CN101590134A - Has total triterpene of garden burnet root of anti-inflammatory and analgesic effect and preparation method thereof - Google Patents
Has total triterpene of garden burnet root of anti-inflammatory and analgesic effect and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to medical technical field, the preparation method of Chinese medicine total triterpene of garden burnet root is provided, mainly is by 70% alcohol reflux, absorption with macroporous adsorbent resin washes decontamination with water, with pure liquid eluting, eluent is again through Silon decolouring, with pure liquid eluting, and decompression recycling ethanol and obtaining.This total triterpene mainly contain arjunic acid, 1 β-euscaphic acid Jacaric acid, euscaphic acid Jacaric acid, tormentic acid, etc. the triterpenic acid active component, and Ziyuglycoside I, Ziyuglycoside I I, Ziyuglycoside I II, niga-ichigoside, kaji-ichigoside F
1Deng the triterpene saponin active component.Experimental result shows that its antiinflammatory and analgesic effect are remarkable.This total triterpene working substance basis and the mechanism of action are clear and definite, preparation technology is simple, be fit to suitability for industrialized production, can be used as the medicine material of inflammatory diseasess such as treatment burn and scald, proctitis, ulcerative colitis, pyelonephritis, technology is made acceptable forms clinically such as tablet, capsule, granule or compound preparation routinely.
Description
Technical field
The present invention relates to medical technical field, relate to the preparation method of total triterpene of garden burnet root, the invention still further relates to the medical usage of inflammatory diseasess such as total triterpene of garden burnet root treatment proctitis, ulcerative colitis, pyelonephritis, burn and scald.
Background technology
Radix Sanguisorbae Sanguisorba officinalis L. has cooling blood for hemostasis, and the effect of skin ulcer is held back in detoxifcation, is widely used determined curative effect.Be widely used in inflammatory diseasess such as proctitis, ulcerative colitis, pyelonephritis, burn and scald clinically, and the treatment of Medicine and Surgery hemostatic.The Chemical Constituents in the Radix Sanguisorbae root is shown: be rich in triterpenic acid and triterpene saponin componds in the Radix Sanguisorbae, and based on ursane type and oleanane type triterpene.
Water, alcohol extract that bibliographical information is in the past crossed Radix Sanguisorbae have very strong antiinflammatory action.Lumbar injection Radix Sanguisorbae water extract 400mg/kg or alcohol extract 650mg/kg can effectively suppress rat formaldehyde pedal swelling, and onset are very fast; Lumbar injection water extract 750mg/kg or alcohol extract 800mg/kg have remarkable inhibitory action to rat granuloma is swollen, and suppression ratio is more than 70%; Lumbar injection water extract 500mg/kg is suitable to the suppression ratio and the hydrocortisone of Oleum Tiglii mice ear, and 800mg/kg then can obviously suppress the rat skin microvascular permeability increase that PGE1 causes.In addition, Radix Sanguisorbae can be used for treating burn and scald, prevention and control infection, and eliminate pain, visible Radix Sanguisorbae has certain anti-inflammatory and analgesic effect.
Recently, we are in early stage over the ground on the research basis of the anti-inflammatory and antalgic immunization of elm, and it is strong active to find that the Radix Sanguisorbae ethanol extract shows.Above-mentioned ethanol extract is carried out extraction separation, and select for use the inductive mice ear model of dimethylbenzene, acetic acid twisting test and the hyperfunction test of abdominal cavity capillary permeability that orthogonal design is carried out at several positions and dosage, filtering out the anti-inflammatory and antalgic activity position is total triterpene of garden burnet root (SOTT).With mice caused by dimethylbenzene xylene ear swelling model triterpenic acid and the triterpene saponin constituents of separating carried out anti-inflammatory activity research from total triterpene of garden burnet root, find that arjunic acid, 1 β-euscaphic acid Jacaric acid, Ziyuglycoside I, Ziyuglycoside I I, niga-ichigoside demonstrate certain anti-inflammatory activity (Chinese pharmaceutical chemistry magazine, 2008,18 (2): 138-141).Above-mentioned chemistry and pharmacological research provide scientific basis for its clinical practice.At present, the preparation method of the relevant total triterpene of garden burnet root of Shang Weijian, and the report of in inflammation disease medicines such as treatment proctitis, ulcerative colitis, pyelonephritis, burn and scald, using.
Summary of the invention
The object of the present invention is to provide the preparation method of the extract total triterpene of garden burnet root that contains triterpenes components in the Chinese medicine Radix Sanguisorbae, and clearly proposed the medical usage of inflammatory diseasess such as its treatment proctitis, ulcerative colitis, pyelonephritis, burn and scald.It is stable to the invention provides a kind of science, is applicable to the method for preparing total triterpene of garden burnet root of suitability for industrialized production.
The present invention is achieved through the following technical solutions:
After Radix Sanguisorbae pulverized, through 70% alcohol reflux, absorption with macroporous adsorbent resin washed decontamination with water, and with pure liquid eluting, eluent decolours through Silon, or obtained with ethyl acetate and n-butanol extraction respectively.Its feature comprises following 3 steps:
A, 70% ethanol extraction: the Radix Sanguisorbae coarse powder, add 70% soak with ethanol that 6-9 doubly measures, heating and refluxing extraction, each 1-3 hour, extract 2-4 time, merge each time extracting solution, decompression and solvent recovery to the concentration of the contained crude drug of solution is 30-40g/ml.
B, D101 type macroporous resin adsorption: A step water extracting liquid is through absorption with macroporous adsorbent resin, and with rare alcohol (0-20%) flush away impurity, reuse 70-75% alcohol liquid eluting is collected alcohol eluen, and decompression and solvent recovery obtains total triterpene crude product.
The total triterpene crude product of C, remove impurity and decolouring: B step gained is suspended in the aqueous solution, through polyamide column chromatography, elder generation's water dashes, and uses the abundant eluting of 75% ethanol then, decompression recycling ethanol, or use ethyl acetate and n-butanol extraction respectively, decompression and solvent recovery obtains this total triterpene.
Further, this extract is through silica gel column chromatography, the chloroform-methanol gradient elution, each stream part is again through repeatedly MCI gel column chromatography, Sephadex LH-20 column chromatography and anti-phase ODS column chromatography, water-methanol mixed solvent gradient elution, obtain 8 triterpenic acid active components such as arjunic acid, rosamultic acid, haptadienicacid, 1 β-euscaphic acid Jacaric acid, euscaphic acid Jacaric acid, tormentic acid, pomolic acid 19alpha-Hydroxyursolic acid and ursolic acid, and Ziyuglycoside I, Ziyuglycoside I I, Ziyuglycoside I II, niga-ichigoside, kaji-ichigoside F
1Deng 5 triterpene saponin active components (Chinese pharmaceutical chemistry magazine, 2008,18 (2): 138-141; China's pharmaceutical chemistry magazine, 2009,19 (1): 52-54).The separation of above-claimed cpd and structure are identified the material base of having illustrated total triterpene of garden burnet root.The main triterpene and the general structure of triterpene saponin active component are in total triterpene:
R in the formula
1Be hydrogen or hydroxyl, R
2Be hydrogen or 1 glycosyl, R
3Be hydrogen or 1 glycosyl, R
4Be hydrogen or methyl, R
5Be hydrogen or methyl, R
6Be methyl or methylol, above indication glycosyl is meant glucopyranosyl or arabopyranose base.
The inventor causes the hyperfunction test of mouse peritoneal capillary permeability by the inductive mice ear test of dimethylbenzene, the test of mice acetic acid twisting and acetic acid respectively, has observed the anti-inflammatory and analgesic effect of total triterpene of garden burnet root (SOTT).Experimental result shows, SOTT is when oral dose 100mg/kg, can suppress ear swelling extremely significantly, reduce the mouse writhing number of times, highly significant suppresses the ivens orchid and oozes out to the abdominal cavity from capillary tube, with the no significant difference of positive drug indomethacin (oral dose 10mg/kg), illustrate that total triterpene of garden burnet root has obvious anti-inflammatory analgesic.
Extract of the present invention have working substance basis and the mechanism of action clear and definite, preparation technology is simple, the characteristics that are fit to suitability for industrialized production, can be used as the raw material of inflammatory diseasess such as treatment burn and scald, proctitis, ulcerative colitis, pyelonephritis, technology is made acceptable forms clinically such as tablet, capsule, granule or compound preparation routinely.
The specific embodiment
Below further specify the present invention by specific embodiment, embodiment only be used for the explanation, can not limit the scope of the invention.
Embodiment 1
Get Radix Sanguisorbae coarse powder 5kg, add 35L 70% soak with ethanol and spend the night, heating and refluxing extraction 2 times, extraction time was respectively 2,2 hours, merged alcohol extract, filter, 60 ℃ be evaporated to the concentration of the contained crude drug of solution be 30g/ml, filter; Filtrate is through D101 type absorption with macroporous adsorbent resin, resin demand 6kg, difference water and 20% ethanol flush away impurity, reuse 75% ethanol liquid eluting, collect alcohol eluen, decompression and solvent recovery, the gained crude product is suspended in the aqueous solution, again through polyamide column chromatography, elder generation's water dashes, use the abundant eluting of 75% ethanol then, decompression recycling ethanol obtains this total triterpene 340g.
Embodiment 2
Get Radix Sanguisorbae coarse powder 5kg, add 45L 70% soak with ethanol and spend the night, heating and refluxing extraction 3 times, extraction time was respectively 2,2,1 hours, merge extractive liquid, filters, 60 ℃ be evaporated to the concentration of the contained crude drug of solution be 40g/ml, filter; Filtrate is through the D101 absorption with macroporous adsorbent resin, resin demand 6kg, difference water and 20% ethanol flush away impurity, reuse 70% ethanol liquid eluting, collect alcohol eluen, decompression and solvent recovery, the gained crude product is suspended in the aqueous solution, uses the ethyl acetate and the n-butanol extraction of equivalent more respectively, each extracts 4 times, decompression and solvent recovery merges extract, obtains this total triterpene 310g.
The inhibitory action of the inductive mice ear of embodiment 3 total triterpene of garden burnet root xylol
(1) experiment material
Animal: (25 ± 2g), fasting is 24 hours before the administration, freely drinks water for the male KM mice.
Reagent: normal saline, dimethylbenzene, 0.5%CMCNa, aspirin (aspirin) (pharmaceutcal corporation, Ltd is melted in Shenyang ten thousand, batch number: 061205), and indomethacin (indomethacin) (Shanxi Yun Peng pharmaceutical Co. Ltd, batch number: A070801).
Material and instrument: 1ml mouse stomach device, 1ml syringe, operating scissors, tweezers, card punch, volumetric flask, electronic balance (CPJ603 Ohaus Instrument (Shanghai) Co., Ltd.).
(2) experimental technique
Mice is divided into 5 groups at random, 10 every group: and negative control group (0.2%CMCNa, 10ml/kg, i.g.), aspirin matched group (30mg/kg
-1, i.g), indomethacin matched group (10mg/kg
-1, i.g.), and the medicine group (100,30mg/kg, i.g.).After the administration 30 minutes, draw 30 μ L dimethylbenzene with microsyringe and be applied to each Mus auris dextra part and cause inflammation, each 15 μ L of two sides, front and back; Left side ear is made normal control.Behind the 2h, mice is put to death in the cervical vertebra dislocation, cuts ears, sweeps away two ears with the position disk with 7mm diameter card punch, and analytical balance is weighed.
The difference of left and right sides auricle weight is a Mus ear swelling degree.Get swelling degree mean value calculation suppression ratio, suppression ratio calculates:
Suppression ratio I (%)=(E
0-E
1)/E
0* 100%
E wherein
0And E
1Represent the average ear swelling degree of negative control group and administration group respectively.
(3) experimental result
Total triterpene of garden burnet root (by mice body weight 100,30mg/kg, i.g.), aspirin matched group (30mg/kg
-1, i.g.), and indomethacin matched group (10mg/kg
-1, ear swelling suppression ratio i.g.) is respectively 31.6%, 23.6%, and 22.6% and 32.4%, demonstrate the antiinflammatory action similar with indomethacin to the positive drug aspirin.The results are shown in Table 1.
The inhibitory action of the inductive mice ear of table 1 total triterpene of garden burnet root xylol [x ± S.E.M. (n=10)]
* compare p＜0.01 with the blank group
Embodiment 4 total triterpene of garden burnet root Dichlorodiphenyl Acetates cause mouse writhing number of times and the hyperfunction influence of abdominal cavity capillary permeability
(1) test material
Animal: (25 ± 2g), fasting is 24 hours before the administration, freely drinks water for the male KM mice.
Reagent: normal saline, 0.6% aqueous acetic acid, distilled water, 50u/ml heparin-saline (the 1ml heparin adds normal saline to 250ml), the blue normal saline solution of 0.5% ivens, indomethacin (Shanxi Yun Peng pharmaceutical Co. Ltd, batch number: A070801).
Material and instrument: irrigation stomach device, operating scissors, syringe, tweezers, screen cloth, centrifuge tube (5ml), electronic balance (CPJ603 Ohaus Instrument (Shanghai) Co., Ltd.), 721E type visible spectrophotometer (Shanghai Spectrum Apparatus Co., Ltd.).
(2) experimental technique
Mice is divided into 3 groups at random, 8 every group: blank group (group 1, distilled water, 20mL kg
-1, i.g.), positive controls (group 2, indomethacin, 10mg kg
-1, i.g.), administration group (group 3, SOTT, 100mg kg
-1, i.g.).Each organizes the blue normal saline solution of tail vein injection 0.5% ivens, and the administration volume is the 0.1ml/10g body weight, irritates stomach after 1 hour respectively and gives distilled water, indomethacin and total triterpene of garden burnet root (SOTT), and the administration volume is the 0.2ml/10g body weight; After the administration 30 minutes, lumbar injection 0.6% aqueous acetic acid 0.2ml/ only, observe the mouse writhing number of times in 20 minutes, take off neck after 20 minutes immediately and put to death, 6ml washes out peritoneal fluid with heparin-saline, adds heparin-saline to 10ml, with 3000rpm centrifugal 15 minutes, get supernatant in 721 type spectrophotometer 590nm place colorimetrics, measure absorbance, represent the blue seepage discharge of ivens with absorbance.
(3) experimental result
Total triterpene of garden burnet root (SOTT) can extremely significantly reduce the mouse writhing number of times when oral dose 100mg/kg, highly significant suppresses the ivens orchid and oozes out to the abdominal cavity from capillary tube; The suppression ratio and the positive drug of mouse writhing number of times and peritoneal fluid absorbance do not have significant difference, illustrate that total triterpene of garden burnet root has obvious anti-inflammatory analgesic.The results are shown in Table 2 and 3.
Table 2 total triterpene of garden burnet root Dichlorodiphenyl Acetate causes the minimizing effect [x ± S.E.M. (n=8)] of mouse writhing number of times
* compare P＜0.001 with the blank group
Table 3 total triterpene of garden burnet root Dichlorodiphenyl Acetate causes the hyperfunction inhibitory action of mouse peritoneal capillary permeability [x ± S.E.M. (n=8)]
* compare P＜0.05 with the blank group, * * compares P＜0.01 with blank group.
Claims (6)
1, have the total triterpene of garden burnet root of anti-inflammatory and analgesic effect, it is characterized in that: this total triterpene extracts from the Chinese medicine Radix Sanguisorbae, separates and refining obtaining, and the main triterpene and the general structure of triterpene saponin active component are in total triterpene:
R in the formula
1Be hydrogen or hydroxyl, R
2Be hydrogen or 1 glycosyl, R
3Be hydrogen or 1 glycosyl, R
4Be hydrogen or methyl, R
5Be hydrogen or methyl, R
6Be methyl or methylol, above indication glycosyl is meant glucopyranosyl or arabopyranose base.
2, the total triterpene of garden burnet root with anti-inflammatory and analgesic effect according to claim 1, it is characterized in that: mainly contain in total triterpene arjunic acid, 1 β-euscaphic acid Jacaric acid, euscaphic acid Jacaric acid, tormentic acid, etc. the triterpenic acid active component, and Ziyuglycoside I, Ziyuglycoside I I, Ziyuglycoside I II, niga-ichigoside, kaji-ichigoside F
1The triterpene saponin active component.
3, the application of total triterpene of garden burnet root in the inflammatory diseases medicine of preparation treatment proctitis, ulcerative colitis, pyelonephritis, burn and scald that has anti-inflammatory and analgesic effect.
4, any one described total triterpene of garden burnet root with anti-inflammatory and analgesic effect of claim 1-3, it is characterized in that: described total triterpene of garden burnet root can be used as active component and pharmaceutically acceptable carrier or mixed with excipients and is prepared into acceptable tablet, capsule, granule or compound preparation clinically.
5, a kind of preparation method with total triterpene of garden burnet root of anti-inflammatory and analgesic effect as claimed in claim 1 comprises pulverizing, through 70% alcohol reflux, absorption with macroporous adsorbent resin, wash decontamination with water,, it is characterized in that: prepare by following method with pure liquid eluting:
Step 1: the Radix Sanguisorbae coarse powder adds 70% soak with ethanol that 7-9 doubly measures, heating and refluxing extraction, and each 1-2 hour, extract 2-3 time, merge each time extracting solution, the concentration that is evaporated to the contained crude drug of solution is 30-40g/ml;
Step 2: step 1 gained solution is through absorption with macroporous adsorbent resin, and with the rare pure flush away impurity of 0-20%, reuse 70-75% alcohol liquid eluting is collected alcohol eluen, and decompression and solvent recovery obtains total triterpene crude product;
Step 3: the total triterpene crude product of step 2 gained, through polyamide column chromatography, first water dashes, and uses the abundant eluting of 75% ethanol then, and decompression recycling ethanol obtains this total triterpene; Or the total triterpene crude product of step 2 gained, use ethyl acetate and n-butanol extraction respectively, decompression and solvent recovery merges extract, obtains this total triterpene.
6, the preparation method with total triterpene of garden burnet root of anti-inflammatory and analgesic effect according to claim 5 is characterized in that: described macroporous adsorbent resin is a D-101 type macroporous adsorbent resin.
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| CN101830964A (en) * | 2010-05-21 | 2010-09-15 | 中国人民解放军第二军医大学 | Triterpenoid compounds with anti-inflammatory activities |
| CN104940458A (en) * | 2015-06-09 | 2015-09-30 | 吉林大学珠海学院 | Analgesic traditional Chinese medicine composition and preparation method thereof |
| CN105418725A (en) * | 2015-11-25 | 2016-03-23 | 广东药学院 | Pentacyclic triterpene compound and application thereof |
| CN105920137A (en) * | 2016-06-02 | 2016-09-07 | 中国药科大学 | Application of sanguisorba total saponin to treatment of inflammatory bowel diseases |
| CN106892956A (en) * | 2015-12-17 | 2017-06-27 | 广州中医药大学 | A kind of Ursane triterpene saponin componds and its preparation method and application |
| CN106892958A (en) * | 2015-12-17 | 2017-06-27 | 广州中医药大学 | A kind of exocyclic double bond Ursane triterpene saponin componds and its preparation method and application |
| CN106892957A (en) * | 2015-12-17 | 2017-06-27 | 广州中医药大学 | A kind of oleanane-type triterpene saponin class compound and its preparation method and application |
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| CN109771394A (en) * | 2019-02-28 | 2019-05-21 | 广东岭南职业技术学院 | A kind of viscid germander herb anti-inflammatory plastics and preparation method thereof |
| CN110818768A (en) * | 2019-11-03 | 2020-02-21 | 福建农林大学 | Novel method and novel raw material for extracting euscaphic acid from plant |
| CN110882315A (en) * | 2019-12-18 | 2020-03-17 | 哈尔滨医科大学 | Sanguisorba officinalis extract for preventing colon cancer and preparation method and application thereof |
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| CN101830964B (en) * | 2010-05-21 | 2012-05-02 | 中国人民解放军第二军医大学 | Triterpenoid compounds with anti-inflammatory activities |
| CN101830964A (en) * | 2010-05-21 | 2010-09-15 | 中国人民解放军第二军医大学 | Triterpenoid compounds with anti-inflammatory activities |
| CN104940458A (en) * | 2015-06-09 | 2015-09-30 | 吉林大学珠海学院 | Analgesic traditional Chinese medicine composition and preparation method thereof |
| CN105418725B (en) * | 2015-11-25 | 2017-12-26 | 广东药科大学 | Pentacyclic triterpenoid and its application |
| CN105418725A (en) * | 2015-11-25 | 2016-03-23 | 广东药学院 | Pentacyclic triterpene compound and application thereof |
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| CN106892957A (en) * | 2015-12-17 | 2017-06-27 | 广州中医药大学 | A kind of oleanane-type triterpene saponin class compound and its preparation method and application |
| CN106892956A (en) * | 2015-12-17 | 2017-06-27 | 广州中医药大学 | A kind of Ursane triterpene saponin componds and its preparation method and application |
| CN106892958A (en) * | 2015-12-17 | 2017-06-27 | 广州中医药大学 | A kind of exocyclic double bond Ursane triterpene saponin componds and its preparation method and application |
| CN106892956B (en) * | 2015-12-17 | 2018-11-16 | 广州中医药大学 | A kind of Ursane triterpene saponin componds and its preparation method and application |
| CN106892957B (en) * | 2015-12-17 | 2018-11-16 | 广州中医药大学 | A kind of oleanane-type triterpene saponin class compound and its preparation method and application |
| CN105920137A (en) * | 2016-06-02 | 2016-09-07 | 中国药科大学 | Application of sanguisorba total saponin to treatment of inflammatory bowel diseases |
| CN108704074A (en) * | 2018-06-27 | 2018-10-26 | 陶燃 | A kind of pharmaceutical composition that treating rhinitis chronic and its application |
| CN109771394A (en) * | 2019-02-28 | 2019-05-21 | 广东岭南职业技术学院 | A kind of viscid germander herb anti-inflammatory plastics and preparation method thereof |
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| CN110882315A (en) * | 2019-12-18 | 2020-03-17 | 哈尔滨医科大学 | Sanguisorba officinalis extract for preventing colon cancer and preparation method and application thereof |
| CN115444855A (en) * | 2022-10-24 | 2022-12-09 | 牡丹江医学院附属红旗医院 | Pharmaceutical composition for treating ulcerative colitis and application thereof |
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