Formation Of Heterocyclic Amines Research Articles

Effect of Chinese quince proanthocyanidins on the inhibition of heterocyclic amines and quality of fried chicken meatballs and tofu.

Heterocyclic amines (HCAs) have potential carcinogenic and mutagenic activity and are generated in cooked protein-rich foods. Adding proanthocyanidins (PAs) to these foods before frying is an effective way to reduce HCAs. In this study, polymeric PAs (PPA) and ultrasound-assisted acid-catalyzed/catechin nucleophilic depolymerized PAs (UAPA, a type of oligomeric PA) were prepared from Chinese quince fruits (CQF). Different levels of PPA and UAPA (0.05%, 0.1%, and 0.15%) were added to chicken meatballs and tofu; then these foods were fried, and the content of HCAs in them after frying was investigated. The results showed that PPA and, particularly, UAPA significantly inhibited the formation of HCAs in fried meatballs and tofu, and this inhibition was dose-dependent. The inhibition of HCAs by both PPA and UAPA was stronger in the chicken meatballs than in fried tofu. The level of total HCAs was significantly reduced by 57.84% (from 11.93 to 5.03ng/g) after treatment of meatballs with 0.15% UAPA, with inhibition rates of 78.94%, 50.37%, and 17.81% for norharman, harman, and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), respectively. Of note, there was a negative correlation between water, lipid, protein, creatine, and glucose content and HCA content in the crust, interior, and whole (crust-plus-interior) measurements of all fried samples. Interestingly, PPA and UAPA were found more effective in inhibiting HCAs in the exterior crust than in the interior of the fried chicken meatballs. These results provide evidence that further studies on the reduction of the formation of harmful HCAs in fried foods by adding CQF PAs could be valuable to the fried food industry. PRACTICAL APPLICATION: Chinese quince proanthocyanidins treatments significantly inhibited the generation of heterocyclic amines (HCAs) in chicken meatballs and tofu when deep-fried. These results suggest that Chinese quince proanthocyanidins can be used as natural food additive for reducing HCAs in fried foods, laying the foundation for using Chinese quince fruit proanthocyanidins for HCA inhibition in the food industry.

Effects of basic amino acids on heterocyclic amines and quality characteristics of fried beef patties at low NaCl level

The impact of basic amino acids (Lysine, Arginine, Histidine) on the formation of total heterocyclic amines (HAs) was investigated in fried beef patties at 1% NaCl level. Different levels of basic amino acids (0.1%, 0.5%, 1%) significantly inhibited the formation of the total and individual HAs at 1% NaCl, and the inhibitory effect was more effective than 3% NaCl (6.19 ng/g, 26.93% inhibition) (P < 0.05). Lys at 1% reduced total HAs the most (2.46 ng/g, 70.88% inhibition), followed by 1% His (2.79 ng/g, 67.03% inhibition) and 1% Arg (3.43 ng/g, 59.51% inhibition). Compared to the 3% NaCl, the quality characteristics (moisture content, frying loss, texture profile, and color) of the fried beef patties were significantly improved when basic amino acids were added at 1% NaCl (P < 0.05). The lipid oxidation of fried beef patties was significantly inhibited by 1% Arg and 1% Lys at 1% NaCl level (P < 0.05). The results indicated that basic amino acids could inhibit the formation of total HAs while maintaining the quality of meat products at low NaCl condition.

Effects of grilling conditions on heterocyclic amines and quality attributes of grilled grass carp

SummaryThe effects of different grilling temperatures (220 °C, 250 °C, 280 °C, 310 °C) reaching the central temperature of 70 °C on heterocyclic amines (HAs) formation, moisture content, cooking loss, texture, colour, and sensory properties of grilled grass carp (Ctenopharyngodon idella) were investigated. The grilling condition significantly (P &lt; 0.05) affected cooking loss, moisture content, heterocyclic amines (HAs) formation, texture, colour and sensory properties. The results showed that 5 kinds of free and 9 kinds of protein‐bound heterocyclic amines were detected. The total amount of protein‐bound heterocyclic amines was much higher than that of the free state. Harman and Norharman, belonging to β‐carboline, constituted over 80% of the total content of heterocyclic amines. Considering the HAs formation and quality attributes, when the grilling condition was 280 °C for 10 min, the total content of HAs was the lowest, and the fish had moderate moisture content, firm texture, bright colour, and high sensory evaluation score.

A Disconnection for Rapid Access to Heterocyclic Benzylic Amines with Fully Substituted α-Carbons.

2- or 4-Pyridyl benzylic amines represent a privileged motif in drug discovery. However, the formation of heterocyclic benzylic amines with fully substituted α-carbons can require the execution of lengthy synthetic routes, which limit their application. Addition of various nucleophilic agents to Ellman's imines has been well established; however, there is no precedented literature reported for pyridyl-type nucleophiles, which are very important for medicinal chemistry. In this letter, we disclose the development of a one-step synthesis of heterocyclic benzylic amines with fully substituted α-carbons from heteroaryl halides and sulfinyl imines. Starting from 2,4-dibromopyridine, regioselective synthesis of 2- or 4-pyridyl benzylic amines could be achieved by choosing toluene or MTBE as a solvent.

Effects of seasoning addition and cooking conditions on the formation of free and protein-bound heterocyclic amines and advanced glycation end products in braised lamb

The accumulation of heterocyclic amines (HAs) and advanced glycation end products (AGEs) in thermally processed meats has been arising safety concerns. The effects of cooking conditions and seasoning addition on the formation of HAs and AGEs in Chinese traditional braised lamb were investigated by UPLC-MS/MS analysis. Soy sauce significantly increased the formation of HAs and AGEs, among which light soy sauce had the greatest promoting effect (69.45–15300.62 %). Conversely, spices inhibited HAs and AGEs formation, the inhibition rate of free HAs and AGEs reached 22.06–34.72 % when using 70 % ethanol extract. Hot blanching treatment and adding soy sauce and spices at a later stage could significantly suppress HAs and AGEs production. Flavonoids, including galangin, hesperidin, narirutin, etc., were identified as key effectors in spices. These findings help to promote awareness of the formation of HAs and AGEs in braised lamb and provide valuable insights for optimizing processing techniques to minimize their production.

Effect of temperature, pH, metal ions, and oil type on Chinese quince proanthocyanidins' thermal stability, antioxidant activity, and inhibition of heterocyclic amine formation during simulated frying

Heterocyclic amines (HCAs) are potent carcinogenic and mutagenic compounds generated during the frying of meat. The addition of Chinese quince proanthocyanidins (PAs) to fried food can reduce HCA formation. However, differences in food parameters (such as temperature, pH, presence of metal ions, and oil type) affect the efficacy of PA-mediated inhibition of HCA formation. In this study, two PAs (P1 and P2) of different molecular weights were prepared from Chinese quince. The effects of pH, metal ions, and oil type on the thermal stabilities, antioxidant capacities, and HCA-inhibitory abilities of P1 and P2 were studied during simulated frying. After simulated frying, the degree of polymerization (DP) and molecular weights of P1 decreased dramatically from 15224 Da to 2280 Da, while they decreased slightly in P2. Fe3+ decreased the thermal stability of P1 and P2 more than high pH; however, both factors reduced the HCA formation-inhibitory activity. Notably, the thermal stabilities of P1 and P2 in sunflower oil were lower than those in other oils; however, the inhibition of HCAs by P1 and P2 in sunflower oil (69.31% and 72.11%, respectively, for norharman) differed only slightly from that in the other oils. Multivariate analysis revealed positive correlations among thermal stabilities, antioxidant capacities, and HCA-inhibitory activities. Thus, Chinese quince PAs may be potentially used as food additives to mitigate the production of harmful HCAs in fried food.

Simultaneous Identification and Quantification of Phenylalanine, Glycine and Lysine amino acids and conjugated heterocyclic amines in Maillard chemical model system using RP-HPLC-DAD

In this study, we developed a simple reversed-phase high-performance liquid chromatography (RP-HPLC) methodology for simultaneous identification and quantification of three types of mix: (1) phenylalanine and PHIP; (2) glycine and MeIQx; (3) lysine and 4,8 DiMeIQx in Maillard chemical model systems. In addition, we investigated the effects of different conditions on decreasing amino acids and heterocyclic amines (HCA) formation in chemical model systems. The results show that the developed methods used to separate the proposed mixes gave a relative standard deviation (RSD)% of less than 2% of peak area and retention time, thus proving the robustness and high reproducibility of the proposed method. The relationship between concentration and peak areas is linear with high statistical significance (p&lt;0.001). The residual and slope of linear regression give a limit of detection LoD) and (LoQ) of phenylalanine and PHIP were (2.92- 0.029 ppm),(9.73- 0.098 ppm),respectively, which indicate the high sensitivity of the developed method. Moreover, the findings illustrate that a water ratio of 20% leads to a decrease in phenylalanine versus the largest amount of PHIP, and phenylalanine is the most active amino acid with a decreasing percentage up to 99%.

Formation and prediction of heterocyclic amines and N-nitrosamines in smoked sausages using back propagation artificial neural network.

Heterocyclic amines (HAs) and N-nitrosamines (NAs) are formed easily during the thermal processing of food, and epidemiological studies have demonstrated that consuming HAs and NAs increases the risk of cancer. However, there are few studies on the application of back propagation artificial neural network (BP-ANN) models to simultaneously predict the content of HAs and NAs in sausages. This study aimed to investigate the effects of cooking time and temperature, smoking time and temperature, and fat-to-lean ratio on the formation of HAs and NAs in smoked sausages, and to predict their total content based on the BP-ANN model. With an increase in processing time, processing temperature and fat ratio, the content of HAs and NAs in smoked sausages increased significantly, while the content of HA precursors and nitrite residues decreased significantly. The optimal network topology of the BP-ANN model was 5-11-2, the correlation coefficient values for training, validation, testing and all datasets were 0.99228, 0.99785, 0.99520 and 0.99369, respectively, and the mean squared error value of the best validation performance was 0.11326. The bias factor and the accuracy factor were within acceptable limits, and the predicted values approximated the true values, indicating that the model has good predictive performance. The contents of HAs and NAs in smoked sausages were significantly influenced by the cooking conditions, smoking conditions and fat ratio. The BP-ANN model has high application value in predicting the contents of HAs and NAs in sausages, which provides a theoretical basis for the suppression of carcinogen formation. © 2024 Society of Chemical Industry.

Modified Chinese quince oligomeric proanthocyanidin protects deep-frying oil quality by inhibiting oxidation

Chinese quince (Chaenomeles sinensis) fruit is an underutilized resource, rich in proanthocyanidins with antioxidant ability but poor lipid solubility. In this study, a novel modified oligomeric proanthocyanidin (MOPA) was prepared, which exhibited favorable lipid solubility (354.52 mg/100 g). It showed higher radical scavenging abilities than commercial antioxidant-BHA (butylated hydroxyanisole), both at 0.4–0.5 mg/mL. The addition of MOPA (0.04 %wt.) significantly increased the oxidative stability index of the soybean oil from 5.52 to 8.03 h, which was slightly lower than that of BHA (8.35 h). Analysis of the physicochemical properties and composition of oil during deep-frying showed that MOPA demonstrated significant antioxidant effects and effectively restricted the oil oxidation. This inhibition also delays the formation of heterocyclic amines (HAs) in fried food, thereby reducing the migration of HAs from food to deep-frying oil. Therefore, MOPA is a promising novel liposoluble antioxidant for protecting the quality of deep-frying oil.

Effect of mulberry leaf (Morus alba L.) extract on the quality and formation of heterocyclic amines in braised muscovy duck

Effect of mulberry leaf (Morus alba L.) extract on the quality and formation of heterocyclic amines in braised muscovy duck

Effect of structurally different pectin combined with polyphenol on water distribution, protein oxidation and heterocyclic amines formation in meat-based snacks

This research studied the effect of structurally different pectin combined with polyphenol (PP) on the physicochemical properties, inhibition of protein oxidation and heterocyclic amines (HAs) formation in fish meat snacks. The findings demonstrated that pectin with a high degree of esterification (DE) and average chain length (ACL) significantly reduced cooking loss, improved zeta potential values, and reduced particle size when combined with polyphenols, indicating an inhibition of protein aggregation and crosslinking. The addition of PP decreased the carbonyl formation as compared to individual polyphenol and control. Low Field Nuclear Magnetic Resonance (LF-NMR) analysis publicized that PP combination increased the water binding capacity, which resulted in less free water (T22 and T23) in those samples. Furthermore, LC/MS analysis revealed that PP combination, retained the water inside the macromolecules and prevented the relocation of water to the surface, which resulted in the less HAs formation as compared to control. The scanning electron microscopy (SEM) revealed that combination of PP samples formed a compact structure evidenced by less wide holes while control sample revealed loose structure. The findings suggest that 201 and 601 pectin combined with catechin have potential to improve the physicochemical properties and inhibition of hazardous compound formation.

Effects of Fingerroot (Boesenbergia pandurata) Oil on Microflora as an Antimicrobial Agent and on the Formation of Heterocyclic Amines in Fried Meatballs

This study aimed to determine the antibacterial activity of the essential oil of fingerroot (Boesenbergia pandurata) (EOF) as a natural preservative in ground meat and its effect on the formation of heterocyclic amines (HAs) in pan-fried meatballs. EOF was applied either by adding it to ground pork or marinating pork in it before grinding. In addition, the antibacterial activity of EOF was tested. Aerobic mesophilic total viable count (TVC), lactic acid bacteria (LAB), and Enterobacteriaceae bacteria were monitored. The results show that EOF exhibited strong antibacterial activity when added at concentrations of 1.0 and 2.5 wt%. Antimicrobial activity against TVC, LAB, and especially Enterobacteriaceae bacteria was observed at all EOF concentrations (0.25, 0.5, 1.0, and 2.5 wt%). A 2.5% concentration of EOF applied by marinating trimmings can extend the shelf-life of ground pork to 18 days, while 2.5% EOF applied via addition can extend the shelf-life to 15 days, compared with 3 days for the control sample. After frying the meatballs, the inhibitory effect on the formation of heterocyclic amines was only significant for MeIQx with the highest addition of EOF (2.5 wt%). Significant increases in the concentrations of all other HAs were determined by adding EOF (2.5 wt%).

Effects of quercetin and l-ascorbic acid on heterocyclic amines and advanced glycation end products production in roasted eel and lipid-mediated inhibition mechanism analysis

Eel is a commercially important marine fish, frequently featured as sushi or roasted preparations. This study determined the formation of heterocyclic amines (HAs) and advanced glycation end products (AGEs) in roasted eel and evaluated the inhibitory mechanism of quercetin and l-ascorbic acid on their formation. The results indicate a respective reduction of 75.07% and 84.72% in total HAs, alongside a decline of 23.03% and 39.14% in AGEs. Additionally, fundamental parameters of roasted eel, lipid oxidation indicators and precursors were measured to elucidate the mechanisms and impact of natural antioxidants on HAs and AGEs formation in roasted eel. Furthermore, endeavors were made to probe into the molecular mechanisms governing the influence of key differential lipids on the generation of HAs and AGEs through lipid-mics analysis. This research emphasizes the potential of natural antioxidants in preventing harmful substances formation during eel thermal processing, which is helpful to food manufacturers for healthier food production.

Citrus Peel Extracts: Effective Inhibitors of Heterocyclic Amines and Advanced Glycation End Products in Grilled Pork Meat Patties.

In the present study, citrus peels were extracted using various conventional and deep eutectic solvents (DESs). Compared to other citrus peel extracts, the DES extract based on choline chloride showed notably higher total phenolic and flavonoid content levels, along with superior antioxidant activity, among these extracts. Consequently, this study aimed to further investigate the inhibitory effects of the choline chloride based DES extract on the production of both free and bound heterocyclic amines (HAs) and advanced glycation end products (AGEs) in roast pork meat patties. The results indicated that the addition of choline chloride-based DES extracts, particularly the choline chloride-carbamide based DES extract, can effectively reduce the oxidation of lipids and proteins by quenching free radicals. This approach proves to be the most efficient in reducing the formation of both HAs and AGEs, leading to a significant reduction of 19.1-68.3% and 11.5-66.5% in free and protein-bound HAs, respectively. Moreover, the levels of free and protein-bound AGEs were reduced by 50.8-50.8% and 30.5-39.8%, respectively, compared to the control group. Furthermore, the major phenolics of citrus peel extract identified by UHPLC-MS were polymethoxylated flavonoids (PMFs) including hesperidin, isosinensetin, sinensetin, tetramethoxyflavone, tangeretin, and hexamethoxyflavone, which inferring that these compounds may be the main active ingredients responsible for the antioxidant activity and inhibition effects on the formation of HAs and AGEs. Further research is needed to explore the inhibitory effects and mechanisms of PMFs with different chemical structures on the formation of HAs and AGEs.

Effect of spices on the formation and inhibition of heterocyclic amines in barbecued pork

Effect of spices on the formation and inhibition of heterocyclic amines in barbecued pork

Effect of plant polyphenols with different m-hydroxy and o-hydroxy groups on the inhibition of heterocyclic amines formation in roasted meat

Effect of plant polyphenols with different m-hydroxy and o-hydroxy groups on the inhibition of heterocyclic amines formation in roasted meat

Effect of Angelica dahurica, Angelica dahurica polysaccharides, and imperatorin on free and bound heterocyclic amine generation in roasted beef patties and release profiles of bound heterocyclic amines during in vitro digestion

This study explored the suppressive activity of Angelica dahurica (AD), AD polysaccharides, and imperatorin on free and bound heterocyclic amine (HA) formation in roast beef patties and release profiles of bound HAs during in vitro digestion. The suppressive effects and potential mechanisms associated with free radical quenching were explored using UPLC-MS/MS, multivariate statistical analysis, and electron paramagnetic resonance (EPR). AD (0.5%, 1.0%, and 1.5%) and imperatorin (0.005%, 0.010%, and 0.015%) showed a dose-dependent inhibition for both free and bound HAs, with AD polysaccharides showing a slight inhibitory capacity. The maximum inhibition of free and bound HAs was 36.31% (1.5% AD) and 35.68% (0.015% imperatorin). The EPR results demonstrated that alkyl radicals and 1O2 were the pivotal free radicals for HAs. Furthermore, AD and imperatorin dose-dependently decreased the level of these radicals. Intriguingly, after in vitro digestion, only AD polysaccharides significantly inhibited the release of bound HAs, with imperatorin even facilitating the release process. In this study, the capacity of the AD polysaccharide to suppress the release of bound HAs and the ability of AD and imperatorin to inhibit free and bound HAs in beef patties were identified for the first time.

Paprika extract as a natural antioxidant in cold-stored pork patties: Effect on oxidative stability and heterocyclic amines inhibition

In this study, we compared the degree of oxidation of pork patties refrigerated at 7 °C for 0, 7, and 14 days and the content of 10 types of heterocyclic amines (HCAs) after heating. The pork patties used in the study were added with 0.7 mg sodium nitrite (SN) and 5 mg paprika extract (PE), respectively. IQx (2-Amino-3-methyl-imidazo[4,5-f]-quinoxaline), MeIQx (2-Amino-3, 8-dimethyl-imidazo[4,5-f]-quinoxaline), PhIP (2-Amino-1-methyl-6-phenyl-imidazo[4,5-b]-pyridine), and Harman (1-Methyl-9H-pyrido[4,3-b]-indole) contents increased with increasing storage periods of treatment. On the other hand, HCAs production in SN and PE treatments were suppressed over the storage period, with IQ (2-Amino-3-methyl-imidazo[4,5-f]-quinoline) and Aαc (2-Amino-9H-dipyrido[2,3-b]-indole) being suppressed significantly (P < 0.05). The control's pH, cooking loss, lipid, and protein oxidation were higher than SN and PE-treated patties at 14 d (P < 0.05). These differences affect the formation of HCAs. PLS-DA showed a strong correlation between protein oxidation and IQx, Harman, 4,8-DiMelQx (2-Amino-3, 4, 8-trimethyl-imidazo[4,5-f]-quinoxaline), PhIP, and MeIQx, while lipid oxidation correlated with IQx, Harman, and PhIP. Both SN and PE showed HCAs inhibitory activity and exhibited oxidative stability during storage.

Comprehensive Analyses of Advanced Glycation end Products and Heterocyclic Amines in Peanuts during the Roasting Process.

Advanced glycation end products (AGEs) and heterocyclic amines (HAs) are two kinds of important harmful products formed simultaneously during the thermal processing of proteinaceous food. In this paper, the effect of roasting conditions on the formation of AGEs and HAs, as well as active carbonyl intermediates in common peanut (C-peanut) and high-oleic acid peanut (HO-peanut) was studied simultaneously for the first time. In general, with the increase in roasting temperature (160-200 °C) and time, the contents of AGEs, HAs and active carbonyl intermediates (i.e., glyoxal (GO) and methylglyoxal (MGO)) significantly increased in peanuts. Four kinds of HAs (i.e., AαC, DMIP, Harman and Norharman) were observed in roasted peanuts, of which Harman and Norharman accounted for about 93.0% of the total HAs content after roasting for 30 min at 200 °C. Furthermore, a correlation analysis among AGEs (i.e., Nε-(1-Carboxymethyl)-L-lysine (CML) and Nε-(1-Carboxyethyl)-L-lysine (CEL)), HAs, GO and MGO was conducted. Most of these compounds showed an excellent positive linear relationship (p ≤ 0.001) with each other. The evident increase in GO and MGO contents implied an increase in not only the content of AGEs but also HAs. However, contents of AGEs and HAs showed no significant difference between roasted HO-peanut and C-peanut. This study would provide a theoretical basis for simultaneously controlling the levels of AGEs and HAs in thermal processed peanut foods.

Inhibitory Effects of Some Hydrocolloids on the Formation of Advanced Glycation End Products and Heterocyclic Amines in Chemical Models and Grilled Beef Patties.

Effectively inhibiting the formation of heterocyclic amines (HAs) and advanced glycation end products (AGEs) is crucial to human health. In the present study, chemical model systems were used to evaluate the inhibitory effects of seven hydrocolloids on HA and AGE formation. The results showed that hydrocolloids effectively inhibited the formation of two major AGEs. However, their inhibitory action against HA formation showed unexpected results, wherein alginic acid, carrageenan and konjac glucomannan promoted the formation of 2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP), harmane, norharmane and 2-amino-3,8-dimethyl-imidazo [4,5-f]-quinoline (MeIQx). Only chitosan and pectin showed significant inhibitory effects on HAs, reducing HA levels by 34.5-56.3% and 30.1-56.6%, respectively. In grilled beef patties, the addition of 1.5% chitosan and pectin significantly decreased AGE and HA content by 53.8-67.0% and 46.9-68.1%, respectively. Moreover, it had a limited impact on quality and sensory properties. Further mechanism studies conducted in model systems revealed that chitosan and pectin decreased the formation of key intermediates of AGEs and HAs. These findings suggest that chitosan and pectin are powerful inhibitors against AGE and HA formation with minimal impact on food quality. Therefore, their application in meat preparation and processing could effectively decrease human dietary exposure to HAs and AGEs.