CN1817898A - Use of anti-inflammatory medicine for scheelite total saponin and its saponin compound - Google Patents

Use of anti-inflammatory medicine for scheelite total saponin and its saponin compound Download PDF

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CN1817898A
CN1817898A CN 200610024750 CN200610024750A CN1817898A CN 1817898 A CN1817898 A CN 1817898A CN 200610024750 CN200610024750 CN 200610024750 CN 200610024750 A CN200610024750 A CN 200610024750A CN 1817898 A CN1817898 A CN 1817898A
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glaucogenin
glycosyl
pyrans
saponin
scheelite
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CN100443498C (en
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张卫东
郑兆广
张川
苏娟
沈云亨
柳润辉
孔令义
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Second Military Medical University SMMU
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Abstract

Vincetoxin, its saponin compound and use in antiphlogistic medicine are disclosed. The vincetoxin consists of bine vincetoxin A, bine vincetoxin B, bine vincetoxin C, bine vincetoxin D, vincetoxicoside C-3-O-beta-D-thevetoside, vincetoxicoside C, vincetoxicoside H, atratoglaucosides A and cynanosides I. Vincetoxin is mixture which contains any kinds of the nine compounds with content >50%. It has excellent inhibiting function for various inflammations and can be used to treat chronic pharyngitis, chronic enterogastritis, acute tonsillitis and upper respiratory infection.

Description

The application in anti-inflammatory drug of scheelite total saponin(e and saponin compound thereof
Technical field
The invention belongs to medical technical field, be specifically related to the compound that a class has anti-inflammatory activity, radix cynanchi atrati saponin compound that especially extraction separation obtains from the Chinese medicine radix cynanchi atrati and scheelite total saponin(e, and in prevention with treat application in the various acute or chronic inflammation medicines.
Background technology
Radix cynanchi atrati is the root of the upright radix cynanchi atrati of asclepiadaceae (Asclepiadaceae) Cynanchum plant (Cynanchum atratumBunge.), Cynanchum versicolor Bunge (Cynanchum versicolor Bunge.), radix cynanchi atrati has the effect that clearing heat and cooling blood, inducing diuresis for treating stranguria syndrome, detoxifcation are treated sore in the theory of traditional Chinese medical science, is used for that temperature is evil hinders diseases such as battalion's heating, fever due to yin deficiency, hectic fever due to yin labor heat, postpartum fever due to deficiency of blood, heat pouring, blood pouring, swollen ulcer drug.Aqueous extract and alcohol extract to radix cynanchi atrati carried out some pharmacological researches in recent years, the extract that studies show that radix cynanchi atrati have bring down a fever, effect such as antimicrobial antiphlogistic and analgesia,
So far, still find no total saponins of radix cynanchi atrati and the bibliographical information that monomer saponin is made medicine thereof, the contriver confirms through great deal of experimental, scheelite total saponin(e and monomer saponin thereof have anti-inflammatory action, can prevent and treat various acute or chronic inflammations, and made medicament, finished the present invention.
Summary of the invention
The object of the present invention is to provide extraction obtains from the Chinese medicinal materials radix cynanchi atrati radix cynanchi atrati saponin compound and scheelite total saponin(e, and propose its application in anti-inflammatory drug.
The present invention's extraction separation from radix cynanchi atrati obtains having 9 kinds of carbon-21 steroidal saponin(es of anti-inflammatory activity, be specially: Cynanversicoside A, Cynanversicoside B, Cynaversicoside C, Cynaversicoside D, glaucogenin C-3-O-β-D-Semen Thevetiae glucosides, glaucoside C, Glaucoside H, atratoglaucosides A, cynanosides I, and obtain comprising in 9 kinds of carbon-21 steroidal saponin(es several arbitrarily and the mixture of saponin compound total content (weight) 〉=50% is the scheelite total saponin(e.
Detect by analysis, 9 kinds of carbon-21 steroidal saponin(es among the present invention are 9 kinds of glucosides that a kind of and different quantities, the dissimilar sugar by 3 kinds of steroid sapogenins shown in following 3 chemical structures forms, and wherein R is a sugar chain:
Figure A20061002475000041
glaucogenin A glaucogenin C glaucogenin D
Cynanversicoside A: aglycon is Glaucogenin C (glaucogenin C), and R is the lucky pyrans of β-D-Apocynum cannabinum pyranose-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyrans glycosyl.
Cynanversicoside B: aglycon is Glaucogenin C (glaucogenin C), and R is the lucky pyrans of β-D-glucopyanosyl base-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyrans glycosyl.
Cynaversicoside C: aglycon is Glaucogenin D (Cynanchum glaucescens aglycon D), and R is β-D-Semen Thevetiae pyrans glycosyl.
Cynaversicoside D: aglycon is Glaucogenin D (Cynanchum glaucescens aglycon D), and R is the lucky pyrans of β-D-Apocynum cannabinum pyranose-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyrans glycosyl.
Glaucogenin C-3-O-β-D-Semen Thevetiae glucosides: aglycon is Glaucogenin C (glaucogenin C), and R is β-D-Semen Thevetiae pyrans glycosyl.
Glaucoside C: aglycon is Glaucogenin A (Cynanchum glaucescens aglycon A), and R is the lucky pyrans of α-L-Apocynum cannabinum pyrans glycosyl-(1 → 4)-β-D-enlightening glycosyl-(1 → 4)-β-L-Apocynum cannabinum pyrans glycosyl.
Glaucoside H: aglycon is Glaucogenin A (Cynanchum glaucescens aglycon A), and R is the lucky pyrans of β-D-glucopyanosyl base-(1 → 4)-α-L-Apocynum cannabinum pyrans glycosyl-(1 → 4)-β-D-enlightening glycosyl-(1 → 4)-β-L-Apocynum cannabinum pyrans glycosyl.
Atratoglaucosides A: aglycon is Glaueogenin C (glaucogenin C), and R is the lucky pyrans of α-L-enlightening glycosyl-(1 → 4)-β-D-Folium seu Cortex Nerii pyrans glycosyl.
Cynanosides I: aglycon is Glaucogenin A (Cynanchum glaucescens aglycon A), and R is the lucky pyrans of β-D-glucopyanosyl base-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl.
The present invention further proposes scheelite total saponin(e and radix cynanchi atrati saponin compound or is that the composition of primary activity composition is in prevention with treat the purposes of various acute or chronic inflammations and related diseases thereof with it, acute or chronic inflammation comprises upper respiratory tract infection, tonsillitis, pharyngolaryngitis, gastro-enteritis, pneumonia, trachitis, inflammation such as phlebitis.
Scheelite total saponin(e and radix cynanchi atrati saponin compound can become pharmaceutical composition with pharmaceutically acceptable vehicle group, make various preparations, comprising: tablet, granule, capsule, oral liquid, dripping pill, mixture, syrup, tincture, injection etc.Route of administration is oral, and through skin, snuffing is gone into, rectum, parenteral, vein or muscle etc.
Chemical part
Carbon-21 steroidal saponin(e provided by the invention and the mixture scheelite total saponin(e that includes any kind of carbon-21 steroidal saponin(e, their preparation method is, the radix cynanchi atrati medicinal material with ethanol etc. as extracting solvent, concentrating the medicinal extract that obtains separates through macroporous resin column chromatography, collect ethanol eluate, concentrate and obtain the scheelite total saponin(e.Again through silica gel column chromatography, detect the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, concentrate, separate and purifying through the RP-18 post again, get Cynanversicoside A, Cynanversicoside B, Cynaversicoside C, Cynaversicoside D, glaucogenin C-3-O-β-D-Semen Thevetiae glucosides, glaucoside C, Glaucoside H, atratoglaucosides A, cynanosides I.
By spectral analysis techniques such as acid hydrolysis and UV spectrum, infrared spectra, high resolution fast atom bombardment MS, proton nmr spectra, carbon-13 nmr spectra, the relevant spectrum of heteronuclear volume, the relevant spectrums of heteronuclear multikey, the chemical structure of 9 kinds of carbon-21 steroidal saponin(es is illustrated, and is respectively: the lucky pyrans of Glaucogenin C (glaucogenin C)-3-O-(1 → 4)-β-D-Apocynum cannabinum pyranose-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyranoside; The lucky pyrans of Glaucogenin C (glaucogenin C)-3-O-(1 → 4)-β-D-glucopyanosyl base-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyranoside; Glaucogenin D (Cynanchum glaucescens aglycon D)-3-O-(1 → 4)-β-D-Semen Thevetiae pyranoside; The lucky pyrans of Glaucogenin D (Cynanchum glaucescens aglycon D)-3-O-(1 → 4)-β-D-Apocynum cannabinum pyranose-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyranoside; Glaucogenin C (glaucogenin C)-3-O-β-D-Semen Thevetiae pyranoside; The lucky pyrans of GlaucogeninA (Cynanchum glaucescens aglycon A)-3-O-(1 → 4)-α-L-Apocynum cannabinum pyrans glycosyl-(1 → 4)-β-D-enlightening glycosyl-(1 → 4)-β-L-Apocynum cannabinum pyranoside; The lucky pyrans of Glaucogenin A (Cynanchum glaucescens aglycon A)-3-O-(1 → 4)-β-D-glucopyanosyl base-(1 → 4)-α-L-Apocynum cannabinum pyrans glycosyl-(1 → 4)-β-D-enlightening glycosyl-(1 → 4)-β-L-Apocynum cannabinum pyranoside; The lucky pyrans of Glaucogenin C (glaucogenin C)-3-O-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Folium seu Cortex Nerii pyranoside; The lucky pyrans of Glaucogenin A (Cynanchum glaucescens aglycon A)-3-O-(1 → 4)-β-D-glucopyanosyl base-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Apocynum cannabinum pyranoside.
Physiologically active
The present invention has carried out the evaluation experimental of anti-inflammatory activity to radix cynanchi atrati total saponins and 9 compounds.
(1) mice ear model
1 laboratory animal
Swiss kind mouse, male, body weight 20-24g.
2. experimental model and testing method
Get 320 of mouse, be divided into 32 groups at random, press the dosage gastric infusion 3d shown in the table 3,1h after the last administration, dimethylbenzene with 0.05ml causes inflammation with mouse left side ear, the punch tool that with diameter is 7mm is the overlapping punching of ears, and the disk of laying is gone up weighing at torsion(type)balance (sensitivity be ten thousand/), represents its swelling degree with the weight difference of mouse ear two disks.
3 statistical study:
All experimental result is all represented with mean ± standard error.Respectively organize data and the blank significant difference of organizing with student t-check, P＜0.05, expression difference has the significance meaning.
4 test-results:
Table 1. scheelite total saponin(e and saponin compound are to the influence of mice ear test
Group Dosage (mg/kg) n Ear swelling (mg) Inhibiting rate (%)
Blank - 10 18.59±1.38 -
Hydrocortisone 20 10 10.71±1.11 * 42.4
Cynanversicoside A 10 10 13.49±1.96 27.4
20 40 10 10 13.24±0.80 * 10.11±2.21 ** 28.7 45.6
Cynanversicoside B 10 20 40 10 10 10 16.15±5.10 12.22±1.05 * 13.25±5.76 * 13.1 34.3 28.7
Cynaversicoside C 10 20 40 10 10 10 13.21±1.96 * 10.01±0.81 ** 3.15±2.22 *** 28.9 46.2 69.4
Cynaversicoside D 10 20 40 10 10 10 12.15±4.00 * 10.00±1.04 ** 9.90±0.98 ** 34.6 46.2 46.7
Glaucogenin C-3-O-β-D-Semen Thevetiae glucosides 10 20 40 10 10 10 10.49±1.09 ** 10.00±0.53 ** 2.17±0.21 *** 43.6 46.2 88.3
Glaucoside C 10 20 40 10 10 10 13.15±1.10 * 12.22±1.05 * 10.25±1.12 ** 29.3 34.3 44.9
Glaucoside H 10 20 40 10 10 10 13.50±1.06 13.49±0.80 10.01±1.21 ** 27.4 27.4 46.2
Atratoglaucosides A 10 20 40 10 10 10 16.15±5.10 10.21±1.05 ** 10.25±0.71 ** 13.1 45.1 44.9
Cynanosides I 10 20 40 10 10 10 10.49±1.91 ** 10.14±0.74 ** 2.17±0.23 *** 43.6 45.7 88.3
The scheelite total saponin(e 20 50 100 10 10 10 10.79±0.70 * 10.02±1.75 ** 3.26±0.46 *** 42.0 46.2 82.5
Compare with the blank group, *P＜0.05, *P＜0.01, * *P＜0.001
The result shows, positive control drug hydrocortisone, 9 radix cynanchi atrati saponin(es and scheelite total saponin(e have significant inhibitory effect to the inflammation that the mice ear model causes, wherein the action effect of Cynaversicoside C, glaucogenin C-3-O-β-D-Semen Thevetiae glucosides, Cynanosides I and scheelite total saponin(e is stronger.
(2) rat carrageenan foot swelling model
1 laboratory animal
The SD rat, male and female dual-purpose, body weight 180-220g.
2. experimental model and testing method
Get 320 of rats, be divided into 32 groups at random, press the dosage gastric infusion 4d shown in the table 4, before the last administration, measure and cause scorching preceding volume; 30min after the last administration, the sufficient subcutaneous injection 1% carrageenin 0.1ml that wastes time causes inflammation in rat right hind leg.Respectively at cause scorching back 2,4,6h measures the following volume of right ankle joint.
3 statistical study:
All experimental result is all represented with mean ± standard error.Respectively organize data and the blank significant difference of organizing with student t-check, P＜0.05, expression difference has the significance meaning.
4 test-results:
Table 2. scheelite total saponin(e and saponin compound are to the influence of rat carrageenan foot swelling test
Group Dosage (mg/kg) n Paw swelling (ml)
2h 4h 6h
Blank - 10 1.22±0.08 1.01±0.12 0.94±0.16
Dexamethasone 300 10 0.30±0.12 ** 0.36±0.10 ** 0.26±0.09 **
Cynanversicoside A 10 20 40 10 10 10 1.22±0.11 1.07±0.62 * 0.76±0.6 ** 0.91±0.12 0.84±0.26 * 0.30±0.60 ** 0.99±0.24 0.84±0.37 0.50±0.16 *
Cynanversicoside B 10 20 40 10 10 10 1.32±0.12 1.08±0.10 * 0.81±0.08 ** 1.21±0.31 1.07±0.64 0.86±0.60 * 1.01±0.21 1.01±0.34 0.86±0.60
Cynaversicoside C 10 20 40 10 10 10 1.08±0.12 * 1.06±0.09 * 0.52±0.21 ** 0.92±0.21 0.83±0.65 * 0.29±0.56 ** 0.82±0.20 0.53±0.44 * 0.25±0.26 **
Cynaversicoside D 10 20 40 10 10 10 1.05±0.11 * 1.06±0.19 * 0.42±0.07 ** 1.11±0.21 0.84±0.42 * 0.31±0.44 ** 0.97±0.23 0.54±0.24 * 0.56±0.23 *
Glaucogenin C-3-O-β-D-Semen Thevetiae glucosides 10 20 40 10 10 10 1.04±0.21 * 1.04±0.19 * 0.32±0.12 ** 0.79±0.91 * 0.35±0.63 ** 0.10±0.06 *** 0.79±0.91 0.32±0.61 ** 0.09±0.11 ***
Glaucoside C 10 20 40 10 10 10 1.20±0.10 1.06±0.29 * 0.82±0.11 ** 1.42±0.51 1.07±0.52 0.84±0.43 * 1.12±0.47 0.96±0.33 0.52±0.13 *
Glaucoside H 10 20 40 10 10 10 1.32±0.21 * 1.19±0.17 1.05±0.17 * 1.22±0.11 1.07±0.62 * 0.76±0.60 ** 1.24±0.25 0.98±0.26 0.76±0.27
Atratoglaucoside A 10 20 40 10 10 10 1.05±0.13 * 1.04±0.09 * 0.53±0.07 ** 1.22±0.11 1.07±0.62 0.76±0.56 ** 0.92±0.14 1.07±0.62 0.33±0.63 **
Cynanosides I 10 20 40 10 10 10 1.04±0.08 * 0.50±0.17 ** 0.32±0.07 ** 0.83±0.44 * 0.77±0.35 * 0.36±0.17 ** 0.81±0.47 0.53±0.20 * 0.32±0.17 **
The scheelite total saponin(e 20 50 100 10 10 10 1.07±0.11 * 0.61±0.11 ** 0.40±0.17 ** 1.02±0.15 0.87±0.42 * 0.35±0.13 ** 0.99±0.35 0.60±0.44 * 0.29±0.23 **
Compare with the blank group, *P＜0.05, *P＜0.01, * *P＜0.001
The result shows, positive control drug dexamethasone, 9 radix cynanchi atrati saponin(es and scheelite total saponin(e have significant inhibitory effect to the caused inflammation of rat carrageenan foot swelling model, and the action effect of glaucogenin C-3-O-β-D-Semen Thevetiae glucosides is stronger.
(3) mouse peritoneal capillary permeability test
1 laboratory animal
NH is a mouse, male and female dual-purpose, body weight 18-22g.
2. experimental model and testing method
Get 320 of rats, be divided into 32 groups at random, press the dosage gastric infusion 1h shown in the table 5, tail vein injection 2% AZO-blue normal saline solution 0.1ml/10g body weight, abdominal injection 0.8% acetic acid normal saline solution 0.20ml/ only takes off cervical vertebra and puts to death mouse behind the 20min immediately, divides with 5ml physiological saline and washs the abdominal cavity for several times, 3000 rev/mins, centrifugal 15min; Getting supernatant liquor uses microplate reader in its optical density(OD) of 570nm colorimetric estimation (OD) value.
3 statistical study:
All experimental result is all represented with mean ± standard error.Respectively organize data and the blank significant difference of organizing with student t-check, P＜0.05, expression difference has the significance meaning.
4 test-results:
Table 3. scheelite total saponin(e and saponin compound are to the influence of mouse peritoneal capillary permeability test
Group Dosage (mg/kg) n Abdominal cavity capillary penetration liquid OD value (λ=570nm)
Blank - 10 0.77±0.33
Dexamethasone 1.5 10 0.37±0.22 *
Cynanversicoside A 10 20 40 10 10 10 0.55±0.18 0.66±0.36 0.44±0.29 *
Cynanversicoside B 10 20 40 10 10 10 0.66±0.24 0.47±0.11 * 0.41±0.27 *
Cynaversicoside C 10 20 40 10 10 10 0.75±0.13 0.45±0.21 * 0.37±0.12 *
Cynaversicoside D 10 20 40 10 10 10 0.65±0.09 0.43±0.12 * 0.41±0.28 *
Glaucogenin C-3-O-β-D-Semen Thevetiae glucosides 10 20 40 10 10 10 0.69±0.09 0.37±0.20 * 0.33±0.02 *
Glaucoside C 10 20 40 10 10 10 0.65±0.14 0.46±0.20 * 0.43±0.10 *
Glaucoside H 10 20 10 10 0.78±0.11 0.66±0.22
40 10 0.42±0.12 *
Atratoglaucosides A 10 20 40 10 10 10 0.66±0.17 0.47±0.25 * 0.41±0.18 *
Cynanosides I 10 20 40 10 10 10 0.65±0.13 0.37±0.15 * 0.31±0.12 *
The scheelite total saponin(e 20 50 100 10 10 10 0.65±0.23 0.40±0.19 * 0.36±0.17 *
Compare with the blank group, *P＜0.05, *P＜0.01, * *P＜0.001
The result shows, positive control drug dexamethasone, 9 radix cynanchi atrati saponin(es and the scheelite total saponin(e inflammation that test causes to the mouse peritoneal capillary permeability have significant inhibitory effect.
Embodiment
Embodiment 1:
Preparation scheelite total saponin(e
After radix cynanchi atrati dry root 10kg pulverizes, with 10 times of amount 90% alcohol refluxs 3 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, with macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, till being eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part, i.e. scheelite total saponin(e sample.Wherein, radix cynanchi atrati saponin compound content is more than 60%.
The scheelite total saponin(e, pale brown toner end, Lieberman-Burchard and Keller-Killiani reaction all are positive, and show to be all the steroidal compounds that contains the 2-desoxy sugar.
Embodiment 2:
Preparation Cynanchum versicolor Bunge A
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out the purification on normal-phase silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with its A V flow point that is through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying get Cynanversicoside A.
Cynanversicoside A (cynanversicoside A), white amorphous powder, mp120-124 ℃, [α] D 28:-59.28 ° (c=0.521, MeOH), molecular formula: C 42H 64O 15Through spectroscopic data analysis and physicochemical character measure with bibliographical information (QiuSheng-Xiang, et al.Plata.Med., 1991,57, Cynanversicoside A 454.-456) is in full accord.
Embodiment 3:
The preparation Cynanversicoside B
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol alcohol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein A IV flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain Cynanversicoside B.
Cynanversicoside B (cynavesicoside B), white amorphous powder, mp160-164 ℃, [α] D 28:-60.98 ° (c=0.50, MeOH), molecular formula: C 48H 72O 20Through spectroscopic data analysis and physicochemical character measure with bibliographical information (QiuSheng-Xiang, et al.Plata.Med., 1991,57, Cynanversicoside B 454.-456) is in full accord.
Embodiment 4:
The preparation Cynaversicoside C
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein B IV flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain Cynaversicoside C.
Cynaversicoside C (cynanversicoside C), white amorphous powder, mp124-128 ℃, [α] D 28:+49.8 ° (c=0.562, MeOH), molecular formula: C 28H 40O 14Through spectroscopic data analysis and physicochemical character measure with bibliographical information (QiuSheng-Xiang, et al.Phytochemistry, 1989,28 (11), Cynaversicoside C 3175-3178) is in full accord.
Embodiment 5:
The preparation Cynaversicoside D
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein B III flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain Cynaversicoside D.
Cynaversicoside D (cynanversicoside D), white amorphous powder, mp:150-152 ℃, [α] D 28:-8.7 ° (c=0.52, EtOH), molecular formula: C 42H 64O 16Through spectroscopic data analysis and physicochemical character measure with bibliographical information (QiuSheng-Xiang, et al.Phytochemistry, 1989,28 (11), Cynaversicoside D 3175-3178) is in full accord.
Embodiment 6:
Preparation glaucogenin C-3-O-β-D-Semen Thevetiae glucosides
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein B II flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain glaucogenin C-3-O-β-D-Semen Thevetiae glucosides.
Glaucogenin C-β-D-Semen Thevetiae glucosides (glaucogenin C-β-D-thevetopyranoside), white amorphous powder, mp:187-190 ℃, [α] D 28:+27.4 ° of (c=1.03, CHCl 3), molecular formula: C 28H 40O 9Through spectroscopic data analysis and physicochemical character measure with bibliographical information (Takashi Nakagawa, et al.Chem.Pharm.Bull., 1983,31, glaucogenin C 870-877)-3-O-β-D-Semen Thevetiae glucosides is in full accord.
Embodiment 7:
The preparation glaucoside C
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein A I flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain glaucoside C.
Glaucoside C (glaucoside C), white amorphous powder, mp:127-133 ℃, [α] D 28:-14.6 ° of (c=0.91, CHCl 3), molecular formula: C 41H 62O 15Through spectroscopic data analysis and physicochemical character measure with bibliographical information (Takashi Nakagawa, et al.Tetrahedron, 1983,39 (4), glaucoside C 607-612) is in full accord.
Embodiment 8:
The preparation Glaucoside H
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein A II flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain Glaucoside H.
Glaucoside H (glaucoside H), white amorphous powder, mp:150-154 ℃, [α] D 28:-29.6 ° of (c=0.98, CHCl 3), molecular formula: C 47H 72O 20Through spectroscopic data analysis and physicochemical character measure with bibliographical information (Zhang Zhuang-Xin, et al.Chem.Pharm.Bull.1985,33 (10), Glaucoside H 4188-4192) is in full accord.
Embodiment 9:
Preparation Atratoglaucosides A
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein A III flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain Atratoglaucosides A.
Atratoglaucosides A, white amorphous powder, mp:120-127 ℃, [α] D:-21 ° of (c=0.16, CHCl 3), molecular formula: C 35H 52O 12Through spectroscopic data analysis and physicochemical character measure with bibliographical information (Day Shiow-Hwa, et al.J.Nal.Prod.2001,64, Atratoglaucosides A 608-611) is in full accord.
Embodiment 10:
Preparation Cynanosides I
After radix cynanchi atrati dry root 10kg pulverizes, measure 90% alcohol refluxs 3 times with 10 times, each 2 hours, united extraction liquid, decompression and solvent recovery, get ethanol extraction, macroporous resin HP-20 post on this extract, it is colourless to be eluted to elutriant with distilled water and 30%EtOH respectively, be eluted to sulfuric acid ethanol saponin(e colour developing feminine gender with 90%EtOH again till, reclaim the 90%EtOH elutriant to doing, get 90%EtOH wash-out part.The 90%EtOH wash-out is partly carried out silica gel column chromatography, carry out gradient elution with chloroform-methanol, check the chromatography flow point with thin-layer chromatography, flow point with identical single spot merges, and concentrates, and gets flow point 1,2,3,4,5,3 and 4 parts are wherein carried out the purification on normal-phase silica gel column chromatography more respectively, chloroform-methanol in varing proportions carries out wash-out, flow point 3 A I-VII flow point, flow point 4 B I-V flow point, with wherein B I flow point through repeatedly RP-C18 chromatography (MeOH:H 2O) separation, purifying obtain Cynanosides I.
Cynanosides I, white amorphous powder, [α] D:-10.5 ° of (c=1.10, CHCl 3), molecular formula: C 48H 74O 20Through spectroscopic data analysis and physicochemical character measure with bibliographical information (Bai Hong, et al.Tetrahedron.2005,61, Cynanoside I 5797-5811) is in full accord.
Embodiment 11:
Get the scheelite total saponin(e 100g among the embodiment 1, disperse, add right amount of auxiliary materials, mixing with an amount of water for injection, make particle, drying is pressed into 1000, every 0.1g, sugar coating promptly get scheelite total saponin(e sheet, and other project should meet under Pharmacopoeia of People's Republic of China version tablet in 2005 item.This tablet is used for prevention and treatment chronic inflammatory diseases such as chronic pharyngolaryngitis, chronic enterogastritis etc., has good effect.
Embodiment 12:
Get scheelite total saponin(e 100g, make 5% scheelite total saponin(e solution with 75% dissolve with ethanol, use activated carbon decolorizing, filter the concentrating under reduced pressure drying, add the injection water and make the aqueous solution that every ml contains 20mg scheelite total saponin(e, filter to clear and bright, aseptic subpackaged in the control antibiotic glass bottle every bottle of 5ml with millipore filtration (φ 0.20 μ m), put lyophilize in the freeze drier, promptly.This powder injection is used for the treatment of acute inflammation such as acute tonsillitis, upper respiratory tract infection, acute gastroenteritis etc., has good result.
Embodiment 13:
Get scheelite total saponin(e 1kg, 0.5 ton of medical starch, with 80% ethanol wet granulation, whole grain, dress 2# capsule, every 0.2g.Other project should meet under Pharmacopoeia of People's Republic of China version capsule in 2005 item.This capsule is used for the treatment of acute or chronic inflammation such as pneumonia, trachitis, phlebitis etc., has positive effect.
Embodiment 14:
Get Cynanversicoside A 9g, add propylene glycol and each 20ml of ethanol, stir and make dissolving, add injection and be diluted with water to 10000ml, cross the millipore filtration of 0.22 μ m, embedding, 10ml/ bottle, flowing steam sterilization in 30 minutes, check, packing, get the Cynanversicoside A injection liquid, be used for the treatment of acute inflammation such as acute tonsillitis, upper respiratory tract infection, acute gastroenteritis, phlebitis etc., have positive effect.
Embodiment 15:
Get Cynaversicoside D 32g, cross 100 mesh sieves; Get beeswax 4.2g, add soybean oil 125g, fusion mixing under 80 ℃ of water-baths is cooled to room temperature (25 ℃).Add butyl hydroxy anisol, Citric Acid, fully mixing.Add Cynaversicoside D, Yelkin TTS 5g adds soybean oil to 250g, and fully mixing as capsule heart liquid, is pressed into 1000 soft capsules, is used for the treatment of upper respiratory tract infection, tonsillitis, has good result.
Embodiment 16:
Precision takes by weighing the Glaucoside H 20g of recipe quantity and lactose 40g, Microcrystalline Cellulose 70g, polyvinylpolypyrrolidone (5.25g), aspartame 2.5g, polyvidone 6.0g, sodium bicarbonate 4.0g, progressively increases method with the main ingredient Glaucoside H and various auxiliary material is manual earlier mixes by equivalent.Cross twice of 80 mesh sieve.Material behind the mixing is put in the appropriate containers, and it is an amount of to add 75% ethanolic soln contain 15% (g/100ml) polyethylene glycol 6000, the system softwood.20 orders pushed the sieve series wet granular.Wet granular is divided in enamel tray, puts in the air blast thermostatic drying chamber 70 ℃ of dryings 2 hours.The weight of accurate weighing dried particles, the residue polyvinylpolypyrrolidone of adding 2.25g, the amount by 1% adds sodium lauryl sulphate (SDS), and behind the mixing, the circular punch die of 7mm is pressed into 1000.Promptly get 1000 of Glaucoside H dispersible tablets.Be used for the treatment of chronic intestinal inflammations, have good result.
Embodiment 17:
24.02g polyethylene glycol 6000,6.00g poloxamer 188 are put in the beaker, heating makes fusion in 95 ℃ of water-baths, stir, add 6.40g Cynanosides I, stir, add the 10ml anhydrous alcohol for medical use, fully stir, make Cynanosides I dissolving, continue to stir, make the ethanol volatilization, heat preservation for standby use.The preheating of DW-1 type dripping pill machine, making fluid storage compartment temperature constant temperature is 95 ± 2 ℃, refrigerant is chilled to 10～12 ℃ in advance, regulate water dropper (internal diameter is 2.5mm) and be about 11～13cm with the distance of cooling off liquid level, pour soup into fluid storage compartment, start and drip the system valve, soup is dropwise splashed in the refrigerant, regulate a speed and be about 30 droplets/minute.In collecting a mouthful collection dripping pill, absorb the surface cool agent with gauze, freezer compartment of refrigerator (18 ℃) freezing treatment 24 hours is put in the vacuum drying oven, and normal temperature vacuum-drying 24 hours promptly gets Cynanosides I dripping pill.Be used for the treatment of pneumonia, upper respiratory tract infection etc., have good result.

Claims (7)

1, a kind of scheelite total saponin(e and saponins compound, it is characterized in that from the radix cynanchi atrati medicinal material, separating and obtain, the radix cynanchi atrati saponins compound is 9 kinds of carbon-21 steroidal saponin(es, be respectively: Cynanversicoside A, Cynanversicoside B, Cynaversicoside C, Cynaversicoside D, glaucogenin C-3-O-β-D-Semen Thevetiae glucosides, glaucoside C, Glaucoside H, Atratoglaucosides A and Cynanosides I, scheelite total saponin(e are the mixture of weight content 〉=50% that comprises carbon-21 steroidal saponin(e and saponins compound; These 9 kinds of carbon-21 steroidal saponin(es are 9 kinds of glucosides that one of them and different quantities of 3 kinds of steroid sapogenins shown in following 3 chemical structures, dissimilar sugar form, and wherein R is a sugar chain:
Figure A2006100247500002C1
Glaucogenin A Glaucogenin C Glaucogenin D
2, scheelite total saponin(e according to claim 1 and saponins compound is characterized in that in described 9 kinds of carbon-21 steroidal saponin(es:
Among the Cynanchum versicolor Bunge A, aglycon is Glaucogenin C, and R is the lucky pyrans of β-D-Apocynum cannabinum pyranose-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyrans glycosyl;
Among the Cynanchum versicolor Bunge B, aglycon is Glaucogenin C, and R is the lucky pyrans of β-D-glucopyanosyl base-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyrans glycosyl;
Among the Cynanchum versicolor Bunge C, aglycon is Glaucogenin D, and R is β-D-Folium seu Cortex Nerii pyrans glycosyl;
Among the Cynanchum versicolor Bunge D, aglycon is Glaucogenin D, and R is the lucky pyrans of β-D-Apocynum cannabinum pyranose-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyrans glycosyl;
In glaucogenin C-3-O-β-D-Semen Thevetiae glucosides, aglycon is Glaucogenin C, and R is β-D-Semen Thevetiae pyrans glycosyl;
In the glaucoside C, aglycon is Glaucogenin A, and R is the lucky pyrans of α-L-Apocynum cannabinum pyrans glycosyl-(1 → 4)-β-D-enlightening glycosyl-(1 → 4)-β-L-Apocynum cannabinum pyrans glycosyl;
In the Glaucoside H, aglycon is Glaucogenin A, and R is the lucky pyrans of β-D-glucopyanosyl base-(1 → 4)-α-L-Apocynum cannabinum pyrans glycosyl-(1 → 4)-β-D-enlightening glycosyl-(1 → 4)-β-L-Apocynum cannabinum pyrans glycosyl;
Among the atratoglaucosides A, aglycon is Glaucogenin C, and R is the lucky pyrans of α-L-enlightening glycosyl-(1 → 4)-β-D-Semen Thevetiae pyrans glycosyl;
Among the Cynanosides I, aglycon is Glaucogenin A, and R is the lucky pyrans of β-D-glucopyanosyl base-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl-(1 → 4)-α-L-enlightening glycosyl-(1 → 4)-β-D-Apocynum cannabinum pyrans glycosyl.
3, scheelite total saponin(e according to claim 1 and saponins compound is characterized in that described scheelite total saponin(e is the mixture that includes a kind of or its any several combinations in Cynanversicoside A, Cynanversicoside B, Cynaversicoside C, Cynaversicoside D, glaucogenin C-3-O-β-D-Semen Thevetiae glucosides, glaucoside C, Glaucoside H, these 9 kinds of carbon-21 steroidal saponin(es of atratoglaucosides A, cynanosides I.
4, as the application in preparation prevention and treatment acute or chronic inflammation and relative disease medicine according to claim 1 scheelite total saponin(e and saponins compound.
5, application according to claim 4 is characterized in that acute or chronic inflammation comprises: upper respiratory tract infection, tonsillitis, pharyngolaryngitis, gastro-enteritis, pneumonia, trachitis and phlebitis.
6, as scheelite total saponin(e according to claim 1 and saponins compound, the pharmaceutical composition of forming with pharmaceutically acceptable carrier of its prevention and treatment acute or chronic inflammation and relative disease significant quantity.
7, pharmaceutical composition according to claim 6 is characterized in that formulation has tablet, granule, capsule, oral liquid, dripping pill, mixture, syrup, tincture or injection.
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101693036B (en) * 2009-10-21 2011-11-09 中国人民解放军第二军医大学 Application of cynanversicoside C in preparation of medicines for treating malaria
CN102329358A (en) * 2011-05-31 2012-01-25 苏州派腾生物医药科技有限公司 Preparation method of cynatratoside A
CN101549000B (en) * 2008-04-02 2012-07-04 天津天士力制药股份有限公司 Effective component of cynanchum atratum and preparation method thereof
CN110946888A (en) * 2019-12-26 2020-04-03 北京农学院 Application of cynanchum atratum in preparation of medicine for protecting intestinal inflammation of animals
CN111012813A (en) * 2019-12-26 2020-04-17 北京农学院 Application of cynanchum atratum in preparation of medicine for protecting intestinal tract injury of animals
CN111358804A (en) * 2020-04-20 2020-07-03 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) Application of Cynoside H in preparation of medicine for preventing and treating breast cancer

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101549000B (en) * 2008-04-02 2012-07-04 天津天士力制药股份有限公司 Effective component of cynanchum atratum and preparation method thereof
CN101693036B (en) * 2009-10-21 2011-11-09 中国人民解放军第二军医大学 Application of cynanversicoside C in preparation of medicines for treating malaria
CN102329358A (en) * 2011-05-31 2012-01-25 苏州派腾生物医药科技有限公司 Preparation method of cynatratoside A
CN110946888A (en) * 2019-12-26 2020-04-03 北京农学院 Application of cynanchum atratum in preparation of medicine for protecting intestinal inflammation of animals
CN111012813A (en) * 2019-12-26 2020-04-17 北京农学院 Application of cynanchum atratum in preparation of medicine for protecting intestinal tract injury of animals
CN111358804A (en) * 2020-04-20 2020-07-03 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) Application of Cynoside H in preparation of medicine for preventing and treating breast cancer

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