Understanding the heterocyclic aromatic amines: An overview and recent findings.

Heterocyclic aromatic amines (HAAs) constitute a group of highly toxic organic compounds strongly associated with the onset of various types of cancer. This paper aims to serve as a valuable resource for food scientists working towards a better understanding of these compounds including formation, minimizing strategies, analysis, and toxicity as well as addressing existing gaps in the literature. Despite extensive research conducted on these compounds since their discovery, several aspects remain inadequately understood, necessitating further investigation. These include their formation pathways, toxic mechanisms, effective mitigation strategies, and specific health effects on humans. Nonetheless, recent research has yielded promising results, contributing significantly to our understanding of HAAs by proposing new potential formation pathways and innovative strategies for their reduction.

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.

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.

Vegetable extracts: Effective inhibitors of heterocyclic aromatic amines and advanced glycation end products in roasted Mackerel.

The formation of hazardous substances, heterocyclic aromatic amines (HAAs) and advanced glycation end products (AGEs), in roasted mackerel with different cooking temperatures (180, 210, 240 °C) and vegetable extracts (celery, carrot and yam extracts) in a preheated oven was investigated. The results indicated that the introduction of vegetable extracts had inhibitory effects on HAAs and AGEs during thermal processing, especially celery extracts. Benefiting from the addition of vegetable extracts, the roasted mackerel keep high quality against lipid/protein oxidation, avoids nutrition loss of polyunsaturated fatty acids, and flavor is promoted. We also examined the variation of key precursors, including creatine, creatinine, reducing sugars, amino acids and attempted to explain the molecular pathway of inhibition of the formation of the hazardous substances by vegetable extracts. The results provide theoretical support to develop technologies for inhibiting hazardous substances formation during fish processing, which is important for food manufacturers and consumers for producing healthier meat products.

Effect of Traditional Stir-Frying on the Characteristics and Quality of Mutton Sao Zi.

The effects of stir-frying stage and time on the formation of Maillard reaction products (MRP) and potentially hazardous substances with time in stir-fried mutton sao zi were investigated. 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) mainly presented were of stir-fried mutton sao zi. The furosine decreased after mixed stir-frying (MSF) 160 s due to its degradation as the Maillard reaction (MR) progressed. The fluorescent compound gradually increased with time during the stir-frying process. The CML and CEL peaked in MSF at 200 s. AA reached its maximum at MSF 120 s and then decreased. All the 5 HAAs were detected after MSF 200 s, suggesting that stir-frying mutton sao zi was at its best before MSF for 200 s. When stir-frying exceeded the optimal processing time of (MSF 160 s) 200 s, the benzo[a]pyrene peaked at 0.82 µg/kg, far lower than the maximum permissible value specified by the Commission of the European Communities. Extended stir-frying promoted MRP and some hazardous substances, but the content of potentially hazardous substances was still within the safety range for food.

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.

Heterocyclic aromatic amines in cooked food: A review on formation, health risk-toxicology and their analytical techniques.

Heterocyclic aromatic amines (HAAs) are defined as a major class of poisonous compounds formed from proteinaceous foods during heat processing and flavour-forming. These toxicants have detrimental effects on the human body and eventually bring about mutagenicity and carcinogenicity. Owing to the presence of HAAs at a marginal level in the intricate tissue of food and their interactivity, an effective sample preparation should be employed to extract these controversial chemicals from the food matrix. For separation and detection of HAAs, advanced extraction methods and instrumental techniques have been applied. According to the type of sample preparation, sensitivity of the experiment, laboratory conditions and available facilities, the choice of analytical equipment will be different. In this review, various cooked food samples containing HAAs and heat processing of them have been listed. Also, sample pre-treatment and analytical techniques that have been applied to determine HAAs are discussed.