CN111426763A - High performance liquid chromatography tandem mass spectrometry method for detecting taxol in red-yolk duck eggs - Google Patents
High performance liquid chromatography tandem mass spectrometry method for detecting taxol in red-yolk duck eggs Download PDFInfo
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Abstract
The invention discloses a high performance liquid chromatography tandem mass spectrometry method for detecting taxol in red-heart duck eggs, which belongs to the technical field of analysis and detection.
Description
Technical Field
The invention belongs to the technical field of analysis and detection, and particularly relates to a high performance liquid chromatography tandem mass spectrometry determination method for taxol in red-yolk duck eggs.
Background
The yolk of the natural red-yolk duck egg is vermilion red, has stable and natural color and luster, and is popular with consumers in the market. The yellow pigment of common yolk mainly comprises yellow carotenoids such as lutein, zeaxanthin, neoxanthin, violaxanthin and the like, and the source of the yellow pigment is yellow carotenoids in grain type grains or green plants in feed. According to the related research, the egg-laying duck is a Chinese medicineNatural red-heart duck egg containing red carotenoid named as purpurin (Rhodoxanthin) and having molecular formula of C is produced by culturing or feeding fresh curly pondweed40H50O2The structural formula is shown in figure 1. Researches show that the taxol has the effects of resisting oxidation, eliminating free radicals, enhancing immunity, inhibiting tumor generation and the like on human bodies. Along with the improvement of living standard, the health care function of natural green food is more and more emphasized by people, so that the method has important significance for the research of the purple sweater purpurin in the natural red-yolk duck eggs. At present, no report is found about a method for detecting and quantifying the taxol in the natural red-yolk duck eggs.
Therefore, the development of an analysis and detection method capable of accurately quantifying the taxol in the red-yolk duck eggs is a problem which needs to be solved by the technical personnel in the field.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for accurately quantifying the taxol in red-yolk duck eggs, which is established by using high performance liquid chromatography-tandem mass spectrometry (L C-MS/MS), in order to solve the problems in the prior art.
In order to achieve the above purpose, the invention provides the following technical scheme:
the high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs comprises the following specific steps:
I. standard solution preparation
Accurately weighing and dissolving the taxol standard substance with a small amount of dichloromethane, then fixing the volume to scale with acetonitrile, preparing standard stock solution with the concentration of 100 mu g/m L, storing at-20 ℃, and diluting with acetonitrile into a series of standard working solutions with proper concentration according to specific conditions when in use;
II. Sample pretreatment
Accurately weighing a homogeneous sample in a centrifuge tube, adding an organic solvent and anhydrous sodium sulfate, uniformly mixing by vortex, carrying out ultrasonic extraction and centrifugal separation, transferring a supernatant into a rotary evaporation bottle, repeatedly extracting residues in the centrifuge tube with the organic solvent twice each time, combining organic solvent phases collected for three times, adding n-propanol, carrying out rotary evaporation concentration at 40 ℃ until the supernatant is dry, dissolving with 5m L organic solvent, transferring the residue into a 15m L centrifuge tube, adding 3m L n-hexane, carrying out vortex and centrifugal separation, removing an upper n-hexane phase, passing a lower organic solvent phase through a 0.22 mu m filter membrane, and carrying out on-machine analysis;
III, liquid chromatography conditions
Chromatographic column Shim-pack XR-ODS III (1.6 μm,2.0mm × 75mm) chromatographic column, column temperature 40 deg.C, sample size 5 μ L, mobile phase A of 5 mmol/L ammonium acetate or water, mobile phase B of acetonitrile, flow rate 0.3m L/min gradient elution procedure as in Table 1;
IV, Mass Spectrometry conditions
Electrospray ion source (ESI), positive ion mode scan, multiple reaction detection mode (MRM), air curtain gas (CUR)35.0 psi; collision gas pressure Medium, atomizer (GS1)55.0psi, auxiliary heater (GS2)50.0psi, ion source voltage (IS)5500V, auxiliary heater Temperature (TEM)600 ℃; other conditions are shown in table 2, where labeled fragment ions are quantitative ions.
TABLE 1
TABLE 2
Preferably, the organic solvent in step II includes dichloromethane, acetonitrile and acetone.
Further preferably, the organic solvent in step II is acetonitrile.
Most preferably, the concrete parameters of the sample pretreatment in the step II are that 5.0g (accurate to 0.01g) of a homogeneous sample is accurately weighed in a 50m L centrifuge tube, 20m L acetonitrile and 5g anhydrous sodium sulfate are added, the mixture is uniformly mixed by vortex for 1min, ultrasonic extraction is carried out for 15min, then centrifugation is carried out for 5min at 4000r/min, supernatant is transferred to a 100m L rotary evaporation bottle, extraction is carried out on residues in the centrifuge tube by 20m L acetonitrile twice each time, acetonitrile phases collected for three times are combined, 5m L n-propanol is added, rotary evaporation concentration is carried out at 40 ℃ until the mixture is dry, the mixture is dissolved by 5m L acetonitrile and transferred to a 15m L centrifuge tube, 3m L n-hexane is added, vortex is carried out for 1min, centrifugation is carried out for 5min at 4000r/min, an upper layer of the n-hexane phase is discarded, and a lower layer of the acetonitrile phase passes through a.
Further, for convenience of solid-liquid separation, the specific step of the centrifugation treatment in the step II is 8000 rmp centrifugation for 20 min.
Preferably, the mobile phase in step III is 5 mmol/L ammonium acetate-acetonitrile.
Compared with the prior art, the invention establishes the high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs, and has the following excellent effects:
extracting a sample with acetonitrile, concentrating by rotary evaporation, degreasing with n-hexane, and measuring by a machine. The result shows that the method is simple to operate, high in sensitivity and good in accuracy, provides a method reference for determining the taxol in the red-yolk duck eggs, and has great application potential and economic value in the fields of red-yolk duck egg processing production, quality grading and the like.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the provided drawings without creative efforts.
FIG. 1 shows the chemical structural formula of the target taxol of the present invention.
FIG. 2 is a first order mass spectrum of the subject of the invention, taxol.
FIG. 3 is a second-order mass spectrum of the purple sweater purple pigment of the present invention.
FIG. 4 is a multi-reaction monitoring (MRM) chromatogram of a standard substance of a target taxol of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention discloses a high performance liquid chromatography tandem mass spectrometry method for detecting taxol in red-yolk duck eggs. Extracting the sample with acetonitrile, concentrating by rotary evaporation, degreasing with n-hexane, and measuring by a machine. The result shows that the method is simple to operate, high in sensitivity and good in accuracy, provides a method reference for determining the taxol in the red-yolk duck eggs, and has great application potential and economic value in the fields of red-yolk duck egg processing production, quality grading and the like.
The present invention will be further specifically illustrated by the following examples for better understanding, but the present invention is not to be construed as being limited thereto, and certain insubstantial modifications and adaptations of the invention by those skilled in the art based on the foregoing disclosure are intended to be included within the scope of the invention.
Example 1
The high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs comprises the following specific steps:
I. standard solution preparation
Accurately weighing 10mg of the taxol standard substance, respectively placing the taxol standard substance into 100m L volumetric flasks, dissolving with a small amount of dichloromethane, then fixing the volume to scale with acetonitrile, preparing standard stock solution with the concentration of 100 mu g/m L, storing at-20 ℃, and diluting with acetonitrile into a series of standard working solutions with proper concentration according to specific conditions when in use;
II. Sample pretreatment
Accurately weighing 5.0g (accurate to 0.01g) of a homogeneous sample in a 50m L centrifuge tube, adding 20m L acetonitrile and 5g anhydrous sodium sulfate, uniformly mixing by vortex for 1min, carrying out ultrasonic extraction for 15min, centrifuging for 5min at 4000r/min, transferring a supernatant into a 100m L rotary evaporation bottle, repeatedly extracting residues in the centrifuge tube with 20m L acetonitrile twice each time, combining acetonitrile phases collected for three times, adding 5m L n-propanol, carrying out rotary evaporation concentration at 40 ℃ until the residues are dry, dissolving with 5m L acetonitrile, transferring the dissolved residues into a 15m L centrifuge tube, adding 3m L n-hexane, carrying out vortex for 1min, centrifuging for 5min at 4000r/min, discarding an upper n-hexane phase, passing a lower acetonitrile phase through a 0.22 mu m filter membrane, and carrying out on-machine analysis;
III, liquid chromatography conditions
The chromatographic column is a Shim-pack XR-ODS III (1.6 μm,2.0mm × 75mm) chromatographic column, the column temperature is 40 ℃, the sample injection amount is 5 μ L, the mobile phase A is 5 mmol/L ammonium acetate, the mobile phase B is acetonitrile, and the flow rate is 0.3m L/min;
IV, Mass Spectrometry conditions
Electrospray ion source (ESI), positive ion mode scan, multiple reaction detection mode (MRM), air curtain gas (CUR)35.0 psi; collision gas pressure Medium, atomizer (GS1)55.0psi, auxiliary heater (GS2)50.0psi, ion source voltage (IS)5500V, auxiliary heater Temperature (TEM)600 ℃; other conditions are shown in Table 2.
TABLE 1
TABLE 2
Note: wherein the labeled fragment ions are quantitative ions.
Example 2
The high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs is the same as the embodiment 1, and the difference is only that the acetonitrile in the step II is replaced by dichloromethane.
Example 3
The high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs is the same as the embodiment 1, and the difference is only that the acetonitrile in the step II is replaced by acetone.
Example 4
The high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-heart duck eggs is the same as the embodiment 1, and the difference is only that the mobile phase 5 mmol/L ammonium acetate-acetonitrile in the step III is replaced by an acetonitrile-water system.
Examples 5 to 14
The method for measuring the purple swainsonine in the red-yolk duck eggs by high performance liquid chromatography-tandem mass spectrometry is the same as that in example 1, and is different from the method for measuring the purple swainsonine in the red-yolk duck eggs by collecting 10 red-yolk duck egg samples of different types. The 10 red-yolk duck egg samples are all taken from red-yolk sea duck eggs in the northern sea of Guangxi, urban defense, Qinzhou and other areas, the content of the taxol in the samples is shown in table 3, and the results show that the analysis and detection method provided by the invention is simple to operate and good in accuracy, and has great application potential and economic value in the fields of red-yolk duck egg processing production, quality grading and the like.
TABLE 3
Note: "ND" is not detected.
To further verify the excellent effects of the present invention, the inventors also conducted the following comparative experiments:
comparative example 1
The high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs is the same as the embodiment 1, and the difference is only that the acetonitrile in the step II is replaced by the methanol.
Comparative example 2
The high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs is the same as the embodiment 1, and the difference is only that the acetonitrile in the step II is replaced by petroleum ether.
Comparative example 3
The method for measuring the high performance liquid chromatography-tandem mass spectrometry of the taxol in the red-heart duck eggs is the same as the embodiment 1, and the difference is only that the mobile phase 5 mmol/L ammonium acetate-acetonitrile in the step III is replaced by a methanol-water system.
In order to further prove the beneficial effects of the present invention and to better understand the present invention, the following determination tests further illustrate the properties and application performance of the method for measuring the high performance liquid chromatography tandem mass spectrometry of the taxol in the red-yolk duck eggs, but the method is not to be construed as limiting the present invention, and the method properties obtained by other determination tests and the application based on the above properties, which are performed by the person skilled in the art according to the above summary of the invention, are also considered to fall within the protection scope of the present invention
Experimental example 1
Selection of Mass Spectrometry conditions
Continuously injecting 200ng/M L single standard solution into a mass spectrometer by a flow injection pump, performing primary mass spectrum full scan in a positive mode, and determining parent ions, wherein the relative molecular mass of the taxol is 562.84, so the mass spectrum scanning range is set to M/z 510-610 to eliminate impurity interference and improve sensitivity, and a primary mass spectrogram of the taxol is shown in figure 2]+Peak sum [ M + Na]+Peak, but [ M + Na]+The peak is easy to interfere with the system pipeline, mobile phase and sample matrix and is not stable enough, so that stable [ M + H ] is selected]+Peak(s). And (3) applying certain collision energy to the parent ions to perform secondary mass spectrum scanning, wherein a secondary mass spectrum chart is shown in figure 3, m/z282, m/z265, m/z284 and m/z246 are main ion fragment peaks, two fragment ions with high abundance and less interference are selected as quantitative and qualitative ions, and mass spectrum parameters such as collision energy, declustering voltage, collision chamber inlet voltage, collision cell voltage and the like are optimized. The Multiple Reaction Monitoring (MRM) chromatogram of the purple sweater purple pigment standard is shown in FIG. 4.
Experimental example 2
Selection of chromatographic conditions
Comparing the separation effects of examples 1, 4 and 3, it can be seen that the taxol belongs to a weak polar compound and is easily retained by a reversed phase chromatographic column, and the separation effect is examined on a Shim-pack XR-ODS III (1.6 μm,2.0mm × 75mm) by using a methanol-water (comparative example 3) and an acetonitrile-water system (example 4) as mobile phases, and the result shows that example 4 using an acetonitrile-water body as a mobile phase can obtain a higher signal response value, but the chromatographic peak has a tailing phenomenon due to the secondary retention effect, and therefore, 5 mmol/L of ammonium acetate is added to the aqueous phase as a modifier and the ionization efficiency is improved at the same time, and the result shows that the chromatographic peak profile of example 1 is significantly improved and the signal response value is also improved, so 5 mmol/L of ammonium-acetonitrile is selected as the mobile phase.
Experimental example 3
Selection of extraction conditions
Carotenoids are soluble in most organic solvents and insoluble in water. The extraction efficiency results of the taxol are compared with the extraction efficiency results of the taxol in the comparative examples 1-3 and the comparative examples 1-2 by using dichloromethane, methanol, petroleum ether, acetonitrile and acetone as organic solvents. It can be seen that dichloromethane, acetonitrile and acetone all have ideal extraction efficiency. Considering that dichloromethane has high toxicity and is easily harmful to experimenters in the experimental process, the dichloromethane is not suitable for use. Compared with acetone, acetonitrile has the characteristics of denaturing protein and reducing fat entering into an extracting solution, and is beneficial to subsequent on-machine analysis, so that acetonitrile is selected as the most preferable extracting solvent.
Experimental example 4
Linear dependence and detection limit of detection method
Standard working solutions with the weight concentrations of the taxol of 5.0ng/m L, 10.0ng/m L, 20.0ng/m L, 50ng/m L and 100ng/m L are prepared respectively, and are measured under the chromatographic conditions of example 1, the sample amount is 5 mu L, the concentration (ng/m L) is used as an abscissa (x), and the peak area is used as an ordinate (y) for plotting to draw a standard curve, the weight concentration of the standard solution added into the sample is gradually reduced, and when the signal to noise ratio (S/N) of the compound is 3, the weight concentration is defined as the method detection limit (L OD), and the linear equation of the compound, the correlation coefficient and the detection limit result are shown in Table 4.
TABLE 4
Experimental example 5
Standard recovery rate and precision of detection method
Negative duck egg samples were selected, and 3 concentration levels of standard mixed solution were added, and pre-treated as described in example 1, with 6 replicates per standard level. As can be seen from Table 5, the recovery rates of the 3 spiked samples with different concentration levels are between 86.7% and 94.5%, and the relative standard deviation is between 1.62% and 3.45, which indicates that the recovery rate of the invention is good and the precision is high.
TABLE 5
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (5)
1. The high performance liquid chromatography tandem mass spectrometry method for the taxol in the red-yolk duck eggs is characterized by comprising the following specific steps:
I. standard solution preparation
Accurately weighing and dissolving the taxol standard substance with a small amount of dichloromethane, then fixing the volume to scale with acetonitrile, preparing standard stock solution with the concentration of 100 mu g/m L, storing at-20 ℃, and diluting with acetonitrile into a series of standard working solutions with proper concentration according to specific conditions when in use;
II. Sample pretreatment
Accurately weighing a homogeneous sample in a centrifuge tube, adding an organic solvent and anhydrous sodium sulfate, uniformly mixing by vortex, carrying out ultrasonic extraction and centrifugal separation, transferring a supernatant into a rotary evaporation bottle, repeatedly extracting residues in the centrifuge tube twice by using the organic solvent, combining organic solvent phases collected for three times, adding n-propanol, carrying out rotary evaporation concentration at 40 ℃ until the supernatant is dry, dissolving by using a 5m L organic solvent, transferring into a 15m L centrifuge tube, adding 3m L n-hexane, carrying out vortex and centrifugal separation, removing an upper n-hexane phase, and carrying out on-machine analysis after a lower organic solvent phase passes through a 0.22 mu m filter membrane;
III, liquid chromatography conditions
Chromatographic column Shim-packXR-ODSIII (1.6 μm,2.0mm × 75mm) chromatographic column, column temperature 40 deg.C, sample size 5 μ L, mobile phase A of 5 mmol/L ammonium acetate or water, mobile phase B of acetonitrile, flow rate 0.3m L/min gradient elution procedure as in Table 1;
IV, Mass Spectrometry conditions
Electrospray ion source (ESI), positive ion mode scan, multiple reaction detection mode (MRM), air curtain gas (CUR)35.0 psi; collision gas pressure Medium, atomizer (GS1)55.0psi, auxiliary heater (GS2)50.0psi, ion source voltage (IS)5500V, auxiliary heater Temperature (TEM)600 ℃; other conditions are shown in table 2, where labeled fragment ions are quantitative ions.
TABLE 1
TABLE 2
2. The method for measuring the purple swainsonine in red-yolk duck eggs according to claim 1, wherein the organic solvent in the step II comprises dichloromethane, acetonitrile and acetone.
3. The method for measuring the purple swainsonine in the red-yolk duck eggs according to claim 2, wherein the organic solvent in the step II is acetonitrile.
4. The HPLC-MS/MS method for detecting violaxanthin in red-yolk duck eggs as claimed in claim 3, wherein the pre-treatment of the sample in step II comprises accurately weighing 5.0g (accurate to 0.01g) of the homogeneous sample in a 50m L centrifuge tube, adding 20m L acetonitrile and 5g anhydrous sodium sulfate, mixing by vortexing for 1min, performing ultrasonic extraction for 15min, centrifuging at 4000r/min for 5min, transferring the supernatant to a 100m L rotary evaporation bottle, extracting the residue in the centrifuge tube with 20m L acetonitrile twice, combining the collected acetonitrile phases obtained in three times, adding 5m L n-propanol, performing rotary evaporation and concentration at 40 ℃ to dryness, dissolving with 5m L acetonitrile and transferring to a 15m L centrifuge tube, adding 3m L n-hexane, vortexing for 1min, centrifuging at 4000r/min for 5min, discarding the upper n-hexane phase, passing the lower acetonitrile phase through a 0.22 μm filter membrane, and performing mechanical analysis.
5. The method for measuring the purple swainsonine in red-yolk duck eggs according to claim 1, wherein the mobile phase in the step III is 5 mmol/L ammonium acetate-acetonitrile.
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| CN113373077A (en) * | 2021-02-07 | 2021-09-10 | 南宁海关技术中心 | High-efficiency chloramphenicol degrading bacterium, high-efficiency degrading microbial inoculum and application thereof |
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| JPH08198789A (en) * | 1995-01-27 | 1996-08-06 | Res Inst For Prod Dev | Extract containing carotenoid having antioxidant activity, its production and antioxidant and colorant |
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| CN113373077A (en) * | 2021-02-07 | 2021-09-10 | 南宁海关技术中心 | High-efficiency chloramphenicol degrading bacterium, high-efficiency degrading microbial inoculum and application thereof |
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