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CHAPTER 6 Detection of Biogenic Amines: Quality and Toxicity Indicators in Food of Animal Origin

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CHAPTER 6 Detection of Biogenic Amines: Quality and Toxicity Indicators in Food of Animal Origin CHAPTER 6 Detection of Biogenic Amines: Quality and Toxicity Indicators in Food of Animal Origin César A. Lázaro de la Torre*,**, Carlos A. Conte-Junior**,† *National University of San Marcos, San Borja, Lima, Peru; **Federal Fluminense University, Niterói, Rio de Janeiro, Brazil; †Food Science Program, Chemistry Institute, Federal University of Rio de Janeiro, Rio de Janeiro, Brazil 1 Biogenic Amines 1.1 Definition Biogenic amines (BAs) are low molecular weight substances, primarily produced during the normal metabolism of animals, plants, and microorganisms; their biological participation is related to psychoactive, neuroactive, or vasoactive process (Gloria, 2005; Ten Brink et al., 1990). Their presence in foods is directly related to microorganisms (spoilage bacterial) with decarboxylase activity on free amino acids (FAA). However, other factors, such as amino acid composition (kind of food), temperature, and time of storage, technological processes (maturation, packing, cooking, etc.) are important in BAs presentation (Halász et al., 1994). Most of the BAs have been named according to their amino acids precursors (histamine originates from histidine) and the most interesting classification is related to the number of amine groups: mono-, di-, and polyamines for tyramine, cadaverine, and spermidine respectively (Gloria, 2005). A graphic summary of BAs formation is presented in Fig. 6.1. 1.2 Classification Previously, we mentioned that BAs are classified based on the number of amine groups. However, chemical structure, biosynthesis, or physiological functions are used to divide them. Ruiz-Capillas and Jiménez-Colmenero (2004), Silla Santos (1996), and Shalaby (1996) presented a classification according to the number of amine groups: monoamines (tyramine, phenylethylamine), diamines (histamine, serotonin, tryptamine, putrescine, cadaverine), or polyamines (spermine, spermidine, agmatine). According to the chemical structure, amines can be aliphatic, where the amino groups are not linked together to form a ring Food Control and Biosecurity http://dx.doi.org/10.1016/B978-0-12-811445-2.00006-4 225 Copyright © 2018 Elsevier Inc. All rights reserved. 226 Chapter 6 Figure 6.1: Process of Biogenic Amine Formation. Ar, Arginine; Glu, glutamine; His, histidine; Lys, lysine; Orn, ornithine; Try, tryptophane; Tyr, tyrosine. Adapted from: Ruiz-Capillas, C., Jiménez-Colmenero, F., 2004. Biogenic amines in meat and meat products. Crit. Rev. Food Sci. Nutr. 44, 489–499; Benkerroum, N., 2016. Biogenic amines in dairy products: origin, incidence, and control means. Comp. Rev. Food Sci. Food Saf. 15, 801–826. (e.g., cadaverine, putrescine, spermine, spermidine); aromatic, where amino group is linked directly to an aromatic ring (e.g., tyramine, phenylethylamine), or heterocyclic, where amine containing one or more closed rings of carbon and nitrogen (e.g., histamine, tryptamine, serotonin). Another classification, according to biosynthetic pathway, defines amines, such as natural, which are formed during normal organic metabolic process; and biogenic, formed by bacterial decarboxylation of FAA. Histamine can be either natural (stored in basophils) or biogenic. 1.3 Synthesis Removing the α-carboxyl group from a specific amino acid leads to the formation of corresponding BA (Bodmer et al., 1999). Decarboxylases are named according to their effect on specific amino acid (e.g., histidine decarboxylase, tyrosine decarboxylase, and lysine decarboxylase) and their production is related to genes present in different kind of Detection of Biogenic Amines 227 bacteria (Benkerroum, 2016). Requisites to amine formation in foods included the presence of FAA, decarboxylase-positive microorganisms, and favorable conditions in processing and storage (temperature, time, and others) for microbial growth and decarboxylase activity. Bacterial and thermal activity contributed to proteins degradation and presence of FAA in foods (Gloria, 2005). 1.4 Relationship with Foods The presence of BAs in foods is important for their potential relationship with toxicity in humans, but also for the application, such as bacterial quality indicators. Analysis of BAs is used in the monitoring of raw, intermediates, and final food products, fermentation processes, change during storage, and application of new technologies of conservation (Önal, 2007). Detection and quantification of BAs in food products has been related with the following aims: (1) development of new methods or improving current methods for BAs identification; (2) differences of BAs contents in traditional and/or nontraditional food products; (3) variations of BAs levels after modification in obtaining, processing, storage, and packaging in foods; and (4) establish a connection between levels of BAs and microorganisms in different foods matrices (Bedia Erim, 2013). 2 Biogenic Amines: Toxicological Aspect The relationship between the level of BAs and food poisoning has been widely studied. People normally eat foods with some levels of BAs; these levels are quickly detoxified in the intestinal mucosa by enzymatic reactions (oxidases). However, some particular states, such as genetic alteration, allergic, alcohol, and/or ingestion of monoamino oxidase antidepressant could become dangerous the levels of BAs (Alvarez and Moreno-Arribas, 2014; Jairath et al., 2015). The consumption of foods with high concentrations of BAs is associated with migraine, headaches, bowel disorders, and allergy responses. This is particularly important in foods with high levels of histamine and tyramine, where allergy episodes are known as “histamine poisoning” and “cheese reaction,” respectively. Histamine intoxication is the most frequent food-borne intoxication caused by amines. Although this intoxication is referred to as “scombroid poisoning” due to its association with scombroid fish consumption, it is known that nonscombroid fish, cheese, and other foods have also implicated in histamine toxicity (Rodriguez et al., 2014; Souza et al., 2015). The histamine intoxication begins several minutes to few hours after the consumption of foods with high levels of histamine. Early symptoms include flushing of the face and neck, feeling of warmth and general discomfort. In some cases, patients report headache (Bodmer et al., 1999; EFSA, 2011; Shalaby, 1996; Silla Santos, 1996). As mentioned previously, high concentrations of histamine in foods is a risk factor for human intoxication. However, moderate levels may result in food intolerance. This is important in people with deficiency in diamine oxidase activity, also known as histaminase, who reported 228 Chapter 6 numerous undesirable reactions after intake of foods containing histamine. Besides spoiled, fermented foods are most susceptible to contain elevated levels of BAs. In addition, these concentrations may vary according to the food matrix and even within one type of food (Bodmer et al., 1999). Recently, polyamines like putrescine, spermidine, and spermine, were indicated, such as precursor of carcinogenic N-nitrosamines and this is an additional toxicological risk associated to BAs (Jairath et al., 2015). Due to these serious problems with BAs, Leuschner et al. (2013) analyzed the information on cases of food poisoning related to BAs reported in the Rapid Alert System for Food and Feed (RASFF), a European network involved in food safety threats, and concluded that the presence of histamine in foods must be one of the priorities in public health due to the relationship of human cases of histamine poisoning and the consumption of foodstuffs of animal origin, and fish products and cheese. Around the world, countries and organizations adopted similar limits for histamine in fish species (Scombridae, Clupeidae, Engraulidae, Coryphenidae, Pomatomidae, and Scombreresosidae) and fishery products (species previously related but submitted to enzymatic fermentation). European Union, Codex Alimentarius, Australia, and New Zealand determined limited values of histamine above 200 mg/kg in fish. However, the FDA considered 50 mg/kg such a limit of histamine. However, it is important to remark that these limits could be higher for people medicated with mono amino oxidase inhibitor drugs (EFSA, 2011; Mohedano et al., 2015; Visciano et al., 2012). In a review performed by Rodriguez et al. (2014), the consumption of other BAs, such as tyramine, putrescine, and cadaverine could be a potential risk in human health. Tyramine is related to the vasoconstrictor effect, putrescine and cadaverine cause hypotension and bradycardia, besides potentiating the toxicity of other amines. Finally, consumption of high levels of putrescine, spermidine, and spermine can accelerate the development of tumors, because they are found in tissues with high growing rate. 3 Biogenic Amines: Food Quality Aspect Another use of BAs is indirect quality indicators of microbial activity in raw and cooked meat products. The normal trend is that tyramine, putrescine, and cadaverine increase and spermidine and spermine decrease or remain constant during the processing and storage of meat and meat products (Bardócz, 1995; Halász et al., 1994). The slight increase in putrescine and cadaverine levels prior to spoilage and positive correlation with the bacterial growth in fresh meat suggested their use as indicators of bacterial quality (Ruiz-Capillas and Jiménez-Colmenero, 2004). These reports suggest the use of BAs as an index of hygienic conditions related to bacterial increasing during the decomposition process, especially in fresh meat
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