CN106706814A - Method for randomly determining EPA (Eicosapntemacnioc Acid) chain-containing compound - Google Patents
Method for randomly determining EPA (Eicosapntemacnioc Acid) chain-containing compound Download PDFInfo
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- CN106706814A CN106706814A CN201710074905.7A CN201710074905A CN106706814A CN 106706814 A CN106706814 A CN 106706814A CN 201710074905 A CN201710074905 A CN 201710074905A CN 106706814 A CN106706814 A CN 106706814A
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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
- 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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Abstract
The invention discloses a method for randomly determining an EPA (Eicosapntemacnioc Acid) chain-containing compound. The method comprises the following steps: 1) sample pretreatment: pretreating the muscle tissue of crucian carp to obtain a lipid crude extract; 2) sample injecting: diluting and filtering the lipid crude extract with an organic solvent, and injecting into a mass spectrometry by using a needle pump injector; 3) mass spectrometry detection: finding parent ions containing daughter ions according to the characteristic daughter ions by using a negative ion mode, and collecting data by using Analyst software; and 4) data analysis: analyzing a spectrum obtained by the mass spectrometry in step 3) to obtain structure information of each ion peak. All EPA fatty acid chain-containing compounds in samples are nondirectionally obtained at random by the method provided by the invention.
Description
Technical field
The invention belongs to Instrumental Analysis field, it is related to a kind of random method of the measure containing EPA chain compounds, refers specifically to one kind
Contain the determination method of the compound of EPA fatty acid chains without Objective random scanning from complex sample.
Background technology
EPA (Eicosapentaenoic Acid), i.e. eicosapentaenoic acid, are the main components of fish oil.EPA belong to Ω-
3 serial polyunsaturated fatty acids, i.e., from first position of double bond of methyl end number the 3rd carbon potential polyunsaturated fatty acid.
EPA is the important nutrient that human body is indispensable but itself can not synthesize again, therefore is referred to as essential fatty acid.Although
Leukotrienes can be converted into EPA in human body, but this speed of the reaction in human body very slow and inversion quantity seldom, far can not expire
The need for sufficient human body is to EPA, it is therefore necessary to directly supplemented from food.
Medical science and Nutritional studies show that EPA has and suppress platelet aggregation, antithrombotic, vasodilator, adjustment blood fat etc.
The function of cardiovascular and cerebrovascular diseases is treated and prevented, EPA peroxide and free radical can suppress tumor cells expression, shorten chromosome
Telomere, promotes the apoptosis of tumour cell.EPA can reduce harmful immune response, and to treating what is caused by autoimmune disorder
Inflammation is effective.Omega-3 fatty acid, including including EPA, to tuberculosis, ephrosis, diabetes B, big enterelcosis and regional ileitis
Treatment can all play a positive role.Recently find that it also has again and promote brain cell growth, development, improve cerebral function,
Memory and learning ability are improved, is strengthened retinal reflex ability and is prevented and treated the work(that senile dementia etc. improves quality of life
Energy.Thus, extracting separating high-purity EPA has turned into the focus that developed country is mutually studied unexpectedly.
The source of commercial EPA is mainly fat content marine fishes high, and the mass fraction of its EPA can reach 20%~
30%.With the change of sea situation and being continuously increased for marine catching intensity, sea fisheries resource structures there occurs great change, ring
The factors such as border pollution, overfishing cause shortage of resources, promote people actively to find new resources of the exploitation rich in EPA.
The related detecting method of current EPA is main based on combined gas chromatography mass spectrometry, and the method predominantly detects free
EPA and esterification or ethyl esterified EPA.Detection method containing EPA chain compounds is mainly liquid chromatography mass combination method.Report at present
The method in road is directed screening method, i.e. known compound A has EPA chains, and the chemically or physically feature according to A is fixed from sample
To screening compounds A.And random non-directional screening method does not have been reported that.
Set up the random method for determining and containing EPA chain compounds, the change containing EPA fatty acid chains in quick scanning complex sample
Compound simultaneously carries out Structural Identification and assay, is conducive to quickly screening EPA raw material resources, promotes EPA health products industry developments.
The content of the invention
The technical problem to be solved in the present invention is to provide random measure chain containing EPA in a kind of complex matrices easy to operate
The method detection method of compound.
In order to solve the above-mentioned technical problem, a kind of random method of the measure containing EPA chain compounds of present invention offer, including with
Lower step：
1), sample pre-treatments：
Gruel is ground to form after carassias auratus muscLe tissue is cleaned, is shaken after adding organic solvent I in gruel and extracted, after extraction is finished
Add pure water and shake mixing；
The mixture of gained is centrifuged with refrigerated centrifuge, pipettes lower phase solution, and the lower phase solution is dried (to be carried out with nitrogen
Low temperature is dried up), obtain lipid crude extract；
Organic solvent I is methyl alcohol：Chloroform=1：The mixed liquor of 2 volume ratios is methyl alcohol：Dichloromethane=1：2 volume ratios
Mixed liquor, the rotten solid-liquid ratio with organic solvent I is 1g/15~30ml；The amount of added water is 0.5 volume of organic solvent I
Times；
2), sample introduction：
By lipid crude extract methyl alcohol：Dichloromethane=1：The organic solvent of 2 volume ratios is settled to 100mL as sample；
Pipette conduct after 1mL samples cross 0.22 μm of filter membrane and treat sample measuring liquid, mass spectrum is injected into using pin infusion emitter；
3), Mass Spectrometer Method：
Using negative ion mode, all parent ions containing the daughter ion are found according to feature daughter ion, sweep limits is
400-1000Da, residence time is 2 seconds, and gas curtain gas is 10psi, and accelerating potential is -4500ev, and auxiliary gas I is 20psi, auxiliary
Gas II is 30psi, and collection of illustrative plates is cumulative 100~200 times；Use Analyst software collection data；
4), data analysis：
By step 3) Mass Spectrometer Method gained spectrogram be analyzed, obtain the structural information of each quasi-molecular ions.That is, in learning sample
The type and quantity of the compound containing EPA chains.
As the random improvement for determining the method containing EPA chain compounds of the invention：
The step 4) be：
By step 3) by noise filtering (minimum peak width is 0.2Da), baseline deduction 4Da goes Mass Spectrometer Method gained spectrogram
After isotopic peak, spectrogram after being processed；Lipid Mass are used after spectrogram after treatment is exported as into txt file
The identification of Spec.Prediction softwares can obtain the structural information of each quasi-molecular ions.
Remarks explanation：With PE 18:1/20:As a example by 5, structure includes 3 partial informations, and PE refers to cytoskeletal protein,
18:1 to refer to wherein one fatty acid chain be the double bond of 18 carbon 1,20:5 refer to another chain.
As random further improvements in methods of the measure containing EPA chain compounds of the invention：
The step 4) also include：
Each parent ion concentration is through formula：Calculate, wherein
AbundanceiIt is Compound abundance, AiBe spectrogram (step 3) Mass Spectrometer Method gained spectrogram) in the specific ion peak peak area,
A1~AnIt is the peak area of all quasi-molecular ions of gained in spectrogram.
The approximate content containing EPA chain compounds in sample can be learnt using above-mentioned formula.
As random further improvements in methods of the measure containing EPA chain compounds of the invention：
The step 1) in, to pipette the centrifugation gains after lower phase solution (that is, including upper phase solution and solid) replacement
Aquatic products tissue, machine solvent I is substituted with the dichloromethane in machine solvent I or chloroform；Repeat extraction 1~3 time；Carried all
The lower phase solution of gained carries out follow-up drying and redissolution after merging after taking.
Remarks explanation：Lower leaf on solution in centrifuge tube after centrifugation, salmon muscle tissue sample then occupy two in pie
In the middle of phase.
Methyl alcohol, chloroform, water three together when will not be miscible, can be divided into upper and lower two-phase, methyl alcohol polarity more by force can be with
Water is miscible, therefore in centrifuge tube, in lower phase, the miscible volume methyl alcohol of water is upper for dichloromethane or the miscible a small amount of methyl alcohol of chloroform
Phase；After due to pipetting and go down phase, actual major part methyl alcohol is not pipetted still in upper phase, therefore when repeating to extract only
Need to add dichloromethane or chloroform.That is, the volumetric usage=machine solvent I of dichloromethane or chloroform when repeating to extract
In dichloromethane or chloroform volumetric usage.Dichloromethane and chloroform recovery similar efficiency, dichloromethane toxicity are weaker than chlorine
It is imitative.
As random further improvements in methods of the measure containing EPA chain compounds of the invention：
The step 1) in, it is with refrigerated centrifuge centrifugation：It is centrifuged 5~15 minutes in 4 DEG C, 8000~12000rpm.
As random further improvements in methods of the measure containing EPA chain compounds of the invention：
The step 2) in, pin infusion emitter flow velocity is 10~20 μ L/min.
As random further improvements in methods of the measure containing EPA chain compounds of the invention：
The step 3) in, the scan method for being used looks for female scanning (Precursor ion scan), feature for son
Ion is m/z 301, removes cluster voltage for -80~-100ev, and collision voltage is -30~-40ev.
In sum, the present invention is characterized daughter ion and looks for female scan method by son under negative ion mode using m/z 301
Contain EPA chain compounds in scanning complex matrices sample, processed through spectrogram with after data analysis, random non-directional obtains all containing
There is the compound of EPA fatty acid chains.Inventive samples pre-treatment, sample introduction, Mass Spectrometer Method, data analysis step, easy to operate, letter
Single easily training, qualitative, quantitative ability are stronger, practical, and suitable laboratory widely uses.
Brief description of the drawings
Specific embodiment of the invention is described in further detail below in conjunction with the accompanying drawings.
Fig. 1 is that son looks for female scan method scanning crucian tissue sample mass spectrogram under negative ion mode.
Specific embodiment
Specific embodiment of the invention is described in detail below in conjunction with accompanying drawing, those skilled in the art is become apparent from geography
How solution puts into practice the present invention.It will be appreciated that though the present invention is described with reference to its preferred embodiment, but these are implemented
Scheme is to illustrate, rather than limitation the scope of the present invention.
Embodiment 1, a kind of random method of the measure containing EPA chain compounds, follow the steps below successively：
1), sample pre-treatments：
Gruel is ground to form after 100g carassias auratus muscLes tissue is cleaned, 1g meat gruels is taken and is added organic solvent (methyl alcohol：Dichloromethane
=1：2 volume ratios) to shake after 21mL and extract, extraction adds pure water 10.5mL and shakes mixing after finishing；
The mixture of gained is centrifuged with refrigerated centrifuge, is centrifuged 5 minutes in 4 DEG C, 12000rpm.Lower phase solution is pipetted, to
14mL dichloromethane mutually and in solid content is added in residue, repeats to extract 2 times；The lower phase solution of gained after all extractions is closed
And, dry after (carry out low temperature drying with nitrogen), obtain lipid crude extract；
2), sample introduction：
By lipid crude extract methyl alcohol：Dichloromethane=1：The organic solvent of 2 volume ratios is settled to 100mL as sample.
Pipette after 1mL samples cross 0.22 μm of filter membrane and be injected into mass spectrum using pin infusion emitter, pin infusion emitter flow velocity is 20 μ L/min.
3), Mass Spectrometer Method：
Using negative ion mode, the scan method for being used looks for female scanning (Precursor ion scan), feature for son
Daughter ion is m/z 301, removes cluster voltage for -100ev, and collision voltage is -40ev.Find all containing this according to feature daughter ion
The parent ion of daughter ion, sweep limits is 400-1000Da, and residence time is 2 seconds, and gas curtain gas is 10psi, accelerating potential for-
4500ev, auxiliary gas I is 20psi, and auxiliary gas II is 30psi, and collection of illustrative plates is cumulative 100 times.Use Analyst software collection data.
4), data analysis：
By step 3) by noise filtering (minimum peak width is 0.2Da), baseline deduction 4Da goes Mass Spectrometer Method gained spectrogram
After isotopic peak, spectrogram (Fig. 1) after being processed.Lipid Mass are used after spectrogram after treatment is exported as into txt file
The identification of Spec.Prediction softwares can obtain the structural information of each quasi-molecular ions.Each parent ion concentration is through formula：Calculate, wherein AbundanceiIt is Compound abundance, AiIt is spectrogram
(step 3) Mass Spectrometer Method gained spectrogram) in the specific ion peak peak area, A1~AnIt is all quasi-molecular ions of gained in spectrogram
Peak area.
Result is as follows：
Crucian tissue sample lipid species are enriched, and the compound containing EPA chains is more, find to be phosphorus after Structural Identification
Fat；31 kinds of phospholipid molecule kind is identified altogether, wherein 8 phosphatid ylcholines, 14 phosphatidyl-ethanolamines, 1 phosphatidylinositols, 4
Individual phosphatidylserine, 3 phosphorus matter acid, 1 phosphatidyl glycerol.Signal is by force most m/z 764.9, and identified is [PCo-16:0/
20:5-H]-[PE18:0/20:5-H]-Overlap.It is specific as described in Table 1.
The structure and abundance messages of the compound containing EPA chains in table 1, crucian tissue sample
Note：a:b/c:D represents two fatty acid chain structures of compound, wherein one is 20:5, as 20 carbon atoms
Fatty acid chain contains 5 unsaturated double-bonds；Prefix o- represents alkyl chain, and remaining is acyl chain.
Confirmatory experiment：According to liquid chromatography tandem mass spectrometry to the sample crucian described in embodiment 1 to detection, acquired results
For：31 kinds of the phospholipid molecule kind containing EPA fatty acid chains is identified altogether, wherein 8 phosphatid ylcholines, 14 phosphatidyl ethanols
Amine, 1 phosphatidylinositols, 4 phosphatidylserines, 3 phosphorus matter acid, 1 phosphatidyl glycerol, each quasi-molecular ions abundance relative standard
Deviation RSD≤7%.
Comparative example 1-1, by the step 1 of embodiment 1) in repetition extract 2 times and make into repeat to extract 0 time；Remaining is equal to reality
Apply example 1.
Comparative example 2-1, by the step 1 of embodiment 1) in refrigerated centrifuge condition be 8000rpm, temperature, time are constant；Its
It is remaining to be equal to embodiment 1.
Comparative example 3-1, by the step 2 of embodiment 1) in pin infusion emitter flow velocity be 5 μ L/min；Remaining is equal to embodiment
1。
Comparative example 3-2, by the step 2 of embodiment 1) in pin infusion emitter flow velocity be 30 μ L/min；Remaining is equal to implementation
Example 1.
Comparative example 4-1, by the step 3 of embodiment 1) in scan method be changed to daughter ion scanning (Product ion
Scan), feature daughter ion is m/z 764.9；Remaining is equal to embodiment 1.
Comparative example 4-2, by the step 3 of embodiment 1) in scan method be full scan (Q1scan), remaining is equal to implementation
Example 1.
Comparative example 4-3, by the step 3 of embodiment 1) in feature daughter ion m/z 301 be changed to m/z 300；Remaining is equal to
Embodiment 1.
Comparative example 4-4, by the step 3 of embodiment 1) in feature daughter ion m/z 301 be changed to m/z 302；Remaining is equal to
Embodiment 1.
Comparative example 4-5, by the step 3 of embodiment 1) in the cluster voltage -100ev that goes be changed to -60ev；Remaining is equal to embodiment
1。
Comparative example 4-6, by the step 3 of embodiment 1) in the cluster voltage -100ev that goes be changed to -120ev；Remaining is equal to implementation
Example 1.
Comparative example 4-7, by the step 3 of embodiment 1) in collision voltage -40ev be changed to -20ev；Remaining is equal to embodiment
1。
Comparative example 4-8, by the step 3 of embodiment 1) in collision voltage -40ev be changed to -50ev；Remaining is equal to embodiment
1。
It is described in table 2 below using the compound containing EPA and abundance obtained by above-mentioned comparative example methods described.
Table 2
As fully visible, a kind of random method of the measure containing EPA chain compounds of the invention can fast and effectively to crucian
Deng the compound non-directional sweep measuring containing EPA chains in aquatic products tissue sample, solve and oriented present in prior art
Scanning is just for target compound, the low problem of EPA raw material resources screening efficiencies.
Finally, in addition it is also necessary to it is noted that listed above is only several specific embodiments of the invention.Obviously, this hair
It is bright to be not limited to above example, there can also be many deformations.One of ordinary skill in the art can be from present disclosure
The all deformations directly derived or associate, are considered as protection scope of the present invention.
Claims (7)
1. it is random to determine the method containing EPA chain compounds, it is characterized in that comprising the following steps：
1), sample pre-treatments：
Gruel is ground to form after carassias auratus muscLe tissue is cleaned, is shaken after adding organic solvent I in gruel and extracted, extraction is added after finishing
Pure water simultaneously shakes mixing；
The mixture of gained is centrifuged with refrigerated centrifuge, pipettes lower phase solution, and the lower phase solution is dried, and obtains lipid crude extract；
Organic solvent I is methyl alcohol：Chloroform=1：The mixed liquor of 2 volume ratios is methyl alcohol：Dichloromethane=1：2 volume ratios it is mixed
Liquid is closed, the rotten solid-liquid ratio with organic solvent I is 1g/15~30ml；The amount of added water is 0.5 volume times of organic solvent I；
2), sample introduction：
By lipid crude extract methyl alcohol：Dichloromethane=1：The organic solvent of 2 volume ratios is settled to 100mL as sample；
Pipette conduct after 1mL samples cross 0.22 μm of filter membrane and treat sample measuring liquid, mass spectrum is injected into using pin infusion emitter；
3), Mass Spectrometer Method：
Using negative ion mode, all parent ions containing the daughter ion are found according to feature daughter ion, sweep limits is 400-
1000Da, residence time is 2 seconds, and gas curtain gas is 10psi, and accelerating potential is -4500ev, and auxiliary gas I is 20psi, aids in gas II
It is 30psi, collection of illustrative plates is cumulative 100~200 times；Use Analyst software collection data；
4), data analysis：
By step 3) Mass Spectrometer Method gained spectrogram be analyzed, obtain the structural information of each quasi-molecular ions.
2. the method that random measure according to claim 1 contains EPA chain compounds, it is characterized in that：
The step 4) be：
By step 3) Mass Spectrometer Method gained spectrogram by noise filtering, baseline deduction 4Da, after removing isotopic peak, after being processed
Spectrogram；Identified using Lipid Mass Spec.Prediction softwares after spectrogram after treatment is exported as into txt file, you can
To the structural information of each quasi-molecular ions.
3. the method that random measure according to claim 2 contains EPA chain compounds, it is characterized in that：
The step 4) also include：
Each parent ion concentration is through formula：Calculate, wherein
AbundanceiIt is Compound abundance, AiIt is the peak area at the specific ion peak in spectrogram, A1~AnIt is all obtained by spectrogram
The peak area of quasi-molecular ions.
4. according to any method of the described random measure containing EPA chain compounds of claims 1 to 3, it is characterized in that：
The step 1) in, aquatic products tissue is substituted to pipette the centrifugation gains after lower phase solution, with the dichloro in machine solvent I
Methane or chloroform substitute machine solvent I；Repeat extraction 1~3 time；Carried out after the lower phase solution of gained after all extractions is merged
Follow-up drying and redissolution.
5. the method that random measure according to claim 4 contains EPA chain compounds, it is characterized in that：
The step 1) in, it is with refrigerated centrifuge centrifugation：It is centrifuged 5~15 minutes in 4 DEG C, 8000~12000rpm.
6. the method that random measure according to claim 4 contains EPA chain compounds, it is characterized in that：
The step 2) in, pin infusion emitter flow velocity is 10~20 μ L/min.
7. the method that random measure according to claim 4 contains EPA chain compounds, it is characterized in that：
The step 3) in, the scan method for being used looks for female scanning for son, and feature daughter ion is m/z 301, go cluster voltage for-
80~-100ev, collision voltage is -30~-40ev.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111812248A (en) * | 2020-07-23 | 2020-10-23 | 浙江工商大学 | Analysis and detection method for effectively screening phospholipids in krill oil |
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