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1.
Int J Biol Macromol ; 280(Pt 2): 135503, 2024 Sep 18.
Article in English | MEDLINE | ID: mdl-39304045

ABSTRACT

Thermal processing of meat leads to the development of Maillard's reaction intermediates, and carcinogenic toxicants. For the first time, the effectiveness of three (HX-12A, HX-12B and HX-12C) antimicrobial peptides (AMPs) against the formation of heterocyclic amines (HAs) in chemical and meat model systems. The results showed that AMPs especially 12A and 12C have strong metal chelation potential (48 and 40% at 1 mg/ml) and antioxidant activity (35 and 25% at 1 mg/ml), respectively, which were endorsed by their secondary structure (FTIR analysis) in terms of high ß-sheets (1628 cm-1 and 1672 cm-1) in those AMPs. UPLC-MS analysis revealed that 12A and 12C were the most capable AMPs in MeIQx and PhIP-producing chemical models, respectively, whereas 12B promoted the HAs formation even higher than control. In particular, 12C AMP significantly (P < 0.05) decreased the most abundant carcinogenic HAs (PhIP) up to 90% at 9 mg/100 g of fresh meat, whereas 12A inhibited up to 80% of mutagenic HAs at same level compared to control and 12B. Low Field Nuclear Magnetic Resonance (LF-NMR) test showed that inhibitory effect of 12A and 12C was mediated by means of retaining water (lower T22 and T23 relaxation time) inside the macromolecules. This favorable effect was also evidenced by significantly enhanced tryptophan fluorescent intensity. Finally, based on correlation and principle component analysis, the mechanism of action has been proposed. These outcomes recommend that 12A and 12C are potential AMPs for the attenuation of HAs in thermally processed meat-based products.

2.
Food Chem ; 460(Pt 3): 140576, 2024 Dec 01.
Article in English | MEDLINE | ID: mdl-39106755

ABSTRACT

The inhibition of amino acids on the formation of protein-bound HAs was assessed in both model systems and roast beef patties, and the synergism between these amino acids was also investigated. The amino acids can promote the formation of protein-bound HAs at low addition amount, and the total content of protein-bound HAs increased from 444.05 ± 4.98 ng/g of the control group to 517.36 ± 16.51 ng/g when 0.05 % cysteine was added. Amino acid combinations exhibited stable inhibitory effects, with the maximum inhibitory rate of 64 % in the treatment with histidine-proline combination (1:4). The synergistic inhibition may be caused by simultaneously scavenging intermediates and competing for the binding sites of muscle proteins, and the reaction with protein-bound HAs to form adduct can serve as supporting factors to co-mitigate the promotion in protein-bound HAs from increased protein solubility. These findings proposed the potential mitigation strategies against protein-bound HAs formation.


Subject(s)
Amines , Amino Acids , Animals , Cattle , Amino Acids/chemistry , Amino Acids/metabolism , Amines/chemistry , Amines/metabolism , Muscle Proteins/chemistry , Muscle Proteins/metabolism , Myofibrils/chemistry , Myofibrils/metabolism , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/pharmacology , Sarcoplasmic Reticulum/metabolism , Sarcoplasmic Reticulum/chemistry
3.
Food Sci Nutr ; 12(7): 4667-4679, 2024 Jul.
Article in English | MEDLINE | ID: mdl-39055183

ABSTRACT

Heterocyclic amines (HAs) are a group of mutagenic and carcinogenic compounds produced from the processing of high-protein foods, which include 2-amino-3-methylimidazo[4, 5-f]quinoline (IQ) showing the strongest carcinogenic effect. Camels are able to digest HAs in foods, which provide rich microbial resources for the study. Thus, camel rumen and intestinal microbiota were used to degrade IQ, and the dominant microorganisms and their degradation characteristics were investigated. After three generations of culture with IQ as the sole carbon source, the highest abundance in rumen and intestinal microbes was found in the Proteobacteria phylum. The strains of third generation of the rumen contents were mainly attributed to the genera Brevundimonas and Pseudomonas, and the dominant genera in intestine were Ochrobactrum, Bacillus, and Pseudomonas. Microorganisms were further isolated and purified from the third generation cultures. These 27 strains from the rumen (L1-L27) and 23 strains from the intestine (C1-C23) were obtained. Among them, four strains with the most effective degrading abilities were as follows: L6 (28.55% of IQ degrading rate) and C1 (25.19%) belonged to the genus Ochrobactrum, L15 (23.41%) belonged to the genus Pseudomonas, and C16 (20.89%) were of the genus Bacillus. This study suggested the application of abundant microbial resources from camels' digestive tract to biodegrade foodborne toxins.

4.
Food Res Int ; 190: 114633, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38945584

ABSTRACT

The Frankfurter sausages smoked with beech, oak, and alder, respectively, were used to clarify the underlying impact of the smoke chemical composition on the levels of heterocyclic amines (HAs) and polycyclic aromatic hydrocarbons (PAHs). The result indicated that different wood types significantly affected the profiles of target substances in food matrices. The beech-smoked samples had lower contents of total free HAs (5.98-6.80 ng/g dry-weight-DW), PAH4 (3.31-3.83 ng/g DW), and PAH8 (10.0-10.8 ng/g DW), whereas the alder pyrolysis usually led to higher hazardous residues (8.26-9.19 ng/g DW of total free HAs, 4.24-6.60 ng/g DW of PAH4 and 14.1-23.3 ng/g DW of PAH8). In addition, the differences in smoke chemical composition were attributed to the different proportions of 15 key identified substances. Among them, two aldehydes (5-methyl-furfural & furfural) and two phenols (phenol & 5-hydroxymaltol) may have synergistic or competitive inhibitory effects on the formation of HAs and PAHs in smoked meat products.


Subject(s)
Amines , Meat Products , Polycyclic Aromatic Hydrocarbons , Smoke , Wood , Polycyclic Aromatic Hydrocarbons/analysis , Meat Products/analysis , Smoke/analysis , Wood/chemistry , Amines/analysis , Heterocyclic Compounds/analysis , Food Contamination/analysis , Animals
5.
Antioxidants (Basel) ; 13(6)2024 Jun 06.
Article in English | MEDLINE | ID: mdl-38929134

ABSTRACT

This explorative study aimed to assess the mutagenicity and genotoxicity of stored-cooked beef patties formulated with and without phenols (7.00 mg of phenols/80-g patty) extracted from olive vegetation water (OVW), as related to the formation of cholesterol oxidation products (COPs) and heterocyclic amines (HCAs). The patties were packaged in a modified atmosphere, sampled during cold storage (4 °C) for 9 days, and grilled at 200 °C. The genotoxicity was evaluated by the Comet assay. The patty extract was found to be genotoxic on primary peripheral blood mononuclear cells (PBMCs), while no mutagenicity was detected. The addition of OVW phenols significantly decreased the genotoxicity of the patty extract and reduced the total COPs content in stored-cooked patties (4.59 times lower than control); however, it did not affect the content of total HCAs (31.51-36.31 ng/patty) and the revertants' number. Therefore, these results demonstrate that the OVW phenols were able to counteract the formation of genotoxic compounds in stored-cooked beef patties.

6.
J Hazard Mater ; 475: 134843, 2024 Aug 15.
Article in English | MEDLINE | ID: mdl-38870859

ABSTRACT

ß-Carboline heterocyclic amines (ß-CHAs), known for their synergistic neurotoxic and carcinogenic effects, are predominantly produced by humans through cigarette smoke and food and are found particularly in meats cooked at high temperatures. Few studies have explored the differences in the mechanisms of accumulation of ß-CHAs in smoked meat and meat processed at high temperatures. In this research, the concentration of ß-CHAs in smoked meats prepared using a variety of wood materials was measured using LCMS/MS. Additionally, key volatile organic compound markers associated with ß-CHAs accumulation in smoke were identified through GCMS and multivariate statistical analysis and subsequently confirmed in a chemical simulation system. Three types of strainers, each with a distinct aperture size, were used to assess the efficacy of particle filtration in reducing ß-CHAs levels in smoked meat. The findings indicated that smoke exposure indeed increases the ß-CHAs content of meat. However, only the strainer capable of filtering PM2.5-sized particles reduced the amount of ß-CHAs present compared to the control group. In contrast, strainers with larger pore sizes facilitated excessive accumulation of ß-CHAs. The presence of aldehydes such as 1 H-pyrrole-2-carboxaldehyde, 5-methylfurfural, benzaldehyde, furfural, and nonanal exhibited a positive correlation with the accumulation of ß-CHAs. Conversely, phenolic compounds, including 2-methoxy-4-vinylphenol, 2-methoxy-5-methylphenol, p-cresol, phenol, 2-methoxy-4-(1-propenyl)-, (Z)-, phenol, 3-ethyl-, and phenol, 4-ethyl-2-methoxy-, showed a negative correlation. Thus, filters made from chelated carbonyl trap materials both chemically and physically disrupt the buildup of ß-CHAs in smoked meats. The use of this approach will not only improve the quality of these products but will also contribute to decreasing the amount of inhalation pollutants released into the environment.


Subject(s)
Carbolines , Smoke , Carbolines/chemistry , Smoke/analysis , Amines/chemistry , Amines/analysis , Animals , Meat/analysis , Meat Products/analysis , Cooking , Wood/chemistry , Particulate Matter/analysis , Volatile Organic Compounds/analysis , Volatile Organic Compounds/chemistry , Heterocyclic Compounds/analysis
7.
Cardiovasc Toxicol ; 24(8): 747-756, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38851663

ABSTRACT

Metabolic dysfunction associated-steatotic liver disease (MASLD)/metabolic dysfunction-associated steatohepatitis (MASH) is the liver manifestation of metabolic syndrome, which is characterized by insulin resistance, hyperglycemia, hypertension, dyslipidemia, and/or obesity. Environmental pollutant exposure has been recently identified as a risk factor for developing MASH. Heterocyclic amines (HCAs) are mutagens generated when cooking meat at high temperatures or until well-done. Recent epidemiological studies reported that dietary HCA exposure may be linked to insulin resistance and type II diabetes, and we recently reported that HCAs induce insulin resistance and glucose production in human hepatocytes. However, no previous studies have examined the effects of HCAs on hepatic lipid homeostasis. In the present study, we assessed the effects of two common HCAs, MeIQx (2-amino-3, 8-dimethylimidazo [4, 5-f] quinoxaline) and PhIP (2-amino-1-methyl-6-phenylimidazo[4, 5-b] pyridine), on lipid homeostasis in cryopreserved human hepatocytes. Exposure to a single concentration of 25 µM MeIQx or PhIP in human hepatocytes led to dysregulation of lipid homeostasis, typified by significant increases in lipid droplets and triglycerides. PhIP significantly increased expression of lipid droplet-associated genes, PNPLA3 and HSD17B13, and both HCAs significantly increased PLIN2. Exposure to MeIQx or PhIP also significantly increased expression of several key genes involved in lipid synthesis, transport and metabolism, including FASN, DGAT2, CPT1A, SCD, and CD36. Furthermore, both MeIQx and PhIP significantly increased intracellular cholesterol and decreased expression of PON1 which is involved in cholesterol efflux. Taken together, these results suggest that HCAs dysregulate lipid production, metabolism, and storage. The current study demonstrates, for the first time, that HCA exposure may lead to fat accumulation in hepatocytes, which may contribute to hepatic insulin resistance and MASH.


Subject(s)
Cryopreservation , Hepatocytes , Homeostasis , Lipid Metabolism , Humans , Hepatocytes/metabolism , Hepatocytes/drug effects , Lipid Metabolism/drug effects , Homeostasis/drug effects , Cells, Cultured , Mutagens/toxicity , Triglycerides/metabolism
8.
J Food Sci ; 89(6): 3759-3775, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38706376

ABSTRACT

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 5.03 ng/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.


Subject(s)
Amines , Chickens , Cooking , Proanthocyanidins , Animals , Amines/chemistry , Cooking/methods , Fruit/chemistry , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/analysis , Hot Temperature , Meat Products/analysis , Proanthocyanidins/pharmacology , Proanthocyanidins/analysis , China
9.
Malays J Med Sci ; 31(2): 130-141, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38694573

ABSTRACT

Background: The objective of this study is to assess the risk of exposure of polycyclic aromatic hydrocarbons (PAHs) and heterocyclic aromatic amines (HCAs) in meat and fish-based products marketed in Malaysia using the margin of exposure (MOE) approach. Methods: Benchmark Dose (BMD) software was used to model the BMD at a lower end of a one-sided 95% confidence interval with a 10% incremental risk (BMDL10) of PAHs and HCAs from different target organ toxicities. The MOEs of PAHs and HCAs in meat and fish-based products were determined by utilising the calculated BMDL10 values and estimated daily intake of meat and fish-based products from published data. Results: The calculated BMDL10 values of PAHs (i.e. benzo[a]pyrene [BaP] and fluoranthene [FA]) and HCAs (i.e. 2-amino-3,8,dimethylimidazo[4,5-f]quinoxaline [MeIQx] and 2-amino-1-methyl-6-phenylimidazo[4,5,6]pyridine [PhIP]) ranged from 19 mg/kg bw/day to 71,801 mg/kg bw/day. The MOE of BaP ranged from 41,895 to 71,801 and that of FA ranged from 19 to 1412. As for MeIQx and PhIP, their MOEs ranged from 6,322 to 7,652 and from 2,362 to 14,390, respectively. Conclusion: The MOEs of FA, MeIQx and PhIP were lower than 10,000, indicating a high concern for human health and therefore demanding effective risk management actions.

10.
Meat Sci ; 215: 109541, 2024 Sep.
Article in English | MEDLINE | ID: mdl-38776591

ABSTRACT

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.


Subject(s)
Amines , Cooking , Meat Products , Cattle , Animals , Amines/pharmacology , Meat Products/analysis , Color , Red Meat/analysis , Sodium Chloride , Amino Acids/analysis , Lipid Peroxidation/drug effects , Sodium Chloride, Dietary
11.
Mutagenesis ; 2024 Mar 23.
Article in English | MEDLINE | ID: mdl-38520343

ABSTRACT

An ethanol extract of Piper auritum leaves (PAEE) inhibits the mutagenic effect of three food-borne aromatic amines (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP); 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx); 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx) in the TA98 Salmonella typhimurium strain. Preincubation with MeIQx demonstrated in mutagenesis experiments that inhibition of Cytochrome P450 (CYP), as well as direct interaction between component(s) of the plant extract with mutagens, might account for the antimutagenic observed effect. Gas chromatography/mass spectrometry analysis revealed that safrole (50.7%), α-copaene (7.7%), caryophyllene (7.2%), ß-pinene (4.2%), γ-terpinene (4.1%) and pentadecane (4.1%) as the main components of PAEE. Piper extract and safrole were able to inhibit the rat liver microsomal CYP1A1 activity that participates in the amines metabolism, leading to the formation of the ultimate mutagenic/ molecules. According to this, safrole and PAEE inhibited MeIQx mutagenicity but not that of the direct mutagen 2-nitrofluorene. No mutagenicity of plant extract or safrole was detected. This study show that PAEE and its main component safrole are associate with the inhibition of heterocyclic amines activation due in part to the inhibition of CYP1A subfamily activity.

12.
Food Chem ; 446: 138850, 2024 Jul 15.
Article in English | MEDLINE | ID: mdl-38452502

ABSTRACT

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.


Subject(s)
Heterocyclic Compounds , Tandem Mass Spectrometry , Animals , Sheep , Chromatography, Liquid , Tandem Mass Spectrometry/methods , Heterocyclic Compounds/analysis , Cooking/methods , Amines/analysis , Glycation End Products, Advanced/analysis
13.
Compr Rev Food Sci Food Saf ; 23(2): e13313, 2024 03.
Article in English | MEDLINE | ID: mdl-38470221

ABSTRACT

Polyphenols are well documented against the inhibition of foodborne toxicants in meat, such as heterocyclic amines, Maillard's reaction products, and protein oxidation, by means of their radical scavenging ability, metal chelation, antioxidant properties, and ability to form protein-polyphenol complexes (PPCs). However, their thermal stability, low polarity, degree of dispersion and polymerization, reactivity, solubility, gel forming properties, low bioaccessibility index during digestion, and negative impact on sensory properties are all questionable at oil-in-water interface. This paper aims to review the possibility and efficacy of polyphenols against the inhibition of mutagenic and carcinogenic oxidative products in thermally processed meat. The major findings revealed that structure of polyphenols, for example, molecular size, no of substituted carbons, hydroxyl groups and their position, sufficient size to occupy reacting sites, and ability to form quinones, are the main technical points that affect their reactivity in order to form PPCs. Following a discussion of the future of polyphenols in meat-based products, this paper offers intervention strategies, such as the combined use of food additives and hydrocolloids, processing techniques, precursors, and structure-binding relationships, which can react synergistically with polyphenols to improve their effectiveness during intensive thermal processing. This comprehensive review serves as a valuable source for food scientists, providing insights and recommendations for the appropriate use of polyphenols in meat-based products.


Subject(s)
Meat Products , Meat , Amines , Antioxidants , Carcinogens
14.
Food Chem ; 447: 138930, 2024 Jul 30.
Article in English | MEDLINE | ID: mdl-38503065

ABSTRACT

Advanced glycation end products (AGEs) and heterocyclic amines (HAs) are main harmful Maillard reaction products of meat products. Simultaneous quantification of both with high sensitivity, selectivity and accuracy remains a major challenge due to inconsistencies in their pre-treatment and instrumental methods and the different polarity of AGEs and HAs. We developed a method for the simultaneous determination of AGEs and HAs in roast/grilled meat by ultra-performance liquid chromatography coupled to tandem mass spectrometry (UPLC-MS/MS) using dynamic multiple reaction monitoring (D-MRM). The instrument parameters and pre-treatment method were optimized to achieve reasonably good separation and high response for the 11 target analytes within 8 min. From 10 to 200 ng/mL, the limits of detection (LODs) and limits of quantitation (LOQs) ranged from 0.3 to 5.5 µg/L and 0.9 to 6.3 µg/L, respectively, and the correlation coefficient (R2) was >0.99. It was acceptable to recoveries, standard deviations (RSDs), and matrix effects. Six types of roast/grilled meat samples were then tested using the developed method.


Subject(s)
Liquid Chromatography-Mass Spectrometry , Tandem Mass Spectrometry , Tandem Mass Spectrometry/methods , Chromatography, Liquid , Meat/analysis , Amines/chemistry , Glycation End Products, Advanced/analysis , Chromatography, High Pressure Liquid/methods
15.
J Sci Food Agric ; 104(7): 4083-4096, 2024 May.
Article in English | MEDLINE | ID: mdl-38323696

ABSTRACT

BACKGROUND: 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. RESULTS: 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. CONCLUSION: 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.


Subject(s)
Nitrosamines , Nitrosamines/analysis , Smoke , Amines , Neural Networks, Computer , Carcinogens
16.
Food Res Int ; 180: 114057, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38395574

ABSTRACT

The inhibitory effects of amino acids and their combinations on the formation of heterocyclic amines were investigated in this study. The great potential in the inhibition of HAs was observed in amino acid combinations compared with that of single agents. At a mass ratio of 1:1, a His-Pro combination achieved a maximum inhibitory rate of 80 %, and the total HAs content decreased to 4.70 ± 0.18 ng/g relative to the control (24.49 ± 2.18 ng/g). However, the inhibitory rate of triple combinations showed no obvious increase compared with the binary combinations. Benzaldehyde, phenylacetaldehyde, methylglyoxal, and glyoxal were positively correlated with HAs formation, and His-Pro combination (1:4) led to a significant reduction of benzaldehyde and phenylacetaldehyde at scavenging rates of 79 % and 92 %. Thus, the synergistic inhibition was achieved by simultaneously scavenging these aldehyde intermediates, and other inhibitory target, such as competition with precursors and elimination of final products can serve as supporting factors. These results provide a new perspective for approaches to enhance the suppression of HAs and control the formation of flavor compounds.


Subject(s)
Acetaldehyde/analogs & derivatives , Amino Acids , Heterocyclic Compounds , Animals , Cattle , Benzaldehydes , Amines/chemistry
17.
Foods ; 13(2)2024 Jan 05.
Article in English | MEDLINE | ID: mdl-38254486

ABSTRACT

This study aims to explore the effects of frying conditions on the formation of HAs and PAHs in crispy pork spareribs, a popular meat commodity sold on Taiwan's market. Raw pork spareribs were marinated, coated with sweet potato powder, and fried in soybean oil and palm oil at 190 °C/6 min or 150 °C/12 min, followed by an analysis of HAs and PAHs via QuEChERS coupled with UPLC-MS/MS and GC-MS/MS, respectively. Both HAs and PAHs in pork spareribs during frying followed a temperature- and time-dependent rise. A total of 7 HAs (20.34-25.97 µg/kg) and 12 PAHs (67.69-85.10 µg/kg) were detected in pork spareribs fried in soybean oil and palm oil at 150 °C/12 min or 190 °C/6 min, with palm oil producing a higher level of total HAs and a lower level of total PAHs than soybean oil. The content changes of amino acid, reducing sugar, and creatinine played a vital role in affecting HA formation, while the degree of oil unsaturation and the contents of precursors including benzaldehyde, 2-cyclohexene-1-one, and trans,trans-2,4-decadienal showed a crucial role in affecting PAH formation. The principal component analysis revealed that HAs and PAHs were formed by different mechanisms, with the latter being more liable to formation in pork spareribs during frying, while the two-factorial analysis indicated that the interaction between oil type and frying condition was insignificant for HAs and PAHs generated in crispy pork spareribs. Both CcdP (22.67-32.78 µg/kg) and Pyr (16.70-22.36 µg/kg) dominated in PAH formation, while Harman (14.46-17.91 µg/kg) and Norharman (3.41-4.55 µg/kg) dominated in HA formation in crispy pork spareribs during frying. The outcome of this study forms a basis for learning both the variety and content of HAs and PAHs generated during the frying of pork spareribs and the optimum frying condition to minimize their formation.

18.
Food Chem ; 440: 138193, 2024 May 15.
Article in English | MEDLINE | ID: mdl-38128427

ABSTRACT

The heterocyclic amine 2-amino-1-methyl-6-phenyl-imidazolium [4, 5-B] pyridine (PhIP), commonly found in roasted meat products, is considered a potential carcinogen. This study is to explore the underlying mechanisms involved in the adsorption of PhIP by lactic acid bacteria 37X-15 and its peptidoglycan. The scanning electron microscope results suggested that the strain's adsorption on PhIP occurs on the cell wall, primarily composed of peptidoglycan. The fourier-transformed infrared spectroscopy results indicated that PhIP adsorption by both lactic acid bacteria 37X-15 and its peptidoglycan primarily involved OH and NH binding groups. Different adsorption conditions affected the adsorption rate of PhIP by peptidoglycan. The optimal values for each adsorption condition were 2 h, 37 °C, and pH 6 when the maximum adsorption rate reached. This study provides a new direction for the application of lactic acid bacteria and its peptidoglycan in food safety.


Subject(s)
Imidazoles , Lactobacillales , Peptidoglycan , Lactobacillales/metabolism , Adsorption , Carcinogens/metabolism , Pyridines
19.
Food Res Int ; 175: 113639, 2024 Jan.
Article in English | MEDLINE | ID: mdl-38129016

ABSTRACT

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.


Subject(s)
Angelica , Animals , Cattle , Chromatography, Liquid , Amines , Tandem Mass Spectrometry/methods , Digestion
20.
Heliyon ; 9(11): e22183, 2023 Nov.
Article in English | MEDLINE | ID: mdl-38053851

ABSTRACT

Heterocyclic amines and acetamide derivatives are known for their chemotherapeutic potential. Hence, in the present study, morpholine was taken as a principal product and novel morpholine derivatives were designed, formulated, characterized, and screened for the mechanism of inhibition of carbonic anhydrase and their anticancer potential. In addition, in vitro inhibition of hypoxia-inducible factor-1 (HIF-1) protein was also investigated. Results revealed that compounds 1c, 1d, and 1h possessed significant inhibitory activities against carbonic anhydrase with IC50 of 8.80, 11.13, and 8.12 µM, respectively. Interestingly, the carbonic anhydrase inhibitory activity of compound 1h was comparable with that of standard acetazolamide (IC50 7.51 µM). The compounds 1h and 1i significantly inhibited the proliferation of ovarian cancer cell line ID8 with IC50 of 9.40, and 11.2 µM, respectively while the standard cisplatin exhibited an IC50 8.50 µM. In addition, compounds 1c, 1b, 1h and 1i also exhibited significant inhibitory effects on HIF-1α. In conclusion, we report first time the biological potential of morpholine based compounds against ovarian cancer and HIF-1α that may serve as lead molecules for drug discovery.

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