CN109596696B - Liquid/liquid interface electrochemical detection method for traditional Chinese medicine component emodin - Google Patents
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Abstract
The invention provides a liquid/liquid interface electrochemical detection method of traditional Chinese medicine component emodin, which is characterized in that a four-electrode electrolysis device is adopted, a polyvinylidene fluoride membrane is used for modifying a water/1, 6-dichlorohexane interface, and the content of the emodin in a sample is quantitatively detected by a differential pulse voltammetry method. The method is characterized in that a polyvinylidene fluoride membrane is used for modifying a water/1, 6-dichlorohexane interface, and a differential pulse voltammetry is adopted to draw a standard curve of peak current and emodin concentration generated when emodin is transferred on the water/1, 6-dichlorohexane interface. The traditional Chinese medicines of the root of giant knotweed, the rumex madaio (root, stem and leaf), the aloe plant and the aloe beverage are extracted and centrifugally separated for pretreatment, the differential pulse voltammetry is used for detecting emodin in the extract of the root of giant knotweed, the rumex madaio (root, stem and leaf) and the aloe leaf and the aloe beverage, and the emodin content in the sample is obtained according to the drawn standard curve. The invention provides a simple and rapid method for electrochemically detecting emodin.
Description
Technical Field
The invention relates to a method for detecting emodin as a traditional Chinese medicine component by modifying a water/1, 6-dichlorohexane interface by a polyvinylidene fluoride membrane and adopting a liquid/liquid interface electrochemical method, belonging to the field of electrochemical detection.
Background
Currently, the most common methods for the analytical detection of emodin are chromatography, mass spectrometry and spectrometry, such as high performance liquid chromatography. However, no report has been found on the study of emodin by a liquid/liquid interfacial electrochemical method.
The liquid/liquid interface, also known as the interface of two immiscible electrolyte solutions or the oil/water interface, is an important branch of electrochemistry and electroanalytical chemistry due to its wide application prospects in the fields of analysis and detection of ions, extraction separation, simulation of biological membranes and chemical sensors. In recent years, the application of liquid/liquid interface electrochemistry to the analysis and detection of drug ions has attracted attention, wherein the membrane modifies the micro-and nano-liquid/liquid interface of the array obtained by the liquid/liquid interface, and also attracts great attention due to the characteristics of the porous membrane material in structure and performance. However, the polyvinylidene fluoride membrane modification liquid/liquid interface applied to ion analysis and detection is not found at present, and the liquid/liquid interface electrochemical method applied to emodin detection is not reported.
Disclosure of Invention
The invention aims to provide a simple and rapid method for detecting emodin in medicines and foods.
In order to achieve the purpose, the invention adopts a polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface electrochemical method to detect the content of the emodin in the medicines and the foods.
The specific technical scheme of the invention is as follows:
a liquid/liquid interface electrochemical detection method for emodin serving as a traditional Chinese medicine component is characterized in that a four-electrode electrolysis device is adopted, a polyvinylidene fluoride membrane is used for modifying a water/1, 6-dichlorohexane interface, and the content of the emodin in a sample is quantitatively detected by a differential pulse voltammetry method.
Preferably, the four-electrode electrolysis device comprises an electrolysis bath body for containing an oil phase solution and a glass tube for containing an aqueous phase solution, wherein the oil phase solution is 1, 6-dichlorohexane containing bis (triphenylphosphine) ammonium tetrakis (4-chlorophenyl) borate, a first branch tube and a second branch tube are arranged on the side wall of the electrolysis bath body, a first counter electrode and a first reference electrode are arranged in the glass tube, a second counter electrode and a second reference electrode are respectively arranged in the first branch tube and the second branch tube, the first branch tube is communicated with the inside of the electrolysis bath body, the second branch tube is communicated with the inside of the electrolysis bath body, and the oil phase reference is arranged in the second branch tube; and adhering a polyvinylidene fluoride membrane to the lower port of the glass tube to enable the polyvinylidene fluoride membrane to completely cover the lower port, and forming a polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface when the lower port of the glass tube is contacted with the oil phase solution in the electrolytic bath body.
Preferably, the differential pulse voltammetry comprises:
step 1: respectively injecting emodin standard solutions with different concentrations into a glass tube, contacting a lower port of the glass tube with an oil phase solution in an electrolytic cell body, and measuring a differential pulse voltammetry curve of the emodin standard solutions with different concentrations by adopting a CHI660D type electrochemical workstation to obtain a standard curve and a linear fitting equation of the emodin concentration and the peak current of the differential pulse voltammetry curve, wherein the parameters of the differential pulse voltammetry are set as follows: the scanning speed is 10-20 mV/s, and the pulse amplitude is 30-50 mV;
step 2: directly taking a sample to be detected, filtering and collecting supernatant; or placing the sample to be tested in distilled water, performing oil bath at 90 ℃, filtering, and collecting the supernatant; or grinding the sample to be detected into juice by using a mortar; filtering and collecting supernatant;
and step 3: and (3) injecting the obtained supernatant into a glass tube, contacting a lower port of the glass tube with an oil phase solution in the electrolytic cell body, and measuring a differential pulse voltammetry curve by using a CHI660D electrochemical workstation, wherein the parameters of the differential pulse voltammetry are set as follows: the scanning speed is 10-20 mV/s, the pulse amplitude is 30-50 mV, and the content of the emodin in the sample is determined through a linear fitting equation.
Preferably, the liquid/liquid interface electrochemical detection method for emodin as a traditional Chinese medicine component further comprises the anti-interference performance measurement of emodin detection, and comprises the following steps: the influence of the CHI660D electrochemical workstation on the detection of emodin by the interferent is measured by cyclic voltammetry, wherein the parameters of the cyclic voltammetry are set as follows: the scanning speed is 10-20 mV/s.
More preferably, the interferent is at least one of D-glucose, D-sucrose, urea, L-lysine, potassium chloride and sodium sulfate.
Preferably, the sample is at least one of giant knotweed rhizome, rhubarb root, stem, leaf, aloe leaf and aloe beverage.
Compared with the prior art, the invention has the beneficial effects that:
the invention applies differential pulse voltammetry to analyze and detect emodin on a polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface. The method for electrochemically detecting the emodin by the polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface has the characteristics of simplicity, convenience and quickness. And the detection sensitivity of emodin ions is 1.762 muA/mM, and the detection limit is 54.6 muM. The anti-interference experiment result of emodin shows that the effect of the interferents on the transfer of emodin ions is-3.5% -9.5% (less than +/-10%), so that the interferents have no effect on the detection of the emodin ions. In conclusion, the differential pulse voltammetry method can be used for quickly and accurately detecting emodin in extracts of polygonum cuspidatum roots, rheum officinale (roots, stems and leaves) and aloe leaves and aloe drinks on a polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface, and has the characteristics of simplicity, convenience and quickness.
Drawings
FIG. 1 shows differential pulse voltammetry curves obtained from different concentrations of emodin solutions (0.1-0.5 mM).
FIG. 2 is a standard curve of peak current of emodin ion transfer from oil phase to water phase and emodin concentration in water solution.
Formula (1) is a linear fitting equation of peak current (I) and emodin concentration (C) based on a differential pulse voltammetry standard curve.
FIG. 3 is a graph of transfer cyclic voltammograms of emodin in the presence of the interferent D-glucose;
FIG. 4 is a transfer cyclic voltammogram of emodin in the presence of the interferent D-sucrose;
FIG. 5, transfer cyclic voltammograms of emodin in the presence of the interferent urea;
FIG. 6 is a graph of transfer cyclic voltammograms of emodin in the presence of the interferent L-lysine;
FIG. 7, transfer cyclic voltammogram of emodin in the presence of the interferent potassium chloride;
FIG. 8, transfer cyclic voltammogram of emodin in the presence of the interferent sodium sulfate;
FIG. 9 is a graph of differential pulse voltammetry of a solution of Polygonum cuspidatum;
FIG. 10, a photograph of a slice of Polygonum cuspidatum root;
FIG. 11 shows the solution obtained after cutting the root of Polygonum cuspidatum;
FIG. 12 is a differential pulse voltammogram of Rumex madaio root solution;
FIG. 13 is a photograph of a whole rhubarb;
FIG. 14 shows the solution obtained after rhaponticum uniflorum root treatment;
FIG. 15 is a differential pulse voltammogram of Rumex madaio leaf solution;
FIG. 16 shows the solution obtained after the leaves of Rheum officinale are treated;
FIG. 17 is a differential pulse voltammogram of Rumex madaio petiole solution;
FIG. 18 shows the solution obtained after the Rheum officinale petiole treatment;
FIG. 19 is a graph of differential pulse voltammetry of aloe leaf solution;
FIG. 20, a picture of an aloe plant;
FIG. 21, solution obtained after aloe leaf treatment;
FIG. 22, differential pulse voltammogram of an aloe beverage solution;
FIG. 23 is a photograph of a bottle of aloe vera beverage;
FIG. 24, solution obtained after aloe drink treatment;
FIG. 25 is a schematic view of a four-electrode electrolyzer.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Examples
A liquid/liquid interface electrochemical detection method for emodin as a traditional Chinese medicine component adopts a four-electrode electrolysis device, utilizes a polyvinylidene fluoride membrane to modify a water/1, 6-dichlorohexane interface, and quantitatively detects the content of emodin in a sample by a differential pulse voltammetry method. Wherein the polyvinylidene fluoride membrane (Shanghai Movix scientific instruments Co., Ltd.) preferably has a membrane diameter of 47 mm. The specific detection steps are as follows:
1. as shown in FIG. 25, the four-electrode electrolyzer of the invention comprises an electrolyzer body 1 for containing an oil phase solution and a glass tube 2 for containing an aqueous phase solution, wherein a first branch tube 3 and a second branch tube 4 are arranged on the side wall of the electrolyzer body 1, a first pair of electrodes 5 and a first reference electrode 6 are arranged in the glass tube 2, a second pair of electrodes 7 and a second reference electrode 8 are respectively arranged in the first branch tube 3 and the second branch tube 4, the first branch tube 3 is communicated with the inside of the electrolyzer body 1, the second branch tube 4 is communicated with the inside of the electrolyzer body 1, and an oil phase reference is arranged in the second branch tube 4.
Taking a polyvinylidene fluoride membrane (with the diameter of 9mM, the aperture of which is 200nm), adhering the polyvinylidene fluoride membrane to the lower port of a glass tube (with the inner diameter of 6mM and the outer diameter of 9mM) by using silica gel (Dow Corning organic silica gel), enabling the polyvinylidene fluoride membrane to completely cover the lower port, standing at room temperature for 10-12h, injecting 1 ml of 10mM sodium chloride aqueous solution into the glass tube after the silica gel is solidified, when the lower port of the glass tube was brought into contact with an oily phase solution of 1, 6-dichlorohexane containing 20mM of ammonium bis (triphenylphosphine) tetrakis (4-chlorophenyl) borate in the electrolytic bath body 1, forming a polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface, wherein oil phase references are 10mM sodium chloride and 1mM bis- (triphenylphosphine) ammonium chloride aqueous solution, the first Counter Electrode (CE)5 and the second counter electrode 7 are both platinum wire electrodes, and the first Reference Electrode (RE)6 and the second reference electrode 8 are Ag/AgCl electrodes.
2. Adding 1 ml of standard aqueous solution of emodin with different concentrations (final concentration 0.1-0.5 mM, pH 10.0) into a glass tube 2 containing 1 ml of 10mM sodium chloride aqueous solution of the four-electrode electrolysis device in the step 1, injecting the glass tube into the lower port of the glass tube, contacting the lower port of the glass tube with the oil phase solution in the electrolysis bath body, and measuring differential pulse voltammetry curves of the standard solution of the emodin with different concentrations by using a CHI660D type electrochemical workstation (Shanghai Chenghua instruments, Inc.), wherein the parameters of the differential pulse voltammetry are set as follows: the scanning speed is 10-20 mV/s, and the pulse amplitude is 30-50 mV. As can be seen from fig. 1, the transfer peak potential of emodin ions at the interface of the polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane is 0.052V, and the peak current of the differential pulse voltammetry curve for emodin ion transfer increases with the increase of emodin concentration, and both of them show good linear relationship, so as to obtain a linear fitting standard curve and a fitting equation (1) for the transfer peak current of the differential pulse voltammetry curve for emodin concentration and emodin ions, as shown in fig. 2. And the detection sensitivity of emodin ions is 1.762 muA/mM, and the detection limit is 54.6 muM.
3. Anti-interference performance of emodin detection
1 ml of emodin aqueous solution, 1 ml of emodin and interferon mixed aqueous solution are respectively added into a glass tube 2 containing 1 ml of 10mM sodium chloride aqueous solution of the four-electrode electrolysis device in the step 1, and the CHI660D type electrochemical workstation is adopted to utilize cyclic voltammetry to detect different interferons (5mM) including D-glucose, D-sucrose, urea, L-lysine, potassium chloride and sodium sulfate on emodin (0.3 mM). Wherein, the parameters of the cyclic voltammetry are set as follows: the scanning speed is 10-20 mV/s.
The curves in FIG. 3 are the transfer cyclic voltammograms with 0.3mM emodin alone (solid line), 0.3mM emodin and 5mM D-glucose (dashed line), respectively. From the measured peak current values, a relative error value of-3.5% (less than. + -. 10%) for D-glucose for emodin ion at the polyvinylidene fluoride membrane-modified water/1, 6-dichlorohexane interface was obtained.
The curves in FIG. 4 are the transfer cyclic voltammograms with 0.3mM emodin alone (solid line), 0.3mM emodin and 5mM D-sucrose (dashed line), respectively. From the measured peak current values, a relative error value of-3.7% (less than. + -. 10%) for D-sucrose for emodin ions at the polyvinylidene fluoride membrane-modified water/1, 6-dichlorohexane interface was obtained.
The curves in FIG. 5 are the transfer cyclic voltammograms with 0.3mM emodin alone (solid line), 0.3mM emodin and 5mM urea (dashed line), respectively. From the measured peak current values, a relative error value of-6.3% (less than. + -. 10%) for urea to emodin ions at the polyvinylidene fluoride membrane-modified water/1, 6-dichlorohexane interface was obtained.
The curves in FIG. 6 are the transfer cyclic voltammograms with 0.3mM emodin alone (solid line), 0.3mM emodin and 5mM L-lysine (dashed line), respectively. From the measured peak current values, a relative error value of-8.5% (less than. + -. 10%) of L-lysine for emodin ion at the polyvinylidene fluoride membrane-modified water/1, 6-dichlorohexane interface was obtained.
The curves in FIG. 7 are the transfer cyclic voltammograms with 0.3mM emodin alone (solid line), 0.3mM emodin and 5mM potassium chloride (dashed line), respectively. From the measured peak current values, a relative error value of-9.5% (less than. + -. 10%) for potassium chloride for emodin ions at the polyvinylidene fluoride membrane-modified water/1, 6-dichlorohexane interface was obtained.
The curves in FIG. 8 are the transfer cyclic voltammograms with 0.3mM emodin alone (solid line), 0.3mM emodin and 5mM sodium sulfate (dashed line), respectively. From the measured peak current values, a relative error value of-7.4% (less than. + -. 10%) for sodium sulfate to emodin ion at the polyvinylidene fluoride membrane-modified water/1, 6-dichlorohexane interface was obtained.
The results show that the relative error value of the interferent on the emodin ions on the polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface is between-3.5% and-9.5% (less than +/-10%), so the interferent has no influence on the detection of the emodin ions.
4. Sequentially placing rhizoma Polygoni Cuspidati (23.50g), radix Rumicis Crispi leaf (21.30g) and radix Rumicis Crispi petiole (22.20g) in distilled water, and oil-bathing at 90 deg.C for 1 h. Fresh aloe leaf (10.50g) was ground into a juice in a mortar. 50ml of aloe juice beverage is also taken. The samples were filtered sequentially through GL-20-II high speed refrigerated centrifuge (Shanghai' an Tint scientific Instrument factory, 8000r/min, 10min) and the supernatant was collected. Rhizoma Polygoni Cuspidati, radix Rumicis Japonici, and Aloe respectively as shown in figures 10, 13, and 20, the supernatant is shown in figures 11, 14, 16, 18, and 21, and the Aloe juice beverage is shown in figure 23.
5. And (3) taking 1 ml of the clear liquid obtained in the step (4), injecting the clear liquid into a glass tube which is provided with the four-electrode electrolytic device and contains 1 ml of 10mM sodium chloride aqueous solution and is arranged in the step (1), then contacting the lower port of the glass tube with the oil phase solution in the electrolytic cell body through a lifting device, and sequentially measuring the differential pulse voltammetry curve of the sample in the step (4) by adopting a CHI660D type electrochemical workstation, wherein the oil phase solution and the oil phase reference are the same as those in the step (2). The parameters of the differential pulse voltammetry are set as follows: the scanning speed is 10-20 mV/s, the pulse amplitude is 30-50 mV, and the content of the emodin in the sample is determined through a linear fitting equation.
As can be seen from FIG. 9, the peak current of the differential pulse voltammogram of emodin ions in Polygonum cuspidatum was 2.903 μ A, although the peak current was clearly observed in the graph. Can be substituted into the formula (1) to obtain the emodin with the concentration of 0.482mM, so that the emodin content in the root of the giant knotweed rhizome is 0.277 mg/g.
As can be seen from FIG. 12, the peak current of the differential pulse voltammogram of emodin ions in Rheum emodi root is 2.623 μ A, since the peak current is clearly seen in the graph. The emodin is substituted into the formula (1) to obtain the emodin with the concentration of 0.323mM, so that the content of the rhaponticum emodin at the root part is 0.186 mg/g.
As can be seen from fig. 19, the peak current change is clearly seen in the transfer peak potential of the differential pulse voltammogram of emodin ions in aloe plants. According to the graph, the peak current of the differential pulse voltammogram is 1.978 μ A. Can be substituted into the formula (1) to obtain the product, wherein the concentration of emodin is 0.180mM, so that the content of emodin in aloe is 0.103 mg/g.
As can be seen from fig. 22, the change in peak current was clearly seen in the transition peak potential of the differential pulse voltammogram of emodin ions in aloe beverages. According to the figure, the peak current of the differential pulse voltammogram is 1.297 μ A. Can be substituted by the formula (1), and the concentration of the emodin in the aloe beverage is 0.049mM, so that the content of the emodin in the aloe beverage is 0.013mg/ml.
On the other hand, no change in peak current was observed in the transferred peak potentials of the differential pulse voltammograms of Rheum officinale leaf (FIG. 15) and Rheum officinale petiole (FIG. 17), and therefore no emodin was detected in Rheum officinale leaf and petiole.
Claims (4)
1. A liquid/liquid interface electrochemical detection method of traditional Chinese medicine component emodin is characterized in that a four-electrode electrolysis device is adopted, a polyvinylidene fluoride membrane is utilized to modify a water/1, 6-dichlorohexane interface, and the content of the emodin in a sample is quantitatively detected by a differential pulse voltammetry method; the four-electrode electrolytic device comprises an electrolytic tank body for containing an oil phase solution and a glass tube for containing a water phase solution, wherein the oil phase solution is 1, 6-dichlorohexane containing bis (triphenylphosphine) ammonium tetrakis (4-chlorophenyl) borate, a first branch tube and a second branch tube are arranged on the side wall of the electrolytic tank body, a first pair of electrodes and a first reference electrode are arranged in the glass tube, a second pair of electrodes and a second reference electrode are respectively arranged in the first branch tube and the second branch tube, the first branch tube is communicated with the inside of the electrolytic tank body, the second branch tube is communicated with the inside of the electrolytic tank body, and the oil phase reference is arranged in the second branch tube; adhering a polyvinylidene fluoride membrane to the lower port of the glass tube to enable the polyvinylidene fluoride membrane to completely cover the lower port, and forming a polyvinylidene fluoride membrane modified water/1, 6-dichlorohexane interface when the lower port of the glass tube is contacted with the oil phase solution in the electrolytic bath body; the differential pulse voltammetry comprises the following steps:
step 1: respectively injecting emodin standard solutions with different concentrations into a glass tube, contacting a lower port of the glass tube with an oil phase solution in an electrolytic cell body, and measuring a differential pulse voltammetry curve of the emodin standard solutions with different concentrations by adopting a CHI660D type electrochemical workstation to obtain a standard curve and a linear fitting equation of the emodin concentration and the peak current of the differential pulse voltammetry curve, wherein the parameters of the differential pulse voltammetry are set as follows: the scanning speed is 10-20 mV/s, and the pulse amplitude is 30-50 mV;
step 2: directly taking a sample to be detected, filtering and collecting supernatant; or placing the sample to be tested in distilled water, performing oil bath at 90 ℃, filtering, and collecting the supernatant; or grinding the sample to be detected into juice by using a mortar; filtering and collecting supernatant;
and step 3: and (3) injecting the obtained supernatant into a glass tube, contacting a lower port of the glass tube with an oil phase solution in the electrolytic cell body, and measuring a differential pulse voltammetry curve by using a CHI660D electrochemical workstation, wherein the parameters of the differential pulse voltammetry are set as follows: the scanning speed is 10-20 mV/s, the pulse amplitude is 30-50 mV, and the content of the emodin in the sample is determined through a linear fitting equation.
2. The liquid/liquid interface electrochemical detection method of emodin as a traditional Chinese medicine component of claim 1, further comprising the anti-interference performance measurement of emodin detection, comprising: the influence of the CHI660D electrochemical workstation on the detection of emodin by the interferent is measured by cyclic voltammetry, wherein the parameters of the cyclic voltammetry are set as follows: the scanning speed is 10-20 mV/s.
3. The method for electrochemical detection of liquid/liquid interface of emodin as Chinese medicinal ingredient of claim 2, wherein the interferent is at least one of D-glucose, D-sucrose, urea, L-lysine, potassium chloride or sodium sulfate.
4. The method of claim 1, wherein the sample is at least one of rhizoma Polygoni Cuspidati, radix Rumicis Crispi, stem, leaf, folium Aloe or Aloe beverage.
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