CN1445244A - Lilyturf root polysaccharide MDG-1 and its separation method and application - Google Patents
Lilyturf root polysaccharide MDG-1 and its separation method and application Download PDFInfo
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Abstract
An ophiopogon polyose MDG-1 with the action of treating myocardial ischemia, its preparing process and its application are disclosed. It is the beta-D-fructosan with 5000 of molecular weight.
Description
Technical field:
The present invention relates to active ingredient of Chinese herbs and extraction and separation method, be specifically related to have MDG-1 polysaccharide of lilyturf root-1 and the separation method and the application of function of resisting myocardial ischemia.
Background technology:
Be the dried root of Liliaceae Ophiopogon plant (Ophiopogon Japonicus (L.f) Ker-Gawl) tuber of dwarf lilyturf, is enriching yin Chinese medicine commonly used simply, and the beginning is stated from Shennong's Herbal, and the successive dynasties, important book on Chinese herbal medicine was all on the books.It has nourishing Yin and promoting production of body fluid, the function that moistening lung clears away heart-fire.We find when studying Radix Ophiopogonis extract to the coronary heart disease and angina pectoris preventive and therapeutic effect, Radix Ophiopogonis polysaccharide can increase dirty coronary flow of guinea-pig heart and mouse cardiac muscle nutritional blood flow amount, the ECG ST section that antagonism dog coronary ligation causes is raised etc., and tangible function of resisting myocardial ischemia is arranged.Therefore, Radix Ophiopogonis polysaccharide can be used for the control of coronary heart disease and angina pectoris clinically, has the excellent development prospect.
But at present Radix Ophiopogonis polysaccharide is only rested on the extraction of efficient part, Shang Weiyou is separated to the active polysaccharide of homogeneous molecular weight.
Summary of the invention:
Technical problem to be solved by this invention is by Radix Ophiopogonis polysaccharide is carried out classification by molecular weight, carries out the pharmacodynamics screening then, finds out efficient part, and further separation and purification, and a kind of homogeneous molecular weight that has is provided, and the active polysaccharide of pharmaceutical use is arranged.
The MDG-1 polysaccharide of lilyturf root-the 1st that obtains through separation and purification disclosed by the invention, molecular weight is β-D-Polylevulosan of 5000, based on 2 → 1 furan type fructose that connect, on average per 2.8 backbone groups a Fruf (2 → 6) Fruf (2 → branch) is arranged, the reducing end of this polysaccharide links to each other with α-D-Glc.
Another technical problem to be solved by this invention is the extraction and separation method that discloses above-mentioned MDG-1 polysaccharide of lilyturf root-1.
The extraction and separation method of MDG-1 polysaccharide of lilyturf root disclosed by the invention-1 comprises the following steps:
1. the extraction of Radix Ophiopogonis polysaccharide
Get the drying piece root tuber of dwarf lilyturf, flattening is doubly measured the 70%-95% alcohol reflux 3 times with 5-6, abandons it, and dregs of a decoction water is carried 2-3 time, the water extract is evaporated to 0.5-1g/ml, add 75%-95% ethanol and reach 60%-80% to containing the alcohol amount, standing over night, supernatant liquor inclines, precipitation repeats alcohol precipitation 1 time, lyophilize gets faint yellow Radix Ophiopogonis polysaccharide powder, yield about 20%;
2. the ultra-filtration and separation of Radix Ophiopogonis polysaccharide
The tuber of dwarf lilyturf total polysaccharides, 15 times of dilute with waters, 10000 molecular weight membrane ultrafiltration, pressure are 3.5 normal atmosphere, after 70 ℃ of ultrafiltrateds concentrate, lyophilize.
3. the purifying of Radix Ophiopogonis polysaccharide
Get Radix Ophiopogonis polysaccharide 2g, less water dissolving, last DEAE SepharoseFF post, water, 0.1-4mol Nacl gradient elution, washing part peak position is collected in the online detection of anthrone-sulfuric acid process, after the lyophilize, SephadexG50 post on the water dissolution, water elution, merge peak position, the SephadexG25 post is gone up in lyophilize again, water elution merges peak position, lyophilize, obtain white powder, be MDG-1 polysaccharide of lilyturf root-1.
Adopting high-efficient liquid phase technique to carry out purity to the MDG-1 polysaccharide of lilyturf root-1 that obtains with extracting method of the present invention identifies:
Chromatographic condition: SHODEX KS802 chromatographic column, moving phase are water, flow velocity 1ml/min, and 80 ℃ of column temperatures, detector are ELSD.Polysaccharide dissolves with suitable quantity of water, and sample introduction is single symmetrical peak, illustrates that this component is the polysaccharide of molecular weight homogeneous.See Fig. 1.
The MDG-1 polysaccharide of lilyturf root-1 that obtains with extracting method of the present invention is carried out structure determination:
MDG-1 differentiates through purity, proves it is single composition, can carry out structural analysis.
MDG-1 is through all-hydrolytic, and sample only contains a kind of monose, i.e. fructose.Among the IR 933
-1And 820
-1Two distinctive absorption peaks of Polylevulosan prove that also this polysaccharide is a Polylevulosan.From
13103-104ppm anomeric carbon signal proves that this polysaccharide is a beta comfiguration among the CMNR, can learn that from methylation analysis this polysaccharide is 2 → 1 and 2 → 6 Polylevulosan that connect, and the mode of connection of this furan type has
13C reaches
1Further confirmed in HNMR and periodates oxidizing reaction and the Smith degraded.
Above-mentioned analytical proof: MDG-1 is β-D-Polylevulosan, based on 2 → 1 furan type fructose that connect, on average per 2.8 backbone groups a Fruf (2 → 6) Fruf (2 → branch) is arranged.The reducing end of this polysaccharide may link to each other with α-D-Glc.
A technical problem more to be solved by this invention is to disclose the application of above-mentioned MDG-1 polysaccharide of lilyturf root-1 in preparation treatment medicaments for resisting myocardial ischemia.
MDG-1 polysaccharide of the present invention can be used as activeconstituents and pharmaceutical excipient makes the medicine that resists myocardial ischemia, and its formulation can comprise all kinds of medically acceptable pharmaceutical dosage forms.
Carry out relevant pharmacodynamic study with the injection that contains the MDG-1 polysaccharide 62% that the inventive method makes:
Experiment is observed the Radix Ophiopogonis polysaccharide injection liquid and Pituitrin is brought out the effect of rat coronary artery spasm by using the ECG ST section shift value as index; By use heart function (LVSP, LVDP, LVEDP, ± LVdp/dt), blood pressure and hrv parameter (SAP, DAP, MAP, HR), seroenzyme creatine kinase (CK), serum lactic dehydrogenase (LDH) and oxyradical such as superoxide-dismutase (SOD), mda (MDA), the heart NBT myocardial infarction area of measuring that dyes, the painted cardiomorphologies of HE etc. are as index, observe the effect of Radix Ophiopogonis polysaccharide injection liquid to Acute Myocardial Ischemia in Rats (infraction) due to the coronary artery ligation.
1 materials and methods
1.1 Pituitrin brings out the experiment of rat coronary artery spasm
78 of healthy, male SD kind rats (body weight 243 ± 19g) administration in advance, administration are divided into following each group:
The blank group: intraperitoneal injection of saline 8ml/kg, anaesthetize behind the 15min, detect electrocardiogram(ECG.
Positive controls: the abdominal injection pannonit (Mingxing Pharmaceutical Factory, Guangzhou, lot number: 000601) 10mg/kg, anaesthetize behind the 15min, detect electrocardiogram(ECG.
The heavy dose of group of Radix Ophiopogonis polysaccharide injection liquid (po): irritated stomach Radix Ophiopogonis polysaccharide injection liquid in advance 3 days, 1g/kg, every day 1 time, 1h anesthesia detects electrocardiogram(ECG after the last administration.
Dosage group in the Radix Ophiopogonis polysaccharide injection liquid (po): irritated stomach Radix Ophiopogonis polysaccharide injection liquid in advance 3 days, 0.3g/kg, every day 1 time, 1h anesthesia detects electrocardiogram(ECG after the last administration.
Radix Ophiopogonis polysaccharide injection liquid (po) small dose group: irritated stomach Radix Ophiopogonis polysaccharide injection liquid in advance 3 days, 0.1g/kg, every day 1 time, 1h anesthesia detects electrocardiogram(ECG after the last administration.
The (iv) heavy dose of group of Radix Ophiopogonis polysaccharide injection liquid: tail vein injection Radix Ophiopogonis polysaccharide injection liquid 50mg/kg, 10min anesthesia detects electrocardiogram(ECG after the administration.
The (iv) middle dosage group of Radix Ophiopogonis polysaccharide injection liquid: tail vein injection Radix Ophiopogonis polysaccharide injection liquid 15mg/kg, 10min anesthesia detects electrocardiogram(ECG after the administration.
The Radix Ophiopogonis polysaccharide injection liquid is small dose group (iv): tail vein injection Radix Ophiopogonis polysaccharide injection liquid 5mg/kg, 10min anesthesia detects electrocardiogram(ECG after the administration.
Animal abdominal injection 25% urethane (Shanghai Cao Yang second chemical plant, lot number: 1998422) 1.6g/kg anesthesia, connecing limbs two leads, stablize 15mim, use processing of Power/Lab4S type bio signal and analytical system record rat electrocardiogram(ECG, select the no abnormal person's sublingual vein of electrocardiogram(ECG injection of pituitrin (Shanghai biochemical-pharmaceutical factory, lot number: 000627) 0.5u/kg, 5sec behind the record injection of pituitrin, 15sec, 30sec, 1min, 2min, 5min, electrocardiogram(ECG during 10min changes, and calculates 0sec～30sec, the ST section shift value of 30sec～10min time period.
1.2 coronary artery ligation causes Acute Myocardial Ischemia in Rats (infraction) experiment
1) rat coronary artery ligation
Healthy, male 180 (body weight 241 ± 20g) of Wistar kind rat, intraperitoneal injection of ketamine (Shanghai Westen and Chinese Tranditional Medicine Pharamacentic Co., Ltd, lot number: 010701) 80mg/kg anesthesia, dorsal position is fixed, connecing limbs two leads, handle and analytical system monitoring electrocardiogram(ECG by Power/Lab4S type bio signal, insert trachea cannula by the oral cavity, connect animal breathing apparatus (DH-140B type, Zhejiang Medical university medical instrument demonstration plant) is positive pressure respiration (Tidal volume 10ml/kg, during breathing than 1: 1, respiratory rate 60 times/minute).Routine disinfection, the 3rd rib that fractures struts the thoracic cavity with machine for chest-opening, expose heart, cut off pericardium, expose heart, rapidly heart is extruded, with No. 5/0 non-invasive silk thread, between pulmonary conus and left auricle of heart, apart from the about 2mm of aortic root place's ligation left anterior descending coronary artery (sham operated rats threading, not ligation), extract air in the thoracic cavity out, sew up rapidly and close chest, recover to close animal respirator after the autonomous respiration.ECG ST section is significantly raised expression modeling success.
2) experiment grouping
Healthy, male Wistar kind rat is divided into following each group at random:
Sham-operation (sham) group: irritated stomach physiological saline in advance 3 days, 8ml/kg, every day 1 time.
Ischemic (AMI) group: irritated stomach physiological saline in advance 3 days, 8ml/kg, every day 1 time.
Propranolol (Pro) group: irritate in advance the stomach propranolol (Propranolol, Shanghai Xin Pasi pharmaceutical Co. Ltd, lot number: 010221) 3 days, 15mg/kg, every day 1 time.
The heavy dose of group of Radix Ophiopogonis polysaccharide injection liquid (po): irritate 3 days Radix Ophiopogonis polysaccharide injection liquids of stomach in advance, 1g/kg, every day 1 time.
Dosage group in the Radix Ophiopogonis polysaccharide injection liquid (po): irritate 3 days Radix Ophiopogonis polysaccharide injection liquids of stomach in advance, 0.3mg/kg, every day 1 time.
Radix Ophiopogonis polysaccharide injection liquid (po) small dose group: irritate 3 days Radix Ophiopogonis polysaccharide injection liquids of stomach in advance, 0.1mg/kg, every day 1 time.
The heavy dose of group of Radix Ophiopogonis polysaccharide injection liquid (ip): 3 days Radix Ophiopogonis polysaccharide injection liquids of abdominal injection in advance, 0.2g/kg, every day 1 time.
Dosage group in the Radix Ophiopogonis polysaccharide injection liquid (ip): 3 days Radix Ophiopogonis polysaccharide injection liquids of abdominal injection in advance, 0.06g/kg, every day 1 time.
Radix Ophiopogonis polysaccharide injection liquid (ip) small dose group: 3 days Radix Ophiopogonis polysaccharide injection liquids of abdominal injection in advance, 0.02g/kg, every day 1 time.
1h carries out the left anterior descending coronary artery ligation operation after the administration in the 3rd day, and the modeling winner continued administration 3 days.1h handles by Power/Lab4S type bio signal and analytical system is measured heart function and hemodynamic index after the administration in the 6th day, or cores and dirtyly make morphological observation (HE dyeing, NBT dye), or the activity of getting the determination of serum enzyme.
3) haemodynamics is measured
Each treated animal is through abdominal injection vetanarcol (Shanghai chemical reagent purchasing and supply station; lot number: 860122) 30mg/kg anesthesia, sublingual vein injecting heparin sodium (Changzhou thousand red pharmaceutical Co. Ltds, lot number: 000830) 1200u/kg; tracheostomize inserts trachea cannula.Separate right carotid, insert heart catheter, the output terminal of heart catheter connects high-precision pressure transverter (MLT1050 type), heart catheter writes down arteriotony in arteria carotis communis, behind the continous-stable record 10min, heart catheter is pushed into left ventricle, record left ventricular pressure (LVSP, LVDP, LVEDP), left indoor pressure rate of change (LVdp/dt) curve, periphery blood pressure (SAP, DAP, MAP) and heart rate (HR).
4) serum zymetology and determination of oxygen free radicals
Femoral artery blood drawing 5ml from each treated animal left standstill 2 hours, centrifugal (2,000rpm) 5 minutes, get supernatant liquor and be kept at-70 ℃.When measuring seroenzyme, sample thaws behind the sample fully, measures creatine kinase (CK), serum lactic dehydrogenase (LDH), superoxide-dismutase (SOD), mda (MDA) content in the serum according to the explanation of test kit by 722 type grating spectrophotometers (Shanghai the 3rd analytical instrument factory).The consumption of sample is 20 μ l when measuring CK, and LDH is that 4 μ l, SOD are that 7 μ l, MDA are 100 μ l.20011124), SOD test kit (lot number: 20020221), MDA test kit (lot number: 20020205) all purchase and build up bio-engineering research institute, LDH test kit (lot number: 20010401) purchase in Nanjing CK test kit (lot number: in Shanghai Biological Products Inst., Ministry of Public Health.
5) heart NBT dyeing
Fresh heart cuts off the atrium along the coronary artery ditch, rejects non-cardiac muscular tissues such as blood vessel, fat,, claim weight in wet base.Take out after putting-4 ℃ of freezing about 1h, along coronary sulcus from the apex of the heart to the parallel myocardium sheet of heart base portion with ventricular muscles crosscut Cheng Houyue 0.1cm, put into 0.1% NBT (AMRESCO) solution with normal saline flushing after clean, the 10min that dyes under 37 ℃ of water bath condition removes unnecessary dyestuff with distilled water flushing after the dyeing immediately.Infarcted region is not painted, and infarcted region is dyed bluish voilet, cuts infarcted myocardium, inhales the branch that anhydrates with filter paper, claims weight in wet base, and the per-cent that accounts for the ventricle weight in wet base with the infarcted region weight in wet base is represented myocardial infarction area.
6) cardiomorphology
Open the rat thoracic cavity, take out heart rapidly, remove blood stains through normal saline flushing, reject non-cardiac muscular tissues such as blood vessel, fat, inhale the branch that anhydrates with filter paper, insert in the 10% neutral formalin solution and fix, after 24 hours, row paraffin embedding, section, dyeing are put and are made myocardium morphological observation under the opticmicroscope.
7) statistical study
All experimental result is all represented with mean ± standard error or standard deviation.With the significance of data between student t-check or one way ANOVA check comparative group, the P value is less than 0.05, and expression has the significance meaning
2. result
2.1 the Radix Ophiopogonis polysaccharide injection liquid is used amplitude that the ST section raises as index to the effect of rat acute coronary spasm due to the Pituitrin, behind blank group intravenous injection Pituitrin 0～30sec, the amplitude that the ST section is raised obviously increases (table 1), and pannonit and Radix Ophiopogonis polysaccharide injection liquid can suppress due to the Pituitrin ST section effectively and raise.In 30sec～10minST section, compare there was no significant difference between each group.Table 1. Radix Ophiopogonis polysaccharide injection liquid is to the influence of Acute Myocardial Ischemia in Rats ECG ST section due to the Pituitrin (x ± s)
(μ v) for ST section shift value
The group columns
0s～30s 30s～10m
The heavy dose of group 10 51.2 ± 18.8 of Radix Ophiopogonis polysaccharide injection liquid (po)
*33.8 ± 19.6
Radix Ophiopogonis polysaccharide injection liquid (po) small dose group 10 65.2 ± 9.0
*28.3 ± 13.2
The (iv) heavy dose of group 10 64.0 ± 22.1 of Radix Ophiopogonis polysaccharide injection liquid
*26.3 ± 18.5
The (iv) middle dosage group 10 56.2 ± 20.8 of Radix Ophiopogonis polysaccharide injection liquid
*27.3 ± 15.4
The Radix Ophiopogonis polysaccharide injection liquid is small dose group 10 56.0 ± 21.2 (iv)
*18.9 ± 10.2
*
Annotate: compare with the blank group,
*P＜0.05,
*P＜0.01.
2.2 the HS-4 coronary artery ligation causes the effect of Acute Myocardial Ischemia in Rats (infraction)
1) variation of myocardial infarction area
Cardiac muscle is through NBT dyeing, and the phenomenon of myocardial infarction is not seen by discovery sham operated rats cardiac muscular tissue.Rat was through ligation coronary artery 3 days, the area of myocardial infarction is about 25%, the positive control drug propranolol can dwindle the scope of myocardial infarction, uses the Radix Ophiopogonis polysaccharide injection liquid of different concns different modes of administration and handles, and the scope that reduces myocardial infarction is had certain effect.(seeing Table 2).Table 2. Radix Ophiopogonis polysaccharide injection liquid is to the influence of Acute Myocardial Infarction rat myocardium block area (x ± s)
Group columns myocardial infarction area (%)
Myocardial infarction group 6 25.57 ± 2.83
Proprasylyte group 6 19.88 ± 3.60
The heavy dose of group 6 23.78 ± 3.29 of Radix Ophiopogonis polysaccharide injection liquid (po)
Dosage group 6 21.15 ± 2.65 in the Radix Ophiopogonis polysaccharide injection liquid (po)
#
Radix Ophiopogonis polysaccharide injection liquid (po) small dose group 6 23.25 ± 4.07
The heavy dose of group 6 20.08 ± 2.25 of Radix Ophiopogonis polysaccharide injection liquid (ip)
##
Dosage group 6 19.50 ± 0.98 in the Radix Ophiopogonis polysaccharide injection liquid (ip)
##
Radix Ophiopogonis polysaccharide injection liquid (ip) small dose group 6 23.10 ± 3.61
Annotate: compare with the myocardial infarction group,
#P＜0.05,
##P＜0.01.
2) heart function and haemodynamics
A) to the influence of heart function
The sham operated rats rat is compared, LVSP, the LVDP of heart stalk group rat, LVEDP ,+dp/dt
Max,-dp/dt
MaxEvery index obviously descend (P＜0.01).Cardiac functional parameter of propranolol group rat and heart stalk group compare, except that LVEDP variant (P＜0.05), and all other there was no significant differences.The Radix Ophiopogonis polysaccharide injection liquid respectively organize rat hemodynamic parameter and heart stalk group relatively, the decline of LVSP is had some improvement (P＜0.01), but to the leading indicator+dp/dt of reaction myocardial contractility
MaxInfluence is little, and only the dosage group can significantly raise+dp/dt in the Radix Ophiopogonis polysaccharide injection liquid (ip)
MaxValue (P＜0.05); Radix Ophiopogonis polysaccharide injection liquid (po) has the trend of improving myocardial compliance (reduction of LVEDP) for three groups, but compare with heart stalk group, only the dosage group has notable difference (P＜0.01) in the Radix Ophiopogonis polysaccharide injection liquid (po), and three groups of nothings of raising to LVEDP of Radix Ophiopogonis polysaccharide injection liquid (ip) influence.
B) to the decline that acute myocardial ischemia causes the periphery blood pressure that influences of blood pressure, heart rate, heart stalk group rat with sham operated rats relatively, except that systolic pressure (SAP) has significant difference (P＜0.05), diastolic pressure (DAP) and mean pressure (MAP) indifference.Heart rate of heart stalk group rat and sham operated rats relatively obviously weaken (P＜0.01).Blood pressure of propranolol group rat and changes in heart rate and heart stalk group compare, there was no significant difference.The blood pressure and the heart stalk group of each group of Radix Ophiopogonis polysaccharide injection liquid compare, all no significant difference; Aspect heart rate, each group of Radix Ophiopogonis polysaccharide injection liquid (po) can suppress the decreased heart rate (P＜0.05) that myocardial ischemia causes.
Table 3.1 Radix Ophiopogonis polysaccharide injection liquid (po) is to acute myocardial ischemia rat (n=10) heart function
(the influence of x ± s)
Radix Ophiopogonis polysaccharide injection liquid (po)
Index S ham AMI Pro
Dosage low dose in the heavy dose
LVSP(mmHg) 179.4±12.4 143.1±15.8
** 136.7±14.6 164.2±13.6
## 153.2±14.4 160.9±10.7
##
LVDP(mmHg) -11.4±3.1 2.7±2.8
** 0.4±4.2 -4.7±3.7
## -4.6±4.9
## -4.9±3.5
##
LVEDP(mmHg) 6.2±2.5 14.1±2.6
** 11.3±1.7
# 12.2±2.6 9.8±2.2
## 12.9±2.4
±dp/dt(mmHg/s) 7721.8±749.3 4986.9±781.6
** 4711.0±591.2 5492.3±596.9 5584.8±651.2 5248.7±712.9
-dp/dt(mmHg/s) -5083.5±557.3 -3298.8±691.6
** -3182.5±638.5 -3497.3±412.2 -3741.8±371.9 -3502.7±567.4
Annotate: compare with the Sham group,
*P＜0.05,
*P＜0.01; Compare with the AMI group,
#P＜0.05,
##P＜0.01。
Table 3.2 Radix Ophiopogonis polysaccharide injection liquid (ip) is to acute myocardial ischemia rat (n=10) heart function
(the influence of x ± s)
Radix Ophiopogonis polysaccharide injection liquid (ip)
Index S ham AMI Pro
Dosage low dose in the heavy dose
LVSP(mmHg) 179.4±12.4 143.1±15.8
** 136.7±14.6 161.0±10.1
##?161.2±9.0
## 151.4±16.7
LVDP(mmHg) -11.4±3.1 2.7±2.8
** 0.4±4.2 0.9±3.7 1.2±3.7 2.8±3.9
LVEDP(mmHg) 6.2±2.5 14.1±2.6
** 11.3±1.7
# 14.8±4.9 12.5±3.4 15.1±3.6
+dp/dt(mmHg/s) 7721.8±749.3 4986.9±781.6
** 4711.0±591.2 5415.6±542.8 5628.6±500.6
#?5183.8±977.6
-dp/dt(mmHg/s)?-5083.5±557.3 -3298.8±691.6
** -3182.5±638.5?-3542.9±450.4?-3618.2±474.0 -3018.8±668.1
Annotate: compare with the Sham group,
*P＜0.05,
*P＜0.01; Compare with the AMI group,
#P＜0.05,
##P＜0.01。
Table 4.1 Radix Ophiopogonis polysaccharide injection liquid (po) is to acute myocardial ischemia rat (n=10) blood pressure and the heart
Rate (the influence of x ± s)
Radix Ophiopogonis polysaccharide injection liquid (po)
Index S ham AMI Pro
Dosage low dose in the heavy dose
SAP(mmHg) 147.3±15.6 130.6±16.1
*?124.3±11.4 140.7±9.5 136.4±103 136.9±7.5
DAP(mmHg) 106.2±13.8 98.7±14.3 91.9±10.8 108.4±8.3 99.8±6.8 102.2±6.8
MAP(mmHg) 120.6±12.2 109.3±14.5 102.8±11.4 118.4±7.7 112.0±7.1 116.2±6.4
HR(b/min) 421.0±24.7 384.6±20.4
**317.4±26.0 406.7±23.2
#?406.5±24.4
#?415.7±27.0
##
Annotate: compare with the Sham group,
*P＜0.05,
*P＜0.01; Compare with the AMI group,
#P＜0.05,
##P＜0.01。
Table 4.2 Radix Ophiopogonis polysaccharide injection liquid (ip) is to acute myocardial ischemia rat (n=10) blood pressure and the heart
Rate (the influence of x ± s)
Radix Ophiopogonis polysaccharide injection liquid (ip)
Index S ham AMI Pro
Dosage low dose in the heavy dose
SAP(mmHg) 147.3±15.6 130.6±16.1
*?124.3±11.4 142.5±9.6 139.6±6.0 129.5±11.4
DAP(mmHg) 106.2±13.8 98.7±14.3 91.9±10.8 104.6±7.2 102.3±5.9 97.9±13.2
MAP(mmHg) 120.6±12.2 109.3±14.5 102.8±11.4 117.4±8.0 115.2±5.6 109.5±12.2
HR(b/min) 421.0±24.7 384.6±20.4
**317.4±26.0 397.8±31.6 396.9±27.3 358.8±25.5
Annotate: compare with the Sham group,
*P＜0.05,
*P＜0.01; Compare with the AMI group,
#P＜0.05,
##P＜0.01。
3) activity of seroenzyme and oxyradical
When myocardial ischemia myonecrosis when development entad, just the reversibility pathology is when the non-reversibility pathological development, and myocardial cell's membrane permeability increases, and myocardium enzyme discharges obviously to be increased, and makes that the content of enzyme increases in the serum.The active increase of CK and LDH in the serum illustrates that irreversible damage has appearred in cardiac muscle.As seen, heart stalk group rat blood serum CK and LDH are active to be compared with sham operated rats, obviously increases (P＜0.01) from table 4.Propranolol can not suppress myocardial ischemia and cause CK and the active increase of LDH in the serum.Dosage group active increase of CK in serum when all significantly (P＜0.01) suppresses myocardial ischemia in dosage group and the Radix Ophiopogonis polysaccharide injection liquid (ip) in the Radix Ophiopogonis polysaccharide injection liquid (po), the effect of the heavy dose of group of Radix Ophiopogonis polysaccharide injection liquid (ip) take second place (P＜0.05); And cause aspect the Serum LDH increase suppressing myocardial ischemia, each group of Radix Ophiopogonis polysaccharide injection liquid (po) and the heavy dose of effect of organizing of Radix Ophiopogonis polysaccharide injection liquid (ip) are remarkable.
During acute myocardial ischemia, oxyradical generates increases the consumption increase that causes SOD, and causes membrane phospholipid generation lipid peroxidation, makes film forming damage, and the dead end product MDA of a large amount of lipid peroxidations produces to be increased.As seen, behind the acute myocardial ischemia, the active obviously reduction of SOD and the generation of MDA obviously increase from table 5.Propranolol can not improve the reduction of the SOD that myocardial ischemia causes and the increase of MDA.The SOD that the dosage group causes myocardial ischemia in dosage group and the Radix Ophiopogonis polysaccharide injection liquid (ip) in the Radix Ophiopogonis polysaccharide injection liquid (po) reduces obvious restraining effect, the dosage group can significantly suppress MDA in the Radix Ophiopogonis polysaccharide injection liquid (po) increases, and other each group is little to the influence that SOD reduces and MDA increases.Table 5. Radix Ophiopogonis polysaccharide injection liquid is to (the influence of x ± s) of acute myocardial ischemia rat blood serum enzymic activity
Group n CK (U/ml) LDH (IU/L)
Radix Ophiopogonis polysaccharide injection liquid (po) heavy dose of 10 254.86 ± 81.49 538.30 ± 171.17
##
Radix Ophiopogonis polysaccharide injection liquid (po) low dose of 10 278.72 ± 50.56 598.30 ± 162.31
#
Radix Ophiopogonis polysaccharide injection liquid (ip) heavy dose of 10 230.04 ± 93.91
#479.01 ± 189.86
#
Radix Ophiopogonis polysaccharide injection liquid (ip) low dose of 10 282.86 ± 105.11 764.48 ± 387.64
Annotate: compare with the Sham group,
*P＜0.01; Compare with the AMI group,
#P＜0.05,
##P＜0.01.
Table 6.HS-4 is to acute myocardial ischemia rat blood serum SOD and the MDA (influence of x ± s)
Group n SOD (NU/ml) MDA (nmol/ml)
Radix Ophiopogonis polysaccharide injection liquid (po) heavy dose of 10 389.84 ± 52.39 3.15 ± 0.99
Radix Ophiopogonis polysaccharide injection liquid (po) low dose of 10 363.44 ± 46.87 3.49 ± 0.70
Radix Ophiopogonis polysaccharide injection liquid (ip) heavy dose of 10 399.70 ± 36.56 2.80 ± 0.54
Radix Ophiopogonis polysaccharide injection liquid (ip) low dose of 10 374.17 ± 65.70 3.33 ± 0.80
Annotate: compare with the Sham group,
*P＜0.01; Compare with the AMI group,
#P＜0.05,
##P＜0.01.
4) myocardial pathology analysis
Its lesion degree is observed through fixing, embedding, section and HE dyeing by cardiac muscular tissue.Myocardial necrosis kitchen range lesion degree discrimination standard :-: necrosis region is not seen by cardiac muscular tissue; +: the intralesional cardiac muscle is total necrosis not, wherein is mingled with a small amount of not downright bad myocardial cell; ++: coagulation necrosis or lytic necrosis all take place in the intralesional myocardial cell.
Pathology (-) is not seen by sham operated rats (n=4) cardiac muscular tissue, and visceral pericardium has the mild inflammation reaction or do not have, and sees that a small amount of neutrophil leucocyte and mononuclearcell soak into.
The scope of model group cardiac muscle is 35.0 ± 4.1% (n=4), focus of infarct is the map shape, the large stretch of myocardial cell of intralesional is dissolved or is partly dissolved, accompany a large amount of mononuclearcells to soak into and a small amount of neutrophil infiltration, visible large stretch of coagulation necrosis kitchen range between the dissolving necrotic area, this district's nucleus has dissolved or pyknosis, only surplus cell outline (++); Visceral pericardium shows no obvious abnormalities.
The scope of positive control drug propranolol group myocardial infarction is 38.8 ± 4.8% (n=4), has the myocardial cell's major part between the 1 example dissolving necrotic area to remain (+) alive, other 3 routine same model group (++) in the pathology.
The scope of the heavy dose of group of Radix Ophiopogonis polysaccharide injection liquid (po) myocardial infarction is 26.3 ± 7.5% (n=4), have in the pathology 1 routine lesion degree for+, be partly dissolved the myocardial cell that necrotic zone still has survival, in addition 3 routine same model group (++).
The scope of dosage group myocardial infarction is 30.0 ± 9.1% (n=4) in the Radix Ophiopogonis polysaccharide injection liquid (po), the same model group of pathology (++).
The scope of Radix Ophiopogonis polysaccharide injection liquid (po) small dose group myocardial infarction is 38.8 ± 2.5%, the same model group of pathology (++).
The heavy dose of group of Radix Ophiopogonis polysaccharide injection liquid (ip) myocardial infarct size is 16.3 ± 7.5% (n=4), the same model group of pathology (++).
Dosage group myocardial infarct size is 28.8 ± 6.3% (n=4) in the Radix Ophiopogonis polysaccharide injection liquid (ip), have in the pathology 1 routine lesion degree for+, be partly dissolved the myocardial cell that necrotic zone still has survival, in addition 3 routine same model group (++).
Radix Ophiopogonis polysaccharide injection liquid (ip) small dose group myocardial infarct size is 36.3 ± 10.3% (n=4), the same model group of pathology (++).
3. brief summary:
Pituitrin can make coronary artery that acute spasm takes place, and causes acute blood supply insufficiency and Peripheral resistance to increase, and causes cardiac load to increase the weight of, and the T ripple of visible reflecting myocardium ischemic is raised with the S-T section and raised on electrocardiogram(ECG.When ligation animal coronary artery, Electrocardiographic S-T section is raised an important indicator that can be used as myocardial infarction.This experimental result shows that but T ripple that Radix Ophiopogonis polysaccharide injection liquid antagonism Pituitrin causes is raised with the S-T section to be raised, the S-T section that raises behind the ligation rat coronary artery is obviously reduced, illustrate that the Radix Ophiopogonis polysaccharide injection liquid has the effect of anti-acute myocardial ischemia, its mechanism may relate to the increase of coronary dilation and coronary flow.
With NBT substantially the sample staining measure Radix Ophiopogonis polysaccharide injection liquid that myocardial infarction area shows different way of administration, various dose the scope of the myocardial infarction that caused by coronary ligation had certain effect that reduces.Behind the myocardial ischemia that the painted myocardial pathology analysis revealed of HE coronary ligation causes, tangible myocardial cell's sex change, the downright bad variation are arranged under the cardiac muscular tissue under the light microscopic.The interior large stretch of myocardial cell of focus of infarct is dissolved or is partly dissolved, and accompanies a large amount of mononuclearcells to soak into and a small amount of neutrophil infiltration.The sex change and the degree of necrosis of the cardiac muscular tissue of the animal of handling through the Radix Ophiopogonis polysaccharide injection liquid alleviate not obvious.It is the earliest phenomenon that myocardial contraction during myocardial ischemia weakens, and its mechanism mainly is because the ATP due to the metabolic disturbance reduces, potassium loss in the cell, and inorganic phosphate increases, and oxypathy in the cell causes myocardium E-C coupling obstacle.The Radix Ophiopogonis polysaccharide injection liquid has decline that improves the shrinkage that acute myocardial ischemia causes and the trend of improving the conformability (reduction of LVEDP) of cardiac muscle, but DeGrain.Generally speaking, myocardial ischemia is after 6 hours, the active increase of CK and LDH in the serum, when myocardial ischemia myonecrosis when development entad, just the reversibility pathology is when the non-reversibility pathological development, and myocardial cell's membrane permeability increases, myocardium enzyme discharges obviously to be increased, and makes that the content of enzyme increases in the serum.The active increase of CK and LDH in the serum illustrates that irreversible damage has appearred in cardiac muscle.The Radix Ophiopogonis polysaccharide injection liquid can reduce CK and the rising of LDH content in the coronary ligation animal serum, and prompting Radix Ophiopogonis polysaccharide injection liquid can be protected the myocardial cell, increases the ischemia resisting anoxic ability of cell, improves the stability of film, prevents the further necrosis of cardiac muscle.During acute myocardial ischemia, oxyradical generates increases the consumption increase that causes SOD, and causes membrane phospholipid generation lipid peroxidation, makes film forming damage, and the dead end product MDA of a large amount of lipid peroxidations produces to be increased.The SOD that the Radix Ophiopogonis polysaccharide injection liquid causes myocardial ischemia reduces and MDA increases certain restraining effect is arranged, and illustrate that the Radix Ophiopogonis polysaccharide injection liquid has the effect that free radical that myocardial ischemia causes generates increase and removing oxyradical that suppresses.
MDG-1 polysaccharide of lilyturf root disclosed by the invention-1, function of resisting myocardial ischemia is remarkable, and a kind of active polysaccharide with pharmaceutical use is provided.
Description of drawings:Fig. 1 MDG-1 high-efficient liquid phase technique purity collection of illustrative plates Fig. 2 MDG-1 acetylize gets acetyl derivatives gas phase figure Fig. 3 standard sugar gas phase collection of illustrative plates Fig. 4 MDG-1 KBr pressed disc method infared spectrum Fig. 5 MDG-1 of sugar alcohol
13CNMR spectrogram 6 MDG-1
1Gas phase figure Fig. 8 MDG-1 oxidation behind the H NMR spectrogram 7 MDG-1 exhaustive methylations, Smith degraded back gas phase figure
Embodiment:The preparation of embodiment 1 MDG-1 polysaccharide of lilyturf root-1
1. the extraction of Radix Ophiopogonis polysaccharide
Get the drying piece root 1kg tuber of dwarf lilyturf, 5-6 doubly measures 80% alcohol reflux 3 times, and each 1 hour, dregs of a decoction water was carried 2-3 time, each 30 minutes.The water extract is evaporated to 1g/ml, and add 95% ethanol and reach 70% to containing the alcohol amount, standing over night, the supernatant liquor that inclines, precipitation repeats alcohol precipitation 1 time, and lyophilize gets faint yellow Radix Ophiopogonis polysaccharide powder.
2. the ultra-filtration and separation of Radix Ophiopogonis polysaccharide
The tuber of dwarf lilyturf, total polysaccharides diluted 15 times, and 10000 molecular weight membrane ultrafiltration, pressure are 3.5 normal atmosphere, after 70 ℃ of ultrafiltrateds concentrate, and lyophilize.
3. the purifying of Radix Ophiopogonis polysaccharide
Get Radix Ophiopogonis polysaccharide 2g, less water dissolving, last DEAE SepharoseFF post, water, 0.1-4molNacl gradient elution, washing part peak position is collected in the online detection of anthrone-sulfuric acid process, after the lyophilize, SephadexG50 post on the water dissolution, water elution, merge peak position, the SephadexG25 post is gone up in lyophilize again, water elution, merge peak position, lyophilize obtains white powder.
4. the purity of purified polysaccharide is identified
Adopt high-efficient liquid phase technique: chromatographic condition: SHODEX KS802 chromatographic column, moving phase are water, flow velocity 1ml/min, and 80 ℃ of column temperatures, detector are ELSD.Polysaccharide dissolves with suitable quantity of water, and sample introduction is single symmetrical peak, sees Fig. 1.Embodiment 2, MDG-1 polysaccharide of lilyturf root-1 structure determination
(1) sugar component decomposes (all-hydrolytic)
Sample MDG-1 is through 110 ℃ of tube sealing hydrolysis of 2M trifluoroacetic acid 1h, and hydrolyzed solution is evaporated to dried, and then adds methyl alcohol secondary, evaporate to dryness more repeatedly.Be dissolved in less water, the aqueous solution is divided into A and B two portions.A part point sample carries out the cellulose sheet chromatography, and compares with standard monose, found that hydrolyzed solution has only a spot, and its Rf value is consistent with fructose, infers the Polylevulosan that MDG-1 may be made up of fructose thus.The B part is reduced with NaBH4, the acetic acid neutralization, and the concentrating under reduced pressure evaporate to dryness adds the methyl alcohol secondary more repeatedly; evaporate to dryness again, acetylize gets the acetyl derivatives of sugar alcohol then, carries out gas chromatography; the result compares with standard diagram (Fig. 3) as shown in Figure 2, corresponds respectively to glucose and seminose.Because Polylevulosan is furan type ketose ring, epimerization can take place behind reductive hydrolysis, generate sorbitol and mannitol.Result according to the thin plate chromatography can think that this polysaccharide is the furan type Polylevulosan.Certainly its net result also will confirm through NMR.
(2) infrared absorption spectrum
Sample adopts the KBr pressed disc method to measure, the result as shown in Figure 4, MDG-1 presents the absorption feature of typical polysaccharide from IR figure, at wave number 933cm
-1And 820cm
-1Absorption peak be the special pick up the oil signal of Polylevulosan, this shows that this polysaccharide is-Polylevulosan.
(3) NMR (Nuclear Magnetic Resonance) spectrum
1H reaches
13The analysis of CNMR spectrum
Sample is dissolved in D
2Among the O, normal temperature is measured down, the results are shown in Figure 5,6.From
13Visible (Fig. 5) anomeric carbon signal of CNMR spectrum illustrates that at 103-104ppm anomeric carbon all is beta comfiguration, and the reference literature data are as follows to each signal ownership:
LINKAGES C-1 C-2 C-3 C-4 C-5 C-6
Fruf(2→ 60.8 104.1 76.8 74.7 81.5 62.8
→1)Fruf(2→ 62.6 103.6 76.8 74.7 81.5 62.8
→6)Fruf(2→ 60.6 104.2 76.8 74.7 80.5 63.5
1，6)Fruf(2→ 60.8 104.1 76.8 74.7 80.5 63.5
1There is not strong signal in the anomer hydrogen district in the H spectrum (Fig. 6), this illustrates that once more this polysaccharide is a Polylevulosan, because fructose is ketose, does not have proton on its 2 anomeric carbons, in the hydrogen spectrum a different more weak signal is arranged, may derive from α-D-Glc that reduction end common in the Polylevulosan connects.
(4) methylation reaction
Take by weighing the about 8mg of exsiccant MDG-1 sample in reaction flask, add the dry DMSO2ml that crosses in the room temperature magnetic agitation, the dissolving back adds Powdered exsiccant NaOH powder 20mg, stirring at room 10min, and then in ice bath, stir 10min, slowly add 0.6mlCH
3I, reaction 30min, the reaction solution concentrating under reduced pressure removes excessive CH
3I, to the water dialysis, the dialyzate lyophilize, the reaction triplicate methylates fully until the IR demonstration.
Behind the MDG-1 exhaustive methylation, be hydrolyzed to the monose of part methylization, be converted into the alditol acetate of part methylization through reduction acetyl, carrying out GC-MS analyzes, eight peaks (Fig. 7) appear in the result, and these eight peaks can be divided into four groups, and this is because certain of bonding that connects thinks that fructose is transformed into the derivative of corresponding mannitol and sorbitol when reduction, so two peaks appear in the fructose of each part methylization in GC, both represent components contents at sum.The result of methylation analysis this polysaccharide as can be known mainly is made up of 2 → 1 and 2 → 6 fructose that connect.
(5) periodates oxidizing reaction and Smith DeR
Sample MDG-1 is dissolved in 0.015M NaIO
4In, in room temperature reaction below 20 ℃ a couple of days, 24h spectrophotometry OD at interval
224Measure NaIO
4Consume, found that oxidizing reaction in the 3rd day fully.The result shows that the average every mole of hexose residue of periodates oxidation consumes sodium periodate 0.93ml, illustrates that thus 3 and 4 hydroxyls of fructose do not replace, and further specifies this polysaccharide and is connected to the master with 2 → 1 or 2 → 6.With above-mentioned oxidation completely sample carry out Smith degraded, be about to oxidation sample NaIO completely
4Reduction 10h, acetic acid neutralization, dialysis; lyophilize; hydrolysis then, acetylize, GC analyzes; the result as shown in Figure 8; from the visible primary product of result is glycerol, and glycerol is adjacent diatomic alcohol compounds degraded product, illustrates that oxidation occurs in 3; between 4 the vicinal hydroxyl groups, prove that further this polysaccharide mainly is made up of 2 → 1 and 2 → 6 furan type fructose that connect.
Claims (5)
1, a kind of Radix Ophiopogonis polysaccharide, it is characterized in that this polysaccharide is that molecular weight is β-D-Polylevulosan of 5000, based on 2 → 1 furan type fructose that connect, on average per 2.8 backbone groups a Fruf (2 → 6) Fruf (2 → branch) is arranged, the reducing end of this polysaccharide links to each other with α-D-Glc.
2, a kind of preparation method of Radix Ophiopogonis polysaccharide as claimed in claim 1 is characterized in that the preparation of described polysaccharide comprises the following steps:
1) extraction of Radix Ophiopogonis polysaccharide
Get the drying piece root tuber of dwarf lilyturf, flattening is doubly measured the 70%-95% alcohol reflux 3 times with 5-6, abandons it, and dregs of a decoction water is carried 2-3 time, the water extract is evaporated to 0.5-1g/ml, add 75%-95% ethanol and reach 60%-80% to containing the alcohol amount, standing over night, supernatant liquor inclines, precipitation repeats alcohol precipitation 1 time, lyophilize gets faint yellow Radix Ophiopogonis polysaccharide powder, yield about 20%;
2) ultra-filtration and separation of Radix Ophiopogonis polysaccharide
The tuber of dwarf lilyturf total polysaccharides, 15 times of dilute with waters, 10000 molecular weight membrane ultrafiltration, pressure are 3.5 normal atmosphere, after 70 ℃ of ultrafiltrateds concentrate, lyophilize;
3) purifying of Radix Ophiopogonis polysaccharide
Get Radix Ophiopogonis polysaccharide, less water dissolving, last DEAE SepharoseFF post, water, 0.1-4molNacl gradient elution, washing part peak position is collected in the online detection of anthrone-sulfuric acid process, after the lyophilize, SephadexG50 post on the water dissolution, water elution, merge peak position, the SephadexG25 post is gone up in lyophilize again, water elution merges peak position, lyophilize, obtain white powder, be MDG-1 polysaccharide of lilyturf root-1.
3, a kind of preparation method of Radix Ophiopogonis polysaccharide as claimed in claim 2 is characterized in that the Radix Ophiopogonis polysaccharide powder through the extraction acquisition, after the ultra-filtration and separation, respectively through DEAE SepharoseFF post, SephadexG50 post and SephadexG25 column purification.
4, the application of a kind of Radix Ophiopogonis polysaccharide as claimed in claim 1 in preparation treatment medicaments for resisting myocardial ischemia.
5, a kind of application of Radix Ophiopogonis polysaccharide as claimed in claim 4 is characterized in that this polysaccharide is used to prepare the medicine that resists myocardial ischemia as activeconstituents.
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