CN104292351B - A kind of Fructus Camelliae sinensis Phellinus polysaccharide and its preparation method and application - Google Patents
A kind of Fructus Camelliae sinensis Phellinus polysaccharide and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of Fructus Camelliae sinensis Phellinus polysaccharide and its preparation method and application, belong to polysaccharide field.Fructus Camelliae sinensis Phellinus polysaccharide prepared by the present invention, novel structure, is isolated first；Its structure contains repeatably cellular construction, this repeatable cellular construction is constituted main chain by 3 (1 → 3) β D glucoses, having a branch 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.The invention also discloses the preparation method of a kind of Fructus Camelliae sinensis Phellinus polysaccharide, the method is simple, applicable, and the purity of polysaccharide of extraction is up to more than 93%, and the polysaccharide of preparation can be used for the medicine of the neurodegenerative diseases such as preparation treatment Alzheimer.
Description
Technical field
The present invention relates to polysaccharide field, be specifically related to a kind of Fructus Camelliae sinensis Phellinus polysaccharide and its preparation method and application.
Background technology
Alzheimer, is a kind of ofneurodegenerative with progressive dementia as principal character occurred in the geratic period
Disease.Along with world population aging increasingly, onset of Alzheimer disease rate is more and more higher, it has also become the cardiovascular disease that continues, cancer
The fourth-largest killer after disease and apoplexy, the healthy of old people and quality of life in serious harm.Be currently used for treat Ah
The medicine of Alzheimer's disease probably has more than 10 to plant, mainly cholinomimetic thing and improve the nootropics of brain metabolism, wherein acetyl gallbladder
Alkali enzyme inhibitor (cholinomimetic) is the first-line drug treating Alzheimer at present, such as tacrine (Tacrine), the most how to send
(Donepezil), profit this bright (Rivastigmine), galantamine (Galanthamine) and huperzine are first-class together.Clinical
These medicines of upper application can only alleviate the cognitive disorder of patient in early days, it is provided that the symptom improvement result of appropriateness, it is impossible to stops disease
The progress of feelings.Up to the present, still lack etiological treatment and control the active drug of disease process.
Nerve growth factor (nerve growth factor, NGF), as most important in neurotrophic factor family
Member, to degenerate dopaminergic neuron cell and promote striatal dopamine neuron cell regeneration have potential
Protective effect, be expected to cure Alzheimer.But, as protein matter, there is unstable chemcial property, body in NGF
The shortcomings such as the interior half-life is short, pharmacokinetic properties is not good enough, and not easily pass through blood brain barrier, and expensive, limit it
Clinical application.Therefore, the controlling for Alzheimer of other compounds with neurotrophic " NGF " sample is actively found
Treatment has great importance.
Fructus Camelliae sinensis Phellinus polysaccharide is to separate to obtain from medicinal fungi Fructus Camelliae sinensis Phellinus (Phellinus ribis)
The homogeneous polysaccharide component with neurotrophic activity obtained, research shows that it can show in the range of 10 g/ml-150 g/ml
Write the growth of the PC12 neurite promoting NGF mediation, it is expected to develop into the neurodegenerative diseases treatments such as Alzheimer
Drug candidate.Research not relevant report before the present invention completes about Fructus Camelliae sinensis Phellinus polysaccharide neurotrophic effect
Road.
Summary of the invention
It is an object of the invention to provide a kind of Fructus Camelliae sinensis Phellinus polysaccharide with medical value and preparation method thereof
And application.The Fructus Camelliae sinensis Phellinus polysaccharide of the present invention, novel structure, is isolated, named PRG first；Its preparation side
Method is simple, applicable, and the purity of polysaccharide of extraction is up to more than 93%.This product can be used for the nerves such as preparation treatment Alzheimer
The medicine of degenerative disease.
The present invention is by the following technical solutions:
A kind of Fructus Camelliae sinensis Phellinus polysaccharide, it is characterised in that its monosaccharide consists of β-D-Glucose, and having in its structure can
Repeat unit structure；Described repeatable cellular construction is constituted main chain by 3 (1 → 3)-β-D-Glucoses, at wherein the one of main chain
There is a branch C6 position of individual (1 → 3)-β-D-Glucose, and branch is in series by 3 (1 → 6)-β-D-Glucoses, and it repeats
Unit structure type is as follows:
。
Terminal glucose, (1 → 3)-β-D-Glucose, (1 → 6)-β-D-Portugal in described Fructus Camelliae sinensis Phellinus polysaccharide
The component molar of grape sugar and (1 → 3,6)-β-D-Glucose is than about 1:2:2:1；
Described Fructus Camelliae sinensis Phellinus polysaccharide, weight average molecular weight is 5.16 × 103Da ,+32.1 ° of (c of specific rotatory power
0.1, H2O)。
The preparation method of a kind of Fructus Camelliae sinensis Phellinus polysaccharide, it is characterised in that it comprises the following steps:
(1) water carries: take Fructus Camelliae sinensis Phellinus sporophore coarse powder, adds the distilled water of 20 times of-40 times of weight, 90 DEG C-100 DEG C
Extract 4 times, each 4h-6h, filter, merging filtrate, concentrate, add ethanol to alcohol content 80%, stand 24h, centrifugal, obtain Fructus Camelliae sinensis
Phellinus total polysaccharides crude product；
(2) Deproteinization: the total polysaccharides crude product of step (1) gained is dissolved in distilled water, with protease hydrolyzed, inactivation and from
The heart removes Denatured protein enzyme, and centrifugal gained supernatant adds organic solvent, vibration, is centrifuged, and removes lower floor's organic facies and middle egg
White, repeating the step of organic solvent process until producing without white precipitate, obtaining the polysaccharide Aqueous extracts after Deproteinization；
(3) step ethanol precipitation: concentrated by the Aqueous extracts in step (2), adds ethanol to alcohol content 50%, centrifugal, discards precipitation
Thing, supernatant continues to add ethanol to alcohol content 80%, stands, centrifugal, and precipitate is successively with dehydrated alcohol, washing with acetone, and vacuum is done
Dry, obtain Fructus Camelliae sinensis Phellinus classification polysaccharide crude；
(4) column chromatography: through DEAE-fiber after the Fructus Camelliae sinensis Phellinus classification polysaccharide crude dissolving that step (3) is obtained
Element column chromatography, phend-sulphuric acid detection polysaccharide, collect it after the eluent of the second eluting peak again through gel filtration chromatography, phenol-
Sulfuric acid process detection polysaccharide, collects the eluent of main peak, and eluent is concentrated, obtain the Fructus Camelliae sinensis wood of the present invention after dialysis and lyophilizing
Shelf fungus polysaccharide.
In above-mentioned steps (1), described centrifugal speed is 3000rpm-4000rpm, and the time is 15min-30min；
In above-mentioned steps (1), adding the distilled water of 30 times of weight of Fructus Camelliae sinensis Phellinus, Extracting temperature is 95 DEG C, extracts
Time is each 6h, and centrifugal speed is 3000rpm, and centrifugation time is 20min.
In above-mentioned steps (2), described protease is trypsin；Described organic solvent is chloroform and n-butyl alcohol, described chlorine
Imitative and n-butyl alcohol volume ratio 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, eluent is followed successively by distillation
Water, 0.05mol/L NaCl solution, 0.1mol/L NaCl solution and 0.2mol/L NaCl solution, flow velocity is 2ml/min.
In above-mentioned steps (4), described gel is Superdex 30, and gel permeation chromatography condition is: eluent is
0.05mol/L NaCl solution, flow velocity is 0.5ml/min.
Described Fructus Camelliae sinensis Phellinus polysaccharide can apply in the medicine for the treatment of neurodegenerative diseases.
Present invention have the advantage that
Fructus Camelliae sinensis Phellinus polysaccharide (PRG) of the present invention, is to separate first to obtain from Fructus Camelliae sinensis Phellinus, is one new
The glucosan of novel structure.PRG by terminal glucose, 1 → 3 connect glucose, 1 → 6 connect glucose and 1 → 3,6
The glucose composition connected, component molar ratio is for 1:2:2:1.IR proves that PRG is saccharide, for beta configuration.This polysaccharide Weight-average molecular
Amount 5.16 × 103Da, specific rotatory power+32.1 ° (c 0.1, H2O)。
PRG can promote the growth of the PC12 neurite that NGF mediates, and has stronger neurotrophic activity, for grinding first
Study carefully discovery, can be used for preparing the medicine of neurodegenerative diseases treatment.This active polysaccharide has no report before making the present invention.
Accompanying drawing explanation
Fig. 1 is the HPSEC-MALLS chromatogram of PRG.
Fig. 2 is that PRG is at 200nm-400nm UV scanning collection of illustrative plates.
Fig. 3 is the derivative rear gas chromatogram of standard monosaccharide sugar nitrile acetas.
Fig. 4 is the gas chromatogram after PRG hydrolyzate sugar nitrile acetas derives.
Fig. 5 is the infrared spectrum of PRG.
Fig. 6 is the nmr spectrum (a) of PRG1H 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.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described further.
Embodiment 1
The preparation of Fructus Camelliae sinensis Phellinus polysaccharide, it comprises the following steps:
(1) water extraction: Fructus Camelliae sinensis Phellinus fruit body powder is broken into coarse powder, adds 30 times amount distilled water (g/ml), mixed
After closing uniformly in thermostat water bath 95 DEG C extract 4 times, each 6h, gauze filters, and merges Aqueous extracts, concentrates, adds 4 times of water and carry
The dehydrated alcohol that liquid is long-pending, stands 24h, 3000rpm and is centrifuged 20min, obtain Fructus Camelliae sinensis Phellinus total polysaccharides crude product.
(2) Deproteinization: the Fructus Camelliae sinensis Phellinus total polysaccharides crude product of step (1) gained is dissolved in distilled water, obtains tea
Sub-Phellinus crude polysaccharides aqueous solution, adds the protease of crude polysaccharides weight 1%, 45 ° of C water-bath 8 h, then heats to 90 °
C maintains 10 min inactivators, is cooled to room temperature, and 5000rpm is centrifuged 30min and removes Denatured protein and enzyme, at centrifugal gained supernatant
Liquid add 1/4th supernatant volume Sevag reagent (chloroform and n-butyl alcohol, wherein the volume ratio of chloroform and n-butyl alcohol is 5:
1), acutely vibrate 15min, is centrifuged off lower floor's organic facies and middle protein layer, repeats by Sevag agent treated step until nothing
White precipitate produces, and obtains the polysaccharide Aqueous extracts after Deproteinization.
(3) step ethanol precipitation: Aqueous extracts step (2) obtained concentrates, adds the dehydrated alcohol of 1 times of volume to alcohol content
50%, stirring and evenly mixing, static 24h, 3000rpm be centrifuged 20min, discard precipitate, and supernatant continues to add dehydrated alcohol to alcohol content
80%, stand 24h, 3000rpm and be centrifuged 20min, precipitate with dehydrated alcohol, washing with acetone, vacuum drying, obtains Fructus Camelliae sinensis successively
Phellinus classification polysaccharide crude.
(4) column chromatography: Fructus Camelliae sinensis Phellinus classification polysaccharide crude distilled water step (3) obtained dissolves and obtains
The aqueous solution of 20mg/ml；First with distilled water balance DEAE-cellulose ion-exchange chromatography post (4.5cm × 30cm), by tea
Sub-Phellinus classification polysaccharide crude aqueous solution is through DEAE-cellulose ion-exchange column chromatography, applied sample amount 5ml, flow velocity 2ml/
Min, eluent 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 eluent phend-sulphuric acid of collection detects polysaccharide, collects the eluent of the second eluting peak；
The eluent of the second eluting peak collected is further purified, layer through gel permeation chromatography (Superdex 30)
The specification of analysis post is 1.8cm × 80cm, applied sample amount 2ml, and eluent is 0.05mol/L NaCl solution, and flow velocity is 0.5ml/min,
Eluent phend-sulphuric acid collected by gel permeation chromatography detects polysaccharide, collects the eluent of the main peak containing polysaccharide, through dense
Contracting, aperture be 2000Da bag filter dialysis after lyophilizing obtain the cotton-shaped homogeneous Fructus Camelliae sinensis Phellinus polysaccharide of white loose, life
Entitled PRG.
Embodiment 2
PRG purity detecting and molecular weight determination
Fructus Camelliae sinensis Phellinus polysaccharide PRG embodiment 1 prepared, uses high performance liquid chromatography combination multi-angle laser to dissipate
Penetrate mensuration purity and molecular weight.Chromatographic column is G3000 PWXL and two tsk gel posts of G4000 PWXL are used in conjunction, and outfit is shown
Difference refractive power and multiple angle laser light scattering detector, flowing is 0.2M NaNO mutually3.Sample 0.2M NaNO3It is configured to 1mg/ml's
Concentration, 0.22 μm filter membrane filters, and sample introduction 200 μ l, flow velocity is 0.6 ml/min.Record chromatographic peak such as Fig. 1, is shown as symmetry
Simple spike, illustrates that PRG homogeneity is good, and recording its weight average molecular weight is 5.16 × 103Da。
Embodiment 3
PRG component detects
The Fructus Camelliae sinensis Phellinus polysaccharide PRG that embodiment 1 is prepared, with phend-sulphuric acid detection total sugar content be
98.1%, with Coomassie Brilliant Blue (Bradford method) detection without albumen, between using, the detection of hydroxyl phynol method is without alduronic acid.1mg/
Ml aqueous solution carries out 200nm-400nm UV scanning, and result is shown in Fig. 2, at 260nm and 280nm, does not has obvious absorption peaks, says
Without nucleic acid and albumen in this sample bright.
Embodiment 4
PRG monosaccharide forms
Weigh Fructus Camelliae sinensis Phellinus polysaccharide PRG 10 mg that embodiment 1 prepares, add the trifluoroacetic acid of 2 mol/L
6ml, fills N2Rear sealing, 110 ° of C hydrolyze 3 hours, produce, and 60 ° of C are evaporated to do.Add methanol a little, be evaporated, repeat 3 ~ 5
Secondary, to steam TFA completely.Hydrolyzate vacuum drying 12h, adds the oxammonium hydrochloride. of 5mg, 0.3ml pyridine and 4mg inositol (interior
Mark), 90 ° of C stirring reaction 30min.It is cooled to room temperature after taking-up, adds the acetic anhydride of 0.8ml, continue reaction 30min under 90 ° of C and enter
Row acetylation, product directly carries out gas chromatographic analysis.Another label taking quasi-monosaccharide xylose, mannose, glucose and galactose
Prepare derivant by upper method, carry out gas chromatographic analysis.
Gas phase analysis chromatographiccondition is injection port: split-splitless, 250 ° of C of temperature；Chromatographic column: DB-5 stone
English capillary column, 0.25m × 0.25mm × 30m, flow 1mL/min；Heating schedule: 120 ° of C keep 3min, to 250 ° of C every point
Clock 8 ° of C of intensification, 250 ° of C keep 10min；Mass spectrum: EI source, ionization voltage 70eV；Detector: fid detector, 220 ° of C of temperature, carry
Gas He；Sample size: 0.5l, split ratio 30:1, sweep limits 20 ~ 600aum.
Result such as Fig. 3 and Fig. 4, by compareing with standard monosaccharide, PRG monosaccharide consists of glucose, and Fructus Camelliae sinensis timber layer is described
Obliqua polysaccharide PRG is glucosan.
Embodiment 5
PRG infrared spectrum detects
Take dry PRG1.0mg, with KBr tabletting, at 4000 cm-1-400cm-1In the range of carry out infrared spectrum and sweep
Retouch, record infrared spectrogram.
Such as Fig. 5, at 1730cm-1Left and right does not has the characteristic absorption peak of alduronic acid, at 810cm-1And 870cm-1Locate the sweetest
The characteristic absorption peak of dew sugar, shows without alduronic acid and mannose.1200~1000cm-1Locate the monosaccharide of strong absworption peak prompting PRG
For pyranoid ring type.At 3396.31cm-1There is a stronger broad peak in place, for the stretching vibration of hydroxyl (-OH)；?
2892.41cm-1The absworption peak that place occurs is more weak, for the stretching vibration of C-H.1612.98cm-1The absworption peak at place is due to sample
In water cause；At 896.72cm-1Place it is observed that absworption peak show that the glycosidic bond in PRG is beta configuration.
Embodiment 6
PRG magnetic resonance detection
Taking PRG30mg, 50 ° of C are vacuum dried 24h, are dissolved in 0.5ml D2In O, at Bruker Avance 600 MHz
Spectrometer is upper measures it1H NMR and13C H NMR spectroscopy, (the δ with DSS as internal standardH0.00ppm, δC21.74ppm), measure
Temperature is 40 ° of C.
1H NMR such as Fig. 6 (a).Four peaks are had, respectively at δ 4.39, δ 4.40, δ 4.60 in the different head region of 4.5 ~ 5.5ppm
At δ 4.65, prompting may have the connected mode of four kinds of glycosidic bonds；Its chemical displacement value is respectively less than 4.9, and glucosides in PRG is described
The configuration of key is β type.H signal at 3.2 ~ 4.2ppm is H-2 ~ H-6 proton on sugar ring, and chemical displacement value is close, overlapping tight
Weight.
PRG's13C NMR is shown in Fig. 6 (b).At 160～180ppm, have no carbonyl carbon signals, show that this polysaccharide is without alditol
Acid and glycoprotein, δ < has no carbon signal, illustrates in PRG without methyl sugar at 20ppm.The low place of 95 ~ 100ppm occurs four
Signal peak, for anomeric carbon, its chemical shift is δ 102.44 respectively, δ 102.72, δ 102.81 and δ 102.88, with1In H H NMR spectroscopy
Four anomer hydrogen signal peaks corresponding, the connection really containing four kinds of glycosidic bonds is described to form in the basic repetitive of PRG
Mode, more than 102ppm, chemical displacement value proves that monosaccharide residue is configured as β type further.Four anomeric carbons and the letter of anomeric proton
Number peak is 1 → 6,1 → 3,1 → 3 respectively, 6 and the signal peak of terminal glucose.The chemical shift signal in 60 ~ 90ppm region is
C-2 ~ C-6 signal on sugar ring, the δ 83.90 of the most relatively low field, δ 84.54 signal are 1 → 3,1 → 3,6 glucose residues connected
In C-3, due to become glycosides and shift to low field, do not become the C-3 of glycosides to be positioned at 75 ~ 78ppm chemical shift；The δ 60.61 of high field, δ
62.44 is unsubstituted C-6, is terminal glucose saccharide residue and 1 → 3 glucose residue signal connected respectively, according to glycosidation position
Moving rule, the C-6 signal that instead of will move to low field, is positioned near 70.00ppm, and this signal can compose [Fig. 6 (c)] from DEPT
In recognized, wherein the inverted peaks (CH2) at 68.62ppm be i.e. 1 → 6 connect and 1 → 3,6 connect glucose residues in
C-6 signal.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 Fructus Camelliae sinensis Phellinus polysaccharide PRG that embodiment 1 prepares.
Use PC12 raji cell assay Raji neurite outgrowth facilitation.Take the logarithm the PC12 cell of trophophase, with containing 10% horse blood
The DMEM suspension cell of cleer and peaceful 5% hyclone, counting, with every hole 8 × 103Individual cell is inoculated in 24 well culture plates, every hole body
Long-pending 400 μ l, at 37 DEG C, 5%CO2After incubator cultivates 24 h, replace original training with the DMEM containing 2% horse serum and 1% hyclone
Supporting base, be subsequently adding 1 ng/ml NGF and the sample solution of variable concentrations, each concentration arranges 3 multiple holes.Continue to cultivate 4 days
After, 4% paraformaldehyde is fixed, methylene blue staining, basis of microscopic observation.
Morphological observations such as Fig. 7, in the presence of the NGF of 1ng/ml, PRG can promote the growth of neural axon.Enter
Row quantitative analysis, result is shown in Fig. 8, when 10 g/ml, 50 g/ml, 150 g/ml concentration, putting down of PC12 cellular neural aixs cylinder
All length is respectively 40.9 μm, 54.3 μm and 58.4 μm, compares with matched group (average length is 32.7 μm) that to have significance poor
Different.Illustrate that Fructus Camelliae sinensis Phellinus polysaccharide PRG has significant neurotrophic activity, can develop as treatment nervus retrogression disease
Sick drug candidate as sick in A Ermoci.
Claims (2)
1. a Fructus Camelliae sinensis Phellinus polysaccharide application in the medicine of preparation treatment neurodegenerative diseases, its feature exists
In, the monosaccharide of described Fructus Camelliae sinensis Phellinus polysaccharide consists of β-D-Glucose, has repeatable cellular construction in its structure；Institute
State repeatable cellular construction and constituted main chain by 3 (1 → 3)-β-D-Glucoses, in one of them (1 → 3)-β-D-Portugal of main chain
There is a branch C6 position of grape sugar, and branch is in series by 3 (1 → 6)-β-D-Glucoses, and its repeat unit structure formula is as follows:
。
Fructus Camelliae sinensis Phellinus polysaccharide the most according to claim 1 is in the medicine of preparation treatment neurodegenerative diseases
Application, it is characterised in that terminal glucose in described Fructus Camelliae sinensis Phellinus polysaccharide, (1 → 3)-β-D-Glucose, (1 → 6)-
The component molar of β-D-Glucose and (1 → 3,6)-β-D-Glucose is than about 1:2:2:1；Described Fructus Camelliae sinensis Phellinus
Polysaccharide, weight average molecular weight is 5.16 × 103Da, with water as solvent, concentration is that specific rotatory power when 0.1 is+32.1 °.
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