CN1332983C - Polysaccharide of rhizoma corydalis, preparation method and application - Google Patents
Polysaccharide of rhizoma corydalis, preparation method and application Download PDFInfo
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- CN1332983C CN1332983C CNB2004100890832A CN200410089083A CN1332983C CN 1332983 C CN1332983 C CN 1332983C CN B2004100890832 A CNB2004100890832 A CN B2004100890832A CN 200410089083 A CN200410089083 A CN 200410089083A CN 1332983 C CN1332983 C CN 1332983C
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Abstract
The present invention relates to a polysaccharide extracted from traditional Chinese medicines of rhizoma corydalis, a preparation method and the application thereof. The method comprises the following steps: soaking the rhizoma corydalis in water to obtain water extract of rhizoma corydalis, precipitating with organic solvents, dissolving sediment in water, carrying out dialysis or membrane separation on supernatant fluid, concentrating and drying to obtain a total polysaccharide, and carrying out column chromatography and purification on the total polysaccharide of rhizoma corydalis to obtain the polysaccharide YhPS of rhizoma corydalis. The value of n in the constitutional repeating unit is 1 to 20. The method has the advantages of simple manufacturing process and high yield, and is suitable for commercial process. The total polysaccharide YhPS-T of rhizoma corydalis has protective effects on cerebral ischemia, and can be used for preparing medicaments or health-care products with protective effects on cerebral ischemia, which is indicated in pharmacodynamics experiment.
Description
Technical field
The compound of polysaccharide that the present invention relates to extract from Chinese medicinal materials particularly relates to polysaccharide of rhizoma corydalis YhPS, its production method and the purposes extracted from the crude drug corydalis tuber.
Technical background
Corydalis tuber is a kind of traditional Chinese medicinal materials, for one of famous " Zhejiang eight flavors ", has the effect of " promoting blood circulation and removing blood stasis, regulating QI to relieve pain ".
Bibliographical information, [Zhu Dayuan etc., chemical journal, (39), 280 (1981)], [Fu Xiaoyong etc., Acta Pharmaceutica Sinica, 21 (6), 447 (1986)], [Fu Xiaoyong etc., pharmaceutical analysis magazine, 6 (2), 66 (1986)], its chemical ingredients mainly contains more than 20 kind of alkaloid, and other contains a spot of phlegmatic temperament, resin, volatile oil, neutral substance and inorganic elements etc., and the research of carbohydrate does not appear in the newspapers as yet in the relevant corydalis tuber.
Summary of the invention
The problem to be solved in the present invention provides a kind of polysaccharide of rhizoma corydalis and production method and purposes.
The invention provides a kind of polysaccharide that obtains that extracts from the crude drug corydalis tuber, its repeated structural unit is:
N=1～20 wherein, Glcp is a glucopyranose, its main chain is → 4)-α-Glcp (1 →, i.e. 1,4 glucose that connects, each repeating unit is made up of 12 monose, a side chain is arranged in the structure, be connected → 4,6)-α-Glcp (1 →, promptly 1,4, on 6 glucose that connect, have in the side chain → 6)-α-Glcp (1 → be 1,6 glucose and the α-Glcp (1 → non-reduced terminal glucose that connects.
The preparation method of polysaccharide of rhizoma corydalis of the present invention will be soaked in water through crude drug, adopts organic solvent deposit, dialysis or membrane sepn, and concentrate drying obtains total polysaccharides.The corydalis tuber total polysaccharides gets polysaccharide of rhizoma corydalis YhPS through ion exchange column and gel filtration chromatography purifying.
This polysaccharide is analyzed through acid hydrolysis fully, reduction, acetylize and GC, and the result shows that it mainly is made up of glucose, and other contains the semi-lactosi and the pectinose of trace.Recording its molecular weight ranges by the HPLC analysis is 1600～35000.Its NMR spectral data is as described below: δ (ppm):
1H-NMR:5.44 is → 4) α-Glcp (1 →, 5.40 for → 4,6) α-Glcp (1 →, 5.38 be → 6) α-Glcp (1 →, 5.01 be α-Glcp (1 →.
13C-NMR:101.955 is → 4) α-Glcp (1 →, 102.119 is → 6) α-Glcp (1 →, 102.274 is → 4,6) α-Glcp (1 →, 100.998 be α-Glcp (1 →.
From YhPS through methylate, the GC-MS atlas analysis of reduction, acetyl derivatives learns that YhPS contains fragment → 4) α-Glcp (1 →, → 6) α-Glcp (1 →, → 4,6) α-Glcp (1 → and α-Glcp (1 →, its mol ratio is 9: 1: 1: 1.According to methylate, analysis such as NMR, can infer that YhPS has following repeat unit structure:
N=1～20 wherein
Preparation method provided by the invention comprises after the crude drug corydalis tuber drying, is soaked in water, and adopts organic solvent deposit, dialysis or membrane sepn, and concentrate drying obtains the corydalis tuber total polysaccharides.The corydalis tuber total polysaccharides can get the pure product YhPS of polysaccharide of rhizoma corydalis through ion exchange column and gel filtration chromatography purifying.
Specifically, dried crude drug corydalis tuber is pulverized or section, be soaked in water, wherein the weight ratio recommendation of corydalis tuber and water logging bubble is a corydalis tuber: water=1: 10～15, especially recommend water with 10～12 times of weight, and soaked 24～36 hours.Described water is recommended as deionized water.The pH value of soak solution recommends to remain on 6.0～7.0.
Filter, filtrate through or without concentrating, with centrifugal behind the organic solvent deposit.Centrifugal gained precipitation water dissolution is recommended the water dissolution with 1～5 times of weight.
Centrifugal, supernatant liquor dialysis or membrane sepn, dialysis time is recommended as 24～72 hours, and dialysis recommends molecular weight cut-off below 1000 with dialysis membrane, dialysis tubing, its aperture, and especially recommending molecular weight cut-off is 500.
Concentrate drying obtains total polysaccharides, and wherein drying or concentrating under reduced pressure temperature are recommended to be lower than 60 ℃ and carried out, and preferably adopt cryogenic vacuum to concentrate or lyophilize, and for example 30～60 ℃ of dryings or concentrate, pressure recommends to be controlled at 0.08～0.1MPa.
Described corydalis tuber total polysaccharides is dissolved in water, and wherein recommends the water dissolution of 1～5 times of weight.Through the DEAE-Cellulose column chromatography, with collecting behind the deionized water wash-out, purity can reach 80～90% then.Be further purified through gel filtration chromatography, water or rare salts solution wash-out are collected sugared peak again, obtain the pure product YhPS of polysaccharide of rhizoma corydalis through SephadexG-10 desalination postlyophilization then, and purity can reach more than 97%.The gel that gel filtration chromatography adopted is Sephadex G type, Sephacryl S type, Superose type, Bio-Gel P type or Superdex, and the separating ranges of selecting for use is 1 * 10
3-5 * 10
4Dalton.Recommend gel SephadexG75, the deionized water wash-out.
The aforesaid organic solvent deposit of using, the organic solvent that described organic solvent is recommended and water dissolves each other can be the alcohol or the ketone of low carbon chain, for example C
1～C
6Alcohol or ketone etc.
Polysaccharide of rhizoma corydalis provided by the invention and total polysaccharides thereof can be used for preparing medicine or the healthcare products with cerebral ischemia provide protection.
The present invention extracts polysaccharide of rhizoma corydalis YhPS and total polysaccharides thereof first from corydalis tuber.Extraction and separation method of the present invention is easy, and productive rate is high and be suitable for suitability for industrialized production.
Description of drawings
Fig. 1 is the HPLC figure of polysaccharide of rhizoma corydalis YhPS.Analytical column is BIOSEP-S4000, elutriant: distilled water, and flow velocity: 1mL/min, detector: RI analyzes and obtains single symmetrical peak, main peak content 98.643%.
Fig. 2 is 1gMw and the Rt canonical plotting that the HPLC method is measured the standard dextran (Sigma) of polysaccharide molecular weight, and linear equation is: 1gMw=8.52526-0.33215Rt (r=-0.9993).As shown in Figure 1, the Rt of YhPS is 13.410min, calculates by linear equation to show that the molecular-weight average of YhPS is 11779, and molecular weight ranges is 2000～39000.
Fig. 3 is the GC figure that standard monose is analyzed.Analytical column OV-17 capillary column (0.32mm * 30m), 200 ℃ of temperature (2min)
1.5 ℃/min260 ℃.The peak of its each standard monose distributes as follows:
| Peak number | 1 | 2 | 3 | 4 | 5 | 6 |
| Rt(min) | 18.026 | 19.031 | 20.053 | 30.454 | 30.999 | 31.484 |
| Standard monose | Rha | Ara | Xyl | Man | Glc | Gal |
Annotate: Rha is a rhamnosyl; Ara is a pectinose; Xyl is a wood sugar; Man is a seminose; Glc is a glucose; Gal is a semi-lactosi.
Fig. 4 is the GC figure of polysaccharide of rhizoma corydalis YhPS.Analytical column OV-17 capillary column (0.32mm * 30m), 200 ℃ of temperature (2min)
1.5 ℃/min260 ℃.The monose of its polysaccharide of rhizoma corydalis YhPS is composed as follows:
| Peak number | 1 | 2 | 3 | 4 |
| Rt(min) | 12.061 | 18.934 | 31.072 | 31.369 |
| Monose is formed | Impurity peaks | Ara | Glc | Gal |
Annotate: Rha is a rhamnosyl; Ara is a pectinose; Glc is a glucose; Gal is a semi-lactosi.
Fig. 5 is the infrared spectrogram of polysaccharide of rhizoma corydalis YhPS.The principal character absorption peak is:
929cm-1 is the asymmetric stretching vibration absorption peak of D-grape pyrans cyclohexanol, 764cm-1 is the symmetrical stretching vibration absorption peak of D-grape pyrans cyclohexanol, 853cm-1 is the C-H angle vibration absorption peak of α-anomerism, and 1079cm-1,1024cm-1 are the characteristic absorbance of C-O key on the pyranoid ring.
Fig. 6 is polysaccharide of rhizoma corydalis YhPS
1H-nucleus magnetic resonance (NMR) collection of illustrative plates.
1H-NMR:5.44 is → 4)-α-Glcp (1 →, 5.40 for → 4,6)-α-Glcp (1 →, 5.38 be → 6)-α-Glcp (1 →, 5.01 be α-Glcp (1 →.
Fig. 7 is polysaccharide of rhizoma corydalis YhPS
13C-nucleus magnetic resonance (NMR) collection of illustrative plates.
13C-NMR:100.998 be α-Glcp (1 →, 101.955 is → 4)-α-Glcp (1 →, 102.119 is → 6)-α-Glcp (1 →, 102.274 is → 4,6)-α-Glcp (1 →.
Fig. 8 is the GC collection of illustrative plates in the GC-MS collection of illustrative plates of polysaccharide of rhizoma corydalis YhPS.It shows 6 fragment peaks, and peak 1 (15.905min), 2 (17.419min), 3 (19.761min) and 4 (23.296min) are sugared peak, and 5 (24.336min) and 6 (27.564min) are non-sugared peak.
Fig. 9 is the fragment mass spectrum of Rt=15.905min, illustrate contain α-Glcp (1 →.
Figure 10 is the fragment mass spectrum of Rt=17.419min, illustrate to contain → 6) α-Glcp (1 →.
Figure 11 is the fragment mass spectrum of Rt=19.761min, illustrate to contain → 4) α-Glcp (1 →.
Figure 12 is the fragment mass spectrum of Rt=23.296min, illustrate to contain → 4,6) α-Glcp (1 →.
Embodiment
Embodiment 1
With crude drug corydalis tuber 100g,, filter with 1 liter of deionized water soaking at room temperature 36 hours.Filtrate is evaporated to 200～300 milliliters for 50 ℃.Use 95% ethanol sedimentation then, the ethanol final concentration is 85%, precipitates 24 hours.Centrifugal, precipitation is with the dissolving of 200～300 ml waters, and is centrifugal, deionized water dialysis 48～72 hours.50 ℃ of concentrating under reduced pressure postlyophilizations promptly obtain corydalis tuber total polysaccharides YhPS-T5.77g, and recording polysaccharide content with the sulfuric acid phynol method is 65.1%.
Embodiment 2
With crude drug corydalis tuber 100g,, filter with 1 liter of deionized water soaking at room temperature 36 hours.Filtrate is evaporated to 200～300 milliliters for 50 ℃.Use acetone precipitation then, the acetone final concentration is 85%, precipitates 24 hours.Centrifugal, precipitation is with the dissolving of 200～300 ml waters, and is centrifugal, deionized water dialysis 48～72 hours.50 ℃ of concentrating under reduced pressure postlyophilizations promptly obtain corydalis tuber total polysaccharides YhPS-T5.68g, and recording polysaccharide content with the sulfuric acid phynol method is 67.0%.
Embodiment 3
YhPS-T is refining through the DEAE-Cellulose column chromatography, and the purity of YhPS can reach more than 90%.Concrete separation method: earlier with the glass column (0.05mol/LNaHCO of 2.8cm * 20cm)
3Balance 24 hours takes by weighing YhPS-T 150mg again, is dissolved in 3～5mL distilled water, centrifugal (4500r/min, 10min).Get supernatant liquor upper glass post, use the deionized water wash-out, flow velocity is 8mL/10min, and every pipe is collected 8mL, and about 8～24 pipes are absorption peak.Collect after deionized water was dialysed 48 hours, concentrating under reduced pressure obtains 52mg polysaccharide of rhizoma corydalis YhPS after the lyophilize, and purity can reach 93.1%.If need further to improve purity, can adopt the Sephadex gel column to do and be further purified.
YhPS-T is refining through the DEAE-Cellulose column chromatography, and YhPS purity can reach more than 90%.Concrete separation method: earlier with the glass column (0.05mol/LNaHCO of 2.8cm * 20cm)
3Balance 24 hours takes by weighing YhPS-T303mg again, is dissolved in 3～5mL distilled water, centrifugal (4500r/min, 10min).Get supernatant liquor upper glass post, use the deionized water wash-out, flow velocity is 8mL/10min, and every pipe is collected 8mL, and about 8～25 pipes are absorption peak.Collect after deionized water was dialysed 48 hours, concentrating under reduced pressure obtains 86.1mg polysaccharide of rhizoma corydalis YhPS after the lyophilize, and purity can reach 95.8%.If need further to improve purity, can adopt the Sephadex gel column to do and be further purified.
We are to the corydalis tuber total polysaccharides YhPS-T censorship biological activity determination of various dose, and its result is as follows:
1.YhPS-T sample is to the provide protection of focal cerebral ischemia in rats:
Get 50 of Wister rats, body weight 190～220g, male and female half and half are divided into 5 groups at random by body weight.Sham-operated control group, model control group, sample height (80mg/kg), in (40mg/kg), low (20mg/kg) dosage group, press 1ml/100g volume gastric infusion.Behind the medicine 1 hour, all rats with chloral hydrate anesthesia after (10mg/kg, ip), it is fixing to lie on the back, neck median incision exposes right carotid and external carotid artery and internal carotid artery, and branch's occipital artery of ligation external carotid artery, superior thyroid artery and external carotid artery end eventually prop up, separate the outer branch of internal carotid artery cranium pterygoid process arteria palatina, with silk thread ligation right carotid.
The rat of dosage group and medicine low dose group all inserts fishing line (0.3mm) from external carotid artery in ischemia model control group, medicine high dose group, the medicine, behind the careful importing internal carotid artery, fishing line continues to insert its intracranial segment, when feeling obvious resistance is arranged, the fishing line that inserts is about 19mm, and operation is local to cover with the warm saline gauze.The rat of Sham-operated control group does not insert fishing line, and all the other operations are identical.
Fishing line inserted postoperative 1 hour, carefully extracted fishing line out, multiple filling, layer-by-layer suture local organization, muscle, subcutaneous fascia and skin; After the sham operated rats exclusion 1 hour, layer-by-layer suture local organization, muscle, subcutaneous fascia and skin.
A. the study of behaviour of animal scoring: after operation end animal is clear-headed fully, carry out the 1st study of behaviour scoring immediately, operation 24 was as a child marked 1 time again, according to the standards of grading of bibliographical information, saw Table 1, carried out the study of behaviour evaluation respectively.The result carries out Ridit and analyzes, and sees Table 2.And its study of behaviour integration is organized a t check handle, see Table 3.
Table 1. neuroethology standards of grading
| Rank | Score value | The neuroethology performance |
| The I level | 0 minute | Behavior is normal fully |
| The II level | 1 minute | The left side fore paw can not launch fully |
| The III level | 2 minutes | Draw circle to the left side when moving ahead |
| The IV level | 3 minutes | Topple over to the left |
| The V |
4 minutes | Can not normally walk |
Table 2.YhPS-T sample is analyzed the neuroethology classification and the Ridit of cerebral ischemic model rat different time
| Group | Clear-headed neuroethology classification at once | |||||
| The I level | The II level | The III level | The IV level | The V level | Ridit analyzes | |
| Sham-operated |
8 | 2 | 0 | 0 | 0 | |
| Model control group | 0 | 0 | 0 | 2 | 8 | ### |
| High dose group | 0 | 1 | 1 | 2 | 6 | ### |
| Middle dosage group | 0 | 0 | 1 | 2 | 7 | ### |
| Low dose group | 0 | 0 | 1 | 1 | 8 | ### |
| The neuroethology classification in back 24 hours of performing the operation | ||||||
| The I level | The II level | The III level | The IV level | The V level | Ridit analyzes | |
| Sham-operated |
9 | 1 | 0 | 0 | 0 | |
| Model control group | 0 | 0 | 1 | 3 | 6 | ### |
| High dose group | 1 | 4 | 3 | 1 | 1 | ### ** |
| Middle dosage group | 0 | 4 | 2 | 3 | 1 | ### ** |
| Low dose group | 0 | 3 | 4 | 2 | 1 | ### ** |
Annotate: with Sham-operated control group than #P＜0.05, ##P＜0.01, ###P＜0.001;
With the model control group ratio
*P＜005,
*P＜0.01.
The influence that mark to the cerebral ischemic model rat behavior of table 3.YhPS-T sample (
, n=10)
| Group | The clear-headed scoring of study of behaviour at once | The 24 hours study of behaviour of performing the operation are marked |
| Sham-operated control group | 0.20±0.42 | 0.10±0.32 |
| Model control group | 3.80±0.42### | 3.50±40.71### |
| High dose group | 3.30±1.06### | 1.70±1.16### *** |
| Middle dosage group | 3.60±0.70### | 2.00±0.94### *** |
| Low dose group | 3.70±0.67### | 2.10±0.99### ** |
Annotate: with Sham-operated control group than ###P＜0.001;
With the model control group ratio
*P＜0.01,
* *P＜0.001.
B. coagulation time test: respectively at before the administration, when performing the operation and perform the operation and measured the clotting time in back 24 hours respectively,
Data are organized a statistical procedures, the results are shown in Table 4.
Table 4:YhPS-T sample to the influence in the clotting time of cerebral ischemic model rat different time (X ± S, n=10)
| Group | Clotting time (S) before the administration | Clotting time in the operation (S) | Perform the operation back 24 hour clotting time (S) |
| Sham-operated control group | 250.50±143.23 | 219.30±52.61 | 307.30±164.52 |
| Model control group | 238.20±73.21 | 156.10±58.27# | 176.00±95.19# |
| High dose group | 262.90±67.15 | 217.70±104.07 | 297.50±144.52 |
| Middle dosage group | 233.60±66.41 | 221.80±96.02 | 286.40±121.15 |
| Low dose group | 255.10±80.85 | 267.40±96.74** | 261.90±110.86 |
Annotate: with Sham-operated control group than #P＜0.05; With the model control group ratio
*P＜005,
*P＜0.01.
2.YhPS-T sample is to the influence of thrombus in vivo formation time
Get 40 of Wister rats, body weight 190～220g, male and female half and half are divided into 4 groups at random by body weight.Normal control group, the high, medium and low dosage group of sample, press 1ml/100g volume gastric infusion, behind the medicine 1 hour, rat was with vetanarcol anesthesia back (40mg/kg, ip) the fixedly median incision separation right carotid of lying on the back, adopt BT-87-3 type experiment thrombus in vivo to form determinator, at its nearly section stimulating electrode, the long-range thermoscope of putting is with the 2.0Ma galvanic current stimulation after 30 seconds, write down its thrombus formation time, calculate its rate elongation.The result organizes a t check, sees Table 5.
Table 5:YhPS-T sample to the influence of thrombus in vivo formation time (X ± S, n=10)
| Group | Dosage (mg/kg) | Thrombus formation time (S) | Rate elongation (%) |
| The normal control group | - | 189.90±160.70 | 0.00±0.00 |
| |
80 | 276.60±203.78* | 303.65±350.07 |
| |
40 | 248.20±213.76 | 151.03±149.91 |
| |
20 | 224.90±112.87 | 91.52±106.83 |
Annotate: with normal control group ratio
*P＜005.
Claims (12)
1. polysaccharide of rhizoma corydalis, its repeated structural unit is:
N=1～20 wherein.
2. polysaccharide of rhizoma corydalis as claimed in claim 1 is characterized in that molecular weight ranges is 2000～39000.
3. polysaccharide of rhizoma corydalis as claimed in claim 1 is characterized in that mainly being made up of glucose, also contains the semi-lactosi and the pectinose of trace.
4. as the production method of claim 1,2 or 3 described polysaccharide of rhizoma corydalis, it is characterized in that comprising that the crude drug corydalis tuber that drying is crossed is soaked in water, use organic solvent deposit, the precipitation water dissolution, supernatant liquor is behind dialysis or membrane sepn, concentrated, spray-dried or lyophilize obtains total polysaccharides, after the corydalis tuber total polysaccharides is dissolved in water, can get the pure product YhPS of polysaccharide of rhizoma corydalis through ion exchange column and gel column purifying; Described organic solvent is the organic solvent that dissolves each other with water.
5. the production method of polysaccharide of rhizoma corydalis as claimed in claim 4 is characterized in that the weight ratio corydalis tuber that crude drug corydalis tuber and water logging are steeped: water=1: 10～15, water-soaking time 24～36 hours, the pH=6.0 of soak solution～7.0.
6. the production method of polysaccharide of rhizoma corydalis as claimed in claim 4 is characterized in that described organic solvent is C
1～C
6Alcohol or ketone.
7. the production method of polysaccharide of rhizoma corydalis as claimed in claim 4 is characterized in that the ion-exchanger that described ion-exchange chromatography adopts is DEAE-Cellulose, DEAE-Sephacel, CM-Sephadex or Bio-Gel A type; The gel that described gel filtration chromatography adopted is Sephadex G type, SephacrylS type, Superose type, Bio-Gel P type or Superdex, and the separating ranges of selecting for use is 1 * 10
3-5 * 10
4Dalton.
8. the production method of polysaccharide of rhizoma corydalis as claimed in claim 4 is characterized in that dialysing or film that membrane sepn adopts, and its aperture is controlled at molecular weight cut-off 500～1000.
9. the purposes of polysaccharide of rhizoma corydalis as claimed in claim 1 is characterized in that described polysaccharide of rhizoma corydalis is used to prepare medicine or the healthcare products with cerebral ischemia provide protection.
10. the total polysaccharides of a polysaccharide of rhizoma corydalis, it is characterized in that by following method preparation: comprise that the crude drug corydalis tuber that drying is crossed is soaked in water, use organic solvent deposit, the precipitation water dissolution, supernatant liquor is behind dialysis or membrane sepn, and concentrated, spray-dried or lyophilize obtains total polysaccharides; Described organic solvent is the organic solvent that dissolves each other with water.
11. the production method of the total polysaccharides of polysaccharide of rhizoma corydalis as claimed in claim 10, it is characterized in that comprising that the crude drug corydalis tuber that drying is crossed is soaked in water, use organic solvent deposit, the precipitation water dissolution, supernatant liquor is behind dialysis or membrane sepn, and concentrated, spray-dried or lyophilize obtains total polysaccharides; Described organic solvent is the organic solvent that dissolves each other with water.
12. the purposes of the total polysaccharides of polysaccharide of rhizoma corydalis as claimed in claim 10 is characterized in that the total polysaccharides of described polysaccharide of rhizoma corydalis is used to prepare medicine or the healthcare products with cerebral ischemia provide protection.
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