CN101402661A - Uses of iridoid glycoside compounds in preparing hemostatic and pain easing medicament - Google Patents
Uses of iridoid glycoside compounds in preparing hemostatic and pain easing medicament Download PDFInfo
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Abstract
The invention provides the application of iridoid glycosides in the preparation of hemostasis and analgesia medicaments, in particular to the application of the iridoid glycosides, such as 8-O-acetyl shanzhiside methyl ester, 6-O-acetyl shanzhiside methyl ester, Penstemoside, acetyl shanzhiside methyl ester, loganin, Phloyoside II or 8-dehydroxystilbene shanzhiside and the like in the preparation of hemostasis and analgesia medicaments. The iridoid glycosides show good hemostasis, procoagulant and analgesia effect through the influence on bleeding time, capillary coagulation time in mice with tails cut and the influence on twisting times caused by injecting acetic acid in the abdominal cavityies mice. The iridoid glycosides is combined with dressing regularly used in medicine and pharmacology, and then prepared into any oral or parenteral agent by the regular method.
Description
Technical field
The invention belongs to medical technical field, relate to of the application of a kind of iridoid glycoside compounds, relate in particular to the application of iridoid glycoside compounds in preparation hemostasis, analgesic at field of medicaments.
Background technology
Iridoid glycoside is the monoterpenes compound that contains sugared aglucon, and the pentamethylene that contains 10 C in the molecule condenses pyranoid ring basic structure.In recent years, successively from different plants, separate and reported that several thousand kinds of monomer components, this constituents have anticancer, cardiovascular, antiviral and the immunomodulatory isoreactivity, cause increasing concern.Plants such as Root of Common Lamiophlomis are rich in iridoid and glycosides compound thereof, and wherein main type is C
1The position is by the replacement of 1 molecule glucose, C
4Position carboxyl esterization, double bond position are in C
3And C
4Between the iridoid glycoside compounds of cyclopentane type.
With the Tibet medicine lamivphlomis root water extract is the medicine that main component is developed---Radix Lamiophlomidis Rotatae capsule (record in 2000 editions " Chinese pharmacopoeia), and the realization suitability for industrialized production, pain easing and hemostasis and the aspect such as dentistry, gynaecology, sacroiliitis of wide clinical application after various surgical operations.
Chinese patent ZL2004 10010679.0 " extracts method of total iridoid glycoside and uses thereof " and points out from Tibet medicine lamivphlomis root: a kind of Radix Lamiophlomidis Rotatae total iridoid glycosides extract that obtains from the Root of Common Lamiophlomis water extract has good styptic activity.
Summary of the invention
The purpose of this invention is to provide the application of iridoid glycoside compounds in preparation hemostasis, analgesic.
The present invention is had the iridoid glycoside monomeric compound of analog structure in a large number by the separation to the Radix Lamiophlomidis Rotatae total iridoid glycosides extract, and same pharmacological experiment result shows to have good analgesia, styptic activity, and drug effect is stronger.
The basic structure of iridoid glycoside compounds of the present invention is as follows:
Structure I:
R
1Be OH or sugared aglucon;
R
2Be H or CH
3R
3, R
4, R
5, R
6Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure I I:
R
1Be OH or sugared aglucon;
R
2, R
3Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure III:
R
1Be OH or sugared aglucon;
R
2, R
3Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure I V: arbitrary optics of said structure compound or three-dimensional enantiomorph.
Described sugared aglucon is the monose aglucon of glucose, semi-lactosi, fructose, pectinose, apiose, orange peel sugar or disaccharide or the trisaccharide aglucon that described sugar is arbitrarily made with.
Described iridoid glycoside compounds refer in particular to 8-O-ethanoyl Shanziside methyl ester (8-O-Acetylshanzhiside methylester, barlerin), the bitter glycosides (Penstemoside) of 6-O-ethanoyl Shanziside methyl ester (6-O-acetylshanzhiside methylester), radix scrophulariae, Shanziside methyl ester (Shanzhisidemethyl ester), loganin (Loganin), 5-hydroxyl-7-chloro-Shanziside methyl ester (Phloyoside II) and 8-remove hydroxyl-shanzhiside (8-dehydroxy shanzhiside).
Described iridoid glycoside compounds combines with the dressing of pharmaceutically using always, makes any oral or non-oral dosage form according to ordinary method.
Indication iridoid glycoside compounds of the present invention can separate from Root of Common Lamiophlomis and obtains, can also be from other plant: obtain as separating the Labiatae Paraphlomis plant, and more can be synthetic by chemical process; Also can be on the basis of certain iridoid glycoside compounds, to carry out structural modification or bio-transformation forms.
Below by concrete experiment the iridoid glycoside compounds is further specified as hemostasis, analgesic effect:
1, the preparation of iridoid glycoside compounds
Root of Common Lamiophlomis [Lamiophlomis rotata (Benth.) Kudo] over-ground part 2kg, adding 20 times of water gagings decocts 3 times, each 1 hour, cooled and filtered, macroporous adsorptive resins on the filtrate, ethanol gradient elution after the massive laundering will contain the only iridoid glycoside compounds and partly carry out high performance liquid chromatography preparation (positive SiO
2Filler or anti-phase ODS filler chromatographic column) obtain 8-O-ethanoyl Shanziside methyl ester (8.2g), Phloyoside II (3.2g), sesamoside (0.6g) and 8-and remove hydroxyl-shanzhiside (2.6g).
2, pharmacodynamic experiment
2.1 experiment condition: three grades of Animal Lab.s, 20～25 ℃ of room temperatures are transferred constant temperature.
2.2 experimental subjects: animal BalB/C mouse, body weight 20 ± 2g is provided by experimentation on animals section of Lanzhou General Hospital of Lanzhou Military Command, conformity certification number: the moving word of the doctor of Gansu Province 1402-0201 number.
2.3 medicinal material and instrument: 8-O-ethanoyl Shanziside methyl ester, Shanziside methyl ester, Phloyoside II and 8-remove hydroxyl-shanzhiside, and HPLC measures content respectively greater than 95%; Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract " extract method of total iridoid glycoside and uses thereof " according to national inventing patent and (ZL200410010679.0) prepare from Tibet medicine lamivphlomis root, face with before making the aqueous solution.Etamsylate, the bright medicine company in Shandong side limited-liability company, lot number 0804151.Disposable blood vessel (20ul, length is 12cm), Siping City, Ji County, the Tianjin glassware factory of quantitatively getting.
2.4 the influence to the bleeding time: get 70 of mouse, male and female half and half are divided into 7 groups at random: physiological saline group, etamsylate (0.1g/kg), 8-O-ethanoyl Shanziside methyl ester, Phloyoside II and 8-go hydroxyl-shanzhiside group (0.1g/kg); Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract (0.4g/kg), 10 every group.Physiological saline group tail vein gives physiological saline, all the other are respectively organized the tail vein and are subjected to reagent thing (administration volume 0.2ml/20g), 15min after the administration, fixing mouse, cross-section in order to cutting with mouse tail point 1/3 place, treat that blood overflows voluntarily to pick up counting, inhale to dehematize with filter paper every 30s and drip once, till hemorrhagely stopping (filter paper does not have blood when inhaling) naturally, calculate bleeding time and LVFS (with the physiological saline group relatively).The results are shown in Table 1.
Table 1 Radix Lamiophlomidis Rotatae extract is to the influence in mouse bleeding time
Annotate:
*P＜0.05,
*Compare with the physiological saline group p＜0.01;
The result: by table 1 result as can be known only iridoid glycoside compounds 8-O-ethanoyl Shanziside methyl ester, Shanziside methyl ester, Phloyoside II and 8-go hydroxyl-shanzhiside (0.1g/kg) all can significantly shorten the mouse docking bleeding time, LVFS is respectively 67.95%, 40.10%, 58.78% and 44.79%.Drug effect and etamsylate are suitable.Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract (0.4g/kg) are respectively 20.64% and 42.27% for the LVFS in mouse docking bleeding time.The dosage of only iridoid glycoside class monomeric compound has only 1/4 of Radix Lamiophlomidis Rotatae total iridoid glycosides extract, and comparatively speaking, the styptic activity of only iridoid glycoside class monomeric compound is higher.
2.5 influence: get 70 of mouse to clotting time of mice, grouping and administration are with 1.4,15min after the administration, get blood with the disposable blood vessel insertion mouse corner of the eyes ball rear vein beard of quantitatively getting, to glass capillary, be full of, set level, a bit of every the 30s glass capillary that alternately fractures from two ends, check to have or not the blood clotting silk to occur.In case the blood clotting silk occurs, fracture from the other end and verify, the time of blood clotting silk appears in average two ends, is the clotting time.Compare with the physiological saline group, calculate LVFS.The results are shown in Table 2.
Table 2 Radix Lamiophlomidis Rotatae extract is to the influence of clotting time of mice
Annotate:
*P＜0.05,
*Compare with the physiological saline group p＜0.01
Table 2 result shows that only iridoid glycoside compounds 8-O-ethanoyl Shanziside methyl ester, Shanziside methyl ester, Phloyoside II and 8-go hydroxyl-shanzhiside (0.1g/kg) all can significantly shorten clotting time of mice, and LVFS is respectively 38.63%, 23.90%, 30.37% and 25.17%.Short Blood clotting is suitable with etamsylate.Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract (0.4g/kg) are respectively 17.94% and 23.00% for the LVFS of clotting time of mice.The dosage of only iridoid glycoside class monomeric compound has only 1/4 of Radix Lamiophlomidis Rotatae total iridoid glycosides extract, and comparatively speaking, the procoagulant activity of only iridoid glycoside class monomeric compound is higher.
2.6 Dichlorodiphenyl Acetate causes the influence of mouse writhing number of times: get 70 of mouse, male and female half and half are divided into 7 groups at random: physiological saline group, Paracetamol group (0.2g/kg), 8-O-ethanoyl Shanziside methyl ester, Shanziside methyl ester, Phloyoside II and 8-go hydroxyl-shanzhiside group (0.1g/kg); Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract (0.2g/kg), 10 every group.Physiological saline group tail vein gives physiological saline, and all the other are respectively organized the tail vein and are subjected to reagent thing (administration volume 0.2ml/20g), and 15min after the administration, abdominal injection 0.6% acetic acid 0.2ml/ only observe each treated animal in 20 minutes and turn round the body number of times by what acetic acid caused.Result such as table 3:
Table 3 is the result show: only iridoid glycoside compounds 8-O-ethanoyl Shanziside methyl ester, Shanziside methyl ester, Phloyoside II and 8-go hydroxyl-shanzhiside (0.1g/kg) all can significantly reduce the mouse writhing number of times that abdominal injection acetic acid causes, decrement is respectively 80.86%, 45.31%, 68.98% and 71.95%.The mouse writhing number of times that Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract (0.2g/kg) cause for abdominal injection acetic acid, decrement is respectively 26.40% and 53.14%.The dosage of only iridoid glycoside class monomeric compound has only 1/2 of Radix Lamiophlomidis Rotatae total iridoid glycosides extract, and comparatively speaking, the analgesic effect of only iridoid glycoside class monomeric compound is better.
Table 3 Radix Lamiophlomidis Rotatae extract is turned round the body times influence to what mouse acetic acid caused
Annotate:
*P＜0.05,
*Compare with the physiological saline group p＜0.01
2.7 conclusion: above-mentioned pharmacodynamic experiment result shows, only iridoid glycoside class monomeric compound can significantly shorten mouse docking bleeding stopping period and kapillary clotting time, its haemostatic effect and etamsylate are suitable, and be strong than Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract; Only iridoid glycoside class monomeric compound can significantly reduce the mouse writhing number of times that abdominal injection acetic acid causes simultaneously, shows good analgesic activity, and significantly is better than Root of Common Lamiophlomis water extract and Radix Lamiophlomidis Rotatae total iridoid glycosides extract.
Embodiment
Embodiment 1: with the iridoid glycoside compounds that extracts in the Root of Common Lamiophlomis medicine---and 8-O-ethanoyl Shanziside methyl ester is effective medicinal ingredients; be prepared into hemostasis, analgesia powder injection: in powdered 8-O-ethanoyl Shanziside methyl ester, add the S-WAT of its quality 0.2% as stablizer; make powder injection, Go
60Irradiation sterilization, cleaning condition was packaged into 0.25mg/ in following minute and props up, faces with before adding injection water 1ml to dissolve, quiet notes or intramuscular administration, a 0.25mg, once-a-day.
Embodiment 2: with the iridoid glycoside compounds that extracts in the Root of Common Lamiophlomis medicine---and Shanziside methyl ester is effective medicinal ingredients, be prepared into hemostasis, analgesia powder injection: in the powdered Shanziside methyl ester, add the S-WAT of its quality 0.2% as stablizer, make powder injection, Go
60Irradiation sterilization, cleaning condition was packaged into 0.25mg/ in following minute and props up, faces with before adding injection water 1ml to dissolve, quiet notes or intramuscular administration, a 0.25mg, once-a-day.
Embodiment 3: with the iridoid glycoside compounds that extracts in the Root of Common Lamiophlomis medicine---and Phloyoside II is effective medicinal ingredients, be prepared into hemostasis, analgesia powder injection: in powdered Phloyoside II, add the S-WAT of its quality 0.2% as stablizer, make powder injection, Go
60Irradiation sterilization, cleaning condition was packaged into every of 0.25mg in following minute, faces with before adding injection water 1ml to dissolve, quiet notes or intramuscular administration, a 0.25mg, once-a-day.
Embodiment 4: with the iridoid glycoside compounds that extracts in the Root of Common Lamiophlomis medicine---and it is effective medicinal ingredients that 8-removes hydroxyl-shanzhiside, be prepared into hemostasis, analgesia powder injection: remove to add in hydroxyl-shanzhiside the S-WAT of its quality 0.2% as stablizer at powdered 8-, make powder injection, Go
60Irradiation sterilization, cleaning condition was packaged into 0.25mg/ in following minute and props up, faces with before adding injection water 1ml to dissolve, quiet notes or intramuscular administration, a 0.25mg, once-a-day.
Embodiment 5, the iridoid glycoside compounds to extract in the Root of Common Lamiophlomis medicine---6-O-ethanoyl Shanziside methyl ester is effective medicinal ingredients, is prepared into hemostasis, analgesia external pulvis: powdered 6-O-ethanoyl Shanziside methyl ester is carried out micronizing, Go
60Irradiation sterilization, cleaning condition was packaged into every bottle of 0.5mg (bag), airtight preservation in following minute.External application is spread on the surface of a wound, suitably wrapping.
Embodiment 6, the iridoid glycoside compounds to extract in the Root of Common Lamiophlomis medicine---Shanziside methyl ester is effective medicinal ingredients, be prepared into hemostasis, analgesia oral capsule: with powdered Shanziside methyl ester and Microcrystalline Cellulose and starch with weight ratio 0.01: (1.6～20: (0.5～1.4) mixes, cross 60～80 mesh sieves, tablet processing mode routinely adds an amount of ethanol, mixture is made softwood, cross 22 mesh sieves, make particle, incapsulate, make every oral capsule preparation that to contain above-mentioned active drug component cpd be 1mg.Usage and consumption; Oral, a 1-2 grain, 3 times on the one.
Embodiment 7, the iridoid glycoside compounds to extract in the Root of Common Lamiophlomis medicine---loganin is effective medicinal ingredients, be prepared into hemostasis, analgesia oral capsule: with powdered loganin and Microcrystalline Cellulose and starch with weight ratio 0.01: (1.6～2.0): (0.5～1.4) mixes, cross 60～80 mesh sieves, tablet processing mode routinely adds an amount of ethanol, mixture is made softwood, cross 22 mesh sieves, make particle, incapsulate, make every oral capsule preparation that to contain above-mentioned active drug component cpd be 1mg.Usage and consumption; Oral, a 1-2 grain, 3 times on the one.
Claims (10)
1, the application of iridoid glycoside compounds in the preparation haemostatic medicament.
2, the application of iridoid glycoside compounds in the preparation haemostatic medicament according to claim 1, it is characterized in that: the basic structure of described iridoid glycoside compounds is as follows:
Structure I:
R
1Be OH or sugared aglucon;
R
2Be H or CH
3R
3, R
4, R
5, R
6Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure I I:
R
1Be OH or sugared aglucon;
R
2, R
3Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure III:
R
1Be OH or sugared aglucon;
R
2, R
3Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure I V: arbitrary optics of said structure compound or three-dimensional enantiomorph.
3, as the application of iridoid glycoside compounds as described in the claim 2 in the preparation haemostatic medicament, it is characterized in that: described sugared aglucon is the monose aglucon of glucose, semi-lactosi, fructose, pectinose, apiose, orange peel sugar or disaccharide or the trisaccharide aglucon that described sugar is arbitrarily made with.
4, as the application of iridoid glycoside compounds as described in the claim 2 in the preparation haemostatic medicament, it is characterized in that: described iridoid glycoside compounds is that 8-O-ethanoyl Shanziside methyl ester, 6-O-ethanoyl Shanziside methyl ester, the bitter glycosides of radix scrophulariae, Shanziside methyl ester, loganin, 5-hydroxyl-7-chloro-Shanziside methyl ester or 8-remove hydroxyl-shanzhiside.
5, as the application of iridoid glycoside compounds as described in the claim 2 in the preparation haemostatic medicament, it is characterized in that: described iridoid glycoside compounds combines with the dressing of pharmaceutically using always, makes any oral or non-oral dosage form according to ordinary method.
6, the application of iridoid glycoside compounds in the preparation analgesic.
7, as the application of iridoid glycoside compounds as described in the claim 6 in the preparation analgesic, it is characterized in that: the basic structure of described iridoid glycoside compounds is as follows:
Structure I:
R
1Be OH or sugared aglucon;
R
2Be H or CH
3R
3, R
4, R
5, R
6Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure I I:
R
1Be OH or sugared aglucon;
R
2, R
3Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure III:
R
1Be OH or sugared aglucon;
R
2, R
3Be H, OH, OCOCH
3, a kind of among Cl, the Br;
Structure I V: arbitrary optics of said structure compound or three-dimensional enantiomorph.
8, as the application of iridoid glycoside compounds as described in the claim 7 in the preparation analgesic, it is characterized in that: described sugared aglucon is the monose aglucon of glucose, semi-lactosi, fructose, pectinose, apiose, orange peel sugar or disaccharide or the trisaccharide aglucon that described sugar is arbitrarily made with.
9, as the application of iridoid glycoside compounds as described in the claim 7 in the preparation analgesic, it is characterized in that: described iridoid glycoside compounds is that 8-O-ethanoyl Shanziside methyl ester, 6-O-ethanoyl Shanziside methyl ester, the bitter glycosides of radix scrophulariae, Shanziside methyl ester, loganin, 5-hydroxyl-7-chloro-Shanziside methyl ester or 8-remove hydroxyl-shanzhiside.
10, as the application of iridoid glycoside compounds as described in the claim 7 in the preparation analgesic, it is characterized in that: described iridoid glycoside compounds combines with the dressing of pharmaceutically using always, makes any oral or non-oral dosage form according to ordinary method.
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| CN102875617A (en) * | 2012-09-12 | 2013-01-16 | 安徽医科大学 | Geniposide derivative, preparation method thereof and application of geniposide derivative to inflammation resistance |
| CN103130849A (en) * | 2011-11-29 | 2013-06-05 | 河南科技大学 | Method for preparing high-purity 8-acetyl Shanzhiside methyl ester |
| CN107158446A (en) * | 2017-05-02 | 2017-09-15 | 中国药科大学 | The hemostasis of the composite active carbon fibre of class containing only iridoid glycoside, antibacterial, promoting healing medical dressing, Preparation method and use |
| CN107823470A (en) * | 2017-11-10 | 2018-03-23 | 中国药科大学 | One kind is containing genuine Tibetan herbal medicine lamiophlomis rotata ointment formulations, preparation method and its usage |
| CN108503678A (en) * | 2017-02-24 | 2018-09-07 | 深圳曜曦生命科技有限公司 | A kind of iridoid and its preparation method and application |
| CN109280066A (en) * | 2018-11-16 | 2019-01-29 | 成都瑞芬思生物科技有限公司 | A kind of preparation method of 8-O- acetyl mountain Cape jasmine glycosides methyl esters and 6-O- acetyl mountain Cape jasmine glycosides methyl esters |
| CN109568332A (en) * | 2018-12-27 | 2019-04-05 | 上海交通大学 | Iridoid is preparing the application in analgesic |
| CN109796511A (en) * | 2019-03-05 | 2019-05-24 | 山东省药学科学院 | A kind of new iridoid and preparation method thereof and medical usage |
| CN111067930A (en) * | 2019-12-31 | 2020-04-28 | 江西杏林白马药业股份有限公司 | Lamiophlomis rotate (Benth.) kudo extract nanometer preparation and preparation method thereof |
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| CN103130849A (en) * | 2011-11-29 | 2013-06-05 | 河南科技大学 | Method for preparing high-purity 8-acetyl Shanzhiside methyl ester |
| CN103130849B (en) * | 2011-11-29 | 2016-04-06 | 河南科技大学 | A kind of method preparing 8-acetyl mountain Cape jasmine glycosides methyl esters |
| CN102875617A (en) * | 2012-09-12 | 2013-01-16 | 安徽医科大学 | Geniposide derivative, preparation method thereof and application of geniposide derivative to inflammation resistance |
| CN108503678A (en) * | 2017-02-24 | 2018-09-07 | 深圳曜曦生命科技有限公司 | A kind of iridoid and its preparation method and application |
| CN107158446A (en) * | 2017-05-02 | 2017-09-15 | 中国药科大学 | The hemostasis of the composite active carbon fibre of class containing only iridoid glycoside, antibacterial, promoting healing medical dressing, Preparation method and use |
| CN107823470A (en) * | 2017-11-10 | 2018-03-23 | 中国药科大学 | One kind is containing genuine Tibetan herbal medicine lamiophlomis rotata ointment formulations, preparation method and its usage |
| CN109280066A (en) * | 2018-11-16 | 2019-01-29 | 成都瑞芬思生物科技有限公司 | A kind of preparation method of 8-O- acetyl mountain Cape jasmine glycosides methyl esters and 6-O- acetyl mountain Cape jasmine glycosides methyl esters |
| CN109568332A (en) * | 2018-12-27 | 2019-04-05 | 上海交通大学 | Iridoid is preparing the application in analgesic |
| CN109796511A (en) * | 2019-03-05 | 2019-05-24 | 山东省药学科学院 | A kind of new iridoid and preparation method thereof and medical usage |
| CN109796511B (en) * | 2019-03-05 | 2021-10-22 | 山东省药学科学院 | Novel iridoid compound and preparation method and medical application thereof |
| CN111067930A (en) * | 2019-12-31 | 2020-04-28 | 江西杏林白马药业股份有限公司 | Lamiophlomis rotate (Benth.) kudo extract nanometer preparation and preparation method thereof |
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Application publication date: 20090408 |