CN101766668B - Burdock extract and preparation method and application thereof - Google Patents
Burdock extract and preparation method and application thereof Download PDFInfo
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- CN101766668B CN101766668B CN2008102082462A CN200810208246A CN101766668B CN 101766668 B CN101766668 B CN 101766668B CN 2008102082462 A CN2008102082462 A CN 2008102082462A CN 200810208246 A CN200810208246 A CN 200810208246A CN 101766668 B CN101766668 B CN 101766668B
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- fructus arctii
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- lappaol
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Abstract
The invention relates to a great burdock fruit extract and a preparation method and application thereof. The content of total lignan compounds in the extract by weight percent is 64-90 percent, wherein the content of Arctigenin is 3-6 percent, the content of Arctiin is 32-45 percent and the content of other lignan compounds is 13-55 percent. According to pharmacological testing results, the great burdock fruit extract of the invention has a strong aldose reductase suppression function and can be used for preparing drugs for curing diabetes-related complications such as diabetic cataract, diabetic retinopathy, keratopathy and diabetic neuropathy.
Description
Technical field
The present invention relates to a kind of Fructus Arctii extract; In addition, the invention still further relates to the preparation method and the purposes of this Fructus Arctii extract.
Background technology
At present, diabetes have become the disease of the third-largest serious threat human health after tumor, cardiovascular disease, are classified as one of the world's three big pertinacious diseases by WHO.If in time diagnosis, regular treatment can not cause multiple chronic complicating diseases.According to statistics, the concurrent neuropathy of diabetics over half; 30% the concurrent proliferative retinopathy of diabetics is arranged approximately, wherein have every year 1.2% may develop into blind; The concurrent diabetic nephropathy of type ii diabetes patient (DN) of the type i diabetes patient of 30%-40% and 15%-20% can develop into hypertension, nephrotic syndrome etc. by occurring albuminuria at first, and severe patient finally causes renal failure and death.In view of the significant damage of diabetic complication, seek the corresponding treatment medicine and have great economic worth and social meaning.
The activation of polyhydric alcohol bypass is one of pathogeny of the various chronic complicating diseases of diabetes, wherein, aldose reductase (aldose reductase, AR) play a part crucial.Aldose reductase is the crucial rate-limiting enzyme in the polyalcohols metabolic pathway, glucose and galactose can be converted into corresponding reduzate sorbitol and galactitol.When blood sugar concentration maintained normal physiological level, AR was not activated.When diabetes took place, AR then was activated, and impelled intravital conversion of glucose to become sorbitol, because sorbitol is difficult for by cell membrane, so caused the accumulation of sorbitol in born of the same parents.At present, the research of a large amount of forward positions is verified, secular diabetic complication such as part tissue of eye disease, neuropathy, nephropathy etc., all with body in sorbitol accumulate relevant.
Fructus Arctii is " Chinese medicine that records of Chinese pharmacopoeia version in 2000, the former relieving the exterior syndrome with drugs of pungent in flavor and cool in nature class Chinese medicine that belongs to, have the function of dispelling wind and heat pathogens, lung qi dispersing rash, resolving toxin and disinhibiting the throat, be used for diseases such as anemopyretic cold, cough with copious phlegm, measles, rubella, laryngopharynx swelling and pain, consumption 6-12g/ day.
Summary of the invention
The present invention to be that the Fructus Arctii crude drug is processed extraction with regard to one of technical problem of solving, propose a kind of Fructus Arctii extract, and its active site carried out accurate in locating; In addition, the present invention also will propose the preparation method and the purposes of this Fructus Arctii extract.This Fructus Arctii extract has significant aldose reductase inhibitory action, can be used for treating diabetic complication.
The Fructus Arctii extract that the present invention proposes, the weight content of Lignanoids compounds is 64-90% (determined by ultraviolet spectrophotometry).
Preferably, in this extract, the weight content of aretigenin is 3-6% (high effective liquid chromatography for measuring), the weight content of Arctiin is 32-45% (high effective liquid chromatography for measuring), the gross weight content of Arctiin and aretigenin is 35%-51%, and the weight content of all the other Lignanoids compounds (martairesinol, Lappaol A, Lappaol C, Lappaol F, Lappaol H and Arctignan E) is 13%-55% (determined by ultraviolet spectrophotometry).
The preparation method of the Fructus Arctii extract that the present invention proposes comprises the steps:
Take by weighing the Fructus Arctii crude drug, be ground into coarse powder, adding 8 times of weight concentrations is the ethanol of 95% (weight concentration is to call wt% in the following text), reflux, extract, 2 times, and each 3h filters, and behind the merging filtrate, being evaporated to does not have the alcohol flavor;
The gained fluid extract is left standstill to room temperature, incline except that its upper strata liquid part, it is the ethanol of 20% (wt%) that underflow extractum adds concentration, stir, make its abundant suspendible, to become concentration be the suspension of 20% (wt%) to thin up again, last D101 type macroporous adsorptive resins;
Check effluent with TLC, when producing, stop to go up sample with the corresponding speckle of control sample chromatograph;
Wash with water earlier to water lotion Monish reaction and be negative, be 30%, 50%, 75% and 95% ethanol elution more successively with weight concentration, elution flow rate 2BV/h, each Concentraton gradient is inhaled and is taken off 4BV, combined wt concentration is 50%, 75% and 95% ethanol elution, after concentrating under reduced pressure became fluid extract, vacuum drying was to constant weight, promptly under-0.1MPa, 60 ℃ condition.Test subsequently will prove: can detect Arctiin (arctiin) as stated above in Zhi Bei the Fructus Arctii extract, aretigenin (arctigenin), martairesinol (matairesinol), Lappaol A, Lappaol C, Lappaol F, 8 kinds of Lignanoids compounds of Lappaol H and ArctignanE.
Fructus Arctii extract of the present invention, prove through pharmacological testing, have significant aldose reductase inhibitory action, can be used to prepare the medicine of preventing and treating diabetic complication, as diabetic cataract, retinopathy, keratopathy and/or diabetic peripheral neuropathy.
Description of drawings
Fig. 1 is the UPLC/MS chromatogram of Fructus Arctii extract of the present invention.
Fig. 2-9 is the UPLC/MS chromatogram of the contained 8 kinds of Lignanoids compounds of Fructus Arctii.
Figure 10 is the HPLC collection of illustrative plates of Arctiin reference substance.
Figure 11 is the Arctiin assay HPLC collection of illustrative plates of Fructus Arctii extract.
Figure 12 is the HPLC collection of illustrative plates of aretigenin reference substance.
Figure 13 is the aretigenin assay HPLC collection of illustrative plates of Fructus Arctii extract.
The specific embodiment
Below in conjunction with the drawings and specific embodiments, further set forth the present invention.These embodiment are interpreted as only being used to the present invention is described and are not used in restriction protection scope of the present invention.After the content of having read the present invention's record, those skilled in the art can make various changes or modifications the present invention, and these equivalences change and modify and fall into claim of the present invention institute restricted portion equally.
Embodiment 1 (preparation Fructus Arctii extract)
(the Fructus Arctii crude drug is available from medical material branch company of Xuzhou medicine limited company to get Fructus Arctii crude drug 50kg, Xuzhou, the place of production), be ground into coarse powder, adding 400L concentration is 95% (wt%) ethanol, reflux, extract, 2 times, each 3h filters, behind the merging filtrate, being evaporated to concentrated extract does not have the alcohol flavor.
The gained fluid extract leaves standstill to room temperature, inclines except that its upper strata liquid part, its underflow extractum is added 20% (wt%) ethanol stir, and makes its abundant suspendible, and to become concentration be the suspension of 20% (wt%) to thin up again, last D
101The type macroporous adsorptive resins.Check effluent with TLC, stop to go up sample when producing with the corresponding speckle of control sample chromatograph.Being washed to water lotion Monish reaction earlier is negative, use the ethanol elution of 30%, 50%, 75% and 95% (wt%) more successively, elution flow rate 2BV/h, each Concentraton gradient eluting 4BV, merge 50%, 75% and 95% ethanol elution, after concentrating under reduced pressure became fluid extract, vacuum drying promptly got the 7.5kg of Fructus Arctii extract to constant weight under-0.1MPa, 60 ℃ condition.
Embodiment 2 (composition of Fructus Arctii extract is differentiated)
Fructus Arctii extract with embodiment 1 makes adopts the UPLC/MS analytical method, according to molecular weight, and its contained chemical compound of qualitative identification, concrete operations are as follows:
1. instrument
The Acquity Ultra Performance of Waters company type liquid chromatograph, the MicromassZQ of Waters company type mass detector, Masslynx chromatographic work station, reagent are chromatographically pure (U.S. Fisher company).
2. experimental technique
2.1 the preparation of test specimen
It is an amount of to take by weighing Fructus Arctii extract's sample, is mixed with 2mg/ml solution with mobile phase, standby.
2.2.UPLC chromatographic condition
Chromatographic column: Acquity UPLC BEH C-18 (1.7 μ m, 2.1mm * 50mm, 5 μ m); Flow velocity: 0.21ml/min; Mobile phase is: water-methanol (6: 4); 40 ℃ of column temperatures; Detect wavelength 280nm, sample size: 0.5 μ l.
2.3MS condition
Electron spray ionisation source (ESI), positive and negative ion detects, ionization voltage: 2.6kV (+), 2.9kV (-); 120 ℃ of ion source temperatures; Taper hole voltage 30V; Desolventizing temperature degree: 300 ℃ (+), 250 ℃ (-); Desolventizing gas (N2) flow velocity: 500L/h (+), 600L/h (-).Diode matrix detector (PDA) is connected with mass spectrum, is about 0.1min lag time between the two.
3. experimental result
In order to determine each component in the Fructus Arctii extract, adopt diode matrix (PDA) and positive and negative ion to detect, the result shows existence 8 kinds of components (as shown in Figure 1) in the Fructus Arctii extract, the UV maximum absorption wavelength of each component is 280nm, except Arctiin and martairesinol, the positive and negative ion detection mode of each component all can detect the characteristic ion peak, i.e. M+Na, M-H.According to its mass spectral characteristic, determine that each component is followed successively by Arctiin, aretigenin, martairesinol, Lappaol A, Lappaol C, Lappaol F, Lappaol H, Arctignan E (shown in Fig. 2-9).
Fructus Arctii extract with embodiment 1 makes adopts ultraviolet spectrophotometry, is external standard with the aretigenin, measures the content of its total lignans class in 280nm wavelength place, the corresponding percentage composition that draws other compositions in this extract.Concrete operations are as follows:
1. material
The aretigenin reference substance is available from Sigma company.
2. method
2.1 the preparation of reference substance solution
It is an amount of that precision takes by weighing the aretigenin reference substance, adds methanol and make the solution that every ml contains 30 μ g, promptly.
2.2 the preparation of need testing solution
Take by weighing the about 10mg of Fructus Arctii extract that embodiment 1 makes, the accurate title, decide, and puts in the 25ml volumetric flask, adds dissolve with methanol and be diluted to scale, shakes up, and filters, and precision is measured subsequent filtrate 1ml, puts in the 10ml volumetric flask, adds methanol and is diluted to scale, shakes up, promptly.
3. assay
Get reference substance and need testing solution respectively,, measure absorbance, calculate, promptly at 280nm wavelength place according to ultraviolet visible spectrophotometry (an appendix V of Chinese Pharmacopoeia version in 2005 A).
Through the assay to many batch samples, the content of total lignans compounds and Arctiin is 64%-90% in the Fructus Arctii extract that embodiment 1 makes, and then the content of other composition is 10%-36%.
Embodiment 4
Fructus Arctii extract with embodiment 1 makes adopts high performance liquid chromatography, is external standard with Arctiin, aretigenin, by integral area ratio, measures the content of its aretigenin and Arctiin.The content of total lignans class measured among the embodiment 3 and Arctiin is deducted the aretigenin that records in the present embodiment and the total content of Arctiin, promptly get the content of all the other total lignans classes in this extract.Concrete operations are as follows:
1. reagent
Aretigenin reference substance (Sigma company), and the Arctiin reference substance (self-control is finished structure through UV, IR, MS, NMR and is identified, the HPLC assay, purity is 98.5%).Reagent is chromatographically pure (U.S. TEDIA company).
2. method
2.1 chromatographic condition
2.1.1 Arctiin
Chromatographic column: with octadecylsilane chemically bonded silica is filler, is mobile phase with methanol-water (45: 55); The detection wavelength is 280nm.Theoretical cam curve is calculated by the Arctiin peak should be not less than 6000.
2.1.2 aretigenin
Chromatographic column: with octadecylsilane chemically bonded silica is filler, is mobile phase with methanol-acetonitrile-water (20: 20: 60); The detection wavelength is 280nm.Theoretical cam curve is calculated by the aretigenin peak should be not less than 5000.
2.2 the preparation of reference substance solution
2.2.1 Arctiin
It is an amount of that precision takes by weighing the Arctiin reference substance, adds methanol and make the solution that every ml contains 40 μ g, promptly.
2.2.2 aretigenin
It is an amount of that precision takes by weighing the aretigenin reference substance, adds methanol and make the solution that every ml contains 5 μ g, promptly.
2.3 the preparation of need testing solution
Take by weighing the 20mg of Fructus Arctii extract that embodiment 1 makes, the accurate title, decide, and puts in the 50ml volumetric flask, adds dissolve with methanol and be diluted to scale, shakes up, and filters, and precision is measured subsequent filtrate 5ml, puts in the 25ml volumetric flask, adds methanol and is diluted to scale, shakes up, promptly.
3. assay
Get reference substance and need testing solution respectively, measure according to high performance liquid chromatography (an appendix VI of Chinese Pharmacopoeia version in 2005 D): the HPLC collection of illustrative plates of Arctiin reference substance as shown in figure 10, the HPLC collection of illustrative plates of aretigenin reference substance is as shown in figure 12; In this extract the HPLC collection of illustrative plates of Arctiin assay as shown in figure 11, the HPLC collection of illustrative plates of aretigenin assay is as shown in figure 13 in this extract.
Through the assay to many batch samples, the content that records Arctiin in this extract is at 32%-45%, and the content of aretigenin is at 3%-6%, and the total content of Arctiin and aretigenin is at 35%-51%.
Content according to total lignans class measured among the embodiment 3 and Arctiin is 64%-90%, deducts the aretigenin that records in the present embodiment and the total content 35%-51% of Arctiin, and the content that promptly gets all the other total lignans classes in this extract is 13%-55%.
Embodiment 5
The Fructus Arctii extract that embodiment 1 is made is used to carry out external aldose reductase inhibition experiment, experiment showed, that this extract has significant aldose reductase inhibitory action.
1. material and method
1.1 main agents
NADPH, DL-glycosides oil aldehyde (sigma company product), 2 mercapto ethanol (Shanghai chemical reagents corporation of Chinese Medicine group chemical pure), Li
2SO
4(Chemical Reagent Co., Ltd., Sinopharm Group), microplate reader (
Instruments, Inc, USA), refiner (IKA T10 basic), Fructus Arctii extract, buffer solution of potassium phosphate (0.1M, ph6.2) (potassium dihydrogen phosphate, dipotassium hydrogen phosphate Chemical Reagent Co., Ltd., Sinopharm Group), epalrestat tablet (Nanjing, Nanjing pharmaceutical Co. Ltd).
1.2 the extraction of Mus aldose reductase
Frozen rat lens thaws for 4 ℃, gets homogenate in 30 buffer solution of potassium phosphate in 4 ℃ of 10ml (0.1M, ph6.2), and 4 ℃, the centrifugal 30mins of 4400rpm get supernatant, and 1.5ml/ manages packing, and-70 ℃ frozen.Whole operation is all being carried out below 4 ℃.
1.3 the mensuration of aldose reductase extract protein content
With the bovine serum albumin is standard, uses the Coomassie brilliant blue method, measures absorbance (OD) value in the 595nm place, goes out protein content in the AR crude extract by regression equation calculation.
1.4 the foundation of external enzymatic reaction system and the detection of enzymatic activity
Enzymatic reaction is carried out on 96 orifice plates, and whole system volume is 250ul, just decides each material concentration to be: Li
2SO
4400mmol/L, buffer solution of potassium phosphate 0.67mmol/L, 2 mercapto ethanol 5mmol/L, NADPH0.3mmol/L, DL-glycosides oil aldehyde 3mmol/L, thick zyme extract 50ul.At first will not have the plate of substrate to place 25 ℃ of insulations 10 minutes, add the carrying out that substrate starts reaction at last.Monitoring 10min down with microplate reader 340nm is blank with the sample that does not contain substrate, and the absorbance that the NADPH autoxidation is caused in the deduction blank system changes.The enzyme that the absorbance per minute changes 0.001 unit during with 25 ℃ is defined as a unit of enzyme activity.
1.5 the checking of enzymatic reaction system
Select to have gone on the market aldose reductase inhibitor---epalrestat is verified this reaction system.Under the certain condition of epalrestat concentration, the substrate solution that adds variable concentrations is measured enzyme activity, then changes the amount of epalrestat, draws the enzyme activity under a series of different concentration of substrate conditions, draw 1/[S] ~ the 1/v double reciprocal curve, determine that it suppresses type and document contrast.
1.6 the in-vitro screening of aldose reductase inhibitor
With Li
2SO
4, 2 mercapto ethanol is dissolved in and is configured to certain density solution in the buffer solution of potassium phosphate (0.1M, ph6.2) and is referred to as reagent A, Fructus Arctii extract is dissolved in reagent A and is diluted to 6 concentration gradients, 12.5,25,50,100,200,400 μ g/ml, add enzymatic reflection system and measure its suppression ratio.
Suppression ratio=(activity/not dosing activity after the 1-dosing) * 100%
2. result of the test
2.1AR the mensuration of protein content roughly
The thick pheron concentration of AR is 2.2mg/ml.
2.2 according to Paasche he to the checking of enzymatic reaction system
By epalrestat to the inhibiting 1/[S of AR] ~ the 1/v double reciprocal curve, be defined as that he is a uncompetitive to the inhibitory action of AR according to Paasche, conform to bibliographical information, prove the reliability (seeing Table 1) of this system.
2.3 result of the test
The aldose reductase suppression ratio of table 1. Fructus Arctii total lignans
an＝3.
Result of the test shows, Fructus Arctii extract of the present invention has significant aldose reductase inhibition activity, when concentration is 200 μ g/mL, its inhibition to aldose reductase is active in the aldose reductase inhibitor that has gone on the market---epalrestat is similar, and it suppresses the active good dose-effect relationship that shows.
As everyone knows, the activation of polyhydric alcohol bypass is one of pathogeny of the various chronic complicating diseases of diabetes, wherein, aldose reductase (aldose reductase, AR) play a part crucial.Aldose reductase is the crucial rate-limiting enzyme in the polyalcohols metabolic pathway, glucose and galactose can be converted into corresponding reduzate sorbitol and galactitol.When blood sugar concentration maintained normal physiological level, AR was not activated.When diabetes took place, AR then was activated, and impelled intravital conversion of glucose to become sorbitol, because sorbitol is difficult for by cell membrane, so caused the accumulation of sorbitol in born of the same parents.At present, the research of a large amount of forward positions is verified, secular diabetic complication such as part tissue of eye disease, neuropathy, nephropathy etc., all with body in sorbitol accumulate relevant.
So Fructus Arctii extract of the present invention can be applicable to preparation control diabetic complication, as the medicine of diabetic cataract, retinopathy, keratopathy and diabetic peripheral neuropathy.
Claims (2)
1. the preparation method of a Fructus Arctii extract is characterized in that, comprises the steps:
Take by weighing the Fructus Arctii crude drug, be ground into coarse powder, the ethanol that to add 8 times of weight concentrations be 95% (wt%), reflux, extract, 2 times, each 3h filters, and behind the merging filtrate, being evaporated to does not have the alcohol flavor;
The gained fluid extract is left standstill to room temperature, incline except that its upper strata liquid part, it is the ethanol of 20% (wt%) that underflow extractum adds concentration, stir, make its abundant suspendible, to become concentration be the suspension of 20% (wt%) to thin up again, last D101 type macroporous adsorptive resins;
Check effluent with TLC, when producing, stop to go up sample with the corresponding speckle of control sample chromatograph;
Wash with water earlier to water lotion Monish reaction and be negative, be 30% with concentration successively again, 50%, the ethanol elution of 75% and 95% (wt%), elution flow rate 2BV/h, each Concentraton gradient is inhaled and is taken off 4BV, merging concentration is 50%, 75% and 95% ethanol elution, after concentrating under reduced pressure becomes fluid extract,-0.1MPa, vacuum drying is to constant weight under 60 ℃ the condition, promptly make the Fructus Arctii extract that Lignanoids compounds content is 64-90% (wt%), and the content of aretigenin is 3-6% (wt%) in this Fructus Arctii extract, the content of Arctiin is 32-45% (wt%), martairesinol, Lappaol A, Lappaol C, LappaolF, the content of Lappaol H and Arctignan E is 13-55% (wt%).
2. the purposes of the Fructus Arctii extract that makes of claim 1 in the medicine of preparation control diabetic cataract, retinopathy, keratopathy and/or diabetic peripheral neuropathy.
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| CN103751707B (en) * | 2013-12-31 | 2016-06-08 | 赵玉妹 | Oral liquid of a kind of great burdock achene beauty treatment and eliminating spot and preparation method thereof |
| CN108245506B (en) * | 2016-12-29 | 2022-12-20 | 鲁南制药集团股份有限公司 | Application of arctigenin in preparation of medicine for treating corneal ulcer |
| CN107088188A (en) * | 2017-04-14 | 2017-08-25 | 上海中医药大学 | The medical usage of butyric acid compound and its derivative |
| CN113491722A (en) * | 2020-04-02 | 2021-10-12 | 上海君砚投资管理咨询有限公司 | Composition for reducing blood sugar and application thereof |
| CN113952374B (en) * | 2021-09-24 | 2023-02-28 | 江西普正制药股份有限公司 | Lignan extract co-extracted by Du Zhonghe burdock and extraction method thereof |
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