CN1420122A - Glycosides compound monomer in Chinese herbaceous peony, and method for extracting and separating same - Google Patents
Glycosides compound monomer in Chinese herbaceous peony, and method for extracting and separating same Download PDFInfo
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Abstract
A paeoniflorin monomer as a novel medicine is prepared from white (or red) peony through swelling in aqueous solution of alcohol, thermal reflux, concentrating, ultrasonic extracting in acetone solution, concentrating, mixing with gum powder, concentrating, vacuum chromatography, eluting, concentrating, separating by silica gel column, eluting and distribution chromatography. Its advantages are simple process, low cost and high yield.
Description
Technical field
The present invention relates to biomedicine field, glycoside compound monomer in specifically a kind of Chinese herbaceous peony, and extraction and isolating method.Glycoside compound monomer in the described Chinese herbaceous peony, comprise paeoniflorin monomer, peony lactone glucoside (albiflorin) monomer, Benzoylpaeoniflorin (benzoylpaeoniflorin) Dan Ti He Hydroxyalkyl base paeoniflorin (oxypaeoniflorin) monomer, wherein the paeoniflorin monomer content meets the purity requirement of a class plant kind new medicine more than 90%.
Background technology
The root of herbaceous peony or the radix paeoniae rubrathe are a kind of Chinese medicine commonly used, and clinical application has had history in several thousand, just classify middle product in Shennong's Herbal as, have flat liver pain relieving, nourishing blood for regulating menstruation, astringing YIN to stop sweating attack effect, main smelting headache is dizzy, hypochondriac pain, stomachache, four limbs contraction pain, deficiency of blood committee is yellow, menoxenia, spontaneous perspiration, night sweat.Research along with modern chemistry and pharmacology, its chemical ingredients and pharmacological action are all more clearly, but the main component paeoniflorin (paeoniflorin) in its glycoside compound has only the usefulness of standard substance for drug inspection, does not form the production of large-scale commercial.Existing one two kind new medicine is the extract of a Chinese herbaceous peony also, and it contains the Chinese herbaceous peony general glycoside greater than 50%.People such as Xu Shuyun once reported the extraction process (CN 88104779.9) of effective composition from white peony root, the root of herbaceous peony with extraction using alcohol, concentrate, dilution neutralization, sodium hydrogen carbonate solution extract, ethyl acetate extraction again, concentrate drying, yield is about 3%, content of paeoniflorin is greater than 60%.Zhao Xin waits the people to report a kind of novel method (CN 97101960.6) of extracting white peony root's total glycoside earlier, and the root of herbaceous peony is used 40-95% alcohol-water solution reflux, thickening filtration, and filtrate transfers to pH3-9 with diluted alkaline, the alcohol ester solution extraction, concentrate drying, yield are 5-7%.But above-mentioned two kinds of products that method obtains all are the miscellanys of Chinese herbaceous peony general glycoside, are not monomeric compound.
Summary of the invention
The object of the invention provides glycoside compound monomer in a kind of Chinese herbaceous peony.Comprise that paeoniflorin monomer, peony lactone glucoside monomer, benzoyl are called medicine glucoside monomer together with/Huo Hydroxyalkyl base paeoniflorin monomer, wherein the paeoniflorin monomer content is 90%
More than, to meet the purity requirement of a class plant kind new medicine.
Another object of the present invention provides the monomeric purifying extracting method of glycoside compound in a kind of above-mentioned Chinese herbaceous peony, refers in particular to content at the monomeric purifying extracting method of 90% above paeoniflorin.Be to have existing problem in extraction, the purification technique now in order to solve, method of the present invention is mainly used the method for distribution chromatography.
The present invention is a glycoside compound monomer in a kind of Chinese herbaceous peony.The glycoside compound monomer is meant that paeoniflorin monomer, peony lactone glucoside monomer, benzoyl call the monomer of medicine glucoside monomer Huo Hydroxyalkyl base paeoniflorin together in the described Chinese herbaceous peony, and wherein paeoniflorin monomer purity (content) meets the purity requirement of a class plant kind new medicine more than 90%.
The monomeric purifying extracting method of glycoside compound in a kind of above-mentioned Chinese herbaceous peony of the present invention.Be to be raw material, the root of herbaceous peony or the radix paeoniae rubrathe be put into swelling in the alcohol solution, reflux 0.5～5 hour with the root of herbaceous peony or the radix paeoniae rubrathe, filter, be concentrated into medicinal extract, use the acetone soln supersound extraction, extracting solution concentrates, admix silica-gel powder in the enriched material, be condensed into dry sample, go up the vacuum chromatographic column then, use the organic solvent wash-out again, obtain the first product of paeoniflorin, merge first product, purity is greatly about about 75%, the samely repeat to make dry sample, separate with silicagel column, use the organic solvent system wash-out, can add an amount of water, as add the water of 0-5% weight, make 1-6 sub-distribution chromatogram, the purity that obtains paeoniflorin (paeoniflorin) can be about 90%, and yield is about about 1.2%.Can further separate the standard substance that obtain paeoniflorin with present method.
Simultaneously, obtain Benzoylpaeoniflorin (benzoylpaeoniflorin) prior to the separation that can carry out 1-6 column chromatography repeatedly in the component of paeoniflorin composition lower prop during distribution chromatography; The back obtains peony lactone glucoside (albiflorin) and Oxypaeoniflorin (oxypaeoniflorin) respectively after the component of paeoniflorin composition lower prop carries out 1-6 chromatogram repeatedly again.Benzoylpaeoniflorin, peony lactone glucoside and Oxypaeoniflorin can be for the usefulness of foreign matter content in the control paeoniflorin.
When above-mentioned vacuum chromatogram and distribution chromatography, all with the gradient elution of the organic solvent of the water that contains 0-5% weight for well.
Shown in Figure 1 in the typical process of albiflorin constituents separation and purification such as the accompanying drawing.
In the monomeric purifying extracting method of paeoniflorin, the concentration of alcohol is 30%～95% in the described alcohol solution, and the weight ratio of the root of herbaceous peony or the radix paeoniae rubrathe and alcohol solution is 1: 1～10, and ratio is 1: 3～10 preferably, further improves ratio to not influence of result; The weight ratio of medicinal extract and acetone is 1: 1～20, and ratio is 1: 2～10 when suitable; The weight ratio of enriched material and silica-gel powder is 1: 1～6; During the vacuum chromatographic column, usually vacuum tightness is 0.02～0.098Mpa, and the used organic solvent of wash-out is the haloalkane of low carbon chain, the alcohol of low carbon chain, the ester of low carbon chain, or the mixture of two kind solvents wherein.The haloalkane of low carbon chain refers to methyl halide, halo ethane etc., and as three ammonia methane, methylene dichloride, ethylene dibromide, trichloromethane etc., the alcohol of low carbon chain refers to C
1-3Alcohol, as methyl alcohol, ethanol, propyl alcohol, Virahol, the ester of low carbon chain refers to C
1-5Ester, as methyl-formiate or ethyl ester, methyl acetate or ethyl ester etc.When the mixed solvent of the ester of the alcohol of haloalkane that uses low carbon chain and low carbon chain or low carbon chain, the ester of the haloalkane of low carbon chain, the alcohol of low carbon chain or low carbon chain, and the weight ratio of water be 1: 1: 0-5.
During above-mentioned chromatogram, the component prior to paeoniflorin composition lower prop contains Benzoylpaeoniflorin, after the merging, carry out the gradient separations of column chromatography repeatedly, organic solvent is made distribution chromatography, the haloalkane of low carbon chain and the alcohol of low carbon chain weight ratio be 50-15: 1, from 50: 1,25: 1,20: 1,15: 1 gradient ratio was for well, 1% water can be added, the composition of Benzoylpaeoniflorin (benzoylpaeoniflorin) can be obtained.
The composition of peony lactone glucoside and Oxypaeoniflorin is contained in the back in the component of paeoniflorin composition lower prop, after the merging, after going up silica gel column chromatography repeatedly, mixed solvent gradient elution with the alcohol of the haloalkane of low carbon chain and low carbon chain, the weight ratio 15-1 of the haloalkane of recommendation low carbon chain and the alcohol of low carbon chain: 1, with 15: 1,10: 1,8: 1,5: 1,4: 1,3: 1,2: 1 gradient ratio can obtain the composition of peony lactone glucoside (albiflorin) and Oxypaeoniflorin (oxypaeoniflorin) respectively for well.
Paeoniflorin is the topmost activeconstituents in the Chinese herbaceous peony, other glycosides composition is accessory composition or can be described as impurity component, must control its content limit according to the requirement that new drug is declared, so peony lactone glucoside of aforesaid method extraction separation, Benzoylpaeoniflorin, Oxypaeoniflorin can be used as the foreign matter content of standard reference material control paeoniflorin.
The present invention uses the method for distribution chromatography, can separate in a large number and obtain the paeoniflorin composition, content is more than 90%, can meet the purity requirement of a class plant kind new medicine, can further separate simultaneously obtaining peony lactone glucoside (albiflorin), benzoyl is called the medicine glucoside together, and (benzoylpaeoniflorin) is with Hydroxyalkyl base paeoniflorin (oxypaeoniflorin).The method simple possible, cost is lower, and yield is higher, is easy to grasp, and is fit to suitability for industrialized production.
Embodiment
To help to understand the present invention by following embodiment, but not limit content of the present invention.
Get grow radix paeoniae alba or radix paeoniae rubrathe 1kg medicine materical crude slice, extract twice with the heating of 30% ethanol liquid, extracted 1 hour at every turn, filter, reclaim ethanol to there not being the alcohol flavor, about about 400 grams of Chinese herbaceous peony medicinal extract, get 100 gram medicinal extract, with the acetone supersound extraction of triplication 30 minutes, extract twice, merge acetone extract, admix an amount of silica-gel powder (3～5 times of amounts), make dry sample, last vacuum chromatographic column, with the solvent gradient elution of methylene dichloride or ethylene dichloride and methyl alcohol or ethanol system (weight ratio is 50: 1,25: 1,15: 1,10: 1,8: 1,5: 1,2.5: 1,1: 1), obtain the first product of paeoniflorin, purity about about 75%, merges these first products greatly again, mix thoroughly with proper silica gel, make dry sample, separate, with the system of methylene dichloride and methyl alcohol with silicagel column, the water of adding 1%, make distribution chromatography, gradient elution, methylene dichloride or ethylene dichloride and methyl alcohol or alcoholic acid ratio were from 20: 1,15: 1,12: 1,10: 1,8: 1,5: 1, obtain paeoniflorin (paeoniflorin), purity is about 90%, and yield is about 1.2%～1.5%.Can further separate the standard substance that obtain paeoniflorin with present method.
Component prior to paeoniflorin composition lower prop, contain Benzoylpaeoniflorin, after the merging, can carry out the gradient separations of column chromatography repeatedly again, methylene dichloride or ethylene dichloride and methyl alcohol or alcoholic acid weight ratio be from 50: 1,25: 1,20: 1,15: 1, the water of adding 1% was made distribution chromatography, obtains the composition of Benzoylpaeoniflorin (benzoylpaeoniflorin).The composition of peony lactone glucoside and Oxypaeoniflorin is contained in the back in the component of paeoniflorin composition lower prop, after the merging, go up silica gel column chromatography repeatedly after, gradient elution, the weight ratio of methylene dichloride and methyl alcohol was from 15: 1,10: 1,8: 1,5: 1,4: 1,3: 1,2: 1, obtain the composition of peony lactone glucoside (albiflorin) and Oxypaeoniflorin (oxypaeoniflorin).
Embodiment 2
Get grow radix paeoniae alba 1kg medicine materical crude slice, extract twice, extracted 3 hours at every turn with the heating of 95% ethanol liquid, filter, recovery ethanol gets about about 400 grams of Chinese herbaceous peony medicinal extract to there not being the alcohol flavor, get 100 gram medicinal extract, the acetone supersound extraction of usefulness quintuple 60 minutes is extracted twice, merge acetone extract, admix an amount of silica-gel powder (3～5 times of amounts), make dry sample, last vacuum chromatographic column, and the solvent gradient elution of usefulness methylene dichloride and methyl alcohol or ethyl acetate system (weight ratio: 50: 1,25: 1,15: 1,10: 1,8: 1,5: 1,2.5: 1,1: 1), can obtain the first product of paeoniflorin, purity about about 75%, merges these first products greatly again, mix thoroughly with proper silica gel, make dry sample, separate with silicagel column, with the system of methylene dichloride and methyl alcohol, add 1% water, make distribution chromatography, gradient elution (weight ratio of methylene dichloride and methyl alcohol: 20: 1,15: 1,12: 1,10: 1,8: 1,5: 1), can obtain paeoniflorin (paeoniflorin), purity is about 90%, and yield is about 1.2%～1.5%.Can further separate the standard substance that obtain paeoniflorin with present method.Component prior to paeoniflorin composition lower prop, contain Benzoylpaeoniflorin, after the merging, can carry out the gradient separations of column chromatography repeatedly again, the weight ratio of methylene dichloride and methyl alcohol: 50: 1,25: 1,20: 1,15: 1, the water of adding 1% was made distribution chromatography, can obtain the composition of Benzoylpaeoniflorin (benzoylpaeoniflorin).The composition of peony lactone glucoside and Oxypaeoniflorin is contained in the back in the component of paeoniflorin composition lower prop, after the merging, after going up silica gel column chromatography repeatedly, gradient elution, the ratio of methylene dichloride and methyl alcohol was from 15: 1,10: 1,8: 1,5: 1,4: 1,3: 1, can obtain the composition of peony lactone glucoside (albiflorin) and Oxypaeoniflorin (oxypaeoniflorin) at 2: 1.
The influence of rat paw edema due to embodiment 3 on Carrageenan
Tried thing: paeoniflorin (NN002)
Positive control: acetylsalicylic acid
Cause scorching thing: carrageenin
Laboratory animal: Wistar rat, body weight 250g-300g, male and female half and half.
Experimental technique: it is long-pending that drainage (Qi Chen edited herbal pharmacology research methodology People's Health Publisher 1993) is measured the mouse corpus unguis.
Get 48 rats, male and female half and half, body weight 250g-300g is divided into 6 groups at random, and 8 every group, i.e. physiological saline control group, acetylsalicylic acid control group, NN00210mg/kg, 50mg/kg dosage group.
Except that the acetylsalicylic acid control group with 150mg/kg dosage cause scorching preceding 1 hour gastric infusion once, the equal intraperitoneal injection of all the other experimental group, once a day, continuous 5 days.
1 hour sufficient plantar subcutaneous injection 1% carrageenin after the last administration (0.1m1/ only) causes rat paw edema, surveys sufficient sole of the foot volume with the kapillary multiplying arrangement, and causing scorching front and back volume difference with the sufficient sole of the foot is inflammation swelling degree.And began to measure sufficient sole of the foot volume-variation in back 1 hour in injection, observed continuously 7 hours.
Observation index:
Swelling rate %=(cause scorching metapedes volume consistent scorching front foot volume)/cause scorching front foot volume * 100%;
Inhibiting rate %=(the average swelling rate of the average swelling rate one administration group of the control group)/average swelling rate of control group * 100%
Statistical method: data input Excel table, adopt t check carrying out test of significance in groups.
Experimental result:
Table 1 is tried the effect of rat paw edema due to the thing on Carrageenan
Annotate:
*, P＜0.05;
*P＜0.01.Bracket inner digital is an inhibitory rate of intumesce
| Group | Number of animals | Dosage (mg/kg.d) | Cause scorching back different time swelling rate (%) | ||||||
| ????1 | ????2 | ????3 | ????4 | ????5 | ????6 | ????7 | |||
| Physiological saline | ????8 | ????- | ????25.87±10.35 | ????39.73±15.85 | ????47.61±26.14 | ????63.37±21.78 | ????52.55±16.81 | ????40.74±22.28 | ????46.03±15.05 |
| Acetylsalicylic acid | ????8 | ????150 | ????17.08±5.48 ????(33.99) | ????24.17±10.29 *????(39.16) | ????24.52±6.82 *????(48.49) | ????19.10±8.77 **????(69.86) | ????19.10±8.34 **????(63.65) | ????24.41±13.87 ????(42.2?1) | ????25.29±15.29 ????(36.49) |
| ??NN002 | ????8 | ????10×5 | ????30.57±16.72 ????(-18.17) | ????47.44±23.55 ????(-19.41) | ????54.12±25.12 ????(13.67) | ????49.90±20.73 ????(21.25) | ????31.63±18.68 *????(39.82) | ????28.13±18.78 ????(33.41) | ????26.75±17.88 *????(32.81) |
| ????8 | ????50×5 | ????23.83±13.40 ????(7.88) | ????39.61±20.07 ????(0.30) | ????47.42±16.3 ????(0.39) | ????41.60±14.79 *????(30.35) | ????34.21±13.37 *????(34.89) | ????35.09±9.73 ????(16.92) | ????27.41±19.73 *????(31.17) | |
As shown in Table 1, acetylsalicylic acid rat paw edema due to 1 hour to 7 hours the equal on Carrageenan of experiment whole process is restraining effect, inhibiting rate is about 30-70%, compare with the physiological saline control group, statistical significant difference (p＜0.05) was arranged at 2,3 hours, statistics significant differences (p＜0.01) was arranged in 4,5 hours; NN002 presents after 4 hours that rat paw edema has inhibiting trend due to the on Carrageenan, inhibiting rate is the highest by about 40%, compare with control group, its 10mg/kg * 5d organized at 5,7 hours, and 50mg/kg * 5d group has significance,statistical poor (p＜0.05) 4,5,7 hours restraining effect to swelling.
Experiment conclusion and analysis:
It is the main acute inflammation model that changes that the pharmacodynamics evaluation of anti-inflammatory drug, resisting rheumatoid arthritis medicine is generally selected for use with the vascular permeability, and carrageenin is proinflammatory agent commonly used, and swelling model is reliable due to it, and otherness is little, and susceptibility and repeatability are high.The drainage of measuring the swelling degree is easy, stable and highly sensitive.The effect of rat paw edema due to the above-mentioned common model evaluation of this experiment employing NN002 on Carrageenan.
The preliminary experiment results suggest, in used dosage range, rat paw edema has restraining effect due to the NN002 on Carrageenan, and its effect is slow and lasting than acetylsalicylic acid.
Claims (7)
1. glycoside compound monomer that from Chinese herbaceous peony, extracts the purifying gained, it is characterized in that the glycoside compound monomer is the monomer of paeoniflorin monomer, peony lactone glucoside monomer, Benzoylpaeoniflorin monomer Huo Hydroxyalkyl base paeoniflorin in the described Chinese herbaceous peony, wherein the paeoniflorin monomer purity is more than 90%.
2. as claimed in claim 1 a kind of from Chinese herbaceous peony purifying extract the glycoside compound monomer methods, it is characterized in that adopting following method:
1) root of herbaceous peony or the radix paeoniae rubrathe are put into swelling in the alcohol solution, reflux 0.5～5 hour is filtered, be concentrated into medicinal extract, use the acetone soln supersound extraction, extracting solution concentrates, admix silica-gel powder in the enriched material, be condensed into dry sample, go up the vacuum chromatographic column then, use the organic solvent wash-out again, obtain the first product of paeoniflorin, merge first product and repeat to make dry sample, separate with silicagel column, carry out 1-6 sub-distribution chromatogram again, get the paeoniflorin monomer;
2) separation of carrying out 1-6 column chromatography repeatedly prior to the component of paeoniflorin composition lower prop during distribution chromatography obtains Benzoylpaeoniflorin; 3) back obtains peony lactone glucoside and Oxypaeoniflorin respectively after the component of paeoniflorin composition lower prop carries out 1-6 chromatogram repeatedly again;
Above-mentioned silicagel column separate or distribution chromatography in all with the organic solvent system wash-out of the water that contains 0-5% weight.
3. as claimed in claim 2 a kind of from Chinese herbaceous peony purifying extract the method for paeoniflorin, it is characterized in that the concentration of alcohol is 30%～95% in the alcohol solution in the described alcohol solution, the weight ratio of the root of herbaceous peony or the radix paeoniae rubrathe and alcohol solution is 1: 1～10.
4. as claimed in claim 2 a kind of from Chinese herbaceous peony purifying extract the method for paeoniflorin, the weight ratio that it is characterized in that described medicinal extract and acetone is 1: 1～20; The weight ratio of enriched material and silica-gel powder is 1: 1～6.
5. as claimed in claim 2 a kind of from Chinese herbaceous peony purifying extract the method for paeoniflorin, it is characterized in that described silicagel column separates or distribution chromatography in all carry out gradient elution with the organic solvent system of the water that contains 0-5% weight.
6. as claimed in claim 2 a kind of from Chinese herbaceous peony purifying extract the method for paeoniflorin, it is characterized in that the used organic solvent of described wash-out is the haloalkane of low carbon chain, the alcohol of low carbon chain, the ester of low carbon chain, or the mixture of two kind solvents wherein.The haloalkane of low carbon chain refers to methyl halide, halo ethane etc., and as trichloromethane, methylene dichloride, ethylene dibromide, methenyl bromide etc., the alcohol of low carbon chain refers to C
1-3Alcohol, as methyl alcohol, ethanol, propyl alcohol, Virahol, the ester of low carbon chain refers to C
1-5Ester, as methyl-formiate or ethyl ester, methyl acetate or ethyl ester etc.
7. as claimed in claim 2 a kind of from Chinese herbaceous peony purifying extract the method for paeoniflorin, when it is characterized in that described wash-out uses the mixed solvent of ester of the alcohol of the haloalkane of low carbon chain and low carbon chain or low carbon chain, the ester of the haloalkane of low carbon chain, the alcohol of low carbon chain or low carbon chain, and the weight ratio of water be 1: 1: 0-5.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101073606B (en) * | 2006-05-18 | 2011-06-08 | 天津天士力制药股份有限公司 | Method for separating and extracting white Peony Root |
| CN102133278A (en) * | 2011-03-10 | 2011-07-27 | 湖南朗林生物制品有限公司 | Preparation method of 98% of paeoniflorin radix in radix paeoniae alba extract |
| CN1706397B (en) * | 2005-02-04 | 2011-11-16 | 沈阳药科大学 | Composition of paeoniflorin and peony lactone glycoside with function of increasing leukocyte |
| WO2012019373A1 (en) * | 2010-08-10 | 2012-02-16 | 张作光 | Method for preparing paeoniflorin and albiflorin |
| CN102492005A (en) * | 2011-12-12 | 2012-06-13 | 苏州大学 | Method for preparing paeoniflorin and albiflorin |
| CN102038701B (en) * | 2009-10-20 | 2012-06-27 | 张作光 | Anti-depression application of albiflorin |
| CN103059080A (en) * | 2012-12-13 | 2013-04-24 | 大兴安岭林格贝有机食品有限责任公司 | Process for separating and purifying paeoniflorin |
| CN104306658A (en) * | 2014-10-29 | 2015-01-28 | 重庆华森制药有限公司 | Preparation method of pain-relieving and antidiarrheal granule |
| CN107271601A (en) * | 2017-01-19 | 2017-10-20 | 安徽九洲方圆制药有限公司 | A kind of discrimination method of Radix-paeoniae-rubra formula granules and white peony root dispensing granule |
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2002
- 2002-03-07 CN CNB021109737A patent/CN1169821C/en not_active Expired - Fee Related
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1706397B (en) * | 2005-02-04 | 2011-11-16 | 沈阳药科大学 | Composition of paeoniflorin and peony lactone glycoside with function of increasing leukocyte |
| CN101073606B (en) * | 2006-05-18 | 2011-06-08 | 天津天士力制药股份有限公司 | Method for separating and extracting white Peony Root |
| CN102038701B (en) * | 2009-10-20 | 2012-06-27 | 张作光 | Anti-depression application of albiflorin |
| WO2012019373A1 (en) * | 2010-08-10 | 2012-02-16 | 张作光 | Method for preparing paeoniflorin and albiflorin |
| CN102133278A (en) * | 2011-03-10 | 2011-07-27 | 湖南朗林生物制品有限公司 | Preparation method of 98% of paeoniflorin radix in radix paeoniae alba extract |
| CN102492005A (en) * | 2011-12-12 | 2012-06-13 | 苏州大学 | Method for preparing paeoniflorin and albiflorin |
| CN102492005B (en) * | 2011-12-12 | 2015-05-06 | 苏州大学 | Method for preparing paeoniflorin and albiflorin |
| CN103059080A (en) * | 2012-12-13 | 2013-04-24 | 大兴安岭林格贝有机食品有限责任公司 | Process for separating and purifying paeoniflorin |
| CN103059080B (en) * | 2012-12-13 | 2016-01-20 | 大兴安岭林格贝寒带生物科技股份有限公司 | A kind of separation purifying technique of peoniflorin |
| CN104306658A (en) * | 2014-10-29 | 2015-01-28 | 重庆华森制药有限公司 | Preparation method of pain-relieving and antidiarrheal granule |
| CN107271601A (en) * | 2017-01-19 | 2017-10-20 | 安徽九洲方圆制药有限公司 | A kind of discrimination method of Radix-paeoniae-rubra formula granules and white peony root dispensing granule |
| CN107271601B (en) * | 2017-01-19 | 2019-06-11 | 安徽九洲方圆制药有限公司 | A kind of discrimination method of Radix-paeoniae-rubra formula granules and white peony root dispensing granule |
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