A review of pretreatment and analytical methods of biogenic amines in food and biological samples since 2010

https://doi.org/10.1016/j.chroma.2019.07.015Get rights and content

Highlights

  • Comprehensive information of classification and physiological activity of biogenic amines.

  • Updated information on sample pretreatment and analytical methods of biogenic amines.

  • Separation conditions, analytical conditions and validation information are compared.

  • Abundant figures and tables are offered.

Abstract

Biogenic amines (BAs), mainly produced by amino acid decarboxylation, are widespread in foods and human organisms. Appropriate intake of BAs is beneficial to the human body, while excessive consumption may cause discomfort. Meanwhile, BAs are a kind of chemical marker for evaluating meat freshness. For these reasons, simple, rapid and efficient methods have been developed for the determination of BAs in food and biological products. This review introduces the provenance, classification and physiological activity of eight essential BAs and summarizes the dominant pretreatment and analysis methods since 2010. Pretreatment technologies mainly include the “dilute and shoot” method, ultrasonic assisted extraction, solid-phase extraction, matrix solid-phase dispersion, dispersive liquid-liquid microextraction, etc. Determination methods include liquid chromatography coupled to ultraviolet or fluorescence detectors, liquid chromatography tandem mass spectrometry, capillary electrophoresis, biosensors and so on.

Introduction

Biogenic amines (BAs), a kind of low molecular weight nitrogenous compounds, are mainly formed by decarboxylation of amino acids [[1], [2], [3]]. BAs are common active components that are precursors for the synthesis of hormones [4], alkaloids [5], nucleotides [6], proteins [7], and aromatic compounds [8,9], and they play important physiological roles in organisms. There are eight BAs commonly existing in plants [10,11], animals [11,12] and foods [[1], [2], [3],8,13,14]: putrescine (PUT), cadaverine (CAD), spermine (SPM), spermidine (SPD), tyramine (TYR), phenylethylamine (PEA), histamine (HIS), and tryptamine (TRP). These BAs are divided into aliphatic amines, aromatic amines and heterocyclic amines according to their structures [13]. The names, structures and classifications are listed in Table 1.

Each BA exerts its own irreplaceable effects in organisms. HIS can affect intestinal physiological functions [15,16] and the quantity of white blood cells [17,18]. SPM, SPD, PUT and CAD can regulate the synthesis of DNA, RNA and protein and maintain the stability of biofilms [[19], [20], [21]]. SPM also has a regulatory effect on the small intestine [22,23]. TRP, PEA, and TYR can regulate blood pressure [24], and PEA can also regulate the level of norepinephrine [25]. Meanwhile, TYR has significant antioxidant effects [26]. TYR can increase heart rate and blood sugar concentration. In addition, dopamine, adrenaline and serotonin act as neurotransmitters [27,28], which also have potential effects on behavior.

The adequate intake of BAs can promote growth, enhancing metabolism and eliminating free radicals, while excessive consumption may result in toxicity and metabolic disturbance and is harmful to the nervous and cardiovascular systems [29,30]. High levels of HIS can lead to headache, digestive disorder, dysarteriotony or even neurotoxicity [[31], [32], [33]]. TYR exhibits secondary toxicity that can cause hypertension [34]. CAD and PUT are milder, but they can inhibit the activity of HIS and TYR related to metabolic enzymes [35,36]. Moreover, CAD, PUT, SPM and SPD reactions with nitrite may produce carcinogenic nitrosamine [37,38].

BAs are widely found in foods in daily life, such as condiments, fermented sausages, rice wine, wine, beer, cheese and other fermented food, meat and aquatic products. Unreasonable environmental hygiene, food processing technology and food storage means all result in the production of a large number of BAs. To avoid excessive intake of BAs, many countries and regions have set limits on the amounts of BAs in aquatic products, food and wine (Table 2) [[39], [40], [41], [42]].

It was found that the formation of BAs in fish and meat is associated with the growth of spoilage microorganisms, which have low volatility and thermal stability, and is often used as a chemical index to evaluate the freshness of fish and meat [43]. Fish tissue is rich in free histidine, which is easily affected by histidine decarboxylase produced by corresponding microorganisms and forms a large amount of HIS. Therefore, HIS is often used as an index to evaluate the freshness of fish. CAD and PUT are the main BAs that affect the putrefaction process of pork and are often used to evaluate the freshness of pork. TYR is related to the freshness of beef and chicken. Thus, the biogenic amine index (BAI) has been proposed to evaluate the freshness of fish and meat (BAI=HIS + CAD + PUT + TYR). BAI < 5 mg/kg verifies good quality fresh meat; between 5 and 20 mg/kg indicates acceptable meat, but with initial spoilage signs; between 20 and 50 mg/kg warns of low meat quality; finally, > 50 mg/kg represents spoiled meat [42]. The content of BAs in putrefied meat and aquatic products will be greatly increasing. People who consume these foods may develop bromatoxism. In light of the importance of BAs and their potential harm to human health, a large number of methods have been successively developed to purify and quantify BAs in food samples. The detection of amine-producing bacteria by traditional microbial method is complicated and unreliable because of the long period and low sensitivity. Moreover, microbial metabolism is complex, and it is easy to produce acidic or alkaline substances in cultivation process, resulting in false negative or false positive results. Compared with microbial detection methods, BA detection methods are more accurate, rapid and easy to operate [44].

Conventional pretreatment methods, such as “dilute and shoot”, protein precipitation, solid phase extraction (SPE) and ultrasonic assisted extraction (UAE), have been frequently used to extract and purify BAs from sample matrices. Modern preferred methods, such as dispersive liquid-liquid microextraction (DLLME) and matrix solid-phase dispersion (MSPD), consume minimal reagents and are easy to operate. Most BAs exhibit neither UV absorption nor fluorescence emission, so derivation is necessary for liquid chromatography (LC) and capillary electrophoresis (CE) coupled with ultraviolet (UV) or fluorescence detectors (FLD). Among these analysis methods, liquid chromatography tandem mass spectrometry (LC–MS/MS) is accurate and reliable, offers rapid separation and high sensitivity, and represents a broader prospect for development in the future.

Several researchers have previously published reviews of determination methods for BAs. Önal et al. [45] published a review about LC methods for the determination of BAs in foods. However, that paper only included LC coupled with UV, FLD and MS methods, while in this review, the analysis methods are more comprehensive and extensive. Loizzo et al. [46] summarized a few methods for cheese that were unrepresentative, but the samples in this paper included diverse food and biological products. The review written by Erim et al. [47] provided only an overview of recent analytical approaches for BAs in food samples between 2011 and 2012. This review covered comprehensive and novel studies from 2010 to the present, so that researchers could keep up with the latest developments.

This paper reviewed the pretreatment and analytical approaches for BAs in food and biological samples since 2010. A variety of common extraction methods and determination methods have been discussed in detail. The aim of this review was to summarize the pretreatment and analysis methods for BAs in food, environmental and biological samples since 2010 to provide a reference for further studies.

Section snippets

Sample pretreatment methods

Proper pretreatment can reduce matrix interference, increasing the signal strength of analytes and laying a foundation for subsequent instrumental analysis. Liquid substrates without protein can be directly diluted to preserve the analytes. For protein-rich samples, such as milk, protein precipitation is necessary to remove macromolecular substances. Samples with complex substrates require multiple steps of extraction and purification to ensure sample purity. For example, cheeses were extracted

Analytical methods

Analytical methods suitable for the determination of BAs in food and biological samples must have high separation efficiency, selectivity and sensitivity to avoid analyte interference with the complex matrix and structural analogues. Basic methods include LC-UV, LC-FLD, LC–MS/MS, CE, biosensors, ELISA, GC–MS, TLC, etc. HPLC is a compatible separation technology that can be combined with different detectors for separation and detection. Among these detectors, LC–MS/MS is a universal instrument,

Conclusions

This paper reviewed the pretreatment and analytical methods for BAs in food and biological samples since 2010. Appropriate pretreatment and detection methods can be selected according to the complexity of the matrix and the aim of detection. Simple pretreatment methods, such as “dilute and shoot” and protein precipitation, can prevent analytes from being lost, but the extraction and purification are not thorough enough, which may bring about matrix interference, and so these methods are only

Conflict of interest

The authors have declared no conflict of interest.

Acknowledgement

This work was supported by CAMS Innovation Fund for Medical Sciences (CIFMS) (NO. 2016-I2M-1-001), Key Program of the Natural Science Foundation of Liaoning Province of China (NO. 20170541027), Liaoning planning Program of philosophy and social science (NO. L17BGL034), Research Program on the Reform of Undergraduate Teaching in General Higher Schools in Liaoning (NO. 2016-346), and China Medical University philosophy and social science promotion plan (2018).

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