CN101643515A - Method for separating and purifying lentinan for injection - Google Patents
Method for separating and purifying lentinan for injection Download PDFInfo
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- CN101643515A CN101643515A CN200810048721A CN200810048721A CN101643515A CN 101643515 A CN101643515 A CN 101643515A CN 200810048721 A CN200810048721 A CN 200810048721A CN 200810048721 A CN200810048721 A CN 200810048721A CN 101643515 A CN101643515 A CN 101643515A
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Abstract
The invention provides a method for separating and purifying lentinan for injection. The method comprises the following steps: removing proteins by using a water extraction and alcohol precipitation method and a trichloroacetic acid method to obtain a coarse product of lentinan; subjecting the coarse product of lentinan to decolorization by hydrogen peroxide to obtain decolored polysaccharide; andtreating the decolored polysaccharide by using the gel chromatography to obtain the lentinan for injection. The method provided by invention has the advantages of obviously lowering preparation cost,helping to lower economic burden of patients, saving resources, protecting environment, being suitable for industrialized production of the lentinan for injection, along with simple process and highyield.
Description
Technical field
The present invention relates to Natural Medicine Chemistry, more specifically relate to the separation of polysaccharides purifying.
Background technology
Lentinan (lentinan) is a kind of one-component polysaccharide (I) that extracts purifying in the umbrella mushroom section fungi mushroom fruiting body, it is a kind of immunity regulating type antitumor drug, it produces cell-mediated antitumous effect by the antineoplastic immune defensive raction of enhancing body, bring into play indirect antitumor action, normal cell is not produced toxic side effect, so lentinan is internationally recognized antitumor drug safely and effectively (with reference to patent of invention ZL 200410086152.4).Lentinan is mainly used in the treatment of malignant tumours such as cancer of the stomach, lung cancer, intestinal cancer and cancer ascites clinically, and lentinan all has better effect to the immunologic function that improves hepatitis and acquired immune deficiency syndrome (AIDS) patient in addition.
It is clinical that lentinan in 1985 enters as antitumor drug in Japan at first, the lentinan of China beginning in 1988 import Japan aginomoto.What sell on the domestic market at present mainly is the lentinan for injection (the ZL patent No. 00112407.2) that Nanjing Zhenzhong Biological Engineering Co., Ltd produces, its production of raw medicine technology be reference " Chihara.G.; Maeda.Y.;; Hamuro.G.; et al.Inhibition of mouse sarcoma 180 by polysaccharides from Lentinusedodes (berk.) sing.Nature; 1965,222,687-688 ", will use cetyltrimethyl ammonium in the production process; chloroform; propyl carbinol; the organic reagent that acetic acid etc. are a large amount of; technical process is very complicated; labour intensity is big, and environmental pollution is big, and the yield of lentinan is very low, only be 0.015%, cost is quite high, and the price of 1mg lentinan reaches more than 200 yuan, has greatly limited the clinical application of lentinan.So seeking the lentinan extracting and purifying method that a kind of technology is simple, productive rate is high, with low cost is the top priority of bringing into play the lentinan agent clinical effect better; help alleviating patient economy burden; to bring glad tidings to numerous cancer patientss; also help economizing on resources and protecting environment, will bring benefit to the mankind widely.
Summary of the invention
Task of the present invention provides a kind of new separation purification method of lentinan for injection, makes it have characteristics such as technology is simple, productive rate is high, with low cost.
Realize that technical scheme of the present invention is: lentinan for injection separation purification method provided by the invention is to adopt water extraction and alcohol precipitation method to obtain the lentinan crude product in conjunction with Tricholroacetic Acid method Deproteinization, the lentinan crude product through hydrogen peroxide decolour the decolouring polysaccharide, the decolouring polysaccharide get lentinan for injection through gel chromatography again.
The separation purification method of lentinan for injection provided by the invention may further comprise the steps:
A. get new fresh mushroom or dried thin mushroom, through powder essence or without powder essence;
B. adopt hot water extraction, concentrate;
C. ethanol sedimentation separates Crude polysaccharides;
D. Tricholroacetic Acid Deproteinization;
E. ethanol sedimentation;
F. hydrogen peroxide decolouring;
G. ethanol sedimentation;
H. gel chromatography removal of impurity polysaccharide and small molecules;
I. lyophilize.
Employing hot water extraction described in the above-mentioned steps, spissated concrete grammar is: add and be equivalent to 8 times of volume water of mushroom dry weight, boiling water extraction 2 times is concentrated into 2 times of volumes that are equivalent to the mushroom dry weight, gets concentrated solution; The concrete grammar that described ethanol sedimentation separates Crude polysaccharides is: add ethanol in concentrated solution, the solution alcohol concn is reached more than 50%, precipitation separation gets Crude polysaccharides; The concrete grammar of described Tricholroacetic Acid Deproteinization is: get Crude polysaccharides solution with the water dissolution Crude polysaccharides, 1～2 times of adding Crude polysaccharides liquor capacity, concentration are 5% trichloroacetic acid solution, get Deproteinization solution; Describedly in Deproteinization solution, add ethanol, the solution alcohol concn reached more than 50%, precipitation separation, the Deproteinization polysaccharide; The concrete grammar of described hydrogen peroxide decolouring is: the Deproteinization polysaccharide drips 30% superoxol with water dissolution, and transferring final concentration is 5～15%, and bath temperature is 40～60 ℃ of water-baths in the hydrogen peroxide decolouring, gets de-inking solution; The concrete grammar of the ethanol sedimentation after the described hydrogen peroxide decolouring is: in de-inking solution, adds ethanol, the solution alcohol concn reached more than 50%, and precipitation separation, polysaccharide must decolour; Described gel chromatography removal of impurity polysaccharide and micromolecular concrete grammar are: get the decolouring polysaccharide, with sephadex SephadexG-150 or Sephadex G-200 is stationary phase, 0.01～0.05M sodium-chlor or 0.01～0.05M sodium sulfate are moving phase, carry out gel chromatography separation, collect the lentinan component solution; Removal of impurity polysaccharide and small molecules; Described cryodesiccated concrete grammar is: the lentinan component solution of collecting is put freeze-drying in the freeze drier, get the white powder lentinan for injection.
The lentinan for injection that the present invention obtains is a white powder, and content is 98～102%, and weight-average molecular weight Mw is 400000～800000Da (see figure 2), and yield is 0.67% (calculating with finished product and dried thin mushroom mass ratio); Fourier infrared spectrum shows the characteristic absorbance of lentinan, and principal character is: at 3350～3300cm
-1The place for sugar ring go up the stretching vibration of O-H, at 2925～2915cm
-1The place for sugar ring go up the stretching vibration of C-H, at 1100～1000cm
-1The place for sugar ring go up the stretching vibration of C-O, at 898～884cm
-1The place is the C of β pyranose
1Fig. 1 is seen in-H flexural vibration.Above lentinan feature all meets national drug standards WS1-320 (X-263)-2004Z.
The content assaying method of lentinan for injection is: precision is measured lentinan reference substance and each 25mg of trial-product, adds the dissolving of 0.5mol/L sodium hydroxide solution respectively and is made into 25 μ gml
-1Reference substance solution and need testing solution; Precision is measured reference substance solution and need testing solution 2.5ml, slowly add in the test tube of accurate adding sulfuric acid anthrone solution 5ml along tube wall respectively, make layering (above operation is all carried out) in ice bath, after treating violent jolting mixing, put in the boiling water bath immediately and heat, from the jolting timing, accurate response 6 minutes, after test tube moved in the ice bath cooling, put to room temperature.From jolting, should be in 20～40 minutes, be blank with water, measure optical density according to spectrophotometry (two appendix IV of Chinese Pharmacopoeia version in 2005) at the wavelength place of 625nm, calculate promptly.
The weight-average molecular weight measuring method of lentinan for injection is:
Chromatographic condition: PL aquagel MIXED gel chromatographic columns (300mm * 7.5mm); Moving phase is the NaCl solution of 0.05M, pH7.0; Flow velocity 0.5mL/min; 30 ℃ of column temperatures; Sample size 25 μ L; Standard specimen is known molecular amount DEXTRAN (molecular weight 1000,100000,40000,70000,500000,2000000 Fluka companies); Detector is a differential refraction detector.
Measuring method: with the standard specimen dextran of sample and known molecular amount, make the solution that contains 10mg among every 1mL approximately with the moving phase dissolving respectively, inject 25 μ L standard solutions respectively, record differential color atlas, make typical curve with WATERS GPC software, calculate weight-average molecular weight and distribution thereof.
Separating and purifying lentinan method provided by the invention is compared with existing lentinan production technique, has productive rate height, pollution is little, cost is low advantage, is suitable for the suitability for industrialized production (seeing Table 1) of lentinan for injection.
The technology of table 1 lentinan relatively
Description of drawings
The Fourier infrared spectrum figure of the lentinan for injection that Fig. 1 obtains for the present invention;
Fig. 2 is the high performance liquid phase gel chromatography elution profile of lentinan for injection.
Embodiment
Embodiment 1
Take by weighing the 1000g mushroom fruiting body, shred, boiling water decocts 1, filters; The dregs of a decoction add water and boil 1h again, filter; Merge 2 times filtrate, concentrate; In concentrated solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, suction filtration after the standing over night, precipitation is put and is lower than 60 ℃ of dryings, gets crude product; Add 0.5M sodium hydroxide and make dissolving crude product, add 1～2 times of volume 5% Tricholroacetic Acid in solution, stir, placement is spent the night, suction filtration; Filtrate adjust pH to 6～8 add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn are reached more than 50%, and placement is spent the night, suction filtration, and precipitation is put and is lower than 60 ℃ of dryings, gets mushroom Crude polysaccharides 50g.
Get mushroom Crude polysaccharides 25.0g, be dissolved in water into dark brown brown solution; 40 ℃ of water-baths drip 30% superoxol, and transferring final concentration is 5～15%, treat that solution colour becomes to stop water-bath after faint yellow; In solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, occur milky white precipitate, standing over night immediately; The supernatant that inclines, decompress filter, precipitation is with ethanol/ether/washing with acetone for several times, and is colourless until filtrate, pale precipitation; Precipitation is put and is lower than 60 ℃ of dryings, gets white block 9.6g.
Get decolouring polysaccharide 100mg, add the dissolving of 0.01～0.05M sodium-chlor, polysaccharide concentration 〉=10mg/ml, solution are milky white solution; The gel chromatography elution requirement is: filler: Sephadex G-150, and chromatographic column is 2.5cm (diameter) * 40cm (highly), gel height of bed 35cm; Elutriant is 0.01～0.05M sodium-chlor, flow velocity 0.4ml/min; Applied sample amount≤50ml; Collecting elution volume is the component of 30～60ml, merges solution, puts freeze-drying in the freeze drier, gets white floss 30～40mg.
Embodiment 2
Take by weighing the 1000g mushroom fruiting body, pulverize, boiling water decocts 1h, filters; The dregs of a decoction add water and boil 1h again, filter; Merge 2 times filtrate, concentrate; In concentrated solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, suction filtration after the standing over night, precipitation is put and is lower than 60 ℃ of dryings, gets crude product; Add 0.5M sodium hydroxide and make dissolving crude product, add 1～2 times of volume 5% Tricholroacetic Acid in solution, stir, placement is spent the night, suction filtration; Filtrate adjust pH to 6～8 add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn are reached more than 50%, and placement is spent the night, suction filtration, and precipitation is put and is lower than 60 ℃ of dryings, gets mushroom Crude polysaccharides 50g.
Get mushroom Crude polysaccharides 25.0g, be dissolved in water into dark brown brown solution; 50 ℃ of water-baths drip 30% superoxol, and transferring final concentration is 5～15%, treat that solution colour becomes to stop water-bath after faint yellow; In solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, occur milky white precipitate, standing over night immediately; The supernatant that inclines, decompress filter, precipitation is with ethanol/ether/washing with acetone for several times, and is colourless until filtrate, pale precipitation; Precipitation is put and is lower than 60 ℃ of dryings, gets white block 9.6g.
Get decolouring polysaccharide 100mg, add the dissolving of 0.01～0.05M sodium-chlor, polysaccharide concentration 〉=10mg/ml, solution are milky white solution; The gel chromatography elution requirement is: filler: Sephadex G-150, and chromatographic column is 2.5cm (diameter) * 40cm (highly), gel height of bed 35cm; Elutriant is 0.01～0.05M sodium-chlor, flow velocity 0.4ml/min; Applied sample amount≤50ml; Collecting elution volume is the component of 30～60ml, merges solution, puts freeze-drying in the freeze drier, gets white floss 30～40mg.
Embodiment 3
Take by weighing the 1000g mushroom fruiting body, pulverize, boiling water decocts 1h, filters; The dregs of a decoction add water and boil 1h again, filter; Merge 2 times filtrate, concentrate; In concentrated solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, suction filtration after the standing over night, precipitation is put and is lower than 60 ℃ of dryings, gets crude product; Add 0.5M sodium hydroxide and make dissolving crude product, add 1～2 times of volume 5% Tricholroacetic Acid in solution, stir, placement is spent the night, suction filtration; Filtrate adjust pH to 6～8 add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn are reached more than 50%, and placement is spent the night, suction filtration, and precipitation is put and is lower than 60 ℃ of dryings, gets mushroom Crude polysaccharides 50g.
Get mushroom Crude polysaccharides 25.0g, be dissolved in water into dark brown brown solution; 60 ℃ of water-baths drip 30% superoxol, and transferring final concentration is 5～15%, treat that solution colour becomes to stop water-bath after faint yellow; In solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, occur milky white precipitate, standing over night immediately; The supernatant that inclines, decompress filter, precipitation is with ethanol/ether/washing with acetone for several times, and is colourless until filtrate, pale precipitation; Precipitation is put and is lower than 60 ℃ of dryings, gets white block 9.6g.
Get decolouring polysaccharide 100mg, add the dissolving of 0.01～0.05M sodium-chlor, polysaccharide concentration 〉=10mg/ml, solution are milky white solution; The gel chromatography elution requirement is: filler: Sephadex G-200, and chromatographic column is 2.5cm (diameter) * 40cm (highly), gel height of bed 35cm; Elutriant is 0.01～0.05M sodium-chlor, flow velocity 0.4ml/min; Applied sample amount≤50ml; Collecting elution volume is the component of 30～60ml, merges solution, puts freeze-drying in the freeze drier, gets white floss 30～40mg.
Embodiment 4
Take by weighing the 1000g mushroom fruiting body, pulverize, boiling water decocts 1h, filters; The dregs of a decoction add water and boil 1h again, filter; Merge 2 times filtrate, concentrate; In concentrated solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, suction filtration after the standing over night, precipitation is put and is lower than 60 ℃ of dryings, gets crude product; Add 0.5M sodium hydroxide and make dissolving crude product, add 1～2 times of volume 5% Tricholroacetic Acid in solution, stir, placement is spent the night, suction filtration; Filtrate adjust pH to 6～8 add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn are reached more than 50%, and placement is spent the night, suction filtration, and precipitation is put and is lower than 60 ℃ of dryings, gets mushroom Crude polysaccharides 50g.
Get mushroom Crude polysaccharides 25.0g, be dissolved in water into dark brown brown solution; 40 ℃ of water-baths drip 30% superoxol, and transferring final concentration is 5～15%, treat that solution colour becomes to stop water-bath after faint yellow; In solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, occur milky white precipitate, standing over night immediately; The supernatant that inclines, decompress filter, precipitation is with ethanol/ether/washing with acetone for several times, and is colourless until filtrate, pale precipitation; Precipitation is put and is lower than 60 ℃ of dryings, gets white block 9.6g.
Get decolouring polysaccharide 100mg, add the dissolving of 0.01～0.05M sodium sulfate, polysaccharide concentration 〉=10mg/ml, solution are milky white solution; The gel chromatography elution requirement is: filler: Sephadex G-200, and chromatographic column is 2.5cm (diameter) * 40cm (highly), gel height of bed 35cm; Elutriant is 0.01～0.05M sodium sulfate, flow velocity 0.4ml/min; Applied sample amount≤50ml; Collecting elution volume is the component of 30～60ml, merges solution, puts freeze-drying in the freeze drier, gets white floss 30～40mg.
Take by weighing the 1000g mushroom fruiting body, shred, boiling water decocts 1h, filters; The dregs of a decoction add water and boil 1h again, filter; Merge 2 times filtrate, concentrate; In concentrated solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, suction filtration after the standing over night, precipitation is put and is lower than 60 ℃ of dryings, gets crude product; Add 0.5M sodium hydroxide and make dissolving crude product, add 1～2 times of volume 5% Tricholroacetic Acid in solution, stir, placement is spent the night, suction filtration; Filtrate adjust pH to 6～8 add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn are reached more than 50%, and placement is spent the night, suction filtration, and precipitation is put and is lower than 60 ℃ of dryings, gets mushroom Crude polysaccharides 50g.
Get mushroom Crude polysaccharides 25.0g, be dissolved in water into dark brown brown solution; 50 ℃ of water-baths drip 30% superoxol, and transferring final concentration is 5～15%, treat that solution colour becomes to stop water-bath after faint yellow; In solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, occur milky white precipitate, standing over night immediately; The supernatant that inclines, decompress filter, precipitation is with ethanol/ether/washing with acetone for several times, and is colourless until filtrate, pale precipitation; Precipitation is put and is lower than 60 ℃ of dryings, gets white block 9.6g.
Get decolouring polysaccharide 100mg, add the dissolving of 0.01～0.05M sodium-chlor, polysaccharide concentration 〉=10mg/ml, solution are milky white solution; The gel chromatography elution requirement is: filler: Sephadex G-150, and chromatographic column is 2.5cm (diameter) * 40cm (highly), gel height of bed 35cm; Elutriant is 0.01～0.05M sodium-chlor, flow velocity 0.4ml/min; Applied sample amount≤50ml; Collecting elution volume is the component of 30～60ml, merges solution, puts freeze-drying in the freeze drier, gets white floss 30～40mg.
Embodiment 6
Take by weighing the 1000g mushroom fruiting body, shred, boiling water decocts 1h, filters; The dregs of a decoction add water and boil 1h again, filter; Merge 2 times filtrate, concentrate; In concentrated solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, suction filtration after the standing over night, precipitation is put and is lower than 60 ℃ of dryings, gets crude product; Add 0.5M sodium hydroxide and make dissolving crude product, add 1～2 times of volume 5% Tricholroacetic Acid in solution, stir, placement is spent the night, suction filtration; Filtrate adjust pH to 6～8 add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn are reached more than 50%, and placement is spent the night, suction filtration, and precipitation is put and is lower than 60 ℃ of dryings, gets mushroom Crude polysaccharides 50g.
Get mushroom Crude polysaccharides 25.0g, be dissolved in water into dark brown brown solution; 60 ℃ of water-baths drip 30% superoxol, and transferring final concentration is 5～15%, treat that solution colour becomes to stop water-bath after faint yellow; In solution, slowly add dehydrated alcohol/95% ethanol/75% ethanol the solution alcohol concn is reached more than 50%, occur milky white precipitate, standing over night immediately; The supernatant that inclines, decompress filter, precipitation is with ethanol/ether/washing with acetone for several times, and is colourless until filtrate, pale precipitation; Precipitation is put and is lower than 60 ℃ of dryings, gets white block 9.6g.
Get decolouring polysaccharide 100mg, add the dissolving of 0.01～0.05M sodium sulfate, polysaccharide concentration 〉=10mg/ml, solution are milky white solution; The gel chromatography elution requirement is: filler: Sephadex G-150, and chromatographic column is 2.5cm (diameter) * 40cm (highly), gel height of bed 35cm; Elutriant is 0.01～0.05M sodium sulfate, flow velocity 0.4ml/min; Applied sample amount≤50ml; Collecting elution volume is the component of 30～60ml, merges solution, puts freeze-drying in the freeze drier, gets white floss 30～40mg.
Claims (9)
1. the separation purification method of lentinan for injection is characterized in that, may further comprise the steps:
A. get new fresh mushroom or dried thin mushroom, through powder essence or without powder essence;
B. adopt hot water extraction, concentrate;
C. ethanol sedimentation separates Crude polysaccharides;
D. Tricholroacetic Acid Deproteinization;
E. ethanol sedimentation;
F. hydrogen peroxide decolouring;
G. ethanol sedimentation;
H. gel chromatography removal of impurity polysaccharide and small molecules;
I. lyophilize.
2. the separation purification method of lentinan for injection according to claim 1 is characterized in that, described employing hot water extraction, spissated concrete grammar is: add and be equivalent to 8 times of volume water of mushroom dry weight, boiling water extraction 2 times is concentrated into 2 times of volumes that are equivalent to the mushroom dry weight, gets concentrated solution.
3. the separation purification method of lentinan for injection according to claim 1, it is characterized in that the concrete grammar that described ethanol sedimentation separates Crude polysaccharides is: add ethanol in concentrated solution, the solution alcohol concn is reached more than 50%, precipitation separation gets Crude polysaccharides.
4. the separation purification method of lentinan for injection according to claim 1, it is characterized in that, the concrete grammar of described Tricholroacetic Acid Deproteinization is: get Crude polysaccharides solution with the water dissolution Crude polysaccharides, 1～2 times of adding Crude polysaccharides liquor capacity, concentration are 5% trichloroacetic acid solution, get Deproteinization solution.
5. the separation purification method of lentinan for injection according to claim 1 is characterized in that, describedly adds ethanol in Deproteinization solution, and the solution alcohol concn is reached more than 50%, precipitation separation, the Deproteinization polysaccharide.
6. the separation purification method of lentinan for injection according to claim 1, it is characterized in that, the concrete grammar of described hydrogen peroxide decolouring is: the Deproteinization polysaccharide is with water dissolution, drip 30% superoxol, transferring final concentration is 5～15%, bath temperature is 40～60 ℃ of water-baths in the hydrogen peroxide decolouring, gets de-inking solution.
7. the separation purification method of lentinan for injection according to claim 1, it is characterized in that the concrete grammar of the ethanol sedimentation after the described hydrogen peroxide decolouring is: add ethanol in de-inking solution, the solution alcohol concn is reached more than 50%, precipitation separation, polysaccharide must decolour.
8. the separation purification method of lentinan for injection according to claim 1, it is characterized in that, described gel chromatography removal of impurity polysaccharide and micromolecular concrete grammar are: get the decolouring polysaccharide, with sephadex SephadexG-150 or Sephadex G-200 is stationary phase, 0.01～0.05M sodium-chlor or 0.01～0.05M sodium sulfate are moving phase, carry out gel chromatography separation, collect the lentinan component solution; Removal of impurity polysaccharide and small molecules.
9. the separation purification method of lentinan for injection according to claim 1, it is characterized in that, described cryodesiccated concrete grammar is: the lentinan component solution of collecting is put freeze-drying in the freeze drier, get the white powder lentinan for injection.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102408495A (en) * | 2011-12-29 | 2012-04-11 | 武汉大学 | Champignon beta-glucan having anti-inflammation activity, and preparation method and application thereof |
| CN103599125A (en) * | 2013-11-22 | 2014-02-26 | 吉林大学 | Anti-radiation and assistant anti-tumor drug and application |
| CN103837671A (en) * | 2012-11-26 | 2014-06-04 | 天士力制药集团股份有限公司 | Method for measuring free polysaccharide content in polysaccharide protein conjugate |
| CN109682893A (en) * | 2017-10-19 | 2019-04-26 | 上海慈瑞通鑫医药技术有限公司 | The measuring method of lentinan content in lentinan composition |
-
2008
- 2008-08-07 CN CN200810048721A patent/CN101643515A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102408495A (en) * | 2011-12-29 | 2012-04-11 | 武汉大学 | Champignon beta-glucan having anti-inflammation activity, and preparation method and application thereof |
| CN102408495B (en) * | 2011-12-29 | 2013-09-18 | 武汉大学 | Champignon beta-glucan having anti-inflammation activity, and preparation method and application thereof |
| CN103837671A (en) * | 2012-11-26 | 2014-06-04 | 天士力制药集团股份有限公司 | Method for measuring free polysaccharide content in polysaccharide protein conjugate |
| CN103599125A (en) * | 2013-11-22 | 2014-02-26 | 吉林大学 | Anti-radiation and assistant anti-tumor drug and application |
| CN109682893A (en) * | 2017-10-19 | 2019-04-26 | 上海慈瑞通鑫医药技术有限公司 | The measuring method of lentinan content in lentinan composition |
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