CN106188066A - The extraction of a kind of Antarctic krill non-phenol alkalescence alkaloid and detection method - Google Patents
The extraction of a kind of Antarctic krill non-phenol alkalescence alkaloid and detection method Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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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- 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
- G01N2030/025—Gas chromatography
Abstract
The invention discloses extraction and the detection method of a kind of Antarctic krill non-phenol alkalescence alkaloid, this extracting method includes that Antarctic krill is contacted with methanol and extracts by (1), filters, obtains filtrate；Filtrate evaporation and concentration obtains methanol cream；(2) methanol cream is contacted with ether and extract, filter, obtain ether solution；Ether extractum is obtained after ether solution evaporation；(3) ether extractum is contacted with ether and dissolve, obtain ether extractum liquid so that it is contact with aqueous acid and extract, sour water phase is obtained by extraction；(4) sour water phase is contacted with chloroform and extract, isolated chloroform layer A；(5) chloroform layer A is contacted with sodium hydrate aqueous solution and extract, isolated aqueous alkali layer and chloroform layer B；(6) by chloroform layer B evaporation of solvent, Antarctic krill non-phenol alkalescence alkaloid sample is i.e. obtained.Antarctic krill alkaloid is carried out extracting detection, three kinds of active alkaloids DTDP, Cyclo of isolated (Pro Leu) and Cyclo (Pro Phe) by the present invention first.
Description
Technical field
The present invention relates to extraction and the detection method of a kind of Antarctic krill non-phenol alkalescence alkaloid, belong to food, medicine
And chemical field.
Background technology
Antarctic krill (Euphausia superba Dana), is subordinate to Arthropoda, Crustachia, Euphausiacea, and build is relatively
Little, general body is about 5.5～6.0cm, body weight about about 2g.It is whale, sea dog, penguin etc. with the Antarctic krill that phytoplankton is food
The Major Foods of carnivore, is also the basis in the food chain of the South Pole.Antarctic krill is that on the earth, the procreation of quantity maximum is the most successful
One of single living resources, its biological reserves are about 6.5 × 108～10 × 108Ton, up-to-date estimator is 3.79 × 108
Ton.In food shortage, in the case of world fisheries resource atrophy, especially China coastal waters exploitation excessively, Antarctic krill without
It is suspected to be a kind of fishery resources overseas with huge potentiality to be exploited.Antarctic krill is nutritious, rich in active substance.Antarctic krill
Albumen and enzyme, astaxanthin, chitin etc. studies have reported that the most.Along with going deep into of Antarctic krill research, Antarctic krill product
Also developed to high-end health care, field of medicaments by primary feedstuff shrimp meal etc..Accelerate Antarctic krill research progress and be conducive to China
Superiority is occupied in terms of Antarctic krill industry.
Alkaloid mostlys come from plant, also known as plant alkaloid, has analgesia, alleviates spasm, antibacterial, antiinflammatory, blood pressure lowering, flat
Breathe heavily, the effect such as antitumor.Zoogenous alkaloid is in addition to amphibian animal, only some marine organisms, as sponge, Corallium Japonicum Kishinouye,
Existing in Marine microorganism and mouth mqb shrimp, wherein the structure of mouth mqb shrimp alkaloid has not determined.Marine organisms are special because of it
Living environment and have the metabolic pathway that is different from terrestrial organism, always find new drug guide natural treasure-house.Have in the world
The medicament sources Yu Haiyang of 70%.In Antarctic krill, bioactive substance enriches, the low temperature survived with it, the special ocean of less salt
Living environment has some relations.Though having in supposition Antarctic krill containing alkaloid, but do not understand the kind of alkaloid, and at present
Pertinent literature or patent report is not also had about the alkaloid in Antarctic krill.Therefore, the kind of Antarctic krill alkaloid is studied
And the extraction of alkaloid and detection method, the exploitation of Antarctic krill resource are had and is of great significance.
Summary of the invention
For above-mentioned prior art, it is an object of the invention to provide carrying of a kind of Antarctic krill non-phenol alkalescence alkaloid
Take and detection method.
For achieving the above object, the present invention uses following technical proposals:
First purpose of the present invention is to provide the extracting method of a kind of Antarctic krill non-phenol alkalescence alkaloid, step
As follows:
(1) Antarctic krill is contacted with methanol and extract, filter, obtain filtrate；Filtrate evaporation and concentration obtains methanol cream；
(2) the methanol cream in step (1) is contacted with ether and extract, filter, obtain ether solution；After ether solution evaporation
Obtain ether extractum；
(3) the ether extractum in step (2) is contacted with ether and dissolve, obtain ether extractum liquid so that it is with sour water
Solution contacts and extracts, and sour water phase is obtained by extraction；
(4) the sour water phase in step (3) is contacted with chloroform and extract, isolated chloroform layer A；
(5) the chloroform layer A in step (4) is contacted with sodium hydrate aqueous solution and extract, isolated aqueous alkali layer
With chloroform layer B；
(6) by the chloroform layer B evaporation of solvent in step (5), Antarctic krill non-phenol alkalescence alkaloid is i.e. obtained
Sample.
In step (1), Antarctic krill first passes through lyophilization before contact methanol extraction and processes.Due in Antarctic krill body
Enzyme there is the highest activity, after Antarctic krill is fished for, its internal endogenous digestive enzyme can highly active protein degradation matter, make
Tissue fast decoupled after death, accelerates the self-dissolving of Antarctic krill, corruption and goes bad；It is freezing dry by Antarctic krill is carried out
Dry pretreatment, it is possible to prevent Antarctic krill self-dissolving, the effective quality keeping Antarctic krill.
In step (1), the ratio of described Antarctic krill and methanol addition is 1g:(6-10) mL, Extracting temperature is 75～85
DEG C, preferably 80 DEG C, the number of times of methanol extraction is 7-9 time, and the time of extraction is 1-2h every time, and extracting mode can be reflux, extract,
Or stirring extraction.The number of times that methanol eddy extracts is elected as 7-9 time, it is possible to it is raw that separation and Extraction as much as possible goes out non-phenol alkalescence
Alkaloids.
In step (2), the ratio of described methanol cream and ether addition is 1g:(4-6) mL, the number of times adding ether extraction is
4-6 time, the time of extraction is 0.5-1h every time.The extraction time of ether is elected as 4-6 time, not only efficiently separates out in Antarctic krill
Non-phenol alkalescence alkaloid, moreover it is possible to reduce the energy waste that the increase of extraction time is brought as far as possible.
In step (3), different condition gained ether extractum amount is different, and the amount adding ether when ether redissolves can be according to reality
Border situation is adjusted.The addition of general described ether extractum and ether is than for 1g:8～12mL (preferably 1g:10mL), ether
Appropriate ether dissolution first used by cream, then extracts with sour water, can increase the contact area with sour water, it is ensured that alkaline matter is substantially soluble in
Sour water layer.
Ether is easy to rotation and steams, even if all dividing exactly, the time of cost is the shortest.Next tests discovery, steams with rotation and retains
Ether ether extract can not be made all to dissolve.
In step (3), described aqueous acid is that aqueous sulfuric acid or aqueous tartaric acid solution, preferably sulphuric acid are water-soluble
Liquid；Described ether extractum liquid is 1:(10-30 with the volume ratio of aqueous acid addition).The volume fraction of described aqueous sulfuric acid
It is 1～3%, it is preferred that the volume fraction of described aqueous sulfuric acid is 2%, selects the aqueous sulfuric acid of this concentration both to can guarantee that
Enough acidity, to remove acid impurities, prevents again the too high oxidation Decomposition causing goal object of sulfuric acid concentration.
In step (4), the volume ratio of described sour water phase and chloroform is 1～2:1, it is preferred that described sour water layer and chloroform
Volume ratio is 1:1.Chloroform is 6-8 time with the stirring extraction times of sour water phase, and each mixing time is 1～1.5h (preferably to stir
Time is 1h), fully mix, make target substance be dissolved in chloroform layer as far as possible.
When the extractant of the extraction process of the present invention is chloroform, not only in terms of extraction efficiency, separatory but also in extraction
Take the accessibility aspect of solvent, particularly preferably.In step (5), the volume ratio of described chloroform layer A and sodium hydrate aqueous solution is
1～2:1, it is preferred that the volume ratio of described chloroform layer A and sodium hydrate aqueous solution is 1:1.The body of described sodium hydrate aqueous solution
Fraction is 1～3%.
The stirring extraction times adding chloroform and sodium hydrate aqueous solution is 6-8 time, and each mixing time is 1～1.5h
(preferably 1h), fully mixes, and removes faintly acid impurity as far as possible.
Alr mode in the present invention is mechanical agitation or magnetic agitation.
The mode using separatory funnel to carry out standing separatory in the present invention extracts.
Second object of the present invention is to provide the Antarctic krill non-phenol weak base using said extracted method to prepare
Property alkaloid sample, wherein, described sample comprises three kinds of non-phenol alkalescence alkaloids, is 5 respectively, 10-dimethoxy-2, and 3,
7,8-tetrahydrochysene-1H, 6H-pyrrolo-[1,2-a；1 ', 2 '-d] pyrazine (5,10-diethoxy-2,3,7,8-tetrahydro-1H,
6H-dipyrrolo[1,2-a；1 ', 2 '-d] pyrazine, be called for short DTDP), pyrrolo-[1,2-a] pyrazine-1,4-diketone, six
Hydrogen-3-(2-methyl-propyl) { Cyclo (Pro-Leu) }, pyrrolo-[1,2-a] pyrazine-1,4-diketone, hexahydro-3-(phenyl first
Base) { Cyclo (Pro-Phe) }.
It is raw that third object of the present invention is to provide a kind of Antarctic krill using said method to extract non-phenol alkalescence
The detection method of alkaloids, the method uses gas chromatography-mass spectrography (GC-MS) to analyze detection, and testing conditions is: DB-1 chromatograph
Post；Carrier gas: helium；Flow velocity: 0.8～1.2mL/min, solvent delay 2～2.2min；Heating schedule: initial temperature is 45～55
DEG C, be warmed up to 55～65 DEG C with 1.8～2.2 DEG C/min, then be raised to 240～260 DEG C with 25～35 DEG C/min, keep 5～
10min.Ionization mode: EI, 60～80eV；Ion source temperature: 240～260 DEG C；Carrier gas: helium；Column flow rate: 0.8～
1.2mL/min.Conditions above be to by the kind of separation detection material and character and indefinite in the case of, the present inventor
Through great many of experiments and analysis, carry out the chromatography-mass spectroscopy condition groping to obtain.
Preferably, for efficiently separating the material composition that Detection and Extraction obtain, described testing conditions is: DB-1 chromatographic column, type
Number it is 30m × 0.25mm × 0.25 μ L；Carrier gas: helium；Flow velocity: 1mL/min, solvent delay 2.06min；Heating schedule: initial
Temperature is 50 DEG C, is warmed up to 60 DEG C with 2 DEG C/min, then is raised to 250 DEG C with 30 DEG C/min, keeps 8min.Ionization mode: EI,
70eV；Ion source temperature: 250 DEG C；Carrier gas: helium；Column flow rate: 1.0mL/min.
A technical scheme in the present invention has a following beneficial effect:
(1) present invention uses above extraction and detection method, finds three kinds of non-phenol alkalescence alkaloids first, and from south
Pole krill extracts the non-phenol alkalescence alkaloid compared with strong biological activity of having of three kinds of stable existences of isolated: 5,
10-dimethoxy-2,3,7,8-tetrahydrochysene-1H, 6H-pyrrolo-[1,2-a；1 ', 2 '-d] pyrazine (5,10-diethoxy-2,3,7,
8-tetrahydro-1H,6H-dipyrrolo[1,2-a；1 ', 2 '-d] pyrazine, it is called for short DTDP)；Pyrrolo-[1,2-a] pyrrole
Piperazine-1,4-diketone, hexahydro-3-(2-methyl-propyl) { Cyclo (Pro-Leu) }；Pyrrolo-[1,2-a] pyrazine-1,4-diketone, six
Hydrogen-3-(phenyl methyl) { Cyclo (Pro-Phe) }.Research through the present invention obtains, Antarctic krill is primarily present three kinds non-
Phenol alkalescence alkaloid, is of great significance the exploitation tool of Antarctic krill resource.
(2) the present invention is directed to this specific marine feedstock of Antarctic krill, through substantial amounts of experiment and analysis, exploratory development
Obtaining a kind of extraction ratio and the of a relatively high extracting method of purity, this extracting method is simple, and the non-phenol alkalescence obtained is biological
The total amount purity of alkali is up to more than 60%, and wherein the purity of DTDP is up to more than 47%, the purity of Cyclo (Pro-Leu) up to
The purity of more than 20%, Cyclo (Pro-Phe) is up to more than 10%.
(3) present invention is by substantial amounts of experiment and analysis, have selected the gas chromatography-mass spectrography (GC-with certain parameter
MS) the unknown alkali extracted being analyzed detection, this detection method can separate and detect the kind of alkaloid effectively, accurately
Class and content.
Accompanying drawing explanation
Fig. 1 is the GC-MS total ions chromatogram of embodiment 1 sample；
Fig. 2 is the GC-MS total ions chromatogram of embodiment 2 sample；
Fig. 3 is the GC-MS total ions chromatogram of embodiment 3 sample.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is further illustrated, it should explanation, and the description below is merely to solve
Release the present invention, its content is not defined.
Embodiment 1
Weigh the cryodesiccated Antarctic krill of 100g, add methanol 800ml, 80 degrees Celsius of reflux, extract, 7 times, each 1h,
Colourless to lixiviating solution.Filtering, filtrate rotation obtains methanol cream after steaming.In methanol cream, add ether extract 4 times, each 1h, filter
Ether extract；Ether extractum is obtained after ether extract concentrated by rotary evaporation.Ether extractum adds appropriate ether dissolution, and ratio is 1g:
10mL, adds the H that volume fraction is 2% of 10 times of volumes2SO4Aqueous solution stirring extraction, separatory obtains sour water layer.To sour water layer
Adding isopyknic chloroform stirring extraction 6 times, stir 1h every time, after standing, separatory obtains chloroform layer A.Addition etc. in chloroform layer A
The volume fraction of volume is 2%NaOH aqueous solution stirring extraction 6 times, stirs 1h every time, and after standing, separatory obtains chloroform layer B.Chloroform
After layer B is evaporated chloroform, obtain sample 1, about 17.78mg.
Using GC-MS method to detect material composition in sample 1, testing conditions is as follows:
Detecting instrument: Agilent 7890GC-5975MS；
GC-MS condition: DB-1 chromatographic column (30m × 0.25mm × 0.25 μ L)；Carrier gas: helium；Flow velocity: 1mL/min, solvent
Postpone 2.06min；Heating schedule: initial temperature is 50 DEG C, is warmed up to 60 DEG C with 2 DEG C/min, then is raised to 250 with 30 DEG C/min
DEG C, keep 8min.Ionization mode: EI, 70eV；Ion source temperature: 250 DEG C；Carrier gas: helium；Column flow rate: 1.0mL/min；Enter
Sample loading mode: shunting, ratio 50:1；Sampling volume: 0.2 μ L.
After testing, main non-phenol alkalescence alkaloid component such as table 1 below in gained sample, to GC-MS total ion current color
Spectrogram is as shown in Figure 1.
Table 1:GC-MS analyzes principal alkaloid constituents in sample 1
From table 1 and Fig. 1 it can be seen that the extracting method of the present embodiment isolated three kinds from Antarctic krill is stably deposited
There is the non-phenol alkalescence alkaloid compared with strong biological activity, the relative amount of three kinds of alkaloids is higher.
Embodiment 2
Weigh the cryodesiccated Antarctic krill of 100g, add methanol 1000ml, 80 degrees Celsius of reflux, extract, 8 times, every time
1.5h, colourless to lixiviating solution.Filtering, filtrate rotation obtains methanol cream after steaming.In methanol cream, add ether extract 5 times, each 1h, mistake
Filter to obtain ether extract；Ether extractum is obtained after ether extract concentrated by rotary evaporation.Ether extractum add appropriate ether dissolution (1g:
10mL), the H that volume fraction is 1% of 20 times of volumes is added2SO4Aqueous solution stirring extraction, separatory obtains sour water layer.To sour water layer
Adding isopyknic chloroform stirring extraction 7 times, stir 1h every time, after standing, separatory obtains chloroform layer A.Addition etc. in chloroform layer A
The volume fraction of volume is 1%NaOH aqueous solution stirring extraction 7 times, stirs 1h every time, and after standing, separatory obtains chloroform layer B.Chloroform
After layer B is evaporated chloroform, obtain sample 2, about 17.81mg.
Using GC-MS method to detect material composition in sample, detection method is with embodiment 1.After testing, gained sample
Middle principal alkaloid constituents such as table 2 below, corresponding mass spectrum and structure such as Fig. 2.
Table 2:GC-MS analyzes principal alkaloid constituents in sample 2
From table 2 and Fig. 2 it can be seen that the extracting method of the present embodiment isolated three kinds from Antarctic krill is stably deposited
There is the non-phenol alkalescence alkaloid compared with strong biological activity.
Embodiment 3
Weigh the cryodesiccated Antarctic krill of 100g, add methanol 600ml, 80 degrees Celsius of reflux, extract, 9 times, each 2h,
Colourless to lixiviating solution.Filtering, filtrate rotation obtains methanol cream after steaming.In methanol cream, add ether extract 6 times, each 0.5h, filter
Obtain ether extract；Ether extractum is obtained after ether extract concentrated by rotary evaporation.Ether extractum adds appropriate ether dissolution (1g:10mL),
Add the H that volume fraction is 3%2SO4Aqueous solution stirring extraction, separatory obtains sour water layer.Isopyknic chloroform is added to sour water layer
Stirring extraction 8 times, stirs 1h every time, and after standing, separatory obtains chloroform layer A.Adding isopyknic volume fraction in chloroform layer A is
3%NaOH aqueous solution stirring extraction 8 times, stirs 1h every time, and after standing, separatory obtains chloroform layer B.After chloroform layer B is evaporated chloroform,
Sample 3, about 17.76mg.
Using GC-MS method to detect material composition in sample, detection method is with embodiment 1.After testing, gained sample
Middle principal alkaloid constituents such as table 3 below, corresponding mass spectrum and structure such as Fig. 3.
Table 3:GC-MS analyzes principal alkaloid constituents in sample 3
From table 3 and Fig. 3 it can be seen that the extracting method of the present embodiment isolated three kinds from Antarctic krill is stably deposited
There is the non-phenol alkalescence alkaloid compared with strong biological activity.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not by above-described embodiment
Limit, the change made under other any spirit without departing from the present invention and principle, modify, substitute, combine, simplify,
All should be the substitute mode of equivalence, within being included in protection scope of the present invention.
Claims (10)
1. an extracting method for Antarctic krill non-phenol alkalescence alkaloid, is characterized in that, step is as follows:
(1) Antarctic krill is contacted with methanol and extract, filter, obtain filtrate；Filtrate evaporation and concentration obtains methanol cream；
(2) the methanol cream in step (1) is contacted with ether and extract, filter, obtain ether solution；Obtain after ether solution evaporation
Ether extractum；
(3) the ether extractum in step (2) is contacted with ether and dissolve, obtain ether extractum liquid so that it is with aqueous acid
Contact and extract, sour water phase is obtained by extraction；
(4) the sour water phase in step (3) is contacted with chloroform and extract, isolated chloroform layer A；
(5) the chloroform layer A in step (4) is contacted with sodium hydrate aqueous solution and extract, isolated aqueous alkali layer and chlorine
Imitative layer B；
(6) by the chloroform layer B evaporation of solvent in step (5), Antarctic krill non-phenol alkalescence alkaloid sample is i.e. obtained.
2. extracting method as claimed in claim 1, is characterized in that: in step (1), and Antarctic krill is first before contact methanol extraction
Process through lyophilization.
3. extracting method as claimed in claim 1, is characterized in that: in step (1), described Antarctic krill and methanol addition
Ratio is 1g:(6-10) mL, Extracting temperature is 75～85 DEG C, and the number of times of methanol extraction is 7-9 time, and the time of extraction is 1-every time
2h, extracting mode is reflux, extract, or stirring extraction.
4. extracting method as claimed in claim 1, is characterized in that: in step (2), described methanol cream and the ratio of ether addition
For 1g:(4-6) mL, the number of times adding ether extraction is 4-6 time, and the time of extraction is 0.5-1h every time.
5. extracting method as claimed in claim 1, is characterized in that: in step (3), and described ether extractum liquid adds with aqueous acid
The volume ratio entering amount is 1:(10-30)；Preferably, described aqueous acid is aqueous sulfuric acid or aqueous tartaric acid solution, further
Preferably, the volume fraction of described aqueous sulfuric acid is 1～3%.
6. extracting method as claimed in claim 1, is characterized in that: in step (4), and the volume ratio of described sour water phase and chloroform is
1～2:1, chloroform is 6-8 time with the stirring extraction times of sour water phase, and each mixing time is 1～1.5h.
7. extracting method as claimed in claim 1, is characterized in that: in step (5), and described chloroform layer A and sodium hydroxide are water-soluble
The volume ratio of liquid is 1～2:1, and the volume fraction of described sodium hydrate aqueous solution is 1～3%；Add chloroform and sodium hydroxide water
The stirring extraction times of solution is 6-8 time, and each mixing time is 1～1.5h.
8. use the Antarctic krill non-phenol alkalescence alkaloid that the method according to any one of claim 1～7 prepares
Sample, is characterized in that: this sample comprises three kinds of non-phenol alkalescence alkaloids, is 5 respectively, 10-dimethoxy-2,3,7,8-tetra-
Hydrogen-1H, 6H-pyrrolo-[1,2-a；1 ', 2 '-d] pyrazine, pyrrolo-[1,2-a] pyrazine-1,4-diketone, hexahydro-3-(2-methyl
Propyl group) and pyrrolo-[1,2-a] pyrazine-1,4-diketone, hexahydro-3-(phenyl methyl).
9. the method according to any one of claim 1～7 extracts the detection method of the alkaloid obtained, and it is characterized in that: the party
Method uses gas chromatography-mass spectrography, and testing conditions is: DB-1 chromatographic column, carrier gas: helium.
10. detection method as claimed in claim 9, is characterized in that, the method also includes following testing conditions: flow velocity: 0.8～
1.2mL/min, solvent delay 2～2.2min；Heating schedule: initial temperature is 45～55 DEG C, heats up with 1.8～2.2 DEG C/min
To 55～65 DEG C, then it is raised to 240～260 DEG C with 25～35 DEG C/min, keeps 5～10min；Ionization mode: EI, 60～
80eV；Ion source temperature: 240～260 DEG C；Carrier gas: helium；Column flow rate: 0.8～1.2mL/min.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106248822A (en) * | 2016-07-19 | 2016-12-21 | 山东师范大学 | Pyrrolo-[1,2 a] pyrazine 1,4 diketone in a kind of Antarctic krill, the extraction purification of hexahydro 3 (phenyl methyl) and detection method |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037153A (en) * | 2015-07-23 | 2015-11-11 | 山东师范大学 | Method for preparing DBP through waste liquid generated by antarctic krill alkaloid extraction |
| CN105130836A (en) * | 2015-07-23 | 2015-12-09 | 山东师范大学 | Method of preparing acetamide from waste liquid of extracting alkaloid from Antarctic krill |
| CN105130809A (en) * | 2015-07-23 | 2015-12-09 | 山东师范大学 | Method of preparing dioctyl adipate from waste liquid through extraction of alkaloid from euphausia superba |
-
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105037153A (en) * | 2015-07-23 | 2015-11-11 | 山东师范大学 | Method for preparing DBP through waste liquid generated by antarctic krill alkaloid extraction |
| CN105130836A (en) * | 2015-07-23 | 2015-12-09 | 山东师范大学 | Method of preparing acetamide from waste liquid of extracting alkaloid from Antarctic krill |
| CN105130809A (en) * | 2015-07-23 | 2015-12-09 | 山东师范大学 | Method of preparing dioctyl adipate from waste liquid through extraction of alkaloid from euphausia superba |
Non-Patent Citations (8)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106248822A (en) * | 2016-07-19 | 2016-12-21 | 山东师范大学 | Pyrrolo-[1,2 a] pyrazine 1,4 diketone in a kind of Antarctic krill, the extraction purification of hexahydro 3 (phenyl methyl) and detection method |
| CN106248822B (en) * | 2016-07-19 | 2018-08-28 | 山东师范大学 | Pyrrolo- [1,2-a] pyrazine -1,4- diketone in a kind of krill, the extraction purification and detection method of hexahydro -3- (phenyl methyl) |
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