DOCSLIB.ORG

Preventive Potential and Mechanism of Dietary Polyphenols on the Formation of Heterocyclic Aromatic Amines

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Preventive Potential and Mechanism of Dietary Polyphenols on the Formation of Heterocyclic Aromatic Amines Received: 1 June 2020 Revised: 19 June 2020 Accepted: 19 June 2020 DOI: 10.1002/fft2.30 REVIEW ARTICLE Preventive potential and mechanism of dietary polyphenols on the formation of heterocyclic aromatic amines Hui Cao1 Bing-Huei Chen2 Baskaran Stephen Inbaraj2 Lei Chen1 Gerardo Alvarez-Rivera3 Alejandro Cifuentes3 Nana Zhang4 Deng-Jye Yang5 Jesus Simal-Gandara6 Mingfu Wang4 Jianbo Xiao7 1 College of Food Science, Fujian Agriculture and Forestry University, Fuzhou, Fujian, China 2 Department of Food Science, Fu Jen Catholic University, New Taipei City, Taiwan 3 Laboratory of Foodomics, Institute of Food Science Research, CIAL, CSIC, Madrid, Spain 4 School of Biological Sciences, The University of Hong Kong, Hong Kong 5 Institute of Food Safety and Health Risk Assessment, National Yang-Ming University, Taipei, Taiwan 6 Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo-Ourense Campus, Ourense, Spain 7 Institute of Food Safety and Nutrition, Jinan University, Guangzhou, China Correspondence Jianbo Xiao, Institute of Food Safety and Nutri- Abstract tion, Jinan University, Guangzhou 510632, China. Thermal processing is the most important and popular domestic cooking method. More Email: [email protected] than 30 heterocyclic aromatic amines have been identified in cooked meat using var- Mingfu Wang, School of Biological Sciences, The University of Hong Kong, Pokfulam Road, ious methods. This review highlights preventive potential and mechanism of dietary Hong Kong. polyphenols on the formation of heterocyclic amines. Tea, coffee, fruits, vegetable, and Email: [email protected] Jesus Simal-Gandara, Nutrition and Bromatol- spice extracts rich in polyphenols exerted significant inhibition against the formation of ogy Group, Department of Analytical Chem- heterocyclic aromatic amines. Some polyphenols, such as naringenin and epigallocate- istry and Food Science, Faculty of Food Science and Technology, University of Vigo-Ourense chin 3-O-gallate, can actively participate into food chemistry reaction to trap Strecker Campus, E-32004 Ourense, Spain. aldehyde and lower the formation of heterocyclic aromatic amines. In addition, some Email: [email protected] polyphenols can lower the mutagenicity of heterocyclic aromatic amines. More specif- ically, polyphenols possessing two hydroxyl groups at the meta position of aromatic ring are the most efficient one, but the presence of carboxylic or alkyl groups as sub- stituents in the aromatic ring slightly reduced the inhibitory effect. KEYWORDS heterocyclic aromatic amines, inhibition, polyphenols, structure–activity relationship This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. © 2020 The Authors. Food Frontiers published by John Wiley & Sons Australia, Ltd and Nanchang University, Northwest University, Jiangsu University, Zhejiang Univer- sity, Fujian Agriculture and Forestry University 134 wileyonlinelibrary.com/journal/fft2 Food Frontiers. 2020;1:134–151. CAO ET AL. 135 1 HAZARDS LINKED TO FOOD THERMAL 2 FORMATION OF HETEROCYCLIC AROMATIC PROCESSING AMINES Thermal processing is the most important and popular domestic The formation pathways of HAAs are usually investigated in chemi- cooking method. It has many benefits such as improving nutri- cal model systems to reduce side reactions and exclude the effects tional quality, enhancing bioavailability of nutrients, prolonging of other components. According to the structure differences and for- shelf life, obtaining better flavor, producing bioactive compounds, mation pathway, HAAs can be divided into aminoimidazoazarenes and improving food safety (Zhao et al., 2019). On the other hand, (AIAs) and pyrolytic HAAs. AIAs include quinoxalines (IQx, MeIQx, it can also bring some undesired consequences including losing DiMeIQx, etc.), quinolines (IQ, MeIQ, etc.), and pyridines (PhIP, DMIP, nutrients, forming toxic compounds, causing unpleasant flavor, etc.), while pyrolytic HAAs mainly include α-carbolines (AαC, MeAαC), and so on (Friedman, 2015; Mogol & Gokmen, 2016). In particular, β-carbolines (harman and norharman), γ-carbolines (Trp-P-1, Trp-P-2), the mutagenic compounds, such as acrylamide, acrolein, polycyclic δ-carbolines (Glu-P-1, Glu-P-2), and phenyl pyridine (Phe-P-1) (Bus- aromatic hydrocarbons (PAHs), and heterocyclic aromatic amines quets, Bordas, Toribio, Puignou, & Galceran, 2004; Kizil, Oz, & Besler, (HAAs), are formed during the thermal processing of various foods 2011). (Fasano, Yebra-Pimentel, Martinez-Carballo, & Simal-Gandara, 2016; Garcia-Falcon & Simal-Gandara, 2005; Rey-Salgueiro, Garcia-Falcon, Martinez-Carballo, Gonzalez- Barreiro & Simal-Gandara, 2009;Rey- 2.1 Formation of quinoxalines and quinolines Salgueiro, Garcia-Falcon, Martinez-Carballo, & Simal-Gandara, 2008, HAAs Rey-Salgueiro, Garcia-Falcon, Martinez-Carballo, & Simal-Gandara, 2009; Singh, Agarwal, & Simal-Gandara, 2020; Viegas, Yebra-Pimentel, AIAs are mainly formed by dehydration and cyclization of amino acids Martinez-Carballo, Simal-Gandara, & Ferreira, 2014; Yebra-Pimentel, and sugars at temperatures between 100 and 300◦C to form pyrrole Fernandez-Gonzalez, Martinez-Carballo, & Simal-Gandara, 2012; or pyrazine, and then condensation with creatinine and aldehydes Yebra-Pimentel, Martinez-Carballo, Regueiro, & Simal-Gandara, produced by Strecker degradation (Kizil et al., 2011). Specifically, as for 2013). More than 30 HAAs compounds (Figure 1) have been identified the formation of IQ-type HAAs, an early study has proposed a possible in cooked meat using various methods. HAAs compounds can be pathway, as shown in Figure 2, creatinine forms the aminoimidazole classified into thermic and pyrolytic types according to their formation part through cyclization and dehydration, while the remaining part of temperature. The thermic HAAs with a chemical structure of aminoim- IQ-type HAAs is derived from Strecker degradation products such as idazoazarene are commonly formed under relative low temperatures pyridine and pyrazine. The two parts are then linked by butyraldehyde (∼200◦C), and the pyrolytic HAAs (mainly amino-carbolines) are pro- condensation via Strecker reaction products such as aldehyde or duced by pyrolysis of amino acids and proteins at higher temperatures Schiff base (Jägerstad, Reuterswärd, Olsson, et al. 1983; Jägerstad, (250◦C) (Zamora & Hidalgo, 2020). Reuterswärd, Öste et al., 1983). This pathway was further validated The levels of specific HAAs compounds are different with the meat and refined by Nyhammar (1986). However, Jones and others believed type, cooking method, temperature, time, and doneness level. Other that in the case of the same precursors, creatinine might condense factors are determined by the various food substrates, including pH, with aldehyde first before reacting with pyridine or pyrazine to form IQ contents of precursors, presence of certain divalent ions, types of or IQx compounds (Jones & Weisburger, 1988). Subsequently, Pearson amino acids, and content of substances with enhancing or inhibit- and others proposed two free radical pathways (Figure 2), which ing effects (Gibis, 2016). The imidazo moiety is originated from the suggest that alkylpyridine free radicals react with creatinine to form creatinine; moreover, if the creatinine is absent, no imidazoquinoline IQ and MeIQ, while MeIQx and 4,8-DiMeIQx are formed between and imidazoquinoxaline are formed. However, the generation of the dialkylpyrazine free radicals and creatinine. Specifically, the former pyrolytic HAAs does not require the existence of creatinine. PhIP involves bimolecular ring formation from the enaminol form of the appears to be formed more easily in chicken than in beef, pork or glycoaldehyde alkylamine and followed by the oxidative formation of fish, while the amount of MeIQx in cooked chicken is usually lower free radicals. The later involves N,N1-diakylpyrasinium ions formation than in cooked beef and pork. For a given cooking condition, the from glyoxal monoalkylamine and then form the free radicals through amount of PhIP, MeIQx, and AαC in ordinary muscle was higher than reduction (Pearson, Chen, Gray, & Aust, 1992). the dark muscle. It also can be observed that less browning inten- sity on the meat surface of the dark muscle than the ordinary mus- cle, enhances the formation of HAAs. Moreover, the ordinary muscle 2.2 Formation of pyridines HAAs contains higher free amino acids, moisture, and nitrogen compounds than dark muscle, which also facilitate the formation of carcinogenic Phenylalanine and creatinine have been confirmed to be the precursors HAAs. of PhIP formation via 13C labeling method, while glucose was found not 136 CAO ET AL. FIGURE 1 Chemical structures of heterocyclic amines formed during food processing CAO ET AL. 137 FIGURE 2 Proposed pathways for the formation of quinoxalines (IQx, MeIQx, DiMeIQx, etc.) and quinolines (IQ, MeIQ, etc.) HAAs a necessary precursor under dry heating conditions and excessive glu- nitrogen, and benzene ring of phenylalanine, as well as the amino nitro- cose may inhibit PhIP formation to a certain extent (Felton & Knize, gen and the nitrogen atom in the ring of creatine all participate in the 1990; Skog, Johansson, & Jägerstad, 1998). The formation of PhIP in formation of PhIP. Therefore,
Load more

Recommended publications
  • Heterocyclic Amine Content of Pork Products Cooked by Different
    Food and Chemical Toxicology 36 (1998) 289±297 Heterocyclic Amine Content of Pork Products Cooked by Dierent Methods and to Varying Degrees of Doneness R. SINHA1*, M. G. KNIZE2, C. P. SALMON2, E. D. BROWN3, D. RHODES3, J. S. FELTON2, O. A. LEVANDER3 and N. ROTHMAN1 1Division of Cancer Epidemiology and Genetics, National Cancer Institute, National Institutes of Health, Executive Plaza North, Rm 430, 6130 Executive Blvd, Rockville, MD 20892, 2Biology and Biotechnology Research Program, Lawrence Livermore National Laboratory, University of California, Livermore, CA 94550 and 3Nutrient Requirements and Functions Laboratory, BHNRC, ARS, United States Department of Agriculture, 10300 Baltimore Ave, Beltsville, MD 20705-2350, USA (Accepted 1 October 1997) AbstractÐHeterocyclic amines (HCAs) are known mutagens and animal carcinogens produced in meats cooked at high temperature. As pork is the second most frequently consumed meat in the United States, ®ve predominant HCAs [2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,4-dimethyl- imidazo[4,5-f]quinoline (MeIQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3,4,8- trimethylimidazo[4,5-f]quinoxaline (DiMeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)] were measured in various pork products, cooked by dierent techniques and to varying done- ness levels. Pork chops and ham slices were pan-fried and oven-broiled; bacon was pan-fried, oven- broiled or microwaved; hot dogs were pan-fried, oven-broiled, grilled/barbecued or boiled; sausage links and patties were pan-fried. All the products were cooked to three levels of doneness: just until done, well done or very well done.
    [Show full text]
  • Heterocyclic Amine Content in Commercial Ready to Eat Meat Products
    ÔØ ÅÒÙ×Ö ÔØ Heterocyclic amine content in commercial ready to eat meat products Kanithaporn Puangsombat, Priyadarshini Gadgil, Terry A. Houser, Melvin C. Hunt, J. Scott Smith PII: S0309-1740(10)00455-9 DOI: doi: 10.1016/j.meatsci.2010.12.025 Reference: MESC 5281 To appear in: Meat Science Received date: 26 July 2010 Revised date: 3 December 2010 Accepted date: 14 December 2010 Please cite this article as: Puangsombat, K., Gadgil, P., Houser, T.A., Hunt, M.C. & Smith, J.S., Heterocyclic amine content in commercial ready to eat meat products, Meat Science (2010), doi: 10.1016/j.meatsci.2010.12.025 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. ACCEPTED MANUSCRIPT Heterocyclic Amine Content in Commercial Ready to Eat Meat Products a b c Kanithaporn Puangsombat , Priyadarshini Gadgil , Terry A. Houser , c c Melvin C. Hunt , J. Scott Smith a Department of Food Science and Technology, Faculty of Agro-Industry, Kasetsart University, Bangkok, Thailand, 10900 b United States Department of Agriculture, Agricultural Research Service, Manhattan, Kansas 66502 c The Department of Animal Sciences and Industry, Kansas State University, Manhattan, Kansas 66506 contact information for corresponding author: J. Scott Smith Animal Sciences & Industry 208 Call Hall Kansas State University Manhattan, KS 66506 (785) 532-1219 Fax: (785) 532-5681 E-mail: [email protected] ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT ABSTRACT Heterocyclic amines (HCAs) are produced in meats cooked at high temperature, which are potent mutagens and a risk factor for human cancers.
    [Show full text]
  • Review Article Food Processing and Maillard Reaction Products: Effect on Human Health and Nutrition
    Hindawi Publishing Corporation International Journal of Food Science Volume 2015, Article ID 526762, 6 pages http://dx.doi.org/10.1155/2015/526762 Review Article Food Processing and Maillard Reaction Products: Effect on Human Health and Nutrition Nahid Tamanna1 and Niaz Mahmood2 1 Graduate Program in Biological Sciences, University of Manitoba, Winnipeg, MB, Canada R3T 2N2 2Graduate Program in Biochemistry and Medical Genetics, University of Manitoba, Winnipeg, MB, Canada R3E 0J9 Correspondence should be addressed to Nahid Tamanna; [email protected] Received 28 July 201; Revised 18 December 201; Accepted 2 December 201 Academic Editor: Mitsuru Yoshida Copyright © 2015 N. Tamanna and N. Mahmood. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Maillard reaction produces flavour and aroma during cooking process; andt i is used almost everywhere from the baking industry to our day to day life to make food tasty. It is often called nonenzymatic browning reaction since it takes place in the absence of enzyme. When foods are being processed or cooked at high temperature, chemical reaction between amino acids and reducing sugars leads to the formation of Maillard reaction products (MRPs). Depending on the way the food is being processed, both beneficial and toxic MRPs can be produced. Therefore, there is a need to understand the different typess ofMRP and their positive or negative health effects. In this review we have summarized how food processing effects MRP formation in some of the very common foods.
    [Show full text]
  • Cooked Meat Danger
    CANCER FACTS N a t i o n a l C a n c e r I n s t i t u t e • N a t i o n a l I n s t i t u t e s o f H e a l t h D e p a r t m e n t o f H e a l t h a n d H u m a n S e r v i c e s Heterocyclic Amines in Cooked Meats Research has shown that cooking certain meats at high temperatures creates chemicals that are not present in uncooked meats. A few of these chemicals may increase cancer risk. For example, heterocyclic amines (HCAs) are the carcinogenic chemicals formed from the cooking of muscle meats such as beef, pork, fowl, and fish. HCAs form when amino acids (the building blocks of proteins) and creatine (a chemical found in muscles) react at high cooking temperatures. Researchers have identified 17 different HCAs resulting from the cooking of muscle meats that may pose human cancer risk. Research conducted by the National Cancer Institute (NCI) as well as by Japanese and European scientists indicates that heterocyclic amines are created within muscle meats during most types of high temperature cooking. Recent studies have further evaluated the relationship associated with methods of cooking meat and the development of specific types of cancer. One study conducted by researchers from NCI’s Division of Cancer Epidemiology and Genetics found a link between individuals with stomach cancer and the consumption of cooked meats.
    [Show full text]
  • Mutagenicity of Heterocyclic Amines by Biomimetic Chemical Models for Cytochrome P450 in Ames Assay
    Genes and Environment, Vol. 32, No. 1 pp. 7–13 (2010) Regular article Mutagenicity of Heterocyclic Amines by Biomimetic Chemical Models for Cytochrome P450 in Ames Assay Keiko Inami1,2, Minako Nagao1,3,SatokoIshikawa1,3 and Masataka Mochizuki1,2 1Kyoritsu University of Pharmacy, Tokyo, Japan 2Faculty of Pharmaceutical Sciences, Tokyo University of Science, Chiba, Japan 3Faculty of Pharmacy, Keio University, Tokyo, Japan (Received December 26, 2009; Revised January 25, 2010; Accepted January 26, 2010) Heterocyclic amines (HCAs) are a family of mutagenic tion or intake of HCAs is suspected to be correlated and carcinogenic compounds produced during cooking or with the induction of cancers (7–13). HCAs are a family other burning processes, and exist in the environment. of mutagenic and carcinogenic compounds produced HCAs are metabolically activated by cytochrome P450, during the pyrolysis of creatine, amino acids and glu- conjugated by phase II enzymes, to react with guanine cose. HCAs are classiˆed into two groups based on bases. The aim of this study is to establish a chemical structure: 2-amino-3-methylimidazo[4,5-f]quinoline model for cytochrome P450 as an alternative to S-9 mix for detecting HCA mutagenicity in Salmonella strain. A (IQ)-type and non-IQ type. IQ-type comprises HCAs chemical model was developed by comparing the muta- that are characterized by a 2-aminoimidazole structure, genicity of 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp- while non-IQ type is typically characterized by a 2- P-2) in the presence of an iron porphyrin and an oxidant. aminopyridine structure (14–16) (Fig.
    [Show full text]
  • Formation and Human Risk of Carcinogenic Heterocyclic Amines Formed from Natural Precursors in Meat
    UCRL-JRNL-208240 Formation and Human Risk of Carcinogenic Heterocyclic Amines Formed from Natural Precursors in Meat M. G. Knize, J. S. Felton November 30, 2004 Nutrition Reviews Disclaimer This document was prepared as an account of work sponsored by an agency of the United States Government. Neither the United States Government nor the University of California nor any of their employees, makes any warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer, or otherwise, does not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government or the University of California. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States Government or the University of California, and shall not be used for advertising or product endorsement purposes. Special Nutrition Article Formation and Human Risk of Carcinogenic Heterocyclic Amines Formed from Natural Precursors in Meat Mark G. Knize and James S. Felton Biology and Biotechnology Research Program University of California Lawrence Livermore National Laboratory, Livermore, CA 94551 Corresponding author: Email:[email protected] Phone 926 422 5656 Fax 925 422 2282 Header: Heterocyclic amines from meat Keywords: Heterocyclic amine, PhIP, IFP, cooked meat, epidemiology This work was performed under the auspices of the U.S. Department of Energy by the University of California, Lawrence Livermore National Laboratory under Contract No.
    [Show full text]
  • Meat Consumption, Heterocyclic Amines, NAT2 and the Risk of Breast Cancer
    Meat consumption, heterocyclic amines, NAT2 and the risk of breast cancer The Harvard community has made this article openly available. Please share how this access benefits you. Your story matters Citation Mignone, Laura, Edward Giovannucci, Polly Newcomb, Linda Titus- Ernstoff, Amy Trentham-Dietz, John Hampton, E. John Orav, Walter Willett, and Kathleen Egan. 2009. “Meat Consumption, Heterocyclic Amines, NAT2, and the Risk of Breast Cancer.” Nutrition and Cancer 61 (1): 36–46. https://doi.org/10.1080/01635580802348658. Citable link http://nrs.harvard.edu/urn-3:HUL.InstRepos:41392094 Terms of Use This article was downloaded from Harvard University’s DASH repository, and is made available under the terms and conditions applicable to Other Posted Material, as set forth at http:// nrs.harvard.edu/urn-3:HUL.InstRepos:dash.current.terms-of- use#LAA HHS Public Access Author manuscript Author ManuscriptAuthor Manuscript Author Nutr Cancer Manuscript Author . Author manuscript; Manuscript Author available in PMC 2016 June 10. Published in final edited form as: Nutr Cancer. 2009 ; 61(1): 36–46. doi:10.1080/01635580802348658. Meat consumption, heterocyclic amines, NAT2 and the risk of breast cancer Laura I. Mignone, Department of Epidemiology, Harvard School of Public Health, Boston, Massachusetts, USA Edward Giovannucci, Department of Epidemiology and Department of Nutrition, Harvard School of Public Health, Boston, Massachusetts, USA Polly A. Newcomb, Fred Hutchinson Cancer Research Center, Seattle, Washington, and University of Wisconsin Paul P. Carbone Comprehensive Cancer Center, Madison, Wisconsin, USA Linda Titus-Ernstoff, Department of Community and Family Medicine, Dartmouth Medical School, Lebanon, New Hampshire, USA Amy Trentham-Dietz, University of Wisconsin Paul P.
    [Show full text]
  • Heterocyclic Amines
    Report on Carcinogens, Fourteenth Edition For Table of Contents, see home page: http://ntp.niehs.nih.gov/go/roc Heterocyclic Amines (Selected) Carcinogenicity MeIQ is reasonably anticipated to be a human carcinogen based on Also known as HCAs sufficient evidence of carcinogenicity from studies in experimental Introduction animals and supporting genotoxicity data. Heterocyclic amines (HCAs) are formed during the cooking of meat, Cancer Studies in Experimental Animals by condensation of creatinine with amino acids. Four individual Oral exposure to MeIQ caused tumors at several different tissue sites HCAs are listed in the Report on Carcinogens as reasonably antici- in mice and rats. In mice of both sexes, MeIQ increased the com‑ pated to be a human carcinogen (in separate listings): bined incidence of benign and malignant forestomach tumors (pap‑ • 2‑Amino‑3,4‑dimethylimidazo[4,5‑f]quinoline (MeIQ) was illoma, squamous‑cell carcinoma, and sarcoma). In female mice, it first listed in the Eleventh Report on Carcinogens (2004). also caused cancer of the cecum and colon (adenocarcinoma) and • 2‑Amino‑3,8‑dimethylimidazo[4,5‑f]quinoxaline (MeIQx) was increased the combined incidence of benign and malignant liver tu‑ first listed in the Eleventh Report on Carcinogens (2004). mors (fibrosarcoma and hepatocellular adenoma and carcinoma). In • 2‑Amino‑3‑methylimidazo[4,5‑f]quinoline (IQ) was first listed rats of both sexes, MeIQ increased the combined incidence of be‑ in the Tenth Report on Carcinogens (2002). nign and malignant colon tumors (adenoma and adenocarcinoma) • 2‑Amino‑1‑methyl‑6‑phenylimidazo[4,5‑b]pyridine (PhIP) and caused cancer of the oral cavity and Zymbal gland (squamous‑ was first listed in the Eleventh Report on Carcinogens (2004).
    [Show full text]
  • Research Section Heterocyclic Amine Content in Beef Cooked by Different
    Food and Chemical Toxicology 36 (1998) 279±287 Research Section Heterocyclic Amine Content in Beef Cooked by Dierent Methods to Varying Degrees of Doneness and Gravy made from Meat Drippings R. SINHA1*, N. ROTHMAN1, C. P. SALMON2, M. G. KNIZE2, E. D. BROWN3, C. A. SWANSON1, D. RHODES3, S. ROSSI4, J. S. FELTON2 and O. A. LEVANDER3 1Division of Cancer Epidemiology and Genetics, National Cancer Institute, National Institutes of Health, Executive Plaza North, Rm 430, 6130 Executive Blvd, Rockville, MD 20892, 2Biology and Biotechnology Research Program, Lawrence Livermore National Laboratory, University of California, Livermore, CA 94550, 3Nutrient Requirements and Functions Laboratory, BHNRC, ARS, United States Department of Agriculture, Center Road, Bldg 307, Rm 201, Beltsville, MD 20705-2350 and 4Early Detection Branch, DCPC, National Cancer Institute, National Institutes of Health, Executive Plaza North, 6130 Executive Blvd, Rockville, MD 20892, USA (Accepted 1 October 1997) AbstractÐMeats cooked at high temperatures sometimes contain heterocyclic amines (HCAs) that are known mutagens and animal carcinogens, but their carcinogenic potential in humans has not been established. To investigate the association between HCAs and cancer, sources of exposure to these com- pounds need to be determined. Beef is the most frequently consumed meat in the United States and for this study we determined HCA values in beef samples cooked in ways to represent US cooking prac- tices, the results of which can be used in epidemiological studies to estimate HCA exposure from diet- ary questionnaires. We measured ®ve HCAs [2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino- 3,4-dimethylimidazo[4,5-f]quinoline (MeIQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2- amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (DiMeIQx) and 2-amino-1-methyl-6-phenylimidazo- [4,5-b]pyridine (PhIP)] in dierent types of cooked beef using solid-phase extraction and HPLC.
    [Show full text]
  • Dissecting the Mechanisms and Molecules Underlying the Potential
    Cascella et al. Infectious Agents and Cancer (2018) 13:3 DOI 10.1186/s13027-018-0174-9 REVIEW Open Access Dissecting the mechanisms and molecules underlying the potential carcinogenicity of red and processed meat in colorectal cancer (CRC): an overview on the current state of knowledge Marco Cascella1†, Sabrina Bimonte1*† , Antonio Barbieri2†, Vitale Del Vecchio2†, Domenico Caliendo1, Vincenzo Schiavone3, Roberta Fusco4, Vincenza Granata4, Claudio Arra2† and Arturo Cuomo1† Abstract Meat is a crucial nutrient for human health since it represents a giant supply of proteins, minerals, and vitamins. On the opposite hand, the intake of red and processed meat is taken into account dangerous due to its potential of carcinogenesis and cancer risk improvement, particularly for colorectal cancer (CRC), although it has been reported that also the contaminations of beef infected by oncogenic bovine viruses could increase colorectal cancer’s risk. Regarding the mechanisms underlying the potential carcinogenicity of red and processed meat, different hypotheses have been proposed. A suggested mechanism describes the potential role of the heterocyclic amines (HACs) and polycyclic aromatic hydrocarbons (PHAs) in carcinogenesis induced by DNA mutation. Another hypothesis states that heme, through the lipid peroxidation process and therefore the formation of N-nitroso compounds (NOCs), produces cytotoxic and genotoxic aldehydes, resulting in carcinogenesis. Furthermore, a recent proposed hypothesis, is based on the combined actions between the N-Glycolylneuraminic acid (Neu5Gc) and genotoxic compounds. The purpose of this narrative review is to shed a light on the mechanisms underlying the potential carcinogenicity of red and processed meat, by summarizing the data reported in literature on this topic.
    [Show full text]
  • Relationship Between Content and Activity of Cytochrome P450 and Induction of Heterocyclic Amine DNA Adducts in Human Liver Samples in Vivo and in Vitro
    Cancer Epidemiology, Biomarkers & Prevention 1071 Short Communication Relationship between Content and Activity of Cytochrome P450 and Induction of Heterocyclic Amine DNA Adducts in Human Liver Samples In vivo and In vitro Pawel Baranczewski and Lennart Mo¨ller Laboratory for Analytical Toxicology, Department of Biosciences, Karolinska Institutet, Novum, Huddinge, Stockholm, Sweden Abstract This study was designed to estimate a correlation be- withPhIP and AAC correlated with the activities of tween metabolic activation phenotypes and formation three isozymes of cytochrome P450: CYP1A1, CYP1A2, of DNA adducts by heterocyclic amines (HCA) in 15 and CYP3A4. Therefore, three chemical inhibitors were liver samples from healthy donors. The correlation used in the experiments: ellipticine against CYP1A1, between the amount of endogenous DNA adducts and furafylline against CYP1A2, and troleandomycin the content of cytochrome P450 in human liver samples against CYP3A4. The highest inhibition levels in the in vivo was statistically significant at r2 = 0.71 and formation of 3V,5V-pdGp-C8-PhIP and 3V,5V-pdGp-C8- P < 0.005. Furthermore, the isolated human liver mic- AAC adducts were estimated to occur in the presence rosomes were treated in vitro with two HCAs, 2-amino- of furafylline at 56% and 69%, respectively. Ellipticine 1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and was involved in the inhibition of 40% of 3V,5V-pdG- 2-amino-9H-pyrido[2,3-b]indole (AAC), which have C8-PhIP adducts and in only 18% of the inhibition of been recognized to induce two DNA adducts: 3V,5V-di- 3V,5V-pdGp-C8-AAC adducts. Troleandomycin did not phosphate-N-(2V-deoxyguanosin-8-yl)-PhIP (3V,5V-pdGp- significantly inhibit the formation of 3V,5V-pdGp-C8- C8-PhIP) and 3V,5V-diphosphate-N-(2V-deoxyguanosin PhIP adducts under these conditions, but it inhibi- -8-yl)-AAC(3V,5V-pdGp-C8-AAC).
    [Show full text]
  • Determination and Characterization of Heterocyclic Amines and Polycyclic Aromatic Hydrocarbons in Food Products
    Kurdistan Regional Government-Iraq Ministry of Higher Education & Scientific Research Salahaddin University-Erbil College of Science Department of Chemistry Review: determination and characterization of Heterocyclic Amines and Polycyclic Aromatic Hydrocarbons in food Products A Review Article in Analytical Chemistry In Partial Fulfillment of the Requirements for the Degree of Ph. D Prepared by: Yousif Taha Maaroof, [email protected] Supervised by: Asst. Prof. Dr. Media Noori Abdullah, [email protected] (2020 – 2021) Review: determination and characterization of Heterocyclic Amines and Polycyclic Aromatic Hydrocarbons in food Products Abstract This review article was studies to produce, effects, and analyzing of heterocyclic amines, and polycyclic aromatic hydrocarbons in cooked food. Heterocyclic amine compounds are produce in the resulting high temperatures of cooking of amino acids reacts with creatine. As well as, polycyclic aromatic hydrocarbons are produce in cooking of meat, when fat pyrolysis and form intermediate products when, cooking at high temperatures. As a results of cooking methods Heterocyclic amines and polycyclic aromatic hydrocarbons will be form especially foods can be contaminated at high temperatures cooking methods such as, at grilling, smoking of chicken, barbecuing meat, and smoking steak. When fish and/or meat is smoked, or grilled, or barbecued in open fire at high temperatures higher polycyclic aromatic hydrocarbons production. Heterocyclic amines are generally carcinogenic compounds and causes to colon cancer, breast cancer, with prostate cancer, but polycyclic aromatic hydrocarbons do not effect to cancer once, although different polycyclic aromatic hydrocarbons as a mixture linked together effects to cancer. The main four polycyclic aromatic hydrocarbons which more effects on the carcinogenic in human body, due tobenzo[a]pyrene, and bennz[a]anthracene, and benzo[b]fluoranthene, and chrysene.
    [Show full text]