CN110133119A - A kind of L- α-detection method of the glyceryl phosphoryl choline in relation to substance - Google Patents

A kind of L- α-detection method of the glyceryl phosphoryl choline in relation to substance Download PDF

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CN110133119A
CN110133119A CN201910290607.0A CN201910290607A CN110133119A CN 110133119 A CN110133119 A CN 110133119A CN 201910290607 A CN201910290607 A CN 201910290607A CN 110133119 A CN110133119 A CN 110133119A
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choline
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phosphoglyceride
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CN110133119B (en
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陈东英
赵宏伟
孙玲
陈欢欢
秦昊
朱晓倩
李立立
翟美玲
包仁芳
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Shanggao Xiehe Biotechnology Co ltd
Shanghai Institute of Materia Medica of CAS
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Shanggao Xiehe Biotechnology Co ltd
Shanghai Institute of Materia Medica of CAS
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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
    • 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
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N30/06—Preparation
    • 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
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N2030/042—Standards
    • G01N2030/047—Standards external

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Abstract

The present invention relates to a kind of liquid chromatography to detect Related substances separation method in chemically synthesized L- α-glyceryl phosphoryl choline.Wherein used chromatographic column is polarity silicagel column or other equivalent chromatographic columns；Mobile phase is methanol-buffer salt solution, acetonitrile-buffer salt solution or methanol-acetonitrile-buffer salt solution, and contains additive.This method is easy to operate, and specificity, preci-sion and accuracy are preferable, the good tolerance of method, inspection and quality control suitable for chemically synthesized L- α-glyceryl phosphoryl choline in relation to substance.

Description

A kind of L- α-detection method of the glyceryl phosphoryl choline in relation to substance
Technical field
The invention belongs to analysis detection fields, and in particular to a kind of liquid chromatography detection L- α-glyceryl phosphoryl choline (with Lower abbreviation glyceryl phosphoryl choline, GPC) in the method in relation to substance phosphoglyceride, choline and Phosphorylcholine etc..
Background technique
Glyceryl phosphoryl choline (Glycerophosphorylcholine, GPC, structure such as following formula) is phosphatidyl choline The completely hydrolyzed product of two fatty acyl groups on (Phosphatidylcholine, PC) molecule, is that human organism is endogenic Soluble small molecular material, before being also important the biosynthesis of neurotransmitter acetylcholine (Acetylcholine) Body.
The GPC of industrialization at present often has hydrolysis of phosphatidlycholine method, full chemistry synthetic method etc. with preparation method.Using completeization The GPC for learning synthetic method production can generate some relevant impurity such as phosphoglyceride (catabolite), choline (initial feed, drop Solve product) and Phosphorylcholine (initial feed existence form in the product, catabolite) and possibly unknown impurity.To protect The purity and quality and safety for demonstrate,proving GPC product, need to be to the related substance in GPC, including phosphoglyceride, choline, Phosphorylcholine And other impurities are detected.
Summary of the invention
The technical issues of solution
GPC and its be the biggish water soluble compound of polarity in relation to substance phosphoglyceride, choline and Phosphorylcholine, and Without UV absorption, fluorescence can not be excited, so the exploitation to detection method has larger difficulty.It there is no at present about completeization Learn the detection method report in synthesis GPC in relation to substance.
To solve the above-mentioned problems, the object of the present invention is to provide a kind of efficient liquid-phase chromatography methods, have preferable protect Characteristic is stayed, and the separating degree between adjacent peak is met the requirements, and peak shape is well-symbolized, and related substance can be preferably used in GPC Phosphoglyceride (code name: a), choline (code name: b) and Phosphorylcholine (code name: c) quantitative determination, it may thereby be ensured that GPC is produced The quality of product.
Technical solution
In order to achieve the above object, the technical solution adopted by the present invention are as follows:
Side in relation to substance phosphoglyceride, choline and Phosphorylcholine in a kind of liquid chromatography detection glyceryl phosphoryl choline Method, wherein used chromatographic column is polarity silicagel column or other equivalent chromatographic columns；Mobile phase is methanol-buffer salt solution, second Nitrile-buffer salt solution or methanol-acetonitrile-buffer salt solution, and contain additive.
The detector that this forwarding method uses is differential refraction detector, evaporative light scattering detector or mass detector.
The liquid chromatography includes conventional liquid phase chromatography or ultra-performance liquid chromatography.
Preferably, the chromatographic column is using silica gel or bonded silica gel as the polar column of filler.
Preferably, the chromatographic column column temperature is 25-50 DEG C, more preferably 40 DEG C.
Preferably, the buffer salt is positive ion-pairing agent (such as tetra-n-butyl ammonium bromide), anion to reagent (such as heptan Alkyl sulfonic acid sodium, perfluorooctane sulfonate, sodium hexanesulfonate etc.), formates (such as ammonium formate), acetate (such as ammonium acetate), phosphate One or more of (such as sodium dihydrogen phosphate).
Preferably, the mobile phase is methyl alcohol-formic acid aqueous ammonium system, and wherein methanol accounts for the volume ratio of mobile phase and is 50-80%, more preferably 65%；The concentration of ammonium formate is 10-100mM, more preferably 20mM in formic acid aqueous ammonium.
Preferably, the additive be one of formic acid, formates, acetic acid, acetate, phosphoric acid, phosphate or a variety of, More preferably phosphoric acid or phosphate, the mass fraction that additive accounts for water phase in mobile phase (i.e. buffer salt solution) is 0.05%- 2%.It is highly preferred that the phosphate is selected from one of sodium dihydrogen phosphate, potassium dihydrogen phosphate or a variety of.
Preferably, the flow rate of mobile phase is 0.1-2.0mL/min.
Specifically, in relation to substance phosphoglyceride, choline and phosphinylidyne in the liquid chromatography detection glyceryl phosphoryl choline The method of choline, includes the following steps:
Step 1: the preparation of blank solution: taking methanol aqueous solution as blank solution；
Step 2: flow visualizing preparation: the aqueous solution of preparation ammonium formate containing 20mM is added as water phase and accounts for water phase matter The phosphate of score 0.1% is measured, measures methanol as organic phase, organic phase and water phase volume are 65:35, by organic phase and water It mixes uniformly；
Step 3: the preparation in relation to substance reference substance solution: taking related substance phosphoglyceride, choline and phosphinylidyne gallbladder respectively Alkali, it is accurately weighed, add methanol aqueous solution to dissolve, related substance reference substance of every 1mL containing about 0.4mg ± 0.02mg is respectively prepared Solution；
Step 4: test solution is prepared: precision weighs glyceryl phosphoryl choline sample about 0.4g ± 0.05g to be determined, adds Methanol aqueous solution dissolution, is made each related object of every 1mL containing about glyceryl phosphoryl choline sample 80mg and unknown content to be determined The test solution of matter；
Related substance reference substance solution and step 4 prepared by the accurate blank solution for measuring step 1 preparation, step 3 respectively Each 10 μ L of the test solution of preparation, is detected using liquid chromatography, is recorded chromatogram, is calculated according to external standard method to be determined Content in relation to substance phosphoglyceride, choline and Phosphorylcholine in glyceryl phosphoryl choline sample.
Calculation formula are as follows:
Wherein, CRFor the concentration in relation to determinand in substance contrast solution, mg/mL；
CsFor glyceryl phosphoryl choline sample concentration, mg/mL in test solution；
AR, AXPeak area respectively in relation to determinand in substance contrast solution and test solution, mV；
Preferably, the volume ratio of first alcohol and water is 65:35 in methanol aqueous solution described in step 1, step 3 and step 4.
Beneficial effect
Method has been carried out to method of the invention through specificity test, linear test, precision test and accuracy test Learn verifying, it was demonstrated that a kind of GPC provided by the invention has an advantage that in relation to the detection method of substance
(1) good separation can be reached between principal component GPC and related substance, each related substance.
(2) this method has good specificity and durability.
(3) this method precision is good.
(4) good linear relationship is presented within the scope of a certain concentration in GPC and related substance.
(5) this method accuracy is good.
(6) GPC and related substance a, the preferable peak shape of b, c are realized simultaneously.
Detailed description of the invention
Fig. 1 is to use the test map of the method for the present invention (curve 1 is blank solution chromatogram；Curve 2 is GPC and its has Close substance typical separate chromatogram: the peak a: phosphoglyceride；The peak b: choline；The peak c: Phosphorylcholine；The peak d: GPC；* peak: unknown Impurity).
Specific embodiment
The embodiment of the present invention is described below in detail, it should be noted that the embodiments described below is exemplary, only It is used to explain the present invention, and is not considered as limiting the invention.In addition, being adopted in embodiment if do not clearly stated Reagent is available in the market.
Embodiment: it present embodiments provides and detection of the GPC in relation to substance is carried out using the method for the present invention.
Instrument and chromatographic condition: Shimazu LC-20 high performance liquid chromatograph；Chromatographic column is polarity silicagel column；Column temperature is 40℃；With methanol: being mobile phase containing 0.1% phosphatic 20mM ammonium formate solution (65:35, v:v)；With high efficiency chromatography liquid phase System is detected, 10 μ L of sampling volume；Flow velocity 1.0mL/min；Using differential refraction detector；Detector temperature is 40 DEG C.
Experimental procedure
Step 1: the preparation of blank solution: take methanol: water (65:35, v:v) mixed solution is as blank solution.
Step 2: flow visualizing preparation: measure deionized water it is appropriate, be added accurately weighed ammonium formate in right amount be made contain The aqueous solution of 20mM ammonium formate is as water phase, and (sodium dihydrogen phosphate accounts for the quality point of water phase to the sodium dihydrogen phosphate of addition 0.1% 0.1%) number is, measures proper amount of methanol as organic phase, example is 65:35 (v:v), after mixing, mistake to organic phase compared with water It filters and ultrasonic.
Step 3: the single preparation in relation to substance reference substance stock solution: taking related substance phosphoglyceride (a), choline respectively (b) accurately weighed with Phosphorylcholine (c), add methanol: list of every 1mL containing about 2mg is respectively prepared in water (65:35, v:v) dissolution A related substance reference substance stock solution.
Step 4: the preparation in relation to substance reference substance solution: taking single related substance reference substance stock solution made from step 3 Each 1mL is placed in same 5mL volumetric flask, adds methanol: every 1mL is made containing about each related substance in water (65:35, v:v) dissolution The reference substance solution of 0.4 mg.
Step 5: mixed solution is prepared: being taken single related each 1mL of substance reference substance stock solution made from step 3, is placed in same In one 5mL volumetric flask, precision weighs about 0.4g GPC sample (without a, b, c impurity), and add methanol: water (65:35, v:v) is molten Solution, every 1mL is made, and containing about principal component 80mg and each mixed solution in relation to substance 0.4mg, (each related substance accounts for about principal component 0.5%).
Each 10 μ L of mixed solution prepared by the accurate blank solution for measuring step 1 preparation, step 5 respectively, sample introduction measurement, note Chromatogram is recorded, sees Fig. 1.
Chromatography peak sequence is followed successively by phosphoglyceride, choline, GPC and Phosphorylcholine.Based on carrying out by the retention time of GPC It calculates, the relative retention time of phosphoglyceride is 0.4；The relative retention time of choline is 0.9；The opposite reservation of Phosphorylcholine Time is 1.3.In addition, at least one unknown impuritie occurs before choline peak, relative retention time 0.6.
Test result shows that blank solvent peak is noiseless to GPC and its detection of related substance, GPC and each related substance it Between, separating degree is all larger than 1.5 between each related substance, and each related substance peak shape is good.
Precision measures 10 μ L of related substance reference substance solution prepared by step 4, respectively at 6 needle of the first balance traveling sample, the It two days and third balance traveling sample 3 times, measures in accordance with the law.Each related substance peak area relative standard deviation (RSD) such as following table. Each RSD in relation to substance peak area is respectively less than 2% as the result is shown, shows that this law precision is good.
Related substance a b c
Peak area RSD% 1.67 0.99 1.76
By reference substance solution measurement result ratio prepared by mixed solution measurement result prepared by step 5 and step 4 Compared with each rate of recovery in relation to substance of investigation.As a result each related substance recovery shows that this law is accurate between 95~108% Degree is good.
Rate of recovery calculation formula:
Wherein Ax, ARIt is corresponding to be measured in determinand peak area and related substance reference substance solution respectively in mixed solution
Object peak area, mV；
Cx、CRCorresponding determinand is dense in testing concentration and related substance reference substance solution respectively in mixed solution Degree,
mg/mL。
Reference substance solution prepared by step 4 dilutes step by step and sample introduction measurement, is 2~3 as detection using signal-to-noise ratio and limits, meter Calculate each detection limit such as following table in relation to substance.Show the sensitivity with higher of this method, can satisfy testing requirements.
In conclusion related substance phosphoric acid is sweet in a kind of liquid chromatography detection glyceryl phosphoryl choline provided by the present invention The method of grease, choline and Phosphorylcholine etc., have it is easy to operate, specificity is good, and preci-sion and accuracy is strong, high sensitivity The advantages of, inspection and quality control suitable for glyceryl phosphoryl choline in relation to substance.

Claims (10)

1. the side in relation to substance phosphoglyceride, choline and Phosphorylcholine in a kind of liquid chromatography detection glyceryl phosphoryl choline Method, it is characterised in that: used chromatographic column is polarity silicagel column or equivalent chromatographic column；Mobile phase be methanol-buffer salt solution, Acetonitrile-buffer salt solution or methanol-acetonitrile-buffer salt solution, and contain additive.
2. in liquid chromatography as described in claim 1 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the detector used is differential refraction detector, evaporative light scattering detector or mass spectrum Detector.
3. in liquid chromatography as described in claim 1 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the buffer salt is positive ion-pairing agent, anion to reagent, formates, acetic acid One or more of salt, phosphate.
4. in liquid chromatography as claimed in claim 3 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the cation is tetra-n-butyl ammonium bromide to reagent；The anion selects reagent From sodium heptanesulfonate, perfluorooctane sulfonate, sodium hexanesulfonate；The formates is ammonium formate；The acetate is ammonium acetate；It is described Phosphate is sodium dihydrogen phosphate.
5. in liquid chromatography as described in claim 1 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the mobile phase is methyl alcohol-formic acid aqueous ammonium system, and wherein methanol accounts for mobile phase Volume ratio be 50-80%；The concentration of ammonium formate is 10-100mM in formic acid aqueous ammonium.
6. in liquid chromatography as claimed in claim 5 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the mobile phase is methyl alcohol-formic acid aqueous ammonium system, and wherein methanol accounts for mobile phase Volume ratio be 65%；The concentration of ammonium formate is 20mM in formic acid aqueous ammonium.
7. in liquid chromatography as described in claim 1 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the additive is formic acid, in formates, acetic acid, acetate, phosphoric acid, phosphate It is one or more；The mass fraction that additive accounts for buffer salt solution in mobile phase is 0.05%-2%.
8. in liquid chromatography as claimed in claim 7 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the additive is one of phosphoric acid, sodium dihydrogen phosphate, potassium dihydrogen phosphate or more Kind.
9. in liquid chromatography as described in claim 1 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, which comprises the steps of:
Step 1: the preparation of blank solution: taking methanol aqueous solution as blank solution；
Step 2: flow visualizing preparation: the aqueous solution of preparation ammonium formate containing 20mM is added as water phase and accounts for water phase quality point The phosphate of number 0.1% measures methanol as organic phase, and organic phase and water phase volume are 65:35, and organic phase and water phase are mixed Uniformly；
Step 3: the preparation in relation to substance reference substance solution: taking related substance phosphoglyceride, choline and Phosphorylcholine respectively, essence It is close weighed, add methanol aqueous solution to dissolve, related substance reference substance solution of every 1mL containing about 0.4mg ± 0.02mg is respectively prepared；
Step 4: test solution is prepared: precision weighs glyceryl phosphoryl choline sample about 0.4g ± 0.05g to be determined, adds methanol Each related substance of every 1mL containing about glyceryl phosphoryl choline sample 80mg and unknown content to be determined is made in aqueous dissolution Test solution；
The related substance reference substance solution and step 4 preparation that respectively prepared by the accurate blank solution for measuring step 1 preparation, step 3 Each 10 μ L of test solution, detected using liquid chromatography, record chromatogram, glycerol phosphorus to be determined is calculated according to external standard method Content in relation to substance phosphoglyceride, choline and Phosphorylcholine in phatidylcholine sample；
Calculation formula are as follows:
Wherein, CRFor the concentration in relation to determinand in substance contrast solution, mg/mL；
CsFor glyceryl phosphoryl choline sample concentration, mg/mL in test solution；
AR, AXPeak area respectively in relation to determinand in substance contrast solution and test solution, mV.
10. in liquid chromatography as claimed in claim 9 detection glyceryl phosphoryl choline in relation to substance phosphoglyceride, choline and The method of Phosphorylcholine, it is characterised in that: the volume of first alcohol and water in methanol aqueous solution described in step 1, step 3 and step 4 Than for 65:35.
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Cited By (2)

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CN112630365A (en) * 2020-11-27 2021-04-09 江苏东南纳米材料有限公司 Method for determining content of dimyristoyl phosphatidylcholine by high performance liquid chromatography
CN116879428A (en) * 2023-06-29 2023-10-13 沈阳金久奇科技有限公司 High performance liquid analysis method for residual content of phosphorylcholine in L-alpha-phosphorylcholine

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CN112630365A (en) * 2020-11-27 2021-04-09 江苏东南纳米材料有限公司 Method for determining content of dimyristoyl phosphatidylcholine by high performance liquid chromatography
CN116879428A (en) * 2023-06-29 2023-10-13 沈阳金久奇科技有限公司 High performance liquid analysis method for residual content of phosphorylcholine in L-alpha-phosphorylcholine
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