CN101607975A - The method of separating and preparing peony lactone glucoside by simulation moving bed chromatography - Google Patents
The method of separating and preparing peony lactone glucoside by simulation moving bed chromatography Download PDFInfo
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- CN101607975A CN101607975A CNA2009101006803A CN200910100680A CN101607975A CN 101607975 A CN101607975 A CN 101607975A CN A2009101006803 A CNA2009101006803 A CN A2009101006803A CN 200910100680 A CN200910100680 A CN 200910100680A CN 101607975 A CN101607975 A CN 101607975A
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Abstract
The present invention relates to the separating and purifying method of natural drug, relate in particular to a kind of method of separating and preparing peony lactone glucoside by simulation moving bed chromatography.The method of separating and preparing peony lactone glucoside by simulation moving bed chromatography, this method adopts the Radix Paeoniae Alba total glucosides extract as raw material, application simulation moving-bed chromatographic separating and preparing peony lactone glucoside, the stationary phase of simulated moving bed chromatography adopts C18 silica gel, the mixing solutions of moving phase employing methyl alcohol or acetonitrile and water, formic acid, Virahol, percentage meter by volume in the mixing solutions: methyl alcohol or acetonitrile 10%～50%, water 50%～90%, formic acid 0～1%, Virahol 0～2%, the summation of each above-mentioned component are 100%.The yield height of peony lactone glycoside product of the present invention, purity reaches more than 90%.Because the simulated moving bed chromatography process is a successive processes, can improve the automatization level and the production efficiency of production, and production environment is improved greatly, has really realized cleaner production.
Description
Technical field
The present invention relates to the separating and purifying method of natural drug, relate in particular to a kind of method of separating and preparing peony lactone glucoside by simulation moving bed chromatography.
Background technology
Lactone glucoside of Radix Paeoniae is as the characteristic component that has in the Radix Paeoniae Alba total glucosides (TGP) of anti-inflammatory, antiulcer agent and immunoregulation effect, extracts to obtain from the root of herbaceous peony.Because in the root of herbaceous peony, except lactone glucoside of Radix Paeoniae, also contain various ingredients such as multiple glycoside composition such as peoniflorin, Hydroxy peoniflorin, benzoylpaeoniflorin and benzoyl Hydroxy peoniflorin and other impurity, so in the production process of lactone glucoside of Radix Paeoniae, the step of most critical is separated purification exactly.The normal refining means that adopt in pharmaceutical industries comprise silica gel column chromatography, resin column chromatography, methods such as gel filtration chromatography at present.Above equipment is simple, and cost is low, but weak point is that isolating efficient is lower, and the utilization ratio of moving phase and stationary phase is lower, and the cost height yields poorly, and is not suitable for separating for the complicated material of composition.In addition, the contradiction between product purity and the yield can not get solving in column chromatography.Keep purity, have only the sacrifice yield, this low yield will cause expensive.
Phase early 1970s, American UOP company has developed chromatographic technique [the simulated moving bed chromatography technology and the application thereof of simulation moving-bed (SMBC) principle, chromatogram, the 22nd volume, P111～115,2004 year March], this technology is not moving after making the absorbent particles filling, by the method that raw material is imported and exported and the import and export of product liquid are constantly switched, form absorbent particles and simulate moving of stationary phase relative to countercurrent movement with moving phase.This technological merit is can continuous operation, and filler more effectively utilizes, and solvent consumption reduces in a large number, and the product extent of dilution of collecting is little.The development of SMBC technology is thereafter the sugar industry in the food from petrochemical industry, enters pharmaceutical field in 20 end of the centurys, and has obtained using fast and developing.But, do not see open report yet for the simulated moving bed chromatography preparation technology of lactone glucoside of Radix Paeoniae.
Summary of the invention
For the technological deficiency that solves lactone glucoside of Radix Paeoniae separation and Extraction cost height, yields poorly, the object of the present invention is to provide the method for application simulation mobile bed chromatic separating and preparing peony lactone glucoside, this method continuous production has improved the purity and the yield of product, and has reduced production costs.
In order to realize above-mentioned purpose, the present invention has adopted following technical scheme:
The method of separating and preparing peony lactone glucoside by simulation moving bed chromatography, this method adopts the Radix Paeoniae Alba total glucosides extract as raw material, application simulation moving-bed chromatographic separating and preparing peony lactone glucoside, the stationary phase of simulated moving bed chromatography adopts C18 silica gel, moving phase adopts the mixing solutions of methyl alcohol or acetonitrile and water, formic acid, Virahol, percentage meter by volume in the mixing solutions:
Methyl alcohol or acetonitrile 10%～50%
Water 50%～90%
Formic acid 0～1%
Virahol 0～2%
The summation of each above-mentioned component is 100%.
Can add formic acid and Virahol in the moving phase of the present invention, in order to adjust the peak type of lactone glucoside of Radix Paeoniae, reduce hangover, make it and peoniflorin under the bigger situation of sample introduction concentration, can reach baseline separation preferably, thereby obtain the higher lactone glucoside of Radix Paeoniae of purity by SMBC.As preferably, ratio meter by volume in the above-mentioned mixing solutions:
Methyl alcohol or acetonitrile 10%～50%
Water 50%～90%
Formic acid 0.05%～0.5%
Virahol 1%～2%.
The summation of each above-mentioned component is 100%.
Above-mentioned Radix Paeoniae Alba total glucosides extract can extract from white Peony Root by the extraction means of purification and obtain, and main component is lactone glucoside of Radix Paeoniae and peoniflorin.As preferably, the purity of Radix Paeoniae Alba total glucosides extract is 40%～90%.
As preferably, the above-mentioned isolating Radix Paeoniae Alba total glucosides extract of simulated moving bed chromatography that enters adopts dissolve with methanol, and the concentration of dissolving back Radix Paeoniae Alba total glucosides extract is 10～200mg/mL.
As preferably, above-mentioned simulation moving-bedly be made up of 4～8 root chromatogram columns, chromatographic column is divided four zones, and every district is by 1～2 identical chromatographic column series connection.As preferably, sample introduction flow velocity U
pBe 2～20ml/min; Eluent flow rate U
EBe 5～40ml/min; Raffinate flow velocity U
RBe 2～20ml/min; Extraction liquid flow velocity U
XBe 5～30ml/min; Switching time T
sBe 0.5～30min.
As preferably, the service temperature of above-mentioned simulated moving bed chromatography system is 20～60 ℃.Preferred again, the service temperature of simulated moving bed chromatography system is 20～40 ℃.
The present invention has been owing to adopted above-mentioned technical scheme, the yield height of peony lactone glycoside product, and purity reaches more than 90%.Because the simulated moving bed chromatography process is a successive processes, can improve the automatization level and the production efficiency of production, and production environment is improved greatly, has really realized cleaner production.
Description of drawings
Fig. 1 is the structural representation of simulated moving bed chromatography of the present invention.
Fig. 2 is the HPLC collection of illustrative plates of lactone glucoside of Radix Paeoniae of the present invention.
Embodiment
Below the specific embodiment of the present invention is done a detailed description.The method of simulated moving bed chromatography separating and preparing peony lactone glucoside, this method comprises the steps:
One, the preparation of sample solution
Separate with silica gel column chromatography by alcohol reflux, from white Peony Root, make the Radix Paeoniae Alba total glucosides extract (TGP) that contains peoniflorin 80%.The TGP sample that obtains is dissolved in the methanol solution, and sedimentation gets the solution that concentration is 100mg/mL through 0.45 μ m membrane filtration, with this sample introduction liquid as SMBC.This process can be removed the impurity of part irreversible adsorption, thereby prevents its pollution to chromatographic column in the SMBC system, prolongs the work-ing life of chromatographic column.
Two, the composition of chromatographic column filling and moving phase
With the homogenate method load 8 root chromatogram columns (10mm * 100mm), filler is anti-phase C18 silica gel, particle diameter 5～10 μ m, aperture 100～
The volume ratio of methyl alcohol and water, formic acid, Virahol is 30: 70: 0.1 in the moving phase: 1.5.
Certainly, above-mentioned moving phase also can adopt the mixed solution of methyl alcohol and water, and the volume ratio of methyl alcohol and water is 30: 70.Perhaps, the mixed solution of moving phase employing methyl alcohol and water, formic acid, the volume ratio of methyl alcohol and water, formic acid is 30: 70: 1.
Three, simulated moving bed chromatography system (SMBC)
The SMBC system comprises sampling pump, wash-out liquid pump, extraction pump, raffinate pump and recycle pump, rotary valve and chromatographic column.As shown in Figure 1, Arabic numerals are the chromatographic column numbering, and sample solution and elutriant inject chromatographic system (as Fig. 1 solid arrow indication position) from sample liquid inlet and elutriant inlet respectively.At regular intervals, sample liquid and elutriant inlet, extraction liquid and raffinate outlet switch to next root chromatogram column outlet (as Fig. 1 dotted arrow indication position) along the moving phase direction simultaneously.Through the separation of SMBC, can obtain highly purified lactone glucoside of Radix Paeoniae from the extraction liquid outlet, then can obtain the peoniflorin of higher degree from the raffinate outlet.
Four, simulated moving bed chromatography parameter
Simulation moving-bed in the inventive method formed 4 zones by 8 chromatographic columns, switches through magnetic valve and changes opening for feed, discharge port position.Sample introduction flow velocity: U
p=4～10ml/min; Eluent flow rate: U
E=10～20ml/min; Raffinate flow velocity: U
R=5～10ml/min; Extraction liquid flow velocity: U
X=10～20ml/min; Switching time: T
s=1～5min.Operating temperature range is 20～40 ℃.
Five, concentrate
Extraction liquid and raffinate are concentrated into nothing alcohol flavor with the film rotatory evaporator respectively, wash out the back with ethanol and dry to constant weight at vacuum drying oven.
Six, inspection after construction
Agilent 1100 highly effective liquid phase chromatographic systems, diode-array detector, Hypersil-C
18Post (250mm * 4.6mm i.d, 5 μ m), moving phase are acetonitrile and water (volume ratio is 30: 70), flow velocity 1.0mlmL
-1, 40 ℃ of column temperatures detect wavelength 230nm, detect collection of illustrative plates as shown in Figure 2.Purity by lactone glucoside of Radix Paeoniae in the external standard method finished product is more than 90%.
Claims (8)
1. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography, it is characterized in that: this method adopts the Radix Paeoniae Alba total glucosides extract as raw material, application simulation moving-bed chromatographic separating and preparing peony lactone glucoside, the stationary phase of simulated moving bed chromatography adopts C18 silica gel, moving phase adopts the mixing solutions of methyl alcohol or acetonitrile and water, formic acid, Virahol, percentage meter by volume in the mixing solutions:
Methyl alcohol or acetonitrile 10%～50%
Water 50%～90%
Formic acid 0～1%
Virahol 0～2%
The summation of each above-mentioned component is 100%.
2. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography according to claim 1 is characterized in that in the mixing solutions ratio meter by volume:
Methyl alcohol or acetonitrile 10%～50%
Water 50%～90%
Formic acid 0.05%～0.5%
Virahol 1%～2%.
The summation of each above-mentioned component is 100%.
3. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography according to claim 1 and 2 is characterized in that: the Radix Paeoniae Alba total glucosides extract is for extracting from white Peony Root and obtain by extracting means of purification, and purity is 40%～90%.
4. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography according to claim 1 and 2, it is characterized in that: enter the isolating Radix Paeoniae Alba total glucosides extract of simulated moving bed chromatography and adopt dissolve with methanol, the concentration of dissolving back Radix Paeoniae Alba total glucosides extract is 10～100mg/mL.
5. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography according to claim 1 and 2 is characterized in that: simulation moving-bedly be made up of 4～8 root chromatogram columns, chromatographic column is divided four zones, and every district is by 1～2 identical chromatographic column series connection.
6. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography according to claim 5 is characterized in that: sample introduction flow velocity U
pBe 2～20ml/min; Eluent flow rate U
EBe 5～40ml/min; Raffinate flow velocity U
RBe 2～20ml/min; Extraction liquid flow velocity U
XBe 5～30ml/min; Switching time T
SBe 0.5～30min.
7. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography according to claim 5, it is characterized in that: the service temperature of simulated moving bed chromatography system is 20～60 ℃.
8. the method for separating and preparing peony lactone glucoside by simulation moving bed chromatography according to claim 7, it is characterized in that: the service temperature of simulated moving bed chromatography system is 20～40 ℃.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336792A (en) * | 2010-07-22 | 2012-02-01 | 辽宁科技大学 | Three-zone simulated moving bed chromatography method for separating and purifying paeoniflorin |
| WO2012019373A1 (en) * | 2010-08-10 | 2012-02-16 | 张作光 | Method for preparing paeoniflorin and albiflorin |
| US9453041B2 (en) | 2010-11-10 | 2016-09-27 | Zuoguang Zhang | Method for preparing albiflorin and paeoniflorin |
| CN111153944A (en) * | 2019-09-26 | 2020-05-15 | 内蒙古昶辉生物科技股份有限公司 | Method for extracting stevioside by adopting simulated moving bed chromatography |
| CN111153950A (en) * | 2019-09-26 | 2020-05-15 | 内蒙古昶辉生物科技股份有限公司 | Method for extracting high-purity stevioside by adopting simulated moving bed chromatography |
| CN113209670A (en) * | 2021-06-23 | 2021-08-06 | 内蒙古工业大学 | Xylo-oligosaccharide separation and purification system and process in sequential simulated moving bed coupling crystallization process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1288438C (en) * | 2003-10-30 | 2006-12-06 | 鞍山科技大学 | Method for purifying ginkgo inner ester B by analogue moving bed chromatograph |
| CN100528857C (en) * | 2007-05-24 | 2009-08-19 | 江苏汉邦科技有限公司 | Simulated four-area moving bed chromatographic process for separating and purifying aloe flavone |
| CN100586449C (en) * | 2008-06-13 | 2010-02-03 | 宁波立华制药有限公司 | Method for preparing white peony root total glycosides extract |
-
2009
- 2009-07-16 CN CN2009101006803A patent/CN101607975B/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336792A (en) * | 2010-07-22 | 2012-02-01 | 辽宁科技大学 | Three-zone simulated moving bed chromatography method for separating and purifying paeoniflorin |
| WO2012019373A1 (en) * | 2010-08-10 | 2012-02-16 | 张作光 | Method for preparing paeoniflorin and albiflorin |
| US9453041B2 (en) | 2010-11-10 | 2016-09-27 | Zuoguang Zhang | Method for preparing albiflorin and paeoniflorin |
| CN111153944A (en) * | 2019-09-26 | 2020-05-15 | 内蒙古昶辉生物科技股份有限公司 | Method for extracting stevioside by adopting simulated moving bed chromatography |
| CN111153950A (en) * | 2019-09-26 | 2020-05-15 | 内蒙古昶辉生物科技股份有限公司 | Method for extracting high-purity stevioside by adopting simulated moving bed chromatography |
| CN113209670A (en) * | 2021-06-23 | 2021-08-06 | 内蒙古工业大学 | Xylo-oligosaccharide separation and purification system and process in sequential simulated moving bed coupling crystallization process |
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