CN106279179B - A kind of krill DTDP extraction purification and detection method - Google Patents

A kind of krill DTDP extraction purification and detection method Download PDF

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Publication number
CN106279179B
CN106279179B CN201610569991.4A CN201610569991A CN106279179B CN 106279179 B CN106279179 B CN 106279179B CN 201610569991 A CN201610569991 A CN 201610569991A CN 106279179 B CN106279179 B CN 106279179B
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extraction
ether
purification
krill
extracted
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CN106279179A (en
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王翩翩
刘代成
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Shandong Normal University
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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
    • 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

Abstract

The present invention discloses a kind of krill DTDP extraction purification and detection method, and this method includes contacting krill with methanol and being extracted, filtered；Filtrate is concentrated by evaporation to obtain methanol cream；Methanol cream is contacted with ether and extracted, is filtered；Ether medicinal extract is obtained after ether solution evaporation；Ether medicinal extract is contacted with ether and dissolved, ether medicinal extract liquid is obtained, it is contacted and is extracted with aqueous acid, sour water phase is obtained by extraction；Sour water phase is contacted with chloroform and extracted, isolated chloroform layer A；Chloroform layer A is contacted with sodium hydrate aqueous solution and extracted, isolated buck layer and chloroform layer B；By chloroform layer B evaporation of solvent, it is molten to add petroleum ether leaching, is filtrated to get petroleum ether leaching liquor；By petroleum ether leaching liquor evaporation of solvent, DTDP is obtained.The present invention is found that DTDP in krill first, and extraction detection has been carried out to it.

Description

A kind of krill DTDP extraction purification and detection method
Technical field
The present invention relates to a kind of krill 5,10- dimethoxys -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a； 1 ', 2 '-d] pyrazine extraction purification and detection method, category food, medicine and chemical field.
Background technology
Krill (Euphausia superba Dana), is subordinate to Arthropoda, Crustachia, Euphausiacea, build compared with Small, general body is about 5.5~6.0cm, body weight about 2g or so.Antarctic organism species is less, but substantial amounts, and food chain is also relative Simply.Krill using phytoplankton as food is the Major Foods of the carnivores such as whale, sea dog, penguin, and South Pole food Basis in chain.Krill, which is that quantity is maximum on the earth, multiplies one of most successful single living resources, its biological reserves About 6.5 × 108~10 × 108Ton, newest estimator are 3.79 × 108Ton.In food shortage, world fisheries resource atrophy, especially In the case that it is China coastal waters exploitation excessively, krill is undoubtedly a kind of fishery overseas with huge potentiality to be exploited Resource.Krill is nutritious, rich in active material.Krill albumen and enzyme, astaxanthin, chitin etc. have been ground Study carefully report.With going deep into for krill research, krill product is also from feed shrimp med etc. of primary to high-end health care, doctor Medicine field is developed.Quickening krill research progress is advantageous to China and occupies superiority in terms of krill industry.
5,10- dimethoxy -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo-es [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, abbreviation DTDP) Act on, be found in microorganism, grub, tealeaves etc. also contain DTDP more with obvious anti-inflammatory, antitumor etc..At present in the world The research for not having krill DTDP also is reported.Therefore whether DTDP and its extraction and detection are contained in research krill Method, this to krill active material exploitation, improve its added value tool be of great significance.
The content of the invention
For above-mentioned prior art, it is an object of the invention to provide a kind of krill 5,10- dimethoxys -2,3,7,8- Tetrahydrochysene -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine method for extraction and purification.
To achieve the above object, the present invention uses following technical proposals：
A kind of krill 5,10- dimethoxys -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrrole The method for extraction and purification of piperazine, step are as follows：
(1) krill is contacted with methanol and extracted, filtered, obtain filtrate；Filtrate is concentrated by evaporation to obtain methanol cream；
(2) the methanol cream in step (1) is contacted with ether and extracted, filtered, obtain ether solution；After ether solution evaporation Obtain ether medicinal extract；
(3) the ether medicinal extract in step (2) is contacted with ether and dissolved, obtained ether medicinal extract liquid, make itself and sour water Solution is contacted and extracted, and sour water phase is obtained by extraction；
(4) the sour water phase in step (3) is contacted with chloroform and extracted, isolated chloroform layer A；
(5) the chloroform layer A in step (4) is contacted with sodium hydrate aqueous solution and extracted, isolated buck layer With chloroform layer B；
(6) by the chloroform layer B evaporation of solvent in step (5), preextraction thing is obtained, it is contacted and is entered with petroleum ether Row leaching is molten, is filtrated to get petroleum ether leaching liquor；
(7) 5,10- dimethoxys -2,3 are obtained by the petroleum ether leaching liquor evaporation of solvent in step (6), 7,8- tetra- Hydrogen -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine.
In step (1), krill first passes through freeze-drying process before contact methanol extraction.Due in krill body Enzyme there is very high activity, after krill is caught, the protein degradation matter of its internal endogenous digestive ferment energy high activity, make Tissue fast decoupled after death, accelerate the self-dissolving of krill, corruption and rotten；It is dry by carrying out freezing to krill Dry pretreatment, krill self-dissolving can be prevented, the effective quality for keeping krill, so as to effectively extract 5,10- Dimethoxy -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine.
In step (1), the ratio of krill and the methanol addition is 1g:(6-10) mL, Extracting temperature are 75~85 DEG C, preferably 80 DEG C, the number of methanol extraction is 7-9 times, and the time extracted every time is 1-2h, and extracting mode can be refluxing extraction Or stirring extraction.Methanol eddy extraction number elect as 7-9 times, can separation and Extraction as much as possible go out 5,10- dimethoxys- 2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine.
In step (2), the ratio of the methanol cream and ether addition is 1g:(4-6) mL, the number for adding ether extraction are 4-6 times, the time extracted every time is 0.5-1h.The extraction time of ether is elected as 4-6 times, is not only efficiently separated out in krill 5,10- dimethoxy -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo-es [1,2-a；1 ', 2 '-d] pyrazine, moreover it is possible to extraction is reduced as far as possible Energy waste caused by the increase of number.
In step (3), ether medicinal extract amount is different obtained by different condition, and the amount that ether is added when ether redissolves can be according to reality Border situation is adjusted.The addition ratio of general the ether medicinal extract and ether is 1g：8~12mL (preferably 1g:10mL), ether Cream extracts first with appropriate ether dissolution, then with sour water, can increase the contact area with sour water, ensure that alkaline matter is substantially soluble in Sour water layer.
Ether is easy to rotate, even if all dividing exactly, the time of cost is also shorter.Secondly experiment is found, is retained with revolving Ether can not make ether extract all dissolve.
In step (3), the aqueous acid is aqueous sulfuric acid or aqueous tartaric acid solution, and preferably sulfuric acid is water-soluble Liquid；The volume ratio of the ether medicinal extract liquid and aqueous acid addition is 1:(10-30).The volume fraction of the aqueous sulfuric acid For 1~3%, it is preferred that the volume fraction of the aqueous sulfuric acid is 2%, selects the aqueous sulfuric acid of the concentration both to can guarantee that Enough is acid to remove acid impurities, prevents the too high oxidation Decomposition for causing purpose thing of sulfuric acid concentration again.
In step (4), the volume ratio of the sour water phase and chloroform is 1~2：1, it is preferred that the sour water layer and chloroform Volume ratio is 1：1.The stirring extraction times of chloroform and sour water phase are 6-8 times, and each mixing time is that 1~1.5h (is preferably stirred Time is 1h), fully mix, target substance is dissolved in chloroform layer as far as possible.
When the extractant of extraction process of the present invention is chloroform, not only in terms of extraction efficiency, liquid separation but also extracting In terms of the accessibility for taking solvent, particularly preferably.
In step (5), the volume ratio of the chloroform layer A and sodium hydrate aqueous solution are 1~2：1, it is preferred that the chloroform The volume ratio of layer A and sodium hydrate aqueous solution is 1：1.The volume fraction of the sodium hydrate aqueous solution is 1~3%.
The stirring extraction times for adding chloroform and sodium hydrate aqueous solution are 6-8 times, and each mixing time is 1~1.5h (being preferably 1h), fully mixes, removes faintly acid impurity as far as possible.
In step (6), the mass volume ratio of the preextraction thing and petroleum ether is 1mg:1-3mL, add after petroleum ether gently Shake, leaching is molten, and guarantee makes target substance be dissolved in petroleum ether as far as possible.
From the viewpoint of effective purifying, the present invention preferably selects petroleum ether so that the purity of DTDP after purification compared with It is high.
Agitating mode in the present invention is mechanical agitation or magnetic agitation.
For the specific method of extraction, extracting process known to use can be included and extracted, such as can include and adopt With separatory funnel stand method for being extracted of mode of liquid separation etc..
It is prepared using said extracted purification process containing 5,10- dimethoxy -2,3,7,8- tetrahydrochysene -1H, 6H- pyrroles And [1,2-a；1 ', 2 '-d] pyrazine sample.
The present invention also provides a kind of krill 5,10- dimethoxys -2,3,7,8- using above method extraction purification Tetrahydrochysene -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine detection method, this method uses gas chromatography-mass spectrography (GC- MS) analysis detection, testing conditions are：DB-1 chromatographic columns；Carrier gas：Helium；Flow velocity：0.8~1.2mL/min, solvent delay 2~ 2.2min；Heating schedule：Initial temperature is 45~55 DEG C, and 55~65 DEG C are warming up to 1.8~2.2 DEG C/min, then with 25~35 DEG C/min is raised to 240~260 DEG C, keep 5~10min.Ionization mode:EI, 60~80eV；Ion source temperature:240~260 ℃；Carrier gas:Helium；Column flow rate：0.8~1.2mL/min.Conditions above is that the present inventor is touched by many experiments with analysis The chromatography-mass spectroscopy condition that rope obtains.
Preferably, to efficiently separate the material composition that Detection and Extraction obtain, the testing conditions are：DB-1 chromatographic columns, type Number for the μ L of 30m × 0.25mm × 0.25；Carrier gas：Helium；Flow velocity：1mL/min, solvent delay 2.06min；Heating schedule：Initially Temperature is 50 DEG C, and 60 DEG C are warming up to 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℃；Carrier gas:Helium；Column flow rate：1.0mL/min.
A technical scheme in above-mentioned technical proposal has the advantages that：
(1) present invention is using krill as raw material, present invention firstly discovers that contain DTDP in krill, and to South Pole phosphorus Shrimp DTDP has carried out extracting and developing and purifying, and the active material of krill is developed, improve its added value have it is particularly significant Meaning.
(2) present invention is for this specific marine feedstock of krill, by substantial amounts of experiment and analysis, exploratory development A kind of recovery rate and the of a relatively high extracting method of purity are obtained, the extracting method is simple, obtained 5,10- dimethoxy -2, 3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine purity is higher, up to more than 90%.
(3) present invention have selected the gas chromatography-mass spectrography (GC- with certain parameter by largely testing and analyzing MS analysis detection) is carried out to the DTDP of extraction, the detection method effectively, accurately can separate and detect DTDP and its content.
Brief description of the drawings
Fig. 1 is the mass spectrum and structure chart of the sample of embodiment 1；
Fig. 2 is the mass spectrum and structure chart of the sample of embodiment 2；
Fig. 3 is the mass spectrum and structure chart of the sample of embodiment 3.
Embodiment
With reference to embodiment, the present invention is further illustrated, it should which explanation, the description below is merely to solution The present invention is released, its content is not defined.
Embodiment 1
Weigh 100g freeze-drying krill, add methanol 800ml, 80 degrees Celsius of refluxing extractions 7 times, each 1h, It is colourless to leaching liquor.Filtering, filtrate obtain methanol cream after rotating.Ether is added into methanol cream to extract 4 times, each 1h, is filtered Ether extract；Ether medicinal extract is obtained after ether extract concentrated by rotary evaporation.Ether medicinal extract adds 10 times of volume ether dissolutions, adds 10 The volume fraction of times volume is 2% H2SO4Aqueous solution stirring extraction, liquid separation obtain sour water layer.Isometric chlorine is added to sour water layer Imitative stirring extraction 3 times, stirs 1h every time, after standing liquid separation obtain chloroform layer A.Isometric volume fraction is added into chloroform layer A For the 2%NaOH aqueous solution stirring extraction 6 times, stir 1h every time, after standing liquid separation obtain chloroform layer B.After chloroform layer B is evaporated chloroform, Add 1:1(mg:ML) the petroleum ether leaching of volume is molten obtains sample 1, about 3.47mg.
Sample 1 is detected using GC-MS methods to material composition, testing conditions are as follows：
Detecting instrument：Agilent 7890GC-5975MS；
GC-MS conditions：DB-1 chromatographic columns (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 warming up to 60 DEG C with 2 DEG C/min, then be raised to 250 with 30 DEG C/min DEG C, keep 8min.Ionization mode:EI, 70eV；Ion source temperature:250℃；Carrier gas:Helium；Column flow rate：1.0mL/min；Enter Sample loading mode:Shunting, ratio 50:1；Sampling volume:0.2μL.
Sample 1 detects through GC-MS, and the chromatographic peak retrieval matter of matching at retention time 11.882min is 5,10- diformazans Epoxide -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine, its relative amount accounts for 88.82%.Fig. 1 is pair The mass spectrum and structure chart answered.
Embodiment 2
The krill of 100g freeze-dryings is weighed, adds methanol 1000ml, 80 degrees Celsius of refluxing extractions 8 times, every time 1.5h, it is colourless to leaching liquor.Filtering, filtrate obtain methanol cream after rotating.Add ether into methanol cream to extract 5 times, each 1h, mistake Filter to obtain ether extract；Ether medicinal extract is obtained after ether extract concentrated by rotary evaporation.Ether medicinal extract adds 10 times of volume ether dissolutions, then adds The volume fraction for entering 20 times of volumes is 1% H2SO4Aqueous solution stirring extraction, liquid separation obtain sour water layer.Added to sour water layer isometric Chloroform stirring extraction 4 times, stir 1h every time, after standing liquid separation obtain chloroform layer A.Isometric volume is added into chloroform layer A Fraction be the 1%NaOH aqueous solution stirring extraction 7 times, stir 1h every time, after standing liquid separation obtain chloroform layer B.Chloroform layer B is evaporated chloroform Afterwards, 1 is added:2(mg:ML) leaching of volume petroleum ether is molten obtains sample 2, about 3.56mg.
Sample 2 is detected using GC-MS methods to material composition, detection method is the same as embodiment 1.Through being detected at GC-MS, Chromatographic peak retrieval matter of matching at retention time 11.850min is 5,10- dimethoxy -2,3,7,8- tetrahydrochysenes -1H, 6H- Pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine, its relative amount accounts for 90.02%.Fig. 2 is corresponding mass spectrum and structure chart.
Embodiment 3
Weigh 100g freeze-drying krill, add methanol 600ml, 80 degrees Celsius of refluxing extractions 9 times, each 2h, It is colourless to leaching liquor.Filtering, filtrate obtain methanol cream after rotating.Add ether into methanol cream to extract 6 times, each 0.5h, filtering Obtain ether extract；Ether medicinal extract is obtained after ether extract concentrated by rotary evaporation.Ether medicinal extract adds 10 times of volume ether dissolutions, adds Volume fraction is 3% H2SO4Aqueous solution stirring extraction, liquid separation obtain sour water layer.Isometric chloroform, which is added, to sour water layer stirs extraction Take 3 times, stir 1h every time, after standing liquid separation obtain chloroform layer A.It is 3%NaOH that isometric volume fraction is added into chloroform layer A The aqueous solution stirring extraction 7 times, stir 1h every time, after standing liquid separation obtain chloroform layer B.After chloroform layer B is evaporated chloroform, add 1:3(mg: ML) leaching of times volume petroleum ether it is molten sample 3, about 3.52mg.
Sample 3 is detected using GC-MS methods to material composition, detection method is the same as embodiment 1.After testing, retaining Chromatographic peak retrieval matter of matching at time 11.859min is 5,10- dimethoxy -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo-es [1,2-a；1 ', 2 '-d] pyrazine, its relative amount accounts for 88.56%.Fig. 3 is corresponding mass spectrum and structure chart.
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment Limitation, other any Spirit Essences without departing from the present invention with made under principle change, modification, replacement, combine, simplification, Equivalent substitute mode is should be, is included within protection scope of the present invention.

Claims (11)

  1. A kind of 1. krill 5,10- diethoxies -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine Method for extraction and purification, it is characterized in that, step is as follows：
    (1) krill is contacted with methanol and extracted, filtered, obtain filtrate；Filtrate is concentrated by evaporation to obtain methanol cream；
    (2) the methanol cream in step (1) is contacted with ether and extracted, filtered, obtain ether solution；Obtained after ether solution evaporation Ether medicinal extract；
    (3) the ether medicinal extract in step (2) is contacted with ether and dissolved, obtained ether medicinal extract liquid, make itself and aqueous acid Contact and extracted, sour water phase is obtained by extraction；
    (4) the sour water phase in step (3) is contacted with chloroform and extracted, isolated chloroform layer A；
    (5) the chloroform layer A in step (4) is contacted with sodium hydrate aqueous solution and extracted, isolated buck layer and chlorine Imitative layer B；
    (6) by the chloroform layer B evaporation of solvent in step (5), preextraction thing is obtained, it is contacted and is soaked with petroleum ether It is molten, it is filtrated to get petroleum ether leaching liquor；
    (7) 5,10- diethoxies -2,3 are obtained by the petroleum ether leaching liquor evaporation of solvent in step (6), 7,8- tetrahydrochysenes - 1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] pyrazine.
  2. 2. method for extraction and purification as claimed in claim 1, it is characterized in that：In step (1), krill is in contact methanol extraction Before first pass through freeze-drying process；The ratio of krill and the methanol addition is 1g:(6-10) mL, Extracting temperature be 75~ 85 DEG C, the number of methanol extraction is 7-9 times, and the time extracted every time is 1-2h, and extracting mode is refluxing extraction or stirring extraction.
  3. 3. method for extraction and purification as claimed in claim 1, it is characterized in that：In step (2), the methanol cream and ether addition Ratio be 1g:(4-6) mL, the number for adding ether extraction is 4-6 times, and the time extracted every time is 0.5-1h.
  4. 4. method for extraction and purification as claimed in claim 1, it is characterized in that：In step (3), the ether medicinal extract liquid and sour water are molten The volume ratio of liquid addition is 1:(10-30).
  5. 5. method for extraction and purification as claimed in claim 1, it is characterized in that：In step (3), the aqueous acid is that sulfuric acid is water-soluble Liquid or aqueous tartaric acid solution.
  6. 6. method for extraction and purification as claimed in claim 5, it is characterized in that：The volume fraction of the aqueous sulfuric acid be 1~ 3%.
  7. 7. method for extraction and purification as claimed in claim 1, it is characterized in that：In step (4), the volume of the sour water phase and chloroform Than for 1~2：1, chloroform and the stirring extraction times of sour water phase are 6-8 times, and each mixing time is 1~1.5h.
  8. 8. method for extraction and purification as claimed in claim 1, it is characterized in that：In step (5), the chloroform layer A and sodium hydroxide The volume ratio of the aqueous solution is 1~2：1, the volume fraction of the sodium hydrate aqueous solution is 1~3%；Add chloroform and hydroxide The stirring extraction times of sodium water solution are 6-8 times, and each mixing time is 1~1.5h.
  9. 9. method for extraction and purification as claimed in claim 1, it is characterized in that：In step (6), the preextraction thing and petroleum ether Volume ratio is 1mg:1-3mL.
  10. 10. method for extraction and purification as claimed in claim 1, it is characterized in that：What methods described extraction purification obtained contains 5,10- Diethoxy -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo- [1,2-a；1 ', 2 '-d] detection method of pyrazine sample is：Using gas Phase chromatography mass spectrometry, testing conditions are：DB-1 chromatographic columns, carrier gas：Helium.
  11. 11. method for extraction and purification as claimed in claim 10, it is characterized in that, what methods described extraction purification obtained contains 5, 10- diethoxy -2,3,7,8- tetrahydrochysenes -1H, 6H- pyrrolo-es [1,2-a；1 ', 2 '-d] detection method of pyrazine sample also includes Following testing conditions：Flow velocity：0.8~1.2mL/min, 2~2.2min of solvent delay；Heating schedule：Initial temperature is 45~55 DEG C, it is warming up to 55~65 DEG C with 1.8~2.2 DEG C/min, then 240~260 DEG C are raised to 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。
CN201610569991.4A 2016-07-19 2016-07-19 A kind of krill DTDP extraction purification and detection method Expired - Fee Related CN106279179B (en)

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