CN101139321B - Method for separating and purifying nuciferine by employing cationic ion-exchange resin - Google Patents
Method for separating and purifying nuciferine by employing cationic ion-exchange resin Download PDFInfo
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- CN101139321B CN101139321B CN2007100094653A CN200710009465A CN101139321B CN 101139321 B CN101139321 B CN 101139321B CN 2007100094653 A CN2007100094653 A CN 2007100094653A CN 200710009465 A CN200710009465 A CN 200710009465A CN 101139321 B CN101139321 B CN 101139321B
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Abstract
The present invention provides a method of separation and purification of the nuciferine using the cation exchange resin. The steps of the method are: the cation exchange resin is used to absorb the solution containing nuciferine to be saturated; the pure water and the hydrophilic organic solvent of a certain concentration are respectively used to wash the residual material solution and the impurities of the weak adsorption capability without the ion exchange; then the eluant with the cation of a certain concentration is used to eluate the nuciferine; the eluant solution recycles some solvent and the regulator of the nuciferine solubility is added; the eluant solution is slowly cooled and begins to separate out the nuciferine crystal; the eluant solution is laid statically at a low temperature to produce the crystal, and filtered to get the nuciferine crystal. The nuciferine crystal can be further recrystallized with the hydrophilic organic solvent at the room temperature; the water and petroleum ether are respectively used to wash the crystal and eliminate the impurities to get the high-purity nuciferine crystal. The present invention has the novel scheme, the simple process, the high extraction rate, the low production cost, the great capability for promotion and so on.
Description
Technical field
The present invention relates to a kind of from medicine food dual purpose plant the alkaloidal method of separation and purification, more specifically relate to a kind of method that adopts Zeo-karb separation and purification Nuciferine.
Background technology
Lotus (Nelumbo nucifera Gaertn) is a kind of medicine food dual purpose plant, at China's the South and the North plantation is arranged all, and plantation history reaches more than 3000 year, abounds with in Fujian at present, provinces such as Jiangxi, Hubei, Hunan and Zhejiang.
Lotus leaf (Nelumbo nucifera leaf) is the dry leave of lotus, has another name called lotus leaf or lotus root leaf, the plant register of selected ministry of Health of China " being food, is again medicine ", food and the medicine of being widely used as among the people.As the medicinal ingredients of natural phant, bioactive functions such as the reducing blood-fat of lotus leaf alkaloid and lotus flavone, decreasing cholesterol and fat-reducing receive publicity in recent years [Kong Wenqi etc., " traditional Chinese medicine research and information ", 2005,7 (6): 22-24].In China, the lotus leaf aboundresources, cheap and easy to get, drug effect is clear and definite.
At present, extracting lotus leaf alkaloid method commonly used has: acidic aqueous solution extraction method [Chen Haiguang etc., " food and machinery ", 2001,17 (5): 16-17; Jiang Yihong, " journal of Zhejiang university (agricultural and life science version) " 2004,30 (5): 519-523; ], adopt macroporous resin enrichment absorption method [Zhao Jun etc., " Chinese medicinal materials ", 2003,26 (9): 669-670] behind the acidic water extract.
At present, divide according to the chemical constitution of resin matrix, cation exchange resin product mainly contains products such as polystyrene, acrylic acid series, phenolic aldehyde system, epoxy system, vinylpyridine system, urea aldehyde system and vinyl chloride; Then can be divided into 001 serial storng-acid cation exchange resin of East China University of Science and Nankai University [as 001 * 2 (trade(brand)name 735) according to the brand of resin, 001 * 4 (trade(brand)name 734), 001 * 7 (trade(brand)name 732)] and 112,110,122 serial weakly acidic cation-exchange resins are [as 112 * 1 (trade(brand)names 724), 112 * 4 (trade(brand)names 101), 110,122] etc., the Amberlite series of Shanghai Rhom and Hass (sino-america joint-venture) is [as AmberliteIR-120 (strong acid), Amberlite IRC-50 (weak acid)] and Zhejiang float the Dowex series of Lai Te (Sino-British joint) (as Dowex 50 cation exchange resin product such as (strong acid).
The pure product of Nuciferine (Nuciferine is called for short NF) are white needle-like crystals.Because Nuciferine is a weakly alkaline organic-biological alkali, can not directly be dissolved in water, but be soluble in the acidic aqueous solution of hydrophilic organic solvents such as methyl alcohol, ethanol, acetone, be slightly soluble in sherwood oil, ether, ethyl acetate and the chloroform of heat.Therefore, according to the ion-exchange theory, under acidic conditions, Nuciferine is to exist with the positively charged ion state, can adopt ion exchange technique to separate Nuciferine.Contain H to being adsorbed on the Nuciferine on the Zeo-karb, can adopting
+, K
+, Na
+, NH
4 +Eluent Deng mineral ion carries out wash-out, and this eluent can be acid, neutral or alkaline hydrophilic organic solvent.
Summary of the invention
The object of the present invention is to provide a kind of method that adopts Zeo-karb separation and purification Nuciferine, not only equipment is simple for this method, good separating effect, product yield height, and resin long service life, production cost are low.
The method of employing Zeo-karb separation and purification Nuciferine of the present invention is achieved in that the solution that contains Nuciferine, extremely saturated with cationic exchange resin adsorption, with pure water and certain density hydrophilic organic solvent flush away the residual feed liquid of ion-exchange and the adsorptive power impurity a little less than than Nuciferine does not take place respectively, again with containing the cationic eluent wash-out of finite concentration Nuciferine, add Nuciferine solubleness conditioning agent behind the elutriant recovery part solvent, slowly the cooling elutriant is to beginning to separate out the Nuciferine crystal, the stand at low temperature growing the grain, filter, get the Nuciferine crystallization.
When the present invention adopts strongly acidic cation-exchange, preferentially select for use to contain K
+, Na
+, NH
4 +Solution Deng mineral ion is eluent, as: NH
4OH, NaCl, K
2SO
4Deng; When adopting the weak-type Zeo-karb, preferentially selecting dilute acid soln for use is eluent, as: HCl, H
2SO
4Deng.
Preparation method's of the present invention major advantage is:
(1) preferentially select for use the major advantage of above-mentioned Zeo-karb to be: the active ion in the functional group of strongly acidic cation-exchange is-SO
3H, pK
a＜1, the pH value is little to its elutive power influence; Elutive power is mainly relevant with the concentration of eluent and contained cation valence, the concentration of eluent and contained cation valence are high more, it is just big more to the elutive power that is adsorbed on material on the strongly acidic cation-exchange, but the active ion in the functional group of weak-type Zeo-karb is-COOH pK
a=4.0～5.6, the pH value is bigger to its elutive power influence; Elutive power is not only relevant with the concentration of eluent and contained cation valence, and prior influence factor is the pH value of eluent, as the pH of eluent value＜pK
aThe time, cause the functional group of weak-type Zeo-karb not dissociate and present molecularity, lost the ability that exchanges with positively charged ion, the material that is adsorbed on the resin is eluted easily.
(2) preparation method of the present invention has made full use of under acid ph value condition Zeo-karb to the avidity of targeted activity material Nuciferine and difference to the avidity of impurity such as polysaccharide, pigment, and certain density eluent solution different to the elutive power that is adsorbed on Nuciferine and other impurity on the ion exchange resin, really reach the high efficiency separation of Nuciferine and impurity, be easy to prepare highly purified Nuciferine product.
Embodiment
The present invention adopts the method for Zeo-karb separation and purification Nuciferine, its method steps is: the hydrophilic organic solvent aqueous solution that contains Nuciferine, at acid ph value, be under pH value＜7 conditions, extremely saturated with cationic exchange resin adsorption, the impurity of 30～50% hydrophilic organic solvent aqueous solution flush away adsorptive poweies that the residual feed liquid of ion-exchange do not take place and be no less than 2 times of amount of resin (V/V) with the pure water flush away that is no less than 1 times of amount of resin (V/V) a little less than than Nuciferine, use the eluent aqueous solution of 0.25～1.2mol/L cation concn of 3～10 times of amount of resin (V/V) again, with 1～3 times of amount of resin/hour flow velocity (V/V) wash-out Nuciferine, elutriant-0.06～-0.095MPa, under 50～80 ℃ of conditions, behind the reclaim under reduced pressure partial solvent, add Nuciferine solubleness conditioning agent, slowly the cooling elutriant is to beginning to separate out the Nuciferine crystal, 4～10 ℃ leave standstill growing the grain, filter, get the Nuciferine crystallization.The Nuciferine crystallization also can be used the hydrophilic organic solvent recrystallization further at ambient temperature, and water and sherwood oil are washed brilliant removal of impurities respectively then, gets high purity Nuciferine crystal.
Wherein, hydrophilic organic solvent is one or more mixed solvents in methyl alcohol, ethanol, acetone, propyl alcohol or the Virahol.
The solution that contains Nuciferine can be the crystalline mother solution that derives from lotus leaf alkaloid, adopts lotus leaf alkaloid extracting solution that means such as solvent extraction, macroporous adsorbent resin enrichment or membrane separation for removing impurities obtain or in the lotus leaf alkaloid elutriant one or more.
The cation composition of eluent is H
+, K
+, Na
+, NH
4 +Deng in the mineral ion one or more.
Eluent can be one or more in acid, the neutral or alkaline hydrophilic organic solvent.
The chemical constitution of Zeo-karb skeleton can be one or more in polystyrene, polyacrylic acid or the phenolic aldehyde.
The Nuciferine assay: adopt high performance liquid chromatography, (purity 99% is available from Chinese biological goods calibrating institute) is contrast with the Nuciferine standard substance.Chromatographic condition is: Agilent 1100 type high performance liquid chromatographs (DAD diode-array detector), chromatographic column is Yi Lite C
18Reversed-phase column (Φ 4.6 * 200mm, 4 μ m), moving phase is methyl alcohol and 0.2% triethylamine solution gradient elution, is changed to 90% by 50% in the methanol concentration 15min; Flow velocity 1.0ml/min, 30 ℃ of column temperatures detect wavelength 272nm, sample size 20 μ L.The UV spectrum of Nuciferine, infrared spectra, LC-MS and liquid chromatography are identified and are carried out according to GB.
Preparation method's of the present invention embodiment is presented below:
Embodiment 1
The lotus leaf alcohol extract that contains lotus leaf alkaloid, be adjusted to pH value 1.65, alcohol concn 32%, the feed liquid of Nuciferine concentration 1.35g/L, adopt Amberlite IR-120 storng-acid cation exchange resin, with 0.75 times of amount of resin (V/V)/hour last column flow rate dynamic adsorption Nuciferine to saturated, impurity a little less than using the residual feed liquid of ion-exchange and 4 times of amount of resin (V/V) do not take place the pure water flush away of 2 times of amount of resin (V/V) 35% aqueous ethanolic solution flush away adsorptive power than Nuciferine respectively, use 80% aqueous ethanolic solution that contains 1.2mol/L NaCl of 3 times of amount of resin (V/V) again, with 2 times of amount of resin (V/V)/hour flow velocity wash-out Nuciferine, elutriant-0.06～-0.095MPa, under 50～80 ℃ of conditions, behind the reclaim under reduced pressure partial solvent, add Nuciferine solubleness conditioning agent, alcohol concn 32% and pH value 5.1 in the control elutriant system, slowly cooling Nuciferine elutriant is to beginning to separate out the Nuciferine crystal, 4～10 ℃ leave standstill growing the grain, filter, get the Nuciferine crystallization.After measured, the rate of recovery 82.6% of Nuciferine, the purity of Nuciferine are 83.1%.
The Nuciferine crystallization also can with 95% ethyl alcohol recrystallization of 5 times of amounts, be washed brilliant removal of impurities with the water of 6 times of amounts and the sherwood oil of 4 times of amounts respectively then further under 28 ℃ of conditions, purity is 98.2% Nuciferine crystal.Nuciferine crystalline UV spectrum, infrared spectra, LC-MS and liquid chromatography qualification result conform to the Nuciferine standard substance.
Embodiment 2
Contain lotus leaf alkaloid crystalline mother solution, be adjusted to pH value 6.08, alcohol concn 40%, the feed liquid of Nuciferine concentration 0.46 g/L, adopt polyacrylic 724 weakly acidic cation-exchange resins, Static Adsorption is to saturated under the mixing speed condition of 68r/min, impurity a little less than using the residual feed liquid of ion-exchange and 2 times of amount of resin (V/V) do not take place the pure water flush away of 3 times of amount of resin (V/V) 50% aqueous ethanolic solution flush away adsorptive power than Nuciferine respectively, use 40% aqueous ethanolic solution that contains 0.25mol/LHCl of 8 times of amount of resin (V/V) again, with 1 times of amount of resin (V/V)/hour flow velocity wash-out Nuciferine, elutriant-0.06～-0.095MPa, under 50～80 ℃ of conditions, behind the reclaim under reduced pressure partial solvent, add Nuciferine solubleness conditioning agent, alcohol concn 18% and pH value 6.9 in the control elutriant system, slowly cooling Nuciferine elutriant is to beginning to separate out the Nuciferine crystal, 4～10 ℃ leave standstill growing the grain, filter, get the Nuciferine crystallization.After measured, the rate of recovery 83.9% of Nuciferine, the purity of Nuciferine are 80.6%.
The Nuciferine crystallization also can with the dehydrated alcohol recrystallization of 6 times of amounts, be washed brilliant removal of impurities with the water of 10 times of amounts and the sherwood oil of 2 times of amounts respectively then further under 30 ℃ of conditions, purity is 96.7% Nuciferine crystal.
Embodiment 3
The Lotus Leafextract that contains lotus leaf alkaloid through membrane separation for removing impurities, be adjusted to the feed liquid of pH value 0.93, methanol concentration 28%, Nuciferine concentration 0.71g/L, adopt polystyrene 732 storng-acid cation exchange resins, with 1.05 times of amount of resin (V/V)/hour last column flow rate dynamic adsorption Nuciferine to saturated, impurity a little less than using the residual feed liquid of ion-exchange and 6 times of amount of resin (V/V) do not take place the pure water flush away of 4 times of amount of resin (V/V) 30% methanol aqueous solution flush away adsorptive power than Nuciferine is respectively used 0.65 mol/LNH that contains of 10 times of amount of resin (V/V) again
455% methanol aqueous solution of OH, with 3 times of amount of resin (V/V)/hour flow velocity wash-out Nuciferine, elutriant-0.06～-0.095MPa, 50～80 ℃ of conditions under, behind the reclaim under reduced pressure partial solvent, add Nuciferine solubleness conditioning agent, methanol concentration 28% and pH value 6.2 in the control elutriant system, slowly cooling Nuciferine elutriant leaves standstill growing the grain, filtration to beginning to separate out Nuciferine crystal, 4～10 ℃, the Nuciferine crystallization.After measured, the rate of recovery 80.7% of Nuciferine, the purity of Nuciferine are 80.9%.
The Nuciferine crystallization also can with 90% recrystallizing methanol of 8 times of amounts, be washed brilliant removal of impurities with the water of 8 times of amounts and the sherwood oil of 3 times of amounts respectively then further under 20 ℃ of conditions, purity is 95.4% Nuciferine crystal.
Embodiment 4
The elutriant that contains lotus leaf alkaloid through the macroporous adsorbent resin enrichment, be adjusted to pH value 1.42, acetone concentration 30%, the feed liquid of Nuciferine concentration 0.39 g/L, adopt 732: 735 (2: 1) storng-acid cation exchange resins, with 0.98 times of amount of resin (V/V)/hour last column flow rate dynamic adsorption Nuciferine to saturated, impurity a little less than using the residual feed liquid of ion-exchange and 5 times of amount of resin (V/V) do not take place the pure water flush away of 4 times of amount of resin (V/V) 36% aqueous acetone solution flush away adsorptive power than Nuciferine respectively, that uses 8 times of amount of resin (V/V) again contains 0.46mol/L K
2SO
445% aqueous acetone solution, with 1 times of amount of resin (V/V)/hour flow velocity wash-out Nuciferine, elutriant-0.06～-0.095MPa, 50～80 ℃ of conditions under, behind the reclaim under reduced pressure partial solvent, add Nuciferine solubleness conditioning agent, acetone concentration 30% and pH value 5.8 in the control elutriant system, slowly cooling Nuciferine elutriant leaves standstill growing the grain, filtration to beginning to separate out Nuciferine crystal, 4～10 ℃, the Nuciferine crystallization.After measured, the rate of recovery 80.3% of Nuciferine, the purity of Nuciferine are 81.6%.
The Nuciferine crystallization also can with the anhydrous propanone recrystallization of 4 times of amounts, be washed brilliant removal of impurities with the water of 9 times of amounts and the sherwood oil of 4 times of amounts respectively then further under 25 ℃ of conditions, purity is 95.8% Nuciferine crystal.
Above embodiment is intended to further describe for example the present invention, rather than limits the present invention by any way.
The present invention is novel, and technology is simple, the extraction efficiency height, and production cost is low, has bigger dissemination.
Claims (6)
1. method that adopts Zeo-karb separation and purification Nuciferine, it is characterized in that: the solution that contains Nuciferine, extremely saturated with cationic exchange resin adsorption, with pure water and certain density hydrophilic organic solvent flush away the residual feed liquid of ion-exchange and the adsorptive power impurity a little less than than Nuciferine does not take place respectively, again with containing the cationic eluent wash-out of finite concentration Nuciferine, add Nuciferine solubleness conditioning agent behind the elutriant recovery part solvent, slowly the cooling elutriant gets the Nuciferine crystallization to beginning to separate out Nuciferine crystal, stand at low temperature growing the grain, filtration; Detailed process is as follows: the solution that contains Nuciferine, at acid ph value, be under pH value＜7 conditions, extremely saturated with cationic exchange resin adsorption, the impurity of 30～50% hydrophilic organic solvent aqueous solution flush away adsorptive poweies that the residual feed liquid of ion-exchange do not take place and be no less than 2 times of amount of resin (V/V) with the pure water flush away that is no less than 1 times of amount of resin (V/V) a little less than than Nuciferine, use the eluent aqueous solution of 0.25～1.2mol/L cation concn of 3～10 times of amount of resin (V/V) again, with 1～3 times of amount of resin (V/V)/hour flow velocity wash-out Nuciferine, elutriant-0.06～-0.095MPa, under 50～80 ℃ of conditions, behind the reclaim under reduced pressure partial solvent, add Nuciferine solubleness conditioning agent, slowly the cooling elutriant is to beginning to separate out the Nuciferine crystal, 4～10 ℃ leave standstill growing the grain, filter, get the Nuciferine crystallization.
2. the method for employing Zeo-karb separation and purification Nuciferine according to claim 1, it is characterized in that: the Nuciferine crystallization further at ambient temperature, use the hydrophilic organic solvent recrystallization, water and sherwood oil are washed brilliant removal of impurities respectively then, get high purity Nuciferine crystal.
3. the method for employing Zeo-karb separation and purification Nuciferine according to claim 1 is characterized in that: described hydrophilic organic solvent is one or more mixed solvents in methyl alcohol, ethanol, acetone, propyl alcohol or the Virahol.
4. the method for employing Zeo-karb separation and purification Nuciferine according to claim 1, it is characterized in that: the solution that contains Nuciferine is the crystalline mother solution that derives from lotus leaf alkaloid, adopts lotus leaf alkaloid extracting solution that solvent extraction, macroporous adsorbent resin enrichment or membrane separation for removing impurities obtain or in the lotus leaf alkaloid elutriant one or more.
5. the method for employing Zeo-karb separation and purification Nuciferine according to claim 1 is characterized in that: the chemical constitution of Zeo-karb skeleton is one or more in polystyrene, polyacrylic acid or the phenolic aldehyde.
6. the method for employing Zeo-karb separation and purification Nuciferine according to claim 1, it is characterized in that: the cation composition of eluent is H
+, K
+, Na
+, NH
4 +In the mineral ion one or more.
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|---|---|---|---|
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|---|---|---|---|
| CN2007100094653A CN101139321B (en) | 2007-09-01 | 2007-09-01 | Method for separating and purifying nuciferine by employing cationic ion-exchange resin |
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| CN101139321B true CN101139321B (en) | 2010-12-08 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101647828B (en) * | 2008-08-13 | 2012-11-28 | 代龙 | Method for separating total alkaloid from sophora flavescens ait by using ion exchange resin |
| CN102442949A (en) * | 2010-10-09 | 2012-05-09 | 苏州宝泽堂医药科技有限公司 | Method for extracting nuciferine from lotus leaves |
| CN105111144A (en) * | 2015-09-30 | 2015-12-02 | 桂林三宝药业有限公司 | Method of extracting nuciferine from lotus leaves |
| CN107056705B (en) * | 2017-06-06 | 2023-11-07 | 陕西理工大学 | Energy-saving device and method for separating nuciferine |
| CN110343069A (en) * | 2019-07-22 | 2019-10-18 | 陕西康城药业股份有限公司 | The method and its application of Nuciferine in a kind of enzymatic extraction purification lotus leaf |
| CN113444043A (en) * | 2020-03-27 | 2021-09-28 | 福建中医药大学 | Lotus leaf alkaloid and extraction and purification method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1296774A (en) * | 1999-11-22 | 2001-05-30 | 李雪涛 | Process for extracting nutrients from lotus and its products |
| CN1923829A (en) * | 2006-09-21 | 2007-03-07 | 福州大学 | Preparation method and use of separating and purifying lotus leaf flavone and lotus leaf alkaloid by employing polyamide |
| CN101007064A (en) * | 2006-09-09 | 2007-08-01 | 福州大学 | Isolation and purification method of lotus leaf extract by macroporous resin and its application thereof |
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2007
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1296774A (en) * | 1999-11-22 | 2001-05-30 | 李雪涛 | Process for extracting nutrients from lotus and its products |
| CN101007064A (en) * | 2006-09-09 | 2007-08-01 | 福州大学 | Isolation and purification method of lotus leaf extract by macroporous resin and its application thereof |
| CN1923829A (en) * | 2006-09-21 | 2007-03-07 | 福州大学 | Preparation method and use of separating and purifying lotus leaf flavone and lotus leaf alkaloid by employing polyamide |
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