CN103788153A - Method for resolution of isomers of paeoniflorin and albiflorin by simulated moving bed chromatography - Google Patents
Method for resolution of isomers of paeoniflorin and albiflorin by simulated moving bed chromatography Download PDFInfo
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- CN103788153A CN103788153A CN201210429817.1A CN201210429817A CN103788153A CN 103788153 A CN103788153 A CN 103788153A CN 201210429817 A CN201210429817 A CN 201210429817A CN 103788153 A CN103788153 A CN 103788153A
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Abstract
The invention discloses a method for resolution of isomers of paeoniflorin and albiflorin by simulated moving bed chromatography. The method of the invention is characterized in that a simulated moving bed chromatography system is adopted; the stationary phase is a reversed-phase C18 filler; the mobile phase is a mixed solution of methanol and water; resolution of the isomers of paeoniflorin and albiflorin is carried out at a reversed-phase condition to obtain high-purity albiflorin and paeoniflorin. The simulated moving bed chromatography system realizes continuous production, and is high in automation degree and high in production efficiency.
Description
Technical field
The present invention relates to a kind of disassemble technique of isomers medicine, particularly the simulated moving bed chromatographic separation process of isomer peoniflorin and lactone glucoside of Radix Paeoniae.
Background technology
The root of herbaceous peony be ranunculaceae plant Chinese herbaceous peony remove crust dry root, have anti-inflammatory, antiviral, separate spasm, ease pain and protect the multiple pharmacologically actives such as liver.Peoniflorin is the main active ingredient in the root of herbaceous peony, belongs to monoterpene glycosides, and that peoniflorin has is hypoglycemic, protection cardiovascular and cerebrovascular, regulate immunity system, the effect such as antitumor.Lactone glucoside of Radix Paeoniae is the activeconstituents in the root of herbaceous peony equally, also belongs to monoterpene glycosides, and to DNA, division has faint restraining effect and anticonvulsant action etc. to lactone glucoside of Radix Paeoniae.From the structure of peoniflorin and lactone glucoside of Radix Paeoniae, both have identical molecular formula, and relative molecular mass is identical, and structure difference belongs to typical isomers.In recent years, more and more extensive about the pharmacological research of peoniflorin and lactone glucoside of Radix Paeoniae, therefore, the increase in demand of peoniflorin and lactone glucoside of Radix Paeoniae monomer.Traditional peony root total glycosides extract is the mixture that contains the two, therefore, the fractionation of this medicine is had to great practical significance.
Summary of the invention
The object of this invention is to provide a kind of method of isomer peoniflorin and the simulation moving-bed fractionation of lactone glucoside of Radix Paeoniae enantiomorph.The technical scheme adopting is for achieving the above object as follows: the simulation moving-bed method for splitting of a kind of isomer peoniflorin and lactone glucoside of Radix Paeoniae enantiomorph, it is characterized in that with C18 as stationary phase, with the mixing solutions of first alcohol and water be moving phase, from isomer peoniflorin and lactone glucoside of Radix Paeoniae racemoid, split out highly purified peoniflorin and lactone glucoside of Radix Paeoniae by simulated moving bed system, comprise the following steps:
(1), isomer peoniflorin and lactone glucoside of Radix Paeoniae racemic modification are dissolved in moving phase, concentration is: 0 ~ 100g/L;
(2), with simulation moving-bed fractionation isomer peoniflorin and lactone glucoside of Radix Paeoniae;
(3), concentrated, recrystallization obtains highly purified two kinds of peoniflorins and lactone glucoside of Radix Paeoniae enantiomorph.
The present invention has following technique effect: the present invention adopts simulated moving bed system, from the isomer of peoniflorin and lactone glucoside of Radix Paeoniae, split out peoniflorin and the lactone glucoside of Radix Paeoniae enantiomorph with optical purity, technique is simple, produce continuous and automatic, constant product quality, solvent adopts the mixture of first alcohol and water, recoverable, pollution-free, realize cleaner production.
Embodiment
1, equipment and condition are selected
Adopt simulated moving bed chromatography system, this system comprises wash-out pump, sampling pump, extraction pump, chromatographic column, magnetic valve, check valve, thermostat and PLC central controller and computer composition.Sample solution and elutriant are respectively from sample liquid entrance and elutriant entrance injected system, two enantiomorphs of peoniflorin and lactone glucoside of Radix Paeoniae flow out respectively from raffinate and two outlets of extracting solution, often sample liquid and elutriant entrance at regular intervals, extracting solution and raffinate outlet switch to next chromatographic column along the mobile direction of moving phase.
2, chromatographic column filler and moving phase (solvent) are selected
Take C18 as stationary phase, filler granularity is 1 ~ 150um, and particulate is less, and size distribution is narrower, is more conducive to separate; But more mini system pressure is larger for particle diameter, and optimum particle size range is 20 ~ 40um; Moving phase (solvent) is the mixing solutions of first alcohol and water.
3, separating step
A, sample dissolve by moving phase, concentration is 0 ~ 100g/L, chromatographic system is made up of 4 ~ 24 preparative columns, be divided into 4 districts, the more separation of chromatographic column number are better, but complexity and the system pressure of system are higher, optimal is 8 ~ 12, by the controller of simulated moving bed chromatography system, regularly control the switching of magnetic valve, injection port, extraction liquid outlet and residual solution outlet are regularly converted along the direction of moving phase, make two enantiomorphs of peoniflorin and lactone glucoside of Radix Paeoniae from extracting solution and two outlet outflow systems of raffinate;
B, the product solution obtaining, obtain the qualified product of purity more than 95% through concentrated, recrystallization;
C, inspection after construction
Moving phase: methyl alcohol: water=30:70
Flow velocity: 1.0mL/min
Pump: Jiangsu Chinese nation science and technology is analyzed pump
Chromatographic column: C18 post (4.6*250mm)
Detector: Jiangsu Chinese nation science and technology UV-detector
Detect wavelength: 230nm
Further illustrate the present invention below in conjunction with example:
Separate instance one
1, the preparation of sample: sample dissolves by moving phase, making concentration is 5g/L, for subsequent use after the organic membrane filtration of 0.45um;
2, the selection of simulation moving-bed parameter: determine that parameter is as follows: sample introduction flow velocity 0.4mL/min, elution flow rate 2.0mL/min, extracting solution flow velocity 1.4mL/min, raffinate flow velocity 1.0mL/min, switching time 15min, temperature is controlled at 20-30 ℃;
3, product-collecting: after simulated moving bed system is stable, collect product from two outlets respectively, obtain the finished product after concentrating under reduced pressure, recrystallization;
4, inspection after construction: after the product obtaining dissolves by moving phase, the purity that detects two exported product peoniflorins and lactone glucoside of Radix Paeoniae with analysis condition is respectively 98.6% and 99.1%;
Per kilogram stationary phase can be produced peoniflorin and the each 0.32kg of lactone glucoside of Radix Paeoniae every day, and moving phase consumption is 25L/kg, and the rate of recovery is 96.2%.
Separate instance two
1, the preparation of sample: sample dissolves by moving phase, making concentration is 10g/L, for subsequent use after the organic membrane filtration of 0.45um;
2, the selection of simulation moving-bed parameter: determine that parameter is as follows: sample introduction flow velocity 1.0mL/min, elution flow rate 4.0mL/min, extracting solution flow velocity 2.8mL/min, raffinate flow velocity 2.2mL/min, switching time 12min, temperature is controlled at 20-30 ℃;
3, product-collecting: after simulated moving bed system is stable, collect product from two outlets respectively, obtain the finished product after concentrating under reduced pressure, recrystallization;
4, inspection after construction: after the product obtaining dissolves by moving phase, the purity that detects two exported product peoniflorins and lactone glucoside of Radix Paeoniae with analysis condition is respectively 97.7% and 98.3%;
Per kilogram stationary phase can be produced peoniflorin and the each 1.95kg of lactone glucoside of Radix Paeoniae every day, and moving phase consumption is 70.4L/kg, and the rate of recovery is 95.8%.
Separate instance three
1, the preparation of sample: sample dissolves by moving phase, making concentration is 20g/L, for subsequent use after the organic membrane filtration of 0.45um;
2, the selection of simulation moving-bed parameter: determine that parameter is as follows: sample introduction flow velocity 1.5mL/min, elution flow rate 7.0mL/min, extracting solution flow velocity 5.0mL/min, raffinate flow velocity 3.5mL/min, switching time 10min, temperature is controlled at 20-30 ℃;
3, product-collecting: after simulated moving bed system is stable, collect product from two outlets respectively, obtain the finished product after concentrating under reduced pressure, recrystallization;
4, inspection after construction: after the product obtaining dissolves by moving phase, the purity that detects two exported product peoniflorins and lactone glucoside of Radix Paeoniae with analysis condition is respectively 96.5% and 97.2%;
Per kilogram stationary phase can be produced peoniflorin and the each 4.12kg of lactone glucoside of Radix Paeoniae every day, and moving phase consumption is 92.5L/kg, and the rate of recovery is 95.5%.
Above-mentioned embodiment is used for the present invention that explains, rather than limits the invention, and in the protection domain of spirit of the present invention and claim, any modification and change that the present invention is made, all fall into protection scope of the present invention.
Claims (5)
1. the simulated moving bed chromatography separation separating method of an isomer peoniflorin and lactone glucoside of Radix Paeoniae, it is characterized in that: adopt simulated moving bed chromatography (being called for short SMBC) separation system, wash-out pumping capacity 0～100mL/min in system, pressure 0～10Mpa, sampling pump flow 0～50mL/min, pressure 0～10Mpa, extraction pumping capacity 0～100mL/min, pressure 0～10Mpa, 20～35 ℃ of working temperatures, chromatographic column filler is C18, filler granularity 20～40um, moving phase is the mixing solutions of first alcohol and water, and the separating step of the method is as follows:
A, isomer peoniflorin and lactone glucoside of Radix Paeoniae dissolve by moving phase, concentration is 0～100g/L, enter chromatographic system by sampling pump, chromatographic system is made up of 4～24 preparative columns, be divided into Si Ge district, there is 1～6 pillar in every district, and wherein I district is positioned between elutriant entrance and extracting liquid outlet, and Ci district realizes the desorb of peoniflorin; II district is positioned between extracting liquid outlet and injection port, and Ci district makes peoniflorin Adsorption and desorption, concentrated repeatedly; III district is positioned at Ci district between injection port and raffinate outlet and obtains lactone glucoside of Radix Paeoniae; IV district is positioned between raffinate outlet and elutriant entrance, and the elutriant in III district enters into this district's reusable edible on the one hand, and JiangIII district and I separate out on the other hand, prevent that the lactone glucoside of Radix Paeoniae in raffinate from entering into I district;
B, obtain two enantiomorph products, through concentrated recrystallization, obtaining purity is more than 95% qualified product.
2. the simulated moving bed chromatographic separation process of isomer peoniflorin according to claim 1 and lactone glucoside of Radix Paeoniae, is characterized in that described moving phase is the mixing solutions of first alcohol and water.
3. the simulated moving bed chromatographic separation process of isomer peoniflorin according to claim 1 and lactone glucoside of Radix Paeoniae, the concentration that it is characterized in that entering simulated moving bed system is 0～100g/L, sample introduction flow velocity is 0～50mL/min, eluent flow rate is 0～100mL/min, extraction liquid flow velocity is 0～100mL/min, and raffinate flow velocity is 0～100mL/min.
4. the simulated moving bed chromatographic separation process of isomer peoniflorin according to claim 1 and lactone glucoside of Radix Paeoniae, is characterized in that the time of described regular switching solenoid valve is: 8～20min.
5. the simulated moving bed chromatographic separation process of isomer peoniflorin according to claim 1 and lactone glucoside of Radix Paeoniae, is characterized in that the service temperature of described simulated moving bed chromatography system is 20～30 ℃.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113943332A (en) * | 2021-09-28 | 2022-01-18 | 沈阳化工研究院有限公司 | Method for preparing high-purity albiflorin by utilizing dynamic axial compression chromatography |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113943332A (en) * | 2021-09-28 | 2022-01-18 | 沈阳化工研究院有限公司 | Method for preparing high-purity albiflorin by utilizing dynamic axial compression chromatography |
| CN113943332B (en) * | 2021-09-28 | 2023-10-20 | 沈阳化工研究院有限公司 | Method for preparing high-purity paeoniflorin by dynamic axial compression chromatography |
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Application publication date: 20140514 |