CN104292351A - Phellinus ribis polysaccharide, as well as preparation method and applications thereof - Google Patents
Phellinus ribis polysaccharide, as well as preparation method and applications thereof Download PDFInfo
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Abstract
The invention discloses a phellinus ribis polysaccharide, as well as a preparation method and applications thereof, belonging to the field of polysaccharides. The prepared phellinus ribis polysaccharide is novel in structure and obtained through separation for the first time; the structure of the phellinus ribis polysaccharide contains a repeatable unit structure which has a main chain comprising three (1.3)-beta-D-glucoses, one branch is at C6 position of one of three (1.3)-beta-D-glucoses in the main chain and is formed by connecting three (1.6)-beta-D-glucoses in series. The invention further discloses a preparation method of the phellinus ribis polysaccharide, the method is simple and applicable, and the purity of the extracted polysaccharide is higher than 93%, and the prepared polysaccharide can be used for preparing a medicament for treating neurodegenerative diseases such as alzheimer disease.
Description
Technical field
The present invention relates to polysaccharide field, be specifically related to a kind of currant Phellinus polysaccharide and its preparation method and application.
Background technology
Alzheimer's disease is that a kind of what occur in the senium take progressive dementia as the ofneurodegenerative diseases of principal character.Along with world population aging increasingly, onset of Alzheimer disease rate is more and more higher, and become the fourth-largest killer after cardiovascular disorder, cancer and apoplexy, the healthy of the elderly and quality of life in serious harm.The medicine being used for the treatment of alzheimer's disease at present probably has more than 10 to plant, mainly cholinomimetic thing and the nootropics improving brain metabolism, wherein vagusstoff enzyme inhibitors (cholinomimetic) is the first-line drug for the treatment of alzheimer's disease at present, as tacrine (Tacrine), donepezil (Donepezil), profit this bright (Rivastigmine), lycoremine (Galanthamine) and huperzine first-class.These medicines applied clinically can only alleviate the cognitive disorder of early stage patient, provide the symptom improvement result of appropriateness, cannot stop the progress of the state of an illness.Up to the present, the active drug of etiological treatment and control disease process is still lacked.
Nerve growth factor (nerve growth factor; NGF); as member most important in neurotrophic factor family; there is potential provide protection to the regeneration of the dopaminergic neuron cell of degenerating and promotion striatal dopamine neuron cell, be expected to cure alzheimer's disease.But as protein matter, there is the shortcomings such as unstable chemcial property, Half-life in vivo is short, pharmacokinetic properties is not good enough, and not easily pass through hemato encephalic barrier in NGF, and expensive, limits the application that it is clinical.Therefore, actively find the treatment that other compounds with neurotrophic " NGF " sample are used for alzheimer's disease to have great importance.
Currant Phellinus polysaccharide is from medicinal fungi currant Phellinus (Phellinus ribis), be separated the homogeneous polysaccharide component with neurotrophic activity obtained, research shows the growth of its PC12 spinous process that can significantly promote NGF to mediate within the scope of 10 μ g/ml-150 μ g/ml, is expected the drug candidate being developed to the nerve degenerative diseases treatments such as alzheimer's disease.Research about currant Phellinus polysaccharide neurotrophic effect did not have relevant report before the present invention completes.
Summary of the invention
The object of the present invention is to provide a kind of currant Phellinus polysaccharide with pharmaceutical use and its preparation method and application.Currant Phellinus polysaccharide of the present invention, novel structure is separated first to obtain, called after PRG; Its preparation method is simple, applicable, and the purity of polysaccharide of extraction is up to more than 93%.This product can be used for the medicine preparing the nerve degenerative diseases such as treatment alzheimer's disease.
The present invention is by the following technical solutions:
A kind of currant Phellinus polysaccharide, it is characterized in that, its monose consists of β-D-Glucose, and having in its structure can repeat unit structure; Describedly can form main chain by 3 (1 → 3)-β-D-Glucoses by repeat unit structure, a branch is had in the C6 position of one of them (1 → 3)-β-D-Glucose of main chain, branch is in series by 3 (1 → 6)-β-D-Glucoses, and its repeat unit structure formula is as follows:
。
In described currant Phellinus polysaccharide, the component molar ratio of terminal glucose, (1 → 3)-β-D-Glucose, (1 → 6)-β-D-Glucose and (1 → 3,6)-β-D-Glucose is about 1:2:2:1;
Described currant Phellinus polysaccharide, weight-average molecular weight is 5.16 × 10
3da, specific rotatory power+32.1 ° (
c0.1, H
2o).
A preparation method for currant Phellinus polysaccharide, it is characterized in that, it comprises the following steps:
(1) water extraction: get currant Phellinus sporophore meal, add the distilled water of 20 times of-40 times of weight, 90 DEG C-100 DEG C are extracted 4 times, each 4h-6h, filter, merging filtrate, concentrated, add ethanol to alcohol content 80%, leave standstill 24h, centrifugal, obtain currant Phellinus total polysaccharides crude product;
(2) Deproteinization: the total polysaccharides crude product of step (1) gained is dissolved in distilled water, with protease hydrolyzed, deactivation centrifugal removing metaprotein enzyme, centrifugal gained supernatant liquor adds organic solvent, vibration, centrifugal, except sub-cloud organic phase and middle protein layer, repeat the step of organic solvent process until produce without white precipitate, obtain the polysaccharide Aqueous extracts after Deproteinization;
(3) classification alcohol precipitation: the Aqueous extracts in step (2) is concentrated, add ethanol to alcohol content 50%, centrifugal, discard throw out, supernatant liquor continues to add ethanol to alcohol content 80%, leaves standstill, centrifugal, throw out uses dehydrated alcohol, washing with acetone successively, vacuum-drying, obtains currant Phellinus classification polysaccharide crude;
(4) column chromatography: through DEAE-cellulose chromatography after currant Phellinus classification polysaccharide crude step (3) obtained dissolves, phend-sulphuric acid detects polysaccharide, to collect it after the elutriant of the second elution peak again through gel filtration chromatography, phend-sulphuric acid detects polysaccharide, collect the elutriant of main peak, elutriant is through concentrating, dialyse and obtaining currant Phellinus polysaccharide of the present invention after freeze-drying.
In above-mentioned steps (1), described centrifugal speed is 3000rpm-4000rpm, and the time is 15min-30min;
In above-mentioned steps (1), add the distilled water of currant Phellinus 30 times of weight, Extracting temperature is 95 DEG C, and extraction time is each 6h, and centrifugal speed is 3000rpm, and centrifugation time is 20min.
In above-mentioned steps (2), described proteolytic enzyme is trypsinase; Described organic solvent is chloroform and propyl carbinol, and the volume ratio of described chloroform and propyl carbinol is 5:1.
In above-mentioned steps (3), described ethanol is dehydrated alcohol; Centrifugal speed is 3000rpm, and centrifugation time is 20min.
In above-mentioned steps (4), the condition of described DEAE-cellulose chromatography is: stepwise elution, and elutriant is followed successively by distilled water, 0.05mol/L NaCl solution, 0.1mol/L NaCl solution and 0.2mol/L NaCl solution, and flow velocity is 2ml/min.
In above-mentioned steps (4), described gel is Superdex 30, and gel permeation chromatography condition is: elutriant is 0.05mol/L NaCl solution, and flow velocity is 0.5ml/min.
Described currant Phellinus polysaccharide can be applied in the medicine for the treatment of nerve degenerative diseases.
Tool of the present invention has the following advantages:
Currant Phellinus polysaccharide (PRG) of the present invention is separated first to obtain from currant Phellinus, is the dextran of a new novel structure.PRG is by terminal glucose, 1 → 3 glucose connected, 1 → 6 glucose and 1 → 3 connected, and the 6 glucose compositions connected, component molar is than being 1:2:2:1.IR proves that PRG is carbohydrate, is beta configuration.This polysaccharide weight-average molecular weight 5.16 × 10
3da, specific rotatory power+32.1 ° (
c0.1, H
2o).
The growth of the PC12 spinous process that PRG can promote NGF to mediate, has stronger neurotrophic activity, for studying discovery first, can be used for the medicine preparing nerve degenerative diseases treatment.This active polysaccharide has no report before making the present invention.
Accompanying drawing explanation
Fig. 1 is the HPSEC-MALLS color atlas of PRG.
Fig. 2 is that PRG is at 200nm-400nm UV scanning collection of illustrative plates.
Fig. 3 is that standard monose sugar nitrile acetic ester derives rear gas chromatogram.
Fig. 4 is the gas chromatogram after PRG hydrolysate sugar nitrile acetic ester derives.
Fig. 5 is the infrared spectra of PRG.
Fig. 6 is the nmr spectrum (a) of PRG
1h NMR, (b)
1c NMR, (c) DEPT.
Fig. 7 is PC12 morphological observation.
Fig. 8 is the quantitative analysis that PRG promotes the exsule length of PC12 cellular neural.
Embodiment
Below in conjunction with specific embodiment, the present invention is described further.
Embodiment 1
The preparation of currant Phellinus polysaccharide, it comprises the following steps:
(1) water extraction: currant Phellinus fruit body powder is broken into meal, add 30 times amount distilled water (g/ml), after mixing in thermostat water bath 95 DEG C extract 4 times, each 6h, gauze filter, merge Aqueous extracts, concentrated, add the dehydrated alcohol of 4 times of Aqueous extracts volumes, leave standstill 24h, the centrifugal 20min of 3000rpm, obtains currant Phellinus total polysaccharides crude product.
(2) Deproteinization: the currant Phellinus total polysaccharides crude product of step (1) gained is dissolved in distilled water, obtain the currant Phellinus Crude polysaccharides aqueous solution, add the proteolytic enzyme of Crude polysaccharides weight 1%, 45 ° of C water-bath 8 h, then be warming up to 90 ° of C and maintain 10 min inactivators, be cooled to room temperature, the centrifugal 30min of 5000rpm removes metaprotein and enzyme, Sevag reagent (chloroform and the propyl carbinol of 1/4th supernatant volume is added at centrifugal gained supernatant liquor, wherein the volume ratio of chloroform and propyl carbinol is 5:1), thermal agitation 15min, centrifugal except sub-cloud organic phase and middle protein layer, repeat by Sevag agent treated step until produce without white precipitate, obtain the polysaccharide Aqueous extracts after Deproteinization.
(3) classification alcohol precipitation: Aqueous extracts step (2) obtained concentrates, add the dehydrated alcohol of 1 times of volume to alcohol content 50%, stirring and evenly mixing, static 24h, the centrifugal 20min of 3000rpm, discard throw out, supernatant liquor continues to add dehydrated alcohol to alcohol content 80%, leaves standstill 24h, the centrifugal 20min of 3000rpm, throw out uses dehydrated alcohol, washing with acetone successively, vacuum-drying, obtains currant Phellinus classification polysaccharide crude.
(4) column chromatography: currant Phellinus classification polysaccharide crude distilled water step (3) obtained dissolves the aqueous solution obtaining 20mg/ml; First with distilled water balance DEAE-cellulose ion-exchange chromatography post (4.5cm × 30cm), by the currant Phellinus classification polysaccharide crude aqueous solution through DEAE-cellulose ion-exchange column chromatography, applied sample amount 5ml, flow velocity 2ml/min, elutriant is followed successively by distilled water, 0.05mol/L NaCl solution, 0.1mol/L NaCl solution and 0.2mol/L NaCl solution, stepwise elution, the elutriant phend-sulphuric acid of collection detects polysaccharide, collects the elutriant of the second elution peak;
The elutriant of the second elution peak collected is further purified through gel permeation chromatography (Superdex 30), the specification of chromatography column is 1.8cm × 80cm, applied sample amount 2ml, elutriant is 0.05mol/L NaCl solution, flow velocity is 0.5ml/min, elutriant phend-sulphuric acid collected by gel permeation chromatography detects polysaccharide, collect the elutriant of the main peak containing polysaccharide, through concentrated, aperture is that after the dialysis tubing dialysis of 2000Da, freeze-drying obtains the cotton-shaped homogeneous currant Phellinus polysaccharide of white loose, called after PRG.
Embodiment 2
PRG purity detecting and molecular weight determination
By currant Phellinus polysaccharide PRG obtained for embodiment 1, high performance liquid chromatography coupling multiple angle laser light scattering is adopted to measure purity and molecular weight.Chromatographic column is that G3000 PWXL and G4000 PWXL two tsk gel posts are used in conjunction, and be equipped with differential refraction and multiple angle laser light scattering detector, moving phase is 0.2M NaNO
3.Sample 0.2M NaNO
3be mixed with the concentration of 1mg/ml, 0.22 μm of filter membrane filters, and sample introduction 200 μ l, flow velocity is 0.6 ml/min.Record chromatographic peak, as Fig. 1, is shown as symmetrical simple spike, and illustrate that PRG homogeneity is good, recording its weight-average molecular weight is 5.16 × 10
3da.
Embodiment 3
PRG component detects
By currant Phellinus polysaccharide PRG obtained for embodiment 1, detecting total sugar content with phend-sulphuric acid is 98.1%, detects not containing albumen with Coomassie Brilliant Blue (Bradford method), and between using, hydroxyl phynol method detects not containing uronic acid.The 1mg/ml aqueous solution carries out 200nm-400nm UV scanning, the results are shown in Figure 2, at 260nm and 280nm place, does not have obvious absorption peaks, illustrates in this sample not containing nucleic acid and albumen.
Embodiment 4
PRG monose forms
Take currant Phellinus polysaccharide PRG 10 mg that embodiment 1 is obtained, add the trifluoroacetic acid 6ml of 2 mol/L, fill N
2rear sealing, 110 ° of C are hydrolyzed 3 hours, produce, and 60 ° of C are evaporated to dry.Add methyl alcohol a little, evaporate to dryness, repeats 3 ~ 5 times, to steam TFA completely.Hydrolysate vacuum-drying 12h, adds the oxammonium hydrochloride of 5mg, 0.3ml pyridine and 4mg inositol (interior mark), 90 ° of C stirring reaction 30min.Be chilled to room temperature after taking-up, add the acetic anhydride of 0.8ml, continue reaction 30min under 90 ° of C and carry out acetylize, reaction product directly carries out gas chromatographic analysis.Another label taking accurate monose wood sugar, seminose, glucose and semi-lactosi for derivative, carry out gas chromatographic analysis by upper legal system.
Gas phase analysis chromatographiccondition is injection port: split-splitless, temperature 250 ° of C; Chromatography column: DB-5 quartz capillary column, 0.25m × 0.25mm × 30m, flow 1mL/min; Heating schedule: 120 ° of C keep 3min, to heat up 8 ° of C to 250 ° of C per minutes, 250 ° of C keep 10min; Mass spectrum: EI source, ionization voltage 70eV; Detector: fid detector, temperature 220 ° of C, carrier gas He; Sample size: 0.5l, splitting ratio 30:1, sweep limit 20 ~ 600aum.
Result is as Fig. 3 and Fig. 4, and by contrasting with standard monose, PRG monose consists of glucose, illustrates that currant Phellinus polysaccharide PRG is dextran.
Embodiment 5
PRG infrared spectra detects
Get dry PRG1.0mg, with KBr compressing tablet, at 4000 cm
-1-400cm
-1scope in carry out Infrared spectrum scanning, record infrared spectrogram.
As Fig. 5, at 1730cm
-1left and right does not have the charateristic avsorption band of uronic acid, at 810cm
-1and 870cm
-1place does not have the charateristic avsorption band of seminose yet, shows not containing uronic acid and seminose.1200 ~ 1000cm
-1the monose locating strong absorption peak prompting PRG is pyranoid ring type.At 3396.31cm
-1the broad peak that place's appearance one is stronger is the stretching vibration of hydroxyl (-OH); At 2892.41cm
-1the absorption peak that place occurs is more weak, is the stretching vibration of C-H.1612.98cm
-1the absorption peak at place is because the water in sample causes; At 896.72cm
-1the absorption peak that place can observe shows that the glycosidic link in PRG is beta configuration.
Embodiment 6
PRG magnetic resonance detection
Get PRG30mg, 50 ° of C vacuum-drying 24h, are dissolved in 0.5ml D
2in O, Bruker Avance 600 MHz spectrometer measures it
1h NMR and
13c NMR composes, and is interior mark (δ with DSS
h0.00ppm, δ
c21.74ppm), measuring temperature is 40 ° of C.
1h NMR is as Fig. 6 (a).In the different head region of 4.5 ~ 5.5ppm, have four peaks, respectively at δ 4.39, δ 4.40, δ 4.60 and δ 4.65 place, prompting may have the mode of connection of four kinds of glycosidic links; Its chemical displacement value is all less than 4.9, illustrates that in PRG, the configuration of glycosidic link is β type.The H signal at 3.2 ~ 4.2ppm place is H-2 ~ H-6 proton on sugared ring, and chemical displacement value is close, overlapping serious.
PRG's
13c NMR is shown in Fig. 6 (b).Have no carbonyl carbon signals at 160 ~ 180ppm place, show this polysaccharide not containing uronic acid and glycoprotein, δ <20ppm place has no carbon signal, illustrates in PRG not containing methyl sugar.There are four fignal centers in the low place of 95 ~ 100ppm, is anomeric carbon, and its chemical shift is δ 102.44, δ 102.72, δ 102.81 and δ 102.88 respectively, with
1four anomer hydrogen fignal centers during H NMR composes are corresponding, and the mode of connection really containing four kinds of glycosidic links in the basic repeating unit of composition PRG is described, chemical displacement value is greater than 102ppm proves that monosaccharide residue is configured as β type further.The fignal center of four anomeric carbons and anomeric proton is 1 → 6,1 → 3,1 → 3 respectively, 6 and the fignal center of terminal glucose.The signal of chemical shift in 60 ~ 90ppm region is C-2 ~ C-6 signal on sugared ring, wherein the δ 83.90 of lower field, δ 84.54 signal are 1 → 3, the C-3 in 1 → 3,6 glucosyl residues connected, shift to low field owing to becoming glycosides, do not become the C-3 of glycosides to be positioned at 75 ~ 78ppm chemical shift place; δ 60.61, the δ 62.44 of high field are unsubstituted C-6, the glucosyl residue signal that terminal glucose saccharide residue is connected with 1 → 3 respectively, according to glycosidation displacement rule, the C-6 signal that instead of will shift to low field, be positioned near 70.00ppm, this signal can be composed [Fig. 6 (c)] from DEPT and be recognized, wherein namely the inverted peaks (CH2) at 68.62ppm place is the C-6 signal in the glucosyl residues of 1 → 6 connection and 1 → 3,6 connections.Concrete structure unit is as shown in structural formula.
Embodiment 7
PRG neurotrophic activity measures
The present invention have detected the neurotrophic activity of the obtained currant Phellinus polysaccharide PRG of embodiment 1.
Adopt PC12 raji cell assay Raji neurite outgrowth promoter action.The PC12 cell of taking the logarithm vegetative period, with the DMEM suspension cell containing 10% horse serum and 5% foetal calf serum, counting, with every hole 8 × 10
3individual cell is inoculated in 24 well culture plates, every pore volume 400 μ l, at 37 DEG C, and 5%CO
2after 24 h cultivated by incubator, replace original substratum, then add the sample solution of 1 ng/ml NGF and different concns with the DMEM containing 2% horse serum and 1% foetal calf serum, each concentration arranges 3 multiple holes.Continue cultivation after 4 days, 4% paraformaldehyde is fixed, methylene blue staining, basis of microscopic observation.
Morphological observations is as Fig. 7, and under the NGF of 1ng/ml exists, PRG can promote the growth of neural axon.Carry out quantitative analysis, the results are shown in Figure 8, when 10 μ g/ml, 50 μ g/ml, 150 μ g/ml concentration, the mean length of PC12 cellular neural aixs cylinder is respectively 40.9 μm, 54.3 μm and 58.4 μm, compares have significant difference with control group (mean length is 32.7 μm).Illustrate that currant Phellinus polysaccharide PRG has significant neurotrophic activity, treatment nerve degenerative diseases can be developed as the drug candidate of A Ermoci disease.
Claims (10)
1. a currant Phellinus polysaccharide, is characterized in that, its monose consists of β-D-Glucose, and having in its structure can repeat unit structure; Describedly can form main chain by 3 (1 → 3)-β-D-Glucoses by repeat unit structure, a branch is had in the C6 position of one of them (1 → 3)-β-D-Glucose of main chain, branch is in series by 3 (1 → 6)-β-D-Glucoses, and its repeat unit structure formula is as follows:
。
2. currant Phellinus polysaccharide according to claim 1, it is characterized in that, in described currant Phellinus polysaccharide, the component molar ratio of terminal glucose, (1 → 3)-β-D-Glucose, (1 → 6)-β-D-Glucose and (1 → 3,6)-β-D-Glucose is about 1:2:2:1; Described currant Phellinus polysaccharide, weight-average molecular weight is 5.16 × 10
3da.
3. a preparation method for currant Phellinus polysaccharide according to claim 1, it is characterized in that, it comprises the following steps:
(1) water extraction: get currant Phellinus sporophore meal, add the distilled water of 20 times of-40 times of weight, 90 DEG C-100 DEG C are extracted 4 times, each 4h-6h, filter, merging filtrate, concentrated, add ethanol to alcohol content 80%, leave standstill 24h, centrifugal, obtain currant Phellinus total polysaccharides crude product;
(2) Deproteinization: the total polysaccharides crude product of step (1) gained is dissolved in distilled water, with protease hydrolyzed, deactivation centrifugal removing metaprotein enzyme, centrifugal gained supernatant liquor adds organic solvent, vibration, centrifugal, except sub-cloud organic phase and middle protein layer, repeat the step of organic solvent process until produce without white precipitate, obtain the polysaccharide Aqueous extracts after Deproteinization;
(3) classification alcohol precipitation: the Aqueous extracts in step (2) is concentrated, add ethanol to alcohol content 50%, centrifugal, discard throw out, supernatant liquor continues to add ethanol to alcohol content 80%, leaves standstill, centrifugal, throw out uses dehydrated alcohol, washing with acetone successively, vacuum-drying, obtains currant Phellinus classification polysaccharide crude;
(4) column chromatography: through DEAE-cellulose chromatography after currant Phellinus classification polysaccharide crude step (3) obtained dissolves, phend-sulphuric acid detects polysaccharide, to collect it after the elutriant of the second elution peak again through gel filtration chromatography, phend-sulphuric acid detects polysaccharide, collect the elutriant of main peak, elutriant is through concentrating, dialyse and obtaining currant Phellinus polysaccharide of the present invention after freeze-drying.
4. the preparation method of currant Phellinus polysaccharide according to claim 3, is characterized in that, in step (1), described centrifugal speed is 3000rpm-4000rpm, and the time is 15min-30min.
5. the preparation method of currant Phellinus polysaccharide according to claim 4, is characterized in that, in step (1), add the distilled water of currant Phellinus 30 times of weight, Extracting temperature is 95 DEG C, and extraction time is each 6h, centrifugal speed is 3000rpm, and centrifugation time is 20min.
6. the preparation method of currant Phellinus polysaccharide according to claim 3, is characterized in that, in step (2), described proteolytic enzyme is trypsinase; Described organic solvent is chloroform and propyl carbinol, and the volume ratio of described chloroform and propyl carbinol is 5:1.
7. the preparation method of currant Phellinus polysaccharide according to claim 3, is characterized in that, in step (3), described ethanol is dehydrated alcohol; Centrifugal speed is 3000rpm, and centrifugation time is 20min.
8. the preparation method of currant Phellinus polysaccharide according to claim 3, it is characterized in that, in step (4), the condition of described DEAE-cellulose chromatography is: stepwise elution, elutriant is followed successively by distilled water, 0.05mol/L NaCl solution, 0.1mol/L NaCl solution and 0.2mol/L NaCl solution, and flow velocity is 2ml/min.
9. the preparation method of currant Phellinus polysaccharide according to claim 3, it is characterized in that, in step (4), described gel is Superdex 30, gel permeation chromatography condition is: elutriant is 0.05mol/L NaCl solution, and flow velocity is 0.5ml/min.
10. the application of currant Phellinus polysaccharide according to claim 1 in the medicine of preparation treatment nerve degenerative diseases.
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| CN116731220A (en) * | 2023-06-19 | 2023-09-12 | 临沂大学 | Preparation method of black currant phyllosphere polysaccharide |
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| CN107474149A (en) * | 2017-08-03 | 2017-12-15 | 西华师范大学 | A kind of new natural products cockscomb granulose LSM X and its application |
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| CN116731220B (en) * | 2023-06-19 | 2024-01-23 | 临沂大学 | Preparation method of black currant phyllosphere polysaccharide |
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