Papageorgiou, M., Lambropoulou, D., Morrison, C., Kłodzińska, E., Namieśnik, J

Papageorgiou, M., Lambropoulou, D., Morrison, C., Kłodzińska, E., Namieśnik, J. and Płotka-Wasylka, J. (2018) Literature update of analytical methods for biogenic amines determination in food and beverages. Trends in Analytical Chemistry, 98, pp. 128-142. (doi:10.1016/j.trac.2017.11.001) This is the author’s final accepted version. There may be differences between this version and the published version. You are advised to consult the publisher’s version if you wish to cite from it. http://eprints.gla.ac.uk/150964/ Deposited on: 02 November 2017 Enlighten – Research publications by members of the University of Glasgow http://eprints.gla.ac.uk 1 Literature update of analytical methods for biogenic amines determination in food and 2 beverages 3 Myrsini Papageorgiou1, Dimitra Lambropoulou1, Calum Morrison2, Ewa Kłodzińska3, Jacek 4 Namieśnik3, Justyna Płotka-Wasylka3* 5 6 1Department of Chemistry, Environmental Pollution Control Laboratory, Aristotle University of Thessaloniki, 54 7 124 Thessaloniki, Greece 8 2 Forensic Medicine and Science, School of Medicine , Dentistry and Nursing, College of Medical, Veterinary 9 and Life Sciences, University of Glasgow, Glasgow G12 8QQ, United Kingdom 10 3Instiute of Sport - National Research Institute, Department of Anti-Doping Research, Trylogii 2/16 Street, 01- 11 982 Warsaw, Poland 12 4 Department of Analytical Chemistry, Faculty of Chemistry, Gdańsk University of Technology, 11/12 13 Narutowicza Street, 80-233 Gdańsk, Poland 14 15 *coresponding author: [email protected]; [email protected] 16 Graphical Abstract 17 meat fish diary products & cheese Biogenic Amines (BA) alcohol beverages fruits & vegetables soybean products chocolate 18 19 1 1 Abstract 2 Biogenic amines (BAs) have been reported in a variety of foods, such as fish, meat, cheese, 3 and wines. The formation of BAs in food by the microbial decarboxylation of amino acids can 4 result in human allergic reactions, characterized by difficulty in breathing, rash, vomiting, and 5 hypertension. Control measures to prevent biogenic amine formation in foods and/or reduce 6 their levels should be considered. Therefore, monitoring of BAs in food samples with the 7 application of analytical techniques is of high importance. 8 This review is based on literature data from 2010 until today and refers to food samples and 9 alcoholic beverages. The rationale of this study is to provide data for the occurrence of BAs 10 in food and beverages samples and a comparison of the analytical techniques and challenges 11 in liquid and solid matrices. Importantly, BAs can be used as future markers for quality and 12 freshness of the food products and alcoholic beverages. 13 14 Keywords 15 Biogenic amines, food samples, chromatographic techniques, capillary electrophoresis, green 16 assessment 17 1. Introduction 18 Nowadays, food products are manufactured and distributed worldwide, while deficiencies in 19 regulation increases the concern for consumer‘s health. Heavy metals, pesticides, 20 pharmaceuticals, personal care products and biogenic amines have been detected in different 21 food matrices worldwide. A so called -chemical contamination- include multi-residues, may 22 enter the food chain from different routes. Some sources linked with chemical contamination 23 potentially include the application of pesticides in the field, veterinary medicines in animals, 24 natural toxins and residues formed during the food processing or intentional contamination, 25 such as food adulteration or contamination from sources which have not yet been identified. 26 Amino acids are the main compounds which offer nutrition value, aroma and flavor in 27 products such as cheese, wine, honey and other fermented foodstuffs after microbial or 28 enzymatic conversion [1]. Therefore, the bacterial decarboxylation of amino acids or 29 transamination of aldehydes and ketones leads to formation of active biogenic amines (BAs) 30 [2, 3]. BAs are nitrogenous organic bases of low molecular weight, polar or semi-polar 31 compounds with aliphatic (putrescine, cadaverine, spermine and spermidine), aromatic 32 (tyramine, phenylethylamine) or heterocyclic (histamine, pyrrolidine) structure. 33 2 1 The demand for safer foods has promoted more research into biogenic amines over the past 2 few years, and thus many countries are involved in the analysis of food samples in terms of 3 biogenic amines occurrence (Figure 1). However, there are still some questions that remain 4 unanswered. Despite the fact that biogenic amines are present in foods and beverages and can 5 cause toxic effect to the body, a shared regulation limiting the amounts of biogenic amines in 6 food and beverages is still lacking. Knowledge on their presence in wine is also important for 7 the food trade sector. 8 Referring to BAs, their occurrence has been detected in a broad range of protein-rich food 9 matrices (from plant or animals origin) that are regularly consumed by humans and placed 10 within a daily dietary program, such as meat [4-7], fish [4, 5, 8-14], dairy products [15] and 11 alcoholic beverages. This could place them as markers for food and beverages quality and 12 freshness being connected to the degree of food storage, processing or degradation [16]. 13 Therefore, any food stuff produced by fermentation or exposed to microbial contamination 14 during processing or storage may contain BAs [17]. 15 With respect to health risks, little legislation exists; in low concentration BAs are essential for 16 many physiological functions in humans, acting as hormones or neurotransmitters. The key 17 roles of BAs are important for growth, renewal, and metabolism in organs, for high metabolic 18 activity of the normal functioning and immunological system of the gut and for temperature 19 regulation [18-20]. While in high concentrations, effects such as headache, nausea, hypo- or 20 hypertension, migraine, skin allergy and digestive problems of food poisoning have been 21 observed by biogenic amines [21, 22]. Also, Biogenic Amines (BAs) are precursors of 22 nitrosamines, which have been linked to carcinogenic and mutagenic activity. Generally, BAs 23 are not destroyed during cooking, treatment with high temperature, storage and are stable and 24 difficult to degrade [23]. 25 The determination of biogenic amines is laborious and challenging due in part to the 26 physicochemical properties of these compounds. Numerous analytical methods have been 27 developed while few of them can overcome the step of the derivatization process easily. A 28 pre-concentration step is generally needed, when the analysts deal with complex matrices. 29 During the last decade, new articles have developed extractions which can be more 30 environmental friendly, with the use of less toxic, organic solvents combined with sensitive 31 and selective analytical instrumentation using mass spectrometer and tandem mass 32 spectrometer detectors [5, 24, 25]. 33 The aim of this review is to summarize the concentration of biogenic amines in different food 34 and beverage products from 2010 until today, to highlight which matrices have not been 3 1 analyzed and also, which matrices are the most popular and should continue to be monitored 2 for their toxicity. Regarding the physicochemical characteristics of BAs, an overview of the 3 analytical methodologies, cleanup and pre-concentration techniques, a comparison between 4 the derivatization agents and environmental assessment of the analytical methodologies have 5 been made, so we can underline the development of more green, environmental friendly 6 extraction procedures. Finally, the regulation policy and the toxicity of BA‘s have been 7 discussed. The study concludes with a focus on the main issues that should be further 8 investigated. 9 10 11 Figure 1. Percentage breakdown of biogenic amine researches related to food products 12 published since 2010 categorized with the geographical region of the analyzed samples 13 14 2. Function and occurrence of biogenic amines 15 Generally, BAs are sources of nitrogen and precursors for the synthesis of many specific 16 compounds in organisms such as alkaloids, hormones, nucleic acids, and proteins. Moreover, 17 they are also responsible for several processes in the organism such as the regulation of body 18 temperature, intake of nutrition, increase/decrease of blood pressure [26]. In plants, 19 putrescine, spermidine and spermine are implicated in a numerous of physiological processes, 20 such as cell division, fruit development, flowering, response to stress and senescence. 21 Generally, polyamines are important for processes of every organ in the body including 22 growth, renovation, metabolism and are essential for maintaining the high metabolic activity 23 of the normal functioning and immunological system of gut [26]. 24 It has been shown that BAs are potential precursors for the formation of carcinogenic N- 25 nitroso compounds. The reaction of primary amines and nitrosating-agents produces short- 26 lived alkylating species, which can react with other components present in the food matrix to 4 1 generate products for example alcohols, devoid of toxic activity in the relevant contents [26]. 2 The secondary amines such as agmatine, spermine, spermidine and others can react with 3 nitrile and, in sum, generate the nitrosamines, while tertiary amines produce a range of labile 4 N-nitroso products [27]. In foods contain high level of fat (e.g. bacon), in the presence of 5 water and at high temperature, the carcinogen N-nitrosopyrrolidine can

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