CN109053420A - A method of extracting DHA and EPA from Copepods - Google Patents
A method of extracting DHA and EPA from Copepods Download PDFInfo
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Abstract
The method that the invention discloses a kind of to extract DHA and EPA from Copepods, includes the following steps: 1) to be homogenized Copepods pretreatment of raw material；2) homogenate is carried out digesting to obtain crude oil liquid for the first time using trypsase, alkali protease and microcrystalline cellulose；3) crude oil liquid is digested to obtain to the free fatty acid 4 containing EPA, DHA for the second time using lipase) by the free fatty acid containing EPA, DHA using urea entraing method separation, extract concentration the highly unsaturated fatty acid containing EPA, DHA；5) the polyunsaturated fatty acid extraction extraction containing EPA, DHA of concentration is subjected to subcritical enzymatic reaction, reaction product is then subjected to supercritical extract, rectification process must be esterified EPA, DHA.Extracting method reaction condition of the present invention is mild, low energy consumption, operating cost is low, and the rate of recovery and purity is high of EPA and DHA can obtain the EPA and DHA under native state, be easy to be digested absorption.
Description
Technical field
The present invention relates to aquatic products mixed fodder technical fields, extract DHA's and EPA from Copepods more particularly, to a kind of
Method.
Technical background
Copepods substantial amounts are the important branch of zooplankter.In natural waters, zooplankter is the master of the fish young
Food source is wanted, the nutritive value n-3 highly unsaturated fatty acid (n-3HUFA) that Copepods is rich in is conducive to the digestion of the fish young
It absorbs, is the essential fatty acid of marine fish larvae, they are especially twenty light dydrocarbon alkene necessary to marine fish larvae normal growth
Sour (EPA, 20:5n-3) and docosahexenoic acid (DHA, 22:6n-3).The shortage or deficiency of EPA and DHA will affect the fishes and shrimps young
Growth and development, survival rate reduces, and vigor is insufficient, and resistance weakens.Fish cannot be linolenic acid (18:3n-3) own biological
EPA and DHA are synthesized, required EPA and DHA can only be absorbed from feed.A large number of studies show that the oar foot of many bank property
Class animal can satisfy demand of the larva and juvenile to HUFA rich in DHA and EPA (about account for contained fatty acid 60%).But
The fatty acid composition type of fish oil is more, contains C14To C22The different fatty acid of saturation degree, moreover, EPA and DHA have
More unsaturated double-bond, chance light and heat are highly unstable, are easy to happen various reactions, such as oxidation, polymerization or degradation, so
It wants rich and EPA and DHA needs more harsh enrichment condition.Generally, the separating and purifying technology of EPA and DHA can divide two major classes, and one
Class is traditional physico-chemical method, and another kind of is enzyme process.Traditional physical-chemical process includes the crystallizing process under low temperature, urea adduct method, molecule
The way of distillation, metal salts as precipitator, silver ion complexation etc., the product that these methods obtain are mostly ethyl ester type and free-fat acid type
Fish oil is not easy to be digested and absorb and there may be security risks.Then, compared with physics and chemical method, enzyme process has one
The advantage of series: firstly, enzymatic is high-efficient, dosage is seldom in large-scale production, and the repetition that immobilised enzymes can be multiple
It utilizes；Moreover enzymic catalytic reaction carries out under mild pH, temperature and pressure, this is outstanding for unstable long-chain n-3HUFA
To be important, under the conditions of common physical and chemical reaction in long-chain n-3HUFA cis-structure double bond be oxidized, cis-trans isomerism, double bond
Displacement and polymerization reaction all easily occur；Finally, enzymic catalytic reaction can reduce the consumption of energy, this epoch right and wrong in energy shortage
It is often necessary.It furtherly, can be to avoid huge equipment and many and diverse since enzymic catalytic reaction can carry out under solvent-free conditions
Process flow, operator can also work under secure conditions.
The prior art such as Authorization Notice No. is the Chinese invention patent of CN 104651422B, is disclosed a kind of from deep-sea fish
The middle method for extracting triglyceride type DHA and EPA, comprising the following steps: crude fish oil is prepared using zymolysis technique, prepares free rouge
Fat acid, the polyunsaturated fatty acid using the separation of urea entraing method containing EPA, DHA, the fatty acid triglycercide for preparing EPA, DHA.
This method can be extracted effectively from deep-sea fish, be enriched with DHA and EPA；Crude fish oil acid value obtained in preparation process is low, thick fish
Esterified fatty acid hydrolysis degree is high in oil, and finally obtained DHA and EPA are glycerol ester type DHA and EPA, and glycerol ester type EPA and
The content of DHA is high.But the rate of recovery of EPA and DHA that obtains of the extracting method and purity are not satisfactory.
Summary of the invention
The purpose of the present invention is to provide a kind of reaction conditions mildly, low energy consumption, operating cost is low, the recycling of EPA and DHA
Rate and purity is high can obtain EPA and DHA under native state, and be easy to be digested absorption extracts DHA's and EPA from Copepods
Method.
The present invention in background technique aiming at the problem that mentioning, the technical solution taken are as follows:
A method of it extracting DHA and EPA from Copepods, includes the following steps:
1) Copepods pretreatment of raw material must be homogenized；
2) homogenate is carried out digesting to obtain crude oil liquid for the first time using trypsase, alkali protease and microcrystalline cellulose；
3) crude oil liquid is digested to obtain to the free fatty acid containing EPA, DHA for the second time using lipase；
4) by the free fatty acid containing EPA, DHA using the separation of urea entraing method, the height containing EPA, DHA for extracting to be concentrated
Spend unsaturated fatty acid；
5) the polyunsaturated fatty acid extraction extraction containing EPA, DHA of concentration is subjected to subcritical enzymatic reaction, it then will be anti-
Answer product progress supercritical extract, rectification process that must be esterified EPA, DHA.The present invention utilizes trypsase and lipase from Copepods
Then middle extraction DHA and EPA separates the polyunsaturated fatty acid containing EPA and DHA using urea entraing method, reaction condition is mild,
Low energy consumption, operating cost is low, the rate of recovery and purity is high of EPA and DHA, then by EPA and DHA esterization it is modified under native state
EPA and DHA, EPA the and DHA property that makes stablizes, can effectively ensure that its nutritional ingredient, be easy to be digested absorption.
Preferably, the specific steps of pretreatment of raw material are as follows: be sufficiently homogenized Copepods with homogenizer, break outside Copepods
Shell discharges content, is then that 1:0.7-0.9 adds water by feed liquid weight ratio, after mixing under the conditions of anaerobic, 78-84 DEG C
Heat 65-85min, it is spare.There is volatile aldehyde since the grease in Copepods can decompose generation under aerobic environment
Class, ketone and alcohol, oxycarbide, epoxides and acid etc lower-molecular substance, to cause unstable, the even acid value of acid value
Apparent increase causes fish oil rancid rotten, therefore, for the oxidative rancidity for avoiding polyunsaturated fatty acid, under anaerobic into
Row heat treatment, oxygen free condition can be inert gas atmosphere, vacuum environment and other common oxygen free conditions, such as nitrogen atmosphere
Deng, by pretreatment of raw material, it is avoided that generation oxidative rancidity, meanwhile, it eliminates and is dropped as caused by acid value increase
The step of low acid value processing.
Preferably, the specific steps digested for the first time are as follows: the pH to 8.0-9.0 of the homogenate after adjusting pretreatment of raw material,
Trypsase, alkali protease and microcrystalline cellulose is added, be protected from light, 45-55 DEG C under the conditions of digest 8-12h, after enzymatic hydrolysis
It is centrifuged 10-15min at 6500-7500rpm, isolates the crude oil liquid in upper liquid.The step makes albumen using protease
Matter and the associations of fat are destroyed, to realize the purpose of the separation and Extraction fish oil from raw material, trypsase, basic protein
Enzyme and microcrystalline cellulose can make the separation of protein and fat more abundant, and grease is discharged completely, improves the recovery rate of grease, together
When can chelate metal ion in crude oil liquid or catalytic metal by aquation, thus prevent crude oil liquid oxygen chemical conversion hydroperoxides and
New free radical, and hydroperoxides and new free radical can effectively be disposed, it avoids that oxidation reaction occurs, reduces gained
The color and its oxidation stability of crude oil liquid, and mainly exist as a triglyceride, the quality of crude oil liquid obtained is improved, is
The rate of recovery for improving DHA and EPA is laid the groundwork, while can also be by the polypeptide and amino acid of high level in lower layer's enzymolysis liquid into one
Step exploitation improves the utility value of Copepods at fertilizer, feed or seasoning class product.
Further preferably, the enzyme concentration of trypsase and alkali protease is 150-250U/g and 250-350U/g, crystallite
The weight ratio of cellulose and alkali protease is 1:2.5-3.4.
Preferably, the specific steps of second of enzymatic hydrolysis are as follows: be by enzyme concentration by being digested in obtained crude oil liquid for the first time
1.5-3.0% be added lipase, be protected from light, 45-55 DEG C under the conditions of digest 15-19h to get the free fatty acid containing EPA, DHA.
EPA and DHA etc. is connected on the 2nd of glycerol backbone in triglycerides mostly, and saturation or low insatiable hunger are connected on 1 and 3
With the fatty acid of degree, therefore, it is necessary to carry out second to crude oil liquid to digest, and there are carbon-carbon double bonds in monounsaturated fatty acid molecule
And full cis-configuration, cause the bending of entire chain, therefore the most end on the cruel molecule of glycerol in unsaturated fatty acid close to ester bond
Terminal methyl forms steric restriction to " attack " of lipase, there is 6 and 5 double bonds in EPA and DHA molecule respectively, causes complete
The entire chain height of cis-configuration is bent, and strengthens this steric restriction effect, so that lipase is difficult to touch and and glycerol
The ester bond of formation, therefore lipase is weaker to EPA the and DHA acyl group effect on glyceride, however be saturated and monounsaturated rouge
Spatially such steric restriction is not present to enzyme molecule in fat acid, it is easy to be hydrolyzed, obtain the free rouge of DHA and EPA
Fat acid form, saturation or monounsaturated free fatty acid.
Preferably, urea entraing method separation specific steps are as follows: at 60-70 DEG C by weight ratio be 1:1-2 second
Secondary enzymatic hydrolysis obtains free fatty acid and the alcohol saturated solution of urea is mixed, then with the rate of temperature fall of 0.5-1 DEG C/min
It is cooled to 0-5 DEG C, room temperature is raised to after heat preservation crystallization 15-18h, filters, filtrate is extracted, is stood after mixed solution is shaken up
Simultaneously collected organic layer is separated, is evaporated under reduced pressure to get the highly unsaturated fatty acid containing EPA and DHA of concentration is arrived.Free fatty acid
In EPA and DHA be polyunsaturated fatty acid, containing multiple unsaturated bonds, carbochain is in bending, leads to its carbon chain molecules energy
Form certain steric configuration, it is difficult to enter in crystal pipeline, it is more difficult to form urea inclusion, and then can be in the Sino-German great Fu of filtrate
Collection；And the higher fatty acid of saturation degree or monounsaturated fatty acids tend to the urea being crystallized since its saturation degree is higher
Molecule inclusion, and be precipitated in the form of stable inclusion compound, so can be except desaturation or single unsaturated by urea clathrate mode
Fatty acid, thus achieve the purpose that be concentrated EPA and DHA.
Further preferably, stearic acid and lignoceric acid is added when the alcohol saturated solution of free fatty acid and urea mixes.Firmly
The special presence of resin acid and lignoceric acid can be such that the urea to form fine and close quadratic crystal is quickly formed with straight chain fatty acid therein
Smaller and uniform hexahedron crystal, so that fatty acid be saturated or monounsaturated rapidly enters in the pipeline of hexahedron crystal
And urea inclusion is included, and improve saturation or the firmness that is included of monounsaturated fatty acid, it is not easily disconnected from inclusion compound crystalline substance
Body, and then be effectively removed, while can be avoided DHA and EPA and being adsorbed and lost by polar substances urea and fatty acid, it improves
The rate of recovery and purity of DHA and EPA, while urea input amount can be reduced, reduce extraction cost.
Still more preferably, weight of urea 0.23- is added when the alcohol saturated solution of free fatty acid and urea mixes
0.27% stearic acid and the lignoceric acid of weight of urea 0.15-0.20%.
Further preferably, it is 10ml:(1-2 that extraction processing, which is amount ratio with extraction system) g:(2-3) g filtrate, just oneself
Alkane, distillation aqueous systems.
Preferably, the specific steps of esterification are as follows: using the highly unsaturated fatty acid containing EPA and DHA of concentration as substrate,
It puts it into the reaction kettle containing lipase, n-hexane, glycerol and sodium methoxide is added, is carried out in ultrasonic wave magnetic field subcritical
Then reaction product is carried out supercritical extract, rectification process, obtains EPA, DHA by enzymatic reaction.The participation of subcritical fluids,
The back reaction of enzymatic hydrolysis reaction can be carried out, such as be esterified, lactonize, transesterification and the synthesis of peptide, and reducing substrate or production simultaneously
Object is to the inhibition of enzyme, the thermal stability for increasing enzyme, reduction byproduct of reaction, and the addition of ultrasonic wave increases contact of the substrate with enzyme
Area and contact frequency further increase the efficiency of enzymatic reaction, finally obtain the triglyceride type EPA that is naturally occurring and
DHA improves the metabolic adsorption rate of EPA and DHA；Simultaneously in order to reduce the influence to triglyceride type EPA and DHA mass, and it is same
The efficient extraction and purification of Shi Shixian triglyceride type EPA and DHA, using the method for supercritical extract to above-mentioned EPA, DHA
Fatty acid triglycercide is handled, during supercritical extract, since supercritical fluid is in Near The Critical Point, temperature and pressure
Minor change can cause the large change of supercritical fluid densities, it is possible thereby to adjust the solvability to substance, therefore, surpass
The extraction yield of critical extraction is high, and triglyceride type EPA and DHA easy to accomplish and solvent separate in extraction process, and deposit simultaneously
The advantages that organic solvent-free residual, survivable to heat-sensitive substance, it can effectively remove in above-mentioned subcritical enzymatic reaction
Free fatty acid, fat-soluble pigment, volatility and non-volatile aldehydes, the ketone, alcohols stink substances of possible remaining, thus
Achieve the purpose that depickling, decoloration, deodorization.
Further preferably, n-hexane, glycerol, lipase, the polyunsaturated fatty acid containing free EPA, DHA and sodium methoxide
Amount ratio is (8-12) ml:(2-6) g:(0.01-0.05) g:1g:0.02g, the pressure of reaction kettle is 4-8MPa, ultrasonic activation
Magnetic field is 11-13Hz, and reaction temperature is 60-70 DEG C, reaction time 3-5h,.
Further preferably, supercritical extract is divided into two steps of extraction and separation, the condition of extraction are as follows: extracting pressure 20-
30MPa, extraction temperature are 35-40 DEG C, CO2Flow be 4-6L/h；It is divided into two-stage separation, wherein the pressure of level-one separation
Power is 6-10MPa, and temperature is 45-50 DEG C；The pressure of the second-order separation is 4-6MPa, and temperature is 55-60 DEG C.
Compared with the prior art, the advantages of the present invention are as follows: the present invention is using trypsase and lipase from Copepods
DHA and EPA is extracted, the polyunsaturated fatty acid containing EPA and DHA is then separated using urea entraing method, reaction condition is mild, energy
Consume that low, operating cost is low, the rate of recovery and purity is high of EPA and DHA, then by EPA and DHA esterization it is modified under native state
EPA and DHA, EPA the and DHA property made are stablized, can effectively ensure that its nutritional ingredient, be easy to be digested absorption.
Specific embodiment
The present invention program is described further below by embodiment:
Embodiment 1:
A method of it extracting DHA and EPA from Copepods, includes the following steps:
1) Copepods pretreatment of raw material must be homogenized；
2) homogenate is carried out digesting to obtain crude oil liquid for the first time using trypsase, alkali protease and microcrystalline cellulose；
3) crude oil liquid is digested to obtain to the free fatty acid containing EPA, DHA for the second time using lipase；
4) by the free fatty acid containing EPA, DHA using the separation of urea entraing method, the height containing EPA, DHA for extracting to be concentrated
Spend unsaturated fatty acid；
5) extracting to carry out subcritical enzymatic reaction for the polyunsaturated fatty acid containing EPA, DHA of concentration must be esterified
EPA,DHA.The extracting method extracts DHA and EPA using trypsase and lipase from Copepods, then uses urea entraing
Method separates the polyunsaturated fatty acid containing EPA and DHA, and reaction condition is mild, low energy consumption, operating cost is low, time of EPA and DHA
Yield and purity is high, then by EPA and DHA esterization it is modified EPA and DHA under native state, the EPA and DHA made
Matter is stablized, and can effectively ensure that its nutritional ingredient, is easy to be digested absorption.
The specific steps of pretreatment of raw material are as follows: Copepods is sufficiently homogenized with homogenizer, breaks Copepods shell, in release
It is tolerant, it is then that 1:0.7 adds water by feed liquid weight ratio, heats 65min under the conditions of anaerobic, 78 DEG C after mixing, it is standby
With.There is volatile aldehydes, ketone and alcohol, oxidation of coal since the grease in Copepods can decompose generation under aerobic environment
Object, epoxides and acid etc lower-molecular substance lead to fish oil to cause the unstable of acid value, even acid value significantly raised
It is rancid rotten, therefore, for the oxidative rancidity for avoiding polyunsaturated fatty acid, heated under anaerobic, anaerobic item
Part can be inert gas atmosphere, vacuum environment and other common oxygen free conditions, such as nitrogen atmosphere, locate in advance by raw material
Reason, is avoided that generation oxidative rancidity, meanwhile, eliminate the step for carrying out reducing acid value processing as caused by acid value increase
Suddenly.
The specific steps of enzymatic hydrolysis for the first time are as follows: the pH to 8.0 of the homogenate after adjusting pretreatment of raw material, addition trypsase,
The enzyme concentration of alkali protease and microcrystalline cellulose, trypsase and alkali protease is 150U/g and 250U/g, microcrystalline cellulose
The weight ratio of element and alkali protease is 1:2.5, be protected from light, 45 DEG C under the conditions of digest 8h, after enzymatic hydrolysis at 6500rpm from
Heart 10min isolates the crude oil liquid in upper liquid.The step breaks protein and the associations of fat using protease
Bad, to realize the purpose of the separation and Extraction fish oil from raw material, trypsase, alkali protease and microcrystalline cellulose can make albumen
The separation of matter and fat is more abundant, and grease is discharged completely, improves the recovery rate of grease, while can chelate the gold in crude oil liquid
Belong to ion or catalytic metal by aquation, to prevent crude oil liquid oxygen chemical conversion hydroperoxides and new free radical, and can be by hydrogen mistake
Oxide and new free radical are effectively disposed, and are avoided that oxidation reaction occurs, are reduced the color and its oxidation of gained crude oil liquid
Stability, and mainly exist as a triglyceride, the quality of crude oil liquid obtained is improved, for the rate of recovery for improving DHA and EPA
Lay the groundwork, at the same the polypeptide and amino acid of high level in lower layer's enzymolysis liquid can also be developed further into fertilizer, feed or
Seasoning class product improves the utility value of Copepods.
The specific steps of second of enzymatic hydrolysis are as follows: will digest in obtained crude oil liquid and be added by enzyme concentration for 1.5% for the first time
Lipase, be protected from light, 45 DEG C under the conditions of digest 15h to get the free fatty acid containing EPA, DHA.The big multi-connection such as EPA and DHA
In triglycerides on the 2nd of glycerol backbone, the fatty acid of saturation or low-unsaturation-degree is connected on 1 and 3, therefore,
It needs to carry out second to crude oil liquid to digest, and there are carbon-carbon double bond and full cis-configurations in monounsaturated fatty acid molecule, cause
The bending of entire chain, therefore the most end terminal methyl on the cruel molecule of glycerol in unsaturated fatty acid close to ester bond is to lipase
" attack " forms steric restriction, there is 6 and 5 double bonds in EPA and DHA molecule respectively, leads to the entire chain of full cis-configuration
Height is bent, and strengthens this steric restriction effect, so that lipase is difficult to the ester bond for touching and being formed with glycerol, thus it is fatty
Enzyme is weaker to EPA the and DHA acyl group effect on glyceride, however be saturated and monounsaturated fatty acid spatially to enzyme point
Such steric restriction is not present in son, it is easy to be hydrolyzed, obtain the free fatty acid form of DHA and EPA, saturation or it is single
Unsaturated free fatty acid.
The specific steps of urea entraing method separation are as follows: second of enzymatic hydrolysis that weight ratio is 1:1 is dissociated at 60 DEG C
The alcohol saturated solution of fatty acid and urea is mixed, and is then cooled to 0 DEG C with the rate of temperature fall of 0.5 DEG C/min, heat preservation knot
It is raised to room temperature after brilliant 15h, filters, filtrate is extracted, mixed solution is shaken up into rear settle and separate and collected organic layer, decompression
It distills to get the highly unsaturated fatty acid containing EPA and DHA of concentration is arrived.EPA and DHA in free fatty acid are mostly not
Saturated fatty acid, containing multiple unsaturated bonds, carbochain is in bending, causes its carbon chain molecules that can form certain steric configuration,
It is difficult to enter in crystal pipeline, it is more difficult to form urea inclusion, and then can be in the Sino-German big enrichment of filtrate；And the higher rouge of saturation degree
Fat acid or monounsaturated fatty acids tend to the urea molecule being crystallized inclusion, and with stable since its saturation degree is higher
Inclusion compound form is precipitated, so can be except desaturation or monounsaturated fatty acid, to reach dense by urea clathrate mode
The purpose of contracting EPA and DHA.
Wherein, stearic acid and lignoceric acid is added when the alcohol saturated solution of free fatty acid and urea mixes.Stearic acid and
The special presence of lignoceric acid can make to be formed the urea of fine and close quadratic crystal and straight chain fatty acid therein quickly formed it is smaller and
Uniform hexahedron crystal, so that fatty acid be saturated or monounsaturated is rapidly entered in the pipeline of hexahedron crystal and included
Urea inclusion, improve saturation or the firmness that is included of monounsaturated fatty acid, it is not easily disconnected from inclusion compound crystal, in turn
It is effectively removed, while can be avoided DHA and EPA and being adsorbed and lost by polar substances urea and fatty acid, improve DHA and EPA
The rate of recovery and purity, while urea input amount can be reduced, reduce extraction cost.
Wherein, the alcohol saturated solution of free fatty acid and urea mix when be added weight of urea 0.23% stearic acid and
The lignoceric acid of weight of urea 0.15%.
Wherein, extraction processing with extraction system be amount ratio be 10ml:1g:2g filtrate, n-hexane, distillation aqueous systems.
The specific steps of esterification are as follows: using the highly unsaturated fatty acid containing EPA and DHA of concentration as substrate, put it into
In reaction kettle containing lipase, n-hexane, glycerol and sodium methoxide is added, it is anti-that subcritical enzymatic is carried out in ultrasonic wave magnetic field
It answers, reaction product is then subjected to supercritical extract, rectification process, obtains EPA, DHA.The participation of subcritical fluids can carry out
The back reaction of enzymatic hydrolysis reaction, such as be esterified, lactonize, transesterification and the synthesis of peptide, and reducing substrate or product simultaneously to enzyme
Inhibition, increase enzyme thermal stability, reduce byproduct of reaction, and the addition of ultrasonic wave increase substrate and enzyme contact area and
Contact frequency further increases the efficiency of enzymatic reaction, finally obtains the triglyceride type EPA and DHA being naturally occurring, mentions
The metabolic adsorption rate of high EPA and DHA；Simultaneously in order to reduce the influence to triglyceride type EPA and DHA mass, and realize simultaneously
The efficient extraction and purification of triglyceride type EPA and DHA, using the method for supercritical extract to the fatty acid of above-mentioned EPA, DHA
Triglycerides is handled, during supercritical extract, since supercritical fluid is in Near The Critical Point, temperature and pressure it is small
Variation can cause the large change of supercritical fluid densities, it is possible thereby to the solvability to substance is adjusted, therefore, overcritical extraction
The extraction yield that takes is high, and triglyceride type EPA and DHA easy to accomplish and solvent separate in extraction process, and exists simultaneously without having
The advantages that solvent remains, is survivable to heat-sensitive substance, can effectively remove may be residual in above-mentioned subcritical enzymatic reaction
Free fatty acid, fat-soluble pigment, volatility and non-volatile aldehydes, the ketone, alcohols stink substances deposited, to reach de-
Acid, decoloration, the purpose being deodorized.
Wherein, the amount ratio of n-hexane, glycerol, lipase, the polyunsaturated fatty acid containing free EPA, DHA and sodium methoxide
For 8ml:2g:0.01g:1g:0.02g, the pressure of reaction kettle is 4MPa, ultrasonic oscillation magnetic field 11Hz, reaction temperature 60
DEG C, reaction time 3h,.
Wherein, supercritical extract is divided into two steps of extraction and separation, the condition of extraction are as follows: extracting pressure 20MPa, extraction temperature
Degree is 35 DEG C, CO2Flow be 4L/h；It is described to be divided into two-stage separation, wherein the pressure of level-one separation is 6MPa, temperature
It is 45 DEG C；The pressure of the second-order separation is 4MPa, and temperature is 55 DEG C.
Embodiment 2:
A method of it extracting DHA and EPA from Copepods, includes the following steps:
1) Copepods is sufficiently homogenized with homogenizer, breaks Copepods shell, discharge content, then press feed liquid weight ratio
For 1:0.8 plus water, heat 75min under the conditions of anaerobic, 80 DEG C after mixing, it is spare.
2) pH to 8.5 for adjusting the homogenate after pretreatment of raw material, is added trypsase, alkali protease and microcrystalline cellulose
The enzyme concentration of element, trypsase and alkali protease is 200U/g and 300U/g, the weight of microcrystalline cellulose and alkali protease
Than for 1:3, be protected from light, 50 DEG C under the conditions of digest 10h, be centrifuged 12min at 7000rpm after enzymatic hydrolysis, isolate upper liquid
In crude oil liquid.
3) will digest for the first time in obtained crude oil liquid by enzyme concentration be 2.2% be added lipase, be protected from light, 50 DEG C of conditions
Lower enzymatic hydrolysis 17h is to get the free fatty acid containing EPA, DHA.
4) the ethyl alcohol saturation for second of enzymatic hydrolysis that weight ratio is 1:1.5 being obtained free fatty acid and urea at 65 DEG C is molten
Liquid is mixed, wherein the stearic acid of weight of urea 0.25% and the lignoceric acid of weight of urea 0.18% is added when mixing, then
2 DEG C are cooled to the rate of temperature fall of 0.7 DEG C/min, room temperature is raised to after heat preservation crystallization 16h, filters, filtrate is extracted, extract
Processing with extraction system be amount ratio be 10ml:1.5g:2.5g filtrate, n-hexane, distillation aqueous systems, mixed solution is shaken up
Settle and separate and collected organic layer afterwards are evaporated under reduced pressure to get the highly unsaturated fatty acid containing EPA and DHA of concentration is arrived.
5) using the highly unsaturated fatty acid containing EPA and DHA of concentration as substrate, the reaction containing lipase is put it into
In kettle, n-hexane, glycerol and sodium methoxide is added, wherein n-hexane, glycerol, lipase, the how unsaturated containing free EPA, DHA
The amount ratio of fatty acid and sodium methoxide is 10ml:(2-6) g:0.03g:1g:0.02g, subcritical enzyme is carried out in ultrasonic wave magnetic field
Promote reaction, the pressure of reaction kettle is 6MPa, and ultrasonic oscillation magnetic field 12Hz, reaction temperature is 65 DEG C, reaction time 4h, so
Reaction product is subjected to supercritical extract, rectification process afterwards, obtains EPA, DHA；Above-mentioned supercritical extract is divided into extraction and separation
Two steps, the condition of extraction are as follows: extracting pressure 25MPa, extraction temperature are 38 DEG C, CO2Flow be 5L/h；It is divided into two-stage
Separation, wherein the pressure of level-one separation is 8MPa, and temperature is 48 DEG C；The pressure of the second-order separation is 5MPa, and temperature is 58 DEG C.DHA
Overall recovery with EPA is 94.7%.
Embodiment 3:
A method of it extracting DHA and EPA from Copepods, includes the following steps:
1) Copepods is sufficiently homogenized with homogenizer, breaks Copepods shell, discharge content, then press feed liquid weight ratio
For 1:0.9 plus water, heat 85min under the conditions of anaerobic, 84 DEG C after mixing, it is spare.
2) pH to 9.0 for adjusting the homogenate after pretreatment of raw material, is added trypsase, alkali protease and microcrystalline cellulose
The enzyme concentration of element, trypsase and alkali protease is 250U/g and 350U/g, the weight of microcrystalline cellulose and alkali protease
Than for 1:3.4, be protected from light, 55 DEG C under the conditions of digest 12h, be centrifuged 15min at 7500rpm after enzymatic hydrolysis, isolate upper layer
Crude oil liquid in liquid.
3) will digest for the first time in obtained crude oil liquid by enzyme concentration be 3.0% be added lipase, be protected from light, 55 DEG C of conditions
Lower enzymatic hydrolysis 19h is to get the free fatty acid containing EPA, DHA.
4) second of enzymatic hydrolysis that weight ratio is 1:2 is obtained into the alcohol saturated solution of free fatty acid and urea at 70 DEG C
Mixed, wherein when mixing be added weight of urea 0.27% stearic acid and weight of urea 0.20% lignoceric acid, then with
The rate of temperature fall of 1 DEG C/min is cooled to 5 DEG C, is raised to room temperature after heat preservation crystallization 18h, filters, filtrate is extracted, extraction processing
With extraction system be amount ratio be 10ml:2g:3g filtrate, n-hexane, distillation aqueous systems, after mixed solution is shaken up stand point
From simultaneously collected organic layer, it is evaporated under reduced pressure to get the highly unsaturated fatty acid containing EPA and DHA of concentration is arrived.
5) using the highly unsaturated fatty acid containing EPA and DHA of concentration as substrate, the reaction containing lipase is put it into
In kettle, n-hexane, glycerol and sodium methoxide is added, wherein n-hexane, glycerol, lipase, the how unsaturated containing free EPA, DHA
The amount ratio of fatty acid and sodium methoxide is 12ml:6g:0.05g:1g:0.02g, and it is anti-that subcritical enzymatic is carried out in ultrasonic wave magnetic field
It answers, the pressure of reaction kettle is 8MPa, and ultrasonic oscillation magnetic field 13Hz, reaction temperature is 70 DEG C, reaction time 5h, then will
Reaction product carries out supercritical extract, rectification process, obtains EPA, DHA；Above-mentioned supercritical extract is divided into two steps of extraction and separation,
The condition of the extraction are as follows: extracting pressure 30MPa, extraction temperature are 40 DEG C, CO2Flow be 6L/h；It is described to be divided into
Two-stage separation, wherein the pressure of level-one separation is 10MPa, and temperature is 50 DEG C；The pressure of the second-order separation is 6MPa, temperature 60
℃。
Comparative example 1:
A method of it extracting DHA and EPA from Copepods, includes the following steps:
The specific steps of enzymatic hydrolysis for the first time are as follows: the pH to 8.5 of the homogenate after adjusting pretreatment of raw material, addition trypsase,
The enzyme concentration of alkali protease, trypsase and alkali protease be 200U/g and 300U/g, be protected from light, 50 DEG C under the conditions of digest
10h is centrifuged 12min at 7000rpm after enzymatic hydrolysis, isolates the crude oil liquid in upper liquid.Remaining is consistent with embodiment 2.
The PCR reaction product that 1 purification and recovery of comparative example obtains is well below embodiment 2.The overall recovery of DHA and EPA is 92.7%.
This illustrates that trypsase, alkali protease and microcrystalline cellulose can improve the quality of crude oil liquid obtained, to improve DHA and EPA
The rate of recovery lay the groundwork.
Comparative example 2:
A method of it extracting DHA and EPA from Copepods, includes the following steps:
The specific steps of urea entraing method separation are as follows: swum second of enzymatic hydrolysis that weight ratio is 1:2 at 70 DEG C
Alcohol saturated solution from fatty acid and urea is mixed, and is then cooled to 5 DEG C with the rate of temperature fall of 1 DEG C/min, heat preservation knot
It is raised to room temperature after brilliant 18h, filters, filtrate is extracted, it is 10ml:2g:3g's that extraction processing, which is amount ratio with extraction system,
Mixed solution is shaken up rear settle and separate and collected organic layer by filtrate, n-hexane, distillation aqueous systems, and vacuum distillation is dense to get arriving
The highly unsaturated fatty acid containing EPA and DHA of contracting.Remaining is consistent with embodiment 2.The overall recovery of DHA and EPA is
91.5%.This illustrates that the special presence of stearic acid and lignoceric acid can improve the rate of recovery of DHA and EPA.
Comparative example 3:
A method of it extracting DHA and EPA from Copepods, includes the following steps:
The specific steps of esterification are as follows: using the highly unsaturated fatty acid containing EPA and DHA of concentration as substrate, put it into
In reaction kettle containing lipase, be added n-hexane, glycerol, wherein n-hexane, glycerol, lipase, containing free EPA, DHA
The amount ratio of polyunsaturated fatty acid is 12ml:6g:0.05g:1g, subcritical enzymatic reaction is carried out in ultrasonic wave magnetic field, instead
The pressure for answering kettle is 8MPa, and ultrasonic oscillation magnetic field 13Hz, reaction temperature is 70 DEG C, reaction time 5h, then will reaction
Product carries out supercritical extract, rectification process, obtains EPA, DHA；Above-mentioned supercritical extract is divided into two steps of extraction and separation, described
The condition of extraction are as follows: extracting pressure 30MPa, extraction temperature are 40 DEG C, CO2Flow be 6L/h；It is described to be divided into two-stage
Separation, wherein the pressure of level-one separation is 10MPa, and temperature is 50 DEG C；The pressure of the second-order separation is 6MPa, and temperature is 60 DEG C.Its
It is remaining consistent with embodiment 2.The overall recovery of DHA and EPA is 90.9%.This illustrate the addition of sodium methoxide so that enzymatic reaction effect
Rate improves.
Routine operation in operation of the present invention step is well known to those skilled in the art, herein without repeating.
Technical solution of the present invention is described in detail in embodiment described above, it should be understood that the above is only
For specific embodiments of the present invention, it is not intended to restrict the invention, all any modifications made in spirit of the invention,
Supplement or similar fashion substitution etc., should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of method for extracting DHA and EPA from Copepods, characterized by the following steps:
1) Copepods pretreatment of raw material must be homogenized；
2) homogenate is carried out digesting to obtain crude oil liquid for the first time using trypsase, alkali protease and microcrystalline cellulose；
3) crude oil liquid is digested to obtain to the free fatty acid containing EPA, DHA for the second time using lipase；
4) free fatty acid containing EPA, DHA is used into the separation of urea entraing method, the height containing EPA, DHA for extracting to be concentrated not
Saturated fatty acid；
5) the polyunsaturated fatty acid extraction extraction containing EPA, DHA of concentration is subjected to subcritical enzymatic reaction, then produces reaction
Object carries out supercritical extract, rectification process must be esterified EPA, DHA.
2. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: the raw material
Pretreated specific steps are as follows: Copepods is sufficiently homogenized, is then that 1:0.7-0.9 adds water by feed liquid weight ratio, is uniformly mixed
Heat 65-85min under the conditions of anaerobic, 78-84 DEG C afterwards, it is spare.
3. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: described first
The specific steps of secondary enzymatic hydrolysis are as follows: trypsase, alkalinity is added in the pH to 8.0-9.0 of the homogenate after adjusting the pretreatment of raw material
Protease and microcrystalline cellulose, be protected from light, 45-55 DEG C under the conditions of digest 8-12h, be centrifuged after enzymatic hydrolysis, isolate upper liquid
In crude oil liquid.
4. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: the pancreas egg
The enzyme concentration of white enzyme and alkali protease is 150-250U/g and 250-350U/g, the weight of microcrystalline cellulose and alkali protease
Than for 1:2.5-3.4.
5. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: described second
The specific steps of secondary enzymatic hydrolysis are as follows: it will digest for the first time in obtained crude oil liquid and lipase be added for 1.5-3.0% by enzyme concentration,
It is protected from light, digests 15-19h under the conditions of 45-55 DEG C to get the free fatty acid containing EPA, DHA.
6. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: the urea
The specific steps of investment separation are as follows: at 60-70 DEG C by weight ratio be second of 1:1-2 enzymatic hydrolysis obtain free fatty acid and
The alcohol saturated solution of urea is mixed, and is cooled to 0-5 DEG C, is raised to room temperature after heat preservation crystallization 15-18h, is filtered, by filtrate into
Row extraction, collected organic layer are evaporated under reduced pressure to get the highly unsaturated fatty acid containing EPA and DHA of concentration is arrived.
7. a kind of method for extracting DHA and EPA from Copepods according to claim 6, it is characterised in that: described free
Stearic acid and lignoceric acid are added when the alcohol saturated solution of fatty acid and urea mixes.
8. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: the extraction
It is 10ml:(1-2 that processing, which is amount ratio with extraction system) g:(2-3) filtrate of g, n-hexane, distillation aqueous systems.
9. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: the enzymatic
Be additionally added in reaction and n-hexane, glycerol and sodium methoxide be added, the n-hexane, glycerol, lipase, containing the more of free EPA, DHA
The amount ratio of unsaturated fatty acid and sodium methoxide is (8-12) ml:(2-6) g:(0.01-0.05) g:1g:0.02g, the reaction
The pressure of kettle is 4-8MPa, and ultrasonic oscillation magnetic field 11-13Hz, reaction temperature is 60-70 DEG C, reaction time 3-5h.
10. a kind of method for extracting DHA and EPA from Copepods according to claim 1, it is characterised in that: described super
Critical extraction is divided into two steps of extraction and separation, the condition of the extraction are as follows: extracting pressure 20-30MPa, extraction temperature 35-
40 DEG C, CO2Flow be 4-6L/h；It is described to be divided into two-stage separation, wherein the pressure of level-one separation is 6-10MPa, temperature
It is 45-50 DEG C；The pressure of the second-order separation is 4-6MPa, and temperature is 55-60 DEG C.
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| CN110904166A (en) * | 2019-12-11 | 2020-03-24 | 付俊 | Method for extracting brain gold from giant salamander |
| CN111560405A (en) * | 2020-05-18 | 2020-08-21 | 中国海洋大学 | Preparation method and application of EPA/ARA type plasmalogen |
| CN113349308A (en) * | 2021-05-10 | 2021-09-07 | 广州清科生物技术有限公司 | Composite zymolyte for pet food and preparation process thereof |
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