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LWT-FOOD SCIENCE AND TECHNOLOGY · 2025 · IF 6.6

Mechanistic insights into the inhibitory effect of resveratrol on heterocyclic amines formation involving sarcoplasmic proteins

Xiaoyue Yang,Christophe Blecker,Dequan Zhang,Zhenyu Wang

Polyphenols are effective inhibitors of heterocyclic amines (HAs), harmful compounds formed during the heating of high-protein foods such as meat. However, the mechanisms by which polyphenols affect the formation of protein-involved HAs have been rarely studied. Therefore, the inhibitory pathways and mechanisms of resveratrol on HAs formed in the presence of sarcoplasmic proteins (SP) were investigated using both a glucose/SP/creatinine model system and a reaction system containing only free HAs and SP. The findings show that resveratrol significantly reduced the content of free HAs ( P < 0.05), promoted the formation of bound HAs, and increased the levels of free amino acids after heating. Moreover, the addition of resveratrol increased the particle size and surface hydrophobicity of SP, decreased the ζ-potential, and promoted the binding and aggregation of SP and HAs. Correlation and intermolecular force analyses indicated that free HAs formed bound HAs by changing the surface hydrophobicity of SP solution, and polyphenols could affect the formation of SP-bound HAs by affecting ions and disulfide bonds. This work provides a new screening perspective and basis for HAs mitigation strategies.

CAS / MDL: 111-46-6
研究领域: 食品化学 · 生物化学 · 营养科学 · 分子生物学
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Food Chemistry-X · 2025 · IF 8.2

Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)

Mantong Zhao,Zhongyuan Liu,Mengyin Zha,Ying Sun,Haohao Shi,Xueying Zhang,Chuan Li,Guanghua Xia

The effect of aldehydes from lipid oxidation on the generation of heterocyclic amine 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) during pan-frying of golden pompano fillets was investigated. It was observed the aldehydes that contribute to thiobarbituric acid reactive substances (TBARS) value significantly promoted PhIP generation ( p  < 0.05). The defat treatment of fresh fish tissue significantly reduced the PhIP formation in pan-fried products ( p  < 0.05). During pan-frying, massive aldehydes were generated in a time-dependent manner with acrolein, propanal, hexanal, 4-hydroxy-nonenal (HNE), and 2,4-decadienal (DDE) as the abundant species. In the established chemical model, these aldehydes congruously promoted PhIP formation with the increased concentration, especially acrolein, HNE and DDE. Therefore, aldehydes could significantly enhance the PhIP generation under processing. However, except for propanal and hexanal, the promoting effect was slightly decreased with high levels of aldehydes addition due to the strong electrophilic properties and participation of reaction with the amino group of phenylacetaldehyde, creatinine, even PhIP.

研究领域: 食品科学 · 毒理学
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Food Bioscience · 2022 · IF 5.318

Processing stage-guided effects of spices on the formation and accumulation of heterocyclic amines in smoked and cooked sausages

Diaodiao Yang,Zhiyong He,Zhaojun Wang,Qin Fang,Fatih Oz,Jie Chen,Maomao Zeng

Heterocyclic amines (HAs) could be generated though sausage processing. The results showed that garlic, black pepper, chili inhibited the formation of HAs (584.29 ng/g, 613.11 ng/g, 677.23 ng/g) whereas ginger and Sichuan pepper intensified (965.66 ng/g, 916.59 ng/g) compare with control sausage 863.86 ng/g. Furthermore, the study showed that garlic, black pepper, chilli all inhibited the formation of total HAs at stage of raw, drying, baking and steaming and had different inhibitory effect at every stage. Black pepper had the best inhibitory effect across four stages and inhibition rate reached 65%, 69%, 66%, 84% after each stage. Chilli was the only one had inhibitory effect on both free and protein-bound HAs at every stage and inhibition rate about free and protein-bound HAs reached 38% and 76% in finished sausage. Adding certain spices properly during processing would be helpful to obtain fewer HAs in sausage.

CAS / MDL: 75-05-8 141-78-6 67-56-1
研究领域: 食品科学 · 生物化学
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FOOD CHEMISTRY · 2021 · IF 7.514

Chlorogenic acid and Epicatechin: An efficient inhibitor of heterocyclic amines in charcoal roasted lamb meats

Xiaoqian Ding,Dequan Zhang,Huan Liu,Zhenyu Wang,Teng Hui

There are few studies on controlling the formation of heterocyclic amines (HAs) by adding polyphenols to roasted lamb. The aim of this study was to assess the inhibitory effect of 0.025, 0.125, and 0.625 mmol of chlorogenic acid, epicatechin, rutin, quercetin and quinic acid on the formation of HAs in charcoal roasted lamb, respectively, by UHPLC-MS/MS. The results indicated that Harman, Norharman, PhIP, IQx and 8-MeIQx were detected, but both chlorogenic acid and epicatechin greatly inhibited the formation of IQx, 8-MeIQx, Norharman, Harman and PhIP, and epicatechin had better inhibitory effect than chlorogenic acid. PLSR-VID analysis suggested the key precursors of HAs formation in roasted lamb were glucose, ribose, fructose, isoleucine, valine, and lysine. In addition, this work also implied that the potential mechanism of inhibition of HAs formation by chlorogenic acid and epicatechin in roasted lamb might attribute to competitive chemical reactions between polyphenols and key precursors of HAs.

研究领域: 食品科学 · 生物化学
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Foods · 2022 ·Vol. 11 ·期 23 ·3767 · IF 5.561

Inhibiting Effects of Ginger and Rosemary on the Formation of Heterocyclic Amines, Polycyclic Aromatic Hydrocarbons, and Trans Fatty Acids in Fried Pork Balls

Xiaomei He,Baichenyang Li,Xiaoyan Yu,Yuan Zhuang,Changmo Li,Lu Dong,Yan Zhang,Shuo Wang

The preparation of fried meat products is prone to the formation of large amounts of heterocyclic amines (HCAs), polycyclic aromatic hydrocarbons (PAHs), and trans fatty acids (TFAs), which are potential risks to human health. Spices contain natural antioxidants that can inhibit the oxidation of fats and oils and the formation of hazardous substances. In this experiment, the effect of adding different levels (0.25%, 0.75%, 1.25%) of ginger or rosemary during meatball preparation on the formation of HCAs, PAHs and TFAs in fried pork balls was investigated. The results showed that the addition of ginger and rosemary reduced the content of HCAs in fried pork balls compared to the control group (no added spices). The inhibition of total HCAs was 63% when 0.25% ginger was added, while the total HCA content was reduced to 59% when 0.25% rosemary was added. The addition of 0.25% and 0.75% rosemary reduced the PAH content in fried pork balls by 30% and 35%. In addition, ginger and rosemary showed significant inhibition of C20:1 11t in TFAs, with a maximum inhibition rate of 40%. Therefore, adding appropriate levels of ginger or rosemary to fried pork balls could simultaneously inhibit the formation of HCAs, PAHs, and TFAs.Keywords:heterocyclic amines;polycyclic aromatic hydrocarbons;trans fatty acids;inhibitory profile;antioxidant

研究领域: 食品科学 · 营养学 · 毒理学
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MOLECULES · 2023 ·Vol. 28 ·期 20 ·7012 · IF 4.6

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

Jingjing Yu,Xiaohui Yu,Lili Shi,Wei Liu

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) andNε-(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.Keywords:advanced glycation end products;heterocyclic amines;peanut;roasting;correlation analysis

CAS / MDL: 99-56-9
研究领域: 食品科学 · 营养学
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Food Bioscience · 2024 · IF 4.8

Mechanism of four dihydroflavones inhibiting heterocyclic amine formation in roasted pork patties―increasing the moisture

Yangyang Wang,Haolin Zhang,Lei Chen,Hui Teng,Hui Wang,Hui Cao

This study explored the inhibitory effect and mechanisms of four dihydroflavones (hesperetin, hesperidin, naringenin and naringin) addition on the production of five HCAs (IQ, DMIP, MeIQx, Norharman and PhIP) in roasted pork patties. Results indicated that the moisture holding capacity of dihydroflavones played a crucial role in their inhibition on HCA formation. The importance of moisture in the HCA formation was further confirmed by adding two water-retaining edible starches (corn and sweet potato starch). Significantly, the combination of edible starch and naringenin resulted in better inhibition of HCAs. The inhibition ratio of the mixture containing corn starch and naringenin on IQ, DMIP, MeIQx, Norharman and PhIP of pork patties were even up to 76.64%, 100%, 53.29%, 91.29% and 100%, respectively. This study offers a new idea of combination of dihydroflavone and edible starch to better control the HCA formation in roasted meat products.

研究领域: 食品科学 · 营养学 · 致癌作用
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Foods · 2025 ·Vol. 14 ·期 2 ·299 · IF 5.1

The Effect of Cumin on the Formation of β-Carboline Heterocyclic Amines in Smoked Meat and Simulated Systems

Xiuxiu Liu,Wenyu Chen,Minghao Sun,Xufang Lv,Xing Shen,Zhongping Chai,Maomao Zeng

In this study, we aimed to investigate the inhibitory effects of cumin and cumin extracts from different origins (Hami, Turpan, and Hetian) on the formation ofβ-carboline heterocyclic amines (HCAs) in smoked meat and simulated systems, and to assess their potential as natural inhibitors in the food industry. The novelty of our research lies in the comprehensive comparative analysis of cumin extracts from different origins, which has not been fully explored in previous studies. We first conducted a quantitative analysis of the total phenol and flavonoid content in cumin extracts from the three origins and evaluated their antioxidant capacities. Subsequently, through simulation experiments, we assessed the inhibitory effects of these extracts on the formation ofβ-carboline heterocyclic amines and determined their free radical scavenging abilities. To further validate the practical application potential of these extracts, we prepared meat patty samples containing different concentrations of cumin powder, simulating actual processing conditions. The experimental results showed that while the total phenol content in cumin extracts from all origins was similar, averaging around 1.56 mg/g, there was a significant difference in the total flavonoid content, with the highest level observed in the Hetian cumin extract at 6.7 mg/g. Additionally, the Hetian cumin extract demonstrated superior antioxidant capacity, with an FRAP antioxidant activity reaching 21.04 μM TE/g dw, the highest among all samples. Our study also found that the inhibitory effect of cumin extracts on HCA formation was closely related to their free radical scavenging ability, with the Hetian cumin extract showing the strongest scavenging capacity. The addition of cumin powder to meat patties significantly reduced the content ofβ-carboline heterocyclic amines, particularly at lower cumin concentrations. In summary, our research results highlight the potential of cumin, especially from Hetian, as a natural inhibitor ofβ-carboline heterocyclic amine formation in processed meats. This study not only provides the food industry with a potential natural additive to improve food safety and quality, but also offers new directions for future research, namely by comparing natural plant extracts from different origins to explore their potential applications in food processing.

CAS / MDL: 2896-70-0
研究领域: 食品科学 · 生物化学
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Food Frontiers · 2023 ·Vol. 4 ·期 4 ·1913-1926 · IF 9.9

Coupled adsorption and photocatalysis: A green synthesized g-C3N4@Mn–FeOOH@molecularly imprinted photocatalysis system for targeted removal of various heterocyclic amines

Chun-Yang Li,Lu Yang,Yingshuang Lu,Man-Man Wang,Jing-Min Liu,Shuo Wang

Photocatalysis-based advanced oxidation technologies have been developed as an attractive strategy for degrading pollutants. However, the question of how to increase removal specificity without sacrificing the degradation effect remains a difficult one. In this work, a photocatalytic system for the simultaneous targeted elimination of nine heterocyclic amines (HCAs) is established using a green-prepared photocatalyst (CN@Mn–FeOOH@MIP) that activates sodium persulfate (PS) under visible light. Mn–FeOOH clusters are in situ covered on laminar g-C 3 N 4 (CN) carrier to form a heterojunction, along with a molecularly imprinted layer self-polymerized from dopamine, which is grown on the outer layer, resulting in both the desired photochemical activity and specific sites for recognition. The conditions of composite and photocatalysis are explored and optimized for efficient and selective degradation. Notably, CN@Mn–FeOOH@MIP is synthesized free of any organic reagents, and the biosafety is confirmed by cellular and in vivo toxicity evaluation. The developed CN@Mn–FeOOH@MIP/PS system with visible-light-driven is applied to the removal of HCAs in coffee samples with the recoveries over 70% and the reuse rates greater than 85%. It coupled the advantages of specific enrichment and rapid degradation, which furnishes a novel approach for the control of trace thermal processing pollutants.

研究领域: 环境科学 · 材料科学 · 食品安全
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FOOD CHEMISTRY · 2025 · IF 9.8

Synergistic inhibition of Maillard reaction hazards: Multifunctional hydrocolloids enable healthier air-fried beef patties with reduced heterocyclic amines and AGEs

Hongfei Du,Huang Zhang,Zixin Zhang,Zihan Yuan,Maiquan Li,Lei Zhou,Yan Liu,Aihua Lou,Mei Li,Ye Jiao,Qingwu Shen,Chaoyi Xue,Wei Quan,Lan Mo

The growing health consciousness of consumers has led the food industry to embrace healthier cooking methods, with air frying becoming increasingly popular in households. This study investigated the dual role of 10 hydrocolloids in reducing the formation of heterocyclic amines (HAs) and advanced glycation end products (AGEs) in air-fried beef patties while preserving physicochemical and sensory qualities. Marination with hydrocolloids at concentrations of 0.1–1.0 % mitigated lipid/protein oxidation, retained moisture, improved texture, and significantly inhibited HA (26.3–55.4 %) and AGE (21.3–51.1 %) formation. Among the hydrocolloids, chitosan (0.5 % and 1.0 %) demonstrated optimal efficacy, reducing HAs and AGEs contents by 48.8–55 % and 42.4–47.2 %, respectively with limited effects on the key flavor compound. Mechanistically, hydrocolloids formed protective matrices, scavenged free radicals, and reacted with Maillard reaction intermediates. These findings provide actionable insights for developing safer air-fried meat products without compromising quality, addressing critical public health concerns related to dietary carcinogens.

研究领域: 食品科学 · 营养学 · 公共卫生
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ANALYTICA CHIMICA ACTA · 2021 · IF 6.558

UiO-66 metal-organic frameworks/gold nanoparticles based substrates for SERS analysis of food samples

Jingtai Fu,Huasheng Lai,Zhuomin Zhang,Gongke Li

Recently, metal-organic frameworks (MOFs) based substrates have shown great potential for the quantitative analysis of food samples by surface-enhanced Raman scattering (SERS) due to their unique properties. Herein, we developed two UiO-66 MOFs/gold nanoparticles (AuNPs) based substrates by self-assembly, including UiO-66/AuNPs suspension substrate and UiO-66(NH 2 )/AuNPs/Nylon-66 flexible membrane substrate, for quantitative analysis of complex food samples by SERS. UiO-66/AuNPs suspension substrate was prepared for SERS-based determination of a carcinogenic heterocyclic amine in barbecue meat. UiO-66(NH 2 )/AuNPs/Nylon-66 membrane substrate was fabricated for the simultaneous separation, enrichment, and in situ analysis of Sudan Red 7B in chilli products. The heterocyclic amine and Sudan dye in real samples could be detected and quantified with the recoveries of 82.3–110% and 84.5–114% and relative standard deviations (RSDs) of 3.1–11.0% and 1.9–5.6% (n = 3) by use of these two substrates, respectively. These two UiO-66/AuNPs based substrates combined molecular enrichment and SERS activity, achieving excellent analytical accuracy and widening SERS application in practical food safety analysis.

研究领域: 分析化学 · 食品安全 · 纳米材料科学
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Polymers · 2023 ·Vol. 15 ·期 19 ·3914 · IF 5

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

Hongfei Du,Tiantian Huang,Maomao Zeng,Qingwu Shen,Ye Jiao,Wei Quan

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.Keywords:hydrocolloids;chemical model system;heterocyclic amines;advanced glycation end products;grilled beef patties

研究领域: 食品科学 · 营养学 · 生物化学
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