CN107228915A - A kind of method for efficiently separating purification glycosyl phosphatidylinositol monoethanolamine - Google Patents
A kind of method for efficiently separating purification glycosyl phosphatidylinositol monoethanolamine Download PDFInfo
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- CN107228915A CN107228915A CN201710335353.0A CN201710335353A CN107228915A CN 107228915 A CN107228915 A CN 107228915A CN 201710335353 A CN201710335353 A CN 201710335353A CN 107228915 A CN107228915 A CN 107228915A
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- monoethanolamine
- glycosyl phosphatidylinositol
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- 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
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Abstract
The invention provides a kind of method for efficiently separating purification glycosyl phosphatidylinositol monoethanolamine, the present invention is eluted by solid-phase extraction column and separated, remove most polar component in sample, eluent redissolves after nitrogen is dried up, glycosyl phosphatidylinositol monoethanolamine in sample is enriched with, and is conducive to improving the recovery rate of glycosyl phosphatidylinositol monoethanolamine；The present invention obtains the detection signal of glycosyl phosphatidylinositol monoethanolamine by Liquid Chromatography-Tandem Mass Spectrometry instrument, the post retention time of glycosyl phosphatidylinositol monoethanolamine is determined according to detection signal, the influence of the weak UV absorption property of glycosyl phosphatidylinositol monoethanolamine is avoided, method is operated quick and precisely；Glycosyl phosphatidylinositol ethanolamine products purity obtained by the present invention is high, can be used as food, the examination criteria product of biological and medical science.
Description
Technical field
The present invention relates to the method for efficiently separating purification glycosyl phosphatidylinositol monoethanolamine.
Background technology
Glycosyl phosphatidylinositol monoethanolamine (Amadori phosphatidylethanolamine, Amadori-PE) is food
Or the class that the aldehyde ketone base of the compound such as the phosphatidyl-ethanolamine and reduced sugar in organism occurs the reaction of carbonyl amine and produced is potential
Chemical hazard thing.Reported research shows at present, glycosyl phosphatidylinositol monoethanolamine and diabetes and its complication, Aging
There is correlation in the disease such as dysfunction and cancer.The precursor substance of glycosyl phosphatidylinositol monoethanolamine --- phosphatide is wide
It is general to be present in ordinary meal.Phosphatide based food may all trigger glycosyl phosphatidylinositol monoethanolamine in processing, storage
Safety issue.
The glycosyl phosphatidylinositol monoethanolamine standard sample for preparing high-purity is the key technology for detecting glycosylated lipid
Premise.The preparation of glycosyl phosphatidylinositol monoethanolamine is mainly by glycosyl phosphatidylinositol monoethanolamine and non-glycosylated phosphatidyl-ethanolamine
Separated, the current reported separation method on glycosyl phosphatidylinositol monoethanolamine mainly have liquid chromatography separation and
Thin layer chromatography.Jeong-Ho Oak et al. (Jeong-Ho Oak K N T M.Synthetically prepared
Amadori-glycated phosphatidylethanolamine can trigger lipid peroxidation via
free radical reactions[J].FEBS J.2000,481:26-30.) by the sample containing glycosyl phosphatidylinositol monoethanolamine
Product are re-dissolved in the hydrogen-oxygen of 1mL methanol -30% by Bond Elut phenyl boric acids (PBA) cylinder solid-phase extraction column, gained lipid-soluble extract
Change ammonium (95:5, v:V) in, it is then loaded on the PBA balance columns of same solvent.With the other ammonium hydroxide of 3mL methanol -30%
(95:5, v:V) eluted, discard eluent.Glycosyl phosphatidylinositol monoethanolamine is reclaimed with the elution of 5mL methanol again, and identical
Under the conditions of purified by performance liquid chromatographic column.At present, this method is in the correlative study of glycosyl phosphatidylinositol monoethanolamine
Largely quoted.But this method pre-treatment troublesome poeration, and do not disclose with high performance liquid chromatography detection glycosyl phosphatidylinositol
The testing conditions of monoethanolamine.Utzmann et al. (Utzmann C M, Lederer M O.Identification and
Quantification of Aminophospholipid-Linked Maillard Compounds in Model
Systems and Egg Yolk Products[J].Journal of Agricultural and Food
Chemistry.2000,48(4):1000-1008.) pass through triflate, phosphatidyl-ethanolamine and 1,8- diazabicyclos
Isopropylidene-glycosyl phosphatidylinositol monoethanolamine is prepared, three fluoric acids-water is added and changes into glycosyl phosphatidylinositol ethanolamine products.
Solvent is removed in high vacuum, residue is dissolved in chloroform, passes through column chromatography chloroform-methanol-water (volume ratio 95:35:5)
It is purified by flash, eluent is detected by thin-layer chromatography post, 0.1% (w/v) 2,7- dichlorofluorescein methanol solutions
It is used as spraying reagent.Reagent is evaporated again, residue is dissolved in methanol, by film filter, methanol is stripped off, high vacuum is done
It is dry to obtain glycosyl phosphatidylinositol monoethanolamine.Sookwong et al. (Sookwong P, Nakagawa K, Fujita I, et
al.Amadori-Glycated Phosphatidylethanolamine,a Potential Marker for
Hyperglycemia,in Streptozotocin-Induced Diabetic Rats[J].Lipids.2011,46(10):
943-952.) by the fat-soluble product in Folch method separation and Extraction glycosylation liquid, then extract is evaporated to dryness, will
Residue is dissolved in 10mL chloroform-methanols (2:1, v:V) it is then water-soluble with methanol -5mM ammonium acetates by preparative reversed-phase column in
Liquid (99:1, v:V) separation elution is carried out, glycosyl phosphatidylinositol monoethanolamine is made.
Only it is difficult to detect using liquid chromatography because glycosyl phosphatidylinositol monoethanolamine is almost without characteristic ultraviolet absorption
The signal of glycosyl phosphatidylinositol monoethanolamine, separating-purifying efficiency is low.Need to add fluorescence derivative examination using thin-layer chromatography rule
Agent is characterized, and fluorescence reagent, troublesome poeration are then removed again, thereby increases and it is possible to cause the loss of glycosyl phosphatidylinositol monoethanolamine.
The inventive method extracts the fat-soluble product in sample by SPE, then is obtained by Liquid Chromatography-Tandem Mass Spectrometry detector
The detection signal of glycosyl phosphatidylinositol monoethanolamine, determines post retention time.By collecting the separation that fixed column retention time passes through
Liquid, obtains the glycosyl phosphatidylinositol monoethanolamine sample of high-purity after nitrogen drying.This method operation is quick, and the degree of accuracy is high, is made
The purity of glycosyl phosphatidylinositol monoethanolamine is higher than 95%.
The content of the invention
It is an object of the invention to provide a kind of method for efficiently separating purification glycosyl phosphatidylinositol monoethanolamine, the present invention is also
There is provided using the glycosyl phosphatidylinositol monoethanolamine obtained after this method separating-purifying.This method operation is quick, and the degree of accuracy is high, obtains
Rate is high, and sample purity is high.
To achieve the above object, the technical scheme taken：A kind of efficiently separate purifies glycosyl phosphatidylinositol monoethanolamine
Method, methods described includes：
(1) sample containing glycosyl phosphatidylinositol monoethanolamine is separated by solid-phase extraction column, solid-phase extraction column point
From the mixed liquor that eluent used is chloroform and methanol, the eluent by solid-phase extraction column is collected；
(2) eluent for collecting step (1) is redissolved after drying with methanol solution, then uses the lysate after redissolution
Liquid chromatogram is separated, and liquid chromatogram separation eluent used is water and the mixed liquor of methanol, according to glycosyl phosphatidylinositol
The post retention time of monoethanolamine collects the eluent by liquid-phase chromatographic column.
Preferably, the volume ratio of chloroform and methanol is 2 in the mixed liquor of chloroform and methanol in the step (1):8~4:6.
Preferably, solid-phase extraction column is C in the step (1)18Solid-phase extraction column.
Preferably, the volume of the eluent in rapid (1) used in SPE post separation is the 0.5~10 of sample volume
Times.
Preferably, the volume of the eluent in rapid (1) used in SPE post separation is 2~5 times of sample volume.
Preferably, the volume ratio of the mixed liquor reclaimed water and methanol of step (2) reclaimed water and methanol is 0:100~10:90.
Preferably, methanol solution is the methanol solution that volumetric concentration is 100% in the step (2).
Preferably, the post retention time of glycosyl phosphatidylinositol monoethanolamine is by liquid chromatography tandem in the step (2)
What mass spectrograph was determined.
Preferably, the post retention time of glycosyl phosphatidylinositol monoethanolamine is 5.0~6.0 minutes in the step (2).
Preferably, drying is using nitrogen drying in the step (2).
The invention provides a kind of using the glycosyl phosphatidylinositol monoethanolamine obtained after method separating-purifying described above.
The inventive method is slightly purified using solid-phase extraction column, and purification liquid redissolves after being dried up with nitrogen, is enriched sample
In glycosyl phosphatidylinositol monoethanolamine, then by Liquid Chromatography-Tandem Mass Spectrometry instrument obtain detection signal determine glycosyl phosphatidylinositol second
The post retention time of hydramine, eluent is collected according to the post retention time of glycosyl phosphatidylinositol monoethanolamine, carries out smart purification.
Compared with prior art, the present invention has the advantages that：
(1) present invention is eluted by solid-phase extraction column and separated, and removes most polar component in sample, and eluent passes through
Redissolved after nitrogen drying, the glycosyl phosphatidylinositol monoethanolamine in sample is enriched with, be conducive to improving glycosyl phosphatidylinositol ethanol
The recovery rate of amine；
(2) present invention obtains the detection signal of glycosyl phosphatidylinositol monoethanolamine by Liquid Chromatography-Tandem Mass Spectrometry instrument, according to
Detection signal determines the post retention time of glycosyl phosphatidylinositol monoethanolamine, it is to avoid the weak ultraviolet absorbability of glycosyl phosphatidylinositol monoethanolamine
The influence of matter, method is operated quick and precisely；
(3) the glycosyl phosphatidylinositol ethanolamine products purity obtained by the present invention is high, can be used as food, the inspection of biological and medical science
Survey standard items.
Brief description of the drawings
Fig. 1 be different volumes than chloroform and methanol extract liquid to the glycosylation palmityl-SN- glyceryl -3- of 1,2- bis-
In the influence of phosphatidyl-ethanolamine extracted amount, figure：1-1:50% methanol；1-2:60% methanol；1-3:80% methanol；1-4：
100% methanol；
Glycosylation palmityl-SN- glyceryl -3- the phosphatidyl-ethanolamines of 1,2- bis- when Fig. 2 is different mobile phase ratios
In HPLC-MS/MS chromatograms, figure：2-1:85% methanol；2-2:90% methanol；2-3:98% methanol；2-4:100% methanol；
Fig. 3 is the liquid phase of palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- after purification in the embodiment of the present invention 3
Chromatogram；
Fig. 4 is one of the glycosylation palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- in the embodiment of the present invention 3
Level mass spectrogram；
Fig. 5 is two of the glycosylation palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- in the embodiment of the present invention 3
Level mass spectrogram；
Fig. 6 is the liquid phase of palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- before purification in the embodiment of the present invention 3
Chromatogram.
Embodiment
To better illustrate the object, technical solutions and advantages of the present invention, below in conjunction with specific embodiment to the present invention
It is described further.
Embodiment 1：Different volumes than chloroform and influence of the methanol extract liquid to glycosyl phosphatidylinositol monoethanolamine extracted amount
Exemplified by glycosylating the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis-, to compare chloroform and methanol volume
Than 0:1~1:The extracted amount of the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- is glycosylated in the range of 0.As a result such as Fig. 1
It is shown, compare glycosylation 1, the chromatogram and selection ion detection mould of the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 2- bis-
Peak area under formula is understood, works as chloroform：When methanol volume ratio is more than 1, extract dry containing more nonpolarity elements in sample liquid
Disturb, it is more difficult to the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- of isolated glycosylation bis- (1-1,1-2 institutes in such as Fig. 1
Show).Work as chloroform：When methanol volume ratio is less than 0.25, find to glycosylate the palmityl-SN- of 1,2- bis- under Salbutamol Selected Ion Monitoring pattern
The integrated peak areas very little of glyceryl -3- phosphatidyl-ethanolamines, illustrates to work as chloroform：When methanol volume ratio is less than 0.25, to sample
The recovery rate that the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- are glycosylated in liquid is relatively low (such as 1-3,1-4 institutes in Fig. 1
Show).Therefore, consider, the volume ratio of chloroform and methanol extract liquid is 2:8~4:6.
Embodiment 2：Mobile phase influences notable to the peak shape and retention time of glycosyl phosphatidylinositol monoethanolamine
Polarity after saccharification reaction, which occurs, for the phosphoric acid head group of phosphatidyl-ethanolamine strengthens, and this experiment is with the palms of 1,2- bis-
Exemplified by acyl-SN- glyceryl -3- phosphatidyl-ethanolamines, using reversed phase chromatography separation method to the palmityls of 1,2- bis- in sample -
SN- glyceryl -3- phosphatidyl-ethanolamines and the glycosylation palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- are separated
And purifying.The HPLC- of the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- is glycosylated during different mobile phase ratios
MS/MS chromatograms are as shown in Figure 2.Experiment shows that in this experiment HPLC-MS/MS detection methods, less than 90% methanol is used as stream
During dynamic phase, the glycosylation palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- are on chromatogram almost without obvious
Chromatographic peak.More than 90% methanol can separate the non-glycosylated palmityl-SN- glyceryl -3- phosphatide of 1,2- bis- as mobile phase
Acyl monoethanolamine and the glycosylation palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis-.When 100% methanol is used as mobile phase
When, response peak area of the glycosylation palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis- on chromatogram is maximum, but
It is to have conditions of streaking on chromatogram.When 98% methanol is as mobile phase, the palmityl-SN- glyceryl -3- phosphorus of 1,2- bis- is glycosylated
Peak shape of the acyl monoethanolamine on chromatogram is preferable, but corresponding peak area is less than normal.Consider, glycosyl phosphatidylinositol monoethanolamine
Mobile phase ratio is that the volume ratio of water and methanol is 0:100~10:90.
Embodiment 3：Glycosylate the separating-purifying of the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis-
The glycosyl phosphatidylinositol monoethanolamine reaction solution for taking 5mL reactions to complete pours into the C activated18Solid-phase extraction column, delays
Slow 10mL (the 2 times of reaction solution volumes) volume ratio that adds is 2:8 chloroform-methanol eluent carries out elution separation；Collect by solid
The eluent of phase extraction column, is redissolved after nitrogen drying with the methanol solution of 3mL100% concentration；
(2) supernatant liquid for redissolving liquid is taken to be detected that chromatographic column is Venusil into Liquid Chromatography-Tandem Mass Spectrometry instrument
ASB C18(5 μm, 4.6 × 150mm), eluent is volume ratio 0.1:99.9 water-methanol solution, flow velocity 0.5mL/min, chromatogram
25 DEG C of column temperature, obtain detection signal, determine post retention time be 5.0-6.0min, liquid chromatogram as shown in Figures 3 and 4, matter
Spectrogram is as figure 5 illustrates.Do not connect under mass detector, the same terms, collect solution of the 5.5-6.0min by liquid-phase chromatographic column, nitrogen
Drying obtains the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamine samples of glycosylation 1,2- bis- of purity 97.0%.
The glycosyl phosphatidylinositol monoethanolamine reaction solution for reacting completion is directly detected by liquid chromatogram, detector bar
Part is identical with the chromatographic condition of the present embodiment step (2), as a result as shown in Figure 6.
Fig. 3 and Fig. 6 is contrasted and found, glycosyl phosphatidylinositol second in sample after (1) is purified the step of the inventive method
The purity of hydramine is increased substantially.
Embodiment 4：Glycosylate the separating-purifying of the myristoyl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis-
Myristoyl-SN- glyceryl -3- phosphatidyl-ethanolamine the reaction solutions of glycosylation 1,2- bis- for taking 5mL reactions to complete
Pour into the C activated18Solid-phase extraction column, it is 3 to be slowly added to 15mL (3 times of reaction solution volumes) volume ratio:7 chloroform-methanol is washed
De- liquid carries out elution separation；The eluent by solid-phase extraction column is collected, it is molten with the methanol of 3mL100% concentration after nitrogen drying
Liquid redissolves；
(2) supernatant liquid for redissolving liquid is taken to be detected that chromatographic column is Venusil into Liquid Chromatography-Tandem Mass Spectrometry instrument
ASB C18(5 μm, 4.6 × 150mm), eluent is volume ratio 10:90 water-methanol solution, flow velocity 0.5mL/min, chromatographic column
30 DEG C of temperature, obtains detection signal, and it is 5.0-6.0min to determine post retention time.Do not connect under mass detector, the same terms, receive
Collect solution of the 5.3-5.8min by liquid-phase chromatographic column, nitrogen dries up the glycosylation 1 for obtaining purity 98.5%, the nutmegs of 2- bis-
Acyl-SN- glyceryl -3- phosphatidyl-ethanolamine samples.
Embodiment 5：Glycosylate the separating-purifying of the palmityl-SN- glyceryl -3- phosphatidyl-ethanolamines of 1,2- bis-
Palmityl-SN- glyceryl -3- phosphatidyl-ethanolamine the reaction solutions of glycosylation 1,2- bis- for taking 3mL reactions to complete
The C18 solid-phase extraction columns activated are poured into, it is 4 to be slowly added to 15mL (5 times of reaction solution volumes) volume ratio:6 chloroform-methanol is washed
De- liquid carries out elution separation；The eluent by solid-phase extraction column is collected, it is molten with the methanol of 3mL100% concentration after nitrogen drying
Liquid redissolves；
(2) supernatant liquid for redissolving liquid is taken to be detected that chromatographic column is Venusil into Liquid Chromatography-Tandem Mass Spectrometry instrument
ASB C18(5 μm, 4.6 × 150mm), eluent is volume ratio 5:95 water-methanol solution, flow velocity 0.5mL/min, chromatographic column temperature
35 DEG C of degree, obtains detection signal, and it is 5.0-6.0min to determine post retention time.Do not connect under mass detector, the same terms, collect
5.3-5.6min is by the solution of liquid-phase chromatographic column, and nitrogen dries up the glycosylation 1 for obtaining purity 97.5%, and the palmityls of 2- bis--
SN- glyceryl -3- phosphatidyl-ethanolamine samples.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than the present invention is protected
The limitation of scope is protected, although being explained in detail with reference to preferred embodiment to the present invention, one of ordinary skill in the art should
Understand, technical scheme can be modified or equivalent substitution, without departing from the essence of technical solution of the present invention
And scope.
Claims (10)
1. a kind of method for efficiently separating purification glycosyl phosphatidylinositol monoethanolamine, it is characterised in that methods described includes：
(1) sample containing glycosyl phosphatidylinositol monoethanolamine is separated by solid-phase extraction column, SPE post separation institute
Eluent is the mixed liquor of chloroform and methanol, collects the eluent by solid-phase extraction column；
(2) eluent for collecting step (1) is redissolved after drying with methanol solution, and the lysate after redissolution then is used into liquid phase
Chromatogram is separated, and liquid chromatogram separation eluent used is water and the mixed liquor of methanol, according to glycosyl phosphatidylinositol ethanol
The post retention time of amine collects the eluent by liquid-phase chromatographic column.
2. according to the method described in claim 1, it is characterised in that chlorine in the mixed liquor of chloroform and methanol in the step (1)
The imitative volume ratio with methanol is 2:8~4:6.
3. according to the method described in claim 1, it is characterised in that solid-phase extraction column is C in the step (1)18SPE
Post.
4. according to the method described in claim 1, it is characterised in that the elution in rapid (1) used in SPE post separation
The volume of liquid is 0.5~10 times of sample volume.
5. according to the method described in claim 1, it is characterised in that step (2) reclaimed water and the mixed liquor reclaimed water of methanol with
The volume ratio of methanol is 0:100~10:90.
6. according to the method described in claim 1, it is characterised in that methanol solution is that volumetric concentration is in the step (2)
100% methanol solution.
7. according to the method described in claim 1, it is characterised in that the post of glycosyl phosphatidylinositol monoethanolamine in the step (2)
Retention time is determined by Liquid Chromatography-Tandem Mass Spectrometry instrument.
8. according to the method described in claim 1, it is characterised in that the post of glycosyl phosphatidylinositol monoethanolamine in the step (2)
Retention time is 5.0~6.0 minutes.
9. according to the method described in claim 1, it is characterised in that drying is using nitrogen drying in the step (2).
10. the glycosyl phosphatidylinositol monoethanolamine obtained after a kind of method separating-purifying using as described in claim 1-9 is any.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111474249A (en) * | 2020-03-11 | 2020-07-31 | 台州学院 | Method for detecting organic alcohol amine compounds in environmental water sample |
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| CN104931618A (en) * | 2015-06-26 | 2015-09-23 | 卢航 | Multiple detection method for six phospholipid in complex sample |
| CN105021758A (en) * | 2015-07-27 | 2015-11-04 | 中国科学院生物物理研究所 | Chemical derivatization-based phosphatide classification detection and quantification method |
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| LEDERER, MO; BAUMANN, M: "Formation of a phospholipid-linked pyrrolecarbaldehyde from model reactions of D-glucose and 3-deoxyglucosone with phosphatidyl ethanolamine", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
| LEDERER, MO; DREISBUSCH, CM; BUNDSCHUH, RM: "Amadori products from model reactions of D-glucose with phosphatidyl ethanolamine - Independent synthesis and identification of 1-deoxy-1-(2-hydroxyethylamino)-D-fructose derivatives", 《CARBOHYDRATE RESEARCH》 * |
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| CN111474249A (en) * | 2020-03-11 | 2020-07-31 | 台州学院 | Method for detecting organic alcohol amine compounds in environmental water sample |
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Application publication date: 20171003 |