CN101675934A - New use of saponins X of dipsacus asperoides - Google Patents
New use of saponins X of dipsacus asperoides Download PDFInfo
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- CN101675934A CN101675934A CN200810140248A CN200810140248A CN101675934A CN 101675934 A CN101675934 A CN 101675934A CN 200810140248 A CN200810140248 A CN 200810140248A CN 200810140248 A CN200810140248 A CN 200810140248A CN 101675934 A CN101675934 A CN 101675934A
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Abstract
The present invention provides a new use of saponins X of dipsacus asperoides, more conctretely relates to the application of the saponins X of dipsacus asperoides in preparing a medicine for treatingor preventing cardiovascular and cerebrovascular diseases. Compared with the nifedipine, the saponins X of dipsacus asperoides described by the present invention can obviously decrease the rising oflimb-lead electrocardiogram J point and reduce the ischemic areas in treating rat myocardial ischemia; and compared with nimodipine, the saponins X of dipsacus asperoides described by the present invention can obviously improve rat behavior disorder and reduce the ischemic areas in treating local cerebral ischemic injury.
Description
Technical field
The present invention relates to the new purposes of a kind of asperosaponin X, be specifically related to the application of a kind of asperosaponin X in the medicine of preparation treatment or prevention cardiovascular and cerebrovascular disease.
Background technology
The Chinese medicine Radix Dipsaci has invigorating the liver and kidney, bone and muscle strengthening, and continuous folding is hindered, and ends the effect of metrorrhagia, is used for soreness of the waist and knees, rheumatic arthralgia, metrorrhagia, vaginal bleeding during pregnancy, injury from falling down.Prepared RADIX DIPSACI with yellow rice wine is used for rheumatic arthralgia more, injury from falling down, and prepared RADIX DIPSACI with salt solution is used for soreness of the waist and knees more.Asperosaponin X extracts acquisition from Radix Dipsaci, be the effective ingredient of Radix Dipsaci.The effect of medicine in prevention or treatment cardiovascular and cerebrovascular disease that contains asperosaponin X do not appear in the newspapers.The inventor has invented a kind of medical usage of medicine in prevention or treatment cardiovascular and cerebrovascular disease that contains asperosaponin X by a large amount of experimentatioies.
Asperosaponin X structural formula (molecular formula: C
76H
124O
40Molecular weight: 1676)
Asperosaponin X chemical name: 3-O-(β-D-xylopyranose (1 → 4)-β-D-Glucopyranose. (1 → 4)) (α-L-pyrans rhamnose (1 → 3))-β-D-Glucopyranose. (1 → 3)-α-L-pyrans rhamnose (1 → 2)-α-L-arabopyranose-helexin-28-O-β-D-Glucopyranose. (1 → 6)-β-D-glucopyranosyl ester glycosides.
Summary of the invention
The invention provides the application of asperosaponin X in the medicine of preparation treatment or prevention cardiovascular and cerebrovascular disease.
The invention provides the application of asperosaponin X in the medicine of preparation treatment or prevention myocardial ischemia.
The invention provides the application of asperosaponin X in the medicine of preparation treatment or prevention of brain damage.
Asperosaponin X provided by the invention is when being used for above-mentioned arbitrary purposes, and the using dosage scope is 30mg～4000mg during its injection, is preferably 30mg～2000mg; The using dosage scope was 100mg～6000mg when it was oral, was preferably 100mg～3000mg.
It is the pharmaceutical composition of active component that the present invention also provides with asperosaponin X, and it can exist with the form of injectable powder, injection, tablet, capsule, soft capsule, drop pill or oral liquid, is preferably freeze-dried powder.Various dosage form provided by the invention all can adopt the pharmacy conventional method to be prepared from.
The inventor by following experiment confirm the effect (the following examples be used for more detailed description the present invention, but and do not mean that the present invention only limit to this) of this medicine at the treatment cardiovascular and cerebrovascular disease.
Description of drawings
The asperosaponin X mass spectrum of accompanying drawing 1 preparation example 1 gained
Instrument: Mariner Mass Spectum, cation spectrum, APCI; The methanol solution of solution concentration: 0.5mg/ml; Mobile phase: acetonitrile-water (3: 7).
The asperosaponin X nmr spectrum of accompanying drawing 2-9 preparation example 1 gained
Instrument: 400MHZ nuclear magnetic resonance analyser, solvent: methanol.
The specific embodiment
Preparation example 1: preparation asperosaponin X
Get 1 kilogram of Radix Dipsaci medical material,, cross 10 mesh sieves its pulverizing, add 10 times of amounts (V/W), 70% soak with ethanol and spend the night, reflux, extract, twice, each 2 hours, extracting liquid filtering, reclaiming ethanol does not extremely have the alcohol flavor, adds water and forms suspension, uses n-butanol extraction 3 times, merge lower aqueous layer, be splined on the D101 macroporous resin of handling well (resin and medical material weight ratio 1: 1), wash 3 column volumes, discard, 3 column volumes of reuse 30% ethanol elution, discard, wash 3 column volumes with 50% ethanol at last, collect 50% ethanol elution, concentrate, activated carbon decolorizing, recrystallization promptly gets content and is 98% asperosaponin X 6g.
Structure is identified:
White powder, mp 236-240 ℃, Liebermann and Molish reacting positive, FAB-MS m/z:1699 (M
++ Na), 1677 (M
++ H).
13Carbonyl carbon signal δ 178.10 of C-NMR demonstration (C=O, C-28), two double key carbon signal δ 123.76 (C-12), δ 144.93 (C-13), the end group carbon signal δ 105.65,105.27 of 8 sugar, 104.86,104.64,103.81,101.61,101.54,95.75, the methyl carbon signal δ 18.08,18.85 of two rhamnose.
1H-NMR shows the unimodal signal δ 0.70,0.80,0.91,0.94 of 6 methyl, 0.98, the doublet signal δ 1.20,1.25 of the methyl on 1.17, two rhamnose, above data in conjunction with document [Zhang Yongwen, Xue Zhi. the novel triterpenoid saponin in the Radix Dipsaci [J] Acta Pharmaceutica Sinica, 1991, (12); Zhang Yongwen, Xue Zhi. the chemical constitution study of Radix Dipsaci [J] Acta Pharmaceutica Sinica, 1991, (09); Zhang Yongwen, Xue Zhi. the structural research of Saponin IX and X [J] Acta Pharmaceutica Sinica in the Radix Dipsaci, 1992, (12)] contrast, determine that this chemical compound is asperosaponin X.
Preparation example 2: preparation asperosaponin X
Get 1 kilogram of Radix Dipsaci medical material,, cross 10 mesh sieves, add 10 times of amounts (V/W), 70% soak with ethanol and spend the night its pulverizing, reflux, extract, twice, each 2 hours, extracting solution reclaimed ethanol to there not being the alcohol flavor, and it is 80% that concentrated solution adds ethanol to determining alcohol, standing over night; Sucking filtration, filtrate is concentrated into does not have the alcohol flavor, adds 5 times of water gagings, standing over night, sucking filtration, the D101 macroporous resin that filtrate being splined on handled well (resin and medical material weight ratio 1: 1), 0.5% sodium hydroxide solution washes with water to neutrality after washing 2 column volumes, continues with 3 column volumes of 30% ethanol elution, discard, wash 3 column volumes with 50% ethanol at last, collect 50% ethanol elution, concentrated evaporate to dryness gets crude extract; Getting silicagel column on the above-mentioned crude extract, is that solvent carries out gradient elution with chloroform-methanol (3: 1), (2: 1), (1: 1), collects chloroform-methanol (1: 1) eluent, concentrates, and crystallization promptly gets content and be 98% asperosaponin X 10g.
Preparation example 3: preparation asperosaponin X
Get 1 kilogram of Radix Dipsaci medical material,, cross 10 mesh sieves, add 10 times of amounts (V/W), 70% soak with ethanol and spend the night its pulverizing, reflux, extract, twice, each 2 hours, extracting solution reclaimed ethanol to there not being the alcohol flavor, and it is 80% that concentrated solution adds ethanol to determining alcohol, standing over night; Sucking filtration, filtrate is concentrated into does not have the alcohol flavor, adds 5 times of water gagings, standing over night, filter, the D101 macroporous resin of handling well on the filtrate (resin and medical material weight ratio 1: 1), 1.0% sodium hydroxide solution washes with water to neutrality after washing 2 column volumes, continues with 3 column volumes of 30% ethanol elution, discard, wash 3 column volumes with 80% ethanol at last, collect 50% ethanol elution, concentrated evaporate to dryness gets crude extract; Getting silicagel column on the above-mentioned crude extract, is that solvent carries out gradient elution with chloroform-methanol (3: 1), (2: 1), (1: 1), collects chloroform-methanol (1: 1) eluent, concentrates, and crystallization promptly gets content and be 98% asperosaponin X 9g.
Preparation example 4: the preparation of asperosaponin X injection:
Prescription: asperosaponin X 3.0g
Sodium chloride 89g
Water for injection 10000ml
Make 10000ml
Method for making:
Measure asperosaponin X 3.0g by prescription, sodium chloride 89g with water for injection 10000ml dissolving, stirs; The active carbon of adding 0.2% stirred 20 minutes, and solution is clear and bright through filtering with microporous membrane, be sub-packed in the 125ml infusion bottle, and every bottle of 100mL, sterilization, packing gets final product after the passed examination.Other checks that item should meet Pharmacopoeia of People's Republic of China version injection in 2005 project demand.
Preparation example 5: asperosaponin X freeze-dried powder preparation
Get asperosaponin X 30g, add injection water 2000ml after the mixing, with mannitol 8g, stirring and dissolving, ultrafiltration obtains apyrogenic clear liquor, pours in the 10ml cillin bottle, and 2ml/ only presses the lyophilizing of freeze-dried powder technology, makes every freeze-dried powder that contains 30mg.
Preparation example 6: asperosaponin X solid tablet preparation:
Prescription: asperosaponin X 100g
Starch 150g
Dextrin 50g
Microcrystalline Cellulose 100g
Magnesium stearate is an amount of
Carboxymethyl starch sodium is an amount of
5%,PVP,K30 60% ethanol is an amount of
Make 1000
Method for making: measure asperosaponin X 100g, starch 150g, dextrin 50g, microcrystalline Cellulose 100g by prescription, magnesium stearate, carboxymethyl starch sodium are an amount of, and be mixed, adds 5%,PVP,K30 60% alcoholic solution and granulate drying in right amount, granulate, tabletting, after the passed examination, packing.
Test example 1: asperosaponin X is to the influence of rat heart muscle ischemic injuries
(1) material:
Asperosaponin X:, provide by natural drug Engineering Technical Research Centre modern Chinese medicine research department, Shandong Province by preparation example 1 preparation.Chlorination nitro blue tetrazolium (N-BT) is provided by Military Medical Science Institute medical supply station.
Laboratory animal: regular grade SD rat, male, body weight 280g-350g, male and female half and half, Shandong Green Leaf Pharmaceutical Co., Ltd's Experimental Animal Center provides, the quality certification number: SYXK (Shandong) 20030020.
(2) method and result:
Animal is divided into model control group (normal saline) at random, Nifedipine group (6mg/kg), asperosaponin X (3mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) intravenously administrable group, asperosaponin X (50mg/kg) intravenously administrable group, asperosaponin X (100mg/kg) intravenously administrable group, asperosaponin X (200mg/kg) intravenously administrable group, asperosaponin X (400mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) gastric infusion group, asperosaponin X (30mg/kg) gastric infusion group, asperosaponin X (100mg/kg) gastric infusion group, asperosaponin X (300mg/kg) gastric infusion group, asperosaponin X (600mg/kg) gastric infusion group.Every group 10.After the fasting 12 hours, limbs II lead electrocardiogram is surveyed in ip. urethane (1.2g/kg) anesthesia.Cut off left front fur, iodine tincture and alcohol disinfecting, along left border of sternum 1cm place, cut off thoracic wall muscle and two ribs, open the thoracic cavity rapidly, expose heart, the ligation left coronary artery is put back to heart immediately between arterial cone and left auricle, squeezes the thoracic cavity air, use the mosquito forceps closed-chest, cause Model Rats with Acute Myocardial Ischemia.Nifedipine group is gastric infusion before anesthesia, composition oral dosage group successive administration 3 days, and fasting is after 16 hours after administration in the 2nd day, and administration in the 3rd day was performed the operation after 30 minutes, and all the other respectively organize postoperative with both intravenous injection relative medicines.1.5h, 3h electrocardiogram before the record administration and after the administration measure the lift-off value of electrocardiogram J point, take out heart behind the 6h, with cold saline clean after ,-20 ℃ of refrigerator freeze overnight.Next day, refrigerated heart is cut into 5 by ligation place to apex uniform thickness, immerse in the freshly prepared 0.25%N-BT phosphate buffer (pH 7.4).37 ℃ of water-bath jolting 10～15min.Blot the dyeing liquor of slice surface with filter paper, separate the coloured portions and the part of being unstained, weigh the compute infarct size.Infarct size (%)=infarction part weight/(non-infarction part weight+infarction part weight) * 100%.Data are represented with X ± s, carry out statistical procedures with t check between group.
The result is as shown in table 1, and myocardial ischemia is after 6 hours, and tangible kitchen range shape ischemic region appears in the model group rat heart muscle, reaches about 26%.Asperosaponin X (3mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) intravenously administrable group, asperosaponin X (50mg/kg) intravenously administrable group, asperosaponin X (200mg/kg) intravenously administrable group, asperosaponin X (400mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) gastric infusion group, asperosaponin X (30mg/kg) gastric infusion group, asperosaponin X (100mg/kg) gastric infusion group, asperosaponin X (300mg/kg) gastric infusion group, asperosaponin X (600mg/kg) gastric infusion group reduces the rising of limb lead electrocardiogram J point significantly, reducing ischemic areas (compares with model group, p＜0.05 or p＜0.01), asperosaponin X (200mg/kg) intravenously administrable group is to the rising of limb lead electrocardiogram J point, reduce ischemic areas and asperosaponin X (400mg/kg) intravenously administrable group relatively, there was no significant difference (p＞0.05); Asperosaponin X (300mg/kg) gastric infusion group compares there was no significant difference (p＞0.05) to rising, minimizing ischemic areas and asperosaponin X (600mg/kg) the gastric infusion group of limb lead electrocardiogram J point.
Table 1 asperosaponin X is to the influence (n=10) of rat heart muscle ischemic injuries
Compare with model control group,
*P＜0.05,
*P＜0.01
Test example 2: asperosaponin X is to the influence of rat local cerebral ischemia damage
(1) material:
Asperosaponin X:, provide by natural drug Engineering Technical Research Centre modern Chinese medicine research department, Shandong Province by preparation example 1 preparation.
Red tetrazolium: U.S. Sigma company product, face with preceding and be made into 4% solution with normal saline.
Laboratory animal: regular grade SD rat, male, body weight 280g-350g, male and female half and half, Shandong Green Leaf Pharmaceutical Co., Ltd's Experimental Animal Center provides, the quality certification number: SYXK (Shandong) 20030020.
(2) method and result:
Animal is divided into model control group (normal saline) at random, the nimodipine group (Nim, 1.0mg/kg), asperosaponin X (3mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) intravenously administrable group, asperosaponin X (50mg/kg) intravenously administrable group, asperosaponin X (100mg/kg) intravenously administrable group, asperosaponin X (200mg/kg) intravenously administrable group, asperosaponin X (400mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) gastric infusion group, asperosaponin X (30mg/kg) gastric infusion group, asperosaponin X (100mg/kg) gastric infusion group, asperosaponin X (300mg/kg) gastric infusion group, asperosaponin X (600mg/kg) gastric infusion group.Every group 10.Every group 10.After the fasting 12 hours, and chloral hydrate (350mg/kg, i.p.) anesthesia separates right carotid, and folder closes in the neck, common carotid artery, external carotid artery proximal part and distal end ligation, cut off the centre.The external carotid artery free-end is pulled to internal carotid artery in alignment, bolt line (selecting diameter 0.24mm nylon wire for use, length 5.0cm) is inserted into intracranial by external carotid artery, stop when meeting slight resistance, insertion depth is about 2cm.Ligation external carotid artery opening, and open the common carotid artery bulldog clamp, the disinfection and stitching wound causes right side middle cerebral artery ischemia model; Sham operated rats is only carried out the separation (above experiment is all carried out at 23 ℃～25 ℃) of right carotid, internal carotid artery, external carotid artery.Composition oral dosage group successive administration 3 days, fasting is after 16 hours after administration in the 2nd day, and administration in the 3rd day was performed the operation after 30 minutes, and all the other respectively organize postoperative intravenous injection relative medicine.Press document [Liu Xiaoguang, Xu Lina, a kind of rat brain medium-sized artery model that can estimate thrombolytic and anti-thrombolytic after 24 hours, Acta Pharmaceutica Sinica, 1995,30:662] described method and standard is observed and the behavior disorder of record rat: (A) carry the Mus tail and observe forelimb flexing situation, stretch to ground as two forelimb symmetries, count 0 fen, the wrist flexing occurs as operation offside forelimb and count 1 fen, the elbow flexing is counted 2 fens, the shoulder inward turning is counted 3 fens, existing wrist flexing and/or elbow flexing have shoulder inward turning person again, count 4 fens.(B) animal is placed on the plane earth, push away both shoulders respectively, check resistance to side shifting.As bilateral resistance equity and strong, count 0 fen, as resistance descender when the operation offside promotes, according to decline degree difference be divided into gently, in, weigh three degree, count 1,2 and 3 fen respectively.(C) the two forelimbs of animal are put on the wire netting, observed the muscular tension of two forelimbs.Two muscle of anterior limb tension force equities and strong person count 0 fen.Count 1,2 and 3 fen according to operation offside muscular tension decline degree difference equally.(D) animal has ceaselessly to a side person of turn-taking, and counts 1 fen.According to the standard scoring, full marks are 11 minutes, and mark is high more, and expression animal behavior obstacle is serious more.
Put to death rat behind the behavior scoring, get brain, remove olfactory bulb, cerebellum and low brain stem, crownly be cut into 5, the brain sheet takes on a red color after normal structure is dyed with red tetrazolium (TTC) dyeing, and blocking tissue is white in color, taking a picture in dyeing back, asks the infarct size ratio with Chinese Aero-Space university pathological image analysis software.Data are represented with X ± s, carry out statistical procedures with t check between group.
The result is as shown in table 2, and ischemia is after 24 hours, and the model group rat shows tangible behavior disorder, and tangible kitchen range shape ischemic region also appears in rat cerebral tissue, reaches full brain about 24%.Asperosaponin X (3mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) intravenously administrable group, asperosaponin X (50mg/kg) intravenously administrable group, asperosaponin X (200mg/kg) intravenously administrable group, asperosaponin X (400mg/kg) intravenously administrable group, asperosaponin X (10mg/kg) gastric infusion group, asperosaponin X (30mg/kg) gastric infusion group, asperosaponin X (100mg/kg) gastric infusion group, asperosaponin X (300mg/kg) gastric infusion group, asperosaponin X (600mg/kg) gastric infusion group is improved the rat behavior obstacle significantly, reducing ischemic areas (compares with model group, p＜0.05 or p＜0.01), asperosaponin X (200mg/kg) intravenously administrable group is to improving the rat behavior obstacle, reduce ischemic areas and asperosaponin X (400mg/kg) intravenously administrable group relatively, there was no significant difference (p＞0.05); Asperosaponin X (300mg/kg) gastric infusion group is to improving rat behavior obstacle, minimizing ischemic areas and asperosaponin X (600mg/kg) gastric infusion group relatively, there was no significant difference (p＞0.05).
Table 2 asperosaponin X is to the influence (n=10) of rat cerebral ischemia damage
Compare with model control group,
*P＜0.05,
*P＜0.01
Claims (3)
1. the application of asperosaponin X in the medicine of preparation treatment or prevention cardiovascular and cerebrovascular disease.
2. the application of asperosaponin X in the medicine of preparation treatment or prevention myocardial ischemia.
3. the application of asperosaponin X in the medicine of preparation treatment or prevention of brain damage.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103622983A (en) * | 2013-11-18 | 2014-03-12 | 滨州医学院 | Application of radix dipsaci saponin X in preparation of medicines for preventing or treating pulmonary fibrosis |
| CN107582560A (en) * | 2017-10-13 | 2018-01-16 | 杨中林 | The thrombus dissolving effect and its application of akebiasaponin D |
| CN107875157A (en) * | 2017-11-10 | 2018-04-06 | 中国药科大学 | The application of hederagenin and its glucosides in the medicine for preparing preventing and treating cerebral apoplexy |
| CN111333694A (en) * | 2020-04-28 | 2020-06-26 | 吉林省中医药科学院（吉林省中医药科学院第一临床医院） | Application of helexin derivatives in anti-myocardial hypoxia-reoxygenation injury drugs |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101161251B (en) * | 2007-11-22 | 2011-02-09 | 广州博济医药生物技术有限公司 | Teasel root total saponin as well as its extracting method and application |
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2008
- 2008-09-19 CN CN200810140248A patent/CN101675934B/en active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103622983A (en) * | 2013-11-18 | 2014-03-12 | 滨州医学院 | Application of radix dipsaci saponin X in preparation of medicines for preventing or treating pulmonary fibrosis |
| CN103622983B (en) * | 2013-11-18 | 2015-12-30 | 滨州医学院 | Radix Dipsaci saponins X prevents in preparation or treats the application in the medicine of pulmonary fibrosis |
| CN107582560A (en) * | 2017-10-13 | 2018-01-16 | 杨中林 | The thrombus dissolving effect and its application of akebiasaponin D |
| CN107582560B (en) * | 2017-10-13 | 2020-02-28 | 杨中林 | Thrombolytic effect of akebia saponin D and application thereof |
| CN107875157A (en) * | 2017-11-10 | 2018-04-06 | 中国药科大学 | The application of hederagenin and its glucosides in the medicine for preparing preventing and treating cerebral apoplexy |
| CN111333694A (en) * | 2020-04-28 | 2020-06-26 | 吉林省中医药科学院（吉林省中医药科学院第一临床医院） | Application of helexin derivatives in anti-myocardial hypoxia-reoxygenation injury drugs |
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|---|---|
| CN101675934B (en) | 2012-10-03 |
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| C56 | Change in the name or address of the patentee | ||
| CP03 | Change of name, title or address |
Address after: 646607 Luzhou city of Sichuan province Wangjiang town ponds Longmatan district road two No. six, No. eight Patentee after: Sichuan green leaf pharmaceutical Limited by Share Ltd Address before: 646100 Luzhou city of Sichuan province Wangjiang town ponds Longmatan district road two No. 6 Patentee before: SICHUAN LVYE BAO GUANG PHARMACEUTICAL INDUSTRY CO., LTD. |