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Electromembrane extraction of biogenic amines in food samples by a microfluidic-chip system followed by dabsyl derivatization prior to high performance liquid chromatography analysis
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CHROMA-359345; No. of Pages 8
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Electromembrane extraction of biogenic amines in food samples by a microfluidic-chip system followed by dabsyl derivatization prior to high performance liquid chromatography analysis Fereshteh Zarghampour a , Yadollah Yamini a,∗ , Mahroo Baharfar a , Mohammad Faraji b a b
Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, 14115-175, Tehran, Iran Faculty of Food Industry and Agriculture, Department of Food Science & Technology, Standard Research Institute (SRI), Karaj, 31745-139, Iran
a r t i c l e
i n f o
Article history: Received 7 March 2018 Received in revised form 18 April 2018 Accepted 22 April 2018 Available online xxx Keywords: On chip electromembrane extraction High performance liquid chromatography Dabsyl chloride Biogenic amines Microfluidic-chip
a b s t r a c t In the present research, an on-chip electromembrane extraction coupled with high performance liquid chromatography was developed for monitoring the trace levels of biogenic amines (BAs), including histamine, tryptamine, putrescine, cadaverine and spermidine in food samples. A porous polypropylene sheet membrane impregnated with an organic solvent was placed between the two parts of the chip device to separate the channels. Two platinum electrodes were mounted at the bottom of these channels, which were connected to a power supply, providing the electrical driving force for migration of ionized analytes from the sample solution through the porous sheet membrane into the acceptor phase. BAs were extracted from 2 mL aqueous sample solutions at neutral pH into 50 L of acidified (HCl 90 mM) acceptor solution. Supported liquid membrane including NPOE containing 10% DEHP was used to ensure efficient extraction. Low voltage of 40 V was applied over the SLMs during extraction time. The influences of fundamental parameters affecting the transport of BAs were optimized. Under the optimized conditions, the relative standard deviations based on four replicate measurements were less than 8.0% and limit of detections were in range of 3.0–8.0 g L−1 . Finally, the method was successfully applied to determinate BAs in the food samples and satisfactory results (recovery > 95.6) were obtained. © 2018 Elsevier B.V. All rights reserved.
1. Introduction BAs are organic bases with low molecular weight and aliphatic, aromatic or heterocyclic structures. They are mainly produced by decarboxylation of amino acids by the metabolic activity of bacteria, plants and animals [1]. The most important biogenic amines are histamine (HIS), tryptamine (TRP), putrescine (PUT), cadaverine (CAD) and spermidine (SPD), which are formed from the free amino acids histidine, tryptophane, ornithine and lysine, respectively. Polyamines also exist in this class of compounds. For instance, SPD is a polymerized form arising from PUT.
Abbreviations: BAs, biogenic amines; HIS, histamine; TRP, tryptamine; PUT, putrescine; CAD, cadaverine; SPD, spermidine; DABS-Cl, dabsyl chloride (4-dimethylaminoazobenzene-4 -sulfony] chloride; DEHP, di-(2-ethylhexyl) phosphate; CEME, on chip electromembrane extraction; EME, electromembrane extraction; ER, extraction recovery; HPLC, high performance liquid chromatography; LOD, limit of detection; NPOE, 2-nitrophenyl octyl ether; PF, preconcentration factor; PPMA, polymethyl methacrylate; RR, relative recovery; RSD, relative standard deviation; SLM, supported liquid membrane; TEHP, tris-(2-ethylhexyl) phosphate. ∗ Corresponding author. E-mail address: [email protected] (Y. Yamini).
Biogenic amines are presented in a wide variety of foods from non-fermented foods such as fish, meat, chocolate, milk and fruit to fermented products like wine, cheese, beer and sauerkraut. They play an important role as source of nitrogen and precursor for the synthesis of hormones, alkaloids, nucleic acids, proteins, amines and food aroma components [2,3]. There are two reasons for the determination of BAs in foods: their potential toxicity and a possibility of using them as food quality indicators [4]. Among all BAs, high concentrations of histamine represent a risk factor for food intoxication, whereas moderate levels may lead to food intolerance. Sensitive persons, with insufficient diamine oxidase activity, suffer from numerous undesirable reactions after consuming foods with significant levels of histamine. Besides spoiled foodstuffs, especially fermented foods contain important levels of BAs, although their concentrations vary extensively not only between different food varieties but also within the varieties themselves [5,6]. Putrescine and cadaverine are essential for cell growth and their participation in human cell growth and proliferation has been studied widely, particularly for their role in tumor growth. The requirement for putrescine increases rapidly in growing tissues (neoplastic growth) [4].
https://doi.org/10.1016/j.chroma.2018.04.046 0021-9673/© 2018 Elsevier B.V. All rights reserved.
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The consumption of foods containing high concentrations of biogenic amines may cause some adverse effects, such as headaches, hypo- or hypertension, migraine, nausea, rash, dizziness and death in severe cases [7]. Several techniques have been reported for determination of biogenic amines. They include thin-layer chromatography (TLC) [8], ion mobility spectrometry [9], high-performance liquid chromatography (HPLC) [10], gas chromatography–mass spectrometry [11] and capillary electrophoretic method (CE) [12]. Analytical determination of BAs is not simple due to the high polarity of these compounds, the need to be derivatized and also the complexity of the real matrices to be analyzed. For these reasons, development of selective and reliable sample preparation methods with high levels of clean-up is an important necessity before the instrumental analysis [13–15]. From this point of view, membrane based microextraction methods that are well known for their cleanup and simplicity could be good candidates for this purpose. Electromembrane extraction (EME) is one of the liquid phase micro extraction methods that was introduced by PedersenBjergaard and coworkers in 2006 [16]. In 2010, for the first time Petersen et al. presented a downscaled EME in a microfluidic chip for sample preparation [17]. Electromembrane extraction is an electrically modulated form of sample preparation, which is based on migration of ionized analytes across a porous membrane impregnated by a proper organic solvent. Miniaturization of EME on the microfluidic platforms is a prominent approach to benefit this conventional method by the advantages of microsystems comprising: higher surface to volume ratio and efficiency, lower required amounts of reagents and solvents and feasibility of application of a repetitive homogeneous electric field whole along the dedicated channels for extraction [18,19]. BAs do not show satisfactory absorption in the visible and ultraviolet range, and so a derivatization procedure was required to make them suitable for analysis by HPLC-UV. So far, different derivatization reagents have been used to derivatize BAs prior to their HPLC analysis. Reagents such as 4-chloro-7-nitrobenzofurazan (NBD-Cl) [20], o-phthaldialdehyde [21], 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) [22] benzoyl chloride [23] and dansyl or dabsyl chlorides [24–26] have been used. Among them, dansyl or dabsyl chloride was found as the most popular and deficient derivatization reagent. Dabsylation procedure is fast, and dabsyl derivatives are very stable. Moreover, dabsyl derivatives show absorbance in the range of 436–460 nm. That way, interferences from UV-absorbing biological compounds present in food extracts are mostly avoided [27,28] in comparison with dansyl chloride reagent. Thus, DBSL-Cl was used as derivatization reagent to increase the sensitivity of the method [29–31]. In the present work, microfluidic-chip system followed by dabsyl derivatization prior to high performance liquid chromatography analysis was developed for determination trace amounts of BAs including HIS,TRP, PUT, CAD and SPD in food samples. To the best of our knowledge, this is the first attempt to extraction of BAs using microfluidic-chip system. Several experimental parameters that influence the BAs microextraction and derivatization performance of the proposed method were investigated and optimized. Finally, figures of merit of the proposed method were compared with previous published methods.
2. Experimental 2.1. Chemicals and reagents BAs and DABS-Cl were obtained from Sigma-Aldrich (Steinhein, Germany). The chemical structures and physicochemical
properties of BAs are provided in Table S1. 2-Nitrophenyl octyl ether (NPOE), tris-(2-ethylhexyl) phosphate (TEHP) and di-(2ethylhexyl) phosphate (DEHP) were purchased from Fluka (Buchs, Switzerland). All chemicals used were analytical reagent grade. Porous polypropylene sheet membranes with porosity of 55%, wall thickness of 200 micro m and pore size of 0.2 micro m were purchased from Membrana (Wuppertal, Germany). Ultrapure water was prepared by a Younglin 370 series aqua MAX purification instrument (Kyounggi-do, Korea). Stock solutions of BAs were prepared in ultrapure water at 1000 mg L−1 . Working mix standard solutions were prepared daily by dilution of the stock solutions with ultrapure water. DABS-Cl was dissolved in acetone at 2 mg mL−1 . Any insoluble residue was removed by centrifugation for 5 min at 3000 rpm at room temperature. Then, the supernatant was kept in refrigerator and used as the dabsylation reagent. 2.2. Preparation of real samples Samples of sausage and kielbasa were mixed and homogenized via a mincer (1 g ± 1 mg). Then, they were put into a 50 mL test tube, and 25 mL of 1% trifloroacetic acid (TFA) was added and vortexed at the speed of 1500 min−1 for 3 min. The suspension was centrifuged at 3000 rpm for 15 min at room temperature. The supernatant was filtered through a paper filter and the pH of the solution was adjusted to 6.0. Then, 1.5 mL (for the sausage sample) or 3 mL (for the kielbasa sample) of this solution was poured into a 5 mL volumetric flask and diluted to the mark with ultrapure water. 2.3. Chromatographic apparatus The separation and detection of the analytes were carried out using an Agilent 1260 HPLC system equipped with a quaternary pump, degasser, a 20 L sample loop and UV–vis detector (Waldbornn, Germany). Results were recorded and analyzed by ChemStation for LC system software (version B.04.03). The separations were accomplished on an ODS-3 C18 column (150 mm × 2.1 mm, with 5 m particle size) provided from MZAnalysenteknik (Maniz, Germany). The separation of BAs was performed under isocratic elution at the flow rate of 1.0 mL min−1 . The mobile phase consisted of 20 mmol L−1 acetate buffer containing 0.2% (v/v) triethylamine (pH = 6.0) and acetonitrile (10:90, v/v). The detector wavelength was set at 440 nm. 2.4. Chip preparation The chip consists of two polymethyl methacrylate (PMMA) parts. In each part, a channel with the length of 30 mm, 500 m deep and 1.0 mm wide was craved. The channel, which was craved at the upper part, acted as the acceptor phase channel, whereas the other one located in the lower part is a flow path for the sample solution. Moreover, three individual holes (a, b and c with I.D. of 0.5 mm) were drilled in each part of the chip based device in which holes a and c were connected to inlet and outlet tubes, whereas hole b was used for the entrance of platinum electrodes with the diameter of 0.2 mm, prepared from Pars Pelatine (Tehran, Iran). In each part of the chip based device, the platinum electrodes were bent and mounted at the bottom of each channel after passing through the hole of c. All channels and holes were milled using a SMG-302 CNC micromilling machine from Sadrafan Gostar Industries (Tehran, Iran). During extraction, the channels of the sample solution and acceptor phase were separated with a small piece of a porous polypropylene sheet membrane, which was impregnated with an organic solvent. The sheet membrane was located between the two parts along the channels and was fixed using four bolts and nuts during the extraction procedure. After each extraction step,
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Fig. 1. Fig. 2. Schematic illustration of the developed analytical procedure (electromembrane extraction + derivatization + final determination).
the porous sheet membrane was replaced by a new one. The sample solution was flown toward the inlet of the sample channel by a syringe pump. In addition, a microsyringe was used for introducing and withdrawing of a microliter volume of acceptor solution into the acceptor phase channel.
2.5. Procedure of electromembrane extraction on a chip piece of propylene sheet, with the dimension of 3 mm × 4 cm, was cut and dipped in NPOE containing 10% (v/v) DEHP to impregnate the organic solvent into the pores of the sheet. The excess amount of the organic solvent was wiped out by a piece of paper sheet. The membrane sheet was mounted between the two parts of the chip device. Two milliliters of the donor phase containing the target analytes was withdrawn into a syringe located on the syringe pump and pumped through the related channel. Fifty microliters of 90 mmol L−1 HCl as the acceptor phase was introduced into the upper channel of the chip device by a microsyringe. After the fulfillment of the extraction, the acceptor phase containing BAs was collected by a microsyringe for derivatization. After each extraction, the channels of the device were carefully washed by ultrapure water and methanol. Fig. 1 illustrates the extraction process schematically.
2.6. Dabsylation of BAs For derivatization, 50 L of standard or treated sample solution was transferred to a vial, and subsequently 10 L of 1.5 mol L−1 sodium bicarbonate buffer (pH = 9.0) and 40 L of the DABS-Cl solution (2.0 mg mL−1 ) were added to the vial. The mixture was vortexed for 1 min and then allowed to react at 70 ◦ C for 10 min in a water bath. Then, the content of the vial was cooled down, and twenty-microliter of the solution was injected to HPLC.
2.7. Calculation of preconcentration factor, extraction recovery and relative recovery The preconcentration factor (PF) was defined as the ratio of the final analyte concentration in the acceptor phase (Cf,a ) to the initial concentration of analytes in the sample solution (Ci,s ): PF =
Cf,a Ci,s
(1)
Where Cf,a was determined according to a calibration graph obtained from the direct injection of BAs standard solutions. The extraction recovery (ER%) was defined as the percentage of the mole
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Fig. 2. The dabsylation reaction between dabsyl chloride and a primary amine.
numbers of analyte extracted into the acceptor phase (nf,a ) to that originally present in the sample solution (ni,s ). ER% =
nf,a
× 100 =
ni,s
ER% = (
Vf,a Vi,s
Cf,a × Vf,a Ci,s × Vi,s
) × PF × 100
× 100
(2) (3)
Where Vf,a and Vi,s indicate the volume of the acceptor phase and sample solution, respectively. Relative recovery (RR) was calculated from the following equation: RR% =
Cfound − Creal Cadded
× 100
Error% = RR − 100
(4) (5)
Where Cfound , Creal and Cadded represent the concentration of the analyte after adding a known amount of the standard into the real sample, the concentration of analyte in the real sample and the concentration of spiked standard solution into the real sample, respectively.
3.1.1. Effect of DABS-Cl volume The effect of DABS-Cl amount on derivatization was studied in the range of 5–100 L of the 2.0 mg mL−1 DABS-Cl solution. Fig. S1a shows that the response of BAs-DABS-Cl derivative increased with the DABS-Cl amount increasing from 5 to 40 L. Further increasing of the DABS-Cl amount beyond 40 L excess had no significant effects on the response. Therefore, 40 L DABS-Cl was chosen for the analysis.
3.1.2. Effect of buffer volume Apart from the analyte, dabsylation occurs at alkaline conditions usually at pH = 9.0 by using sodium bicarbonate buffer [27,29,32,33]. The effect of sodium bicarbonate buffer (pH 9.0) amount on derivatization was studied in the range of 5–20 L of 1.5 mol L−1 bicarbonate buffer. According to the results (Fig. S1b), maximum responses (peak areas) were obtained at 10 L buffer. By increasing buffer volume from 10.0 to 20.0 L, the responses decreased may be as result of decreasing solubility of dabsylation products.
3. Results and discussion 3.1. Derivatization It was mentioned that BAs of interest had no UV absorbance, and so some derivatization procedures were required to make them suitable for analysis by HPLC-UV. Effective parameters on derivatization efficiency, such as DABS-Cl volume, buffer volume and derivatization temperature and time were investigated and optimized [28,29]. Fig. 2. Illustrates the dabsylation reaction between dabsyl chloride and a primary amine.
3.1.3. Effect of derivatization temperature and time The effects of derivatization temperature and time in the range of 60–90 ◦ C and 5–20 min were studied. It was found that derivatization efficiency increased from 60 to 70 ◦ C and after that remained almost constant. This result is in agreement with optimum derivatization temperature of previously published articles [27,29,32,33]. Therefore, derivatization temperature of 70 ◦ C was chosen for the analysis. Maximum signal was observed after 10 min (Fig. S1c). Accordingly, the time of 10 min was used in the next experiments [29,32].
Fig. 3. Effect of applied voltage (a), sample solution flow rate and extraction time for HIS and TRP (b). (Conditions: Analytes were extracted across SLM from 0 mmol L−1 HCl sample solution into 90 mmol L−1 HCl solution by the applied voltage of 60 V and flow rate of 40 L min−1 ).
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Table 1 Figures of merit of on chip electromembrane extraction for the extraction and determination of HIS, TRP, PUT, CAD and SPD. Analyte
LOD (g L−1 )
LOQ (g L−1 )
Linearity (g L−1 )
R2
PFa
ER%
RSD (N = 5)
HIS TRP PUT CAD SPD
8.0 6.0 6.0 6.0 3.0
25.0 15.0 15.0 15.0 10.0
25.0−1800 15.0−1800 15.0−1600 15.0−1800 10.0−2400
0.9902 0.9909 0.9914 0.9933 0.9943
14 16 15 19 19
35 40 37 47 47
8.0 6.3 7.0 5.5 5.8
a
Preconcentration factor at 1000 g L−1 .
3.2. Optimization of effective parameters on CEME 3.2.1. Selection of organic supported liquid membrane The selection of organic supported liquid membrane is of major importance in CEME in order to obtain efficient extraction. For organic solvent selection, the main parameters are as follow: the organic solvent should be compatible with the nature of the sheet membrane to impregnate in its pore and form a very thin organic film, and also the organic solvent must be immiscible with the aqueous phase, certain dipole moment or electrical conductivity to support a relatively low current flow in the system, high permeability to enable phase transfer and electrokinetic migration of the analytes, low volatility and no or less toxicity [18,34]. The effects of different organic solvents such as NPOE, NPOE containing 5, 10 and 15% (v/v) DEHP, also NPOE containing 5 and 10% (v/v) TEHP and NPOE containing 5 and 10% (v/v) hexanoic acid were studied, and the results are shown in Fig. S2a. The results indicated that the best extraction efficiency obtained for NPOE containing 10% (v/v) DEHP. 3.2.2. Effect of sample solution and acceptor phase compositions As well as most extraction methods, pHs of sample solution and corresponding acceptor phase have crucial effects in extraction efficiency of EME. In EME, the analytes should exist as their ionized form to migrate under the electric field. Based on previous studies, increasing the HCl concentration in the acceptor phase of basic analytes enhances the extraction efficiency of EME due to decreasing ion balance (i.e. the ratio of the total ionic concentration in the sample solution to that in the acceptor solution) [14,30]. As shown in Fig. S2c, relatively high peak areas were obtained at 90 mmol L−1 HCl. As HCl concentration in the acceptor solution increased, the extraction efficiency rose. On the other hand, the extraction efficiency is increased by decreasing the HCl concentration in the sample solution. The results are shown in Fig. S2b. The best sample solution composition was obtained in the absence of HCl. The observed decrease in signal under high acidic condition of sample solutions may be attributed to the competition among ionized analytes and proton ions to migrate toward SLM, which increased the thickness of the double layer around SLM and reduced the mass transfer through the SLM and into the acceptor phase. However, there are some restrictions to use higher concentration of HCl in acceptor phase and sample solutions because increasing the HCl concentration raises the possibility of evolving bubbles and the electrolysis reactions, increases Joule heating and therefore results in instability of SLM, fluctuation of acceptor phase volume and a decrease in repeatability [18,34,35]. 3.2.3. Effect of applied voltage In EME, the electric field which is provided by the applied potential between electrodes, stimulates the transfer of analytes through the SLM into the acceptor phase. Therefore, mass transfer is greatly dependent on the electric field, so it is expected that extraction efficiency would increase by increasing the applied voltage. However, at the high applied voltages, several problems such as bobble formation due to electrolysis process, SLM punctuation and spark-
ing may occur [35]. The effect of applied voltage on the extraction of BAs was studied in the range of 30–70 V while 0 mmol L−1 HCl and 90 mmol L−1 HCl were used as the donor and acceptor solutions, respectively. As it can be seen in Fig. 3a, the highest signal was obtained at 40 V. At lower voltages, the extraction was not completed; however, higher voltages probably caused partial back extraction to the SLM and unstable conditions in SLM due to Joule heating [35]. Therefore, electrical potential of 40 V was applied for the future experiments. 3.2.4. Effect of sample solution flow rate and extraction time A syringe pump was used to pass the sample solution into the CEME extraction device. The flow rate of the sample solution is one of the most important parameters in increasing the kinetics of mass transfer and extraction efficiency. In addition, extraction time is inversely proportional to the sample flow rate. Therefore, the extraction time and sample flow rate were investigated together. The effect of the sample solution flow rate on the extraction of BAs was studied in the range of 20.0–80.0 L min−1 under optimum conditions. The results are shown in Fig. 3b. The best sample solution flow rate was obtained at 30.0 L min−1 . At shorter extraction times or higher sample solution flow rates extraction efficiency decreased because of, target analytes do not have enough time to pass through the SLM into acceptor phase. Moreover, at higher sample flow rates, punctuation of porous membrane and SLM was observed due to the creation of high back-pressures into the sample solution channel [18,34]. 3.3. Method validation To verify the practical applicability of the proposed technique, figures of merit of the proposed method were studied by using standard solutions of BAs in ultrapure water. The limit of detection (LOD) and the limit of quantification (LOQ) were calculated according to the signal to noise ratio of S/N = 3 and S/N = 10 respectively. Optimal conditions were applied to find out linearity, repeatability, LOQ and LODs of this method, as summarized in Table 1. The obtained LODs for HIS, TRP, PUT, CAD and SPD are 8.0, 6.0, 6.0, 6.0 and 3.0 g L−1 , with limit of quantification (LOQs) of 25.0, 15.0, 15.0, 15.0 and 10.0 g L−1 , respectively. Calibration graphs were constructed by plotting peak areas against the amine concentrations. The calibration curves were linear in the range of 25.0-1800, 15.0-1800, 15.0-1600, 15.0-1800 and 10.0–2400 g L−1 for HIS, TRP, PUT, CAD and SPD, respectively. Repeatability of the proposed method was also tested by five parallel analyses with concentration 1000 g L−1 of mixed BAs. It was found that the relative standard deviations (RSD%) for HIS, TRP, PUT, CAD and SPD were 8.0, 6.3, 7.0, 5.5 and 5.8%, respectively. 3.4. Application of the proposed method for analysis of real samples In order to illustrate the performance of the proposed technique for the assay of BAs, it was applied to the determination of the BAs concentration in two meat product samples, including kiel-
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Fig. 4. Chromatograms obtained after CEME of (A) Chromatograms of non-spiked (a) and 120 g L−1 (b) spiked sausage sample and (B) non-spiked (a), 40 g L−1 (b) spiked kielbasa sample.
Table 2 Determination of BAs in food samples. Creal ± SD (mg kg−1 )
Sample
Analyte
a
Sausage
HIS TRP PUT CAD SPD HIS TRP PUT CAD SPD
3.3 ± 0.2
Kielbasa
a b
b
Creal ± SD (g L−1 )
19.9 ± 1.2 1.491.49
Cadded (g L−1 )
Cfound ± SD (g L−1 )
RSD% (n = 5)
RR%
Error%
120.0 120.0 120.0 120.0 120.0 40.0 40.0 40.0 40.0 40.0
137.8 ± 10.3 127.1 ± 10.3 154.5 ± 10.5 143.1 ± 8.2 134.4 ± 8.1 72.2 ± 5.0 42.0 ± 3.0 102.9 ± 6.0 41.8 ± 2.7 80.8 ± 5.9
7.5 8.1 6.8 5.7 6.0 6.9 7.1 5.8 6.5 7.3
98.25 105.91 103.50 103.16 97.0 98.00 105.0 95.0 104.5 96.5
−1.7 5.9 3.5 3.2 −3.0 −2.0 5.0 5.0 4.5 −3.5
Concentration of analytes in treated samples. Concentration of analytes in untreated samples.
basa and sausage, under optimum conditions. The obtained results were illustrated in Fig. 4. The concentrations of HIS, TRP, PUT, CAD and SPD were calculated from the regression equation obtained from calibration curves. The results of this study are presented in Table 2. In particular, PUT was found to be the highest value in sausage and kielbasa samples (30.3 ± 1.9 and 64.9 ± 2.7 mg L−1 respectively). TRP and SPD were found in the lowest amount in sausage sample (
lytes from complicated matrices. In addition, acceptable RSD% values show precision of this technique. 3.5. Conclusion In the present paper, electromembrane extraction by a microfluidic-chip system coupled with high performance liquid chromatography was developed for the analysis of trace amounts of BAs from food samples. The effect of various parameters affecting the extraction efficiency of the on chip EME procedure was investigated and optimized. Making the extraction possible from the complex of the real matrices, providing considerable sample clean-up and acceptable LODs are the advantages of the proposed
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Table 3 Comparison of figures of merit of CEME with other analytical techniques for determination of BAs in food samples. Method
Matrix
LOD (g L−1 )
LOQ (g L−1 )
RSD
Reference
RP–HPLC with diode array detector
red and white wines
wines
TRP = 40.0 PUT = 30.0 CAD = 30.0 HIS = 60.0 SPD = 90. –
Situ derivatization hollow fibre liquid-phase microextraction HPLC-UV
shrimp sauce and tomato ketchup
Liquid chromatography
sausage
TRP = 9.91 PUT = 2.65 CAD = 8.96 HIS = 9.47 SPD = 8.32 HIS = 1.77 TRP = 3.45 PUT = 1.94 CAD = 1.16 SPD = 1.39 TRP = 4.3 PUT = 6.5 CAD = 4.1 HIS = 3.1 SPD = 3.9 HIS = 2.30 TRP = 3.48 PUT = 6.69 CAD = 3.19 SPD = 3.93
[10]
Reversed-phase high-performance liquid chromatography
Ion-pair high-performance liquid chromatography
Spinach, Hazelnut, Banana, Potato and Chocolate
Kielbasa and sausage
HIS = 1.0.0 TRP = 4.5 PUT = 2.3 CAD = 1.4 SPD = 1.9 HIS = 8.0 TRP = 6.3 PUT = 7.0 CAD = 5.5 SPD = 5.8
[36]
CEME
TRP = 10.0 PUT = 10.0 CAD = 10.0 HIS = 20.0 SPD = 30.0 HIS = 16.7 TRP = 32.5 PUT = 61.3 CAD = 10.3 SPD = 13.2 TRP = 20.0 PUT = 10.0 CAD = 10.0 HIS = 10.0 SPD = 20.0 HIS = 0.0012 TRP = .0028 PUT = 0.0009 CAD = 0.0011 SPD = 0.0011 (ng) HIS = 20.0 TRP = 40.0 PUT = 10.0 CAD = 10.0 SPD = 20.0 HIS = 8.0 TRP = 6.0 PUT = 6.0 CAD = 6.0 SPD = 3.0
method. The method can be applied to preconcentration and determination of BAs in various food samples. In Table 3, a comparison of this method with some other reported methods for determination of BAs is presented. As this table illustrates, the proposed method is comparable with most previously reported methods from the standpoint of LODs and RSD values. Apart from the excellent cleanup that this method offers, the main advantage of the proposed method is the low required amount of sample and organic solvents. In conclusion, the followings are some good features of the developed method: No need to clean-up of extract, no need to solvent removal, low energy consumption, miniaturization of extraction setup, low samples size, using a few microlitter of the reagent, using very dilute acids, low waste and so on. Thus it could be considered as a green method for determination of BAs in food samples [36,37]. Acknowledgments This project was financially supported by Iran National Science Foundation (INSF) – grant number 95005963. The authors gratefully acknowledge the support of INSF and Tarbiat Modares University. Appendix A. Supplementary data Supplementary data associated with this article can be found, in the online version, at https://doi.org/10.1016/j.chroma.2018.04. 046. References [1] M.H. Silla Santos, Biogenic amines: their importance in foods, Int. J. Food Microbiol. 29 (1996) 213–231. [2] M.A. Awan, I. Fleet, C.L.P. Thomas, Determination of biogenic diamines with a vaporisation derivatisation approach using solid-phase microextraction gas chromatography–mass spectrometry, Food Chem. 111 (2008) 462–468.
TRP = 60.0 PUT = 30.0 CAD = 40.0 HIS = 10.0 SPD = 80.0 –
HIS = 50.0 TRP = 130.0 PUT = 30.0 CAD = 40.0 SPD = 70.0 HIS = 25.0 TRP = 15.0 PUT = 15.0 CAD = 15.0 SPD = 10.0
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Electromembrane extraction of biogenic amines in food samples by a microfluidic-chip system followed by dabsyl derivatization prior to high performance liquid chromatography analysis Fereshteh Zarghampour a , Yadollah Yamini a,∗ , Mahroo Baharfar a , Mohammad Faraji b a b
Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, 14115-175, Tehran, Iran Faculty of Food Industry and Agriculture, Department of Food Science & Technology, Standard Research Institute (SRI), Karaj, 31745-139, Iran
a r t i c l e
i n f o
Article history: Received 7 March 2018 Received in revised form 18 April 2018 Accepted 22 April 2018 Available online xxx Keywords: On chip electromembrane extraction High performance liquid chromatography Dabsyl chloride Biogenic amines Microfluidic-chip
a b s t r a c t In the present research, an on-chip electromembrane extraction coupled with high performance liquid chromatography was developed for monitoring the trace levels of biogenic amines (BAs), including histamine, tryptamine, putrescine, cadaverine and spermidine in food samples. A porous polypropylene sheet membrane impregnated with an organic solvent was placed between the two parts of the chip device to separate the channels. Two platinum electrodes were mounted at the bottom of these channels, which were connected to a power supply, providing the electrical driving force for migration of ionized analytes from the sample solution through the porous sheet membrane into the acceptor phase. BAs were extracted from 2 mL aqueous sample solutions at neutral pH into 50 L of acidified (HCl 90 mM) acceptor solution. Supported liquid membrane including NPOE containing 10% DEHP was used to ensure efficient extraction. Low voltage of 40 V was applied over the SLMs during extraction time. The influences of fundamental parameters affecting the transport of BAs were optimized. Under the optimized conditions, the relative standard deviations based on four replicate measurements were less than 8.0% and limit of detections were in range of 3.0–8.0 g L−1 . Finally, the method was successfully applied to determinate BAs in the food samples and satisfactory results (recovery > 95.6) were obtained. © 2018 Elsevier B.V. All rights reserved.
1. Introduction BAs are organic bases with low molecular weight and aliphatic, aromatic or heterocyclic structures. They are mainly produced by decarboxylation of amino acids by the metabolic activity of bacteria, plants and animals [1]. The most important biogenic amines are histamine (HIS), tryptamine (TRP), putrescine (PUT), cadaverine (CAD) and spermidine (SPD), which are formed from the free amino acids histidine, tryptophane, ornithine and lysine, respectively. Polyamines also exist in this class of compounds. For instance, SPD is a polymerized form arising from PUT.
Abbreviations: BAs, biogenic amines; HIS, histamine; TRP, tryptamine; PUT, putrescine; CAD, cadaverine; SPD, spermidine; DABS-Cl, dabsyl chloride (4-dimethylaminoazobenzene-4 -sulfony] chloride; DEHP, di-(2-ethylhexyl) phosphate; CEME, on chip electromembrane extraction; EME, electromembrane extraction; ER, extraction recovery; HPLC, high performance liquid chromatography; LOD, limit of detection; NPOE, 2-nitrophenyl octyl ether; PF, preconcentration factor; PPMA, polymethyl methacrylate; RR, relative recovery; RSD, relative standard deviation; SLM, supported liquid membrane; TEHP, tris-(2-ethylhexyl) phosphate. ∗ Corresponding author. E-mail address: [email protected] (Y. Yamini).
Biogenic amines are presented in a wide variety of foods from non-fermented foods such as fish, meat, chocolate, milk and fruit to fermented products like wine, cheese, beer and sauerkraut. They play an important role as source of nitrogen and precursor for the synthesis of hormones, alkaloids, nucleic acids, proteins, amines and food aroma components [2,3]. There are two reasons for the determination of BAs in foods: their potential toxicity and a possibility of using them as food quality indicators [4]. Among all BAs, high concentrations of histamine represent a risk factor for food intoxication, whereas moderate levels may lead to food intolerance. Sensitive persons, with insufficient diamine oxidase activity, suffer from numerous undesirable reactions after consuming foods with significant levels of histamine. Besides spoiled foodstuffs, especially fermented foods contain important levels of BAs, although their concentrations vary extensively not only between different food varieties but also within the varieties themselves [5,6]. Putrescine and cadaverine are essential for cell growth and their participation in human cell growth and proliferation has been studied widely, particularly for their role in tumor growth. The requirement for putrescine increases rapidly in growing tissues (neoplastic growth) [4].
https://doi.org/10.1016/j.chroma.2018.04.046 0021-9673/© 2018 Elsevier B.V. All rights reserved.
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The consumption of foods containing high concentrations of biogenic amines may cause some adverse effects, such as headaches, hypo- or hypertension, migraine, nausea, rash, dizziness and death in severe cases [7]. Several techniques have been reported for determination of biogenic amines. They include thin-layer chromatography (TLC) [8], ion mobility spectrometry [9], high-performance liquid chromatography (HPLC) [10], gas chromatography–mass spectrometry [11] and capillary electrophoretic method (CE) [12]. Analytical determination of BAs is not simple due to the high polarity of these compounds, the need to be derivatized and also the complexity of the real matrices to be analyzed. For these reasons, development of selective and reliable sample preparation methods with high levels of clean-up is an important necessity before the instrumental analysis [13–15]. From this point of view, membrane based microextraction methods that are well known for their cleanup and simplicity could be good candidates for this purpose. Electromembrane extraction (EME) is one of the liquid phase micro extraction methods that was introduced by PedersenBjergaard and coworkers in 2006 [16]. In 2010, for the first time Petersen et al. presented a downscaled EME in a microfluidic chip for sample preparation [17]. Electromembrane extraction is an electrically modulated form of sample preparation, which is based on migration of ionized analytes across a porous membrane impregnated by a proper organic solvent. Miniaturization of EME on the microfluidic platforms is a prominent approach to benefit this conventional method by the advantages of microsystems comprising: higher surface to volume ratio and efficiency, lower required amounts of reagents and solvents and feasibility of application of a repetitive homogeneous electric field whole along the dedicated channels for extraction [18,19]. BAs do not show satisfactory absorption in the visible and ultraviolet range, and so a derivatization procedure was required to make them suitable for analysis by HPLC-UV. So far, different derivatization reagents have been used to derivatize BAs prior to their HPLC analysis. Reagents such as 4-chloro-7-nitrobenzofurazan (NBD-Cl) [20], o-phthaldialdehyde [21], 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) [22] benzoyl chloride [23] and dansyl or dabsyl chlorides [24–26] have been used. Among them, dansyl or dabsyl chloride was found as the most popular and deficient derivatization reagent. Dabsylation procedure is fast, and dabsyl derivatives are very stable. Moreover, dabsyl derivatives show absorbance in the range of 436–460 nm. That way, interferences from UV-absorbing biological compounds present in food extracts are mostly avoided [27,28] in comparison with dansyl chloride reagent. Thus, DBSL-Cl was used as derivatization reagent to increase the sensitivity of the method [29–31]. In the present work, microfluidic-chip system followed by dabsyl derivatization prior to high performance liquid chromatography analysis was developed for determination trace amounts of BAs including HIS,TRP, PUT, CAD and SPD in food samples. To the best of our knowledge, this is the first attempt to extraction of BAs using microfluidic-chip system. Several experimental parameters that influence the BAs microextraction and derivatization performance of the proposed method were investigated and optimized. Finally, figures of merit of the proposed method were compared with previous published methods.
2. Experimental 2.1. Chemicals and reagents BAs and DABS-Cl were obtained from Sigma-Aldrich (Steinhein, Germany). The chemical structures and physicochemical
properties of BAs are provided in Table S1. 2-Nitrophenyl octyl ether (NPOE), tris-(2-ethylhexyl) phosphate (TEHP) and di-(2ethylhexyl) phosphate (DEHP) were purchased from Fluka (Buchs, Switzerland). All chemicals used were analytical reagent grade. Porous polypropylene sheet membranes with porosity of 55%, wall thickness of 200 micro m and pore size of 0.2 micro m were purchased from Membrana (Wuppertal, Germany). Ultrapure water was prepared by a Younglin 370 series aqua MAX purification instrument (Kyounggi-do, Korea). Stock solutions of BAs were prepared in ultrapure water at 1000 mg L−1 . Working mix standard solutions were prepared daily by dilution of the stock solutions with ultrapure water. DABS-Cl was dissolved in acetone at 2 mg mL−1 . Any insoluble residue was removed by centrifugation for 5 min at 3000 rpm at room temperature. Then, the supernatant was kept in refrigerator and used as the dabsylation reagent. 2.2. Preparation of real samples Samples of sausage and kielbasa were mixed and homogenized via a mincer (1 g ± 1 mg). Then, they were put into a 50 mL test tube, and 25 mL of 1% trifloroacetic acid (TFA) was added and vortexed at the speed of 1500 min−1 for 3 min. The suspension was centrifuged at 3000 rpm for 15 min at room temperature. The supernatant was filtered through a paper filter and the pH of the solution was adjusted to 6.0. Then, 1.5 mL (for the sausage sample) or 3 mL (for the kielbasa sample) of this solution was poured into a 5 mL volumetric flask and diluted to the mark with ultrapure water. 2.3. Chromatographic apparatus The separation and detection of the analytes were carried out using an Agilent 1260 HPLC system equipped with a quaternary pump, degasser, a 20 L sample loop and UV–vis detector (Waldbornn, Germany). Results were recorded and analyzed by ChemStation for LC system software (version B.04.03). The separations were accomplished on an ODS-3 C18 column (150 mm × 2.1 mm, with 5 m particle size) provided from MZAnalysenteknik (Maniz, Germany). The separation of BAs was performed under isocratic elution at the flow rate of 1.0 mL min−1 . The mobile phase consisted of 20 mmol L−1 acetate buffer containing 0.2% (v/v) triethylamine (pH = 6.0) and acetonitrile (10:90, v/v). The detector wavelength was set at 440 nm. 2.4. Chip preparation The chip consists of two polymethyl methacrylate (PMMA) parts. In each part, a channel with the length of 30 mm, 500 m deep and 1.0 mm wide was craved. The channel, which was craved at the upper part, acted as the acceptor phase channel, whereas the other one located in the lower part is a flow path for the sample solution. Moreover, three individual holes (a, b and c with I.D. of 0.5 mm) were drilled in each part of the chip based device in which holes a and c were connected to inlet and outlet tubes, whereas hole b was used for the entrance of platinum electrodes with the diameter of 0.2 mm, prepared from Pars Pelatine (Tehran, Iran). In each part of the chip based device, the platinum electrodes were bent and mounted at the bottom of each channel after passing through the hole of c. All channels and holes were milled using a SMG-302 CNC micromilling machine from Sadrafan Gostar Industries (Tehran, Iran). During extraction, the channels of the sample solution and acceptor phase were separated with a small piece of a porous polypropylene sheet membrane, which was impregnated with an organic solvent. The sheet membrane was located between the two parts along the channels and was fixed using four bolts and nuts during the extraction procedure. After each extraction step,
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Fig. 1. Fig. 2. Schematic illustration of the developed analytical procedure (electromembrane extraction + derivatization + final determination).
the porous sheet membrane was replaced by a new one. The sample solution was flown toward the inlet of the sample channel by a syringe pump. In addition, a microsyringe was used for introducing and withdrawing of a microliter volume of acceptor solution into the acceptor phase channel.
2.5. Procedure of electromembrane extraction on a chip piece of propylene sheet, with the dimension of 3 mm × 4 cm, was cut and dipped in NPOE containing 10% (v/v) DEHP to impregnate the organic solvent into the pores of the sheet. The excess amount of the organic solvent was wiped out by a piece of paper sheet. The membrane sheet was mounted between the two parts of the chip device. Two milliliters of the donor phase containing the target analytes was withdrawn into a syringe located on the syringe pump and pumped through the related channel. Fifty microliters of 90 mmol L−1 HCl as the acceptor phase was introduced into the upper channel of the chip device by a microsyringe. After the fulfillment of the extraction, the acceptor phase containing BAs was collected by a microsyringe for derivatization. After each extraction, the channels of the device were carefully washed by ultrapure water and methanol. Fig. 1 illustrates the extraction process schematically.
2.6. Dabsylation of BAs For derivatization, 50 L of standard or treated sample solution was transferred to a vial, and subsequently 10 L of 1.5 mol L−1 sodium bicarbonate buffer (pH = 9.0) and 40 L of the DABS-Cl solution (2.0 mg mL−1 ) were added to the vial. The mixture was vortexed for 1 min and then allowed to react at 70 ◦ C for 10 min in a water bath. Then, the content of the vial was cooled down, and twenty-microliter of the solution was injected to HPLC.
2.7. Calculation of preconcentration factor, extraction recovery and relative recovery The preconcentration factor (PF) was defined as the ratio of the final analyte concentration in the acceptor phase (Cf,a ) to the initial concentration of analytes in the sample solution (Ci,s ): PF =
Cf,a Ci,s
(1)
Where Cf,a was determined according to a calibration graph obtained from the direct injection of BAs standard solutions. The extraction recovery (ER%) was defined as the percentage of the mole
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Fig. 2. The dabsylation reaction between dabsyl chloride and a primary amine.
numbers of analyte extracted into the acceptor phase (nf,a ) to that originally present in the sample solution (ni,s ). ER% =
nf,a
× 100 =
ni,s
ER% = (
Vf,a Vi,s
Cf,a × Vf,a Ci,s × Vi,s
) × PF × 100
× 100
(2) (3)
Where Vf,a and Vi,s indicate the volume of the acceptor phase and sample solution, respectively. Relative recovery (RR) was calculated from the following equation: RR% =
Cfound − Creal Cadded
× 100
Error% = RR − 100
(4) (5)
Where Cfound , Creal and Cadded represent the concentration of the analyte after adding a known amount of the standard into the real sample, the concentration of analyte in the real sample and the concentration of spiked standard solution into the real sample, respectively.
3.1.1. Effect of DABS-Cl volume The effect of DABS-Cl amount on derivatization was studied in the range of 5–100 L of the 2.0 mg mL−1 DABS-Cl solution. Fig. S1a shows that the response of BAs-DABS-Cl derivative increased with the DABS-Cl amount increasing from 5 to 40 L. Further increasing of the DABS-Cl amount beyond 40 L excess had no significant effects on the response. Therefore, 40 L DABS-Cl was chosen for the analysis.
3.1.2. Effect of buffer volume Apart from the analyte, dabsylation occurs at alkaline conditions usually at pH = 9.0 by using sodium bicarbonate buffer [27,29,32,33]. The effect of sodium bicarbonate buffer (pH 9.0) amount on derivatization was studied in the range of 5–20 L of 1.5 mol L−1 bicarbonate buffer. According to the results (Fig. S1b), maximum responses (peak areas) were obtained at 10 L buffer. By increasing buffer volume from 10.0 to 20.0 L, the responses decreased may be as result of decreasing solubility of dabsylation products.
3. Results and discussion 3.1. Derivatization It was mentioned that BAs of interest had no UV absorbance, and so some derivatization procedures were required to make them suitable for analysis by HPLC-UV. Effective parameters on derivatization efficiency, such as DABS-Cl volume, buffer volume and derivatization temperature and time were investigated and optimized [28,29]. Fig. 2. Illustrates the dabsylation reaction between dabsyl chloride and a primary amine.
3.1.3. Effect of derivatization temperature and time The effects of derivatization temperature and time in the range of 60–90 ◦ C and 5–20 min were studied. It was found that derivatization efficiency increased from 60 to 70 ◦ C and after that remained almost constant. This result is in agreement with optimum derivatization temperature of previously published articles [27,29,32,33]. Therefore, derivatization temperature of 70 ◦ C was chosen for the analysis. Maximum signal was observed after 10 min (Fig. S1c). Accordingly, the time of 10 min was used in the next experiments [29,32].
Fig. 3. Effect of applied voltage (a), sample solution flow rate and extraction time for HIS and TRP (b). (Conditions: Analytes were extracted across SLM from 0 mmol L−1 HCl sample solution into 90 mmol L−1 HCl solution by the applied voltage of 60 V and flow rate of 40 L min−1 ).
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Table 1 Figures of merit of on chip electromembrane extraction for the extraction and determination of HIS, TRP, PUT, CAD and SPD. Analyte
LOD (g L−1 )
LOQ (g L−1 )
Linearity (g L−1 )
R2
PFa
ER%
RSD (N = 5)
HIS TRP PUT CAD SPD
8.0 6.0 6.0 6.0 3.0
25.0 15.0 15.0 15.0 10.0
25.0−1800 15.0−1800 15.0−1600 15.0−1800 10.0−2400
0.9902 0.9909 0.9914 0.9933 0.9943
14 16 15 19 19
35 40 37 47 47
8.0 6.3 7.0 5.5 5.8
a
Preconcentration factor at 1000 g L−1 .
3.2. Optimization of effective parameters on CEME 3.2.1. Selection of organic supported liquid membrane The selection of organic supported liquid membrane is of major importance in CEME in order to obtain efficient extraction. For organic solvent selection, the main parameters are as follow: the organic solvent should be compatible with the nature of the sheet membrane to impregnate in its pore and form a very thin organic film, and also the organic solvent must be immiscible with the aqueous phase, certain dipole moment or electrical conductivity to support a relatively low current flow in the system, high permeability to enable phase transfer and electrokinetic migration of the analytes, low volatility and no or less toxicity [18,34]. The effects of different organic solvents such as NPOE, NPOE containing 5, 10 and 15% (v/v) DEHP, also NPOE containing 5 and 10% (v/v) TEHP and NPOE containing 5 and 10% (v/v) hexanoic acid were studied, and the results are shown in Fig. S2a. The results indicated that the best extraction efficiency obtained for NPOE containing 10% (v/v) DEHP. 3.2.2. Effect of sample solution and acceptor phase compositions As well as most extraction methods, pHs of sample solution and corresponding acceptor phase have crucial effects in extraction efficiency of EME. In EME, the analytes should exist as their ionized form to migrate under the electric field. Based on previous studies, increasing the HCl concentration in the acceptor phase of basic analytes enhances the extraction efficiency of EME due to decreasing ion balance (i.e. the ratio of the total ionic concentration in the sample solution to that in the acceptor solution) [14,30]. As shown in Fig. S2c, relatively high peak areas were obtained at 90 mmol L−1 HCl. As HCl concentration in the acceptor solution increased, the extraction efficiency rose. On the other hand, the extraction efficiency is increased by decreasing the HCl concentration in the sample solution. The results are shown in Fig. S2b. The best sample solution composition was obtained in the absence of HCl. The observed decrease in signal under high acidic condition of sample solutions may be attributed to the competition among ionized analytes and proton ions to migrate toward SLM, which increased the thickness of the double layer around SLM and reduced the mass transfer through the SLM and into the acceptor phase. However, there are some restrictions to use higher concentration of HCl in acceptor phase and sample solutions because increasing the HCl concentration raises the possibility of evolving bubbles and the electrolysis reactions, increases Joule heating and therefore results in instability of SLM, fluctuation of acceptor phase volume and a decrease in repeatability [18,34,35]. 3.2.3. Effect of applied voltage In EME, the electric field which is provided by the applied potential between electrodes, stimulates the transfer of analytes through the SLM into the acceptor phase. Therefore, mass transfer is greatly dependent on the electric field, so it is expected that extraction efficiency would increase by increasing the applied voltage. However, at the high applied voltages, several problems such as bobble formation due to electrolysis process, SLM punctuation and spark-
ing may occur [35]. The effect of applied voltage on the extraction of BAs was studied in the range of 30–70 V while 0 mmol L−1 HCl and 90 mmol L−1 HCl were used as the donor and acceptor solutions, respectively. As it can be seen in Fig. 3a, the highest signal was obtained at 40 V. At lower voltages, the extraction was not completed; however, higher voltages probably caused partial back extraction to the SLM and unstable conditions in SLM due to Joule heating [35]. Therefore, electrical potential of 40 V was applied for the future experiments. 3.2.4. Effect of sample solution flow rate and extraction time A syringe pump was used to pass the sample solution into the CEME extraction device. The flow rate of the sample solution is one of the most important parameters in increasing the kinetics of mass transfer and extraction efficiency. In addition, extraction time is inversely proportional to the sample flow rate. Therefore, the extraction time and sample flow rate were investigated together. The effect of the sample solution flow rate on the extraction of BAs was studied in the range of 20.0–80.0 L min−1 under optimum conditions. The results are shown in Fig. 3b. The best sample solution flow rate was obtained at 30.0 L min−1 . At shorter extraction times or higher sample solution flow rates extraction efficiency decreased because of, target analytes do not have enough time to pass through the SLM into acceptor phase. Moreover, at higher sample flow rates, punctuation of porous membrane and SLM was observed due to the creation of high back-pressures into the sample solution channel [18,34]. 3.3. Method validation To verify the practical applicability of the proposed technique, figures of merit of the proposed method were studied by using standard solutions of BAs in ultrapure water. The limit of detection (LOD) and the limit of quantification (LOQ) were calculated according to the signal to noise ratio of S/N = 3 and S/N = 10 respectively. Optimal conditions were applied to find out linearity, repeatability, LOQ and LODs of this method, as summarized in Table 1. The obtained LODs for HIS, TRP, PUT, CAD and SPD are 8.0, 6.0, 6.0, 6.0 and 3.0 g L−1 , with limit of quantification (LOQs) of 25.0, 15.0, 15.0, 15.0 and 10.0 g L−1 , respectively. Calibration graphs were constructed by plotting peak areas against the amine concentrations. The calibration curves were linear in the range of 25.0-1800, 15.0-1800, 15.0-1600, 15.0-1800 and 10.0–2400 g L−1 for HIS, TRP, PUT, CAD and SPD, respectively. Repeatability of the proposed method was also tested by five parallel analyses with concentration 1000 g L−1 of mixed BAs. It was found that the relative standard deviations (RSD%) for HIS, TRP, PUT, CAD and SPD were 8.0, 6.3, 7.0, 5.5 and 5.8%, respectively. 3.4. Application of the proposed method for analysis of real samples In order to illustrate the performance of the proposed technique for the assay of BAs, it was applied to the determination of the BAs concentration in two meat product samples, including kiel-
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Fig. 4. Chromatograms obtained after CEME of (A) Chromatograms of non-spiked (a) and 120 g L−1 (b) spiked sausage sample and (B) non-spiked (a), 40 g L−1 (b) spiked kielbasa sample.
Table 2 Determination of BAs in food samples. Creal ± SD (mg kg−1 )
Sample
Analyte
a
Sausage
HIS TRP PUT CAD SPD HIS TRP PUT CAD SPD
3.3 ± 0.2
Kielbasa
a b
b
Creal ± SD (g L−1 )
19.9 ± 1.2 1.491.49
Cadded (g L−1 )
Cfound ± SD (g L−1 )
RSD% (n = 5)
RR%
Error%
120.0 120.0 120.0 120.0 120.0 40.0 40.0 40.0 40.0 40.0
137.8 ± 10.3 127.1 ± 10.3 154.5 ± 10.5 143.1 ± 8.2 134.4 ± 8.1 72.2 ± 5.0 42.0 ± 3.0 102.9 ± 6.0 41.8 ± 2.7 80.8 ± 5.9
7.5 8.1 6.8 5.7 6.0 6.9 7.1 5.8 6.5 7.3
98.25 105.91 103.50 103.16 97.0 98.00 105.0 95.0 104.5 96.5
−1.7 5.9 3.5 3.2 −3.0 −2.0 5.0 5.0 4.5 −3.5
Concentration of analytes in treated samples. Concentration of analytes in untreated samples.
basa and sausage, under optimum conditions. The obtained results were illustrated in Fig. 4. The concentrations of HIS, TRP, PUT, CAD and SPD were calculated from the regression equation obtained from calibration curves. The results of this study are presented in Table 2. In particular, PUT was found to be the highest value in sausage and kielbasa samples (30.3 ± 1.9 and 64.9 ± 2.7 mg L−1 respectively). TRP and SPD were found in the lowest amount in sausage sample (
lytes from complicated matrices. In addition, acceptable RSD% values show precision of this technique. 3.5. Conclusion In the present paper, electromembrane extraction by a microfluidic-chip system coupled with high performance liquid chromatography was developed for the analysis of trace amounts of BAs from food samples. The effect of various parameters affecting the extraction efficiency of the on chip EME procedure was investigated and optimized. Making the extraction possible from the complex of the real matrices, providing considerable sample clean-up and acceptable LODs are the advantages of the proposed
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Table 3 Comparison of figures of merit of CEME with other analytical techniques for determination of BAs in food samples. Method
Matrix
LOD (g L−1 )
LOQ (g L−1 )
RSD
Reference
RP–HPLC with diode array detector
red and white wines
wines
TRP = 40.0 PUT = 30.0 CAD = 30.0 HIS = 60.0 SPD = 90. –
Situ derivatization hollow fibre liquid-phase microextraction HPLC-UV
shrimp sauce and tomato ketchup
Liquid chromatography
sausage
TRP = 9.91 PUT = 2.65 CAD = 8.96 HIS = 9.47 SPD = 8.32 HIS = 1.77 TRP = 3.45 PUT = 1.94 CAD = 1.16 SPD = 1.39 TRP = 4.3 PUT = 6.5 CAD = 4.1 HIS = 3.1 SPD = 3.9 HIS = 2.30 TRP = 3.48 PUT = 6.69 CAD = 3.19 SPD = 3.93
[10]
Reversed-phase high-performance liquid chromatography
Ion-pair high-performance liquid chromatography
Spinach, Hazelnut, Banana, Potato and Chocolate
Kielbasa and sausage
HIS = 1.0.0 TRP = 4.5 PUT = 2.3 CAD = 1.4 SPD = 1.9 HIS = 8.0 TRP = 6.3 PUT = 7.0 CAD = 5.5 SPD = 5.8
[36]
CEME
TRP = 10.0 PUT = 10.0 CAD = 10.0 HIS = 20.0 SPD = 30.0 HIS = 16.7 TRP = 32.5 PUT = 61.3 CAD = 10.3 SPD = 13.2 TRP = 20.0 PUT = 10.0 CAD = 10.0 HIS = 10.0 SPD = 20.0 HIS = 0.0012 TRP = .0028 PUT = 0.0009 CAD = 0.0011 SPD = 0.0011 (ng) HIS = 20.0 TRP = 40.0 PUT = 10.0 CAD = 10.0 SPD = 20.0 HIS = 8.0 TRP = 6.0 PUT = 6.0 CAD = 6.0 SPD = 3.0
method. The method can be applied to preconcentration and determination of BAs in various food samples. In Table 3, a comparison of this method with some other reported methods for determination of BAs is presented. As this table illustrates, the proposed method is comparable with most previously reported methods from the standpoint of LODs and RSD values. Apart from the excellent cleanup that this method offers, the main advantage of the proposed method is the low required amount of sample and organic solvents. In conclusion, the followings are some good features of the developed method: No need to clean-up of extract, no need to solvent removal, low energy consumption, miniaturization of extraction setup, low samples size, using a few microlitter of the reagent, using very dilute acids, low waste and so on. Thus it could be considered as a green method for determination of BAs in food samples [36,37]. Acknowledgments This project was financially supported by Iran National Science Foundation (INSF) – grant number 95005963. The authors gratefully acknowledge the support of INSF and Tarbiat Modares University. Appendix A. Supplementary data Supplementary data associated with this article can be found, in the online version, at https://doi.org/10.1016/j.chroma.2018.04. 046. References [1] M.H. Silla Santos, Biogenic amines: their importance in foods, Int. J. Food Microbiol. 29 (1996) 213–231. [2] M.A. Awan, I. Fleet, C.L.P. Thomas, Determination of biogenic diamines with a vaporisation derivatisation approach using solid-phase microextraction gas chromatography–mass spectrometry, Food Chem. 111 (2008) 462–468.
TRP = 60.0 PUT = 30.0 CAD = 40.0 HIS = 10.0 SPD = 80.0 –
HIS = 50.0 TRP = 130.0 PUT = 30.0 CAD = 40.0 SPD = 70.0 HIS = 25.0 TRP = 15.0 PUT = 15.0 CAD = 15.0 SPD = 10.0
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Please cite this article in press as: F. Zarghampour, et al., Electromembrane extraction of biogenic amines in food samples by a microfluidic-chip system followed by dabsyl derivatization prior to high performance liquid chromatography analysis, J. Chromatogr. A (2018), https://doi.org/10.1016/j.chroma.2018.04.046