CN108164464A - A kind of analysis method that can be kept completely separate (-)-huperzine and (+)-huperzine - Google Patents
A kind of analysis method that can be kept completely separate (-)-huperzine and (+)-huperzine Download PDFInfo
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- CN108164464A CN108164464A CN201810115692.2A CN201810115692A CN108164464A CN 108164464 A CN108164464 A CN 108164464A CN 201810115692 A CN201810115692 A CN 201810115692A CN 108164464 A CN108164464 A CN 108164464A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/89—Inverse chromatography
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/07—Optical isomers
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
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Abstract
The present invention relates to a kind of analysis method that can be kept completely separate () huperzine and (+) huperzine, including the following contents:By the injection of the mixed solution of () huperzine of preparation and (+) huperzine using poly sugar derivatives in the high performance liquid chromatograph of stationary phase, to be rinsed and being detached with the flow visualizing that acetonitrile or alcohols form with ammonium acetate solution.The detection method of the present invention, by detecting the content of (+) huperzine in product, not only can intuitively reflect the quality of product and provide help for resolution process;And although this method uses reverse-phase chromatography condition, Liquid apparatus need not carry out the switching of positive reverse phase, time saving and energy saving to save trouble using chiral chromatographic column;Chromatographic column, can also be adjusted to prepare column, () huperzine is prepared for fractionation by the analysis method of the present invention.
Description
Technical field
The present invention relates to pharmaceutical technology fields, and in particular to a kind of to be kept completely separate (-)-huperzine and (+)-huperzine
The analysis method of first.
Background technology
Huperzine:Chemical name is (1R, 9S, 13E) -1- amino -13- ethylidene -11- methyl -6- aza-tricycles
[7.3.1.0] ten three -2 (7), 3,10- triolefin -5- ketone, molecular weight 242.
This product is a kind of Reversible cholinesterase inhibitor, has selective inhibitory to true cholinesterase.Biology
It is active high, have higher fat-soluble, molecule is small, easily through blood-brain barrier, into maincenter after be more distributed in brain frontal lobe,
Temporal lobe, hippocampus etc. have the brain area of close ties with learning and memory, have under low dosage to acetylcholinesterase (AChE) powerful
Inhibiting effect, acetylcholine (ACh) content for making nerve synapse gap in distributed area is significantly raised, emerging so as to enhance neuron
It puts forth energy to conduct, intensified learning and the excitation of memory brain area, plays and improve cognitive function, enhancing memory keeps and promotes memory again
Existing effect.Have now been found that the conjugation of (+)-huperzine and acetylcholine is poor, far below (-)-huperzine.It is artificial to close
Into method obtain be (±)-huperzine racemic mixture, to obtain (-)-huperzine of high-purity then needs
Mixture is detached.
Need switching anti-first using positive phase separation the separation of (±)-huperzine isomers in the prior art
Phase system is converted into positive phase system, needs to consume manpower and time, often switching is lossy to equipment;Secondly, positive item
Chromatographic peak peak shape under part is poor, and theoretical cam curve is relatively low.At present there is no document report can be kept completely separate (-)-huperzine and
The reverse phase separation condition of (+)-huperzine.
Invention content
The purpose of the present invention is to provide a kind of analysis sides that can be kept completely separate (-)-huperzine and (+)-huperzine
Method, the theoretical cam curve, separating degree, tailing factor of the method etc. is satisfied by the requirement of Pharmaceutical Analysis detection, and detection is convenient, is suitble to
In the separation and detection of (-)-huperzine and (+)-huperzine, solves the positive reverse phase of frequent switching in the prior art
System causes the loss to Liquid apparatus, consumes a large amount of manpowers and time;And the chromatographic peak peak shape under the conditions of positive is poor, reason
By the number of plates it is relatively low the problem of.
To achieve these goals, the present invention provides following technical solution, a kind of to be kept completely separate (-)-huperzine
With the analysis method of (+)-huperzine, the method includes:By reversed-phased high performace liquid chromatographic from containing (-)-huperzine
First in the mixed solution of (+)-huperzine with isolating (-)-huperzine;(-)-huperzine and (+)-huperzine
It dissolves to obtain with the mixed solution of water and organic solvent;Mobile phase used in the high performance liquid chromatography is by mobile phase A and stream
Dynamic phase B compositions:The mobile phase A is ammonium acetate solution, and the Mobile phase B is acetonitrile or alcohols;The high performance liquid chromatography
Stationary phase used includes poly sugar derivatives.
As a further improvement on the present invention, a concentration of the 0.005 of (-)-huperzine and (+)-huperzine~
2mg/mL, more preferably 0.01mg/mL.
As a further improvement on the present invention, in the mobile phase A concentration range of ammonium acetate solution for 15~
25mmol/L, more preferably 20mmol/L.
As a further improvement on the present invention, in the mobile phase A ammonium acetate solution pH ranging from 5.5~6.5, it is excellent
It is selected as 6.0.
As a further improvement on the present invention, the Mobile phase B is preferably acetonitrile, because the viscosity of acetonitrile is low, system pressure
Power is small;Cutoff wavelength is low to be conducive to baseline stability.
As a further improvement on the present invention, in the mixed solution of the water and organic solvent organic solvent be selected from acetonitrile or
Alcohol organic solvent, the alcohol organic solvent include methanol, ethyl alcohol or isopropanol;Because flowing phase composition is generally containing acetonitrile, it is
Reduce solvent effect, the preferred acetonitrile of organic solvent.
As the further improvement of the present invention, the mixed solution of the water and organic solvent, to reduce solvent effect simultaneously
Consider that preferably 50% acetonitrile solution is prepared as solvent with reference to sample solubility.
As a further improvement on the present invention, when Mobile phase B is acetonitrile, to obtain better peak shape, gradient elution,
In 0~20 minute, the volume ratio of mobile phase A and Mobile phase B is 4~1:1.
As a further improvement on the present invention, the flow velocity used is 0.5~1.0mL/min, preferably 0.7mL/min.
As a further improvement on the present invention, the stationary phase includes poly sugar derivatives, including three (3,5- xylyls
Carbamate) amylose, three (3,5- xylyls carbamate) celluloses, three (the chloro- 4- MethYlphenylaminos first of 3-
Acid esters) cellulose, three (3,5- Dichloro-phenylamino formic acid esters) celluloses or its mixture, preferably surface is coated with three (3-
Chloro- 4- methyl phenyl carbamates) cellulose silica gel.
As a further improvement on the present invention, the column temperature of the chiral column used in the reversed-phased high performace liquid chromatographic is ranging from
30~40 DEG C, the low influence peak shape of temperature, temperature height is big to the loss of chromatographic column, and preferably column temperature is 35 DEG C.
As a further improvement on the present invention, the reversed-phased high performace liquid chromatographic is examined using ultraviolet lamp detector
It surveys, the Detection wavelength is 230~330nm, excludes low band, and the absorption maximum for selecting huperzine is Detection wavelength, preferably
310nm。
Compared with prior art, it is the advantages of analyzing detecting method of the present invention:(-)-huperzine can not only be completely separated
First and (+)-huperzine, and Liquid apparatus need not carry out the switching of positive reverse phase, it is more convenient than positive phase system use, and flow
Phase composition is common, preparation is simple, save trouble and labor, and agents useful for same is lower relative to positive reagent price, escapable cost;Analysis
Time is short, time saving;Separating degree, tailing factor, theoretical cam curve have relatively satisfactory result.The present invention is analysis method, also may be used
Chromatographic column is adjusted to prepare column and prepares (-)-huperzine for fractionation.
Description of the drawings
Fig. 1 is the HPLC collection of illustrative plates obtained according to embodiment 1.
Fig. 2 is the HPLC collection of illustrative plates obtained according to embodiment 2.
Fig. 3 is the HPLC collection of illustrative plates obtained according to embodiment 3.
Specific embodiment
For ease of those skilled in the art understand that the content of present invention, this hair is further described below in conjunction with specific embodiment
Bright technical solution, but the following contents should not in any way limit the claimed range of claims of the present invention.
" retention time ", " separating degree ", " tailing factor ", the paraphrase of " theoretical cam curve " and the following institute of formula in embodiment
Show:
Retention time (tR):Refer to sample and the time needed for maximum chromatography peak response occur from sample introduction to the sample through elution.
Separating degree (Rs):Refer to the separation situation of two components in certain mixture.It can be calculated by the following formula:
Rs=2 (tR2-tR1)(W1+W2)
In formula, tR2And tR1The respectively retention time of two substances, W1And W2Respectively in the corresponding peak width of its base portion, by this
Peak extends relatively straight both sides to baseline and intersects acquisition.
Tailing factor (As):That is symmetrical factor can be calculated by the following formula:
As=W0.05/2f
In formula, W0.05It is the peak width at peak height 5%, f is peak maximum to the distance between peak forward position, this distance should be from baseline
It is measured at the 5% of more than peak height.
Theoretical cam curve (N):It is the balancing method of column effect.It can be calculated by the following formula:
N=16 (tR/W)2
In formula, tRIt is the retention time of the substance;W is peak width of this peak in its base portion, extends relatively straight two by the peak
While intersect acquisition to baseline.
Embodiment 1
Experiment condition:
Equipment:1260 high performance liquid chromatographs of Agilent.
Chromatographic column:Being coated with three (the chloro- 4- methyl phenyl carbamates of 3-) using Silica Surface, cellulose is stationary phase, greatly
Match 5 μm of 4.6mm × 250mm of fine jade CHIRALCEL OZ-RH.
Mobile phase A is 20mmol/L ammonium acetate solutions, and pH 6.0, Mobile phase B is acetonitrile, gradient elution, at 0~20 point
In clock, the volume ratio of mobile phase A and Mobile phase B is 4~1:1;Flow velocity is 0.7mL/min, Detection wavelength 310nm, column temperature 35
DEG C, 5 μ L of sample size.
The preparation of system suitability solution:(-)-huperzine and (+)-huperzine is taken to be prepared with 50% acetonitrile solution
It is respectively the mixed solution of 0.01mg/mL into concentration.It takes in above-mentioned solution injection liquid chromatograph, records chromatogram, investigate separation
Degree, tailing factor, theoretical cam curve.
As shown in Figure 1, parameters see the table below HPLC analysis charts:
Embodiment 2
Experiment condition:
Equipment:1260 high performance liquid chromatographs of Agilent.
Chromatographic column:Being coated with three (the chloro- 4- methyl phenyl carbamates of 3-) using Silica Surface, cellulose is stationary phase, greatly
Match 5 μm of 4.6mm × 250mm of fine jade CHIRALCEL OZ-RH.
Mobile phase A is 15mmol/L ammonium acetate solutions, and pH 5.5, Mobile phase B is acetonitrile, gradient elution, at 0~20 point
In clock, the volume ratio of mobile phase A and Mobile phase B is 4~1:1;Flow velocity is 1.0mL/min, Detection wavelength 310nm, column temperature 40
DEG C, 5 μ L of sample size.
The preparation of system suitability solution:(-)-huperzine and (+)-huperzine is taken to be prepared with 50% acetonitrile solution
It is respectively the mixed solution of 0.01mg/mL into concentration.It takes in above-mentioned solution injection liquid chromatograph, records chromatogram, investigate separation
Degree, tailing factor, theoretical cam curve.
As shown in Figure 2, parameters see the table below HPLC analysis charts:
Embodiment 3
Experiment condition:
Equipment:1260 high performance liquid chromatographs of Agilent.
Chromatographic column:Being coated with three (the chloro- 4- methyl phenyl carbamates of 3-) using Silica Surface, cellulose is stationary phase, greatly
Match 5 μm of 4.6mm × 250mm of fine jade CHIRALCEL OZ-RH.
Mobile phase A is 25mmol/L ammonium acetate solutions, and pH 6.5, Mobile phase B is acetonitrile, gradient elution, at 0~20 point
In clock, the volume ratio of mobile phase A and Mobile phase B is 4~1:1;Flow velocity is 0.5mL/min, Detection wavelength 310nm, column temperature 30
DEG C, 5 μ L of sample size.
The preparation of system suitability solution:(-)-huperzine and (+)-huperzine is taken to be prepared with 50% acetonitrile solution
It is respectively the mixed solution of 0.01mg/mL into concentration.It takes in above-mentioned solution injection liquid chromatograph, records chromatogram, investigate separation
Degree, tailing factor, theoretical cam curve.
Shown in HPLC analysis charts as attached drawing 3, parameters see the table below:
Claims (10)
- A kind of 1. analysis method that can be kept completely separate (-)-huperzine and (+)-huperzine, which is characterized in that the method Including:It is isolated from the mixed solution containing (-)-huperzine and (+)-huperzine by reversed-phased high performace liquid chromatographic (-)-huperzine;The mixed solution of (-)-huperzine and (+)-huperzine water and organic solvent dissolves to obtain; Mobile phase used in the reversed-phased high performace liquid chromatographic is made of mobile phase A and Mobile phase B:The mobile phase A is ammonium acetate solution;The Mobile phase B is acetonitrile or alcohols;Stationary phase used in the reversed-phased high performace liquid chromatographic includes poly sugar derivatives.
- 2. analysis method according to claim 1, it is characterised in that:The organic solvent is selected from acetonitrile or alcohols is organic Solvent, the alcohol organic solvent include methanol, ethyl alcohol or isopropanol.
- 3. analysis method according to claim 1, it is characterised in that:(-)-huperzine and (+)-huperzine Concentration is respectively 0.005 ~ 2 mg/mL, preferably 0.01 mg/mL.
- 4. analysis method according to claim 1, it is characterised in that:The concentration of ammonium acetate solution in the mobile phase A For 15 ~ 25 mmol/L, preferably 20 mmol/L.
- 5. analysis method according to claim 4, it is characterised in that:The pH of ammonium acetate solution is in the mobile phase A 5.5 ~ 6.5, preferably pH are 6.0.
- 6. analysis method according to claim 1, it is characterised in that:When Mobile phase B is acetonitrile, gradient elution, 0 ~ In 20 minutes, the volume ratio of mobile phase A and Mobile phase B is 4 ~ 1:1.
- 7. analysis method according to claim 1, which is characterized in that the flow velocity of mobile phase is 0.5 ~ 1.0 mL/min, excellent Select 0.7 mL/min.
- 8. analysis method according to claim 1, it is characterised in that:The stationary phase poly sugar derivatives include three (3, 5- xylyls carbamate) amylose, three (3,5- xylyls carbamate) celluloses, three (the chloro- 4- methyl of 3- Carbanilate) cellulose, three (3,5- Dichloro-phenylamino formic acid esters) celluloses or its mixture, preferably three (3- Chloro- 4- methyl phenyl carbamates) cellulose.
- 9. according to claim 1 ~ 8 any one of them analysis method, it is characterised in that:The reversed-phased high performace liquid chromatographic institute The column temperature of chiral column is 30 ~ 40 DEG C, and preferably column temperature is 35 DEG C.
- 10. according to claim 1 ~ 8 any one of them analysis method, it is characterised in that:The reversed-phased high performace liquid chromatographic It is detected using ultraviolet lamp detector, the wavelength of ultraviolet light is 230 ~ 330 nm, preferably 310 nm.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102288703A (en) * | 2011-07-29 | 2011-12-21 | 江南大学 | Method for rapidly detecting phenyllactic acid isomer by reversed phase high performance liquid chromatogram |
CN105044269A (en) * | 2015-06-30 | 2015-11-11 | 成都百裕科技制药有限公司 | Method for detecting initial material II in apixaban through reversed-phase high performance liquid chromatography |
CN106996964A (en) * | 2017-04-20 | 2017-08-01 | 山东赛托生物科技股份有限公司 | Method and the application of hydroxypropyl beta cyclodextrin using reversed-phased high performace liquid chromatographic separating chiral enantiomer |
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- 2018-02-06 CN CN201810115692.2A patent/CN108164464B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102288703A (en) * | 2011-07-29 | 2011-12-21 | 江南大学 | Method for rapidly detecting phenyllactic acid isomer by reversed phase high performance liquid chromatogram |
CN105044269A (en) * | 2015-06-30 | 2015-11-11 | 成都百裕科技制药有限公司 | Method for detecting initial material II in apixaban through reversed-phase high performance liquid chromatography |
CN106996964A (en) * | 2017-04-20 | 2017-08-01 | 山东赛托生物科技股份有限公司 | Method and the application of hydroxypropyl beta cyclodextrin using reversed-phased high performace liquid chromatographic separating chiral enantiomer |
Non-Patent Citations (2)
Title |
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许明,宋新波,张丽娟: "石杉碱甲的研究进展", 《DRUG EVALUATION RESEARCH》 * |
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