CN117213385A - Method for detecting and quantifying An Zhuokui Nol in Antrodia camphorata solid state fermentation product - Google Patents
Method for detecting and quantifying An Zhuokui Nol in Antrodia camphorata solid state fermentation product Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 39
- 241001486992 Taiwanofungus camphoratus Species 0.000 title claims abstract description 34
- 238000010563 solid-state fermentation Methods 0.000 title claims abstract description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004811 liquid chromatography Methods 0.000 claims abstract description 14
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 17
- 238000001514 detection method Methods 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000012224 working solution Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 6
- 238000002137 ultrasound extraction Methods 0.000 claims description 6
- 238000010829 isocratic elution Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 7
- 238000005259 measurement Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 2
- 239000011550 stock solution Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
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- -1 triterpene compounds Chemical class 0.000 description 2
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 1
- 240000008397 Ganoderma lucidum Species 0.000 description 1
- 235000001637 Ganoderma lucidum Nutrition 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
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- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 230000036039 immunity Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
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- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
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- 238000013112 stability test Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 150000003669 ubiquinones Chemical class 0.000 description 1
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- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention relates to the technical field of material content measurement, in particular to a method for detecting and quantifying An Zhuokui Noel in Antrodia camphorate solid state fermentation products. Specifically, the invention relates to a method for detecting An Zhuokui Nol in Antrodia camphorate solid state fermentation product by liquid chromatography, wherein the chromatographic conditions of the liquid chromatography comprise: chromatographic column: c18 reverse phase chromatography column; mobile phase a:0.1% -1.0% trifluoroacetic acid aqueous solution; mobile phase B: acetonitrile, wherein the volume ratio of mobile phase A to mobile phase B is 10-30:70-90. The method further comprises establishing a standard curve of An Zhuokui Nol concentration and quantifying An Zhuokui Nol in Antrodia camphorate solid state fermentation. The determination method has the advantages of simplicity and convenience in operation, good repeatability, accuracy and the like; the recovery rate of An Zhuokui Noel is 96.28-103.42%.
Description
Technical Field
The invention relates to the technical field of material content measurement, in particular to a method for detecting and quantifying An Zhuokui Noel in Antrodia camphorate solid state fermentation products.
Background
Antrodia camphorata, also known as Antrodia camphorata or Antrodia camphorata, is also known as Ganoderma lucidum, and is known as Xuezhi (Antrodia camphorata), and the growing area is mainly between Taiwan mountain forests, and only grows on the inner wall of the core material of the special Antrodia camphorata trunk decay of Taiwan, or withers the wet surface of the lodged Antrodia camphorata wood. The pharmacological functions of the compound can resist tumors, protect livers, inhibit liver cancers, regulate immunity, resist inflammation, resist fatigue and the like, and various functional active substances are developed.
In recent years, many researches find that Antrodia camphorata is rich in various medicinal chemical components, wherein triterpene compounds, active polysaccharide and ubiquinone compounds are important functional active components of Antrodia camphorata. The ubiquinone compound in Antrodia camphorata is mainly An Zhuokui Nol and derivatives thereof, has anticancer effect, and is a source of main functional components in the development of Antrodia camphorata medicines at present.
Along with the gradual development of the application of Antrodia camphorata, the method is established for the liquid chromatography determination of An Zhuokui Nol in the Antrodia camphorata solid state fermentation product.
Disclosure of Invention
The invention provides a method for measuring An Zhuokui Nol content, which is accurate in analysis and simple and convenient in operation, for solving the problem of measuring An Zhuokui Nol in Antrodia camphorata solid-state fermentation products, and the accurate measurement of An Zhuokui Nol content is realized.
In order to achieve the above object, the present invention provides a method for detecting An Zhuokui nul in a solid state fermentation product of Antrodia camphorate by liquid chromatography, wherein the chromatographic conditions of the liquid chromatography include:
chromatographic column: c18 reverse phase chromatography column; mobile phase a:0.1 to 1.0 percent of trifluoroacetic acid aqueous solution; mobile phase B: acetonitrile, wherein the volume ratio of mobile phase A to mobile phase B is 10-30:70-90.
Further, the specification of the C18 reverse-phase chromatography column was 5 μm, 4.6mm×250mm.
In the process of the detection, the experimental result shows that the An Zhuokui Noel chromatographic peak capacity factor is reduced along with the increase of the acetonitrile proportion of the mobile phase B, and the An Zhuokui Noel chromatographic performance is the best when the trifluoroacetic acid content in the mobile phase A is 0.5 percent. Thus, further, the mobile phase a was a 0.5% aqueous trifluoroacetic acid solution. Further, the volume ratio of mobile phase A to mobile phase B was 20:80.
Further, the chromatographic conditions of the liquid chromatography further include: the elution procedure is isocratic elution for 5-30 min; the detection wavelength is 190-800 nm; the flow rate is 0.8-1.2 ml/min; the column temperature is 20-40 ℃; the sample injection amount is 5-20 mu l.
Further, the elution procedure was isocratic for 16min.
Further, the detection wavelength was 266nm.
Further, the flow rate was 1.0mL/min.
Further, the column temperature was 30 ℃.
Further, the sample amount was 20. Mu.l.
Further, the method further comprises: preparing a sample to-be-detected liquid: mixing an Antrodia camphorate solid state fermentation product powder sample with an organic solvent, and performing ultrasonic extraction and filtration treatment to obtain a sample to-be-detected liquid; and then detecting the sample to-be-detected liquid by adopting the chromatographic conditions through liquid chromatography.
Further, the organic solvent comprises methanol, acetonitrile or 95% ethanol. Preferably, the organic solvent is 95% ethanol.
Further, the ultrasonic extraction time is 30-120 min, preferably 90min.
Further, the filtration treatment adopts a microporous filter membrane, and the pore diameter of the microporous filter membrane is 0.45 mu m.
Further, the mixed solution of the Antrodia camphorate solid state fermentation product powder sample and the organic solvent is subjected to ultrasonic extraction and then is subjected to filtration treatment, and the organic solvent is preferably adopted for constant volume, shaking and standing treatment.
Further, the method also comprises the step of quantifying An Zhuokui Nol in the Antrodia camphorate solid state fermentation product, wherein the quantifying comprises the following steps:
preparation of a standard working solution: mixing An Zhuokui Noll standard substance and organic solvent to prepare standard working solution with different required concentrations;
detecting the standard working solution by adopting the chromatographic conditions through liquid chromatography to establish a standard curve of An Zhuokui Nol concentration;
and obtaining the An Zhuokui Nol content in the Antrodia camphorata solid state fermentation product from the An Zhuokui Nol liquid chromatography detection result in the Antrodia camphorata solid state fermentation product based on the standard curve.
Further, the organic solvent comprises methanol, acetonitrile or 95% ethanol.
Further, the standard working solution is prepared by mixing An Zhuokui Noel standard substance and organic solvent to obtain standard stock solution, and diluting the standard stock solution with the organic solvent to prepare standard working solution with different required concentrations.
Further, the purity of the An Zhuokui Noel standard is more than or equal to 98 percent.
Further, the concentration of the standard stock solution c= An Zhuokui nular standard mass m× An Zhuokui nular standard purity per 100V; wherein, the unit of C is μg/mL, the unit of m is g, and the unit of V is mL.
Further, the concentration of the standard working solution is 2.047-10.237 mug/mL.
Further, the standard working fluid had 5 concentrations of 2.047 μg/mL, 4.095 μg/mL, 6.142 μg/mL, 8.190 μg/mL, and 10.237 μg/mL, respectively.
Preferably, the standard curve equation in step 2) is y=36.1541x+0.3180, r 2 =0.9999; wherein x is the concentration of An Zhuokui Noel standard solution, and y is the measured peak surfaceAnd (3) accumulation.
Preferably, in step 4), an Zhuokui Nol concentration in the sample to be detected is obtained according to a standard curve equation and the measured peak area, and then An Zhuokui Nol content in the sample is obtained according to An Zhuokui Nol concentration; the formula for obtaining An Zhuokui Nol content in the sample from An Zhuokui Nol concentration in the sample to-be-detected liquid is An Zhuokui Nol content X= An Zhuokui Nol concentration C×constant volume V/mass m in the sample to-be-detected liquid; wherein, the unit of X is mg/kg, the unit of C is mug/mL, the unit of V is mL, and the unit of m is g.
The invention has the beneficial effects that:
1) The determination method has the advantages of simplicity and convenience in operation, good repeatability, high accuracy and the like.
2) The measuring method has good repeatability and reproducibility, and the relative deviation of 6 parallel measuring results is not more than 5 percent when repeated measurement is carried out under the same condition.
Drawings
FIG. 1 is a standard graph of An Zhuokui Noel for example 1;
FIG. 2 is a chromatogram of the standard working fluid of example 1;
FIG. 3 is a spectral scan of the An Zhuokui Noll standard of example 1;
fig. 4 is a chromatogram of a An Zhuokui noor powder sample of example 1.
Fig. 5 is a chromatogram of a An Zhuokui noor powder sample of comparative example 1.
Detailed Description
The present invention is further illustrated below with reference to specific examples, which are not intended to limit the invention in any way. Unless specifically stated otherwise, the reagents, methods and apparatus employed in the present invention are those conventional in the art.
Example 1
0.01037g of An Zhuokui Nol standard with purity of 98.72% is placed in a 100mL volumetric flask, fully dissolved with 95% ethanol, diluted to a scale, and fully shaken to obtain a standard stock solution with concentration of 102.3726 mug/mL. Respectively taking 2mL, 4mL, 6mL, 8mL and 10mL of standard stock solution in a 100mL volumetric flask, and respectively diluting with 95% ethanol to constant volume to obtain standard working solutions with the concentrations of 2.047 mug/mL, 4.095 mug/mL, 6.142 mug/mL, 8.190 mug/mL and 10.237 mug/mL.
Injecting the standard working solutions with different concentrations into a liquid chromatograph for testing, wherein the chromatographic column is a YMC-Pack ODS-AQ (5 μm, 4.6mm×250 mm) reverse chromatographic column; the detector is an ultraviolet detector, the wavelength: 266nm; mobile phase: 0.5% aqueous trifluoroacetic acid/acetonitrile=20/80 isocratic elution; flow rate: 1.0mL/min; column temperature: 30 ℃; sample injection amount: 20. Mu.L.
Peak areas of 75.981, 146.670, 221.250, 295.730 and 371.600, respectively, were measured for standard working fluids at concentrations of 2.047 μg/mL, 4.095 μg/mL, 6.142 μg/mL, 8.190 μg/mL and 10.237 μg/mL, as shown in table 1.
Table 1: system stability test results
Regression analysis is carried out according to the concentration of An Zhuokui Noel standard working solution and the peak area corresponding to the concentration, so as to obtain a standard curve equation: y=36.1541x+0.3180, r 2 =0.9999; where x is the concentration of An Zhuokui Noll standard solution and y is the measured peak area. The An Zhuokui noor standard graph thus established is shown in fig. 1.
The chromatogram of An Zhuokui Noel standard working solution is shown in FIG. 2, and the retention time of the standard substance is stable from the chromatogram results. A spectroscopic scan of An Zhuokui noor standard is shown in figure 3.
And (3) carrying out ultrasonic extraction on 1.0686g of Antrodia camphorate solid state fermentation product powder sample by using 95% ethanol for 90min, cooling to room temperature, fixing the volume to the scale by using 95% ethanol, shaking uniformly, standing, and filtering by using a 0.45 mu m microporous filter membrane to obtain a sample to-be-detected liquid. And (3) injecting the sample to-be-detected liquid into the liquid chromatograph, and detecting the sample to-be-detected liquid by using the liquid chromatograph, wherein an obtained chromatogram is shown in fig. 4, and the chromatogram results show that the retention time is moderate, the separation effect is good, and no impurity peak interference exists.
According to a standard curve, an Zhuokui Nol concentration of the sample to be detected is 4.194 mug/mL, and An Zhuokui Nol content is 98.13mg/kg according to a An Zhuokui Nol content and concentration formula.
Example 2
The method comprises the steps of adding sample blanks with minimum acceptable concentration by a blank marking method, performing pretreatment according to a detection method, testing 10 obtained sample liquids according to the instrument conditions, wherein the concentration corresponding to the average value of the sample blanks and the standard deviation of 3 times is the detection limit LOD, the concentration corresponding to the LOD of 3 times is the quantitative limit LOQ, the result is shown in a table 2, the sample content is far higher than the detection limit and the quantitative limit, and the detection limit and the quantitative limit are available.
Table 2: method detection limit, quantitative limit measurement result
Example 3
The same Antrodia camphorate solid state ferment powder sample was subjected to repeated test and test reproducibility at different times according to the method of example 1, and the results are shown in Table 3.
Table 3: repeatability and reproducibility test results
As shown in Table 3, the same Antrodia camphorata solid state fermentation powder sample is repeatedly measured for 6 times, the RSD is respectively 3.23% and 0.72%, and the result shows that the method provided by the invention has good repeatability. The same Antrodia camphorate solid state ferment powder sample is measured again at different times, the relative deviation is 0.98%, and the result shows that the method has good reproducibility.
Example 4
6 samples were prepared as in example 1 at 20mg/kg and 75mg/kg, respectively, with average recovery rates of 96.28% and 103.42%, RSD of 3.42% and 2.03% (n=6), respectively, and the results are shown in table 4, and the results indicate that An Zhuokui nul recovery rate is between 96.28 and 103.42%, and the measurement results are accurate and reliable.
Table 4: recovery experiment (n=6)
Comparative example 1:
an Zhuokui nool in the sample test solution was tested according to the method in example 1 using the following chromatographic conditions:
the chromatographic column is a YMC-Pack ODS-AQ (5 μm, 4.6 mm. Times.250 mm) reverse chromatographic column; the detector is an ultraviolet detector, the wavelength: 266nm; mobile phase: 0.5% aqueous acetic acid/acetonitrile=20/80; isocratic elution for 30min; flow rate: 1.0mL/min; column temperature: 30 ℃; sample injection amount: 20. Mu.L.
The results are shown in FIG. 5, and it can be seen from the graph that An Zhuokui Nol has a retention time of 21.367 and that there is a formant interference.
The recovery of the spiked An Zhuokui noor was determined according to the method of example 4 using the chromatographic conditions of this comparative example, and the results are shown in table 5, which shows that the An Zhuokui noor recovery is less than 80% and that the interference of the miscellaneous peaks reduces the accuracy of the detection under the chromatographic conditions of this comparative example.
Table 5: recovery experiment (n=3)
It should be noted that the description of the present invention and the accompanying drawings illustrate preferred embodiments of the present invention, but the present invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein, which are not to be construed as additional limitations of the invention, but are provided for a more thorough understanding of the present invention. The above-described features are further combined with each other to form various embodiments not listed above, and are considered to be the scope of the present invention described in the specification; further, modifications and variations of the present invention may be apparent to those skilled in the art in light of the foregoing teachings, and all such modifications and variations are intended to be included within the scope of this invention as defined in the appended claims.
Claims (10)
1. A method for detecting An Zhuokui nul in Antrodia camphorate solid state fermentation by liquid chromatography, wherein the chromatographic conditions of the liquid chromatography comprise:
chromatographic column: c18 reverse phase chromatography column;
mobile phase a:0.1% -1.0% trifluoroacetic acid aqueous solution; mobile phase B: acetonitrile, wherein the volume ratio of mobile phase A to mobile phase B is 10-30:70-90.
2. The method of claim 1, wherein mobile phase a is a 0.5% aqueous trifluoroacetic acid solution and the volume ratio of mobile phase a to mobile phase B is 20:80.
3. The method of claim 1, wherein the chromatographic conditions of the liquid chromatograph further comprise: the elution procedure is isocratic elution for 5-30 min; the detection wavelength is 190-800 nm; the flow rate is 0.8-1.2 ml/min; the column temperature is 20-40 ℃; the sample injection amount is 5-20 μl.
4. A method according to claim 3, wherein the chromatographic conditions of the liquid chromatograph further comprise: the elution procedure is isocratic elution for 16min; the detection wavelength is 266nm; the flow rate is 1.0mL/min; the column temperature is 30 ℃; the sample loading was 20. Mu.l.
5. The method according to claim 1, wherein the method further comprises:
preparing a sample to-be-detected liquid: mixing an Antrodia camphorate solid state fermentation product powder sample with an organic solvent, and performing ultrasonic extraction and filtration treatment to obtain a sample to-be-detected liquid;
and then detecting the sample to-be-detected liquid by adopting the chromatographic conditions through liquid chromatography.
6. The method of claim 5, wherein the organic solvent comprises methanol, acetonitrile, or 95% ethanol.
7. The method of claim 5, wherein the time of ultrasonic extraction is 30-120 min.
8. The method of claim 5, wherein the filtration treatment employs a microporous filter membrane having a pore size of 0.45 μm.
9. The method according to any one of claims 1 to 8, further comprising quantifying An Zhuokui nul in a solid state fermentation of antrodia camphorate, the quantifying comprising the steps of:
preparation of a standard working solution: mixing An Zhuokui Noll standard substance and organic solvent to prepare standard working solution with different required concentrations;
detecting the standard working solution by adopting the chromatographic conditions through liquid chromatography to establish a standard curve of An Zhuokui Nol concentration;
and obtaining the An Zhuokui Nol content in the Antrodia camphorata solid state fermentation product from the An Zhuokui Nol liquid chromatography detection result in the Antrodia camphorata solid state fermentation product based on the standard curve.
10. The method of claim 9, wherein the organic solvent comprises methanol, acetonitrile, or 95% ethanol.
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