 ng g−1) at concentrations of 0.5–1.5%, respectively, as compared to the control, with 45.81 ng g−1 polar and 35.09 ng g−1 non-polar HAAs. The polar HAAs tested were PhIP, DMIP, IQx, and 8-MeIQx, while the non-polar were harman and norharman. Both spices and superheated steam controlled HAAs to a significant level in lamb meat patties.

Enhancing effect of chia seeds on heterocyclic amine generation in meatball

SummaryThe impact of using chia seeds at different rates (0%, 0.5%, 1%, and 1.5%) in meatball on the water content, pH and lipid oxidation (thiobarbituric acid reactive substances, TBARS), cooking loss and heterocyclic aromatic amines (HAAs) content of meatballs cooked at 150, 200, and 250 °C was investigated. The chia seed significantly affected water content (P &lt; 0.01), cooking loss (P &lt; 0.05), pH (P &lt; 0.05) and total HAAs content (P &lt; 0.01), whereas no significant impact (P &gt; 0.05) was detected on TBARS value. With cooking, water content decreased (P &lt; 0.01), while the pH and TBARS values increased (P &lt; 0.01). Cooking temperatures significantly affected (P &lt; 0.01) the water content, cooking loss and total HAAs content. The content of total HAAs of the meatballs increased with increasing the cooking temperature. The results illustrated that IQ, 7,8‐DiMeIQx, 4,8‐DiMeIQx, AαC and MeAαC were below the detectable limit (&lt;LOD) in all samples, while MeIQx was the dominant compound among the detected HAAs compounds. The research indicated that the use of chia seeds increased the total HAA content, and the highest level was found in meatballs prepared with 1% chia seeds.

Heterocyclic aromatic amines in spiced pork shoulder: content analysis and effects of soy sauce, cooking wine and sugar

SummarySpiced pork shoulder is a traditional Chinese meat product that is loved by consumers. However, heterocyclic aromatic amines (HAAs) formed by spiced pork shoulder during processing endanger human health. The present study determined the HAA contents of seven kinds of spiced pork shoulder, and examined the effects of soy sauce, cooking wine and sugar on the formation of HAAs. The total HAAs of the seven samples were between 0.10 ng/g and 56.82 ng/g. There were Harman (0.03–39.77 ng/g) and Norharman (0.06–18.76 ng/g) correlations in all samples. Not all samples had higher HAAs levels in the skin than the whole shoulder. Creatine and creatinine were more actively involved in the formation of HAAs than glucose. Soy sauce contributed the most to the formation of HAAs, followed by cooking wine and sugar. Compared to spiced pork shoulder, the soup contained more HAAs. Exogenous contamination of HAAs in soy sauce, cooking wine and soup was an important source of HAAs in spiced pork shoulder.

Content of heterocyclic aromatic amines and D-enantiomers of amino acids in sausage products

Content of heterocyclic aromatic amines and D-enantiomers of amino acids in sausage products

Critical steps in the production of oil from oilseed to reduce heterocyclic aromatic amines

Abstract Contamination by the heterocyclic aromatic amines (HAAs) norharman and harman is one of the risks in vegetable oil production, so oil producers strive to decrease their content in the end products. In this study, the effects of production conditions—specifically, two pretreatment methods (roasting and microwaving), four extraction methods (two pressing and two solvent extraction) and adsorption refining (four absorbents)—of five oils (flaxseed, peanut, rapeseed, sesame, and sunflower seed) were evaluated. The results showed that microwaving as a pretreatment produced significantly fewer HAAs than roasting (P&amp;lt;0.05). After two pretreatments, the HAA content of oils was ranked from high to low as follows: sunflower oil, sesame oil, flaxseed oil, rapeseed oil, and peanut oil. Solvent-extracted oils (9.16–316.73 µg/kg) had fewer HAAs than pressed oils (26.61–633.93 µg/kg). Using adsorbents reduced HAAs in oils from the initial 21.77–484.22 to 0.31–41.58 µg/kg, and the removal rate reached 99.28%. This study provides critical HAA reduction strategies for application in the oil production process to obtain safe final products.

Assessment of heterocyclic aromatic amines contents in flamed and braised chicken in Burkina Faso.

The nutritional status of meat is tarnished by its association with the induced cooking contaminants. The aim of this study was to assess the heterocyclic aromatic amines profile and contents in processed chicken in Burkina Faso. Eight polar and apolar heterocyclic aromatic amines (HAAs) including 2-mino-3-methylimidazo[4,5-f]quinolone (IQ), 3-amino-1,4-dimethyl-5H-pyrido[4, 3-b]indole (Trp-P1), 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P2), 2-mino-9H-pyrido-[2,3-b]indole (AαC), 2-amino-1-methyl-6-phenylimidazo[4, 5- ]pyridine (PhIP), 2-amino-3-methyl-9H-pyrido[2,3-b] indole (MeAαC), 2-amino-3,4,8-rimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx) and 2-amino-3,8-imethylimidazo[4,5-]quinoxaline (MeIQx) were screened by high performance liquid chromatography from 29 samples of flamed chicken and 66 samples of braised chicken collected in Ouagadougou city. Apolar HAAs and polar HAAs were respectively 12 and 3 times more abundant in flamed chickens (32.66±10 and 3.48±10.39 ng/g, respectively) than in braised chickens (2.70±9.67 and 0.92 ng/g, respectively). The maximum levels of AαC were in the same proportions in flamed (12.01 ng/g) and braised chickens (14.13 ng/g). Flamed chicken had the highest Trp-P1 content (530.31 ng/g). The 4,8-DiMeIQx was not detected in braised chicken. The AαCs were more abundant in flamed than in braised chicken. The profile and the contents of the HAAs in processed chicken are related to cooking methods. Because of the high variability observed on the obtained concentrations, investigations on the contents of precursors in raw chicken, the effect of marinating ingredients on the formation of HAAs are needed.

Understanding the Development of Heterocyclic Aromatic Amines in Fried Bacon and in the Remaining Oil after Pan-Frying in Five Different Vegetable Oils.

The physicochemical properties of five vegetable oils (peanut, corn, rapeseed, sunflower seed, and soybean) and their impact on the development of heterocyclic aromatic amines (HAAs) in pan-fried bacon and in the remaining oil were investigated. Corn oil led to the lowest total free amino acids (FAAs) contents and glucose content of fried bacon (p < 0.05) and rapeseed oil led to the lowest creatine content of fried bacon (p < 0.05). Bacon fried in corn oil had the highest HAA contents (p < 0.05). The total HAA contents of the oils after frying were lowest in rapeseed and soybean oils (p < 0.05). The type of vegetable oil used affected the color of the fried bacon but not the flavor and taste (p < 0.05). To reduce the HAA concentrations of fried bacon, the type of vegetable oil should be considered.

Heterocyclic aromatic amines in roasted chicken: Formation and prediction based on heating temperature and time

The effects of chicken roasting temperature and time on the production of heterocyclic aromatic amines (HAAs) were investigated and an HAA prediction model based on heating conditions was established. Generally, the HAA content was significantly affected by the heating conditions in the roast chicken. Transportation of precursors from meat to skin, exposure of skin to high temperatures, and fat oxidation in the skin may result in higher HAAs than meat. Principal component analysis (PCA) showed that the effect of relatively high temperatures and long roasting times on HAAs was stronger than that of lower temperatures and shorter roasting times. In the prediction of HAA production, all regression correlation coefficient (R) values were close to one. The errors of 15 samples of experimental and predictive data were close to zero. Based on the results, backpropagation-artificial neural network (BP-ANN) has a high potential for predicting the production of HAAs under heating conditions.

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.

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 Carcinogens in Processed Meat and Its Measurement with the Usage of Artificial Digestion-A Review.

Meat is a rich source of various nutrients. However, it needs processing before consumption, what in turn generates formation of carcinogenic compounds, i.a., polycyclic aromatic hydrocarbons (PAH), nitrosamines (NOCs), and the most mutagenic heterocyclic aromatic amines (HAAs). It was widely found that many factors affect the content of carcinogens in processed meat. However, it has recently been discovered that after digestion free HAAs are released, which are not detectable before enzymatic treatment. It was established that the highest percentage of carcinogens is released in the small intestine and that its amount can be increased up to 6.6-fold. The change in free HAAs content in analyzed samples was dependent on many factors such as meat type, doneness, particle size of meat, and the enzyme concentration used for digestion. In turn, introduction of bacteria naturally occurring in the human digestive tract into the model significantly decreases total amount of HAAs. Contrary, the addition of food ingredients rich in polyphenols, fiber, and water (pepper powder, onions, apples) increases free HAAs’ release up to 56.06%. Results suggests that in vitro digestion should be an integral step of sample preparation. Artificial digestion introduced before chromatographic analysis will allow to estimate accurately the content of carcinogens in processed meat.

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.

Formation of volatile flavor compounds, maillard reaction products and potentially hazard substance in China stir-frying beef sao zi

The effects of stir-frying stages on the formation of flavor volatile compounds, Maillard reaction products (MRPs) and potentially hazardous substances with time in stir-fried beef sao zi were investigated. A total of 122 volatile compounds were identified in beef sao zi after stir-frying. Most of the volatile compounds were produced in the stir-frying fat (SFF) process of beef sao zi. Furosine, fluorescence intensity, Nε-(1-Carboxymethyl)-L-lysine (CML), Nε-(1-Carboxyethyl)-L-lysine (CEL) polyaromatic hydrocarbons (PAHs), heterocyclic aromatic amines (HAAs) and acrylamides (AA) are mainly presented in stir-fried beef sao zi. The furosine peaked at MSF 120 s as the Maillard reaction progressed. The fluorescent compound gradually increased with time during the stir-frying process. The CML and CEL peaked at MSF 120 s. AA reached its maximum in MSF 90 s and then decreased. The quantities and content of HAAs and PAHs were increased by prolonging the stir-frying time, but ended up far lower than the maximum permissible value specified by the Commission of the European Communities. The extended stir-frying promoted MRPs and some hazardous substances, but the content of potentially hazardous substances was still within the safety range for stir-frying beef sao zi.

Heterocyclic aromatic amine contents and quality characteristics of bacon as influenced by NaCl concentration of brine.

Bacon usually have a high salt content. Excessive intake of salt could cause a harm to human health. Heterocyclic aromatic amines (HAAs) are carcinogenic and mutagenic heterocyclic compounds formed by the reactions of precursor substances at high temperature. This study investigated the influence of different levels of NaCl on the HAA contents and quality characteristics of bacon. Moisture, aw , L* value, b* value, thiobarbituric acid-reactive substance (TBARS), and carbonyl content increased significantly with a decrease in the NaCl concentration of the brine (p<0.05). There were no significant differences between treatments for a* value, pH, creatine content, sensory redness, bitterness, or off-odor (p>0.05). Sensory evaluation showed that saltiness in bacon increased significantly with increased NaCl concentrations in brine. The increased NaCl concentrations decreased the total HAAs in fried bacon (p<0.05). Moreover, the nonpolar HAA contents in bacon were higher than the polar HAA contents; salt concentration mainly affected the nonpolar HAA content. In summary, salt content had a significant influence on the HAA content and the quality characteristic of bacon.