CN117630213A - Method for simultaneously measuring multiple chemical components in dracocephalum heterophyllum - Google Patents
Method for simultaneously measuring multiple chemical components in dracocephalum heterophyllum Download PDFInfo
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- 241000346136 Dracocephalum heterophyllum Species 0.000 title claims abstract description 38
- 239000000126 substance Substances 0.000 title claims abstract description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000001195 ultra high performance liquid chromatography Methods 0.000 claims abstract description 22
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000001514 detection method Methods 0.000 claims abstract description 13
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- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention discloses a method for simultaneously measuring a plurality of chemical components in dracocephalum heterophyllum, and relates to the technical field of separation and analysis of natural products. Determining chemical components of the dracocephalum heterophyllum by adopting ultra-high performance liquid chromatography at the same time, wherein the chemical components at least comprise neochlorogenic acid, cryptochlorogenic acid and geraniin-7-O-glucuronide; the detection conditions of the ultra-high performance liquid chromatography include: chromatographic column stationary phase: diisobutyl is bonded to the silica gel surface through siloxane; mobile phase A is selected from methanol or acid-containing methanol, mobile phase B is selected from water or acid-containing aqueous solution; and (3) carrying out gradient elution by using the mobile phase A and the mobile phase B as mixed mobile phases. The invention establishes a method for measuring the UPLC content of various chemical components in the dracocephalum heterophyllum, and the method has the advantages of simple operation, reliable result and good repeatability, and can provide a certain reference for measuring the content of the chemical components in the dracocephalum heterophyllum and perfecting the existing quality standard.
Description
Technical Field
The invention relates to the technical field of separation and analysis of natural products, in particular to a method for simultaneously measuring various chemical components in dracocephalum heterophyllum.
Background
The dracocephalum heterophyllum is also called as "white flower branch flower", which is the dry aerial part of the plant Dracocephalum heterophyllum benth of the plant of the genus plant of the family Labiatae, the Tibetan medicine is called as "Ji Ziqing Bao", which is recorded in 1995 edition of medicine Standard of Ministry of health, and the whole plant can be used as a medicine, and is a common medicine in national areas. It is mostly grown on hillside grasslands, river beaches, etc. with an altitude of 2000-5000m, and is distributed in Qinghai, tibet, gansu, northwest of Sichuan, xinjiang, etc. The Chinese medicine dictionary records that the dracocephalum heterophyllum has the effects of suppressing hyperactive liver, relieving internal heat and the like, and can be used for treating diseases such as swelling and pain of gum, dental ulcer and the like caused by icterohepatitis and ascending of liver fire. The Tibetan medicine classic "Jingzhu Ben Cao" records that Qinglan Cao can treat stomatopathy and odontopathy. Modern researches have found that the dracocephalum heterophyllum contains various chemical components such as flavone, volatile oil, alkaloid, triterpene and steroid, and has various active effects such as antioxidation, anti-inflammatory, cough and asthma relieving, liver protecting and cardiovascular protecting.
As a prescription drug, dracocephalum heterophyllum is widely used in Tibetan drug classic compound seventy-ingredient pine stone pills, three-ingredient manna powder, ginseng clam asthma relieving capsules, but lacks chemical components and quality control indexes. At present, the standard of the dracocephalum heterophyllum only has the ministerial standard, and the quality of medicinal materials cannot be effectively controlled. Studies show that the dracocephalum heterophyllum contains chemical components such as luteolin, rosmarinic acid, oleanolic acid, wu Su Jia ester, chlorogenic acid, luteolin and the like, and only the simultaneous determination of the contents of two or four components is reported in the literature at present.
Disclosure of Invention
The invention aims to provide a method for simultaneously measuring a plurality of chemical components in the dracocephalum heterophyllum, and an ultra-high performance liquid chromatography (UPLC) is adopted to establish a method for simultaneously measuring 9 chemical components such as chlorogenic acid, cryptochlorogenic acid, acteoside, luteolin, rosmarinic acid, geraniin-7-O-glucuronide, quercetin, luteolin and the like, and the method is applied to the content measurement of the chemical components in the dracocephalum heterophyllum in different production places so as to provide a certain reference for the quality standard research and comprehensive utilization of the chemical components in the dracocephalum heterophyllum.
In order to solve the technical problems, the invention adopts the following technical scheme:
a method for simultaneously measuring a plurality of chemical components in the dracocephalum heterophyllum comprises the steps of measuring the chemical components of the dracocephalum heterophyllum by adopting ultra-high performance liquid chromatography, wherein the chemical components at least comprise neochlorogenic acid, cryptochlorogenic acid and myrosinin-7-O-glucuronide;
the detection conditions of the ultra-high performance liquid chromatography include:
chromatographic column stationary phase: diisobutyl is bonded to the silica gel surface through siloxane;
mobile phase A is selected from methanol or acid-containing methanol, mobile phase B is selected from water or acid-containing aqueous solution;
gradient elution is adopted, and the gradient elution program of the first 60min is as follows:
0-15min，25％-25％ A；15-25min，25％-35％ A；25-26min，35％-38％ A；26-40min，38％-45％ A；40-42min，45％-45％ A；42-50min，45％-60％ A；50-60min，60％-90％A。
further, the chromatographic column is Agilent ZORBOX SB-C18.
Further, the mobile phase A is methanol containing 0.1-0.3% formic acid, and the mobile phase B is 0.1-0.3% formic acid aqueous solution.
Further, in the gradient elution procedure, the method further includes: 60-62min,90% -100% of A;62-65min,100% -100% A.
Further, the conditions of the ultra performance liquid chromatography further include one or more of the following iv:
i specification of chromatographic column: 4.6X100 mm,1-5 μm;
ii column temperature: 30-40 ℃;
iii flow rate: 0.1-0.5 mL/min -1 ；
iv detection wavelength: 210-360nm;
further, the conditions of the ultra performance liquid chromatography further include one or more of the following iv:
i specification of chromatographic column: 4.6X100 mm,1.8 μm;
ii column temperature: 35 ℃;
iii flow rate: 0.3mL min -1 ；
iv detection wavelength: 340nm
Further, the chemical component further comprises chlorogenic acid, acteoside, luteolin, rosmarinic acid, quercetin or luteolin.
The novel chlorogenic acid has various biological activities such as antioxidation, anti-inflammatory, antibacterial, antiviral and the like, and is widely applied to the research and development of anti-tumor, anticancer, antidiabetic and other medicaments in the field of medicine; the acteoside has various physiological functions such as antioxidation, anti-inflammatory reaction, neuroprotection, immunoregulation, anti-tumor, wound healing and the like, and has advanced in neuroprotection in neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease; cryptochlorogenic acid has effects of resisting platelet aggregation, resisting bacteria, and relieving inflammation; quercetin has antioxidant, antiinflammatory, anticancer, cardiovascular protecting and antiallergic effects; the geraniin-7-O-glucuronide is used as the main component in the effective part of the moldavica dragonhead, and possibly has the pharmacological effects of resisting myocardial ischemia, atherosclerosis and the like of the effective part of the moldavica dragonhead.
According to the invention, the new chlorogenic acid, the cryptochlorogenic acid and the myrosin-7-O-glucuronide are identified from the dracocephalum heterophyllum by first analysis, and the quality of medicinal materials of the dracocephalum heterophyllum can be intuitively reflected by measuring the components.
Further, the preparation method of the sample solution comprises the following steps: extracting a sample to be detected by using 70-80% methanol, filtering, and filtering the filtrate by a filter membrane to obtain a sample solution.
Further, the solvent is 75% methanol solution.
The extraction method can be reflux, soaking, ultrasonic and other conventional methods.
The use of filters is a conventional procedure prior to liquid injection in order to avoid clogging the column. The pore size of the conventional filter is 0.45 μm, and of course, the above object can be achieved by using a smaller pore size filter.
The invention adopts UPLC content determination method and uses ZORBOX SB-C18 colorA chromatographic column, which uses 0.1% formic acid-methanol (A) -0.1% formic acid aqueous solution (B) as a mobile phase, the specification of the chromatographic column is 4.6X100 mm, the flow rate is 0.3 mL.min -1 Under the conditions of detection wavelength 340nm, column temperature 35 ℃ and sample injection amount 2 mu L, under the gradient elution condition: gradient elution (0-15 min, 25-25% A, 15-25min, 25-35% A, 25-26min, 35-38% A, 26-40min, 38-45% A, 40-42min, 45-45% A, 42-50min, 45-60% A, 50-60min, 60-90% A, 60-62min, 90-100% A, 62-65min, 100-100% A) has better separation degree of target chromatographic peaks, and the method is simple and convenient to operate, reliable in result and good in repeatability.
The concentration, or percentage, of the solution described in the present invention is the volume ratio.
The beneficial effects of the invention are as follows:
the invention establishes a UPLC content measuring method for 9 chemical components in the dracocephalum heterophyllum, and the method has the advantages of simple operation, reliable result and good repeatability, can provide a certain reference for measuring the content of the chemical components in the dracocephalum heterophyllum and perfecting the existing quality standard, and has important significance for the quality control of the dracocephalum heterophyllum and the quality standard formulation of related medicinal materials.
Drawings
FIG. 1 UPLC chromatogram of the mixed control solution;
FIG. 21 UPLC chromatogram obtained under elution program;
FIG. 32 UPLC chromatogram obtained under elution program;
FIG. 43 UPLC chromatogram obtained under elution program;
FIG. 5 UPLC chromatogram of sample solution (obtained under elution procedure No. 4);
reference numerals: 1-neochlorogenic acid, 2-chlorogenic acid, 3-cryptochlorogenic acid, 4-acteoside, 5-luteolin, 6-rosmarinic acid, 7-geranylgeraniol-7-O-glucuronide, 8-quercetin, 9-luteolin.
Detailed Description
The following description of the present invention will be made clearly and fully, and it is apparent that the embodiments described herein are only some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to fall within the scope of the invention.
Example 1
1. Instrument and reagent
Aglient-G6500 ultra high performance liquid chromatograph (Agilent, U.S.A.). JP100-S type ultrasonic cleaner (Shenzhen clean Equipment Co., ltd.). New chlorogenic acid, cryptochlorogenic acid, geraniin-7-O-glucuronide control (beijing na-gang biotechnology institute); acteoside, luteolin, rosmarinic acid, luteolin, quercetin control (Shanghai source leaf biotechnology Co., ltd.); chlorogenic acid reference substance (Beijing northern Weijingjingku technology institute) has purity of more than 98%. The water is purified water, the methanol is chromatographic purity, and the rest reagents are analytical purity.
The dracaena fragrans samples are collected in various areas of the Qinghai province in 2023, 7 months to 8 months, the information of the samples is shown in table 1, and the whole plant is crushed after natural drying.
TABLE 1 information on samples of Isophyllum inophyllum
2. Method and results
2.1 chromatographic conditions
Gradient elution (0-15 min, 25-25% A, 15-25min, 25-35% A, 25-26min, 35-38% A, 26-40min, 38-45% A, 40-42min, 45-45% A, 42-50min, 45-60% A, 50-60min, 60-90% A, 60-62min, 90-100% A, 62-65min, 100-100% A) with a flow rate of 0.3 mL.min) using ZORBOX SB-C18 column (4.6X100 mm,1.8 μm) with mobile phase of 0.1% methanol (A) -0.1% aqueous formic acid (B) -1 The detection wavelength is 340nm, the column temperature is 35 ℃, and the sample injection amount is 2 mu L. Taking mixed reference substance and sample solution, introducing under the above chromatographic conditions, wherein UPLC chromatogram of the mixed reference substance is shown in figure 1, UPLC chromatogram of the sample solution is shown in figure 5, and target color is known from figure 5The separation degree of the spectrum peak is good.
2.2 preparation of solutions
Precisely weighing 9 standard reference substances such as neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, acteoside, luteolin, rosmarinic acid, geraniin-7-O-glucuronide, quercetin, luteolin, etc., and adding methanol to prepare into the final product with concentrations of 0.030, 0.180, 0.030, 0.090, 0.110, 0.200, 0.070 and 0.030 mg.mL -1 Is prepared from the mixed reference stock solution.
Precisely weighing 1.000g of the whole strain sample powder of the dracocephalum heterophyllum, placing the whole strain sample powder in a conical flask, precisely adding 10mL of 75% methanol, weighing, performing ultrasonic treatment for 30min, cooling to room temperature, supplementing the missing weight with 75% methanol, shaking uniformly, filtering to obtain filtrate, and filtering with a 0.45 μm filter membrane to obtain the sample solution.
2.3 linear relationship investigation
Respectively sucking 0.2, 0.5, 2, 4, and 6 μl of mixed reference solution, and introducing under "2.1" medium chromatography condition to obtain concentration (μg·ml) represented by reference substance contained in the sample -1 ) Linear regression was performed on the abscissa and the peak area on the ordinate to obtain regression equations and linear parameters of each component as shown in table 2.
Table 29 linear regression equation, correlation coefficient, linear range of chemical composition
2.4 precision, repeatability and stability assays
Taking the mixed reference substance solution, continuously sampling for 6 times in 1d according to the chromatographic condition in the item "2.1", and finally calculating to obtain the peak area RSD values of each reference substance, which are respectively 1.89%, 0.90%, 1.40%, 0.96%, 1.69%, 1.04%, 1.07%, 0.86% and 2.44% (n=6), wherein the instrument precision is good.
Taking S3 dracocephalum heterophyllum samples, preparing 6 parts of test sample solutions in parallel according to the method in the item of 2.2, and carrying out sample injection measurement according to the chromatographic condition in the item of 1.2.1, and finally calculating 9 chemical component peak areas RSD of 2.61%, 1.02%, 0.62%, 1.52%, 1.90%, 0.38%, 0.84%, 2.71% and 1.12% (n=6) respectively, which indicates that the repeatability of the method is good.
Sample injection is carried out on sample solutions of S3 dracocephalum heterophyllum according to the chromatographic conditions of 1.2.1 item when the sample solutions are respectively used for 0, 2, 4, 6, 8 and 12 hours, and finally, the peak areas RSD of 9 chemical components are respectively calculated to be 0.62%, 0.21%, 3.61%, 0.16%, 0.93%, 0.32%, 0.31%, 1.53% and 0.46% (n=6), so that the sample solutions are good in stability within 12 hours.
2.5 sample recovery test
Accurately weighing 1.000g of S3 whole strain sample powder of blue green leaf, accurately adding neochlorogenic acid (0.020 mg.mL) prepared by 75% methanol (v/v) -1 ) Chlorogenic acid (0.130 mg.mL) -1 ) Cryptochlorogenic acid (0.050 mg.mL) -1 ) Acteoside (0.100 mg.mL) -1 ) Oleacosides (0.080 mg.mL) -1 ) Rosmarinic acid (0.180 mg. ML) -1 ) Pelargonium graveolens-7-O-glucuronide (0.070 mg. ML) -1 ) Quercetin (0.030 mg.mL) -1 ) Luteolin (0.050 mg.mL) -1 ) 10mL of the control solution was mixed, and a test solution was prepared according to the method described in item "2.2". And (5) respectively sampling according to the chromatographic conditions in the item of 2.1, and calculating the sampling recovery rate. The average sample recovery rates of the chlorogenic acid, the cryptochlorogenic acid, the acteoside, the luteolin, the rosmarinic acid, the geraniin-7-O-glucuronide, the quercetin and the luteolin are respectively 100.9%, 93.18%, 103.3%, 112.61%, 90.25%, 96.67%, 97.02%, 101.11% and 97.07%, and the corresponding RSD values are less than 1.25% (n=6).
2.6 determination of sample content
10 batches of whole strain samples of the dracocephalum heterophyllum from 9 production places are weighed, a test solution is prepared according to the item "2.2", and the test solution is measured according to the chromatographic condition in the item "2.1", so that the content of 9 chemical components in the dracocephalum heterophyllum is calculated, and the measurement result is shown in Table 3.
TABLE 3 determination of the chemical content of Isophyllum inophyllum in different production areas (mg.g) -1 ，n＝3)
The results in Table 3 show that the highest rosmarinic acid content was found in 10 samples of Vanilla dysaria at different sites, followed by chlorogenic acid. Comparing chemical components in different producing areas of the dracocephalum heterophyllum, the difference of the species is smaller, but the difference is obvious in content, wherein the difference of the rosmarinic acid content is the largest, and the rosmarinic acid content in the Ledu S4 sample is as high as 13.01 mg.g -1 While the content of rosmarinic acid in the S1 sample is 3.455 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the Chlorogenic acid reaches 3.043 mg.g with highest content in the S2 sample -1 While the chlorogenic acid content in Minhe S5 sample is only 0.009 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the The highest content of the neochlorogenic acid in the S2 sample is 0.464 mg.g -1 Whereas in the case of the samples of the pretty S10, it was only 0.015 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the Cryptochlorogenic acid is contained in the highest amount in the S2 sample of the same De, and is 0.864 mg.g -1 While the content of the cystitis S10 sample is only 0.119 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the Acteoside reaches 1.029mg.g in Minhe S5 sample -1 Whereas in the case of the samples of the pretty S10, it was only 0.016 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the The content of luteolin in Minhe S5 sample is highest and reaches 1.052mg.g -1 The content of the S1 sample is the lowest and is only 0.170 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the The content of the geraniin-7-O-glucuronide in the Min and S5 samples reaches 1.070 mg.g -1 And in the S8 sample of the gate source, the concentration is only 0.051 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the Quercetin is contained in Minhe S5 sample as high as 1.822 mg.g -1 And in the S1 sample, the total concentration was only 0.019 mg.g -1 The method comprises the steps of carrying out a first treatment on the surface of the Luteolin content in the S9 sample is the highest and is 0.141 mg.g -1 The content of the S1 sample is the lowest, namely, only 0.041 mg.g -1 . Different chemical component contents of the dracocephalum heterophyllum are indicated that different habitats determine the component contents.
Conclusion 2
In the analysis method of 9 chemical components established by the invention, in terms of wavelength selection, detection wavelengths of 254, 280, 340, 360nm and the like are selected for analysis, the maximum absorption wavelengths of the 9 selected chemical components are different, and the detection wavelengths are comprehensively considered, and 340nm with larger absorption are selected as the detection wavelengths.
Tan Jinhua et al in the "Programming" of quality standards for Qinghai Heterophylla suggest that the rosmarinic acid content in the dried product of Qinghai Heterophylla is not less than 0.5% (i.e. 5 mg. G) -1 ) 10 batches of samples used in the experiment except for the total S1 batch of samples, the rosmarinic acid content of 3.455 mg.g -1 The rest of the components reach the standard; zhao Lin it is recommended in quality standard researches on cymbidium sinense that the content of luteolin in the dried cymbidium sinense is not less than 0.03% (i.e. 0.3 mg.g) -1 ) The contents of luteolin in the decolourized S1, the portal S9 and the humus S10 in 10 batches of samples are respectively 0.170 mg.g -1 、0.233mg·g -1 、0.282mg·g -1 The content of luteolin in the rest 7 batches of the dracocephalum heterophyllum all reach the standard. Environmental factors are important factors affecting plant growth and secondary metabolite accumulation, and it is presumed that the difference of chemical component contents in 10 batches of samples is mainly caused by large difference of elevation and habitat of growing places.
The invention establishes a UPLC content determination method for 9 chemical components in the dracocephalum heterophyllum, and the method has the advantages of simple operation, reliable result and good repeatability, and can provide a certain reference for determining the content of the chemical components in the dracocephalum heterophyllum and perfecting the existing quality standard.
Example 2
The search experiment was performed on the conditions of ultra-high performance liquid chromatography for simultaneously measuring 9 chemical components in the dracocephalum heterophyllum: using ZORBOX SB-C18 chromatographic column with 0.1% formic acid-methanol (A) -0.1% formic acid water solution (B) as mobile phase, and the specification of the chromatographic column is 4.6X100 mm,1.8 μm, and flow rate is 0.3 mL-min -1 The elution program parameters of the ultra-high liquid chromatography are adjusted under the conditions of the detection wavelength of 340nm, the column temperature of 35 ℃ and the sample injection amount of 2 mu L, the solution (S1) of the test sample of the dracocephalum heterophyllum is measured respectively, the elution program is compared between No. 1 and No. 3, the elution program is carried out according to the invention, and the specific parameter adjustment is shown in the table 4.
Table 4 ultra high performance liquid chromatography elution procedure parameter exploration
| Sequence number | Retention time (minutes) | Mobile phase (vol%) | Correspondence spectrogram |
| 1 | 0-10-15-25-35-40-50-55 | 10-10-25-40-60-80-100-100％A | FIG. 2 |
| 2 | 0-10-20-30-40-50-55 | 25-25-35-50-70-100-100％A | FIG. 3 |
| 3 | 0-10-20-21-35-37-45-55-57-60 | 25-25-35-38-45-45-60-90-100-100％A | FIG. 4 |
| 4 | 0-15-25-26-40-42-50-60-62-65 | 25-25-35-38-45-45-60-90-100-100％A | FIG. 5 |
As can be seen from Table 4, in FIGS. 2 to 4, the peak 7 in the sample was co-eluted with the preceding peak to form a single peak, and the separation was not achieved, whereas the peak 7 in FIG. 5 was separated from the preceding peak by the baseline.
Peak 4 in fig. 2 and 4 was also co-eluted with the previous chromatographic peak, and peak 4 in fig. 5 was significantly separated from the previous peak and could be used for quantitative analysis.
Claims (9)
1. A method for simultaneously measuring a plurality of chemical components in the dracocephalum heterophyllum is characterized in that the chemical components of the dracocephalum heterophyllum are measured by adopting ultra-high performance liquid chromatography, and the chemical components at least comprise neochlorogenic acid, cryptochlorogenic acid and geraniin-7-O-glucuronide;
the detection conditions of the ultra-high performance liquid chromatography include:
chromatographic column stationary phase: diisobutyl is bonded to the silica gel surface through siloxane;
mobile phase A is selected from methanol or acid-containing methanol, mobile phase B is selected from water or acid-containing aqueous solution;
gradient elution is adopted, and the gradient elution program of the first 60min is as follows:
0-15min，25％-25％A；15-25min，25％-35％A；25-26min，35％-38％A；26-40min，38％-45％A；40-42min，45％-45％A；42-50min，45％-60％A；50-60min，60％-90％A。
2. the method of claim 1, wherein the chromatographic column is Agilent ZORBOX SB-C18.
3. The method of claim 1, wherein mobile phase a is methanol containing 0.1-0.3% formic acid and mobile phase B is 0.1-0.3% formic acid in water.
4. The method of claim 1, wherein the gradient elution procedure further comprises: 60-62min,90% -100% of A;62-65min,100% -100% A.
5. The method of claim 1, wherein the conditions of the ultra-high performance liquid chromatography further comprise one or more of the following i-iv:
i specification of chromatographic column: 4.6X100 mm,1-5 μm;
ii column temperature: 30-40 ℃;
iii flow rate: 0.1-0.5 mL/min -1 ；
iv detection wavelength: 210-360nm.
6. The method of claim 5, wherein the conditions of the ultra-high performance liquid chromatography further comprise one or more of the following i-iv:
i specification of chromatographic column: 4.6X100 mm,1.8 μm;
ii column temperature: 35 ℃;
iii flow rate: 0.3mL min -1 ；
iv detection wavelength: 340nm.
7. The method of claim 1, wherein the chemical composition further comprises chlorogenic acid, acteoside, luteolin, rosmarinic acid, quercetin, or luteolin.
8. The method according to claim 1, wherein the method for preparing the sample solution comprises: extracting a sample to be detected by using 70-80% methanol, filtering, and filtering the filtrate by a filter membrane to obtain a sample solution.
9. The method of claim 8, wherein the concentration of methanol is 75%.
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