CN101664462B - Hypoglycemic active part and hypoglycemic effective component of madder, preparation method and application thereof - Google Patents
Hypoglycemic active part and hypoglycemic effective component of madder, preparation method and application thereof Download PDFInfo
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- CN101664462B CN101664462B CN200810141286XA CN200810141286A CN101664462B CN 101664462 B CN101664462 B CN 101664462B CN 200810141286X A CN200810141286X A CN 200810141286XA CN 200810141286 A CN200810141286 A CN 200810141286A CN 101664462 B CN101664462 B CN 101664462B
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Abstract
The invention relates to a hypoglycemic active part of madder and a preparation method thereof, an effective component obtained by extracting from the hypoglycemic active part and a preparation method thereof, and application of the madder in reducing blood sugar and application of the active part and the effective component of the madder. The active part is a chloroform active part and a methanol active part which are obtained by crushing and moistening the root of a medicinal plant, namely the madder, and orderly using chloroform and methanol for leaching. The invention adopts the Chinese medicament, namely the madder, as a raw material; the madder has rich sources, is a natural botanical medicament, and has the characteristics of relative safety and low cost; and the method provides a wider source of medicaments for treating diabetes, and has good social value and economic value. In addition, the method has important effect on the development of novel high-efficiency and safe medicaments for reducing the blood sugar after the meal.
Description
Technical field
The present invention relates to a kind of Radix Rubiae blood-sugar-lowering effective parts and preparation method thereof; Also relate to a kind of effective ingredient that extracts acquisition by this blood-sugar-lowering effective parts and preparation method thereof simultaneously, also relate to the application of Radix Rubiae aspect blood sugar lowering and the application of effective site and effective ingredient thereof.
Background technology
Diabetes be a kind of be characteristic with the hyperglycemia, metabolism disorder for the performance, with the closely-related systemic disease of insulin secretion, be the clinical syndrome that causes owing to the h and E factor interaction.Absolute or relative deficiency and target tissue reduce insulin sensitivity because of insulin secretion, cause a series of metabolism disorders such as sugar, albumen, fat, power and water Xie Zhi.Diabetes mainly are divided into two types: type i diabetes (being insulin dependent diabetes mellitus (IDDM)) and type ii diabetes (being non-insulin-dependent diabetes mellitus), the latter accounts for the 99%-95% of patient's sum.The clinical manifestation of diabetes is more than three (polyphagia, polydipsia, polyurias), few (weight loss), a hyperglycemia symptom.The complication that diabetes cause (like acute complicationses such as cardiovascular, kidney, retina and neural chronic complicating diseases, diabetic ketoacidosis, hyperosmolar nonketotic diabetic comas) is the main cause that causes death.All diabetic complications can be through strict glycemic control; From preventing to the full extent; If diabetics can be controlled at the blood sugar level of oneself near in the normal range of blood sugar, then diabetic complication just can not occur, and perhaps occurs than later and degree is also lighter.At present, China's diabetics is about 1,200 ten thousand, and the whole world is about 1.5 hundred million, has become to threaten human No. 3 " healthy killer ", so prevention and treatment diabetes have become global problem.Treatment of diabetes is a target with the control fasting glucose mainly for many years, and medicine mainly concentrates on sulphanylureas and biguanides for a long time.Recent study is found; Post-prandial glycemia also is the main hazard factor that diabetic complication takes place, and post-prandial glycemia is the highest stage of blood sugar level in one day, and its persistent period can be for 8 hour or be longer; Long-time high-caliber post-prandial glycemia can increase the weight of diabetes itself; Blood glucose is further raise, if at table just can the better controlled hyperglycemia, then can avoid its after the meal the sugar in the blood circulation pile up; Therefore, the control post-prandial glycemia can be described as the control hyperglycemia, prevents and treats the important behave of diabetes.In the existing Remedies for diabetes, sulfonylurea drugs is blood sugar lowering through stimulating secretion of insulin; Then through increasing peripheral tissues to the utilization of glucose and blood sugar lowering, both all have better curative effect to reducing type ii diabetes patient fasting glucose to biguanides, but very limited to the effect that reduces post-prandial glycemia.
Most carbohydrates in the food are starch and sucrose etc.; Starch earlier after in saliva and the pancreatic juice AMS be decomposed into oligosaccharide; Oligosaccharide is decomposed into glucose at intestinal epithelial cell brush border place by alpha-glucosidase and after being absorbed; Cause the post-prandial glycemia peak, therefore, the activity that suppresses alpha-glucosidase becomes an effective way that reduces post-prandial glycemia.Alpha-glucosidase inhibitor is one type of new oral hypoglycemic drug researching and developing out in the seventies later stage; Its mechanism of action is: emulative inhibition alpha-glucosidase; Delay and hinder the digestion of carbohydrate, postpone absorption, effectively postpone and alleviate the time and the degree of post-prandial glycemia rising from the glucose of disaccharidase, oligosaccharide and polysaccharide; Take for a long time and can also reduce fasting blood glucose level, this type of medicine all is suitable for I, type ii diabetes.Alpha-glucosidase inhibitor not only has definite curative effect to diabetes, and for obesity, chronic viral hepatitis B, AIDS and tumor certain therapeutical effect is arranged all.Be used for this type of clinical medicine at present acarbose, voglibose and miglitol are arranged.Existing this type of medicine cost is higher, and has the intestinal side effect.
Radix Rubiae is a rubia, popular name Herba Chenopodii Hybridi, Radix Rubiae Yunnanensis, HUOXUECAO, saw grass, draws rattan, Radix seu Caulis Schisandrae Sinensis, is the dry root and rhizome of Maguireothamnus speciosus Radix Rubiae (Rubia cordifolia L.).Kind surplus the Rubiaceae Rubia plant whole world has 60 mainly is distributed in Asia, Europe, America and Africa.There is 24 kind of 10 mutation in China, and the various places that spread all over the country are especially with the southwest most species.Radix Rubiae is widely distributed; But be the main producing region still so far with Shaanxi, Shanxi and Henan, Radix Rubiae bitter in the mouth cold in nature, GUIXIN Liver Channel; Have cooling blood for hemostasis, expelling wind and removing dampness, dispel become silted up stimulate the menstrual flow, the effect of blood circulation promoting and blood stasis dispelling, eliminating phlegm and stopping cough, cure mainly haematemesis, epistaxis, metrorrhagia due to blood-heat, amenorrhea, traumatic injury.Mainly contain water miscible ring peptide series matter, liposoluble constituent anthraquinone and glucosides, naphthoquinone and glucosides thereof in the Radix Rubiae, contain terpenoid, cupreol, fatty acid cpds and trace element in addition.
Summary of the invention
The object of the present invention is to provide a kind of effective site---chloroform extract that preparation has the inhibition alpha-glucosidase activity that from the plant Radix Rubiae, extracts, a kind of method that obtains effective ingredient of separating from this effective site also is provided simultaneously.
The present invention also aims to provide a kind of this Radix Rubiae effective site and the application of effective ingredient aspect the preparation hypoglycemic drug, especially in the application aspect the phlorose enzyme inhibitor.
To achieve these goals, technical scheme of the present invention has adopted a kind of Radix Rubiae blood-sugar-lowering effective parts, this effective site be madder plant through pulverize, moistening, and the chloroform effective site and the methanol effective site that obtain with chloroform and methanol lixiviate successively.
Described blood-sugar-lowering effective parts is preferably chloroform effective site.
Simultaneously, technical program of the present invention also lies in providing a kind of Radix Rubiae blood sugar lowering effective ingredient, this effective ingredient by chloroform effective site through silica gel column chromatography and with petroleum ether-acetone gradient elution after; Pass through the silica gel H column chromatography again, petroleum ether-acetone eluting detects merging with TLC; Through Sephadex LH-20 column chromatography, acetone eluting, the chemical compound 11 that obtains; 3-dihydroxy-2-methyl base anthraquinone, chemical compound 2 1-hydroxy-2-methyl anthraquinones and chemical compound 31,2-dihydroxyanthraquinone.
Technical program of the present invention also lies in providing a kind of method for preparing of Radix Rubiae blood-sugar-lowering effective parts; May further comprise the steps: the Radix Rubiae rhizome is pulverized; Use the acetic acid moistening, with difference lixiviate under chloroform and the methanol room temperature 1-3 times, filter successively; Reclaim solvent, obtain chloroform effective site and methanol effective site.
The chloroform effective site that obtains is through 200-300 order silica gel column chromatographies, petroleum ether-acetone gradient elution (95:5～9:1), obtain having the part that suppresses alpha-glucosidase activity; Through the silica gel H column chromatography, petroleum ether-acetone (15:1) eluting detects merging with TLC with this part; Through Sephadex LH-20 column chromatography, the acetone eluting makes the blood sugar lowering effective ingredient; It is chemical compound 11; 3-dihydroxy-2-methyl base anthraquinone, chemical compound 2 1-hydroxy-2-methyl anthraquinones and chemical compound 31,2-dihydroxyanthraquinone.
Technical scheme of the present invention has also adopted the application of Radix Rubiae aspect blood sugar lowering.
Further say the application of Radix Rubiae blood-sugar-lowering effective parts---chloroform extract aspect the preparation hypoglycemic drug.Particularly in the application aspect alpha-glucosidase inhibitor.
Technical scheme of the present invention has also adopted this Radix Rubiae blood sugar lowering effective ingredient; It is chemical compound 1; 3-dihydroxy-2-methyl base anthraquinone; Chemical compound 1-hydroxy-2-methyl anthraquinone and chemical compound 1, the application of 2-dihydroxyanthraquinone aspect the preparation hypoglycemic drug is especially in the application aspect alpha-glucosidase inhibitor.
Radix Rubiae effective ingredient of the present invention identifies that through structure its structure type is mainly anthraquinone analog compound.These chemical compounds distribute general in plant and are easy to get, and reactive compound involved in the present invention is from any crude drug that contains this compounds, preferably from the chloroform extract in the Chinese medicine Radix Rubiae crude drug.
Radix Rubiae blood-sugar-lowering effective parts of the present invention has good alpha-glucosidase and suppresses active, under the same conditions than the alpha-glucosidase of clinical antidiabetic drug acarbose commonly used suppress active will be good many.The effective ingredient that obtains from this effective site; Be chemical compound 1,3-dihydroxy-2-methyl base anthraquinone, chemical compound 1-hydroxy-2-methyl anthraquinone and chemical compound 1; The 2-dihydroxyanthraquinone all has very high alpha-glucosidase and suppresses active; And chemical compound 1,3-dihydroxy-2-methyl base anthraquinone and chemical compound 1-hydroxy-2-methyl anthraquinone have the activity of competitive inhibition alpha-glucosidase, belong to same alpha-glucosidase with acarbose and suppress type; But it suppresses activity and is higher than acarbose far away, can be used to prepare hypoglycemic drug thing after the meal.It is raw material that the present invention adopts the Chinese medicine Radix Rubiae; The Radix Rubiae source is abundant; Have comparatively safe and cheap characteristics as a kind of natural plant, the invention provides Remedies for diabetes source more widely, have favorable social and economic worth.In addition, has important function to developing efficient, safe reduction post-prandial glycemia novel drugs.
Experimentation shows that Madder extract is that effective site and effective ingredient all have alpha-glucosidase inhibition activity, and it is higher that the particularly fat-soluble extractive part of its extract reaches the activity intensity and the present widely used hypoglycemic drug acarbose that therefrom separate the chemical compound that obtains.
Description of drawings
Fig. 1 is for extracting the effective ingredient 1 that obtains, the inhibitory action kinetic curve of 3-dihydroxy-2-methyl base anthraquinone from Radix Rubiae;
Fig. 2 is for extracting the inhibitory action kinetic curve of the effective ingredient 1-hydroxy-2-methyl anthraquinone that obtains from Radix Rubiae;
Fig. 3 is for extracting the effective ingredient 1 that obtains, the inhibitory action kinetic curve of 2-dihydroxyanthraquinone from Radix Rubiae.
The specific embodiment
Present embodiment is that each extract of Radix Rubiae is the method for distilling and the preliminary screening active ingredients of effective site.
The method for preparing of Radix Rubiae blood-sugar-lowering effective parts is: with Radix Rubiae rhizome 500g, after the pulverizing, use the acetic acid moistening; With difference lixiviate under chloroform and the methanol room temperature 2 times, filter successively, reclaim solvent; Obtain the chloroform blood-sugar-lowering effective parts (Rc, 4.5g) with the methanol blood-sugar-lowering effective parts (Rm, 12.8g).
Determination of activity:
Method: microwell plate method
Principle: alpha-D-glucose glycosides enzymatic hydrolysis 4-Nitrobenzol-α-D-pyranglucoside (PNP-G); Produce nitrophenol (PNP; Yellow substance has absorption maximum about 400m), thus alpha-glucosidase inhibitor can suppress alpha-glucosidase combines to reduce PNP with substrate burst size.Calculate the enzyme inhibition activity of extract with the changes of contents of PNP in the certain hour internal reaction system.
Instrument: Multiskan MK3 ELIASA (thermoelectric Shanghai Instr Ltd.), 96 microwell plates, all size pipettor, the biochemical incubator (Shanghai one permanent Science and Technology Ltd.) of LRH-150.
Reagent: alpha-glucosidase (Sigma company, EC3.2.1.20, from baker ' s yeast; Lot number: 105K1313), right-nitrobenzophenone-α-the D-pyranglucoside (PNPG, Sigma company; Lot number: 026K1516), phosphate buffer (PH6.8), acarbose (acarbose; Sigma company, lot number: 16869), other reagent are analytical pure.
Detection method:
112L kaliumphosphate buffer (pH6.8) adds 20 μ L (concentration is 0.2U/mL) alpha-glucosidase, 8 μ L sample solutions, and 37 ℃ of constant temperature 15min add 20 μ L2.5mmol/L PNPG, 37 ℃ of isothermal reaction 15min.The terminator Na that adds 80 μ L (concentration is 0.2mol/L) again
2CO
3Solution is surveyed the OD value down in the 405nm wavelength.4 groups are established in experiment altogether, and every group three hole is respectively: a. negative control group; B. blank control group; C. sample determination group; D. sample matched group.Calculate suppression ratio by following method, and obtain corresponding IC with Origin software
50Value.
Experimental result is as shown in table 1: Radix Rubiae chloroform extract and methanolic extract all than the alpha-glucosidase of clinical antidiabetic drug acarbose commonly used suppress active will be good many, and half suppression ratio IC
50Show that more definitely chloroform extract can be used as the effective site that Radix Rubiae suppresses alpha-glucosidase.
The alpha-glucosidase of the different extracts of table 1 Radix Rubiae suppresses active
Present embodiment is under activity instructs, and prepares the method that effective ingredient is a reactive compound from Radix Rubiae chloroform effective site.
Concrete grammar is: the chloroform effective site (4.5g) that embodiment 1 is obtained is through 200～300 order silica gel column chromatographies; Petroleum ether-acetone gradient elution (95:5～9:1); Obtain 4 parts, wherein (Rc-3 1.6g) has inhibition alpha-glucosidase activity (table-2) to the 3rd part.This part is through the silica gel H column chromatography, and petroleum ether-acetone (15:1) eluting detects merging with TLC, and through Sephadex LH-20 column chromatography, the acetone eluting obtains chemical compound 1 (12.5mg), chemical compound 2 (5.5mg) and chemical compound 3 (120.7mg).
Embodiment 3
Present embodiment is the determination of activity that chemical compound suppresses alpha-glucosidase in the Radix Rubiae.
Assay method: with embodiment 1.
Measure the result: experimental result is seen table 2.3 kinds of chemical compound primary dcreening operation suppression ratio all are higher than positive control Acarbose, and IC
50Value all is lower than 50 μ gmL
-1, much smaller than clinical antidiabetic drug Acarbose (IC commonly used
50=1081.27 μ gmL
-1), having very high alpha-glucosidase and suppress vigor, the effective ingredient that can be used as Radix Rubiae inhibition alpha-glucosidase is developed.
The alpha-glucosidase of effective ingredient suppresses active in table 2 Radix Rubiae
Embodiment 4
Present embodiment suppresses confirming of type for the test-compound alpha-glucosidase.
3 kinds of chemical compounds are got suitable two variable concentrations (seeing figure) respectively; Reaction substrate PNPG gets 5 variable concentrations; Under 400nm, measure enzymatic activity respectively, guarantee that reaction cumulative volume and enzyme dosage are constant, and under each concentration all with not enzyme-added same mixture liquid as contrast.By the enzyme activity under the different concentration of substrate conditions of series, press the Lineweave-Burk graphing method, be abscissa with 1/ [S], 1/V is a vertical coordinate, draws the inhibitory action kinetic curve (seeing accompanying drawing) of 3 chemical compounds respectively, obtains the K of phlorose glycosidase
mValue is 6.04mmolL
-1
Can know that by Fig. 1-Fig. 3 chemical compound 1 belongs to competitive inhibitor, response speed V with 2 pairs of phlorose glycosidase inhibiting functions of chemical compound
MaxRemain unchanged with the inhibitor concentration increase, according to competitive inhibition kinetics equation: 1/K
m'=1/{K
m(1+ [I]/K
i) try to achieve the K of chemical compound 1 and 2
iValue is respectively: 25 μ gmL
-1With 11.26 μ gmL
-1Explain that chemical compound 1 is the same with 2 with the complexation site of phlorose glycosidase substrate on this enzyme, belong to same alpha-glucosidase and suppress type, but it suppresses activity and be higher than acarbose far away, show that this chemical compound has certain application value.
3 of chemical compounds belong to noncompetitive and suppress response speed V
MaxDiminish Michaelis constant K along with the increase of inhibitor concentration
mRemain unchanged.Suppress kinetics equation: 1/V ' according to noncompetitive
Max=1/V
Max(1+ [I]/K
i), can obtain the K of chemical compound 3
iValue is 3.33 μ gmL
-1Explain it both can and enzyme, also can combine, thereby reduce enzymatic activity with enzyme-substrate complex, reach the blood sugar lowering effect.
Embodiment 5
Present embodiment is that the structure that has the inhibiting active component of alpha-glucosidase in the Radix Rubiae is identified.
Chemical compound 3 bronzing acicular crystals (acetone), mp288～289 ℃, EIMS m/z (%): 240 [M]
+(100), 212 (20), 184 (12), 155 (10), 138 (10), 128 (10).
1H NMR (400MHz, DMSO) δ: 7.62 (1H, d, J=8.3Hz, H-3), 7.20 (1H, d, J=8.3Hz, H-4), 8.19-8.12 (2H, m, H-5,8), 7.92-7.86 (2H, m, H-6,7).
13C NMR (100MHz, DMSO) δ: 150.7 (C-1), 152.7 (C-2), 121.1 (C-3); 120.8 (C-4), 121.0 (C-4a), 132.8 (C-4b), 126.7 (C-5); 135.0 (C-6), 133.9 (C-7), 133.5 (C-8), 188.7 (C-9); 180.4 (C-10), 133.4 (C-8a), 116.1 (C-8b).Data are consistent with bibliographical information, confirm that chemical compound 3 is 1, the 2-dihydroxyanthraquinone.
Claims (2)
1. Radix Rubiae blood-sugar-lowering effective parts; It is characterized in that: this effective site is that the medicinal plants Radix Rubiae is through pulverizing, acetic acid moistening, successively with difference lixiviate under chloroform and the methanol room temperature 1-3 times, filtration; Reclaim solvent, obtain chloroform effective site and methanol effective site.
2. Radix Rubiae blood-sugar-lowering effective parts according to claim 1 is characterized in that: described blood-sugar-lowering effective parts is a chloroform effective site.
3
.A kind of Radix Rubiae blood sugar lowering effective ingredient, it is characterized in that: this extraction of effective components is following: with chloroform effective site through 200-300 order silica gel column chromatographies, petroleum ether-acetone gradient elution, ratio is 95:5 ~ 9:1, obtains having inhibition
α-The part of glucosidase activity; With this part through the silica gel H column chromatography, petroleum ether-acetone eluting, both ratios are 15:1, detect to merge with TLC, through Sephadex LH-20 column chromatography, the acetone eluting makes the blood sugar lowering effective ingredient, i.e. chemical compound
11,3-dihydroxy-2-methylanthraquinone, chemical compound
21-hydroxy-2-methyl anthraquinone and chemical compound
31, the 2-dihydroxyanthraquinone; Wherein, chloroform effective site is that Radix Rubiae is pulverized, and use the acetic acid moistening,, filters recovery solvent and getting with chloroform lixiviate at room temperature 1-3 times.
4
.A kind of method for preparing of Radix Rubiae blood-sugar-lowering effective parts as claimed in claim 1; It is characterized in that: may further comprise the steps: Radix Rubiae is pulverized; Use the acetic acid moistening, with difference lixiviate under chloroform and the methanol room temperature 1-3 times, filter successively; Reclaim solvent, obtain chloroform effective site and methanol effective site.
5
.A kind of method for preparing of Radix Rubiae blood sugar lowering effective ingredient as claimed in claim 3 is characterized in that: with chloroform effective site through 200-300 order silica gel column chromatographies, petroleum ether-acetone gradient elution, ratio is 95:5 ~ 9:1, obtains having inhibition
α-The part of glucosidase activity; With this part through the silica gel H column chromatography, petroleum ether-acetone eluting, both ratios are 15:1, detect to merge with TLC, through Sephadex LH-20 column chromatography, the acetone eluting makes the blood sugar lowering effective ingredient, i.e. chemical compound
11,3-dihydroxy-2-methylanthraquinone, chemical compound
21-hydroxy-2-methyl anthraquinone and chemical compound
31, the 2-dihydroxyanthraquinone; Wherein, chloroform effective site is that Radix Rubiae is pulverized, and use the acetic acid moistening,, filters recovery solvent and getting with chloroform lixiviate at room temperature 1-3 times.
6
.The application of a kind of Radix Rubiae blood-sugar-lowering effective parts as claimed in claim 1 aspect the preparation hypoglycemic drug.
7
.Application according to claim 6 is characterized in that: this effective site is in the application aspect alpha-glucosidase inhibitor.
8
.The application of a kind of Radix Rubiae blood sugar lowering effective ingredient as claimed in claim 3 aspect the preparation hypoglycemic drug.
9
.Application according to claim 8 is characterized in that: this effective ingredient is in the application aspect alpha-glucosidase inhibitor.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308954A (en) * | 2000-12-18 | 2001-08-22 | 来春荣 | Oral liquid for treating diabetes and its preparing process |
| CN1800133A (en) * | 2006-01-25 | 2006-07-12 | 河南中医学院 | Preparation method of extracting hemostatic substance 1,3-dihydroxyanthraquinone from India madder charcoal |
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- 2008-09-04 CN CN200810141286XA patent/CN101664462B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308954A (en) * | 2000-12-18 | 2001-08-22 | 来春荣 | Oral liquid for treating diabetes and its preparing process |
| CN1800133A (en) * | 2006-01-25 | 2006-07-12 | 河南中医学院 | Preparation method of extracting hemostatic substance 1,3-dihydroxyanthraquinone from India madder charcoal |
Non-Patent Citations (4)
| Title |
|---|
| 康文艺 等.茜草抗氧化成分研究.《河南大学学报（医学版）》.2006,第25卷(第3期),6-8. * |
| 张琳 等.茜草的化学成分研究进展.《现代中医药》.2008,第28卷(第2期),52-54. * |
| 日本生药学杂志.茜草中的蒽醌.《中国野生植物》.1989,48. * |
| 杨连荣 等.茜草的化学成分与药理作用研究进展.《中医药信息》.2007,第24卷(第1期),21-23. * |
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