CN1317282C - Method for extracting protopine from decumbent corydalis tuber - Google Patents
Method for extracting protopine from decumbent corydalis tuber Download PDFInfo
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Abstract
The present invention discloses a method for extracting alkaloid (macleyine) from traditional Chinese medicine (corydalis), which comprises the following steps: (1) a medicinal material (corydalis)is heated and extracted in 85 to 100% ethanol and the extraction liquid is concentrated; (2) the ethanol in the concentrated extraction liquid is recovered, and hydrochloric acid of which the concentration is from 0.5 to 15% is added to residual liquid to stand still; (3) insoluble substances in the hydrochloric acid of step (2) are filtered off, filtered liquid is neutralized by strongly alkaline solution of which the concentration is from 1 to 30%, and an alkaloid precipitate a is obtained; (4) 0.5 to 15% hydrochloric acid and 85 to 100% ethanol are added to the alkaloid precipitate a, insoluble substances are filtered off, and filtered liquid is neutralized by 1 to 30% strongly alkaline solution to obtain an alkaloid precipitate b; then the alkaloid precipitate b is washed and dried to obtain solids; (5) the solids is crystallized. By the method of the present invention, the yield of macleyine obtained by extraction is more than 0.24% of that of a crude medicinal material (corydalis), and the purity is more than 99.5%. Compared with the prior art, the present invention has the advantages of little pollution, low time consumption, low cost, high yield, high purity and low energy consumption.
Description
Technical field
The present invention relates to from Rhizome of Decumbent Corydalis, extract the method for alkaloid protopine (Protopine).
Background technology
Rhizome of Decumbent Corydalis is the dry tuber of papaveracease, Corydalis, corydalis amabilis Migo [Corydalis decumbens (Thunb) Pers. (Corydalis amabilis Migo)], be used for the treatment of rheumatic arthritis, lumbar muscle strain, the hemiplegia that cerebrovascular accident causes, has the antispastic pain relieving, the effect of promoting blood circulation and removing blood stasis and step-down promoting the circulation of qi.The researchist finds to contain the alkali-free in summer in the Rhizome of Decumbent Corydalis, corydalis rice is decided the alkaloid of alkali, kinds more than 30 such as complete withered clever alkali, Tetrahydropalmatine and protopine.Wherein, protopine (Protopine) has choline esterase inhibition, and has non-selective ionic channel retardation, can be used for treating Alzheimer's disease, is a kind of potential candidate medicine of presenile dementia.If from natural product, extract this compound, a kind of simple, economy of then can yet be regarded as and efficient manner.Protopine (Protopine) chemistry is by name: 7-methyl-2, and 3:9,10-bis (methlenedioxy)-7,13a-secoberbin-13a-one, its chemical structure is as follows:
The document of separating bio total alkali is more from Rhizome of Decumbent Corydalis, but the document of separation protopine is less, and the protopine productive rate of gained generally is no more than 0.1%.As patent CN1445227A (extracting method of total alkaloid of corydalis rhizome and new purposes thereof, application number 02111103.0): decumbent corydalis as medicine material decoction liquor in dilute hydrochloric acid is crossed macroporous adsorbent resin, washing back ethanol elution; Ethanol eluate peroxidation alumina gel post then, under alkaline condition, is separated out biology total alkali.Because the hydrochloride of the alkaloid Tetrahydropalmatine in the Rhizome of Decumbent Corydalis, solubleness is very little in water, thereby is unfavorable for the separation of protopine; In addition, because the decoction of hydrochloric acid produces a large amount of impurity, protopine can not extract from medicinal material effectively as a result.
Summary of the invention
The inventor concentrates on studies to the extraction of protopine, filters out the method for preferably extracting protopine from Rhizome of Decumbent Corydalis, has finished the present invention thus.
So the technical problem to be solved in the present invention promptly is the defective that overcomes above-mentioned prior art, provide a kind of method of from Rhizome of Decumbent Corydalis, extracting protopine.
Above-mentioned technical problem of the present invention realizes by following technical proposal:
A kind of method of from Rhizome of Decumbent Corydalis, extracting protopine, it may further comprise the steps:
(1) decumbent corydalis as medicine material heat in 85～100% ethanol is carried concentrated extracting solution;
(2) ethanol in spissated extracting solution in the recycling step (1), adding concentration is 0.5～15% hydrochloric acid in residual liquid, places hydrochloric acid insoluble substance is fully separated out;
(3) with the hydrochloric acid insoluble substance elimination in the step (2), filtrate is the neutralization of 1～30% strong base solution with concentration, alkaloid precipitation a;
(4) add 0.5～15% hydrochloric acid and 85～100% ethanol among the alkaloid that in step (3), the obtains precipitation a, the elimination insolubles, filtrate neutralize with 1～30% strong base solution, again alkaloid precipitates b, washing also, drying obtains solids;
(5) solids that obtains in the step (4) is carried out crystallization, promptly get the protopine crystal;
Wherein, Rhizome of Decumbent Corydalis and alcoholic acid ratio are generally the 1kg medicinal material in the step (1): 5～50L ethanol, said heat are carried and generally are meant refluxing extraction, and corresponding temperature is 78～85 ℃; Its extraction time can be 1～5 time, and each extraction time can be 1.5～5 hours, when multiple extraction, obviously also can extract at direct heating under the said temperature, and each extracting solution is merged reconcentration.
As in residual liquid, adding hydrochloric acid in the step (2), be preferably, to pH be 0.5～2, place and hydrochloric acid insoluble substance fully separated out in 10～24 hours; Wherein, pH is too low, as approaches 0, though hydrochloric acid insoluble substance is separated out soon, it is big to add hydrochloric acid content, and operational risk big (strong acid environment), pH be higher than 2 then hydrochloric acid insoluble substance separate out slowly and be abundant inadequately; Can not fully separate out as for too short then hydrochloric acid insoluble substance of time, otherwise the time is long more, though separate out fully, has prolonged the production cycle.
And step (3) in filtrate neutralize with strong base solution, be preferably, to pH be 10～12; Wherein, pH is too high, as approaches 14, and it is big then need to strengthen alkali number, and operational risk big (strong alkali environment), and pH is lower than 10, and then precipitation is complete inadequately.
In like manner, in alkaloid precipitation a, add hydrochloric acid and ethanol in the step (4), be preferably, to pH be 0.5～3, and filtrate neutralizes with strong base solution, is preferably, to pH be 8～12, thereby make alkaloid precipitation b.This alkaloid precipitation b carries out conventional washing with after removing impurity and excessive strong base solution, carries out drying again and obtains the white solid thing.
And can adopt in chloroform, methyl alcohol, ethanol, ether and the acetone and other organic solvent one or more to carry out crystallization in the step (5), as can in 60 ℃ white solid being dissolved in the above-mentioned solvent according to a conventional method, be cooled to room temperature; Further recrystallization also, colourless protopine crystal, 203～204 ℃ of fusing points are made mixed melting point with reference substance and are measured and also do not descend.
Be preferably, this organic solvent is the chloroform and the methyl alcohol of volume ratio 1: 1～2.
According to the present invention, above-mentioned concentration of hydrochloric acid is preferably 3～12%; More preferably be 8～10%.
And above-mentioned strong base solution can be solution such as sodium hydroxide or potassium hydroxide, and its concentration is preferably 5～20%; More preferably be 9～15%.
And ethanolic soln concentration is preferably 88～98%; More preferably be 90～95%.
The present invention extracts in the method for protopine from Rhizome of Decumbent Corydalis, step (2)～4), be about to that alkaloid is dissolved in hydrochloric acid or the highly basic and the time temperature condition be preferably 0 ℃～50 ℃, normally do not need can reduce the loss of protopine under extra heating and the refrigerative room temperature.
Compared with prior art, the present invention has tangible advantage: (1) pollutes few: as Wang Zhaoquan in 1977 the 8th phases of herbal medicine communication the 13rd page of extracting method of being reported, the benzene that adopts strong toxicity is as solvent, solvent of the present invention, all can reclaim effectively and reuse, therefore reduce when polluting also reducing cost; (2) time spent is short: the present invention did not need post, and the solvent total amount is low, and step is few; (3) cost is low: equipment of the present invention, be conventional equipment, and solvent can be applied mechanically, and it is low to consume energy; (4) yield height: adopt method of the present invention, extract safety; Extract from tame Rhizome of Decumbent Corydalis, the content that residues in protopine in medicinal material and the other biological alkali is extremely low, and the yield of crystal protopine obviously improves, and accounting for the crude drug amount can be greater than 0.24% (W/W); (5) purity height: through efficient liquid phase chromatographic analysis, its purity also significantly improves, mostly more than 99.5%; (6) power consumption is low: the solvent total amount of use is low, and the aqueous solution that relates to need not heat and cooling.
Embodiment
Further specify the present invention below by embodiment.It should be understood that embodiments of the invention are to be used to illustrate the present invention rather than limitation of the present invention.Essence according to the present invention all belongs to the scope of protection of present invention to the simple modifications that the present invention carries out.In addition, in the present invention, concentration of ethanol per-cent is volume percent; All the other reagent concentration per-cents are weight percentage.
Wherein, the crystal that makes among each embodiment is identified and mensuration content through high efficiency liquid phase chromatographic analysis method, and is specific as follows:
1, TLC identifies: add quadrol through chloroform; Acetone adds quadrol; Sherwood oil, ether, methyl alcohol and ammoniacal liquor; Multiple developping agent is identified, separates the protopine crystal and the protopine reference substance that obtain, and its Rf value is identical.
2, the HPLC assay (Gu Xiaohong, Tang Ping, Jin Zuying. the content of protopine in the rp-hplc determination Rhizome of Decumbent Corydalis. the time precious traditional Chinese medical science traditional Chinese medicines, 2002,13 (10): 608-609):
Chromatographic instrument: Tianjin, island SHIMADZU:SPD-10A, LC-10AD, C-R8A
Wavelength 282nm; Moving phase: acetonitrile: methyl alcohol: 0.2% phosphoric acid=150: 100: 750, diethylamine is transferred pH=3
Chromatographic column: Shim Pack-CLC-ODS
Flow velocity: 1ml/ minute
Sample concentration: 3.35mg/ml
Temperature: 20 ℃
Above-mentioned reference substance protopine: purchase in Nat'l Pharmaceutical ﹠ Biological Products Control Institute.
Embodiment 1
Take by weighing 8 kilograms of clean Rhizome of Decumbent Corydalis, place the extraction still of 100L, add 40L 85% ethanol, be heated to 80 ℃, 2 hours, extracting solution is leached through gauze, filter residue stays in extracting still, adds 40L85% ethanol again, continues heat and carries 2 hours, and twice filtrate merges; Reclaim (promptly concentrating) ethanol wherein, get residual liquid 10L.In above-mentioned residual liquid, add 10L 5% hydrochloric acid to pH be 2, placed 10 hours; The elimination hydrochloric acid insoluble substance, filtrate is with getting alkaloid precipitation a with pH=12 in 15% the aqueous sodium hydroxide solution; Alkaloid is precipitated a be dissolved in 5L 5% hydrochloric acid, add 85% ethanol 500ml simultaneously, making pH value of solution is 3, the new precipitation that produces of elimination; Filtrate neutralizes with 15% aqueous sodium hydroxide solution, and pH=12 gets alkaloid precipitation b, should precipitate b to pH=8 with distilled water wash, the dry white solid thing that gets; This solid gets the water white transparency protopine crystal 19.27g of content 99.65% through chloroform and methyl alcohol (volume ratio is 1: 1) crystallization and recrystallization.
Embodiment 2
Take by weighing 10 kilograms of clean Rhizome of Decumbent Corydalis, place the extraction still of 100L, add 50L 95% ethanol, be heated to 80 ℃, 2 hours, leach through gauze, filter residue stays in extracting still, adds 50L 95% ethanol, continues heat and carries, and twice filtrate merges; Reclaim ethanol, residual liquid 11L, in above-mentioned residual liquid, add 10L 10% hydrochloric acid to pH be 1.5, placed 12 hours; The elimination hydrochloric acid insoluble substance, filtrate is with getting alkaloid precipitation a with pH=11 in 10% the aqueous sodium hydroxide solution; Alkaloid is precipitated a be dissolved in 5L 10% hydrochloric acid, add 95% ethanol 500ml simultaneously, making pH value of solution is 1, the new precipitation that produces of elimination; Filtrate neutralizes with 10% aqueous sodium hydroxide solution, and pH=10 gets alkaloid precipitation b, should precipitate b to pH=8 with distilled water wash, the dry white solid that gets; This solid gets the protopine 24.11g of content 99.73% through chloroform and methyl alcohol (volume ratio is 1: 1) crystallization and recrystallization.
Embodiment 3
Take by weighing 1 kilogram of round-bottomed flask that places 10L of clean Rhizome of Decumbent Corydalis, add 6L 90% ethanol, be heated to 85 ℃, backflow 2h, inclining supernatant liquor, and the dregs of a decoction stay in round-bottomed flask, again add 6L 90% ethanol, continue heat and carry 2h, merge above-mentioned solution and concentrated twice; Reclaim ethanol, get residual liquid 1L, in above-mentioned residual liquid, add 3% hydrochloric acid, placed 20 hours to pH=1; The elimination insolubles, filtrate is with getting alkaloid precipitation a with pH=11 in 30% the aqueous sodium hydroxide solution; Alkaloid is precipitated a with 0.5L 10% dissolving with hydrochloric acid, add 95% ethanol 80ml simultaneously, making pH value of solution is 1, the new precipitation that produces of elimination; Filtrate neutralizes with 20% aqueous sodium hydroxide solution, and pH=9 gets alkaloid precipitation b, should precipitate b to pH=8 with distilled water wash, the dry white solid that gets; This solid gets the protopine 1.89g of content 99.54% through chloroform and methyl alcohol (volume ratio is 1: 2) crystallization and recrystallization.
Embodiment 4
Take by weighing 1.2 kilograms of round-bottomed flasks that place 10L of clean Rhizome of Decumbent Corydalis, add 6L 98% ethanol, be heated to 85 ℃, backflow 1.5h, inclining supernatant liquor, and the dregs of a decoction stay in round-bottomed flask, again add 6L 98% (V/V) ethanol, continue heat and carry 1.5h, merge above-mentioned solution and concentrated twice; Reclaim ethanol, get residual liquid 1.2L, in above-mentioned residual liquid, add 8% hydrochloric acid, placed the elimination insolubles 24 hours to pH=1.5; Filtrate is with getting alkaloid precipitation a with pH=10 in 5% the aqueous sodium hydroxide solution; Alkaloid is precipitated a with 0.4L 15% dissolving with hydrochloric acid, and adding 90% ethanol 80ml simultaneously, to make pH value of solution be 0.5, the new precipitation that produces of elimination; Filtrate neutralizes with 15% aqueous sodium hydroxide solution, and pH=8.5 gets alkaloid precipitation b, should precipitate b to pH=8 with distilled water wash, the dry white solid that gets; This solid gets the protopine 2.86g of content 99.67% through chloroform and methyl alcohol (volume ratio is 1: 2) crystallization and recrystallization.
Embodiment 5
Take by weighing 5 kilograms of clean Rhizome of Decumbent Corydalis and place the extraction still of 50L, add 25L 90% ethanol, be heated to 85 ℃, backflow 1.5h, inclining supernatant liquor, and the dregs of a decoction stay in extracting still, again add 25L 90% ethanol, continue heat and carry 1.5h, merge above-mentioned solution and concentrated 2 times; Reclaim ethanol, get residual liquid 6L, in above-mentioned residual liquid, add 15% hydrochloric acid, placed the elimination insolubles 14 hours to pH=1; Filtrate neutralizes with 20% aqueous sodium hydroxide solution, and pH=12 gets alkaloid precipitation a; Alkaloid is precipitated a with 2.5L 10% dissolving with hydrochloric acid, and adding 95% ethanol 300ml simultaneously, to make pH value of solution be 2, the new precipitation that produces of elimination; Filtrate neutralizes with 20% aqueous sodium hydroxide solution, and pH=9 gets alkaloid precipitation b, should precipitate b to pH=8 with distilled water wash, the dry white solid that gets; This solid gets the protopine 12.10g of content 99.76% through chloroform and methyl alcohol (volume ratio is 1: 2) crystallization and recrystallization.
Embodiment 6
Take by weighing 1 kilogram of clean Rhizome of Decumbent Corydalis and place the extraction still of 100L, add the 50L dehydrated alcohol, be heated to 78 ℃, 5 hours, leach through gauze, collect filtrate; Reclaim ethanol, get residual liquid 1L, in above-mentioned residual liquid, add 0.5% hydrochloric acid, placed the elimination insolubles 15 hours to pH=2; Filtrate neutralizes with 1% aqueous sodium hydroxide solution, and pH=10 gets alkaloid precipitation a; Alkaloid is precipitated a with 0.5L 3% dissolving with hydrochloric acid, and adding 98% ethanol 300ml simultaneously, to make pH value of solution be 3, the new precipitation that produces of elimination; Filtrate is with the neutralization of 5% aqueous sodium hydroxide solution, pH=8, alkaloid precipitation b, with distilled water wash removing impurity, dry must white solid; This solid gets the protopine 2.27g of content 99.5% through chloroform and ethanol (volume ratio is 1: 1) crystallization and recrystallization.
Embodiment 7
Take by weighing 6 kilograms of clean Rhizome of Decumbent Corydalis and place the extraction still of 50L, add 30L 85% ethanol, be heated to about 80 ℃ 3 hours, leach through gauze, filter residue stays in extracting still, adds 30L 85% ethanol again, continue heat and carry 1.5 hours, extract so repeatedly totally 5 times, merge all filtrates; Reclaim ethanol, get residual liquid 6L, in above-mentioned residual liquid, add 12% hydrochloric acid, placed the elimination insolubles 12 hours to pH=0.8; Filtrate neutralizes with 9% potassium hydroxide aqueous solution, and pH=10.5 gets alkaloid precipitation a; Alkaloid is precipitated a with 3L 15% dissolving with hydrochloric acid, and adding 88% ethanol 300ml simultaneously, to make pH value of solution be 1.5, the new precipitation that produces of elimination; Filtrate neutralizes with 30% potassium hydroxide aqueous solution, and pH=10 gets alkaloid precipitation b, should precipitate b to pH=8 with distilled water wash, the dry white solid that gets; This solid gets the protopine 14.48g of content 99.6% through ether crystallization and recrystallization.
Embodiment 8
Take by weighing 5 kilograms of clean Rhizome of Decumbent Corydalis and place the extraction still of 50L, add 25L 88% ethanol, be heated to 85 ℃, backflow 1.5h, inclining supernatant liquor, and the dregs of a decoction stay in extracting still, add 25L 88% ethanol again, continue heat and carry 1.5h, inclining supernatant liquor and repeats to extract 1 time again, merges 3 times above-mentioned solution; Reclaim ethanol, get residual liquid 5L, in above-mentioned residual liquid, add 15% hydrochloric acid, placed the elimination insolubles 14 hours to pH=0.5; Filtrate neutralizes with 20% aqueous sodium hydroxide solution, and pH=12 gets alkaloid precipitation a; Alkaloid is precipitated a with 2.5L 8% dissolving with hydrochloric acid, and adding 95% ethanol 300ml simultaneously, to make pH value of solution be 2, the new precipitation that produces of elimination; Filtrate neutralizes with 20% aqueous sodium hydroxide solution, and pH=9 gets alkaloid precipitation b, should precipitate b to pH=8 with distilled water wash, the dry white solid that gets; This solid gets the protopine 12.14g of content 99.7% through chloroform and acetone (volume ratio is 1: 1.5) crystallization.
Claims (9)
1, a kind of method of extracting protopine from Rhizome of Decumbent Corydalis is characterized in that this method may further comprise the steps:
(1) be that heat is carried concentrated extracting solution in 85～100% the ethanol with decumbent corydalis as medicine material in volume percent;
(2) ethanol in spissated extracting solution in the recycling step (1), the adding weight percent concentration is 0.5～15% hydrochloric acid in residual liquid, places hydrochloric acid insoluble substance is fully separated out;
(3) with the hydrochloric acid insoluble substance elimination in the step (2), filtrate is the neutralization of 1～30% strong base solution with weight percent concentration, alkaloid precipitation a;
(4) add weight percent among the alkaloid that in step (3), the obtains precipitation a and be 0.5～15% hydrochloric acid and volume percent and be 85～100% ethanol to pH be 0.5～3, the elimination insolubles, filtrate is that to be neutralized to pH be 8～12 to 1～30% strong base solution with weight percent, get alkaloid precipitation b again, washing and drying obtain solids;
(5) solids that obtains in the step (4) is carried out crystallization, promptly get the protopine crystal.
2, method according to claim 1, it is characterized in that middle Rhizome of Decumbent Corydalis of step (1) and alcoholic acid ratio are the 1kg medicinal material: 5～50L ethanol, said heat is carried and is meant under 78～85 ℃ of temperature and extracts or refluxing extraction, its extraction time is 1～5 time, and each extraction time is 1.5～5 hours.
3, method according to claim 1, it is characterized in that in the step (2) in residual liquid, adding hydrochloric acid to pH be 0.5～2, placed 10～24 hours.
4, method according to claim 1 is characterized in that it is 10～12 that the middle filtrate of step (3) is neutralized to pH with strong base solution.
5, method according to claim 1, it is characterized in that step (5) adopts organic solvent: one or more in chloroform, methyl alcohol, ethanol, ether and the acetone carry out crystallization.
6, method according to claim 5 is characterized in that this organic solvent is the chloroform and the methyl alcohol of volume ratio 1: 1～2.
7, method according to claim 1 is characterized in that this volumes of aqueous ethanol percentage concentration is 90～95%.
8, method according to claim 1 is characterized in that this hydrochloric acid weight percent concentration is 3～12%.
9, according to the described method of the arbitrary claim of claim 1～8, it is characterized in that this strong base solution is sodium hydroxide or potassium hydroxide, its weight percent concentration is 5～20%.
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101054377B (en) * | 2006-04-13 | 2010-05-12 | 上海医药工业研究院 | Total alkaloids extraction of corydalis, its preparation method, medicine composition containing the total alkaloids extraction and application thereof |
| CN101402637B (en) * | 2008-11-17 | 2011-08-03 | 曾建国 | Process for producing protopine total alkaloids extract |
| CN103265549B (en) * | 2013-05-07 | 2015-12-23 | 西安交通大学 | A kind of method extracting protopine from honey raisin tree seven |
| CN106317066B (en) * | 2015-06-19 | 2019-02-15 | 广州白云山中一药业有限公司 | The method of protopine and its pharmaceutical preparation is prepared from Chinese medicine decumbent corydalis tuber |
| CN110715987B (en) * | 2019-10-23 | 2022-05-03 | 张璐 | Quality control method for Yujiang corydalis amabilis |
| CN112279859A (en) * | 2020-12-14 | 2021-01-29 | 南京康齐生物科技有限公司 | Method for extracting and separating high-purity protopine from macleaya cordata |
Citations (1)
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| CN1579387A (en) * | 2004-05-20 | 2005-02-16 | 北京神农坛医药科技有限公司 | Extraction of protopine from plant, and its manufacture of medicinal preparation and use |
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| CN1579387A (en) * | 2004-05-20 | 2005-02-16 | 北京神农坛医药科技有限公司 | Extraction of protopine from plant, and its manufacture of medicinal preparation and use |
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| 原阿片碱提取工艺的改进 章明等，天然产物研究与开发，第5卷第1期 1993 * |
| 夏天无的研究概况 刘梅等，江西中医学院学报，第16卷第1期 2004 * |
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