Determination Of Biogenic Amines Research Articles

Development of a new high performance liquid chromatography-fluorescence detection (HPLC-FL) method for the determination of biogenic amines in frozen fish sold in markets

<p class="MsoNormal" style="text-align:justify;line-height:200%"><span lang="EN-GB" style="font-size:12.0pt;line-height:200%;font-family:"Times New Roman","serif"; mso-fareast-font-family:"Times New Roman";mso-ansi-language:EN-GB;mso-fareast-language: ZH-CN">It is now possible to measure the biogenic amines histamine, tryptamine, putrescine, cadaverine, spermidine, spermine, and tyramine in an easy, accurate, and selective manner. Dansyl chloride was used to purify the analytes, and high-performance liquid chromatography with detection of fluorescence was utilized for separating them. This is a useful method for identifying and measuring biogenic amines in fish samples in a selective manner. The C18 (250 mm × 4.6 mm × 5 μm) column was used for the separation by chromatography. A mobile phase comprising acetonitrile and phosphate buffer (pH=4.0) (60:40, v/v) was used at an average flow rate of 0.9 mL/min. The technique relied on utilizing fluorescence detection to determine the derivative </span><span style="font-size:12.0pt;line-height:200%;font-family: "Times New Roman","serif"">(λ<sub>ex</sub>=230 nm, λ<sub>em</sub>= 350 nm) </span><span lang="EN-GB" style="font-size:12.0pt;line-height:200%;font-family:"Times New Roman","serif"; mso-fareast-font-family:"Times New Roman";mso-ansi-language:EN-GB;mso-fareast-language: ZH-CN">The suggested method's linearity was examined between 0.01 and 50 μg/mL </span><span style="font-size:12.0pt;line-height:200%;font-family:"Times New Roman","serif"">(r<sup>2</sup>=0.9996). </span><span lang="EN-GB" style="font-size:12.0pt;line-height:200%;font-family: "Times New Roman","serif";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-GB;mso-fareast-language:ZH-CN">In compliance with ICH criteria, the method was verified with respect to accuracy, precision, repeatability, specifity, robustness, and detection and quantification limitations. The suggested technique has been effective in tracking the production of biogenic amines in specimens of fish that can be purchased frozen in marketplaces. It was discovered that the recommended approach worked well for routinely analyzing fish sample biogenic amine analyses.<o:p></o:p></span></p>

Advances in the application of ion chromatography-mass spectrometry in the fields of life and health

Ion chromatography is a technique commonly used to separate strongly polar and ionizable substances; it can be used to separate, identify, and quantify ionizable compounds in complex samples when coupled with mass spectrometry, and is currently being used in the application of food analysis, drug analysis, metabolomics and clinical poisoning analysis. Herein, we review the development of ion chromatography-mass spectrometry (IC-MS), its progress over the past 20 years, and future trends in the abovementioned areas. The IC-MS research progress and applications for the determination of inorganic anions, organic acids, polar pesticides, biogenic amines, and sugars in the food field are discussed. Drug analysis applications are discussed mainly in relation to the analysis of drug impurities, identifying drug degradation products, and determination of plasma concentration, while the separation and analysis of strongly polar metabolites, such as organic acids, sugar phosphates, and nucleotides in biological matrices are discussed in relation to metabolomics. Advances in the analysis of strongly polar or ionizable toxic compounds, such as alkyl methylphosphonic acid, methylphosphonic acid, glyphosate, 3-nitropropionic acid, and indandione rodenticides, are mainly discussed in clinical poisoning analysis field. This paper is expected to become a useful reference for the further expansion and application of IC-MS in the life and health fields.

One-pot derivatization/magnetic solid-phase extraction combined with high-performance liquid chromatography-fluorescence detection for rapid analysis of biogenic amines in alcoholic beverages

The determination of biogenic amines (BAs) in alcoholic beverages is crucial for assessing their health impact, ensuring beverage quality, and guaranteeing safety. Herein, a rapid one-pot derivatization/magnetic solid-phase extraction (OPD/MSPE) method was proposed using 6-aminoquinolinyl-N-hydroxysuccinimide carbamate as the derivatization reagent and magnetic hydroxyl-functionalized multi-walled carbon nanotubes as the extraction material. Integration of derivatization and extraction steps simplifies the sample preparation process, taking only three minutes and eliminating the need for centrifugation by utilizing magnetic sorbent. The resulting desorption solution was directly analyzed by high-performance liquid chromatography-fluorescence detection (HPLC-FLD) without any evaporation or reconstitution steps. The integrated OPD/MSPE-HPLC-FLD method demonstrates excellent linearity (R2 > 0.992), accuracy (relative recoveries: 85.1–109.2%), precision (RSDs≤9.7%) and detection limits (limits of detection: 0.3–2 ng/mL). It has been successfully applied to determine free BAs in various alcoholic beverages, including red wine, Baijiu, Huangjiu, and beer. This method enables rapid, sensitive and precise analysis of BAs in alcoholic beverages.

Development and validation of a rapid and simple HILIC-MS/MS method for the determination of biogenic amines in tuna fish

The production of biogenic amines (BAs), which are markers of both quality and safety in fish and fishery products, is influenced by the harvesting technique, handling, and other operations including those carried out on board the vessel. Scombroid dark-meat fish (e.g. tuna) are the fish species most frequently linked to histamine poisoning. The most commonly found BAs in fish are histamine, tyramine, putrescine, and cadaverine, which are produced when microbes decarboxylate the corresponding free amino acids. In this study, a rapid and cost-effective HILIC-MS/MS method was developed and validated for the determination of putrescine, cadaverine, histamine and tyramine in tuna samples. A simple sample preparation procedure was followed using the solvent mixture MeOH/H2O (50/50, v/v), 0.1 % acetic acid for protein precipitation and analyte extraction. Intra- and inter-day accuracy, expressed as %Recovery (%R), ranged from 88.0 % (Cad) to 102.7 % (Tyr) and from 85.0 % (Cad) to 99.8 % (Tyr), respectively. Intra- and inter-day precision, expressed as %Relative Standard Deviation (%RSD), ranged from 0.4 % (Tyr, Put) to 3.3 % (His) and from 0.7 % (Tyr) to 5.0 % (Cad), respectively. Limits of detection (LOD) and quantification (LOQ) varied from 0.0009 to 0.0940 mg/kg and from 0.0030 mg/kg to 0.3100 mg/kg, respectively, depending on the analyte. Regarding the potential toxic effects linked to biogenic amines in foods, samples examined in this study showed no risk. The proposed method is an important analytical tool for routine analysis of BAs in fish products.

Determination of Biogenic Amines in Food by Capillary Electrophoresis

Determination of Biogenic Amines in Food by Capillary Electrophoresis

Rapid determination of biogenic amines in ossotide injections by microfluidic chip-mass spectrometry platform: Optimization of microfluidic chip derivatization using response surface methodology

The microfluidic-chip mass spectrometry (MS) platform was developed for the rapid and automatic determination of 10 biogenic amines (BAs) in ossotide injections. The microfluidic chip was primarily consisted of a square unit for derivatization and a solid phase extraction (SPE) unit. The derivatization unit could achieve automatic mixing and reaction between sample and derivatization reagents, after which the targets were purified and enriched in SPE unit, further improving the sensitivity. To select the optimal derivatization conditions, four major parameters affecting derivatization in the microfluidic chip were optimized using Box-Behnken response surface design. On-chip derivatization unit enabled the shortest derivatization time by thorough solution mixing. There is no additional pretreatment required for the entire process. The developed method achieved satisfactory limits of detection (0.045–0.855 ng/mL) and limits of quantitation (0.156–3.11 ng/mL). The recoveries of the method ranged from 75.0 % to 106 % when coupled in-line with MS. This pretreatment chip-MS platform was successfully applied to BAs detection in the commercially available ossotide injections, demonstrating the prospects of this technique as a potential method for the rapid determination. The results of BAs in ossotide injections provide a basis for the formulation of the limit standard in pharmaceutical preparations.

A Review on the Determination of Biogenic Amines in Fresh and Processed Fish Products using HPLC, LC-MS/MS and Other Chromatographic Methods.

Biogenic amines (BAs) are compounds deemed to be foodstuff contaminants and are the cause of poisoning or allergy. The main BAs found in foods include histamine, tyramine, putrescine, cadaverine, spermine and spermidine. The number of poisoning cases related to BAs in food has increased, which is reinforcing the need for BAs detection to ensure food safety. BAs are found in varying quantities in different foods such as fish, fruits, meat, cheese, vegetables, beer, and wine. Currently, different analytical techniques are used for BAs detection, as well as sample treatment methods that allow greater sensitivity, higher analyzing speed and lower detection limits. Moreover, BAs can be precursors of nitrosamines, which have been associated with mutagenic and carcinogenic activity. This review aims to provide a general approach to the different detection techniques of the BAs in foods, their concentrations and treatment methods.

Freshness evaluation of grass carp by volatile biogenic amines monitored by secondary electrospray ionization ion mobility spectrometry

In this paper, a secondary electrospray ionization ion mobility spectrometry (SESI-IMS) method using ammonium acerate was evaluated for rapid determination of the various volatile biogenic amine contents in grass carp (Ctenopharyngodon idella). The ammonium ion generated by electrospray ionization source functions as reactant ion to react with volatile biogenic amines in gas phase and separated in the drift tube. The SESI-IMS method requires minimum sample preparation and minimum interferences, and volatile biogenic amines show their unique drift times without overlapping. The content of volatile biogenic amines demonstrates good correlations with storage times at 4 ℃ and 8 ℃ cold storage. It is shown that trimethylamine and putrescine are the dominant biogenic amines during the cold storage process. Other freshness indicates including sensory evaluation, hardness, pH and total volatile basic nitrogen (TVB-N) also show good consistency with volatile biogenic amines. The developed method is a rapid, simple, and sensitive method for the determination of volatile biogenic amines in grass carp.

Determination of biogenic amines in dry fish samples (Scomber scombrus)

The research focuses on the comprehensive analysis and quantification of biogenic amines in dry fish samples, an essential aspect of food safety and quality. To achieve accurate and reliable results, a robust analytical method was adopted using high-performance liquid chromatography (HPLC) equipped with DAD UV/ Vis detector. The extraction of biogenic amines from dry fish samples was optimized to ensure maximum recovery, and suitable derivatization techniques were employed to enhance the detectability of these compounds. Nine (9) biogenic amines; Histamine (HIS), Cadaverine (CAD), Tyramine (TYM), Ethylamine (ETH), Methylamine (MET), Putrescine (PUT), Typtamine (TYP), Agmatine (AGM) and Isoamlamine (ISO) were analyzed in the fish samples. The correctness and repeatability of the method were assessed by performing replicate analyses (n = 3) for two samples of dried fish from Mile 2 and Choba sites respectively. The detection levels of biogenic amines in the dried fish samples ranged from 1.mg/kg to 1.70 mg/kg for agmatine; from 0.03 mg/kg to 0.04 mg/kg for cadaverine; from 5.52 mg/kg to 5.60 mg/kg for Ethylamine; from 0.42 to 0.48mg/kg for histamine; from 7.15 mg/kg to 7.16 mg/kg for Methylamine; from 5.13 mg/kg to 5.29 mg/kg for Isoamalamine; from 0.84 mg/kg to 0.90 mg/kg for Putrescine; from 2.70 mg/kg to 2.90 mg/kg for tryptamine and from 4.26 mg/kg to 4.44 mg/kg for tyramine across all sample locations respectively. The maximum histamine, Cadaverine and Agmatine detection levels were significantly less than other bioamines detected. Nine biogenic amines were detected where Cadaverine tends to be the lowest and high Methylamine concentration was recorded in both samples, though less than those of the regulation and recommendation set by the EU regulations and national standards for fish products.

A high-performance liquid chromatography with dSPE clean-up method for determination of biogenic amines in ripened meat products

Biogenic amines (BAs) are nitrogen compounds formed during decarboxylation of amino acids with the participation of bacteria. A method based on high-performance liquid chromatography with diode array detector (HPLC–DAD) for the determination of eight biogenic amines in ripened meat products was developed and validated. Biogenic amines were extracted with 0.1 M hydrochloric acid and pre-column derivatized with dansyl chloride at 60 °C for 15 min, extracted with toluene, and dried under a stream of nitrogen. After reconstitution in acetonitrile, the extract was subjected to clean-up by dispersive solid-phase extraction (dSPE) using Z-Sep+ sorbent. The method was validated with the BAs at three concentration levels: 50, 100 and 200 mg/kg. The limit of detection (LOD) ranged from 1.51 to 2.20 mg/kg, and limit of quantification (LOQ) was between 5.08 and 7.34 mg/kg. The obtained correlation coefficients (R2) ranged from 0.9997 to 0.9999 for all BAs. The precision (RSDr) values were < 20% and the recovery values for all amines were in the satisfactory range of 70–120% The developed method was applied to the analysis of 39 ripened meat products samples as retailed in Poland.

Determination of selected biogenic amines in fermented vegetables juices

Fermented vegetables and fruits are a good source of selected vitamins, antioxidants, microelements and revealed immune-boosting properties. The appropriate content of health-promoting compounds and probiotics allows you to qualify juices from fermented vegetables or fruits as better-for-you food. Notwithstanding, biogenic amines in this type of food are also detected due to the fermentation process, which may negatively affect their health-promoting properties. In this study, various biogenic amines were determined in juices obtained during the pressing of fermented vegetables (white and red cabbage, cucumbers, tomatoes, cauliflowers, celery, celery leaves, broccoli, and beetroots). The level of monamines (histamine, tyramine, tryptamine, and phenylethylamine), diamines (putrescine, cadaverine), and polyamines (spermidine and spermine) was discussed. The significant discrepancies between all the tested determined compounds as well as the sums of the BAs in tested samples, were observed. The calculated values of BAs sum varied from 6.36 mg L−1 (fermented tomato juice) to 116.52 mg L−1 (fermented cucumber juice). Among the determined amines, the majority were histamine, tyramine, putrescine, and cadaverine (from 66% to 97–98% of total biogenic amines level). Moreover, depending on the type of tested juice, the amount of histamine and tyramine in the full content of BAs was between 0.44% (for fermented red cabbage juice) and 68% (for fermented broccoli juice). According to our knowledge, this is the first time that the determination of biogenic amines in fermented vegetable juices has been studied.

HPLC/HILIC determination of biogenic amines in wines produced by different winemaking technologies

AbstractThe present study evaluated the effect of winemaking technologies on the concentration of different biogenic amines in Chardonnay wines. Wines produced from sedimented, inoculated must with active dry yeast without malolactic fermentation were compared with wine produced from nonsedimented must spontaneously fermented with malolactic fermentation. Histamine and putrescine concentrations were not significantly different in either variant. The highest concentration of histamine was 0.055 mg L−1, and the highest concentration of putrescine was 1.6 mg L−1 in both variants. Statistically significantly higher values of cadaverine (from 0.06 to 0.07 mg L−1), spermidine (from 0.8 to 1.4 mg L−1), spermine (from 0.15 to 0.25 mg L−1), and isoamylamine (from 0.40 to 0.46 mg L−1) were found in the variant made from nonsedimented must, in which spontaneous malolactic fermentation was performed. The higher concentration of biogenic amines in this variant may be due to the different composition of lactic bacteria during the spontaneous malolactic fermentation. A simplified, unpublished HILIC method of chromatographic separation of biogenic amines without prior deprivation with MS-MS detection was used to determine individual biogenic amines.

Determination of Biogenic Amines in Wine from Chinese Markets Using Ion Chromatography-Tandem Mass Spectrometry.

A method for the determination of nine biogenic amines (BAs) in wine was established using ion chromatography-tandem mass spectrometry (IC-MS/MS) without derivatization. BAs were separated by a cation exchange column (IonPac CG17, 50 mm × 4 mm, 7 µm) with a gradient aqueous formic acid elution. Good linearity was obtained for nine BAs with coefficients of determination (R2) > 0.9972 within the range of 0.01-50 mg/L. The limits of detection and quantification were within the ranges of 0.6-40 µg/L and 2.0-135 µg/L, respectively, with the exception of spermine (SPM). The recoveries were demonstrated within the range of 82.6-103.0%, with relative standard deviations (RSDs) of less than 4.2%. This simple method featuring excellent sensitivity and selectivity was suitable for the quantification of BAs in wines. The occurrence of BAs in 236 wine samples that are commercially available in China was determined. The BA levels in wines of different geographical origins varied significantly. The acute dietary exposure assessment of BAs was carried out by calculating the estimated short-term intake (ESTI) and comparing the acute reference dose (ARfD) specified by the European Food Safety Authority (EFSA). Results showed that the exposure to histamine (HIS) and tyramine (TYR) via the consumption of wines was much lower than the recommended ARfD level for healthy individuals. However, exposure could lead to symptoms in susceptible individuals. These results provided basic data regarding the occurrence and risk of BAs in wines for wine production, health guidance and consumer safety.

The Measurement of Hazardous Biogenic Amines in Non-Alcoholic Beers: Efficient and Applicable Miniaturized Electro-Membrane Extraction Joined to Gas Chromatography-Mass Spectrometry.

The determination of biogenic amines (BAs) as serious food contaminants and chemical indicators of unwanted microbial contamination or deficient processing conditions in non-alcoholic beers is of great interest for the beverage industries. In the present investigation, the combination of hollow fiber-electro-membrane extraction (HF-EME) and dispersive liquid-liquid microextraction (DLLME) followed by gas chromatography-mass spectrometry (GC/MS) was applied for the analysis of histamine, putrescine, tyramine, cadaverine in non-alcoholic beers. EME is fundamentally based on the electrostatic attraction, diffusion and solvability of analytes in a selected acceptor phase. This membrane-based extraction technique promoted selectivity and the enrichment factor. The DLLME process reduced the volumes of organic solvents and make the coupling of HF-EME to the CG/MS conceivable. The leading variables, which have a great effect on extraction recovery, were optimized. The relative standard deviation was achieved between 4.9 and 7.0%. The recoveries were between 94% and 98%. The limit of detection and limit of quantification were found to be 0.92-0.98 ng mL-1 and 3.03-3.23 ng mL-1, respectively. The enrichment factor was calculated in the range 36-41. The achievements revealed that putrescine and tyramine, with concentrations of 3.87 and 2.33 µg g-1, were at the highest concentration in non-alcoholic beers. This offered method with great benefits could help beverage industries to monitor the concentration of BAs in beers and control them.

Fluorescence digital image-based method to measure biogenic amines in Buffalo Mozzarella and other cheeses produced in Brazil

A fluorescence digital image-based (FDIB) method was applied for the determination of total biogenic amines in Mozzarella, Buffalo Mozzarella, Prato and Coalho cheese. For the first time in the literature a FDIB has been applied to quantify biogenic amines (BA) in cheese samples. No analytical methods have been reported before for the analysis of BA in Buffalo Mozzarella. Therefore, two BAs, i.e., Histamine and Tyramine were selected as models to evaluate the behavior of BAs during the derivatization reaction with dansyl chloride (DNS-Cl). The total biogenic amines ranged from 16.98 ± 0.98 mg L−1 to 72.48 ± 1.78 mg L−1 for cheese samples. Similar results with a confidence level of 95% were obtained using high performance liquid chromatography with spectrophotometric detection at 254 nm. The FDIB method developed reduces analytical steps such as extraction of excess of derivatizing agent, purification, removal of the used solvent, pre-concentration of analytes, filtration, and other analytical procedures that are used in HPLC, colorimetry, spectrophotometry, spectrofluorometry and other analytical methods. Thus, the FDIB is faster, low cost and generates less waste, being a more green method compared to the mentioned methods.

Determination of biogenic amines in chicken, beef, and mutton by dansyl chloride microwave derivatization in Malaysia

In this study, an improved dansyl-chloride derivatization technique using a microwave synthesizer was used for the qualitative and quantitative analyses of biogenic amine in the fresh meat samples. The derivatization technique was optimized in terms of temperature, reaction time, and spinning speed. The derivatization method together with a validated reversed-phase HPLC-DAD method was used for the determination of biogenic amines in chicken, beef, and mutton sold in the wet market. The results of the analyses showed that tryptamine, putrescine, and histamine were generally detected in all the three types of meat. Higher levels of histamine were found in chicken and beef. However, low levels of histamine were observed in mutton. Tyramine was either detected low or moderate in all the three types of meat. The biogenic amines of the fresh meat sold in the wet market is generally higher than the reported values. The mechanisms of biogenic amines-dansyl-chloride formation were investigated and proposed. PRACTICAL APPLICATION: The biogenic amine derivatization method was improved. The improved derivatization method can be potentially used for various food products beside meats for routine biogenic amine analyses due to its fast analysis time and simplicity. High levels of biogenic amines were generally found in the meat sold in the wet markets. However, proper handling of the raw meat can reduce the risk of infection.

Development of a High Performance Liquid Chromatography with Diode Array Detector (HPLC-DAD) Method for Determination of Biogenic Amines in Ripened Cheeses.

Biogenic amines (BAs) are organic, basic nitrogenous compounds formed during the decarboxylation of amino acids. A method for the determination of eight biogenic amines (tryptamine, 2-phenyletylamine, putrescine, cadaverine, histamine, tyramine, spermidine, spermine) in ripened cheeses was developed and validated. Cheese samples with the addition of internal standards were extracted with 0.2 M perchloric acid and pre-column derivatized with dansyl chloride at 60 °C for 15 min, purified with toluene and dried under a stream of nitrogen. The samples were analyzed using high performance liquid chromatography with diode array detector (HPLC-DAD). The method was validated with the BAs at three concentration levels: 50, 100, and 200 mg/kg, respectively. The obtained values of correlation coefficient (R2) ranged at 0.9997−0.9998 for all of compounds. The limits of detection (LOD) and quantification (LOQ) were in ranges 1.53−1.88 and 5.13−6.28 mg/kg, respectively. The recovery for all of biogenic amines ranged from 70 to 120% and the precision (RSDr) value were <20%. The validated method was applied to analysis of 35 real ripened cheese samples purchased in Poland.

Simultaneous Determination of Amino Acids and Biogenic Amines by Liquid Chromatography Coupled to Mass Spectrometry for Assessing Wine Quality

Biogenic amines (BAs) and free amino acids (AAs) are low-molecular nitrogenous compounds occurring in a wide range of foodstuffs, found in increased amount in different fermented foods, seafood, and wines. This study deals with the development of an analytical method based on liquid chromatography with tandem mass spectrometry with precolumn derivatization with dansyl chloride for the determination of BAs and AAs in musts, wines, and sparkling wines. The resulting compositional profiles have been exploited as potential descriptors of quality and other oenological issues using chemometric methods including principal component analysis (PCA) and partial analysis of least squares-discriminants (PLS-DA). Proline is the most abundant compound, and other remarkable species are lysine, ethanolamine, tyramine, histamine, and putrescine. Fermented samples (wines and sparkling wines) are much richer in both BAs and free AAs than the initial musts. Significant differences have also been noticed in the quality, as the best products display, in general, lower levels. The dissimilarities in the content of the analytes between the two grape varieties studied (pinot noir and xarel·lo) and those dealing with quality aspects have made it possible to establish a tree to classify the samples based on these two features with excellent classification rates.

Conductive Cloth-Assisted Electromediated Extraction for the Determination of Biogenic Amines from Beverages

Conductive Cloth-Assisted Electromediated Extraction for the Determination of Biogenic Amines from Beverages

Determination of Biogenic Amines in Food and Beverage Samples

Biogenic amines are low-molecular-weight nitrogen compounds that are formed primarily by the decarboxylation of amino acids by microbial enzymes. These active substances are found mainly in various types of food or beverages. At certain concentrations, biogenic amines are essential for many physiological functions but toxic if consumed in large quantities. Therefore, the development and optimization of methods sensitive to determine these substances are very much needed. The determination of biogenic amines in food and beverages by the most commonly used separation methods with different types of detection is covered in this review.