CN105974029B - Method that is a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure - Google Patents
Method that is a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure Download PDFInfo
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- CN105974029B CN105974029B CN201610542884.2A CN201610542884A CN105974029B CN 105974029 B CN105974029 B CN 105974029B CN 201610542884 A CN201610542884 A CN 201610542884A CN 105974029 B CN105974029 B CN 105974029B
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- 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
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- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N30/14—Preparation by elimination of some components
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- 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
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
Abstract
The invention discloses method that is a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure, six kinds of different structure iridoid glycoside constituents i.e. logaric acid in multi-arch retaining structure is detected based on DSPE HPLC methods simultaneously first, morroniside, loganin, chiratin, disconnected oxidation loganin, Secologanin dimethyl-acetal, 0.999 is all higher than using this method linearly dependent coefficient, detection is limited to 0.024 0.061 μ g/mL, each target component rate of recovery is between 92.7%~98.5%, relative standard deviation (RSD) is in the range of 0.85%~1.91%, it is few with consumption of organic solvent, purification and concentrated effect are good, the object rate of recovery is high, the features such as high sensitivity is easy to operate.The present invention has developed a set of fast and efficiently extraction, purification and analysis method for being adapted to iridoid methods of glycosides in the Chinese patent drug containing honeysuckle, for to further studying Chinese patent drug mechanism of action, establishing quality standard, medicinal material and related patent medicine quality controlled level are improved, instructs clinical practice significant.
Description
Technical field
The invention belongs to medicine analysis technical field, and in particular to a kind of to determine six kinds of cyclenes in multi-arch retaining structure simultaneously
The method of ether terpene methods of glycosides.
Background technology
Multi-arch retaining structure is the new drug examined during Severe Acute Respiratory Syndromes by national green passage in 2003, is in traditional Chinese medical science network disease
Under theoretical direction, draw ancient Chinese medicine medicine wisdom, with reference to it is modern it is antiviral, antibacterial, improve the achievement in research initiative such as immune and form
Chinese patent drug.Multi-arch retaining structure is national Chinese medicine protection kind, and its primary efficacy is antipyretic and detoxicated, and facilitaing lung expels the heat-evil.For controlling
Treat influenza category heat toxin and attack lung card, in recent years, Duo Jia scientific research institutions have carried out a large amount of scientific researches to multi-arch retaining structure,
Demonstrate its broad-spectrum disease resistance toxic action, especially to influenza A virus (H1N1, H3N2), avian influenza virus (H5N1, H9N2),
Influenza B virus, adenovirus, herpesviral etc. have compared with high inhibition killing action.In addition, this medicine can also effectively suppress
Various bacteria.Because its is evident in efficacy, national Chinese medicine protection kind has been put into it.2015, multi-arch retaining structure is granted to enter U.S.
State FDA carries out the second stage of clinical research.
Multi-arch retaining structure is with the capsule of weeping forsythia, honeysuckle, ephedra, stir-fry semen armeniacae amarae, gypsum, Radix Isatidis, thick wood-fern rhizome, fish raw meat
The pleasant impression drug matching of grass, Pogostemon cablin, rheum officinale, rhodiola root etc. ten is refined to be formed, and composition is relative complex, and product quality is by bulk drug shadow
Sound is very big.Therefore a set of appraisement system how is established, the Quality of Chinese Traditional Proprietary Medicine controlled levels such as multi-arch retaining structure are improved, for clinic
Using significant.
In multi-arch retaining structure, abundant iridoid glycosides compound is contained in the medicinal material such as honeysuckle, in recent years, no
It is disconnected that there are some researches prove iridoid glycosides compound has antiviral, antibacterial, anti-oxidant, hepatic cholagogic, antitumor, anti-inflammatory, increasing
The various active such as immune by force, therefore carry out the high efficiency extraction and analysis method to iridoid methods of glycosides in multi-arch retaining structure
Research, to further studying its mechanism of action, establishing quality standard, improve medicinal material and related patent medicine quality controlled level obviously has
It is significant.Yet with chemical composition species contained by multi-arch retaining structure is more, polarity difference is big, comprising flavones, organic
A variety of chemical compositions such as acid, iridoid glycoside, saponin(e;Meanwhile and process in pharmaceutic adjuvant use, cause its chemistry into
Divide increasingly complex.Therefore, with reference to the design feature of iridoid methods of glycosides, develop and be adapted to iridoid glycoside in honeysuckle patent medicine
The fast and efficiently extractions of constituents, purification and analysis method are urgently to be resolved hurrily.
The content of the invention
For above-mentioned the deficiencies in the prior art, the present invention provides a kind of while determines six kinds of cyclenes ether in multi-arch retaining structure
The method of terpene methods of glycosides, six kinds of iridoid glycosides are logaric acid, morroniside, loganin, chiratin, disconnected oxidation vomiting nut
The method of glycosides and Secologanin dimethyl-acetal, this method is easy to operate, sample purification effect is good, and analysis result is accurate
It is and reproducible.
To achieve the above object, the present invention adopts the following technical scheme that:
Method that is a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure, six kinds of cyclenes ethers of measure
Terpene methods of glycosides is logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin and Secologanin dimethyl second
Acetal, comprise the following steps that:
(1) multi-arch retaining structure traditional Chinese medicine powder is taken out, it is stand-by to weigh a certain amount of medicinal powder;
(2) Extraction solvent is added in the medicinal powder into step (1), ultrasonic extraction is carried out after shaking up and obtains supernatant;
(3) cleanser, eddy oscillating are added in the supernatant into step (2);
(4) supernatant after step (3) processing obtains extract solution with filtering with microporous membrane;
(5) precision weighs logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin, open union vomiting nut respectively
Glycosides dimethyl-acetal reference substance, 50% methanol is added to dissolve, it is 200 μ g/mL mixed standard solutions that concentration, which is made,;In use, press
Certain proportion dilutes step by step, stand-by.
(6) extract solution for obtaining step (4) carries out efficient liquid phase chromatographic analysis, and chromatographic condition is as follows:Chromatographic column:
Kromasil C18(4.6 × 250mm, 5 μm);Flow velocity:0.5-1.0mL/min;Detection wavelength:200-250nm;Column temperature:25-30
℃;Mobile phase:0.4% aqueous formic acid-acetonitrile, gradient elution;
(7) quantitative analysis of six kinds of iridoid glycoside constituents in multi-arch retaining structure is carried out with external standard method, i.e., with known
The chromatographic peak area of the iridoid glycosides of concentration compares its respective concentration and carries out regression analysis, obtains standard curve, to extraction
Liquid is measured, and is measured the chromatographic peak area of six kinds of iridoid glycoside constituents in detection extract solution, is substituted into standard curve, try to achieve
Logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin and Secologanin dimethyl in multi-arch retaining structure
The content of acetal.
Preferably, Extraction solvent is 50% ethanol in the step (2);The mass volume ratio of the medicinal powder and Extraction solvent
1g:30-50ml, it is further preferred that the mass volume ratio of the medicinal powder and Extraction solvent is 1g:40ml;
Preferably, the ultrasonic extraction time is 0.5-2min in the step (2), it is further preferred that the ultrasonic extraction time
For 1min;
Preferably, the cleanser added in the step (3) is diatomite and Mixture of Activated Carbon;It is further preferred that
The mass ratio of the diatomite and activated carbon is 90:10;
Preferably, the mass volume ratio of cleanser and supernatant described in the step (3) is 45-55g:1ml;Further
Preferably, the mass volume ratio of the cleanser and supernatant is 50g:1ml;
Preferably, the eddy oscillating time is 0.5-2min in the step (3);It is further preferred that the eddy oscillating
Time is 1min;
Preferably, miillpore filter specification is 0.22 μm in the step (4);
Preferably, flow velocity is 0.8mL/min in the step (6);Detection wavelength is 240nm;Column temperature:25℃;
Preferably, gradient elution program is as follows in the step (6):0~15min, 10%~14% acetonitrile;15~
35min, 14%~25% acetonitrile;35~45min, 25%~50% acetonitrile;45~50min, 50%~100% acetonitrile;50~
65min, 100% acetonitrile.
The invention also discloses the above method to carry out the application of quality evaluation to the Chinese patent drug of composition containing honeysuckle.
The present invention establishes dispersive solid-phase extraction-high performance liquid chromatography (DSPE-HPLC) method while detects Lian Huaqing first
Six kinds of different structure iridoid glycoside constituents are logaric acid, morroniside, loganin, chiratin, disconnected oxidation Strychnos nux-vomica in pest capsule
Sub- glycosides, Secologanin dimethyl-acetal, 0.999 is all higher than using this method linearly dependent coefficient, detection is limited to
0.024-0.061 μ g/mL, between 92.7%~98.5%, relative standard deviation (RSD) exists each target component rate of recovery
In the range of 0.85%~1.91%, the present invention is with consumption of organic solvent is few, purification and concentrated effect are good, the object rate of recovery
High, the features such as high sensitivity is easy to operate.
Instant invention overcomes the defects of prior art and condition limitation, to sample-pretreating method and instrument testing conditions
It is optimized, the present invention has the advantages that compared with prior art:
(1) present invention by six kinds of different structure iridoid glycoside constituents be logaric acid, morroniside, loganin, chiratin,
Disconnected oxidation loganin, Secologanin dimethyl-acetal pass through the pretreatment mode of dispersed solid phase processing, use simultaneously
High performance liquid chromatograph is measured, and greatlys save instrument and equipment and cost, can meet the work in different condition laboratory
Demand.
(2) inventive samples pre-treatment flow is simple, substantially reduces the detection time of each test sample, reduces point
Cost is analysed, effectively avoids dead adsorption phenomena from occurring, the present invention is used as pretreatment technology using dispersive solid-phase extraction (DSPE), reduces
The usage amount of organic solvent, shortens the pre-treatment time, makes experimental implementation easier, quick.
(3) present invention has detection sensitivity height, accurate and high repeatability and other advantages.
In a word, the present invention developed it is a set of be adapted to the Chinese patent drug containing honeysuckle in iridoid methods of glycosides it is quick, high
Extraction, purification and the analysis method of effect, for further research Chinese patent drug mechanism of action, establish quality standard, improve medicinal material and
Related patent medicine quality controlled level, instructs clinical practice significant.
Brief description of the drawings
Fig. 1 is the HPLC figures of mixing reference substance (A), multi-arch retaining structure extract (B);
Wherein, 1 is logaric acid chromatographic peak, and 2 be morroniside chromatographic peak, and 3 be loganin chromatographic peak, and 4 be chiratin chromatographic peak,
5 be disconnected oxidation loganin chromatographic peak, and 6 be Secologanin dimethyl-acetal chromatographic peak.
Embodiment
The present invention is further illustrated in conjunction with the embodiments, it should which explanation, the description below is merely to explain this
Invention, is not defined to its content.
Embodiment 1
Method that is a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure:
1 instrument and material
The type high performance liquid chromatographs of Agilent 1260, Agilent companies of the U.S.;KQ2400KDE type high power numerical controls surpass
Sonic apparatus, Kunshan Ultrasonic Instruments Co., Ltd.;R201 type Rotary Evaporators, Shensheng Science & Tech. Co., Ltd., Shanghai;BSA1245-
CW type precision balances, German Sartorius companies;Milli-Q (18.2M Ω) ultra-pure-water treatment system, U.S. Millipore are public
Department.
Methanol (chromatographically pure) is purchased from Tedia companies of the U.S.;Acetonitrile (chromatographically pure) is purchased from German Merck companies;Formic acid (chromatogram
It is pure) it is purchased from German Riedel companies;Remaining reagent is that analysis is pure, and experimental water is Milli-Q ultra-pure waters (18.2M Ω).Purchase
It is placed in Tianjin great Mao chemical reagent factories;Diatomite (chromatographic grade), activated carbon (chromatographic grade) polyamide (30~60 mesh, column chromatography) are equal
Purchase in Chemical Reagent Co., Ltd., Sinopharm Group.
Multi-arch retaining structure is purchased from Jinan City, Shandong Province and gargles the big pharmacy of the beautiful common people used by this experiment.6 kinds of iridoids
Glycoside compound reference substance (logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin, Secologanin dimethyl
Acetal) prepared by laboratory separation, structure is identified by spectral data, and areas of peak normalization method mass fraction is all higher than
98%.
2. prepared by sample extracting solution
Accurately weigh 1.0g multi-arch retaining structure samples to be placed in conical flask, add 50% ethanol 40mL, extract 1min,
2mL supernatants are taken, add cleanser diatomite-activated carbon (90: 10) 100mg, eddy oscillating 1min, after crossing 0.22 μm of filter membrane, take 3
μ L sample extract solutions, analyzed for HPLC.
3. the preparation of reference substance solution
Precision weighs logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin, Secologanin two respectively
Methyl acetal reference substance 2.0mg, is placed in 10mL brown volumetric flasks, adds 50% methanol to dissolve, constant volume, shakes up, concentration is made
For 200 μ g/mL mixed standard solutions.In use, dilute step by step in proportion, it is stand-by.
4. high-efficient liquid phase chromatogram condition
HPLC is analyzed, the μ L of sampling volume 3.Specifically chromatographic condition is:Kromasil C18Post (4.6mm × 250mm, 5 μm),
Mobile phase:0.4% aqueous formic acid-acetonitrile, gradient elution program:0~15min, 10%~14% acetonitrile;15~35min,
14%~25% acetonitrile;35~45min, 25%~50% acetonitrile;45~50min, 50%~100% acetonitrile;50~65min,
100% acetonitrile.Detection wavelength 240nm, flow velocity 0.8mL/min, 25 DEG C of column temperature.
5. measurement result calculates
The quantitative analysis of six kinds of iridoid glycoside constituents in multi-arch retaining structure is carried out with external standard method, i.e., with concentration known
Iridoid glycosides chromatographic peak area compare its respective concentration carry out regression analysis, obtain standard curve, extract solution entered
Row measure, the chromatographic peak area of six kinds of iridoid glycoside constituents in detection extract solution is measured, standard curve is substituted into, tries to achieve sample
Middle logaric acid, morroniside, loganin, chiratin, the disconnected content for aoxidizing loganin and Secologanin dimethyl-acetal.
Experimental result is as shown in table 1.
The measurement result of iridoid glycoside in the sample of table 1
6. methodological study
Under the condition determination of this research optimization, with each iridoid glycoside constituents in multi-arch retaining structure medicinal powder extract
Retention time and peak area be inspection target, the precision of this method, repeatability, stability and recovery of standard addition are entered respectively
Investigation is gone.Precision test shows, the RSD values of each iridoid glycoside constituents retention time are 0.45%~0.87%, peak
The RSD values of area are 0.71%~1.68%.Replica test shows, the RSD values of each iridoid glycoside constituents retention time
0.91% is below, the RSD values of peak area are below 3.93%.24h internal stabilities, which are tested, to be shown, each iridoid glycoside constituents
The RSD values of retention time are below 0.95%, and the RSD values of peak area are below 3.67%.Recovery of standard addition, which is tested, to be shown, each ring
Alkene ether terpene methods of glycosides recovery of standard addition is in 92.7%~98.5%, RSD values 0.85%~1.91%.Data above explanation,
This method has preferable precision, stability and reappearance, can be used for iridoid methods of glycosides in multi-arch retaining structure
Accurate Determining.
Embodiment 2
As described in Example 1, another multi-arch retaining structure sample 2 is selected, experimental result is shown in Table 2.
The measurement result of iridoid glycoside in the sample of table 2
Embodiment 3
As described in Example 1, another multi-arch retaining structure sample 3 is selected, experimental result is shown in Table 3.
The measurement result of iridoid glycoside in the sample of table 3
Although above-mentioned the embodiment of the present invention is described in conjunction with the embodiments, not the present invention is protected
The limitation of scope, one of ordinary skill in the art should be understood that on the basis of technical scheme, those skilled in the art
Various modifications or deformation that creative work can make need not be paid still within protection scope of the present invention.
Claims (13)
1. method that is a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure, it is characterised in that measure
Six kinds of iridoid glycoside constituents are logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin and open union kind respectively
Momordica cochinchiensis glycosides dimethyl-acetal, determination step are as follows:
(1)Multi-arch retaining structure traditional Chinese medicine powder is taken out, it is stand-by to weigh a certain amount of medicinal powder;
(2)To step(1)In medicinal powder in add Extraction solvent, after shaking up carry out ultrasonic extraction obtain supernatant;
(3)To step(2)In supernatant in add cleanser, eddy oscillating;
(4)Through step(3)Supernatant after processing obtains extract solution with filtering with microporous membrane;
(5)Precision weighs logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin, Secologanin two respectively
Methyl acetal reference substance, adds methanol to dissolve, mixed standard solution is made;In use, dilute step by step by a certain percentage, it is stand-by;
(6)By step(4)Obtained extract solution carries out efficient liquid phase chromatographic analysis, and chromatographic condition is as follows:Chromatographic column:Kromasil
C18, 4.6 × 250 mm, 5 μm;Flow velocity:0.5-1.0mL/min;Detection wavelength:200-250nm;Column temperature:25-30℃;Mobile phase:
0.4% aqueous formic acid-acetonitrile, gradient elution;
(7)The quantitative analysis of six kinds of iridoid glycoside constituents in multi-arch retaining structure is carried out with external standard method, i.e., with concentration known
Iridoid glycosides chromatographic peak area compare its respective concentration carry out regression analysis, obtain standard curve, extract solution entered
Row measure, the chromatographic peak area of six kinds of iridoid glycoside constituents in detection extract solution is measured, substitute into standard curve, the company's of trying to achieve flower
Logaric acid, morroniside, loganin, chiratin, disconnected oxidation loganin and the contracting of Secologanin dimethyl second in clear pest capsule
The content of aldehyde;
Wherein, the step(6)Middle gradient elution program is as follows:0~15 min, 10%~14% acetonitrile;15~35 min, 14%
~25% acetonitrile;35~45 min, 25%~50% acetonitrile;45~50 min, 50%~100% acetonitrile;50~65 min, 100% second
Nitrile.
2. method that is as claimed in claim 1 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the step(2)Middle Extraction solvent is 50% ethanol;The mass volume ratio 1g of the medicinal powder and Extraction solvent:
30-50ml。
3. method that is as claimed in claim 2 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the mass volume ratio of the medicinal powder and Extraction solvent is 1g:40ml.
4. method that is as claimed in claim 1 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the step(2)The middle ultrasonic extraction time is 0.5-2min.
5. method that is as claimed in claim 4 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the ultrasonic extraction time is 1min.
6. method that is as claimed in claim 1 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the step(3)The cleanser of middle addition is diatomite and Mixture of Activated Carbon.
7. method that is as claimed in claim 6 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the mass ratio of the diatomite and activated carbon is 90:10.
8. method that is as claimed in claim 1 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the step(3)Described in the mass volume ratio of cleanser and supernatant be 45-55 g:1ml.
9. method that is as claimed in claim 8 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the mass volume ratio of the cleanser and supernatant is 50 g:1ml.
10. method that is as claimed in claim 1 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the step(3)The middle eddy oscillating time is 0.5-2 min.
It is 11. as claimed in claim 10 a kind of while determine the side of six kinds of iridoid glycoside constituents in multi-arch retaining structure
Method, it is characterised in that the eddy oscillating time is 1 min.
12. method that is as claimed in claim 1 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the step(4)Middle miillpore filter specification is 0.22mm.
13. method that is as claimed in claim 1 a kind of while determining six kinds of iridoid glycoside constituents in multi-arch retaining structure,
Characterized in that, the step(6)Middle flow velocity is 0.8 mL/min;Detection wavelength is 240nm;Column temperature:25℃.
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