Formation Of Heterocyclic Aromatic Amines Research Articles

Exploration of the prediction and generation patterns of heterocyclic aromatic amines in roast beef based on Genetic Algorithm combined with Support Vector Regression

Heterocyclic aromatic amines (HAAs) are harmful byproducts in food heating. Therefore, exploring the prediction and generation patterns of HAAs is of great significance. In this study, genetic algorithm (GA) and support vector regression (SVR) are used to establish a prediction model of HAAs based on heating conditions, reveal the influence of heating temperature and time on the precursor and formation of HAAs in roast beef, and study the formation rules of HAAs under different processing conditions. Principal component analysis (PCA) showed that the effect on HAAs generation increases with the increase of heating temperature and time. The GA-SVR model exhibited near-zero absolute errors and regression correlation coefficients (R) close to 1 when predicting HAAs contents. The GA-SVR model can be applied for real-time monitoring of HAAs in grilled beef, providing technical support for controlling hazardous substances and intelligent processing of heat-processed meat products.

Effect of air-frying on formation and correlations of polycyclic aromatic hydrocarbons, acrylamide, and heterocyclic aromatic amines in foods and risk assessment.

The online version contains supplementary material available at 10.1007/s10068-024-01639-4.

Effect of free and bound proanthocyanidins from Chinese quince on heterocyclic aromatic amine formation and quality in fried chicken.

The abilities of Chinese quince free proanthocyanidins (FP) and bound proanthocyanidins (BP) at different levels (0.1%, 0.15%, and 0.3%) to mitigate heterocyclic aromatic amine (HAA) formation in fried chicken patties were investigated for the first time and compared with vitamin C (Vc). FP and BP reduced HAAs in a dose-dependent manner. Significantly, high concentrations of FP (0.3%) resulted in a reduction of PhIP, harman, and norharman levels by 59.84%, 22.91%, and 38.21%, respectively, in chicken patties. The addition of proanthocyanidins significantly (p<0.05) reduced the weight loss of fried chicken patties. Furthermore, a positive correlation was observed among pH, weight loss, and total HAA formation in all three groups (FP, BP, and Vc). Multivariate analysis showed that FP had a more pronounced effect than BP from the perspective of enhancing the quality of fried chicken patties and reducing the formation of HAAs. These results indicate that proanthocyanidins, both BP and FP, but especially FP, from Chinese quince can inhibit the formation of carcinogenic HAAs when added to protein-rich foods that are subsequently fried.

Effects of Lipid on the Formation of Heterocyclic Aromatic Amines and Advanced Glycation End Products in Thermally Processed Fish

ABSTRACT The formation of hazardous substances, heterocyclic aromatic amines (HAAs) and two representative advanced glycation end products (AGEs), Nε-carboxymethyl-lysine (CML) and Nε-carboxyethyl-lysine (CEL) in five kinds of fish with different fat contents during thermal processing was investigated. The results indicated that HAAs, AGEs produced is related to the lipids in varying degrees. The variation of key precursors were examined to explain the relationship between fat oxidation and molecular pathway of HAAs and AGEs formation. The current research may help us better understand the overall generation of hazardous substances in food systems, and provide new ideas for formulating prevention in future production.

Bitter melon extract mitigates heterocyclic aromatic amine formation in chicken thigh meat.

The purpose of the present research was to study the impact of bitter melon extract (BME) on the generation of heterocyclic aromatic amines (HAAs) in chicken thigh meat. Raw chicken samples were marinated overnight with various levels (0%, 0.5%, and 1%) of BME, and pan-fried at 150, 200, and 250°C for a total of 10 min. IQx, IQ, MeIQx, MeIQ, 7,8-DiMeIQx, 4,8-DiMeIQx, PhIP, AαC, and MeAαC were detected in quantities that varied according to the cooking temperature and the concentration of BME. Notably, IQx, MeIQx, MeIQ, 7,8-DiMeIQx, 4,8-DiMeIQx, and AαC levels were reduced through the application of the marinade. Cooking at higher temperatures led to elevated levels of total HAAs. Total HAA levels were 0.98 ± 1.12 ng/g, 3.82 ± 2.12 ng/g, and 6.25 ± 3.35 ng/g in samples cooked at 150, 200, and 250°C, respectively (p < .01). BME demonstrated its effectiveness in mitigating total HAA levels, showing reductions ranging from 25.9% to 69.9%. The most effective concentration of BME in reducing total HAAs was 1% for all cooking temperatures, which might be attributed to its antioxidant activity. These results carry substantial implications for potentially incorporating natural extracts such as BME into chicken products as a viable strategy to reduce HAAs, thus enhancing the safety and quality of meat products.

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 The Author(s). Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

Unveiling heterocyclic aromatic amines (HAAs) in thermally processed meat products: Formation, toxicity, and strategies for reduction - A comprehensive review.

This comprehensive review focuses on heterocyclic aromatic amines (HAAs), a class of chemicals that commonly form during the cooking or processing of protein-rich foods. The International Agency for Research on Cancer (IARC) has categorized certain HAAs as probable human carcinogens, highlighting the significance of studying their formation and control in food safety research. The main objective of this review is to address the knowledge gaps regarding HAAs formation and propose approaches to reduce their potential toxicity during thermal processing. By summarizing the mechanisms involved in HAAs formation and inhibition, the review encompasses both conventional and recent detection methods. Furthermore, it explores the distribution of HAAs in thermally processed meats prepared through various cooking techniques and examines their relative toxicity. Additionally, considering that the Maillard reaction, responsible for HAAs formation, also contributes to the unique flavors and aromas of cooked meat products, this review investigates the potential effects of inhibiting HAAs formation on flavor substances. A thorough understanding of these complex interactions provides a foundation for developing targeted interventions to minimize the formation of HAAs and other harmful compounds during food processing.

Marinades Based on Natural Ingredients as a Way to Improve the Quality and Shelf Life of Meat: A Review.

Marinating is a traditional method of improving the quality of meat, but it has been modified in response to consumer demand for "clean label" products. The aim of this review is to present scientific literature on the natural ingredients contained in marinades, the parameters of the marinating process, and certain mechanisms that bring about changes in meat. A review was carried out of publications from 2000 to 2023 available in Web of Science on the natural ingredients of meat marinades: fruit and vegetables, seasonings, fermented dairy products, wine, and beer. The review showed that natural marinades improve the sensory quality of meat and its culinary properties; they also extend its shelf life. They affect the safety of meat products by limiting the oxidation of fats and proteins. They also reduce biogenic amines and the formation of heterocyclic aromatic amines (HAAs) and polycyclic aromatic hydrocarbons (PAHs). This is possible due to the presence of biologically active substances and competitive microflora from dairy products. However, some marinades, especially those that are acidic, cause a slightly acidic flavour and an unfavourable colour change. Natural compounds in the ingredients of marinades are accepted by consumers. There are no results in the literature on the impact of natural marinades on the nutritional value and health-promoting potential of meat products, so it can be assumed that this is a future direction for scientific research.

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.

Heterocyclic aromatic amines in meat: Formation mechanisms, toxicological implications, occurrence, risk evaluation, and analytical methods

Heterocyclic aromatic amines (HAAs) are detrimental substances can develop during the high-temperature cooking of protein-rich foods, such as meat. They are potent mutagens and carcinogens linked to an increased risk of various cancers. HAAs have complex structures with nitrogen-containing aromatic rings and are formed through chemical reactions between amino acids, creatin(in)e, and sugars during cooking. The formation of HAAs is influenced by various factors, such as food type, cooking temperature, time, cooking method, and technique. HAAs exert their toxicity through mechanisms like DNA adduct formation, oxidative stress, and inflammation. The research on HAAs is important for public health and food safety, leading to risk assessment and management strategies. It has also led to innovative approaches for reducing HAAs formation during cooking and minimizing related health risks. Understanding HAAs' chemistry and formation is crucial for developing effective ways to prevent their occurrence and protect human health. The current review presents an overview about HAAs, their formation pathways, and the factors influencing their formation. Additionally, it reviews their adverse health effects, occurrence, and the analytical methods used for measuring them.

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.

The influence of heat treatment type on the fat component and heterocyclic aromatic amines formation in minced poultry meat products

In this study the influence of heat treatment type on the change in the fatty acid composition, indices and parameters of fat oxidation, the level of heterocyclic amines formation in the chopped poultry ready-to-eat products enriched with ω‑3 fatty acids and an antioxidant complex were studied. The composition of ingredients and recipes of ready-to-eat products are developed with consideration of the medical and biological requirements for the diets of oncological patients. These ready-to-eat products feature some antioxidant substances in their composition that can bind free radicals, and provide for a reduction in the risk of carcinogens formation during the manufacturing process. The heat treatment was run in several ways, also called as modes — cooking in a microwave oven (MW), cooking in a convection oven in the “convection” mode with preliminary short-term roasting, steam cooking. For comparison, the conventional, i. e. not enriched food sample was used as a control one. The introduction of ω‑3 fatty acids into the food formulation made it possible to change the fatty acid composition towards increasing the proportion of polyunsaturated fatty acids (PUFAs). It was found that the profile of fatty acids was influenced by both the ingredients of the product and the type of its heat treatment. The joint use of a PUFA source and a complex of antioxidants made it possible to obtain a ready-to-eat product with a high level of ω‑3; and to ensure the ratio of ω‑6 group acids: ω‑3 ratio amounts to 1–2:1. Heat treatment of enriched semi-finished products by microwave cooking and by steam cooking showed a lesser effect on the change in the content and composition of polyunsaturated fatty acids — the loss of fatty acids was 1.2% and 2.8%, respectively, while in the “convection” cooking mode with preliminary roasting this loss was equal to 3.5%. It was found that the antioxidant complex in the composition of the food product and gentle heat treatment methods cause less lipid peroxidation and the formation of carcinogenic heterocyclic aromatic amines (HAA) during the food manufacturing process.

Effects of soy protein and its hydrolysates on the formation of heterocyclic aromatic amines in roasted pork

This study investigated the influence mechanism of soy protein and its hydrolysates (under three different degree of hydrolysis) on formation of heterocyclic aromatic amines (HAAs) formation in roasted pork. The results showed that 7S and its hydrolysates significantly inhibited the formation of quinoxaline HAAs, and the maximum inhibitory rate of MeIQx, 4,8-MeIQx, and IQx was 69%, 79%, and 100%, respectively. However, soy protein and its hydrolysates could promote the formation of pyridine HAAs (PhIP, and DMIP), its content increased significantly with the increase in the degree of hydrolysis of the protein. The content of PhIP increased 41, 54, and 165 times with the addition of SPI, 7S, and 11S at 11% degree of hydrolysis, respectively. In addition, they promoted the formation of β-carboline HAAs (Norharman and Harman), in a manner similar with that of PhIP, especially the 11S group. The inhibitory effect on quinoxaline HAAs was probably correlated with DPPH radical scavenging capacity. Nevertheless, the promotive effect on other HAAs might be related to the high levels of free amino acids and reactive carbonyls. This research may provide recommendation for the application of soy protein in high-temperature meat products.

Carbonyl-trapping by phenolics and the inhibition of the formation of carcinogenic heterocyclic aromatic amines with the structure of aminoimidazoazaarene in beef patties

Carcinogenic heterocyclic aromatic amines (HAAs) with the structure of aminoimidazoazaarene (PhIP, MeIQx, IQ, and MeIQ) are produced by reaction of creatin(in)e, ammonia, and reactive carbonyls (phenylacetaldehyde, acrolein, and crotonaldehyde). In an attempt to provide efficient methodologies for HAA reduction in beef patties, this study: identified phloroglucinol as the most efficient phenolic to reduce HAA formation (76–96% inhibition); isolated and characterized by NMR and MS phloroglucinol/phenylcetaldehyde and phloroglucinol/acrolein adducts; and determined by LC-MS/MS adduct formation in beef patties treated with phloroglucinol. Obtained results suggested that addition of trihydroxyphenols (including phloroglucinol) to beef patties should decrease HAA formation. This was confirmed by both immersing beef patties in apple (or pear) juice before cooking (>90% inhibition) and including wheat bran in patty recipe. All these results confirm the key role of reactive carbonyls in the formation of carcinogenic HAAs and propose carbonyl-trapping as a way for controlling HAA formation in food 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.

Chinese quince proanthocyanidins enhance frying performance and suppress heterocyclic aromatic amine formation in soybean oil

SummaryThe aim of the study was to evaluate the effect of Chinese quince proanthocyanidins (PAs) on the deterioration and heterocyclic aromatic amine (HAA) formation in soybean oil when used for deep‐fat frying, one tea polyphenol (Tea‐PP) and two PAs (PA‐100 and PA‐140) (200 mg/kg) were added to soybean oils. While all three retarded the accumulation of oil degradation products and enhanced performance of frying oil, as well as reduced the formation of HAAs, both PA‐100 and PA‐140 performed better than Tea‐PP. Adding PA‐100 and PA‐140 not only decreased the increase in oxidation indices and lossy of tocopherols but also inhibited HAA formation by 14.82%–30.64% and 19.52%–54.24%, respectively. Multivariate analysis revealed that PA‐140 always had a stronger effect than PA‐100 in concurrently enhancing frying performance and suppressing the generation of HAAs. This study provides evidence for using PAs from Chinese quince as the stabilisers of frying oils and inhibitors of HAA formation in these oils in the food industry.

Reducing effects of tea marinades on heterocyclic aromatic amines formation in chicken thigh meat: focus on white and oolong tea

Reducing effects of tea marinades on heterocyclic aromatic amines formation in chicken thigh meat: focus on white and oolong tea

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.

Advantageous Effects of Sumac Usage in Meatball Preparation on Various Quality Criteria and Formation of Heterocyclic Aromatic Amines

Heterocyclic aromatic amines (HAAs) are mutagenic/carcinogenic compounds that can be formed during the cooking process of proteinaceous foods such as meat. Therefore, it is needed to inhibit or reduce their formations in cooked meats. Hereby, the effects of sumac usage (0.5%, w/w) in beef meatball preparation on the formation of HAAs and some quality parameters (water, pH, cooking loss, and lipid oxidation values) of meatballs cooked at 150 and 250 °C were investigated. The sumac usage caused a reduction in pH (p &lt; 0.01), cooking loss (p &lt; 0.05), lipid oxidation level (TBARS, p &lt; 0.01), and total HAA amount (p &lt; 0.05) of the samples. In addition, increasing the cooking temperature significantly decreased the pH value (p &lt; 0.01) and increased the cooking loss (p &lt; 0.05) of the samples. Only one compound, 2-amino-3,8-dimethylimidazo [4,5-ƒ]quinoxaline (MeIQx), from nine different HAAs studied in this study, could be determined, and the levels of the other HAAs studied were lower than their detection limits. On the other hand, MeIQx was not detected in the samples cooked at 150 °C, it was only determined in the control group samples cooked at 250 °C. The sumac usage completely inhibited MeIQx formation in the samples. Due to its positive effect on cooking loss value, lipid oxidation level, and MeIQx formation, it can be suggested to use sumac powder in meatball preparation.