CN105801549A - Simulated moving bed chromatography separation method of naringenin antipode - Google Patents
Simulated moving bed chromatography separation method of naringenin antipode Download PDFInfo
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- CN105801549A CN105801549A CN201610317990.0A CN201610317990A CN105801549A CN 105801549 A CN105801549 A CN 105801549A CN 201610317990 A CN201610317990 A CN 201610317990A CN 105801549 A CN105801549 A CN 105801549A
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- naringenin
- raffinate
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- LCUSPTNLOPKCFZ-UHFFFAOYSA-N Oc1cc(OC(CC2=O)C3C#CC(O)=CCC4C3=C4)c2c(O)c1 Chemical compound Oc1cc(OC(CC2=O)C3C#CC(O)=CCC4C3=C4)c2c(O)c1 LCUSPTNLOPKCFZ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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Abstract
The invention provides a simulated moving bed chromatography separation method of a naringenin antipode. The separation method comprises the following steps: with spherical silica gel coated with amylose-tri(3,5-dimethylphenyl carbamate) on the surface as a chiral stationary phase and methanol as a mobile phase, dissolving the naringenin antipode with methanol to obtain a sample solution; and performing simulated moving bed chromatography separation of the sample solution to obtain single-configuration S-(-)-naringenin and R-(+)-naringenin respectively. In the invention, a simulated moving bed chromatography system is adopted, and an optical-purity naringenin single antipode is separated from naringenin raceme; the technology is simple, the production is continuous and automatic, and the product quality is stable; and moreover, the solvent is methanol which can be recycled, thus pollution is avoided, and clean production is truly realized.
Description
(1) technical field
The present invention relates to the fractionation technology of chiral drug, particularly to the simulated moving bed chromatography separation side of dividing of a kind of naringenin enantiomer
Method.
(2) background technology
Naringenin (another name Naringenin；4', 5,7-trihydroxyflavone；Naringenin) be naringin glycoside unit, belong to flavanone
Compound, molecular formula is C15H12O5, molecular weight is 272.25g/mol, is white needle-like crystals under normality, fusing point 260 DEG C,
It is dissolved in ethanol, ether and benzene, is practically insoluble in water.Molecular structural formula is:
Naringenin has antibacterial, antiinflammatory, removing free radical, antioxidation, eliminating phlegm and stopping cough, blood fat reducing, anticancer antitumor, spasmolytic
With function of gallbladder promoting, prevent and treat the effect such as hepatopathy, anti-platelet clotting, anti-medicated porridge sample arteriosclerosis, doctor can be widely used in
The field such as medicine, food (Lv Aixin, in magnificence, Zhao Zhi is strong. naringenin progress [J]. and Agriculture of Anhui science, 2011,39 (13):
7734-7735.)。
Naringenin is usually and extracts from natural plants, and one is extraction, and another kind is naringin Hydrolyze method.Naringenin is being changed
The research of molecularly imprinted polymer is can be used as on；It it is a kind of environmentally friendly novel agrochemical in terms of pesticide；Clinically may be used
Treating multiple disease, additionally its a kind of function food additive, can treat owing to blood gallbladder too much in blood of human body is solid
The disease that alcohol and triglyceride cause.So for ensureing safe medication and reducing the side effect of food, splitting naringenin enantiomer tool
There is realistic meaning.The method of existing fractionation naringenin enantiomer is mainly high performance liquid chromatography and supercritical chromatography.Sun Ya
Men etc. use high performance liquid chromatography to split naringenin enantiomer, in chiralpak AD-H chromatographic column (250mm × 4.6
Mm, 5 μm) on, with normal hexane: isopropanol: trifluoroacetic acid=75:25:0.1 is flowing phase, in column temperature 35 DEG C, detection
Under the chromatographic condition of wavelength 290nm, it is achieved that the fractionation of naringenin enantiomer, but preparation amount is few, the big (grandson of solvent-oil ratio
Sub-man, Li Tong, Banjermasin. high performance liquid chromatography splits flavone compound enantiomer [J]. and analyze test and learn
Report, 2013,32 (3): 346-350.)；Naringenin enantiomer is split on Supercritical fluid chromatography by Raffaella Gaggeri, with
CO2/ methanol (75:25, v/v), as flowing phase, flow 4.00mL/min, temperature 30 DEG C, detects wavelength 290nm,
Employing supercritical chromatography produces, and naringenin Chiral Separation process is loaded down with trivial details, and system stability is poor, and can not realize the most raw
Produce (the .Quick development of an analytical such as Raffaella Gaggeria, Daniela Rossia, Simona Collina
enantioselective high performance liquid chromatography separation and preparative scale-up for
The flavonoid Naringenin[J].Journal of Chromatography A,2011,1218:5414-5422.)。
(3) summary of the invention
For the deficiencies in the prior art, the invention provides a kind of simulated moving bed chromatography separation and divide the producer of naringenin enantiomer
Method, simulated moving bed chromatography separation divides naringenin enantiomer to be that one can realize continuous prodution, reduces solvent-oil ratio and improve
A kind of separation method of productivity.
The present invention adopts the following technical scheme that
The simulated moving bed chromatography separation of a kind of naringenin enantiomer divides method, described method for splitting to comprise the steps:
(1) preparation naringenin enantiomer sample liquid: naringenin enantiomer methanol is dissolved, obtains sample liquid, gained sample
In liquid, the concentration of naringenin enantiomer is 5～80g/L (preferably 20～40g/L)；
(2) simulated moving bed chromatography separation divides naringenin enantiomer:
The spherical silica gel of amylose-three (3,5-dimethylphenylamino formic acid fat) it is coated with as chiral stationary phase (grain using surface
Degree is 5～75um, and preferably 20～40um are commercially available), methanol is as flowing phase；
Chromatographic system mainly by: be provided with eluting pump eluent entrance, be provided with extraction pump extract outlet, be provided with sampling pump
Sample liquid entrance, be provided with raffinate pump raffinate outlet, be provided with detector eluent outlet and 4～24 (preferably 8～16)
Chromatographic column forms, and is divided into tetra-districts of I, II, III, IV, and there is 1～6 (preferably 2～4) pillar in every district, and wherein I district is positioned at and washes
The desorbing of (realize in this interval S-(-)-naringenin between de-liquid entrance and extract outlet), II district is positioned at extract outlet and sample
(realize in this district S-(-)-naringenin Adsorption and desorption repeatedly, concentration between product liquid entrance), III district is positioned at sample liquid entrance and extraction
(obtain at this R-(+)-naringenin between remaining liquid outlet), IV district is positioned at (on the one hand III between raffinate outlet and eluent outlet
The eluent in district enters into this district's reusable edible, is on the other hand separated out with I in III district, prevent R-in raffinate (+)-Pericarpium Citri grandis
Element enters into I district)；
The sample liquid that step (1) is prepared and eluant methanol respectively from sample liquid entrance and eluent entrance by sampling pump and
Eluting infusion enters chromatographic system, and the outlet of sample liquid entrance, eluent entrance, extract, raffinate outlet are simultaneously along eluting liquid stream
Dynamic direction periodically switches to next root chromatogram column, containing S-(-) extract of-naringenin and containing R-(+) raffinate of-naringenin divides
Not from extract outlet and raffinate outlet outflow system, collect extract and raffinate, the most concentrated, dry, respectively
S-(-)-naringenin and R-(+)-naringenin to single configuration；
The Parameter Conditions of fractured operation is: sample liquid flow velocity 1～10mL/min, eluent flow rate 1～100mL/min, extract flow
Speed 1～50mL/min, raffinate flow velocity 1～50mL/min, it is spaced 1～10min switching time.
The operation temperature of simulated moving bed chromatography system of the present invention is 10～40 DEG C.
The preferably Parameter Conditions of fractured operation is: sample liquid flow velocity 2～8mL/min, eluent flow rate 5～80mL/min, extract
Flow velocity 3～40mL/min, raffinate flow velocity 3～40mL/min, it is spaced 2～8min switching time.
The more preferably Parameter Conditions of fractured operation is: sample liquid flow velocity 2～6mL/min, eluent flow rate 5～50mL/min, extraction
Take flow velocity 5～30mL/min, raffinate flow velocity 5～30mL/min, be spaced 2～5min switching time.
Method isolated single configuration S-(-)-naringenin and R-(+)-naringenin is divided according to simulated moving bed chromatography separation of the present invention,
And analyze detection, purity >=98%, the response rate >=95% by high performance liquid chromatography (HPLC).
There is advantages that the present invention uses simulated moving bed chromatography system, tear open from naringenin racemic modification
Separating the naringenin single enantiomer with optical purity, technique is simple, produces continuous and automatic, constant product quality, solvent
Employing methanol, recoverable, pollution-free, it is truly realized cleaning and produces.
(4) accompanying drawing explanation
Fig. 1 is the simulated moving bed chromatography system structure chart of the present invention.
(5) detailed description of the invention
Below by way of specific embodiment, the invention will be further described, but protection scope of the present invention is not limited to that.
1. equipment and condition select
Using simulated moving bed chromatography system, this system includes eluting pump, sampling pump, extraction pump, raffinate pump, detector, color
Spectrum post and pneumatic operated valve, check valve (as shown in Figure 1).Sample liquid and eluent are respectively from sample liquid entrance and eluent entrance
Entering chromatographic system by sampling pump and eluting infusion, two enantiomer of naringenin export stream from raffinate and extract two the most respectively
Go out system (such as Fig. 1 arrow pointed location).At regular intervals, sample liquid and eluent entrance, raffinate and extract go out
Mouth switches to next root chromatogram column along flowing phase flow direction simultaneously.
2. chromatographic column filler and flowing select mutually
Chromatographic column is purchased from Daicel medicine chiral technology (Shanghai) Co., Ltd. Chiralpak AD 100*10cm 10um, with table
Face is coated with the spherical silica gel of amylose-three (3,5-dimethylphenylamino formic acid fat) as chiral stationary phase, filler granularity
Being 5～75um, microgranule is the least, and particle diameter distribution is the narrowest, is more conducive to separating；But particle diameter more mini system pressure is the biggest, to simulation
Moving bed system requirements is higher.Optimum particle size range is 20～40um.Flowing phase (eluent) is methanol.
3. separating step
Flowing phase (methanol) of naringenin racemic modification is dissolved, and concentration is 5g/L～80g/L.Chromatographic system is by 4～24 preparations
Post forms, and is divided into 4 districts, and the most separation of chromatographic column number are the best, but the complexity of system also improves, optimal pillar number
Mesh is 8～16.Sample solution and eluent inject chromatographic system from injection port and eluent entrance successively, mobile by simulation
The controller of bed chromatographic system, periodically controls the opening and closing of pneumatic operated valve, makes eluting mouth, injection port, extract and raffinate outlet edge
The direction of flowing phase periodically converts, and makes two single enantiomers of naringenin from extract and raffinate outlet outflow system.Obtain
Naringenin single enantiomer solution, concentrated, be dried to obtain highly purified naringenin single enantiomer.
4. finished product detection (high performance liquid chromatography)
Flowing phase: methanol
Flow velocity: 1.0mL/min
Pump: Knauer K501 pump
Chromatographic column: 4.6 × 250mm, 5um, Chiralpak AD-H post
Detector: Knauer K2500 UV-detector
Detection wavelength: 290nm
The present invention is further illustrated below in conjunction with separating embodiment
Separate embodiment 1
A, operating condition
Flowing phase: pure methanol
Sample introduction concentration: racemic modification naringenin concentration 20g/L
Sample introduction flow velocity: UF=3.6mL/min
Eluent flow rate: UD=12.1mL/min
Raffinate flow velocity: UR=6.5mL/min
Extract flow velocity: UE=7.3mL/min
Switching time: TS=1.6min
B, check analysis
With Chiralpak AD-H post, UV-detector, detect wavelength 290nm, flow velocity 1.0mL/min, analytical extraction liquid and
Raffinate forms.S-in extract (-)-naringenin purity is 98.9%, R-in raffinate (+)-naringenin purity is 99.3%.Often
Kilogram fixing phase can produce S-(-)-naringenin and R-(+)-naringenin each 1.3kg and 1.6kg every day, and the response rate is 96.2% He
97.3%.
Separate embodiment 2
A, operating condition
Flowing phase: pure methanol
Sample introduction concentration: racemic modification naringenin concentration 40g/L
Sample introduction flow velocity: UF=3.1mL/min
Eluent flow rate: UD=15.2mL/min
Raffinate flow velocity: UR=7.5mL/min
Extract flow velocity: UE=9.2mL/min
Switching time: TS=1.2min
B check analysis
With Chiralpak AD-H post, UV-detector, detect wavelength 290nm, flow velocity 1.0mL/min, analytical extraction liquid and
Raffinate forms.S-in extract (-)-naringenin purity is 99.1%, R-in raffinate (+)-naringenin purity is 99.3%.Often
Kilogram fixing phase can produce S-(-)-naringenin and R-(+)-naringenin each 2.4kg and 2.6kg every day, and the response rate is 96.5% He
97.2%.
Above-described embodiment is used for illustrating the present invention rather than limiting the invention, and spirit and right in the present invention are wanted
In the protection domain asked, any modifications and changes that the present invention is made, both fall within protection scope of the present invention.
Claims (7)
1. the simulated moving bed chromatography separation of a naringenin enantiomer divides method, it is characterised in that described method for splitting includes
Following steps:
(1) preparation naringenin enantiomer sample liquid: naringenin enantiomer methanol is dissolved, obtains sample liquid, gained sample
In liquid, the concentration of naringenin enantiomer is 5～80g/L；
(2) simulated moving bed chromatography separation divides naringenin enantiomer:
It is the spherical silica gel work that 5～75um surfaces are coated with amylose-three (3,5-dimethylphenylamino formic acid fat) with granularity
For chiral stationary phase, methanol is as flowing phase；
Chromatographic system mainly by: be provided with eluting pump eluent entrance, be provided with extraction pump extract outlet, be provided with sampling pump
Sample liquid entrance, be provided with raffinate pump raffinate outlet, be provided with detector eluent outlet and 4～24 root chromatogram columns composition, point
Becoming tetra-districts of I, II, III, IV, there is 1～6 pillar in every district, and wherein I district is positioned between eluent entrance and extract outlet, II
District is positioned between extract outlet and sample liquid entrance, and III district is positioned between sample liquid entrance and raffinate outlet, and IV district is positioned at
Between raffinate outlet and eluent outlet；
The sample liquid that step (1) is prepared and eluant methanol respectively from sample liquid entrance and eluent entrance by sampling pump and
Eluting infusion enters chromatographic system, and the outlet of sample liquid entrance, eluent entrance, extract, raffinate outlet are simultaneously along eluting liquid stream
Dynamic direction periodically switches to next root chromatogram column, containing S-(-) extract of-naringenin and containing R-(+) raffinate of-naringenin divides
Not from extract outlet and raffinate outlet outflow system, collect extract and raffinate, the most concentrated, dry, respectively
S-(-)-naringenin and R-(+)-naringenin to single configuration；
The Parameter Conditions of fractured operation is: sample liquid flow velocity 1～10mL/min, eluent flow rate 1～100mL/min, extract flow
Speed 1～50mL/min, raffinate flow velocity 1～50mL/min, it is spaced 1～10min switching time.
2. method for splitting as claimed in claim 1, it is characterised in that the operation temperature of described simulated moving bed chromatography system
It it is 10～40 DEG C.
3. method for splitting as claimed in claim 1, it is characterised in that the Parameter Conditions of described fractured operation is: sample liquid flow
Speed 2～8mL/min, eluent flow rate 5～80mL/min, extract flow velocity 3～40mL/min, raffinate flow velocity 3～40mL/min,
It is spaced 2～8min switching time.
4. method for splitting as claimed in claim 1, it is characterised in that the Parameter Conditions of described fractured operation is: sample liquid flow
Speed 2～6mL/min, eluent flow rate 5～50mL/min, extract flow velocity 5～30mL/min, raffinate flow velocity 5～30mL/min,
It is spaced 2～5min switching time.
5. method for splitting as claimed in claim 1, it is characterised in that in step (1), naringenin pair in described sample liquid
The concentration reflecting body is 20～40g/L.
6. method for splitting as claimed in claim 1, it is characterised in that in step (2), described surface is coated with straight chain and forms sediment
The granularity of the spherical silica gel of powder-three (3,5-dimethylphenylamino formic acid fat) is 20～40um.
7. method for splitting as claimed in claim 1, it is characterised in that in step (2), chromatographic column in described chromatographic system
Being 8～16, there are 2～4 pillars in every district.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109187776A (en) * | 2018-08-01 | 2019-01-11 | 广州市香雪制药股份有限公司 | The separation method of aurantiin enantiomter |
| CN114230541A (en) * | 2021-12-17 | 2022-03-25 | 浙江省柑橘研究所 | Manual naringenin splitting method and absolute configuration determining method |
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| CN103788049A (en) * | 2012-11-02 | 2014-05-14 | 江苏汉邦科技有限公司 | Method for splitting pinocembrin enantiomers through simulated moving bed chromatography |
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2016
- 2016-05-13 CN CN201610317990.0A patent/CN105801549A/en active Pending
Patent Citations (3)
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| CN1683368A (en) * | 2005-03-17 | 2005-10-19 | 浙江大学宁波理工学院 | Simulated moving bed chromatography separating method of omeprazole antimer |
| CN103788049A (en) * | 2012-11-02 | 2014-05-14 | 江苏汉邦科技有限公司 | Method for splitting pinocembrin enantiomers through simulated moving bed chromatography |
| CN104557682A (en) * | 2014-08-12 | 2015-04-29 | 江苏汉邦科技有限公司 | Method for splitting chlortrimeton enantiomer by using simulated moving bed chromatography |
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| 柳春辉，韩晓茜，李文智，左晓红，李永民，陈立仁: "模拟移动床技术研究进展", 《西北地区第三届色谱学术报告会暨甘肃省第八届色谱年会》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109187776A (en) * | 2018-08-01 | 2019-01-11 | 广州市香雪制药股份有限公司 | The separation method of aurantiin enantiomter |
| CN109187776B (en) * | 2018-08-01 | 2022-03-22 | 广州市香雪制药股份有限公司 | Method for separating naringin enantiomer |
| CN114230541A (en) * | 2021-12-17 | 2022-03-25 | 浙江省柑橘研究所 | Manual naringenin splitting method and absolute configuration determining method |
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