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

Barzegar, Fatemeh; Kamankesh, Marzieh; Mohammadi, Abdorreza

doi:10.1016/j.foodchem.2018.12.058

Cited by 158 publications

(83 citation statements)

References 121 publications

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“…β‐Carbolines including 1‐methyl‐9H‐pyrido[3,4‐b]indole (norharman) and 9H‐pyrido[3,4‐b]indole (harman) can also be formed at 100ºC (Meurillon & Engel, 2016). Studies have shown that HAAs can cause tumors in a variety of organs including liver, stomach, breast, intestines, lungs, and blood vessels (Barzegar, Kamankesh, & Mohammadi, 2019; Rahman, Sahar, Khan, & Nadeem, 2014). According to the carcinogenicity of HAAs, the International Agency for Research on Cancer (IARC) classified eight of the known HAAs (MeIQ, MeIQx, PhIP, AαC, MeAαC, Trp‐P‐1, Trp‐P‐2, and Glu‐P‐1) as possible human carcinogens (class 2B) and IQ as a probable human carcinogen (class 2A) (IARC, 1993).…”

Section: Introductionmentioning

confidence: 99%

Structure characteristics of flavonoids for heterocyclic aromatic amines inhibition using quantitative structure–activity relationship modeling

Zhao

Pan

et al. 2020

J Food Biochem

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The objective of this study was to investigate the structure characteristics of flavonoids that act as inhibitors for heterocyclic aromatic amines (HAAs) formation. Five quantitative structure–activity relationship models for predicting the inhibitory rates of HAAs (norharman, harman, PhIP, MeIQx, and 4,8‐DiMeIQx) were established using selected chemometric parameters (R2: 0.591–0.920), and indicated that the hydrophobicity, hydroxyl groups, and topological structure of flavonoids played important roles in the inhibition of HAAs formation. The 5,7‐dihydroxyls in meta‐position of the A‐ring and the 4′‐hydroxyl in the B‐ring of flavonoids were critical for the inhibitory effects of HAAs, whereas the introduction of 3‐hydroxyl and 3‐O‐glucoside in the C‐ring reduced the inhibitory effects. Catechin served as the most effective inhibitor of HAAs followed by luteolin and genistein. The study can bring us a broader idea for controlling the formation of HAAs according to the structure of flavonoids. Practical applications Heterocyclic aromatic amines (HAAs) are a class of organic substances with carcinogenic and mutagenic effect formed during the heating process of meat products. The formation of HAAs can be inhibited by adding natural antioxidants such as flavonoids to the meat during pretreatment. This inhibition is influenced by the unique structure of flavonoids. Thus, there has been an increasing demand to exploit the effective HAAs inhibitors from flavonoids by structure characteristics. Our study showed that the inhibitory effect of flavonoids on the formation of HAAs was mainly depended on their hydrophobicity, hydroxyl groups, and topological structure using the multiple QSAR models. Thus, effective HAAs inhibitors can be explored from dietary flavonoids according their structure characteristics.

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Section: Introductionmentioning

confidence: 99%

Structure characteristics of flavonoids for heterocyclic aromatic amines inhibition using quantitative structure–activity relationship modeling

Zhao

Pan

et al. 2020

J Food Biochem

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“…Although this caused a huge controversy worldwide, it is undeniable that deleterious compounds, such as heterocyclic amines (HCAs), polycyclic aromatic hydrocarbons and thermal degradation products, could be generated in meat products during heat treatment processing . Among these deleterious compounds, HCAs are considered as mutagenic substances that may cause unexpected DNA synthesis …”

Section: Introductionmentioning

confidence: 99%

“…2,3 Among these deleterious compounds, HCAs are considered as mutagenic substances that may cause unexpected DNA synthesis. 4,5 Precursors and parameters affect the formation of HCAs during heat treatment, especially the latter. 6 Different cooking methods and parameters cause diverse and specific changes on organoleptic characteristics and nutritional values, as well as harmful substances in meat products.…”

Section: Introductionmentioning

confidence: 99%

Heterocyclic amines in braised chicken may mainly infiltrate from reused marinade during braising, instead of thermic generation

Cheng

Zhou³

et al. 2020

J Sci Food Agric

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BACKGROUND Sauce braised meat products are popular in Asia, although their complicated processing may lead to potential safety risks. Especially, how hazardous compounds are formed during their preparation is still unclear. In the present study, braised chicken breasts, which are a typical Chinese sauce braised meat product, were used to investigate the formation of heterocyclic amines (HCAs) during heat treatment. RESULTS Precursor content (creatine and reducing sugar), HCA level and temperature were measured in different parts of the chicken breast at each processing stage. The results obtained showed that the increasing trends of total HCA content in different parts of chicken breast were not the same. Only total HCA content in the skin (4.93 ± 0.80 ng g−1) increased significantly after deep‐frying. During braising, total HCA level in the skin was high (12.1–14.3 ng g−1) and relatively stable. However, total HCA content in pectoralis major muscle (3.90–7.40 ng g−1) and pectoralis minor muscle (1.44–5.31 ng g−1) was much lower than in the skin, and increased steadily with braising time. CONCLUSION Braising is the main factor which affects HCA level in braised chicken. Combining the results of temperature and precursor content, a possible explanation for the large amount of HCAs in braised chicken is the gradual infiltration from reused marinade, instead of thermic generation. © 2019 Society of Chemical Industry

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“…Although lacking evidence to support the hypothesis that excessive uptake of HAs could directly cause cancer, the International Agency for Research on Cancer has already decided a limitation of HAs . HAs have been discovered in different matrices . Most of the researchers have isolated and identified them in food samples and related substances.…”

Section: Introductionmentioning

confidence: 99%

“…Most of the researchers have isolated and identified them in food samples and related substances. For instance, barbecue, roast fish, cooking residues (such as pan residues and cooking smoke), alcoholic beverages, and many other compounds have been reported to contain trace of HAs . Besides, in biological samples (such as serum, hair, bile, human milk, urine, and so on), HAs have been detected .…”

Section: Introductionmentioning

confidence: 99%

Determination of 14 heterocyclic aromatic amines in meat products using solid‐phase extraction and supercritical fluid chromatography coupled to triple quadrupole mass spectrometry

Zhang

Zhou

et al. 2020

J of Separation Science

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A novel, simple, and sensitive method has been developed for simultaneous determination of 14 heterocyclic aromatic amines in meat product using solid-phase extraction combined with ultrahigh-performance supercritical fluid chromatography coupled to tandem quadrupole mass spectrometry. The analytes could be separated within 7 min and identified using their retention times and mass. The developed method was validated based on the linearity, limits of quantification, precision, and accuracy. The recovery ranged from 52.3 to 97.5% with an acceptable standard deviation, which is not higher than 6%. The limits of quantitation ranged from 0.03 to 0.17 µg/kg. The selectivity and sensitivity were satisfactory in multiple reaction monitoring mode. The method was applied to commercial meat products, and the results demonstrated that the novel method has potential for the analysis of the targets in food matrices. This is the first work reporting the simultaneous quantification of 14 heterocyclic aromatic amines by means of ultrahigh-performance supercritical fluid chromatography coupled to tandem quadrupole mass spectrometry. K E Y W O R D Sfood-derived hazardous compounds, heterocyclic aromatic amines, meat, supercritical fluid chromatography, triple quadrupole mass spectrometry 1372

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

Cited by 158 publications

References 121 publications

Structure characteristics of flavonoids for heterocyclic aromatic amines inhibition using quantitative structure–activity relationship modeling

Structure characteristics of flavonoids for heterocyclic aromatic amines inhibition using quantitative structure–activity relationship modeling

Heterocyclic amines in braised chicken may mainly infiltrate from reused marinade during braising, instead of thermic generation

Determination of 14 heterocyclic aromatic amines in meat products using solid‐phase extraction and supercritical fluid chromatography coupled to triple quadrupole mass spectrometry

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