CN112964819A - Method for detecting dianthrone compounds in polygonum multiflorum - Google Patents
Method for detecting dianthrone compounds in polygonum multiflorum Download PDFInfo
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- CN112964819A CN112964819A CN202110162749.6A CN202110162749A CN112964819A CN 112964819 A CN112964819 A CN 112964819A CN 202110162749 A CN202110162749 A CN 202110162749A CN 112964819 A CN112964819 A CN 112964819A
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- dianthrone
- polygonum multiflorum
- polygonumnolide
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Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds
Abstract
The invention provides a method for detecting dianthrone compounds in polygonum multiflorum, and belongs to the technical field of chemical analysis and detection. According to the invention, the dianthrone compound in the polygonum multiflorum is extracted by using ethanol with the volume concentration of 70%, so that the extraction effect rate is high; the invention adopts an internal standard method to detect dianthrone compounds in polygonum multiflorum, thereby improving the detection sensitivity. In addition, acetonitrile and 0.1% formic acid aqueous solution are selected as mobile phases, so that the dianthrone compounds in the polygonum multiflorum have good separation degree, and the detection sensitivity is improved. The invention adopts an electrospray anion tandem mass spectrometry multiple reaction detection (MRM) mode, quickly optimizes mass spectrum parameters including fragmentation voltage and collision energy on line to form a high-strength target ion pair, and achieves quick qualitative and quantitative analysis of dianthrone compounds in polygonum multiflorum medicinal materials through the series of characteristic target ion pairs.
Description
Technical Field
The invention relates to the technical field of chemical analysis and detection, in particular to a method for detecting dianthrone compounds in polygonum multiflorum.
Background
Polygonum multiflorum is one of typical varieties of cooked different therapies and is divided into raw polygonum multiflorum and prepared polygonum multiflorum. Raw radix Polygoni Multiflori is dried root tuber of Polygonum multiflorum Thunb (Polygonum multiflorum Thunb.) of Polygonaceae, has effects of removing toxic substance, resolving carbuncle, preventing malaria, loosening bowel to relieve constipation, etc., and is used for treating skin ulcer, carbuncle, rubella pruritus, chronic malaria, asthenia, and constipation due to intestinal dryness. The processed product of radix Polygoni Multiflori Preparata has effects of nourishing liver and kidney, replenishing essence and blood, blackening hair and beard, strengthening tendons and bones, eliminating turbid pathogen, and reducing blood lipid, and can be used for treating blood deficiency, yellowish complexion, giddiness, tinnitus, premature gray hair, soreness of waist and knees, numbness of limbs, and hyperlipidemia.
The book of materia medica collection states fleece-flower root: raw materials are cold in nature, astringent and toxic; cooked, the temperature is nontoxic ". The polygonum multiflorum has many chemical components, and more than 150 compounds have been found so far, mainly comprising the chemical components of stilbenes, anthraquinones, dianthrones, polyphenols, naphthalenes and the like. In recent years, adverse reactions such as clinical hepatotoxicity of polygonum multiflorum are reported more and more, and the application of polygonum multiflorum is influenced to a certain extent. Research finds that dianthrone components in polygonum multiflorum have certain hepatotoxicity, particularly trans-emodin dianthrone (trans-emodin dianthrones) and cis-emodin dianthrone (cis-emodin dianthrones) show certain toxic effects in embryonic development and hepatotoxicity evaluation models of zebra fish, and indicates why the components may be potential hepatotoxic components in polygonum multiflorum.
Therefore, it is necessary to increase the limit standard of dianthrone component in polygonum multiflorum. At present, no report is found about a method for measuring dianthrone components in polygonum multiflorum by adopting an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry technology.
Disclosure of Invention
In view of this, the present invention provides a method for detecting dianthrone compounds in polygonum multiflorum. The method utilizes an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry to detect the dianthrone compounds in the polygonum multiflorum and has the advantage of high sensitivity.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a method for detecting dianthrone compounds in polygonum multiflorum, which comprises the following steps:
mixing the polygonum multiflorum, the internal standard substance and the extracting agent, and performing ultrasonic treatment to obtain a solution to be detected; the extracting agent is an ethanol solution with the volume concentration of 70%;
detecting the solution to be detected by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method to obtain the peak area ratio of each dianthrone compound in the polygonum multiflorum;
obtaining the content of the dianthrone compounds in the polygonum multiflorum based on a standard curve of the concentration-peak area ratio of the dianthrone compounds;
the dianthrones include Polygonumnolide C4, Polygonumnolide C3, Polygonumnolide C1, Polygonumnolide C2, trans-emodin dianthrone and cis-emodin dianthrone;
the ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method comprises a chromatographic condition and a mass spectrometry condition;
the chromatographic conditions included the following parameters:
a chromatographic column: AgilentZORBAX SB-C18Column, 2.1mm × 50mm,1.8 μm;
column temperature: 30 +/-5 ℃;
flow rate: 0.25 mL/min;
mobile phase A: acetonitrile;
mobile phase B: a formic acid aqueous solution with a mass concentration of 0.1%;
gradient elution procedure:
0-8 min: mobile phase a 37%;
8-10 min: mobile phase a increased from 37% to 60%;
10-12 min: mobile phase a increased from 60% to 78%;
12-20 min: mobile phase a increased from 78% to 90%;
20-22 min: the mobile phase A is reduced from 90% to 37%;
22-30 min: mobile phase a was maintained at 37%;
sample introduction amount: 2.0 mu L;
the mass spectrometry conditions included the following parameters:
mode (2): a negative ion mode;
the scanning mode is as follows: a multi-reaction detection mode;
ejection voltage: 4.0 kV;
ion source temperature: 300 ℃;
pressure of atomizer: 30 psi;
flow rate: 10L/min;
atmosphere: high purity nitrogen.
Preferably, the internal standard is a dianthronyl group.
Preferably, the concentration of the internal standard substance in the solution to be detected is 5-10 mug/mL.
Preferably, the dosage ratio of the polygonum multiflorum and the extracting agent is 1 g: (40-50) mL.
Preferably, the particle size of the polygonum multiflorum is less than or equal to 50 meshes.
Preferably, the power of the ultrasound is 250-1000W, the frequency is 30-50 kHz, and the time is 20-40 min.
The invention provides a method for detecting dianthrone compounds in polygonum multiflorum, which comprises the following steps: mixing the polygonum multiflorum, the internal standard substance and the extracting agent, and performing ultrasonic treatment to obtain a solution to be detected; the extracting agent is an ethanol solution with the volume concentration of 70%; detecting the solution to be detected by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method to obtain the peak area ratio of each dianthrone compound in the polygonum multiflorum; obtaining the content of the dianthrone compounds in the polygonum multiflorum based on a standard curve of the concentration-peak area ratio of the dianthrone compounds; the dianthrones include Polygonumnolide C4, Polygonumnolide C3, Polygonumnolide C1, Polygonumnolide C2, trans-emodin dianthrone and cis-emodin dianthrone; the ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method comprises a chromatographic condition and a mass spectrometry condition; the chromatographic conditions included the following parameters: a chromatographic column: AgilentZORBAX SB-C18Column, 2.1mm × 50mm,1.8 μm; column temperature: 30 +/-5 ℃; flow rate: 0.25 mL/min; mobile phase A: acetonitrile; mobile phase B: a formic acid aqueous solution with a mass concentration of 0.1%; gradient elution procedure: 0-8 min: mobile phase a 37%; 8-10 min: flow ofPhase a increased from 37% to 60%; 10-12 min: mobile phase a increased from 60% to 78%; 12-20 min: mobile phase a increased from 78% to 90%; 20-22 min: the mobile phase A is reduced from 90% to 37%; the time is 22-30 min, and the mobile phase A is maintained at 37%; sample introduction amount: 2.0 mu L; the mass spectrometry conditions included the following parameters: mode (2): a negative ion mode; the scanning mode is as follows: a multi-reaction detection mode; ejection voltage: 4.0 KV; ion source temperature: 300 ℃; pressure of atomizer: 30 psi; flow rate: 10L/min; atmosphere: high purity nitrogen.
According to the invention, the dianthrone compound in the polygonum multiflorum is extracted by using ethanol with the volume concentration of 70%, so that the extraction effect rate is high; the invention adopts an internal standard method to detect dianthrone compounds in polygonum multiflorum, thereby improving the detection sensitivity. In addition, acetonitrile and 0.1% formic acid aqueous solution are selected as mobile phases, so that the dianthrone compounds in the polygonum multiflorum have good separation degree, and the detection sensitivity is improved. The invention adopts an electrospray anion tandem mass spectrometry multiple reaction detection (MRM) mode, quickly optimizes mass spectrum parameters including fragmentation voltage and collision energy on line to form a high-strength target ion pair, and achieves quick qualitative and quantitative analysis of dianthrone compounds in polygonum multiflorum medicinal materials through the series of characteristic target ion pairs.
Drawings
FIG. 1 is a total ion flow diagram of a tested polygonum multiflorum liquid obtained in example 2;
FIGS. 2 to 4 are selected ion flow diagrams of the polygonum multiflorum liquid to be tested obtained in example 2;
FIG. 5 is a total ion current chromatogram of comparative example 2;
FIG. 6 is a total ion current chromatogram of comparative example 3;
wherein 1 IS Polygonumnolide C4, 2 IS Polygonumnolide C3, 3 IS Polygonumnolide C1, 4 IS Polygonumnolide C2, 5 IS trans-emodin dianthrone, 6 IS cis-emodin dianthrone, and IS IS dianthrone group.
Detailed Description
The invention provides a method for detecting dianthrone compounds in polygonum multiflorum, which comprises the following steps:
mixing the polygonum multiflorum, the internal standard substance and the extracting agent, and performing ultrasonic treatment to obtain a solution to be detected; the extracting agent is an ethanol solution with the volume concentration of 70%;
detecting the solution to be detected by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method to obtain the peak area ratio of each dianthrone compound in the polygonum multiflorum;
and obtaining the content of the dianthrone compounds in the polygonum multiflorum based on a standard curve of the concentration-peak area ratio of the dianthrone compounds.
The method comprises the steps of mixing polygonum multiflorum, an internal standard substance and an extracting agent, and carrying out ultrasonic treatment to obtain a solution to be detected.
In the invention, the dianthrone compounds comprise Polygonumnolide C4 with a structure shown in formula I, Polygonumnolide C3 with a structure shown in formula II, Polygonumnolide C1 with a structure shown in formula III, Polygonumnolide C2 with a structure shown in formula IV, trans-emodin dianthrone with a structure shown in formula V and cis-dianthrone with a structure shown in formula VI.
In the present invention, the particle size of the polygonum multiflorum is preferably less than or equal to 50 meshes. In the present invention, the internal standard is preferably a dianthronyl group having a structure represented by formula VII.
In the present invention, the internal standard is added in the form of an internal standard solution, and the solvent of the internal standard solution is preferably a solution of 2: 1 DMSO-methanol solvent; the concentration and the addition amount of the internal standard substance solution are not particularly limited, as long as the concentration of the internal standard substance in the solution to be detected is 5-10 mug/mL, and the concentration is more preferably 6.3 mug/mL.
In the invention, the extracting agent is ethanol water solution with the volume concentration of 70%. In the present invention, the dose ratio of the polygonum multiflorum and the extracting agent is preferably 1 g: (40-50) mL, more preferably 1: 50 mL.
In the invention, the power of the ultrasonic wave is preferably 250-1000W, and more preferably 500W; the frequency is preferably 30-50 kHz, and more preferably 40 kHz; the time is preferably 20 to 40min, and more preferably 30 min.
After the ultrasound is finished, the invention preferably also comprises filtering the obtained ultrasound system, and the pore diameter of the filter membrane for filtering is preferably 0.22 μm.
The ethanol solution with the volume concentration of 70% is used as the extracting agent, so that the extraction efficiency of the dianthrone compounds in the polygonum multiflorum is high; in addition, the internal standard substance dianthrone group is added, so that the detection sensitivity is improved.
After the solution to be detected is obtained, the method utilizes an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry to detect the solution to be detected, and the peak area ratio of each dianthrone compound in the polygonum multiflorum is obtained.
In the invention, the ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry comprises a chromatographic condition and a mass spectrometry condition;
the chromatographic conditions included the following parameters:
a chromatographic column: agilent ZORBAX SB-C18Column, 2.1mm × 50mm,1.8 μm;
column temperature: 30 +/-5 ℃;
flow rate: 0.25 mL/min;
mobile phase A: acetonitrile;
mobile phase B: a formic acid aqueous solution with a mass concentration of 0.1%;
gradient elution procedure:
0-8 min: mobile phase a 37%;
8-10 min: mobile phase a increased from 37% to 60%;
10-12 min: mobile phase a increased from 60% to 78%;
12-20 min: mobile phase a increased from 78% to 90%;
20-22 min: the mobile phase A is reduced from 90% to 37%;
22-30 min: mobile phase a was maintained at 37%;
sample introduction amount: 2.0 mu L;
the mass spectrometry conditions included the following parameters:
mode (2): a negative ion mode;
the scanning mode is as follows: a multi-reaction detection mode;
ejection voltage: 4.0 kV;
ion source temperature: 300 ℃;
pressure of atomizer: 30 psi;
flow rate: 10L/min;
atmosphere: high purity nitrogen.
In the present invention, the MRM parameters of said polygonumnolide c4, polygonumnolide c3, polygonumnolide c1, polygonumnolide c2, trans-emodin dianthrone, cis-emodin dianthrone and dianthrone groups are shown in table 1.
TABLE 1 MRM parameters of dianthrones and dianthrones
Note: in table 1, 1 is polygonumnolide c4, 2 is polygonumnolide c3, 3 is polygonumnolide c1, 4 is polygonumnolide c2, 5 is trans-emodin dianthrone, 6 is cis-emodin dianthrone, and 7 is dianthrone.
In the invention, the obtained peak area ratio of each dianthrone compound in polygonum multiflorum is preferably the peak area ratio of the to-be-detected substance and the internal standard substance, and particularly preferably the peak area ratio of PolygonumnolideC4 and the internal standard substance, the peak area ratio of PolygonumnolideC3 and the internal standard substance, the peak area ratio of PolygonumnolideC1 and the internal standard substance, the peak area ratio of PolygonumnolideC2 and the internal standard substance, the peak area ratio of trans-emodin dianthrone and the internal standard substance, and the peak area ratio of cis-emodin dianthrone and the internal standard substance.
After the peak area ratio of each dianthrone compound in the polygonum multiflorum is obtained, the content of the dianthrone compound in the polygonum multiflorum is obtained based on the standard curve of the concentration-peak area ratio of each dianthrone compound.
In the invention, the standard curves of the concentration-peak area ratio of each dianthrone compound are respectively as follows: a Polygonunnolide C4 concentration-peak area ratio standard curve, a Polygonunnolide C3 concentration-peak area ratio standard curve, a Polygonunnolide C1 concentration-peak area ratio standard curve, a Polygonunnolide C2 concentration-peak area ratio standard curve, a trans-emodin dianthrone concentration-peak area ratio standard curve, and a cis-emodin dianthrone concentration-peak area ratio standard curve.
The method for obtaining the standard curve of the concentration-peak area ratio of each dianthrone compound is not particularly limited, and the standard curve can be drawn by adopting a method for obtaining the standard curve by an internal standard method, which is well known by the technical personnel in the field.
The following examples are provided to describe the detection method of dianthrone compounds in polygonum multiflorum provided by the present invention in detail, but they should not be construed as limiting the scope of the present invention.
In the following embodiments, the parameters for detecting the liquid to be detected by using the ultra performance liquid chromatography-tandem quadrupole mass spectrometry are as follows:
the chromatographic conditions included the following parameters:
a chromatographic column: agilent ZORBAX SB-C18Column, 2.1mm × 50mm,1.8 μm;
column temperature: 30 +/-5 ℃;
flow rate: 0.25 mL/min;
mobile phase A: acetonitrile;
mobile phase B: a formic acid aqueous solution with a mass concentration of 0.1%;
gradient elution procedure:
0-8 min: mobile phase a 37%;
8-10 min: mobile phase a increased from 37% to 60%;
10-12 min: mobile phase a increased from 60% to 78%;
12-20 min: mobile phase a increased from 78% to 90%;
20-22 min: the mobile phase A is reduced from 90% to 37%;
22-30 min: mobile phase a was maintained at 37%;
sample introduction amount: 2.0 mu L;
the mass spectrometry conditions included the following parameters:
mode (2): a negative ion mode;
the scanning mode is as follows: a multi-reaction detection mode;
ejection voltage: 4.0 kV;
ion source temperature: 300 ℃;
pressure of atomizer: 30 psi;
flow rate: 10L/min;
atmosphere: high purity nitrogen.
Example 1
Preparation of control solutions:
the control substances Polygonumnolide C4, Polygonumnolide C3, Polygonumnolide C1, Polygonumnolide C2, trans-emodin dianthrone and cis-emodin dianthrone were precisely weighed and dissolved in 70 vol.% ethanol to prepare a mixed standard stock solution having a concentration of Polygonumnolide C4 of 0.210. mu.g/mL, Polygonumnolide C3 of 0.214. mu.g/mL, Polygonumnolide C1 of 0.283. mu.g/mL, Polygonumnolide C2 of 0.280. mu.g/mL, trans-emodin dianthrone of 0.318. mu.g/mL and cis-emodin dianthrone of 0.280. mu.g/mL.
An internal standard dianthrone base 25.11mg was precisely weighed and dissolved in DMSO/methanol (wherein the volume ratio of DMSO to methanol is 2: 1) to obtain an internal standard solution with a concentration of 100.44. mu.g/mL.
Diluting the concentration of each substance in the mixed standard stock solution to 0.6 time, 0.4 time, 0.2 time, 0.1 time, 0.08 time, 0.04 time, 0.02 time and 0.01 time respectively to obtain a series of mixed standard solutions; respectively adding 0.1mL of internal standard substance solution into 1.5mL of series of standard mixed solutions before detection for detection; the results of linear regression on 6 pairs of photographs were obtained using the mass concentration of the mixed standard solution as the abscissa (X) and the peak area ratio of the bisanthronyl group of each control and internal standard as the ordinate (Y), respectively, and are shown in table 2.
According to the ratio (signal-to-noise ratio) of the detection signal height to the baseline noise height being 3: 1, determining a detection Limit (LOD); the results are shown in Table 2.
According to the ratio (signal-to-noise ratio) of the detection signal height to the baseline noise height of 10: 1, the limit of quantitation (LOQ) was determined, and the results are shown in Table 2.
TABLE 2 regression equation, correlation coefficient, linear range, quantitative limit and detection limit summary results for dianthrones in Polygonum multiflorum
Note: in Table 2, 1 is Polygonumnolide C4, 2 is Polygonumnolide C3, 3 is Polygonumnolide C1, 4 is Polygonumnolide C2, 5 is trans-emodin dianthrone, and 6 is cis-emodin dianthrone.
As can be seen from table 2: the content of 6 dianthrones in Polygonum multiflorum has good correlation coefficient (R) in linear range2Not less than 0.99), and the detection method has relatively low detection limit and quantification limit, which indicates that the method has high sensitivity and accuracy.
Example 2
Precisely weighing about 1.0g of polygonum multiflorum medicinal material powder (passing through a third sieve), placing the powder into a conical flask with a plug, precisely adding 50mL of 70% ethanol solution, weighing, carrying out ultrasonic treatment (power 500W and frequency 40kHz) for 30 minutes, taking out, cooling, weighing again, complementing the loss weight by 70% ethanol solution, shaking up, filtering, passing through a 0.22 mu m filter membrane, and taking the subsequent filtrate to obtain the polygonum multiflorum medicinal material powder. Adding 0.1mL of internal standard solution into 1.5mL of filtrate for detection, wherein the total ion flow diagram of the obtained polygonum multiflorum liquid to be detected is shown in figure 1; FIGS. 2 to 4 are selected ion flow diagrams of the obtained polygonum multiflorum liquid to be tested; in FIGS. 1 to 4, 1 IS Polygonumnolide C4, 2 IS Polygonumnolide C3, 3 IS Polygonumnolide C1, 4 IS Polygonumnolide C2, 5 IS trans-emodin dianthrone, 6 IS cis-emodin dianthrone, and IS IS dianthrone group. As can be seen from fig. 1 to 4: the detection method provided by the invention can be used for simultaneously determining the contents of six dianthrone compounds.
Example 3
3.1 precision test
The polygonum multiflorum liquid to be detected is prepared according to the method disclosed in the embodiment 2, the polygonum multiflorum liquid to be detected is continuously and fully injected for 6 times within 24 hours by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method, the sample injection is repeated for 3 times every day for 72 hours continuously, and the calculation is carried out according to the corresponding peak area ratio and the Relative Standard Deviation (RSD) of the retention time, and the result is shown in the table 3.
TABLE 3 precision test results of dianthrones in Polygonum multiflorum
Note: in Table 3, 1 is Polygonumnolide C4, 2 is Polygonumnolide C3, 3 is Polygonumnolide C1, 4 is Polygonumnolide C2, 5 is trans-emodin dianthrone, and 6 is cis-emodin dianthrone.
As can be seen from table 3: the Relative Standard Deviation (RSD) of the ratio of the relative peak areas of the polygonum multiflorum to be detected in the day and in the daytime is less than 5.0 percent, which shows that the detection method provided by the invention has good precision.
3.2 repeatability test
Taking 1 part of the same batch of polygonum multiflorum medicinal material powder, preparing polygonum multiflorum liquid to be detected according to the method in example 2, carrying out continuous sample injection for 6 times by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry, carrying out detection, and calculating the peak area ratio of 6 dianthrone compounds to the peak area of an internal standard substance, wherein the results are shown in table 4.
TABLE 4 repeatability test results of dianthrones in Polygonum multiflorum
Note: in Table 4, 1 is Polygonumnolide C4, 2 is Polygonumnolide C3, 3 is Polygonumnolide C1, 4 is Polygonumnolide C2, 5 is trans-emodin dianthrone, and 6 is cis-emodin dianthrone.
As can be seen from table 4: the Relative Standard Deviation (RSD) range of the relative peak area ratio of the polygonum multiflorum to-be-detected liquid is 1.73-3.24%, and the RSD range does not exceed 5.0%, so that the method has good repeatability.
3.3 reproducibility test
Taking one part of each of 6 different batches of polygonum multiflorum medicinal material powder, preparing polygonum multiflorum liquid to be detected according to the method in example 2, detecting by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry, and calculating the content of 6 dianthrones, wherein the results are shown in table 5.
TABLE 5 results of reproducibility test of dianthrones in Polygonum multiflorum
Note: in Table 5, 1 is Polygonumnolide C4, 2 is Polygonumnolide C3, 3 is Polygonumnolide C1, 4 is Polygonumnolide C2, 5 is trans-emodin dianthrone, and 6 is cis-emodin dianthrone.
As can be seen from Table 5, the Relative Standard Deviation (RSD) range of the peak area ratio of the polygonum multiflorum to-be-detected liquid is 1.23-3.30%, and the peak area ratio does not exceed 4.0%, which indicates that the detection method provided by the invention has good repeatability.
3.4 stability test
The polygonum multiflorum liquid to be tested is prepared according to the method in the embodiment 2, samples are injected for one time in 0, 2, 4, 8, 12 and 24h respectively by taking 24h as a period, the peak area ratio of 6 dianthrone compounds to the peak area ratio of the internal standard substance is calculated, the Relative Standard Deviation (RSD) of the peak area ratios is calculated, and the result is shown in the table 6.
TABLE 6 stability test results of dianthrones in Polygonum multiflorum
| Compound (I) | 0h | 2h | 4h | 8h | 12h | 24h | Mean value of | |
| 1 | 0.300 | 0.324 | 0.334 | 0.310 | 0.320 | 0.323 | 0.319 | 3.41 |
| 2 | 0.246 | 0.259 | 0.275 | 0.261 | 0.262 | 0.263 | 0.261 | 3.55 |
| 3 | 0.291 | 0.307 | 0.319 | 0.310 | 0.291 | 0.306 | 0.304 | 3.64 |
| 4 | 0.385 | 0.393 | 0.422 | 0.400 | 0.385 | 0.382 | 0.3945 | 3.47 |
| 5 | 1.938 | 2.064 | 2.155 | 2.039 | 2.014 | 1.949 | 2.027 | 3.95 |
| 6 | 1.764 | 1.892 | 1.927 | 1.840 | 1.787 | 1.769 | 1.830 | 3.73 |
Note: in Table 6, 1 is Polygonumnolide C4, 2 is Polygonumnolide C3, 3 is Polygonumnolide C1, 4 is Polygonumnolide C2, 5 is trans-emodin dianthrone, and 6 is cis-emodin dianthrone.
As can be seen from Table 6, the Relative Standard Deviation (RSD) range of the relative peak area ratio of the polygonum multiflorum to-be-detected liquid is 3.41-3.95%, and the RSD range is not more than 4.0%, which indicates that the detection method provided by the invention has good stability.
3.5 sample application recovery test
Taking 6 parts of polygonum multiflorum powder with known content of 6 dianthrones, precisely weighing 0.5g of polygonum multiflorum powder, adding 6 dianthrone mixed standard stock solutions, preparing according to the preparation method of polygonum multiflorum liquid to be detected, detecting by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry, and calculating the recovery rate, wherein the results are shown in table 7.
TABLE 7 sample application recovery rate test results of dianthrones compounds in Polygonum multiflorum
Note: in Table 7, 1 is Polygonumnolide C4, 2 is Polygonumnolide C3, 3 is Polygonumnolide C1, 4 is Polygonumnolide C2, 5 is trans-emodin dianthrone, and 6 is cis-emodin dianthrone.
As can be seen from table 7: the sample recovery rate of 6 dianthrone compounds is 104.38-150.4%, which shows that the method has better recovery rate.
(M) recovery rate1-M2) Per M × 100%, where M1For the measured total amount of the target component, M2M is the amount of dianthrone standard added, which is the amount of the target component in the fleece-flower root sample.
Example 4
Weighing 1.0g of 20 batches of polygonum multiflorum in different batches, and precisely weighing;
the test solution was prepared as follows: taking about 1.0g of polygonum multiflorum medicinal material powder (screened by a third sieve), placing the powder into a conical flask with a plug, precisely adding 50mL of ethanol solution with the volume concentration of 70%, weighing, carrying out ultrasonic treatment (the power is 100W, the frequency is 40kHz) for 30 minutes, taking out, cooling, weighing again, complementing the weight loss by 70% ethanol, shaking up, filtering by a filter membrane with the diameter of 0.22 mu m, and taking the subsequent filtrate to obtain the liquid to be tested.
Adding 0.1mL of internal standard substance solution into 1.5mL of solution to be detected to obtain polygonum multiflorum solution to be detected;
the sample injection detection under the conditions is adopted, the chromatogram is recorded, and the detection result is shown in Table 8.
TABLE 820 Total content of 6 dianthrones in Polygonum Multiflorum samples (. mu.g/g)
Note: in Table 8, 1 is Polygonumnolide C4, 2 is Polygonumnolide C3, 3 is Polygonumnolide C1, 4 is Polygonumnolide C2, 5 is trans-emodin dianthrone, and 6 is cis-emodin dianthrone.
As can be seen from Table 8, the total content of Polygonunolide C4(1), Polygonunolide C3(2), Polygonunolide C1(3), Polygonunolide C2(4), trans-emodin dianthrone (5) and cis-emodin dianthrone (6) was very low in 20 lots of Polygonum multiflorum medicinal materials from different producing areas; the content of the compounds 5 and 6 is obviously higher than that of the compounds 1-4; the total content range of the 6 dianthrones compounds in 20 batches of medicinal materials is 1.98 mu g/g-143.17 mu g/g.
Comparative example 1
Precisely weighing about 1.0g of polygonum multiflorum medicinal material powder (passing through a third sieve), placing the powder into a conical flask with a plug, precisely adding 50mL of water, 30% ethanol, 50% ethanol, 70% ethanol and 95% ethanol solution with volume concentration, weighing, carrying out ultrasonic treatment (power 500W, frequency 40kHz) for 30 minutes, taking out, cooling, weighing again, complementing the weight loss by the volume concentration of the extracted solution, shaking up, filtering, passing through a 0.22 mu m filter membrane, and taking the subsequent filtrate to obtain the polygonum multiflorum medicinal material powder. And adding 0.1mL of internal standard substance solution into 1.5mL of filtrate to obtain a solution to be detected for determination. The results are shown in Table 9.
TABLE 9 optimization of different extraction solvents
| Different extraction solvents | 1(A sample/A internal standard) | 2(A sample/A internal standard) | 3(A sample/A internal standard) | 4(A sample/A internal standard) | 5(A sample/A internal standard) | 6(A sample/A internal standard) |
| Water (W) | 0.0079 | 0.0058 | 0.0051 | 0.0064 | 0.0455 | 0.0336 |
| 30% ethanol | 0.1032 | 0.0692 | 0.0990 | 0.1014 | 0.2708 | 0.2998 |
| 50% ethanol | 0.2227 | 0.1655 | 0.2022 | 0.31572 | 1.4726 | 1.0434 |
| 70% ethanol | 0.2545 | 0.1992 | 0.2362 | 0.3384 | 2.0247 | 1.5993 |
| 95% ethanol | 0.1564 | 0.1146 | 0.1441 | 0.2317 | 1.0051 | 0.6467 |
As can be seen from table 9: the 6 dianthrone compounds obtained by the ethanol water solution ultrasonic extraction method with the volume concentration of 70% have higher relative peak areas and better extraction efficiency.
Comparative example 2
Precisely weighing about 1.0g of polygonum multiflorum medicinal material powder (passing through a third sieve), placing the polygonum multiflorum medicinal material powder in a conical flask with a plug, precisely adding 25mL, 50mL, 100mL and 150mL of ethanol solution with volume concentration of 70%, weighing, ultrasonically treating (with power of 500W and frequency of 40kHz) for 30 minutes, taking out, cooling, weighing again, complementing the lost weight with the ethanol solution with volume concentration of 70%, shaking up, filtering, passing through a 0.22 mu m filter membrane, and taking the subsequent filtrate to obtain the polygonum multiflorum medicinal material powder. And adding 0.1mL of internal standard substance solution into 1.5mL of filtrate to obtain a solution to be detected for determination.
The results are shown in table 10 and fig. 5.
TABLE 10 optimization of different extraction solvent volumes
| Volume of different solvents | 1(A sample/A internal standard) | 2(A sample/A internal standard) | 3(A sample/A internal standard) | 4(A sample/A internal standard) | 5(A sample/A internal standard) | 6(A sample/A internal standard) |
| 25mL | 0.6351 | 0.5459 | 0.7026 | 0.8790 | 4.2592 | 3.4757 |
| 50mL | 0.3188 | 0.2646 | 0.3209 | 0.4370 | 2.2832 | 1.7980 |
| 100mL | 0.1499 | 0.1125 | 0.1481 | 0.2137 | 1.0931 | 0.8287 |
| 150mL | 0.1036 | 0.0788 | 0.0972 | 0.1462 | 0.7587 | 0.5860 |
As can be seen from table 10 and fig. 5: the 50mL ethanol water solution ultrasonic extraction method with the volume concentration of 70% adopted by the invention has the advantages that the relative peak area of the 6 dianthrone compounds is higher, and the extraction efficiency is better.
Comparative example 3
Precisely weighing about 1.0g of polygonum multiflorum medicinal material powder (passing through a third sieve), placing the powder in a conical flask with a plug, precisely adding 50ml of ethanol solution with the volume concentration of 70%, weighing, carrying out ultrasonic treatment (the power is 500W, the frequency is 40kHz) for 15, 30 and 45 minutes, taking out, cooling, weighing again, complementing the lost weight with the ethanol solution with the volume concentration of 70%, shaking uniformly, filtering, passing through a filter membrane with the volume concentration of 0.22 mu m, and taking the subsequent filtrate to obtain the polygonum multiflorum medicinal material powder. And adding 0.1mL of internal standard substance solution into 1.5mL of filtrate to obtain a solution to be detected for determination.
The results are shown in table 11 and fig. 6.
TABLE 11 different time optimization results of ultrasound extraction
As can be seen from table 11 and fig. 6: the method adopts 50ml of ethanol water solution with volume concentration of 70 percent to carry out ultrasonic extraction for 30 minutes to obtain 6 dianthrone compounds with higher relative peak area and better extraction efficiency.
According to the embodiments, the ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry combined method is adopted, an electrospray anion tandem mass spectrometry multiple reaction detection (MRM) mode is adopted, mass spectrum parameters including fragmentation voltage and collision energy are optimized on line rapidly, a high-strength target ion pair is formed, and rapid qualitative and quantitative analysis of dianthrone compounds in the polygonum multiflorum medicinal material is achieved through the series of characteristic target ion pairs; the detection method provided by the invention is simple to operate, has high sensitivity and precision, good reproducibility, high stability and good recovery rate, can realize simultaneous determination of dianthrone compounds contained in the polygonum multiflorum, makes up for the defects of incomplete and scientific quality control technology of the existing polygonum multiflorum medicinal material, and can accurately and comprehensively control the quality of the polygonum multiflorum medicinal material.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. A detection method of dianthrone compounds in polygonum multiflorum is characterized by comprising the following steps:
mixing the polygonum multiflorum, the internal standard substance and the extracting agent, and performing ultrasonic treatment to obtain a solution to be detected; the extracting agent is an ethanol solution with the volume concentration of 70%;
detecting the solution to be detected by using an ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method to obtain the peak area ratio of each dianthrone compound in the polygonum multiflorum;
obtaining the content of the dianthrone compounds in the polygonum multiflorum based on a standard curve of the concentration-peak area ratio of the dianthrone compounds;
the dianthrones include Polygonumnolide C4, Polygonumnolide C3, Polygonumnolide C1, Polygonumnolide C2, trans-emodin dianthrone and cis-emodin dianthrone;
the ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry method comprises a chromatographic condition and a mass spectrometry condition;
the chromatographic conditions included the following parameters:
a chromatographic column: agilent ZORBAX SB-C18Column, 2.1mm × 50mm,1.8 μm;
column temperature: 30 +/-5 ℃;
flow rate: 0.25 mL/min;
mobile phase A: acetonitrile;
mobile phase B: a formic acid aqueous solution with a mass concentration of 0.1%;
gradient elution procedure:
0-8 min: mobile phase a 37%;
8-10 min: mobile phase a increased from 37% to 60%;
10-12 min: mobile phase a increased from 60% to 78%;
12-20 min: mobile phase a increased from 78% to 90%;
20-22 min: the mobile phase A is reduced from 90% to 37%;
22-30 min: mobile phase a was maintained at 37%;
sample introduction amount: 2.0 mu L;
the mass spectrometry conditions included the following parameters:
mode (2): a negative ion mode;
the scanning mode is as follows: a multi-reaction detection mode;
ejection voltage: 4.0 kV;
ion source temperature: 300 ℃;
pressure of atomizer: 30 psi;
flow rate: 10L/min;
atmosphere: high purity nitrogen.
2. The detection method according to claim 1, wherein the internal standard substance is a dianthrone group.
3. The detection method according to claim 1 or 2, wherein the concentration of the internal standard substance in the solution to be detected is 5-10 μ g/mL.
4. The detection method according to claim 1, wherein the dose ratio of the polygonum multiflorum and the extractant is 1 g: (40-50) mL.
5. The detection method according to claim 1, wherein the particle size of the polygonum multiflorum is less than or equal to 50 meshes.
6. The detection method according to claim 1, wherein the power of the ultrasonic wave is 250-1000W, the frequency is 30-50 kHz, and the time is 20-40 min.
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