CN101362766B - Extraction method for preparing high-purity allocryptopine - Google Patents
Extraction method for preparing high-purity allocryptopine Download PDFInfo
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Abstract
The invention relates to a method for preparing and extracting high-purity allocryptopine. An initial extract is obtained by making use of ethanol to carry out refluxing, extraction and drying by distillation on natural papaveraceae plant; most alkaloid of the initial extract is subsided out in acidity alcohol, the pH value of the solution is adjusted to 7.5-8.5 by sig water and then to 9.5-10.5 after filtration, filtration is carried out again and filter residue is a crude extract; the crude extract is carried out refluxing treatment by ethyl acetate and methanol and filtered; the high-content allocryptopine monomer is obtained after the recrystallization of residue obtained from the filtrate by decompression and drying by distillation in methanol or chloroform-methanol or anhydrous alcohol. The method expands the scale of raw materials for extracting allocryptopine and provides a new economic and feasible way for preparing high-purity allocryptopine monomer. The method applies raw materials which are available, has simple and easy separation and purification technique and relatively low cost and is suitable for mass production.
Description
Technical field
The invention belongs to the extraction process of effective component of natural product, relate generally to the alkaloidal method of extraction separation reactive monomer from natural phant, particularly relate to a kind of method for preparing high-purity allocryptopine of from the Chinese medicine Pink Plumepoppy Herb, separating.
Background technology
Allocryptopine (Allocryptopine) be mainly from plants such as papaveracease (as Pink Plumepoppy Herb, snowpoppy, pilewort etc.) extraction separation obtain, perhaps chemosynthesis obtains.Its pharmacological action is mainly antiarrhythmic effect, and it suppresses effect greater than cigarette amine the animal irregular pulse that napelline is caused; The animal cardiac muscle potassium deficiency that can stop napelline to cause; During intravenous injection 10mg/kg, the animal atrial fibrillation that can stop electricity irritation to cause.There is strong anti-microbial activity purity to reach more than 98% to staphylococcus.
160～161 ° of allocryptopine fusing points.Be dissolved in ethanol, chloroform, ether, vinyl acetic monomer and diluted acid.Its molecular formula of prism-shaped crystallization (vinyl acetic monomer) C21H23NO5, molecular weight 369.40, structural formula:
Pink Plumepoppy Herb (Macleaya cordata (Willd.) R.Br.) is the perennial tall and big herbaceous plant of papaveracease Macleaya, and the herbal document of putting down in writing Pink Plumepoppy Herb the earliest is a supplement to the Herbal.Pink Plumepoppy Herb has another name called horn grass, horn bar, paulownia bar, suddenly reins in back, the big tube in mountain, yellow peppermint, yellow young married woman, SANQIANSAN, wild flax, Twig and leaf of Taperleaf Japanese Spiraea, now unified called after Pink Plumepoppy Herb is widely used in medicine, biological pesticide, animal doctor's veterinary drug, fine chemical product raw material.Be rich in multiple alkaloid in Pink Plumepoppy Herb fruit pod and the herb thereof, mainly contain sanguinarine(e) (Sanguinarine), white chelerythrine (Chelerythrine), protopine (Protopine) and allocryptopine alkaloids such as (Allocryptopine) in its extract (total alkaloids).Modern pharmacological research shows that allocryptopine has antiarrhythmic effect, and it suppresses effect greater than cigarette amine the animal irregular pulse that napelline is caused, and the animal cardiac muscle potassium deficiency that can stop napelline to cause; Staphylococcus there is strong anti-microbial activity; Protect the liver, protect important pharmacologically actives such as liver simultaneously in addition.
Extraction and the application of but studying sanguinarine(e), white chelerythrine and protopine and total alkali thereof mostly about the application document and the patent of Macleaya cordata alkaloids both at home and abroad at present, and the research data of relevant allocryptopine is less.This is main because allocryptopine content is lower and extract difficulty, thus pharmacology, the drug effect applied research of allocryptopine brought great limitation, so the research of industrial separation and preparation allocryptopine just becomes a problem demanding prompt solution.
Domestic patent CN 1532197A has also related to the separating of protopine and allocryptopine simultaneously at the isolating sanguinarine(e) of research macroporous resin with white chelerythrine, but this law can only the enrichment protopine and the mixture of allocryptopine, does not reach the monomeric purpose of separation and purification allocryptopine.Document " research of effective constituent in the Pink Plumepoppy Herb the fruit " (wall of Hu etc., " Acta Pharmaceutica Sinica " 1979,14 (9), 535-539) separate the monomer that sanguinarine(e) and white chelerythrine have also obtained allocryptopine simultaneously by silicagel column, but cost height, productive rate is low, only adapts to produced in small quantities, is not suitable for suitability for industrialized production.By retrieval, the patent documentation report that does not still have the monomeric industrial process of preparation allocryptopine at home and abroad.
Summary of the invention
The object of the present invention is to provide a kind of can be from natural phant (as bloodroots such as Pink Plumepoppy Herb, snowpoppy) extraction separation high-content allocryptopine monomer methods, this method technology is simple, be easy to purifying, the extraction yield height, equipment requirements is low, is that a kind of high-purity allocryptopine of suitable suitability for industrialized production extracts the preparation method.
To achieve these goals, the technical solution used in the present invention comprises following steps:
Obtain original extract with ethanol refluxing extraction, evaporate to dryness from natural bloodroot, original extract is settled out most of alkaloid (polarity bigger water-soluble alkaloid except) again in acid alcohol, adjust the pH value of filtrate to 7.5-8.5 with sig water, transfer PH to 9.5-10.5 after the filtration again, again filter, the filter residue after the filtration is a crude extract; Crude extract is successively handled with ethyl acetate, methanol eddy again, filtered, the recrystallization in methyl alcohol or chloroform-methanol or dehydrated alcohol of the residue behind the filtrate decompression evaporate to dryness can obtain high-content allocryptopine monomer.
After refluxing extraction 2-3 time (most preferably being 2 times), with the ammoniacal liquor alkalization, evaporated under reduced pressure obtains original extract to the ethanol that the present invention preferably uses 70%-85% from natural bloodroot.
Described original extract precipitates in acid alcohol and is meant original extract behind the dissolve with ethanol of 90-98%, precipitates behind the adding vitriol oil.
Described natural bloodroot is preferably Pink Plumepoppy Herb, snowpoppy.
Adjust the pH value of filtrate with the NaOH liquid of 5%-15%; PH value most preferably is 8.Use 10%-25%NaOH after the filtration again; Transfer pH value; Most preferred PH is 10.
Crude extract is used methanol eddy 2-3 time (most preferably being 2 times) again with ethyl acetate backflow 2-3 time (most preferably being 2 times), residue.
The concrete preparation process of the present invention is:
(1) crude extract of allocryptopine preparation
Get Pink Plumepoppy Herb fruit pod (root or stem also can), the preliminary pulverizing.With 80% alcohol reflux 2 times, the ammoniacal liquor alkalization, evaporated under reduced pressure, after residue dissolves again with 95% ethanol, add the vitriol oil, after the filtration, filtrate is diluted with 4 times of water, transfer about PH to 8 with 10%NaOH, filter rear filtrate and transfer PH to 10 with 20%NaOH again, the filter residue after the filtration is the crude extract (content is 25%-35%) of allocryptopine.
(2) purifying of the crude extract of allocryptopine
The allocryptopine crude extract of above-mentioned content is refluxed 2 times with ethyl acetate, residue is used methanol eddy 2 times again, filtrate decompression evaporate to dryness, dissolving back insulation crystallization in dehydrated alcohol again, its crystal again in dehydrated alcohol recrystallization once can get the crystal of content greater than the allocryptopine more than 85%.Continue recrystallization, can obtain the high-purity allocryptopine monomer after the drying.
Advantage of the present invention:
1. cost is lower, is easy to purifying.The present invention is a raw material with the powder of Pink Plumepoppy Herb fruit pod (root or stem), most non-alkaloid and the rudimentary property of part alkaloid have been removed with alcohol extracting, acid mode heavy, alkalization again, again by the backflow of ethyl acetate removed most of easily with the protopine of allocryptopine formation co-precipitation, further improved the content of allocryptopine by the backflow of methyl alcohol.The solvent that the present invention uses is low toxicity, organic solvent at a low price, and is all recyclable, little to environmental influence, low for equipment requirements, can need not column separation process, and direct crystallization can obtain high-purity allocryptopine.This law application prospect is good, meets the recycling economy requirement.
2. technology is simple, environmental friendliness.The present invention does not need to use complicated separation and purification equipment, and technical process is simple and reliable, and is easy to operate, and energy consumption is lower.The allocryptopine of this law separation and purification is former to be waste in the Pink Plumepoppy Herb total alkali production process, because it has bacteriostatic action, so be difficult for degrading, directly discharges the after stain environment; And the enforcement of this law has not only reached and has turned waste into wealth, and increases the purpose of the output value, and has further improved the utilization ratio of Pink Plumepoppy Herb resource, has reduced the detrimentally affect of Pink Plumepoppy Herb product development to environment.
In sum, the present invention has enlarged the raw material scope of selecting material that extracts allocryptopine effectively, provides a kind of economy, feasible novel method for preparing highly purified allocryptopine monomer.The inventive method is drawn materials conveniently, and isolation and purification is simple for process, cost is lower, is suitable for producing in enormous quantities.
Description of drawings
The high-efficient liquid phase chromatogram of the HPLC-ESI-MS of Fig. 1 allocryptopine (purity＞88%).Fig. 2 is ESI-MS figure.
Embodiment
The present invention has carried out HPLC-ESI-MS mensuration to separating the allocryptopine (purity＞88%) that obtains in following examples, and analysis condition is: liquid chromatography: WATERS UPLC
TMMass spectrum: WATERSPremier XE
Analysis condition:
Moving phase: organic phase is an acetonitrile, and water adds 0.1% formic acid for the 30mmol/L Ammoniom-Acetate.
Chromatographic column: the special Kromasil C-18 of Dalian Erie, (5 μ m, 4.6mm i.d., 250mm)
Workstation; MassLynx V4.1
Mass spectrum condition (positive ion mode):
capillary?voltage，3.0kV；cone?voltage，25V；extractor，4V，Desolvation?gasflow?15L/min；source?temperature，120℃；desolvation?gas?temperature，350℃.
The evaluation of allocryptopine:
The allocryptopine molecular formula is C
21H
23NO
5, clear crystal (crystallization in the ethyl acetate), 162～165 ℃ of fusing points, the improvement bismuth potassium iodide shows the red-brown spot.Allocryptopine has α and two kinds of crystal formations of β, belongs to the physical isomerism body, and fusing point is slightly variant, but pharmacologically active and indifference, so the present invention does not add difference to this.
The micro-fusing point instrument of melting point detector: XT4 (not proofreading and correct); Nuclear magnetic resonance analyser: INOVA-400, TMS are interior mark.
1HNMR(CDCl
3400MHz)δ：6.957(1H，s，H-8)，6.926(1H，d，J＝8.4Hz，H-14)，6.906(1H，d，J＝8.1Hz，H-13)，6.638(1H，s，H-5)，5.947(2H，s，-OCH
2O-)，3.858(3H，s，15-OCH
3)，3.781(3H，s，16-OCH
3)，3.609(2H，s，H-18)，3.322-3.460(2H，m，H-2)，3.452-2.783(2H，m，H-3)，1.912(2H，s，H-11)，1.872(3H，s，N-CH
3)；
13CNMR(CDCl
3100MHz)δ：57.7(C-2)，32.272(C-3)，135.872(C-4)，109.217(C-5)，148.017(C-6)，146.033(C-7)，110.590(C-8)，132.744(C-9)，192.812(C-10)，46.157(C-11)，129.456(C-12)，127.663(C-13)，110.590(C-14)，147.323(C-15)，151.549(C-16)，128.456(C-17)，50.208(C-18)，41.213(N-CH
3)，101.168(-OCH
2O-)，60.751(-OCH
3)，55.619(-OCH
3)。Spectroscopic data determines that it is allocryptopine through contrasting with document.
The present invention is described further in conjunction with concrete preparation embodiment
Pink Plumepoppy Herb fruit pod 500g, 55 ℃ of oven dry down, be crushed to 50 orders, measure 60% industrial alcohol refluxing extraction 2 times with 8 times, each 1 hour, ammoniacal liquor alkalization, evaporated under reduced pressure, after residue dissolves again with 85% industrial alcohol, add the vitriol oil, after the heavy liquid of acid filters, dilute with 8 times of water behind the filtrate decompression evaporate to dryness, transfer about PH to 8 with 10%NaOH again, filter rear filtrate and transfer PH to 10 with 20%NaOH again, the filter residue after the filtration refluxes 2 times with ethyl acetate, each 1 hour, residue is used methanol eddy 2 times again, each 2 hours.The filtrate decompression evaporate to dryness, dissolving back insulation crystallization 4 hours in dehydrated alcohol again, its crystal is recrystallization 12 hours in dehydrated alcohol again, nearly colourless prism-shaped crystal, can obtain purity behind the Air drying and be 88% allocryptopine monomer, yield 0.53%.
Root of Herba Macleayae Cordatae 2kg, 60 ℃ of oven dry down, be crushed to 10 orders, measure 50% industrial methanol refluxing extraction 2 times with 10 times, ammoniacal liquor alkalization in each 1.5 hours, after evaporated under reduced pressure, residue are dissolved again with 75% industrial alcohol, add the vitriol oil, after the heavy liquid of acid filters, with 6 times of water dilutions, transfer about PH to 8 with 10%NaOH again behind the filtrate decompression evaporate to dryness, filter rear filtrate and transfer PH to 10 with 20%NaOH again, filter residue after the filtration refluxes 2 times with ethyl acetate, each 1 hour, residue was used methanol eddy 2 times again, each 2 hours.The filtrate decompression evaporate to dryness, dissolving back insulation crystallization 6 hours in dehydrated alcohol again, its crystal is recrystallization 10 hours in chloroform-methanol again, nearly colourless prism-shaped crystal, can obtain purity behind the Air drying and be 84% allocryptopine monomer, yield 0.68%.
Pink Plumepoppy Herb stem 2kg, 55 ℃ of oven dry down, be crushed to 30 orders, measure 75% industrial methanol refluxing extraction 2 times with 6 times, each 1 hour, ammoniacal liquor alkalization, evaporated under reduced pressure, after residue dissolves again with 80% industrial alcohol, add the vitriol oil, after the heavy liquid of acid filters, dilute with 8 times of water behind the filtrate decompression evaporate to dryness, transfer about PH to 8 with 10%NaOH again, filter rear filtrate and transfer PH to 10 with 20%NaOH again, the filter residue after the filtration refluxes 2 times with ethyl acetate, each 1 hour, residue is used methanol eddy 2 times again, each 1 hour.The filtrate decompression evaporate to dryness, dissolving back insulation crystallization 4 hours in methyl alcohol again, its crystal is recrystallization 12 hours in methyl alcohol again, nearly colourless prism-shaped crystal, can obtain purity behind the Air drying and be 80% allocryptopine monomer, yield 0.45%.
Embodiment 4
Pink Plumepoppy Herb fruit pod 1kg 60 ℃ of oven dry down, is crushed to 50 orders, measures 80% industrial alcohol (containing 0.5% sulfuric acid) cold soakings 2 times with 15 times, and each 48 hours, it was 8 that ammoniacal liquor is basified to pH value, evaporated under reduced pressure.After residue dissolves again with 95% industrial alcohol, add the vitriol oil, after the heavy liquid of acid filters, dilute with 6 times of water again behind the filtrate decompression evaporate to dryness, ammoniacal liquor is transferred about PH to 8, and after the filtration, filtrate is transferred PH to 10 with 20%NaOH again, filter once more, filter residue after the filter refluxes 2 times with ethyl acetate, and each 1 hour, after the filtration, residue is used methanol eddy 2 times again, each 1 hour.The filtrate filtered evaporated under reduced pressure, residue dissolves in methyl alcohol again, insulation crystallization 6 hours, its crystal is recrystallization 10 hours in chloroform-methanol again, nearly colourless prism-shaped crystal, can obtain purity behind the Air drying and be 82% allocryptopine monomer, yield 0.72%.
Embodiment 5
Snowpoppy herb 5kg 60 ℃ of down oven dry, is crushed to 50 orders, measures 80% industrial alcohol (containing 0.5% sulfuric acid) cold soakings 2 times with 15 times, and each 48 hours, it was 8 that ammoniacal liquor is basified to pH value, evaporated under reduced pressure.After residue dissolves again with 95% industrial alcohol, add the vitriol oil, after the heavy liquid of acid filters, dilute with 6 times of water again behind the filtrate decompression evaporate to dryness, ammoniacal liquor is transferred about PH to 8, and after the filtration, filtrate is transferred PH to 10 with 20%NaOH again, filter once more, filter residue after the filter refluxes 2 times with ethyl acetate, and each 1 hour, after the filtration, residue is used methanol eddy 2 times again, each 1 hour.The filtrate filtered evaporated under reduced pressure, residue dissolves in methyl alcohol again, insulation crystallization 6 hours, its crystal is recrystallization 10 hours in chloroform-methanol again, nearly colourless prism-shaped crystal, can obtain purity behind the Air drying and be 85% allocryptopine monomer, yield 0.25%.
Embodiment 5
Pilewort herb 5kg 60 ℃ of down oven dry, is crushed to 50 orders, measures 80% industrial alcohol (containing 0.5% sulfuric acid) cold soakings 2 times with 15 times, and each 48 hours, it was 8 that ammoniacal liquor is basified to pH value, evaporated under reduced pressure.After residue dissolves again with 95% industrial alcohol, add the vitriol oil, after the heavy liquid of acid filters, dilute with 6 times of water again behind the filtrate decompression evaporate to dryness, ammoniacal liquor is transferred about PH to 8, and after the filtration, filtrate is transferred PH to 10 with 20%NaOH again, filter once more, filter residue after the filter refluxes 2 times with ethyl acetate, and each 1 hour, after the filtration, residue is used methanol eddy 2 times again, each 1 hour.The filtrate filtered evaporated under reduced pressure, residue dissolves in methyl alcohol again, insulation crystallization 6 hours, its crystal is recrystallization 10 hours in chloroform-methanol again, nearly colourless prism-shaped crystal, can obtain purity behind the Air drying and be 83% allocryptopine monomer, yield 0.30%.
Embodiment 6
Corydalis tuber 5kg 60 ℃ of down oven dry, is crushed to 50 orders, measures 80% industrial alcohol (containing 0.5% sulfuric acid) cold soakings 2 times with 15 times, and each 48 hours, it was 8 that ammoniacal liquor is basified to pH value, evaporated under reduced pressure.After residue dissolves again with 95% industrial alcohol, add the vitriol oil, after the heavy liquid of acid filters, dilute with 6 times of water again behind the filtrate decompression evaporate to dryness, ammoniacal liquor is transferred about PH to 8, and after the filtration, filtrate is transferred PH to 10 with 20%NaOH again, filter once more, filter residue after the filter refluxes 2 times with ethyl acetate, and each 1 hour, after the filtration, residue is used methanol eddy 2 times again, each 1 hour.The filtrate filtered evaporated under reduced pressure, residue dissolves in methyl alcohol again, insulation crystallization 6 hours, its crystal is recrystallization 10 hours in chloroform-methanol again, nearly colourless prism-shaped crystal, can obtain purity behind the Air drying and be 84% allocryptopine monomer, yield 0.56%.
Need not further detailed description, believe and adopt the disclosed content in front, one of skill in the art can use the present invention to greatest extent.Therefore, the embodiment of front is interpreted as only illustrating, but not limits range of application of the present invention by any way.
Claims (8)
1. extracting method for preparing high-purity allocryptopine, it is characterized in that, obtain original extract with ethanol refluxing extraction, evaporate to dryness from natural bloodroot, original extract is settled out most of alkaloid again in acid alcohol, adjust pH value of filtrate to 7.5-8.5 with sig water, transfer pH to 9.5-10.5 after the filtration again, filter again, the filter residue after the filtration is a crude extract; Crude extract is successively handled with vinyl acetic monomer, methanol eddy again, filtered, the recrystallization in methyl alcohol or chloroform-methanol or dehydrated alcohol of the residue behind the filtrate decompression evaporate to dryness can obtain the high-purity allocryptopine monomer.
2. a kind of extracting method for preparing high-purity allocryptopine according to claim 1 is characterized in that, after refluxing extraction 2-3 time, alkalizes with ammoniacal liquor from natural bloodroot with the ethanol of 70%-85%, and evaporated under reduced pressure obtains original extract.
3. a kind of extracting method for preparing high-purity allocryptopine according to claim 2 is characterized in that, described original extract precipitates in acid alcohol and is meant original extract behind the dissolve with ethanol of 90%-98%, precipitates behind the adding vitriol oil.
4. a kind of extracting method for preparing high-purity allocryptopine according to claim 2 is characterized in that described natural bloodroot is Pink Plumepoppy Herb or snowpoppy.
5. according to claim 1 or 2 or 3 described a kind of extracting method that prepare high-purity allocryptopine, it is characterized in that, adjust pH value of filtrate to 7.5-8.5 with the NaOH liquid of 5%-15%.
6. a kind of extracting method for preparing high-purity allocryptopine according to claim 5 is characterized in that, the pH value is after the filtrate of 7.5-8.5 is filtered, to use the 10%-25%NaOH adjust pH to 9.5-10.5 again.
7. according to claim 1 or 2 or 3 described a kind of extracting method that prepare high-purity allocryptopine, it is characterized in that crude extract is used methanol eddy 2-3 time again with vinyl acetic monomer backflow 2-3 time, residue.
8. a kind of extracting method for preparing high-purity allocryptopine according to claim 1 is characterized in that, may further comprise the steps the crude extract preparation of (1) allocryptopine: get Pink Plumepoppy Herb fruit pod, root of Herba Macleayae Cordatae or Pink Plumepoppy Herb stem, the preliminary pulverizing; With 80% alcohol reflux 2 times, the ammoniacal liquor alkalization, evaporated under reduced pressure, after residue dissolves again with 95% ethanol, add the vitriol oil, after the filtration, filtrate is diluted with 4 times of water, transfer about pH to 8 with 10%NaOH, filter rear filtrate and transfer pH to 10 with 20%NaOH again, the filter residue after the filtration is the crude extract of allocryptopine;
(2) purifying of the crude extract of allocryptopine: the allocryptopine crude extract of above-mentioned content is refluxed 2 times with vinyl acetic monomer, residue is used methanol eddy 2 times again, the filtrate decompression evaporate to dryness, dissolving back insulation crystallization in dehydrated alcohol again, its crystal again in dehydrated alcohol recrystallization once can get the crystal of content greater than 85% allocryptopine; Continue recrystallization, can obtain the high-purity allocryptopine monomer after the drying.
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Non-Patent Citations (6)
| Title |
|---|
| FRANK R . STERMITZ et al.Alkaloids of the Papaveraceae V.Muramine and Berberine from Argemone squarrosa.《Journal of Pharmaceutical Sciences》.1967,第56卷(第6期),760-762. |
| FRANK R . STERMITZ et al.Alkaloids of the Papaveraceae V.Muramine and Berberine from Argemone squarrosa.《Journal of Pharmaceutical Sciences》.1967,第56卷(第6期),760-762. * |
| FRANK R.STERMITZ et al.Alkaloids of the Papaveraceae VI. Protopine and Allocryptopine from Arctomecon californica.《Journal of Pharmaceutical Sciences》.1967,第56卷(第6期),762. |
| FRANK R.STERMITZ et al.Alkaloids of the Papaveraceae VI. Protopine and Allocryptopine from Arctomecon californica.《Journal of Pharmaceutical Sciences》.1967,第56卷(第6期),762. * |
| K.Iwasa et al.PROTOPINE-N-OXIDE,AN ALKALOID FROM BOCCONIA CORDATA.《Phytochemistry》.1983,第22卷(第2期),627-628. * |
| K.Iwasaetal.PROTOPINE-N-OXIDE AN ALKALOID FROM BOCCONIA CORDATA.《Phytochemistry》.1983 |
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