CN101879178B - Medicinal application of timosaponin BIII - Google Patents
Medicinal application of timosaponin BIII Download PDFInfo
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- CN101879178B CN101879178B CN2010102385744A CN201010238574A CN101879178B CN 101879178 B CN101879178 B CN 101879178B CN 2010102385744 A CN2010102385744 A CN 2010102385744A CN 201010238574 A CN201010238574 A CN 201010238574A CN 101879178 B CN101879178 B CN 101879178B
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Abstract
The invention relates to medicinal application of timosaponin BIII, in particular to application of timosaponin BIII serving as an effective ingredient extracted and separated from Chinese medicinal anemarrhena rhizome in preparing a medicament for treating diabetes. Meanwhile, in vivo and in vitro pharmacological experiments prove that the compound has remarkable inhibiting activity on alpha-glucosidase, can effectively reduce blood sugar of animals, and can be applied in preparing an alpha-glucosidase inhibitor and preparing the medicament for treating the diabetes. The timosaponin BIII compound shows good diabetes activity resistance in vivo, develops the application field thereof, and may become an effective medicament for treating the diabetes in the future.
Description
Patent application of the present invention is that applying date of continuing is on May 16th, 2007, and application number is 2007100407304, and denomination of invention is further divided an application for the application for a patent for invention of " preparation method and its usage of timosaponin BIII ".
Technical field
The present invention relates to the purposes of plant extract, be specifically related to a kind of application of effective ingredient timosaponin BIII in preparation treatment diabetes medicament of extraction separation from the Chinese medicine Rhizoma Anemarrhenae.
Background technology
Diabetes are that concentration of glucose raises in the blood owing to insulin in the human body definitely or relatively lacks a kind of common clinical that causes, and then sugar discharges from urine in a large number, and polydipsia, polyuria, polyphagia occur, become thin, symptom such as dizzy, weak.Further develop and then cause the various serious acute and chronic complication of whole body, threaten healthy.Wherein the type i diabetes patient loses the function that produces insulin fully, and dependence insulinize is essential and uses all the life; Insulin is in relative deficiency state in the type ii diabetes patient body, needn't rely on insulin fully and can treat with other medicines.In diabetics, type ii diabetes has accounted for great majority.Diabetes are the commonly encountered diseases in the modern society, high morbidity, serious threat human beings'health and life.
At present, the main method of western medical treatment diabetes is insulinize and hypoglycemic drugs such as oral sulphanylureas, biguanides, but insulinize costs an arm and a leg, and other types of drug or curative effect are limited, or toxic and side effects is obvious.In recent years; Big quantity research shows; Chinese medicine demonstrates very big advantage in the clinical treatment of type ii diabetes, but the existing most effective ingredient of Chinese patent medicine is unclear, and the mechanism of action is not clear; Dosage form falls behind, and urgency waits to develop effective ingredient and the mechanism of action is clear, stable and controllable for quality, dosage form is advanced, take Chinese medicine preparation easy to carry.
Alpha-glucosidase is alpha-D-glucose glycosides hydrolytic enzyme again, and it is the hydrolytic enzyme of maltose in the small intestinal, sucrose.Carbohydrate in the diet is under the effect of alpha-glucosidase; Discharge glucose and absorb entering blood through small intestinal; It is the main cause that post-prandial glycemia raises; And postprandial hyperglycemia can cause that thereby the insulin sensitivity reduction increases the weight of the state of an illness and causes a series of complication, therefore finds suitable enzyme inhibitor, to preventing and treating diabetes and complication thereof important meaning will be arranged.Suppress alpha-glucosidase activity, the generation and the absorption that can slow down glucose, blood sugar lowering level.
Chinese medicine Rhizoma Anemarrhenae clearing away heat-fire promotes the production of body fluid and moisturizes, and mainly has effects such as antibiotic, antiviral, analgesic, blood sugar lowering.Up to the present; Had the activity of Rhizoma Anemarrhenae total glycosides, 1-timosaponin A-1 III and chimonin anti-diabetic aspect; Activity report to timosaponin BIII is less; Hiroyuki Kodama is at its article [Effect of six steroidal saponins isolated from anemarrhenae rhizoma on platelet aggregation and hemolysis in human blood; Clinica Chimica Acta, 1999 (289): 79-88] reported its influence in to human body platelet polymerization and haemolysis aspect.But also do not see the report of timosaponin BIII [(3 β, 5 β, 25S)-26-O-β-D-glucopyranosyl-furan steroid-20 (22)-alkene-3,26-glycol-3-O-β-D-glucopyranosyl (1 → 2)-O-β-D-galactopyranoside] treatment diabetes aspect.
Report as follows for the extraction separation method of timosaponin BIII is existing:
Ma Baiping has reported the extraction process [research of furostanol in the Rhizoma Anemarrhenae of timosaponin B; Acta Pharmaceutica Sinica, 1996,31 (4): 271-277]; This method is earlier with solvent extraction; With silica gel column chromatography, the mixture of gained need separate with preparation HPLC repeatedly, purification again, gets timosaponin B (this chemical compound is timosaponin BIII).
Hiroyuki Kodama has also reported separation method [the Effect of six steroidal saponins isolated from anemarrhenae rhizoma on platelet aggregation and hemolysis in human blood of this chemical compound; Clinica Chimica Acta, 1999,289:79-88]; This method also is earlier with solvent extraction; Use macroporous resin column, silica gel column chromatography more respectively, products obtained therefrom reuse HPLC separates, and promptly gets timosaponin BIII.
More than two kinds of methods methods of all having adopted solvent extraction, column chromatography for separation and HPLC to separate preparation.But the HPLC separation method only is applicable to laboratory, can not be satisfied with the application in the industry.Method for preparing of the present invention is simple relatively, has replaced the HPLC preparation with technological operations such as crystallizations, more steps to suitability for industrialized production to go a step further.
Summary of the invention
The object of the present invention is to provide the method for preparing of a kind of timosaponin BIII, this method adopts chemistry route from the Chinese medicine Rhizoma Anemarrhenae, to isolate effective ingredient---timosaponin BIII.
Another object of the present invention is to provide the medical usage of above-mentioned timosaponin BIII,, the application of this chemical compound in preparation treatment diabetes medicament is provided through the inside and outside pharmacological testing of body.
Timosaponin BIII structure involved in the present invention is following, and this compound molecule formula is C
45H
74O
18, molecular weight is 902, and chemical being called (3 β, 5 β, 25S)-and 26-O-β-D-glucopyranosyl-furan steroid-20 (22)-alkene-3,26-glycol-3-O-β-D-glucopyranosyl (1 → 2)-O-β-D-galactopyranoside.
For reaching the foregoing invention purpose, the present invention adopts following technical scheme:
The method for preparing of timosaponin BIII disclosed by the invention, its step is following:
1) gets rhizoma ane marrhenae, use C
6～C
30The defat of aliphatic solvent percolation, drying;
2) above-mentioned defat afterproduct is used C
1～C
5Alcohol reflux extracts, filters, and merging filtrate, distilling under reduced pressure removes and desolvates, and gets Rhizoma Anemarrhenae extractum;
3) with step 2) in the extractum of gained with the water suspendible, and use water saturated C
4～C
8Alcohol extraction, remove and desolvate drying;
4) with above-mentioned steps 3) in the product of gained use silica gel column chromatography, earlier with the chloroform eluting, use chloroform-n-butyl alcohol eluting then, collect the flow point that contains timosaponin BIII, reclaim solvent to dried;
5) gained sample in the step 4) being separated through silica gel column chromatography again, is the eluant eluting with the chloroform-methanol, collects the flow point that contains timosaponin BIII, reclaims solvent, gets timosaponin BIII powder;
6) above-mentioned dried powder is used C
1～C
5Alcohol carry out recrystallization, timosaponin BIII.
Above-mentioned method for preparing step 2) in, raw material and C
1～C
5The weight ratio of alcohol is 1: 5～20; In the step 3), the weight ratio of raw material and water is 1: 0.5～3.5, raw material and C
4～C
8The weight ratio of alcohol be 1: 0.5～3.5; In the step 4), the volume ratio of chloroform-n-butyl alcohol is 20: 1～1: 1; In the step 5), the volume ratio of chloroform-methanol is 10: 1～1: 1.
In the above-mentioned method for preparing, preferred gasoline of the degreasing solvent described in the step 1) or petroleum ether; Step 2) preferred 50～90% ethanol of the extraction solvent described in; The preferred n-butyl alcohol of extractant described in the step 3); C described in the step 6)
1～C
5Pure particular methanol or ethanol.
The present invention adopts said method to extract interior, the external test of pesticide effectiveness of body that the timosaponin BIII that obtains at first carries out routine.
1. external alpha-glucosidase suppresses experiment.
This experiment mainly is through this chemical compound of observation in vitro the alpha-glucosaccharase enzyme inhibition rate to be drawn it to suppress effect.
The result shows that medicine of the present invention is close with the positive control drug acarbose in the activity of vitro inhibition alpha-glucosidase, can in the preparation alpha-glucosidase inhibitor, use.
2. glucose tolerance test in the body:
Glucose tolerance is to weigh one of glycometabolic leading indicator, and blood glucose can return to basic value in the certain hour of feed back, and ill Mus blood glucose in the identical time can not return to basic value.
This experiment is model with the mice, through measuring to testing before the sugar and to the blood glucose value after the sugar.The mice of can't help water with normal fasting is the blank group; The mice that gives distilled water and sucrose with per os is a model control group; To the mice administration respectively of model control group, institute's medicament is timosaponin BIII, carries out testing in the body through the blood glucose value of measuring several groups of different time mices.The result shows that medicine of the present invention can significantly reduce the ICR mice to before sugared and to the blood glucose value after the sugar, obviously improves its glucose load, can treat in the diabetes medicament in preparation and use.
Beneficial effect of the present invention:
The method for preparing of timosaponin BIII is simple relatively in this invention, has replaced the HPLC preparation with technological operations such as some crystallizations, more steps to suitability for industrialized production to go a step further.Simultaneously; Diabetes are the very serious diseases that influence human health; But also do not treat the specific medicament of type ii diabetes at present, this chemical compound has shown good anti-diabetic activity in vivo and in vitro, and for finding first; Not only open up its application, also might become the active drug of following treatment diabetes.
The specific embodiment
Below in conjunction with specific embodiment the present invention is done further elaboration, but do not limit the present invention.
Embodiment 1: the extraction separation method of timosaponin BIII.
Get 5.0 kilograms of rhizoma ane marrhenaes, the defat of gasoline percolation, drying.With 25 liter of 85% alcohol reflux three times, refluxed 2 hours at every turn, filter merging filtrate.Decompression and solvent recovery, being concentrated into does not have the alcohol flavor, gets 1 kilogram of Rhizoma Anemarrhenae extractum.
With extractum with 6 premium on currency suspendibles, with 4 liters of n-butanol extractions of water saturation four times.With n-butanol layer recovery, drying, get extractum 135 grams.Mix appearance with methanol and carry out silicagel column (2700 grams, 160-200 order) chromatography.Earlier with the chloroform eluting, to color light till; Use chloroform-n-butyl alcohol (1: 1) eluting then.TLC detects, and developing solvent is n-butyl alcohol-ethyl acetate-water (4: 1: 5) upper strata.With 10% phosphomolybdic acid ethanol 110oC is developer, merges the flow point that contains timosaponin BIII, reclaims solvent to doing, and gets extractum 23 grams.This extractum is continued to separate through silica gel column chromatography, is the eluant eluting with chloroform-methanol (5: 3), collects the flow point that contains timosaponin BIII, reclaims solvent, gets powder 3 grams.
Above-mentioned dried powder with dissolve with methanol, crystallization, is got the white granular solid.Continue to use recrystallizing methanol, get timosaponin BIII.Measure through the HPLC area normalization method: the purity of this chemical compound is 90%.Its spectral data is following:
The unformed powder of timosaponin BIII white.Liebermann-Burchard reaction and Molish reaction all are positive.
HRESIMS (positive mode) m/z:925.4766 [M+Na]
+(calcd.925.4773);
1HNMR (400MHz, pyridine-d
5): δ 5.37 (1H, d, J=7.8Hz, H-1 "), 4.87 (1H, d, J=7.6Hz, H-1 '), 4.77 (1H, d, J=7.6Hz, H-1 " '), 1.62 (3H, s, H-21), 0.94 (3H, d, J=6.8Hz, H-27), 0.91 (3H, s, H-19), 0.67 (3H, s, H-18);
13C NMR (100MHz, pyridine-d
5): δ 152.2 (C-22), 106.0 (C-1 "), 105.1 (C-1 " '), 103.5 (C-20), 102.5 (C-1 '), 84.5 (C-16), 81.7 (C-2 '); 78.4 (C-5 "), 78.4 (C-3 "), 78.4 (C-5 "), 77.9 (C-3 "), 76.9 (C-3 '), 76.5 (C-5 '), 75.5 (C-2 "); 75.1 (C-2 " '), 75.1 (C-3), 75.1 (C-26), 71.6 (C-4 "), 71.6 (C-4 " '), 69.7 (C-4 '), 64.5 (C-17); 62.6 (C-6 "), 62.6 (C-6 " '), 62.1 (C-6 '), 54.6 (C-14), 43.7 (C-13), 41.0 (C-9); 40.9 (C-12), 36.8 (C-5), 35.1 (C-8), 35.1 (C-10), 34.3 (C-23), 33.6 (C-25); 31.3 (C-15), 30.8 (C-1), 30.8 (C-4), 26.7 (C-2), 26.7 (C-6), 26.7 (C-7); 23.9 (C-19), 23.5 (C-24), 21.2 (C-11), 17.1 (C-27), 14.3 (C-18), 11.8 (C-21).
Embodiment 2: the extraction separation method of timosaponin BIII.
Get 5.0 kilograms of rhizoma ane marrhenaes, the defat of petroleum ether percolation, drying.Extract three times with 40 liters of methanol eddies, refluxed 2 hours at every turn, filter merging filtrate.Decompression and solvent recovery, being concentrated into does not have the alcohol flavor, gets 1.2 kilograms of Rhizoma Anemarrhenae extractum.
With extractum with 10 premium on currency suspendibles, with 10 liters of n-amyl alcohols extraction of water saturation four times.With the recovery of n-amyl alcohol layer, drying, get extractum 150 grams.Mix appearance with methanol and carry out silicagel column (2700 grams, 160-200 order) chromatography.Earlier with the chloroform eluting, to color light till; Use chloroform-n-butyl alcohol (5: 1) eluting then.TLC detects, and developing solvent is n-butyl alcohol-ethyl acetate-water (4: 1: 5) upper strata.With 10% phosphomolybdic acid ethanol is developer, merges the flow point that contains timosaponin BIII, reclaims solvent to doing, and gets extractum 24 grams.This extractum is continued to separate through silica gel column chromatography, is the eluant eluting with chloroform-methanol (6: 1), collects the flow point that contains timosaponin BIII, reclaims solvent, gets powder 3.1 grams
Above-mentioned dried powder with dissolve with ethanol, crystallization, is got the white granular solid.Continue to use recrystallizing methanol, get timosaponin BIII.Measure through the HPLC area normalization method: the purity of this chemical compound is 87%.
Embodiment 3: the test of vitro inhibition alpha-glucosidase activity
A) reagent and instrument:
Alpha-glucosidase (EC 232-604-7) is purchased the Sigma company in the U.S.,
PNPG (4 Nitrobenzol-α-D-pyranglucoside) (EC 223-189-3) purchases the company in Sigma
Natrium carbonicum calcinatum, phosphate etc. are analytical pure.
ELIASA: BIO-TECK Instruments, the U.S. produces.
B) reagent preparation
Phosphate buffer (67mM, PH6.8): the K that weighing is an amount of
2HPO
43H
2O solution, it is for use to transfer to 6.8,4 ℃ of preservations of pH with phosphoric acid.
Enzyme liquid: take by weighing an amount of alpha-glucosidase lyophilized powder and use 67mM, the dilution of PH6.8 phosphate buffer, concentration 0.5mg/ml, 0.5ml one pipe packing ,-20 ℃ are frozen.
Substrate PNPG: with phosphate buffer (67mM PH6.8) is made into 29mM α-PNPG,, packing ,-20 ℃ of preservations.
Reaction terminating liquid: with distilled water preparation 1M Na
2CO
3, 4 ℃ of preservations.
C) operating procedure
Chinese medicine suppresses active mensuration:
Response system is: 67mM phosphate buffer (PH=6.8) 145ul, and 0.5mg/ml alpha-glucosidase 5ul, the drug dilution liquid 20ul of debita spissitudo is hatched 10min for 37 ℃, adds 0.029M pNPG10ul, hatches 10min for 37 ℃, adds 100ul 1M Na
2CO
3, 405nm detects the amount that under the effect of enzyme, discharges nitrophenol.
Blank well: buffer+enzyme liquid+substrate+stop buffer.
Blank hole: buffer+stop buffer.
Reacting hole: buffer+enzyme liquid+medicine+substrate+stop buffer.
Reaction control wells: buffer+enzyme liquid+medicine+stop buffer.
Reading: 96 orifice plates are surveyed the OD value at 405nm place with ELIASA.
D) date processing
A: blank well; B: blank hole; C: reacting hole; D: reaction control wells.
Suppression ratio (%)=[1-(c-d)/(a-b)] * 100%
Timosaponin BIII is as shown in table 1 to the inhibition activity of alpha-glucosidase.
Table 1: timosaponin BIII is to the inhibition living-article of alpha-glucosidase
The result shows: timosaponin BIII is active close with the positive control drug acarbose in the inhibition of external alpha-glucosidase.
Embodiment 4: the influence to normal ICR mice carbohydrate tolerance in the body is tested
A) experiment material
Laboratory animal: 160 of cleaning level ICR mices, body weight 23 ± 2g, male, by Chinese Academy of Sciences's Shanghai Experimental Animal Center supply, the animal quality quality certification: SCXK (Shanghai) 2003-0003 number.
The steady bold and unconstrained type blood glucose meter of Johnson & Johnson, the steady bold and unconstrained type blood sugar test paper of Johnson & Johnson, LIFESCAN company produces.
Sucrose, analytical pure AR, China Medicine (Group) Shanghai Chemical Reagent Co., produces.
B) experimental condition
SPF level ICR mouse experiment receptacle, temperature: 23 ± 1 ℃, humidity: 50-70%, noise:＜50dB, illumination: 150-200Lx, light and shade replaced (6:00-18:00 in evening early), free diet in 12 hours.
C) test dose, approach and volume
100mg/Kg, irritating stomach is 0.3ml to reagent volume, sucrose 0.2ml, positive drug 0.1ml.
D) test method
Normal ICR mice fasting can't help water 15 hours, was divided into four groups.Wherein water is can't help in one group of mice fasting, as the blank group; Its excess-three group its mouse oral gives distilled water and sucrose sucrose 2.5g/kg, as model control group.To the mice of model control group gastric infusion respectively, one group of institute's medicament is timosaponin BIII, and other one group of institute's medicament is an acarbose, remaining one group as contrast.Measure to give behind the glucose 0,30,60 respectively, the blood glucose value of 120min, observe each group and give behind the glucose situation of change of area under each time point blood glucose curve.
Timosaponin BIII is as shown in table 2 to the influence of normal ICR mice carbohydrate tolerance in vivo.
Table 2: timosaponin BIII is to the influence
of normal ICR mice carbohydrate tolerance
Annotate: compare with model control group:
*P＜0.01
Area under the blood glucose curve=1/4 * (0min blood glucose value+2 * 30min blood glucose value+3 * 60min blood glucose value+120min blood glucose value).
The result shows: timosaponin BIII can significantly reduce the ICR mice to before sugared and to the blood glucose value after the sugar, obviously improves its glucose load.See table 2.
Claims (1)
1. the application of Rhizoma Anemarrhenae extract in the preparation alpha-glucosidase inhibitor that contains timosaponin BIII, said Rhizoma Anemarrhenae extract is produced as follows:
1) gets rhizoma ane marrhenae, with gasoline or the defat of petroleum ether percolation, drying;
2) to above-mentioned defat afterproduct with 50% ~ 90% alcohol reflux, filter, merging filtrate, distilling under reduced pressure removes and desolvates, Rhizoma Anemarrhenae extractum;
3) with step 2) in the extractum of gained with the water suspendible, and use water saturated n-butanol extraction, except that desolvating drying;
4) with above-mentioned steps 3) in the product of gained use silica gel column chromatography, earlier with the chloroform eluting, use volume ratio to be 20:1 ~ 1:1 chloroform-n-butyl alcohol eluting then, collect the flow point that contains timosaponin BIII, reclaim solvent to dried;
5) gained sample in the step 4) being separated through silica gel column chromatography again, is that the chloroform-methanol of 10:1 ~ 1:1 is the eluant eluting with the volume ratio, collects the flow point that contains timosaponin BIII, reclaims solvent, must contain timosaponin BIII powder;
6) above-mentioned dried powder is carried out recrystallization with methanol or ethanol.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102385744A CN101879178B (en) | 2007-05-16 | 2007-05-16 | Medicinal application of timosaponin BIII |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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|---|---|---|---|
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| CN101879178B true CN101879178B (en) | 2012-11-07 |
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| CN105640976A (en) * | 2016-03-04 | 2016-06-08 | 广东药学院 | Joint application of total timsapinins and dimethyldiguanide in preparation of drugs for treating diabetes or hyperlipidemia |
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Non-Patent Citations (1)
| Title |
|---|
| NOBORU NAKASHIMA,et al..ISOLATION OF PSEUDOPROTOTIMOSAPONIN AIII FROM RHIZOMES OF ANEMARRHENA ASPHODELOZDES AND ITS HYPOGLYCEMIC ACTIVITY IN STREPTOZOTOCIN-INDUCED DIABETIC MICE.《Journal of Natural Products》.1993,第56卷(第3期),第345-350页. * |
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