CN108956800A - The measuring method of ellagic acid content in cortex moutan - Google Patents
The measuring method of ellagic acid content in cortex moutan Download PDFInfo
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Abstract
The present invention relates to the measuring methods of ellagic acid content in field of traditional Chinese medicine technology cortex moutan: taking cortex moutan medicinal material, is extracted using methanol hydrochloride solution, filters, take subsequent filtrate；Subsequent filtrate injects liquid chromatograph, Detection wavelength 253nm, with the content of ellagic acid in external standard method or calibration curve method measurement test solution.The method of the present invention is easy to operate, and step is simple, provides certain theoretical foundation for the further development and utilization of Chinese medicine cortex moutan.
Description
Technical field
The present invention relates to field of traditional Chinese medicine technology, in particular to the measuring method of ellagic acid content in a kind of cortex moutan.
Background technique
Chinese medicine cortex moutan is the dry root skin of ranunculaceae peony Paeonia suffruticosa Andr., autumn
Root is excavated, radicula and silt is removed, strips root skin, dries or scrape off rough bark, core is removed, dries.Bitter, pungent, slightly cold, tool
There is the effect of clearing heat and cooling blood, activating microcirculation and removing stasis medicinal and clearing liver-fire, enters ying blood for heat, febrile virulent maculae, hematemesis and epistaxis, night fever abating at dawn,
Lossless hectic fever due to yin, amenorrhea and algomenorrhea, the pain of injury caused by falling and tumbling, carbuncle sore tumefacting virus.
Cortex moutan complex chemical composition, Zhao Wenjun etc. are analyzed it using HPLC-QTOFMS technology, identify 48 altogether
A compound [pharmacy practice magazine, 2014,32 (4): 261-265], Hu Yunfei etc. is using UPLC-Q-TOF-MS technology to difference
The difference of place of production cortex moutan medicinal material chemical component is studied, identify altogether 37 compounds [Chinese herbal medicine, 2016,47 (17):
2984-2992], it mainly include phenylacetyl class (Paeonol, root bark of tree peony phenolic glycoside, Paeonol original glycosides and the new glycosides of Paeonol etc.), monoterpene (Chinese herbaceous peony
Medicine glycosides, oxypaeoniflorin and benzoylpaeoniflorin etc.), phenolic acid (benzoic acid, gallic acid, gallicin), nutgall acyl
Glycoside (glucopyranose gallate and galloyl glucose etc.), flavonoids (catechin etc.).With calm, cooling,
The central inhibitory actions such as antipyretic, analgesia, spasmolysis, antiatherosclerosis, diuresis, antiulcer, anti-inflammatory, antivirus action, improvement
Alcoholic hepatitis inhibits lipopolysaccharide-induced inflammation, protection acute liver toxicity and improvement -4 phenyl -1,2,3,6- of 1- methyl
The effect of the Parkinson disease of tetrahydropyridine (MPTP) induction.
Positive brave wait there is not gallic acid, (+)-catechin, Paeoniflorin, the 1,2,3,4,6- five in cortex moutan using HPLC method
Infanticide acyl glucose and Paeonol have carried out assay [Chinese medicine, 2013,36 (3): 416-422], thank to the use such as sword beautiful jade
HPLC method is to gallic acid, oxypaeoniflorin, Paeoniflorin, the 1,2,3,4,6- Penta-O-galloyl-D-glucopyranose, the root bark of tree peony in cortex moutan
Phenol, benzoylpaeoniflorin have carried out assay [Chinese experimental pharmacology of traditional Chinese medical formulae magazine, 2013,19 (2): 85-89], and Zhang Ronghua etc. is adopted
With UPLC method to gallic acid, 5 hydroxymethyl furfural, P-hydroxybenzoic acid, oxypaeoniflorin, Paeoniflorin, the benzene in cortex moutan
8 ingredients such as formic acid, 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranose, Paeonol have carried out assay [Guangdong pharmaceutical university
Journal, 2017,33 (3): 336-341].
There are no about containing the report of ellagic acid in the prior art in cortex moutan.
Summary of the invention
By studying for a long period of time, we have found to contain a kind of polyphenol dilactone in cortex moutan for the first time: 2,3,7,8-
Tetrahydroxy benzopyrano5,4,3-cdebenzopyran-5,10dione are commonly called as ellagic acid.Through HR-ESI-MS,
2DNMR technology determines that the structural formula of compound is as follows:
The object of the present invention is to provide ellagic acids in a kind of cortex moutan easy to operate, accuracy is high, reproducible to contain
Quantity measuring method.
What the present invention was obtained through the following steps:
The measuring method of ellagic acid content in a kind of cortex moutan, comprising the following steps:
(1) cortex moutan medicinal powder is taken, is extracted using methanol hydrochloride solution, filters, takes subsequent filtrate；
(2) subsequent filtrate injects liquid chromatograph, chromatographic condition: using octadecylsilane chemically bonded silica as filler；With second
Nitrile is mobile phase A, using the acid solution of Volume fraction 0.1~1% as Mobile phase B, using gradient elution mode: 0min →
12min, acetonitrile 3% → 15%；12min → 25min, acetonitrile 15% → 24%；Detection wavelength is 253nm, with external standard method or mark
Directrix curve method measures the content of ellagic acid in test solution.
The measuring method, hydrochloric acid percent by volume is greater than 2%, preferably 2% preferably in methanol hydrochloride solution.
The measuring method, preferably extracting method are to be heated to reflux 30 minutes~2 hours, preferably 1 hour.
The measuring method, the preferably mass volume ratio of cortex moutan medicinal powder and methanol hydrochloride solution be 0.1g~
0.5g:50mL, preferably 0.2g:50mL.
The measuring method, in preferred steps (1)
Test sample cortex moutan medicinal powder is taken, it is accurately weighed, it sets in round-bottomed flask, certain volume score ratio is added in precision
Methanol hydrochloride solution, weighed weight are heated to reflux 30 minutes~2 hours, let cool, then weighed weight, supplied and subtracted with Extraction solvent
The weight of mistake, shakes up, and filtration takes subsequent filtrate.It is preferred that cortex moutan medicinal powder crosses No. five sieves.
The measuring method, preferably using the sample volume of ellagic acid reference substance as abscissa, integrating peak areas value is vertical sits
Mark carries out linear regression, obtains regression equation y=9619272x-19673, correlation coefficient r=1.0000, x is sample volume, value
Range 0.0043 μ of μ g~0.086 g, y are peak area.
The measuring method, preferably sample recovery rate are 95.0%~105.0%.
The content assaying method, the acid solution in preferred steps (2) are that glacial acetic acid solution, formic acid solution or phosphoric acid are molten
Liquid.
The cortex moutan medicinal material is the dry root skin of ranunculaceae peony Paeonia suffruticosa Andr..
The gradient elution mode changes the component (ingredient, ionic strength etc.) or pH of eluent for gradient, with
The method that component different on chromatographic column is eluted out by the phase within reasonable time.
The utility model has the advantages that
1) the cortex moutan test solution stability of the method for the present invention preparation is good, and measured value is basicly stable for 24 hours；
2) for sample recovery rate in 95.0%~105.0% range, measurement numerical value can accurately reflect tan in crude drug
Spend the content of acid；
3) method is easy to operate, and step is simple, provides certain theory for the further development and utilization of Chinese medicine cortex moutan
Foundation.
Detailed description of the invention
Fig. 1 is ellagic acid uv absorption spectra；
Fig. 2 is the HPLC chromatogram of 2.3 lower ellagic acid reference substances of embodiment 1；
Fig. 3 is the HPLC chromatogram of 2.3 lower cortex moutan medicinal material test solutions of embodiment 1；
Fig. 4 is that (abscissa is sample volume to ellagic acid standard curve, and ordinate is peak area.
Specific embodiment
Below by way of specific embodiment, the present invention is further illustrated, not limitation of the invention, according to ability
The prior art well known to domain, embodiments of the present invention are not limited to specific embodiment.
Embodiment 1
1. instrument and reagent
Instrument: Sartorius CP225D electronic balance；Waters2695 high performance liquid chromatograph.
Reference substance is provided by National Institute for Food and Drugs Control, lot number: 111959-201602, content is in terms of 89.3%.
Reagent: acetonitrile, methanol are chromatographically pure, and water is the purified water of Millipore preparation, other reagents are that analysis is pure.
2. chromatographic condition
The preparation of 2.1 reference substance solutions: precision weighs ellagic acid reference substance 12.09mg, sets in 100ml measuring bottle, adds methanol
Scale is dissolved and be diluted to, is shaken up, as reference substance stock solution, then accurate measurement 1ml, sets in 25ml measuring bottle, adds methanol dilution
To scale, shake up to get the reference substance solution for being 4.3 μ g/ml to concentration.
The preparation of 2.2 test solutions: taking Tree peony Bark to be measured (crossing No. five sieves) 0.2g, accurately weighed, sets round bottom burning
In bottle, 2% methanol hydrochloride solution 50ml is added in precision, and weighed weight is heated to reflux 1 hour, lets cool, then weighed weight, with 2%
Methanol hydrochloride solution supplies the weight of less loss, shakes up, filtration to get.
2.3 chromatographic condition
Ellagic acid uv absorption spectra is shown in Fig. 1.Final choice 253nm is as measurement wavelength.
Chromatographic column: Agilent Eclipse Plus C18 (5 μm, 4.6mm × 250mm)；Using acetonitrile as mobile phase A, with
0.2% phosphoric acid solution is Mobile phase B, and the regulation according to the form below carries out gradient elution；Flow velocity 1.0mL/min, 35 DEG C of column temperature；Detection
Wavelength 253nm.Number of theoretical plate is calculated by ellagic acid peak should be not less than 5000.
Precision draws 2.1 lower reference substance solutions and 2.2 lower each 10 μ L of test solution, injects liquid chromatograph, into
Row measurement.As a result ellagic acid peak type is preferable, and number of theoretical plate, separating degree, symmetrical factor meet related request, it was demonstrated that the chromatostrip
Part is feasible.See Fig. 2,3.
3. the investigation of sample solution preparation method
The investigation of 3.1 Extraction solvents
The preparation of test solution: taking Tree peony Bark to be measured (crossing No. five sieves) 0.2g respectively, accurately weighed, sets round bottom burning
In bottle, methanol, 75% methanol, 50% methanol, 1% methanol hydrochloride solution, 2% methanol hydrochloride solution, 5% hydrochloric acid first is added in precision
Alcoholic solution 50ml, weighed weight are heated to reflux 1 hour, let cool, then weighed weight, and the weight of less loss is supplied with corresponding Extraction solvent
Amount, shake up, filtration to get.
It is accurate respectively to draw 2.1 lower reference substance solutions and each 10 μ L of above-mentioned test solution, liquid chromatograph is injected, into
Row measurement is calculated content and (is calculated with dry product: being measured through toluene method, 9.39%) methodological study cortex moutan moisture is.Knot
Fruit is shown in Table 1.
1 Extraction solvent of table investigates result
By measurement result it is found that using percent by volume greater than 2% methanol hydrochloride solution as Extraction solvent when target component
Chromatographic peak area is maximum, assay result highest, it is contemplated that the applicability of chromatographic column, select 2% methanol hydrochloride solution as
Extraction solvent.
The investigation of 3.2 extracting methods
Method one (ultrasonic extraction): taking Tree peony Bark to be measured (crossing No. five sieves) 0.2g respectively, accurately weighed, sets round bottom burning
In bottle, precision 2% methanol hydrochloride solution 50ml of addition, weighed weight, be ultrasonically treated (power 500W, frequency 40kHz) 30 minutes,
45 minutes, 1 hour, take out, then weighed weight is supplied the weight of less loss with 2% methanol hydrochloride solution, shaken up, filtration to get.
Method two (is heated to reflux): Tree peony Bark to be measured (crossing No. five sieves) 0.2g is taken respectively, it is accurately weighed, and set round bottom burning
In bottle, 2% methanol hydrochloride solution 50ml is added in precision, and weighed weight is heated to reflux 30 minutes, 1 hour, 2 hours, lets cool, then
Weighed weight is supplied the weight of less loss with 2% methanol hydrochloride solution, is shaken up, filtration to get.
It is accurate respectively to draw 2.1 lower reference substance solutions and 3.2 lower each 10 μ L of test solution, inject liquid chromatogram
Instrument is measured, and calculates content.It the results are shown in Table 2.
2 extracting mode of table and extraction time investigate result
| Extracting method | Content (mg/g) |
| Ultrasound 30 minutes | 0.74 |
| Ultrasound 45 minutes | 0.78 |
| Ultrasound 1 hour | 0.82 |
| It is heated to reflux 30 minutes | 0.92 |
| It is heated to reflux 1 hour | 1.14 |
| It is heated to reflux 2 hours | 1.14 |
According to 2 measurement result of table, heating and refluxing extraction efficiency is apparently higher than ultrasonic extraction.It is heated to reflux 1 hour or more, mentions
The basic indifference of result is taken, therefore selective extraction method is to be heated to reflux 1 hour.
The investigation of 3.3 sampling amounts
Tree peony Bark to be measured (crossing No. five sieves) 0.1g, 0.2g, 0.5g is taken respectively, it is accurately weighed, it sets in round-bottomed flask, essence
2% methanol hydrochloride solution 50ml of close addition, weighed weight is heated to reflux 1 hour, lets cool, then weighed weight, with 2% hydrochloric acid first
Alcoholic solution supplies the weight of less loss, shakes up, filtration to get.
It is accurate respectively to draw 2.1 each 10 μ L of lower test solution of lower reference substance solution grade 3.3, inject liquid chromatogram
Instrument is measured, and calculates content.It the results are shown in Table 3.
3 sampling amount of table investigates result
| Sampling amount | Content (mg/g) |
| 0.1024g | 1.16 |
| 0.2006g | 1.14 |
| 0.5021g | 1.02 |
As can be seen from the above results measurement result is relatively low when sampling amount is 0.5021g, in addition two kinds of sampling amount measurement results do not have
There is significant difference.In order to ensure the uniformity of sampling, determine that sampling amount is 0.2g.
The preparation of 3.4 test solutions
In conclusion test solution the preparation method is as follows: take Tree peony Bark to be measured (cross No. five sieve) 0.2g, it is accurate
It is weighed, it sets in round-bottomed flask, 2% methanol hydrochloride solution 50ml is added in precision, and weighed weight is heated to reflux 1 hour, lets cool, then
Weighed weight is supplied the weight of less loss with 2% methanol hydrochloride solution, is shaken up, filtration to get.
4. the investigation of linear relationship
2.1 lower reference substance solutions are taken, it is accurate respectively to draw each 1,2,5,10,15,20 μ L, liquid chromatograph is injected, point
It Ce Ding not integrating peak areas value.Using the sample volume of ellagic acid reference substance as abscissa, integrating peak areas value is ordinate, carries out line
Property return, obtain regression equation.Measurement result is shown in Table 4.
4 linear relationship of table investigates result
| Sampling volume (μ L) | Concentration (μ g/mL) | Sample volume (μ g) | Peak area |
| 1 | 4.3 | 0.0043 | 22105 |
| 2 | 4.3 | 0.0086 | 63594 |
| 5 | 4.3 | 0.0215 | 187353 |
| 10 | 4.3 | 0.0430 | 392335 |
| 15 | 4.3 | 0.0645 | 599848 |
| 20 | 4.3 | 0.0860 | 808958 |
Regression equation y=9619272x-19673, correlation coefficient r=1.0000.X is sample volume, value range 0.0043
~
0.0860 μ g, y is peak area.
Test result shows that ellagic acid sample volume sample volume between 0.0043~0.0860 μ g with integrating peak areas value is in
Good linear relationship.See Fig. 4.
5. instrument precision is tested
Precision draws 2.1 lower 10 μ L of reference substance solution, injects liquid chromatograph, continuous sample introduction 6 times, surveys its peak area product
Score value.It the results are shown in Table 5.
5 Precision test result of table
Test result display instrument precision is good.
6. sample stability is tested
The preparation of test solution: taking Tree peony Bark to be measured (crossing No. five sieves) about 0.2g, accurately weighed, according under 3.4
Test solution is made in method.It is accurate for 24 hours to draw 10 μ L respectively in 0h, 4h, 8h, 12h, 16h, 20h, liquid chromatograph is injected,
Peak area is recorded, the relative standard deviation (RSD) of peak area is calculated, the results are shown in Table 6.
6 Precision test result of table
The result shows that in test solution ellagic acid be placed at room temperature for 24 hours it is interior basicly stable.
7. detection limit and quantitative limit
The ellagic acid reference substance solution for preparing a low concentration respectively, injects liquid chromatograph, calculates its peak height and base
The ratio (i.e. signal-to-noise ratio S/N) of line noise, as S/N=3, sample volume at this time limits (LDQ) as the detection of method；Work as S/N
When=10, quantitative limit (LOQ) of the sample volume as method at this time, LDQ=0.215ng, the LOQ=0.645ng of ellagic acid are shown in
Table 7.
The detection of table 7 limit and quantitative limit testing result
| Sample introduction concentration (μ g/mL) | Signal-to-noise ratio (S/N) | Sampling volume (μ L) | Detection limit (ng) | Quantitative limit (ng) |
| 0.0215 | 3 | 10 | 0.215 | / |
| 0.0645 | 10 | 10 | / | 0.645 |
8. method repeatability is investigated
The preparation of test solution: taking Tree peony Bark to be measured (crossing No. five sieves) about 0.2g, accurately weighed, according under 3.4
Test solution is made in method, parallel 6 parts of preparation.
The accurate reference substance solution and each 10 μ L of above-mentioned test solution drawn under 2.1 respectively, injects liquid chromatograph,
It is measured, calculates content.It the results are shown in Table 8.
8 repeatability of table investigates result
6 parts of sample measurement result RSD≤2.0% show that the repeatability of content assaying method is good.
9. sample recovery rate is tested
The preparation of test solution: taking the Tree peony Bark 0.1g (ellagic acid content is 1.14mg/g) for having predicted content,
It is accurately weighed, it sets in round-bottomed flask, precision is added ellagic acid reference substance weak solution and (takes the ellagic acid reference substance deposit under 2.1
Liquid 5ml is set in 250ml measuring bottle, is diluted to scale with 2% methanol hydrochloride solution, is shaken up) 50ml, weighed weight is heated to reflux 1
Hour, let cool, then weighed weight, the weight of less loss supplied with 2% methanol hydrochloride solution, is shaken up, filtration to get.Parallel preparation
6 parts.
The accurate reference substance solution and each 10 μ L of above-mentioned test solution drawn under 2.1 respectively, injects liquid chromatograph,
It is measured, calculates content.It the results are shown in Table 9.
9 sample recovery rate of table investigates result
For 6 parts of sample pipetting volume rate of recovery average values in 95.0%~105.0% range, RSD≤2.0% shows measurement side
The rate of recovery of method is good.
10. sample measures
According to 3.4 lower section legal system available test sample solutions, collected 10 batches of samples are measured, the results are shown in Table
10。
10 sample size measurement result (being calculated according to dry product) of table
| Number | The place of production | Content (mg/g) |
| 1 | Shandong | 1.14 |
| 2 | Shandong | 0.92 |
| 3 | Henan | 0.84 |
| 4 | Henan | 0.94 |
| 5 | Henan | 1.03 |
| 6 | Shandong | 0.88 |
| 7 | Henan | 0.84 |
| 8 | Shandong | 0.92 |
| 9 | Henan | 0.94 |
| 10 | Shandong | 0.90 |
| 11 | Shandong | 0.84 |
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by the limit of embodiment
System, other any changes made without departing from the spirit and principles of the present invention, modification, combination, substitution, simplification should be
Equivalence replacement mode, is included within the scope of the present invention.
Claims (10)
1. the measuring method of ellagic acid content in a kind of cortex moutan, it is characterised in that the following steps are included:
(1) cortex moutan medicinal powder is taken, is extracted using methanol hydrochloride solution, filters, takes subsequent filtrate；
(2) subsequent filtrate injects liquid chromatograph, chromatographic condition: using octadecylsilane chemically bonded silica as filler；It is with acetonitrile
Mobile phase A, using the acid solution of Volume fraction 0.1~1% as Mobile phase B, using gradient elution mode: 0min → 12min, second
Nitrile 3% → 15%；12min → 25min, acetonitrile 15% → 24%；Detection wavelength is 253nm, with external standard method or calibration curve method
Measure the content of ellagic acid in test solution.
2. measuring method according to claim 1, it is characterised in that hydrochloric acid percent by volume is greater than in methanol hydrochloride solution
2%。
3. measuring method according to claim 1, it is characterised in that extracting method is to be heated to reflux 30 minutes~2 hours.
4. measuring method according to claim 1, it is characterised in that the matter of cortex moutan medicinal powder and methanol hydrochloride solution
Amount volume ratio is 0.1g~0.5g:50mL.
5. measuring method according to claim 1, it is characterised in that in step (1)
Test sample cortex moutan medicinal powder is taken, it is accurately weighed, it sets in round-bottomed flask, the hydrochloric acid of certain volume score ratio is added in precision
Methanol solution, weighed weight are heated to reflux 30 minutes~2 hours, let cool, then weighed weight, supply less loss with Extraction solvent
Weight shakes up, and filtration takes subsequent filtrate.
6. measuring method according to claim 1, it is characterised in that using the sample volume of ellagic acid reference substance as abscissa, peak
Area integral value is ordinate, carries out linear regression, obtains the x-19673 of regression equation y=9619272, correlation coefficient r=
1.0000, x be sample volume, and value range 0.0043 μ of μ g~0.086 g, y are peak area.
7. measuring method according to claim 1, it is characterised in that Extraction solvent is percent by volume 2% in step (1)
Methanol hydrochloride solution.
8. measuring method according to claim 1, it is characterised in that extracting method is to be heated to reflux 1 hour in step (1).
9. measuring method according to claim 1, it is characterised in that sample recovery rate is 95.0%~105.0%.
10. content assaying method according to claim 1, it is characterised in that the acid solution in step (2) is that glacial acetic acid is molten
Liquid, formic acid solution or phosphoric acid solution.
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