CN102060889A - Stilbene glycoside derivative - Google Patents
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- CN102060889A CN102060889A CN2010105796122A CN201010579612A CN102060889A CN 102060889 A CN102060889 A CN 102060889A CN 2010105796122 A CN2010105796122 A CN 2010105796122A CN 201010579612 A CN201010579612 A CN 201010579612A CN 102060889 A CN102060889 A CN 102060889A
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Abstract
The invention relates to a novel 2,3,5,4'-tetrahydroxy stilbene-2-O-beta-D-glucoside crystal and a preparation method thereof as well as a medicine composition containing the crystal. The content of the crystal is 90%-99.9% through the measurement of a high performance liquid chromatography. The preparation method the high-purity stilbene glycoside crystal comprises the steps of Polygonum multiflorum extraction, organic solvent extraction, column chromatography separation, crystallization in a proper solvent and the like. The preparation method provided in the invention has the advantages of high yield and low cost and is suitable for industrialized production.
Description
Technical field
The invention belongs to medical technical field, relate to effective monomer 2,3,5,4 in the Tuber Fleeceflower Root '-separation purifying technique of tetrahydroxystilbene-2-O-β-D-glucoside; Also relate to 2,3,5,4 '-crystal of tetrahydroxystilbene-2-O-β-D-glucoside and preparation method thereof, and be the pharmaceutical composition of main component with it.
Background technology
Tuber Fleeceflower Root is the piece root of polygonum multiflorum thunb (pllygonum multiflorum Thunb.), is conventional Chinese medicine, and medicinal history is long, The experimental results both domestic and external shows: Tuber Fleeceflower Root has immunomodulatory, protect the liver many-sided pharmacologically active such as anti-oxidant, antitumor, reducing blood-fat.Along with going deep into of research, also more and more clear to its The Chemical Constituents, studies show that in a large number, in the Tuber Fleeceflower Root what play a major role is 2,3,5,4 '-tetrahydroxystilbene-2-O-β-D-glucoside (hereinafter to be referred as stilbene glucoside).The physiologically active of stilbene glucoside mainly contains: anti-aging effects, reducing blood lipid, liver protection function, improve memory function, antitumor action etc. (referring to Shandong heavily fortified point, Hou Shuanqiu etc., Research Progress on Stilbene Glucoside, the Anhui chemical industry, 2006 (3), 10～13).The application of stilbene glucoside in the treatment dementia disclosed among the Chinese patent ZL01134284.6.The application of stilbene glucoside in the treatment ischemic cerebrovascular disclosed among the Chinese patent application CN01134283.8.
Along with the medicinal efficacy of stilbene glucoside constantly is found, industrial hope obtains a large amount of suitable medicinal stilbene glucoside raw materials, describedly is fit to medicinal stilbene glucoside raw material and should possesses higher purity at least and prepare the desired physical properties of preparation.But because the restriction of state of the art, the separation and purification of high purity stilbene glucoside still is in the level of laboratory minute quantity preparation always, do not see the report that the high purity of suitable suitability for industrialized production scale stilbene glucoside preparation technology is arranged, therefore, carrying out the separation purifying technique that is fit to medicinal stilbene glucoside studies significant.
At present, the main methods such as high performance liquid chromatography, crystallization process, resin column that adopt prepare highly purified stilbene glucoside in the prior art.
Though high performance liquid chromatography can access the stilbene glucoside of based on very high purity, its purification efficiency is difficult to improve, and the purifying cost is also higher relatively, thereby this method is mainly used in prepared in laboratory, is difficult to be applied to suitability for industrialized production.
People such as class's assist disclose a kind of method (referring to class's assist, Liu Qili, Jin You etc., the stability study of stilbene glucoside, herbal medicine, 2004,35 (11), 1235～1237) of crystal refining stilbene glucoside.This method is utilized the Tuber Fleeceflower Root medicinal extract of ethanol refluxing process gained, with behind an amount of distilled water diluting with equivalent extracted with diethyl ether 3 times, isolate water layer; The vinyl acetic monomer layer is collected in the vinyl acetic monomer thermal backflow of water layer usefulness two volumes 5～6 hours, is evaporated to 1/10 of original volume, and room temperature leaves standstill, and crystallization filters, and gets crude product.Crude product dissolves in an amount of hot water or hot vinyl acetic monomer, filters while hot, puts the cold analysis crystalline substance, periodic crystallisation like this, grey imperfect crystal formation powder, mp.162～163 ℃, by analysis, stilbene glucoside purity is 99.94%.Though this method can access the very high toluylene glycoside product of purity, need the repeated multiple times crystallization, technology is loaded down with trivial details, and the organic solvent consumption is big, and resource utilization is low, and will use inflammable and explosive reagent such as ether, is not suitable for suitability for industrialized production.
Other documents disclose the method that adopts macroporous adsorbent resin separation and purification stilbene glucoside (referring to Zhu Haisheng etc., the research of macroporous adsorbent resin separation and purification Tuber Fleeceflower Root effective constituent stilbene glucoside, PLA's Acta Pharmaceutica Sinica, 2006,22 (4), 269～273 and Lv Lishuan etc., the technical study of stilbene glucoside in the macroporous resin purification Tuber Fleeceflower Root, Food science, 2005,6 (26), 178～181).These documents also all are based on the fundamental research that laboratory study is carried out, and used amount of resin generally also has only several grams, also can't compare with industrialized producing technology, and the stilbene glucoside purity that makes also reach monomeric specification of quality far away.
In addition, Chinese patent ZL 98120290.X discloses a kind of method for preparing stilbene glucoside, the chromatography column that this method will be used for separation and purification carries out the destructiveness cutting, the separation of taking a sample again, process is loaded down with trivial details, cost is high, also is the method for typical prepared in laboratory micro-example, can't reach industrial production requirement.
The invention provides a kind of extraction and separation method of stilbene glucoside, this method is easy and simple to handle, with low cost, stable yield, can satisfy the demand of suitability for industrialized production scale fully, the stilbene glucoside purity that makes can obtain highly purified toluylene glycosidal crystalline when guaranteeing that low-cost and high receipts are considered, reached industrial production requirement.The present invention also provides a kind of stilbene glucoside of new physics form in addition, and the pharmaceutical composition that contains this form, and new physical aspect has the physical properties of preparation preparation preferably.
Summary of the invention
The object of the present invention is to provide the method for a kind of extraction separation structure suc as formula 1 compound, described extraction and separation method is as follows:
Formula I
A) extract: get the Tuber Fleeceflower Root medicinal material, drink in cataclasm, the mixed solvent that adds one or more solvent compositions in a certain amount of water, methyl alcohol, the ethanol, regulate pH to 7.0～8.0 of extracting solution, heating is extracted 1～4 time, each 1～3 hour, Heating temperature is 40 a ℃～reflux temperature, united extraction liquid is put coldly, filters.Wherein extract the solvent preferably water; What regulate extracting liquid pH value can be acid, alkali or salt, and preferred sodium hydroxide, S-WAT, sodium bisulfite, yellow soda ash most preferably are S-WAT; The pH value of extracting solution is preferably 7.5; Preferred extraction 3 times, each 1.5 hours are extracted in heating.
B) separate: said extracted liquid is crossed macroporous resin column, after adding the abundant wash-out of water and removing inorganic salt and other impurity in the extracting solution, use certain density organic solvent wash-out instead, collect the elutriant that contains stilbene glucoside.The model of macroporous resin can be HPD-400, HPD-100, AB-8, D1300, and preferred macroporous resin model is HPD-400; Eluting solvent can be preferably ethanol for ethanol, methyl alcohol or acetone, and more preferably concentration is 70% ethanol.
C) extraction: 1/10～1/30 (V/V) that elutriant is evaporated to former effluent volume under 60～80 ℃, can add an amount of water as the concentrated solution volume is less, add the sherwood oil, ether, chloroform, ethyl acetate of 1～2 times of concentrated solution volume or n-butanol extraction 2～4 times, the collected organic layer extraction liquid, the organic layer extraction liquid is evaporated to dried, obtains the solid crude extract; Preferably elutriant is concentrated into 1/20 of original volume.Extract used organic solvent ethyl acetate; Preferably use 1 times the organic solvent extraction 3 times of concentrated solution volume.
D) purifying: above-mentioned crude extract is dissolved in appropriate amount of organic, crosses chromatography column, selects for use appropriate solvent to carry out wash-out, collects the elutriant that contains the stilbene glucoside composition, concentrates, and drying gets the stilbene glucoside crude product.The filler of chromatography column can be silica gel or aluminum oxide, preferred aluminum oxide; The order number is 100-200 order or 200-300 order, is preferably the 200-300 order; Dissolving crude extract solvent for use can be acetone, ethanol, ethyl acetate before the column chromatography, is preferably ethanol; Used elutriant can be the mixed solvent of one or more solvent compositions in acetone, ethyl acetate, ethanol, methyl alcohol or the chloroform in the column chromatography process, is preferably ethyl acetate.
E) crystallization: with above-mentioned stilbene glucoside crude product at acetone, water, methyl alcohol, ethanol, heating for dissolving in the mixed solvent of one or more solvent compositions in the ethyl acetate, preferred recrystallisation solvent is an acetone: water: the mixed solvent of ethyl acetate, its ratio is 1～10: 5～20: 1～10 (V: V: V), acetone most preferably: water: ethyl acetate is 2: 10: 1 (V: V: V), the consumption of recrystallisation solvent is 1～10 times (V/W) for the stilbene glucoside crude product, preferred solvent load is 5 times (V/W) of stilbene glucoside crude product, activated carbon decolorizing, filter, leave standstill crystallization, Tc is-20～10 ℃, be preferably-10～5 ℃, optimum temps is-4 ℃, filters, drying promptly obtains highly purified stilbene glucoside.
Stilbene glycoside extract of the present invention detects its purity with high performance liquid chromatography and can reach more than 90%, preferably more than 95%, most preferably more than 98%.
The assay of stilbene glucoside adopts high performance liquid chromatography (HPLC) method to carry out among the present invention.Use therein 2,3,5,4 '-tetrahydroxystilbene-2-O-β-D-glucoside reference substance is purchased in Nat'l Pharmaceutical ﹠ Biological Products Control Institute; The moving phase of using is acetonitrile: water=15: 85; Detector is JASW UV-1575; Flow velocity is 1mL/min; Chromatographic column adopting Agilent Extend C-18 (4.6mm * 250mm, 5 μ m); Column temperature is 30 ℃, and concrete testing method is as follows:
1. the foundation of typical curve
Precision takes by weighing 2,3,5,4 '-tetrahydroxystilbene-2-O-β-D-glucoside reference substance 5.15mg, with water dissolution and be settled to 100ml, be made into the reference substance storing solution, get storing solution 1ml respectively, 2ml, 4ml, 6ml, 8ml, each self-watering is settled to 10ml, get the reference substance solution 20 μ l of above-mentioned each concentration respectively, injecting chromatograph obtains the peak area data shown in the table one successively, make the stilbene glucoside typical curve shown in the table two thus, be good linear relationship between visible sample size and peak area.
Linearity range: 5～50 μ g/ml
Regression equation is: Y=80909X+19722
Relation conefficient: R=0.9992
Table one stilbene glucoside standard substance concentration and peak area data
| Concentration (μ g/ml) | 5.15 | 10.30 | 20.60 | 30.90 | 41.20 |
| Peak area (mv/s) | 415797 | 888128 | 1706896 | 2445922 | 3392192 |
2. the content assaying method of stilbene glucoside sample
Accurately take by weighing stilbene glucoside reference substance (abbreviation reference substance) and each 20.00mg of homemade stilbene glucoside sample (abbreviation trial-product), use water dissolution respectively, and be settled to 100ml, and respectively get the 1ml thin up and be settled to 10ml, obtain reference substance solution and need testing solution.Draw each 20 μ l of above-mentioned two kinds of solution injecting chromatograph successively respectively, the record peak area, the utilization external standard method is calculated, and obtains the content of stilbene glucoside in the trial-product.
The high-efficient liquid phase chromatogram of stilbene glucoside of the present invention and stilbene glucoside reference substance (purchasing in Nat'l Pharmaceutical ﹠ Biological Products Control Institute) is shown in accompanying drawing 5 and accompanying drawing 6.
Novel crystal that provides stilbene glucoside and preparation method thereof is provided another object of the present invention,
A further object of the present invention is to provide and contains described stilbene glucoside crystalline pharmaceutical composition.
Not moisture substantially and other organic solvent of stilbene glucoside crystal of the present invention, its X-ray powder diffraction spectrogram (this collection of illustrative plates is with Cu-K α radiation measurement on the X`TRA-X x ray diffractometer x), be 4.772,4.471,3.678 in the d value, located diffraction peak, typically at 14.572,12.200,4.772,4.471,3.678,3.622 places diffraction peak is arranged, more typical have diffraction peak at 14.572,12.200,7.320,4.772,4.471,3.678,3.622,3.343,2.384 places.
Stilbene glucoside crystalline differential scanning calorimetric analysis of the present invention (adopting NETZSCH DSC 204F1 instrument) heats up with 10K/ minute speed, and it absorbs the heat deflection peak value and is about 178 ℃.
Stilbene glucoside crystal of the present invention uses the infrared absorption spectrum of KBr compressing tablet mensuration at 3333cm
-1(broad peak), 1607cm
-1, 1593cm
-1, 1515cm
-1There is absorption peak at the place.
Stilbene glucoside crystalline thermogravimetic analysis (TGA) collection of illustrative plates of the present invention as shown in Figure 4.
Stilbene glucoside crystal of the present invention can be by the preparation of following method: with stilbene glucoside crude product or pure product at acetone, water, methyl alcohol, ethanol, heating for dissolving in the mixed solvent of one or more solvent compositions in the ethyl acetate, preferred recrystallisation solvent is an acetone: water: the mixed solvent of ethyl acetate, its ratio is 1～10: 5～20: 1～10 (V: V: V), acetone most preferably: water: ethyl acetate is 2: 10: 1 (V: V: V), the consumption of recrystallisation solvent is 1～10 times (V/W) for the stilbene glucoside crude product, preferred solvent load is 5 times (V/W) of stilbene glucoside crude product, activated carbon decolorizing, filter, leave standstill crystallization, Tc is-20～10 ℃, be preferably-10～5 ℃, optimum temps is-4 ℃, filters, drying promptly obtains highly purified toluylene glycosidal crystalline.
The stilbene glucoside crystal that makes according to above-mentioned steps, can also mix with suitable pharmaceutical excipient, make the composition of a definite form, comprise tablet, capsule, dripping pill, soft capsule, injection liquid or other dosage form that is suitable for using, use clinically with convenient.
The invention provides a kind of content height, definite ingredients, quality controllable, drug effect is definite, side effect is little novel toluylene glycosidal crystalline and preparation method thereof, the toluylene glycosidal crystalline is different from unformed stilbene glucoside, it is more stable, solubleness is all different with bioavailability simultaneously, wherein the easier medicament that is prepared into of toluylene glycosidal crystalline.Contain high purity stilbene glucoside crystalline pharmaceutical composition so present invention includes, this pharmaceutical composition is obvious in treatment hyperlipidemia, atherosclerosis, effect such as anti-oxidant.Preparation technology of the present invention produces checking by many batches, proves that its repeatability, stability are all good, and the total recovery height, only needs a step crystallization, not only is suitable for industrialized production but also reduced production cost.The stilbene glucoside purity height of method provided by the present invention preparation, impurity is few, has not only improved shortcomings such as the taking dose that Chinese patent medicine often has is big, composition is indeterminate, and its drug effect is remarkable clinically, have good suitability.
Description of drawings
Fig. 1 stilbene glucoside crystalline X-ray powder diffraction spectrogram.
Fig. 2 stilbene glucoside crystalline differential scanning calorimetric analysis (DSC) collection of illustrative plates.
Fig. 3 stilbene glucoside crystalline infrared absorption pattern.
Fig. 4 stilbene glucoside crystalline thermogravimetic analysis (TGA) (TGA) collection of illustrative plates.
Fig. 5 stilbene glucoside crystalline high-efficient liquid phase chromatogram.
The high-efficient liquid phase chromatogram of Fig. 6 stilbene glucoside reference substance.
Fig. 7 stilbene glucoside typical curve
Embodiment:
Following non-limiting example is for novel high purity stilbene glucoside crystalline preparation method provided by the present invention is described better, and does not mean that any limitation of the invention.
In the following example, used extraction water is a tap water; Used ethanol is pharmaceutical grade; The Tuber Fleeceflower Root medicinal material place of production is Haozhou, an Anhui Chinese Medicinal Materials Markets; Silica gel and aluminum oxide are all available from Qingdao Marine Chemical Co., Ltd..
Get exsiccant Tuber Fleeceflower Root medicinal material 100kg, be cut into the thin slice of 1-3mm, the thermal backflow extractor of packing into, the water and the S-WAT that add 10 times of amounts are an amount of, regulate extracting solution pH to 7.6, heating and refluxing extraction 3 times, each 1 hour, united extraction liquid filtered, and collects filtrate.Filtrate is crossed the HPD-400 macroporous adsorptive resins, after adding water 500L wash-out, add 80% ethanol elution, collection contains the elutriant of stilbene glucoside, amounts to 200L, is evaporated to 10L in 60 ℃, add ethyl acetate extraction 3 times, each consumption 10L, 60 ℃ of concentrating under reduced pressure acetic acid ethyl fluids get stilbene glucoside crude extract 2.5kg to doing.
Get above-mentioned crude extract, add ethanol 5.0L, heated and stirred is fully dissolved it, filter, filtrate is crossed 200-300 order neutral alumina chromatography column, uses eluent ethyl acetate instead after upper prop is finished, the thin layer monitoring, collection contains the elutriant of stilbene glucoside component, is evaporated to driedly in 50 ℃, obtains stilbene glucoside crude product 1.82kg.
Get above-mentioned crude product, add acetone: water: ethyl acetate (2: 10: 1, V/WV) 9L, 60 ℃ are heated to dissolving, after adding proper amount of active carbon, reflux 15 minutes, filtered while hot, filtrate is put under-5 ℃ of conditions and was left standstill 15 hours, after crystallization is abundant, filter, drying obtains white toluylene glycosidal crystalline 1.28kg.Get above-mentioned sample, carry out assay with high performance liquid chromatography, the stilbene glucoside content in crude product is 90.3%, and stilbene glucoside crystalline content is 98.9%.
Get exsiccant Tuber Fleeceflower Root medicinal material 100kg, be ground into meal, the thermal backflow extractor of packing into, the water and the sodium bisulfite that add 8 times of amounts are an amount of, regulate extracting solution pH to 7.5, heating and refluxing extraction 2 times, each 2 hours, united extraction liquid filtered, and collects filtrate.Filtrate is crossed the HPD-100 macroporous adsorptive resins, after adding water 600L wash-out, add 70% ethanol elution, collect the elutriant that contains stilbene glucoside, amount to 300L, be evaporated to 15L in 70 ℃, add n-butanol extraction 2 times, each consumption 15L, 80 ℃ of concentrating under reduced pressure, concentrate propyl carbinol to doing, get stilbene glucoside crude extract 2.3kg.
Get above-mentioned crude extract, add ethyl acetate 8.0L, heated and stirred is fully dissolved it, filter, filtrate is crossed 200-300 order silica gel column chromatography, uses ethyl acetate after upper prop is finished instead: acetone (2: 1) wash-out, the thin layer monitoring, collection contains the elutriant of stilbene glucoside component, is evaporated to driedly in 60 ℃, obtains stilbene glucoside crude product 1.60kg.
Get above-mentioned crude product, add entry: ethyl acetate (20: 1, V/V) 8L, 60 ℃ are heated to dissolving, after the adding proper amount of active carbon, and reflux 5 minutes, filtered while hot, filtrate is put under-10 ℃ of conditions and was left standstill 10 hours, after crystallization is abundant, filters, dry, obtain white toluylene glycosidal crystalline 1.28kg, crystallization is a needle-like, assembles cluster.Get above-mentioned sample, carry out assay with high performance liquid chromatography, the stilbene glucoside content in crude product is 91.1%, and stilbene glucoside crystalline content is 99.6%.
Embodiment 3
Get exsiccant Tuber Fleeceflower Root medicinal material 120kg, be ground into meal, the thermal backflow extractor of packing into, the water and the yellow soda ash that add 7 times of amounts are an amount of, regulate extracting solution pH to 7.8, heating and refluxing extraction 3 times, each 1.5 hours, united extraction liquid filtered, and collects filtrate.Filtrate is crossed the AB-8 macroporous adsorptive resins, after adding water 600L wash-out, add 90% ethanol elution, collect the elutriant that contains stilbene glucoside, amount to 320L, be evaporated to 20L in 70 ℃, add ethyl acetate extraction 3 times, each consumption 20L, 80 ℃ of concentrating under reduced pressure, concentrate ethyl acetate to doing, get stilbene glucoside crude extract 2.92kg.
Get above-mentioned crude extract, add acetone 12L, heated and stirred is fully dissolved it, filter, filtrate is crossed 200-300 order neutral alumina post, uses eluent ethyl acetate instead after upper prop is finished, the thin layer monitoring, collection contains the elutriant of stilbene glucoside component, is evaporated to driedly in 50 ℃, obtains stilbene glucoside crude product 1.9kg.
Get above-mentioned crude product, add acetone: water: ethyl acetate (1: 10: 1, V/V/V) 10L, 50 ℃ are heated to dissolving, after the adding proper amount of active carbon, and reflux 10 minutes, filtered while hot, filtrate is put under-4 ℃ of conditions and was left standstill 20 hours, after crystallization is abundant, filters, dry, obtain white toluylene glycosidal crystalline 1.51kg, crystallization is a needle-like, assembles cluster.Get above-mentioned sample, carry out assay with high performance liquid chromatography, the stilbene glucoside content in crude product is 92.8%, and stilbene glucoside crystalline content is 99.9%.
Claims (12)
1. the method for the following compound of an extraction separation structural formula, described extraction and separation method comprises:
A. get the Tuber Fleeceflower Root medicinal material, drink in cataclasm, add the mixed solvent of one or more solvent compositions in entry, methyl alcohol, the ethanol, regulate pH to 7.0～8.0 of extracting solution, heating is extracted, and puts coldly, filters;
B. said extracted liquid is crossed macroporous resin column, after adding water elution, use the organic solvent wash-out instead, collect the elutriant that contains stilbene glucoside, the model of macroporous resin can be HPD-400, HPD-100, AB-8, D1300, and eluting solvent can be ethanol, methyl alcohol or acetone;
C. with the elutriant concentrating under reduced pressure, add sherwood oil, ether, chloroform, ethyl acetate or n-butanol extraction, the collected organic layer extraction liquid is evaporated to the organic layer extraction liquid dried, obtains the solid crude extract;
D. above-mentioned crude extract is dissolved in organic solvent, cross chromatography column, collection contains the elutriant of stilbene glucoside composition, concentrate, drying gets the stilbene glucoside crude product, the filler of chromatography column can be silica gel or aluminum oxide, the order number is 100-200 order or 200-300 order, and dissolving crude extract solvent for use can be acetone, ethanol, ethyl acetate before the column chromatography, and used elutriant can be the mixed solvent of one or more solvent compositions in acetone, ethyl acetate, ethanol, methyl alcohol or the chloroform in the column chromatography process;
E. with heating for dissolving in the mixed solvent of one or more solvent compositions of above-mentioned stilbene glucoside crude product in acetone, water, methyl alcohol, ethanol, ethyl acetate, the consumption of recrystallisation solvent is 1～10 times (V/W) for the stilbene glucoside crude product, activated carbon decolorizing, filter, leave standstill crystallization, Tc is-20～10 ℃, filters, drying promptly gets stilbene glucoside.
2. among the claim 1 step a, the extraction solvent is a water.
3. among the claim 1 step b, the macroporous resin model is HPD-400.
4. among the claim 1 step b, eluting solvent is an ethanol.
5. among the claim 1 step c, extracting used organic solvent is ethyl acetate.
6. in claim 1 steps d, the filler of chromatography column is an aluminum oxide.
7. in claim 1 steps d, used elutriant is an ethyl acetate in the column chromatography process.
8. among the claim 1 step e, recrystallisation solvent is an acetone: water: ethyl acetate is 1～10: 5～20: 1～10 mixed solvent, solvent load are 5 times of stilbene glucoside crude product.
9. the stilbene glucoside crystal of not moisture substantially and other organic solvent is characterized in that: its X-ray powder diffraction spectrogram is 4.772,4.471,3.678 in the d value, located diffraction peak.
10. the described stilbene glucoside crystal of claim 9, its X-ray powder diffraction spectrogram is that 14.572,12.200,4.772,4.471,3.678,3.622 places have diffraction peak in the d value.
11. the described stilbene glucoside crystal of claim 9 heats up with 10K/ minute speed, its differential scanning calorimetric absorbs the heat deflection peak value and is about 178 ℃.
12. a pharmaceutical composition is characterized in that, contains claim 9,10 or 11 described stilbene glucoside crystal.
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| CN104042707A (en) * | 2013-11-28 | 2014-09-17 | 天津天狮生物发展有限公司 | Traditional Chinese medicinal composition containing Polygonum multiflorum Thunb extract, and preparation method thereof |
| CN104042707B (en) * | 2013-11-28 | 2016-04-13 | 天津天狮生物发展有限公司 | A kind of Chinese medicine composition and preparation method containing Radix Polygoni Multiflori extract |
| CN104546873A (en) * | 2014-12-31 | 2015-04-29 | 中国人民解放军第四军医大学 | Application of tetrahydroxyl stilbene glucoside to prevention and treatment of radioactive injuries |
| US10905703B2 (en) * | 2015-12-04 | 2021-02-02 | Huanggang normal university | Preparation of a composition containing stilbene glycoside |
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