CN110229149A - A method of separating quinine from ledger bark - Google Patents
A method of separating quinine from ledger bark Download PDFInfo
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- CN110229149A CN110229149A CN201910650775.6A CN201910650775A CN110229149A CN 110229149 A CN110229149 A CN 110229149A CN 201910650775 A CN201910650775 A CN 201910650775A CN 110229149 A CN110229149 A CN 110229149A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
Abstract
The method that the present invention provides a kind of to separate quinine from ledger bark, it the described method comprises the following steps: (1) impregnating ledger bark at least once using the mixed solution that acid solution and chloroform form, leachate is adsorbed using strongly acidic macroporous cation exchange resin；(2) strongly acidic macroporous cation exchange resin is eluted using the mixed solution of methanol and ammonium hydroxide, eluent is concentrated；(3) product after concentration in step (2) is dissolved using organic solvent, filtering, filtrate concentration obtain quinine after adjusting pH value to 6.5~7 using sulfuric acid dissolution；It generally can reach 5% or more using the yield of method quinine provided by the invention, can reach 5.6% or so, be conducive to the application of quinine.
Description
Technical field
The invention belongs to Chemical Decomposition fields, are related to a kind of method that quinine is separated from ledger bark.
Background technique
Ledger bark contains more than 30 kinds of alkaloids, wherein predominantly quinine, is secondly quinindium, cinchonidine, cinchonine
Deng.Additionally containing cinchotannin, quininic acid and cinchona red etc..Quinine is antimalarial specific drug, and preparation can eliminate various malarias
The schizont of protozoon terminates the breaking-out of malaria, especially good to tertian fever curative effect.Before the curative effect for understanding ledger bark, need to first it understand
One chemical noun: the aromatic heterocycle that a CH base of benzene is constituted with nitrogen (N) atomic substitutions is pyridine, if by hydrogen atom
And unify a phenyl ring and become quinoline (quinoline), and the source of the latter's earliest period is the alkaloid on ledger bark.
Ledger bark contains the alkaloids such as quinine (quinine), chinidine, cinchonine, cinchonidine, and it is all raw to account for it
The 30~60% of alkaloids.Quinine can treat malaria, and eight or two zero year of Yu Yi is by famous French alkaloid great master Bai Liti
(P.Pelletier) isolated, but its chemical constitution until twentieth century just determined completely.And it is chinidine, cinchonine, pungent
Can the fixed antimalarial of Buddhist nun it is weaker, but chinidine separately have prevent cardiac muscle fibre tremble function, can adopt oral way treatment the rhythm of the heart lose
Often, still there is dizziness unfortunately, the side effects such as vomit and drop.
Quinine, that is, quinine is a kind of chemical substance, white granular or microcrystalline powder, micro- efflorescence properties.It is odorless, taste
Slight bitter.It is slightly soluble in water and glycerol, is soluble in ethyl alcohol, chloroform is dissolved in diluted acid, in weak aqua ammonia.It is in strong blue-fluorescence in sulfuric acid, with
Many acid salt easily generated.
CN101402634A discloses a kind of isolation and purification method of alkaloid in ledger bark, passes through acidic aqueous solution
Soak extraction, the method that ion exchange resin concentration and separation purifies quinine, greatly reduces the usage amount of organic solvent, significant to drop
Energy consumption needed for low concentration organic solvent, on the basis of guaranteeing that extracting recovery rate is not less than solvent method, biggish drop
Low production cost, alleviates the adverse effect to environment.This method changes Extraction medium, avoids organic solvent and is extracted with water；
The ion exchange resin used using iterative regenerable is avoided heating concentration, reduces the consumption of the energy as enrichment method mode.
CN101638413A discloses a kind of isolation and purification method of vinca alkaloids, includes the following steps: that (1) is thick
The pretreatment of product: by, on alumina column, elution collects alkaloid fraction, after merging in vinca alkaloids crude product wet process
It is concentrated to dryness, obtains pre-treatment preparations；(2) high performance liquid chromatography separation: first preparing chromatographic column fixed phase, and filler is silica gel,
Sample introduction, gradient elution, detector tracking system merge for chromatographic isolation situation, thin-layer chromatography or efficient liquid phase detection and are rich in Changchun
Alkali fraction；(3) it recrystallizes: alkaloid fraction is concentrated to dryness, then lower aliphatic alcohols dissolution is placed crystallization, filtered, does
It is dry.The present invention is suitable for isolating and purifying for vinca alkaloids, without particular fillers are used, does not also need molten using high toxicity
Agent.Easy to operate, high degree of automation, good separating effect, filler used in stationary phase once fill column, are used for multiple times.Mobile phase can
Recycling, environment friendly and economical are suitable for industrialized production.
CN109806286A discloses a kind of separation method of alkaloid in leaf of Moringa, and separation method is as follows: weighing certain
Leaf of Moringa is measured, adds 10 times of amount water, extracts 30min at microwave power 800W, 90 DEG C of temperature, filter while hot, filtrate is Moringa
Leaf water extract.Appropriate dipotassium hydrogen phosphate ultrasound is added in leaf of Moringa water extract to be made to dissolve, and adds a certain amount of ethyl alcohol, and adjust
Optimum pH is saved, double-aqueous phase system is constructed, at 40 DEG C, stirring extraction 10min is transferred in separatory funnel, stratification, takes out
Upper layer phase simultaneously replaces fresh upper phase, carries out multistage cross flow extraction, merges upper liquid, is dried under reduced pressure to obtain the final product.This method is not applicable
In the extraction to quinine.
Although currently, about alkaloid separation method there are many, the separation method in relation to quinine is also less,
A kind of method that extraction efficiency is high, yield is increased how is developed, is of great significance for the popularization and application of quinine.
Summary of the invention
In view of the deficiencies of the prior art, the purpose of the present invention is to provide one kind, and quinine is separated from ledger bark
Method, yield not high problem poor to solve extraction effect in existing method.
To achieve this purpose, the present invention adopts the following technical scheme:
The method that the present invention provides a kind of to separate quinine from ledger bark, the method includes following steps
It is rapid:
(1) ledger bark is impregnated at least once using the mixed solution that acid solution and chloroform form, leachate makes
It is adsorbed with strongly acidic macroporous cation exchange resin；
(2) strongly acidic macroporous cation exchange resin is eluted using the mixed solution of methanol and ammonium hydroxide, eluent carries out dense
Contracting；
(3) product after concentration in step (2) is dissolved using organic solvent, filtering, filtrate concentration are molten using sulfuric acid
It solves, obtains quinine after adjusting pH value to 6.5~7.
The method provided by the invention that quinine is separated from ledger bark, it is molten with chloroform by using acid solution
The mixing of liquid has achieved the purpose that quinine in first extraction ledger bark, and main component loss is less, compared to independent
Being easily caused using the immersion of acid solution leads to the problem of being lost at salt under acid condition, and quinine is molten in mixed solution
It is more preferable to solve effect, while being dissolved after concentration using specific organic solvent, the loss of quinine is further avoided,
Later crystallization is promoted to be promoted at the effect of salt.
Preferably, acid solution described in step (1) is hydrochloric acid solution and/or nitric acid solution.
Preferably, the mass percent of acid solution described in step (1) is 5%~6%, such as can be 5%,
5.1%, 5.2%, 5.3%, 5.4%, 5.5%, 5.6%, 5.7%, 5.8%, 5.9% or 6% etc..
In the present invention, the mass percentage content of acid solution can generate the extraction separation of quinine certain
It influences, it is generally preferable to which the acid solution that mass percent is 5%~6% is best for final extraction effect.Excessive concentration is not
Conducive to subsequent resin adsorption and elution, concentration is too low to be not achieved good extracting effect.
Preferably, the volume ratio of acid solution described in step (1) and chloroform is 1:3~5, such as can be 1:3,1:
3.2,1:3.5,1:3.8,1:4.3,1:4.8 or 1:5 etc..
In the present invention, the chloroform of Optimum and acid solution collocation, are able to ascend the extracting effect of quinine, make
The amount for obtaining subsequent adsorbtion is bigger, is able to ascend the yield of final product.
Preferably, immersion described in step (1) is impregnates 3~5 times, such as to can be 3 times, 4 times or 5 inferior.
Preferably, the strongly acidic macroporous cation exchange resin includes LSD001 type highly acid macropore amberlite
Any one in rouge, AB-8 type highly acid macroporous ion exchange resin or HB-8 type highly acid macroporous ion exchange resin.
Preferably, the volume ratio of methanol described in step (2) and ammonium hydroxide be (2~6): 1, for example, can be 2:1,2.5:1,
3:1,3.5:1,4:1,4.5:1,5:1,5.5:1 or 6:1 etc..
Preferably, it is 73% that methanol and ammonium hydroxide, which account for volume fraction total in solution, in the mixed solution of the methanol and ammonium hydroxide
~75%, such as can be 73%, 73.2%, 73.5%, 73.8%, 73.9%, 74%, 74.5%, 74.8% or 75% etc..
Preferably, organic solvent described in step (3) be chloroform, benzene or ether in any one or at least two group
It closes；The preferably combination of benzene and ether.
Preferably, the method for filtering described in step (3), filtrate concentration are as follows: after being first concentrated using benzene dissolving step (2) are middle
Product, filtering, filtrate concentration after reuse ether dissolution concentration product use sulfuric acid dissolution after filtering and concentrating.
In the present invention, by using the dissolution of organic solvent, the product being concentrated to get in step (2) can be dissolved more
Thoroughly, and by way of filtering, a part of impurity can be filtered out, so that the purity of final products is improved.Compared to
Directly using sulphur bronsted lowry acids and bases bronsted lowry at the method for salt, the purity of product is higher.
It is a discovery of the invention that first reusing ether dissolution filtering and concentrating using the dissolution of benzene, filtering and concentrating, enabling to most
The purity and yield of the quinine obtained eventually reach best.
Preferably, the mass percent concentration of the sulfuric acid is 20%~25%, for example, can be 20%, 21%, 22%,
23%, 24% or 25% etc..
Preferably, using alkali adjusting pH value to 6.5~7, such as 6.5,6.6,6.7,6.8,6.9 or 7 etc. be can be
Preferably, the alkali include in sodium carbonate, potassium carbonate or sodium bicarbonate any one or at least two combination.
When adjusting pH value using the alkali of the above-mentioned type, the milder for enabling to reaction to carry out, the effect that product is precipitated is more
Good, compared to highly basic such as sodium hydroxide, potassium hydroxide, the effect of Precipitation is more thorough.
As optimal technical scheme, the method provided by the invention that quinine is separated from ledger bark is specifically included
Following steps:
(1) ledger bark is impregnated 3 using the mixed solution of acid solution and chloroform composition that volume ratio is 1:3~5
~5 times, leachate is adsorbed using strongly acidic macroporous cation exchange resin；
(2) the use of volume ratio is (2~6): 1 methanol and the mixed solution of ammonium hydroxide elute highly acid macroporous cation and exchange
Resin, eluent carry out first time concentration, obtain medicinal extract, wherein methanol and ammonium hydroxide account for volume fraction total in solution be 73%~
75%；
(3) product after concentration in step (2) is dissolved using benzene, is filtered, it is dense to reuse ether dissolution after filtrate concentration
The product of contracting using sulfuric acid dissolution, adjusts pH value to obtaining quinine after 6.5~7 using alkali after filtering, concentration.
Compared with the existing technology, the invention has the following advantages:
The method provided by the invention that quinine is separated from ledger bark, it is molten with chloroform by using acid solution
The mixing of liquid has achieved the purpose that quinine in first extraction ledger bark, and main component loss is less, compared to independent
Being easily caused using the immersion of acid solution leads to the problem of being lost at salt under acid condition, and quinine is molten in mixed solution
It is more preferable to solve effect, while being dissolved after concentration using specific organic solvent, the loss of quinine is further avoided,
Later crystallization is promoted to be promoted at the effect of salt, the yield of quinine generally can reach 5% or more, can reach
5.6% or so, be conducive to the application of quinine.
Specific embodiment
The technical scheme of the invention is further explained by means of specific implementation.Those skilled in the art should be bright
, the described embodiments are merely helpful in understanding the present invention, should not be regarded as a specific limitation of the invention.
Embodiment 1
The method that the present embodiment provides a kind of to separate quinine from ledger bark
(1) 100g ledger bark is impregnated 4 using the mixed solution of hydrochloric acid solution and chloroform composition that volume ratio is 1:4
Secondary, leachate is adsorbed using HB-8 type highly acid macroporous ion exchange resin；Wherein the mass percent of hydrochloric acid solution is
5%；
(2) HB-8 type highly acid macropore ion exchange is eluted using the mixed solution of methanol and ammonium hydroxide that volume ratio is 4:1
Resin, eluent carry out first time concentration, obtain medicinal extract, and it is 74% that wherein methanol and ammonium hydroxide, which account for volume fraction total in solution,；
(3) product after concentration in step (2) is dissolved using benzene, is filtered, it is dense to reuse ether dissolution after filtrate concentration
The product of contracting, after filtering, concentration, the sulfuric acid dissolution for the use of mass percent concentration being 22% is adjusted using sodium carbonate
PH value is to obtaining quinine, quality 5.6g, yield 5.6% after 6.8.
Embodiment 2
The method that the present embodiment provides a kind of to separate quinine from ledger bark
(1) 100g ledger bark is impregnated 3 using the mixed solution of nitric acid solution and chloroform composition that volume ratio is 1:3
Secondary, leachate is adsorbed using HB-8 type highly acid macroporous ion exchange resin；Wherein the mass percent of nitric acid solution is
6%；
(2) HB-8 type highly acid macropore ion exchange is eluted using the mixed solution of methanol and ammonium hydroxide that volume ratio is 2:1
Resin, eluent carry out first time concentration, obtain medicinal extract, and it is 73% that wherein methanol and ammonium hydroxide, which account for volume fraction total in solution,；
(3) product after concentration in step (2) is dissolved using benzene, is filtered, it is dense to reuse ether dissolution after filtrate concentration
The product of contracting, after filtering, concentration, the sulfuric acid dissolution for the use of mass percent concentration being 20% is adjusted using potassium carbonate
PH value is to obtaining quinine, quality 5.3g, yield 5.3% after 6.5.
Embodiment 3
The method that the present embodiment provides a kind of to separate quinine from ledger bark
(1) 100g ledger bark is impregnated 5 using the mixed solution of hydrochloric acid solution and chloroform composition that volume ratio is 1:5
Secondary, leachate is adsorbed using AB-8 type highly acid macroporous ion exchange resin；Wherein the mass percent of nitric acid solution is
5%；
(2) HB-8 type highly acid macropore ion exchange is eluted using the mixed solution of methanol and ammonium hydroxide that volume ratio is 6:1
Resin, eluent carry out first time concentration, obtain medicinal extract, and it is 75% that wherein methanol and ammonium hydroxide, which account for volume fraction total in solution,；
(3) product after concentration in step (2) is dissolved using chloroform, is filtered, reuse ether dissolution after filtrate concentration
The product of concentration, after filtering, concentration, the sulfuric acid dissolution for the use of mass percent concentration being 25% uses sodium bicarbonate
PH value is adjusted to obtaining quinine, quality 5.0g, yield 5% after 7.
Embodiment 4
The method that the present embodiment provides a kind of to separate quinine from ledger bark
(1) 100g ledger bark is impregnated 4 using the mixed solution of hydrochloric acid solution and chloroform composition that volume ratio is 1:3
Secondary, leachate is adsorbed using LSD001 type highly acid macroporous ion exchange resin；The wherein mass percent of nitric acid solution
It is 5%；
(2) HB-8 type highly acid macropore ion exchange is eluted using the mixed solution of methanol and ammonium hydroxide that volume ratio is 6:1
Resin, eluent carry out first time concentration, obtain medicinal extract, and it is 73% that wherein methanol and ammonium hydroxide, which account for volume fraction total in solution,；
(3) product after concentration in step (2) is dissolved using chloroform, is filtered, it is dense that benzene dissolution is reused after filtrate concentration
The product of contracting, after filtering, concentration, the sulfuric acid dissolution for the use of mass percent concentration being 25% is adjusted using sodium carbonate
PH value is to obtaining quinine, quality 4.9g, yield 4.9% after 7.
Embodiment 5
The present embodiment the difference from embodiment 1 is that, the mass percent of hydrochloric acid solution is in step (1) in the present embodiment
2%, remaining is same as Example 1 to obtain quinine, yield 4.6%.
Embodiment 6
The present embodiment the difference from embodiment 1 is that, the mass percent of hydrochloric acid solution is in step (1) in the present embodiment
10%, remaining is same as Example 1 to obtain quinine, yield 4.5%.
Embodiment 7
The present embodiment the difference from embodiment 1 is that, in the present embodiment in step (1) hydrochloric acid solution and chloroform volume ratio
For 1:1, remaining is same as Example 1 to obtain quinine, yield 4.5%.
Embodiment 8
The present embodiment the difference from embodiment 1 is that, in the present embodiment in step (1) hydrochloric acid solution and chloroform volume ratio
For 1:7, remaining is same as Example 1 to obtain quinine, yield 4.7%.
Embodiment 9
The present embodiment the difference from embodiment 1 is that, is dissolved using ethyl alcohol in step (3) in the present embodiment, filtering and concentrating
After reuse sulfuric acid dissolution, remaining is same as Example 1 to obtain quinine, yield 4.3%.
Comparative example 1
This comparative example the difference from embodiment 1 is that, in this comparative example step (1) be used only hydrochloric acid solution impregnated,
Without the use of chloroform, remaining is same as Example 1 to obtain quinine, yield 4.2%.
Comparative example 2
This comparative example the difference from embodiment 1 is that, in this comparative example step (3) directly by step (2) be concentrated product
Using sulfuric acid dissolution, and the step of dissolving without organic solvent, remaining is same as Example 1 to obtain quinine, yield
4.1%.
By the result of above embodiments 1-9 and comparative example 1-2 it is found that provided by the invention separate from ledger bark
The method of quinine, yield generally can reach 5% or more, can reach 5.6% or so, yield is higher.
And when variation has occurred in the separation condition in step (1), the yield of quinine declines.And when in step (3)
Organic solvent when being not preferred the solvent in range, yield is also declined.
When not using chloroform in step (1), yield only has 4% or so；And in step (3) without using organic solvent into
When row dissolution, yield also only has 4% or so, and purity is poor.
The Applicant declares that the present invention is explained by the above embodiments of the invention separates quinine from ledger bark
The method of alkali, but the invention is not limited to above-mentioned method detaileds, that is, do not mean that the present invention must rely on above-mentioned method detailed
It could implement.It should be clear to those skilled in the art, any improvement in the present invention, to each raw material of product of the present invention
Equivalence replacement and addition, the selection of concrete mode of auxiliary element etc., all fall within protection scope of the present invention and the open scope
Within.
Claims (10)
1. a kind of method for separating quinine from ledger bark, which is characterized in that the described method comprises the following steps:
(1) ledger bark is impregnated at least once using the mixed solution that acid solution and chloroform form, leachate uses strong
Acid large hole cation exchanger resin is adsorbed；
(2) strongly acidic macroporous cation exchange resin is eluted using the mixed solution of methanol and ammonium hydroxide, eluent is concentrated；
(3) product after concentration in step (2) is dissolved using organic solvent, filtering, filtrate concentration are adjusted using sulfuric acid dissolution
Section pH value is to obtaining quinine after 6.5~7.
2. the method according to claim 1, wherein acid solution described in step (1) be hydrochloric acid solution and/or
Nitric acid solution；
Preferably, the mass percent of acid solution described in step (1) is 5%~6%；
Preferably, the volume ratio of acid solution described in step (1) and chloroform is 1:3~5.
3. method according to claim 1 or 2, which is characterized in that immersion described in step (1) is immersion 3~5 times.
4. method according to any one of claim 1-3, which is characterized in that the highly acid macroporous cation exchange tree
Rouge includes LSD001 type highly acid macroporous ion exchange resin, AB-8 type highly acid macroporous ion exchange resin or HB-8 type strong acid
Any one in property macroporous ion exchange resin.
5. method according to any of claims 1-4, which is characterized in that methanol described in step (2) and ammonium hydroxide
Volume ratio is (2~6): 1；
Preferably, in the mixed solution of the methanol and ammonium hydroxide methanol and ammonium hydroxide account for volume fraction total in solution be 73%~
75%.
6. method according to any one of claims 1-5, which is characterized in that organic solvent described in step (3) is chlorine
In imitative, benzene or ether any one or at least two combination；The preferably combination of benzene and ether.
7. method according to claim 1 to 6, which is characterized in that filtering described in step (3), filtrate concentration
Method are as follows: first using the product after concentration in benzene dissolving step (2), filtering reuses ether dissolution concentration after filtrate concentration
Product use sulfuric acid dissolution after filtering and concentrating.
8. method according to any one of claims 1-7, which is characterized in that the mass percent concentration of the sulfuric acid is
20%~25%.
9. method according to claim 1 to 8, which is characterized in that adjust pH value to 6.5~7 using alkali；
Preferably, the alkali include in sodium carbonate, potassium carbonate or sodium bicarbonate any one or at least two combination.
10. method according to claim 1 to 9, which is characterized in that the described method comprises the following steps:
(1) ledger bark is impregnated 3~5 using the mixed solution of acid solution and chloroform composition that volume ratio is 1:3~5
Secondary, leachate is adsorbed using strongly acidic macroporous cation exchange resin；
(2) the use of volume ratio is (2~6): 1 methanol and the mixed solution of ammonium hydroxide elute highly acid macroporous cation exchange tree
Rouge, eluent carry out first time concentration, obtain medicinal extract, wherein methanol and ammonium hydroxide account for volume fraction total in solution be 73%~
75%；
(3) product after concentration in step (2) is dissolved using benzene, is filtered, ether dissolution concentration is reused after filtrate concentration
Product using sulfuric acid dissolution, adjusts pH value to obtaining quinine after 6.5~7 using alkali after filtering, concentration.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB758173A (en) * | 1953-10-12 | 1956-10-03 | Buzas Andre | Process for extracting quinine from cinchona bark |
| DE3704850A1 (en) * | 1987-02-16 | 1988-08-25 | Mueller Adam | Process for the preparation of quinine from cinchona bark by extraction with supercritical CO2 |
| CN101402634A (en) * | 2008-11-11 | 2009-04-08 | 广州普星药业有限公司 | Separation and purification process for alkaloid in cinchona bark |
| CN102558169A (en) * | 2010-12-10 | 2012-07-11 | 江苏斯威森生物医药工程研究中心有限公司 | Industrialized production method for efficiently extracting, separating and purifying serial cinchona alkaloid from cinchona bark |
| CN102766140A (en) * | 2012-08-14 | 2012-11-07 | 玉溪市维和生物技术有限责任公司 | Process for separating and preparing quinine sulfate from peruvian bark |
-
2019
- 2019-07-18 CN CN201910650775.6A patent/CN110229149A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB758173A (en) * | 1953-10-12 | 1956-10-03 | Buzas Andre | Process for extracting quinine from cinchona bark |
| DE3704850A1 (en) * | 1987-02-16 | 1988-08-25 | Mueller Adam | Process for the preparation of quinine from cinchona bark by extraction with supercritical CO2 |
| CN101402634A (en) * | 2008-11-11 | 2009-04-08 | 广州普星药业有限公司 | Separation and purification process for alkaloid in cinchona bark |
| CN102558169A (en) * | 2010-12-10 | 2012-07-11 | 江苏斯威森生物医药工程研究中心有限公司 | Industrialized production method for efficiently extracting, separating and purifying serial cinchona alkaloid from cinchona bark |
| CN102766140A (en) * | 2012-08-14 | 2012-11-07 | 玉溪市维和生物技术有限责任公司 | Process for separating and preparing quinine sulfate from peruvian bark |
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Application publication date: 20190913 |