CN107090050B - Screwtree root polysaccharide and preparation method thereof and preparing the purposes in anticomplement medicament - Google Patents
Screwtree root polysaccharide and preparation method thereof and preparing the purposes in anticomplement medicament Download PDFInfo
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- CN107090050B CN107090050B CN201610088575.2A CN201610088575A CN107090050B CN 107090050 B CN107090050 B CN 107090050B CN 201610088575 A CN201610088575 A CN 201610088575A CN 107090050 B CN107090050 B CN 107090050B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
Abstract
The invention belongs to the field of Chinese medicines, and in particular to natural homogeneous polysaccharide and preparation method thereof and the purposes in pharmacy in screwtree root；The present invention is separated from heat-clearing and detoxifying herb screwtree root is made homogeneous polysaccharide HA-PS1 and HA-PS2, it is tested through external anti-complement activity, as a result it confirms, the screwtree root homogeneous polysaccharide HA-PS1 and HA-PS2 has significant inhibiting effect, CH to the classical pathway and alternative pathway of complement activation50Value is respectively 0.147 mg/ml and 0.155 mg/ml, AP50Value is respectively 0.059 mg/ml and 0.132 mg/ml, can be further used as active constituent, prepare anticomplement medicament.
Description
Technical field
The invention belongs to the field of Chinese medicines, are related to polysaccharide, and in particular in screwtree root natural homogeneous polysaccharide and preparation method thereof and
Purposes in pharmacy；Two natural homogeneous polysaccharides and preparation method thereof and in preparing anticomplement medicament especially in screwtree root
Purposes.
Background technique
Prior art discloses the excessive activation of complement system can cause systemic loupus erythematosus, rheumatoid arthritis,
A variety of major diseases such as acute respiratory distress syndrome, however still lack ideal therapeutic agent to such disease at present,
Therefore clinically it is badly in need of efficient, low toxicity, single-minded novel complement inhibitor.Complement inhibitor is researched and developed from natural products is
An important research field by more and more concerns in recent years, has the characteristics that at low cost, small toxicity.Domestic and foreign scholars
Isolated a variety of singulations with complement system inhibiting effect from a variety of natural products including marine organisms
Object is closed, provides wide prospect for the research and development of anticomplement medicament.
It is widely present the active constituent with anticomplementary action in natural drug, part natural drug is completed both at home and abroad such as
The screening of Chinese ephedra, Morinda officinalis, ginseng, Cortex Eucommiae etc. finds certain polysaccharide, protein, polypeptide, the Huang being widely present in nature
The compounds such as ketone, steroid, terpene and alkaloid have significant anti-complement activity, from ginseng, turmeric, Chinese herbaceous peony, radix bupleuri, Rhizoma Chuanxiong
A series of acidic polysaccharoses and neutral polysaccharide for having anti-complement activity are separated in the plants such as Radix Glycyrrhizae.
Screwtree root be Sterculiaceae plant screwtree root (Helicteres angustifoliaL. dry root or complete stool), taste
It is bitter, cold in nature, return lung, large intestine channel, can inducing diaphoresis heat-clearing, removing toxicity for detumescence, for treat cold, fever, mumps, newborn pretty young woman, morbilli, cough,
Dysentery, carbuncle swells.Modern pharmacological studies have shown that screwtree root has antibacterial, anti-inflammatory, antiviral and antitumor isoreactivity.There is research
It was found that screwtree root also has stronger external anti-complement activity, wherein Thick many candies anti-complement activity is significant, has not yet to see to it
The separation preparation of middle anti-complement activity homogeneous polysaccharide and active report.
Summary of the invention
The object of the present invention is to provide the active constituents in natural drug with anticomplementary action, and in particular in screwtree root
Natural homogeneous polysaccharide and preparation method thereof and the purposes in pharmacy.
Natural homogeneous polysaccharide of the present invention is screwtree root polysaccharide HA-PS1 and HA-PS2.
The present invention carries out isolated two homogeneous polysaccharides to the water extract of heat-clearing and detoxifying herb screwtree root, is respectively designated as
HA-PS1 and HA-PS2；It is confirmed through experiment in vitro, screwtree root the homogeneous polysaccharide HA-PS1 and HA-PS2 all have significantly
Complement inhibitory activity can further prepare anticomplement medicament.
In the present invention, the Chinese medicine screwtree root is Sterculiaceae screwtree root platymiscium screwtree rootHelicteres angustifolia L. aerial part.
The structure feature of screwtree root polysaccharide HA-PS1 and HA-PS2 of the present invention are respectively as following:
HA-PS1 is dark-brown loose powder, and molecular weight is about 2 × 105 Da, total sugar content 97.06%, protein content:
1.34%；Glucuronic acid content: 1.09%；Sulfate content: 0.58%.Complete sour water solution obtains 3 kinds of monosaccharide compositions, and saccharide residue rubs
That ratio are as follows: D- galactolipin (Gal): D-Glucose (Glc): D-MANNOSE (Man)=1:0.3:0.1.Methylation analysis combines
Acid results of hydrolysis shows that its main connection type includes end, 1,3- and 1, the galactolipin of 6- connection, the Portugal of 1,6- connection completely
Grape sugar and the mannose of 1,3,6- connection；
HA-PS2 is dark-brown loose powder, and molecular weight is about 2 × 105 Da, total sugar content 96.54%, protein content:
1.66%；Glucuronic acid content: 2.29%；Sulfate content: 1.02%.Its monosaccharide composition analysis and methylation analysis results show
HA-PS2 monosaccharide composition and connection type and HA-PS1 are almost the same, in conjunction with13C-NMR analysis, finds two unique areas of heteroglycan
Do not contain in HA-PS1βD-Glucose, and HA-PS2 containsαD-Glucose.
Screwtree root polysaccharide HA-PS1 and HA-PS2 of the present invention is prepared by following methods:
Chinese medicine screwtree root is extracted with 95% alcohol reflux, and filtration, the dregs of a decoction are volatilized to no alcohol taste, extracted with hot water, is filtered,
95% ethyl alcohol of 4 times of volumes is added in concentration, centrifugation, supernatant, stands, and supernatant is removed in centrifugation, and precipitating is volatilized to no alcohol taste, then with water
It redissolves, trichloroacetic acid is added to remove floating preteins, centrifugation, supernatant is adjusted to neutrality, is concentrated, and dialysis is freeze-dried up to Thick many candies；
Thick many candies add distilled water to dissolve, and centrifugation, supernatant uses DEAE-cellulose column (Cl by several times-1 Type) chromatography progress initial gross separation,
It is eluted with the NaCl solution of the mol/L of distilled water, 0.4,0.8,1.2 and 2.0, collects and merge 0.8,1.2 and 2.0 mol/L's
NaCl solution elutes fraction, is concentrated, and dialyses, and freeze-drying, appropriate distilled water, which is added, to be made to dissolve, and centrifugation, supernatant is used
Sephacryl S-300 column chromatography is isolated and purified repeatedly using distilled water as eluent, each flow point is collected, according to HPLC
Testing result merges identical retention time flow point, is concentrated, is freeze-dried respectively, and carry out anti-complement activity test, mountain sesame is made
Numb homogeneous polysaccharide HA-PS1 and HA-PS2；
The present invention has carried out in vitro test, the results show that the screwtree root polysaccharide HA-PS1 and HA-PS2 passes through complement
Allusion quotation and alternative pathway activate caused cell haemolysis to have apparent inhibiting effect, show there is apparent anticomplementary action；
CH50Value (classical pathway 50% inhibit haemolysis needed for test sample concentration) be respectively 0.147 ± 0.014 mg/ml and 0.155 ±
0.014 mg/ml; AP50Value (concentration of test sample needed for alternative pathway 50% inhibits haemolysis) is respectively 0.059 ± 0.012 mg/
Ml and 0.132 ± 0.024 mg/ml.
Screwtree root homogeneous polysaccharide HA-PS1 and HA-PS2 of the invention can further prepare anticomplement medicament.
Detailed description of the invention
Fig. 1 is the HPGPC chromatogram of screwtree root polysaccharide HA-PS1 (A) and HA-PS2 (B), wherein TSK-GEL GMPWXL
300 × 7.6mm of gel column；Eluent: deionized water；Flow velocity: 0.8 ml/min.
Specific embodiment
Embodiment 1 prepares screwtree root polysaccharide HA-PS1 and HA-PS2
15 Kg of screwtree root dry aerial parts is taken to crush, with 95% alcohol reflux extraction 3 times, 2 h, filtration add 10 every time
The water heating of amount decocts 3 times again, and 2 hours every time, combined extract was concentrated into small size, quiet with 4 times of volume dehydrated alcohols
It sets, supernatant is removed in centrifugation, and precipitating is volatilized to no alcohol taste, after the dissolution of a small amount of water, adds appropriate trichloroacetic acid (final concentration of
10%) 2 h, are stood under 4 oC.Solution goes to precipitate through centrifugation, and supernatant adjusts pH value to 7 with 10% NaOH, dialyses to flowing water
48 h are freeze-dried to obtain Thick many candies.85 g of Thick many candies is weighed, appropriate distilled water dissolution, centrifugation, supernatant DEAE- is added
Cellulose column (Cl-Type, 120 × 12 cm) chromatography progress initial gross separation；With distilled water, 0.4 M, 0.8 M, 1.2 M and
The NaCl solution of 2.0 M elutes, and the elution volume of every kind of concentration gradient eluent is slightly larger than 2 times of column volumes, collects respectively each dense
Gradient flow point is spent, concentrated, tap water dialysis, distilled water dialysis and freeze-drying obtain 5 secondary components: HA-F1 ~ F5, and
5 fractions are carried out classical by way of anti-complement activity measurement；
The significant flow point HA-F3 ~ F5 of anti-complement activity is merged, taking 200 mg that appropriate distilled water is added makes to dissolve, it is centrifuged,
Supernatant is chromatographed with Sephacryl S-300 column (100 × 2.5 cm) and is isolated and purified repeatedly, using distilled water as elution
Liquid, is 0.8 ml/min with constant flow pump coutroi velocity, and 10 min/ pipe collects each flow point.Pipe HPLC tracing detection, and
Merge identical retention time fraction according to testing result, concentration and freeze-drying obtain 2 components, to 2 components respectively into
Component HA-PS1(870 mg is made in row enrichment, multiple gel filtration chromatography) and HA-PS2(540 mg)；
HA-PS1 and HA-PS2 obtained is detected through High Performance Gel Permeation Chromatography (HPGPC), the results showed that, it is uniform
Ingredient (as shown in Figure 1).
The structural characterization of 2 screwtree root polysaccharide of embodiment (HA-PS1 and HA-PS2)
(1) measurement of molecular weight
Using TSK-GEL GMPWXL gel column (300 × 7.6 mm), mobile phase is deionized water, 0.8 ml/ of flow velocity
Min, 25 DEG C of column temperature, by standard curve (Dextran of T series) calculate HA-PS1 and HA-PS2 molecular weight is respectively 217876
Da and 239527 Da；
(2) elemental analysis result
HA-PS1:C, 36.40%; H, 5.05%; N, 1.77%；
HA-PS2:C, 35.37%; H, 4.91%; N, 1.77%；
(3) specific rotation
HA-PS1 specific rotation:=-141.2 (c 0.3, H2O)；
HA-PS2 specific rotation:= -153.4 (c 0.3, H2O)；
(4) total reducing sugar, uronic acid, albumen and sulfate assay
It is 97.06% that sulfuric acid-phynol method, which measures HA-PS1 total sugar content,；HA-PS2 total sugar content is 96.54%；
The glucuronic acid content that meta-hydroxydiphenyl method measures HA-PS1 is 1.09%；The glucuronic acid content of HA-PS2 is 2.29%；
The protein content that Coomassie Brilliant Blue measures HA-PS1 is 1.34%；The protein content of HA-PS2 is 1.66%；
BaCl2The sulfate content of turbidimetry for Determination HA-PS1 is 0.58%；The sulfate content of HA-PS2 is 1.02%；
(5) sugared composition analysis
HA-PS1 and HA-PS2 is through 2 M TFA in 110 °C of all-hydrolytics, NaBH4Reduction, aceticanhydride acetylation are prepared into Alday
Alcohol acetic ester derivative, water/chloroform (1:l, v/v) extraction, concentration carry out GC-MS analysis (Blakeney AB, Harris
PJ, Henry RJ, et al. A simple and rapid preparation of alditol acetates for
Monosaccharide analysis. Carbohydr Res. 1983,113:291-299), the results show that the HA-
PS1 and HA-PS2 is made of 3 kinds of D- galactolipin (Gal), D-Glucose (Glc) and D-MANNOSE (Man) monosaccharide, and sugar is residual
Base molar ratio is galactolipin (Gal): glucose (Glc): mannose (Man)=1:0.3:0.1；
(6) methylation analysis
Reference literature method (methylation analysis methods [J] the foreign medical science (pharmacy fascicle) of Fang Jinian polysaccharide,
1986, (4): 222-226) methylate respectively to HA-PS1 and HA-PS2,90% formic acid solution of the product after methylation
It is poly-, 2 mol/L TFA all-hydrolytics, NaBH4The Alday alcohol acetic ester that partial methylation is made in reduction and aceticanhydride acetylation is derivative
Then object carries out GC-MS analysis；
Combined standard map judgement, the results showed that, in the methylate of the HA-PS1 and HA-PS2 galactolipin Ah
You have 2,3,4,6-Me by enlightening alcohol acetate derivative4-Galp, 2,3,4-Me3-GalpAnd 2,4,6-Me3-Galp；Glucose Ah
You have 2,3,4-Me by enlightening alcohol acetate derivative3-Glcp；The derivative of mannose residue only has 2,4-Me2-Manp, i.e. connection side
Formula is respectively end, 1,3 and 1,6 connection galactolipins, 1,6 connection glucose and 1,3,6 connection mannoses, the results showed that, it is described
HA-PS1 and HA-PS2 be heteroglycan there are branched structure, on mannose, the difference of the two only only has for branch
The ratio of Alday alcohol acetate derivative is different.
The test of 3 classical pathway Complement inhibition of embodiment
0.04 ml of complement (guinea pig serum) is taken, the solution that barbitol buffer solution (BBS) is configured to 1:10 is added, uses BBS
Two-fold dilution takes 1:1000 hemolysin, 2% sheep at the solution of 1:20,1:40,1:80,1:160,1:320,1:640 and 1:1280
Each 0.1 ml of red blood cell (SRBC) and each 0.2 ml of concentration complement are dissolved in 0.2 ml BBS, are mixed, after 37 oC water-bath, 30 min
It is put into low-temperature and high-speed centrifuge, is centrifuged 5 min under the conditions of 4000 rpm, 4 oC.Take every 0.2 ml of pipe supernatant in 96 holes respectively
Plate measures its absorbance in 405 nm；Experiment while full haemolysis group is set (0.1 ml, 2% SRBC, 0.1 ml hemolysin are dissolved in
0.4 ml tri-distilled water), using the absorbance of tri-distilled water haemolysis pipe as full haemolysis standard, hemolysis rate is calculated, is X with complement dilution
Axis, percentage of hemolysis be Y-axis mapping, select the minimum complement concentration for reaching similar high hemolysis rate as ensure system energy normally it is molten
Critical complement concentration needed for blood, take critical concentration complement and various concentration test solution mix, according to the above method in
Absorbance is measured under 405 nm；It tests while test sample control group, complement group and full haemolysis group is set；By test sample absorbance value
Hemolysis rate is calculated after deducting corresponding test sample control group absorbance value, using test sample concentration as X-axis, haemolysis inhibiting rate is as Y
Axis mapping, the concentration (CH of test sample needed for calculating 50% inhibition haemolysis50), the results are shown in Table 1.
The test of 4 alternative pathway Complement inhibition of embodiment
0.2 ml of complement (human serum) is taken, AP dilution is added, and (barbitol buffer solution, pH=7.4 contain 5 mM Mg2+, 8
MM EGTA) it is configured to the solution of 1:5, and two-fold dilution is at 1:10,1:20,1:40,1:80,1:160,1:320 and 1:640
Solution takes each 0.15 ml, AP dilution of concentration complement, 0.15 ml and 0.5% rabbit erythrocyte (RE), 0.20 ml, mixes, 37 oC
30 min of water-bath is placed on low-temperature and high-speed centrifuge, is centrifuged 5 min under the conditions of 4000 rpm, 4 oC.Every pipe supernatant is taken respectively
0.2 ml measures absorbance in 96 orifice plates, in 405 nm；Experiment while full haemolysis group is set (0.20 ml, 0.5% RE is dissolved in 0.3
Ml tri-distilled water), using the absorbance of tri-distilled water haemolysis pipe as full haemolysis standard, hemolysis rate is calculated, using complement dilution as X-axis,
Percentage of hemolysis is Y-axis mapping, select the minimum complement concentration for reaching similar high hemolysis rate as ensuring the normal haemolysis of system energy
The test solution of required critical complement concentration, the complement and various concentration that take determining critical concentration mixes, by above-mentioned side
Method measures its absorbance under 405 nm；It tests while test sample control group, complement group and full haemolysis group is set, test sample is inhaled
Shading value calculates hemolysis rate after deducting corresponding test sample control group absorbance value, using test sample concentration as X-axis, haemolysis inhibiting rate
It maps as Y-axis, the concentration (AP of test sample needed for calculating 50% inhibition haemolysis50).The results are shown in Table 1.
Table 1 is inhibiting effect of two kinds of screwtree root polysaccharide to complement activation.
Table 1
Wherein: CH50And AP50Value expression are as follows: average value ± SD(n=3).
Claims (4)
1. screwtree root polysaccharide, which is characterized in that the screwtree root polysaccharide is natural homogeneous polysaccharide comprising screwtree root polysaccharide
HA-PS1 and HA-PS2, structure feature are respectively as follows:
Screwtree root polysaccharide HA-PS1: the heteroglycan being mainly made of three kinds of monosaccharide, saccharide residue molar ratio are D- galactolipin: D- grape
Sugar: D-MANNOSE=1:0.3:0.1；Molecular weight is 217876 Da；Specific rotation [α] in waterD 25It is -141.2 °；Protein content:
1.34%；Glucuronic acid content: 1.09%；Sugared content 97.06%；Sulfate content: 0.58%；
Screwtree root polysaccharide HA-PS2: the heteroglycan being mainly made of three kinds of monosaccharide, saccharide residue molar ratio are D- galactolipin: D- grape
Sugar: D-MANNOSE=1:0.3:0.1；Molecular weight is 239527 Da；Specific rotation [α] in waterD 25It is -153.4 °；Protein content:
1.66%；Glucuronic acid content: 2.29%；Sugared content 96.54%；Sulfate content: 1.02%.
2. screwtree root polysaccharide according to claim 1, characterized in that prepared by following steps:
Screwtree root medicinal material is volatilized, is extracted with hot water with 95% alcohol reflux grease removal, the dregs of a decoction, is filtered, and is concentrated, and centrifugation, supernatant adds
Enter 95% ethyl alcohol of 4 times of volumes, stand, supernatant is removed in centrifugation, and precipitating volatilizes, then is redissolved with water, and trichloroacetic acid is added to remove free egg
White, centrifugation, supernatant is adjusted to neutrality, is concentrated, and dialysis is freeze-dried up to Thick many candies；Thick many candies add distilled water to dissolve, centrifugation,
Supernatant carries out initial gross separation with DEAE-cellulose column chromatography by several times, with the mol/L of distilled water, 0.4,0.8,1.2 and 2.0
NaCl solution elution, collect and merge the NaCl solution of 0.8,1.2 and 2.0 mol/L and elute fraction, be concentrated, dialysis, freezing is dry
It is dry；Add distilled water to make to dissolve, be centrifuged, supernatant Sephacryl S-300 column chromatography is divided using distilled water as eluent
From purifying；Each flow point is collected, identical retention time flow point is merged according to HPLC testing result, is concentrated, is freeze-dried respectively, go forward side by side
The test of row anti-complement activity, is made anti-complement activity homogeneous polysaccharide HA-PS1 and HA-PS2.
3. screwtree root polysaccharide described in claim 1 is preparing the purposes in anticomplement medicament.
4. purposes according to claim 3, which is characterized in that screwtree root polysaccharide described in the screwtree root polysaccharide inhibits to mend
Body classics and alternative pathway activate caused cell haemolysis.
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