CN108265090A - The preparation method of antarctic krill oil substitute - Google Patents
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Abstract
The invention discloses a kind of preparation methods of antarctic krill oil substitute.The present invention provides a kind of method for preparing the fat or oil composition containing phosphatide type DHA and phosphatide type EPA and the fat or oil compositions prepared according to this method.Specifically, the present invention is accurately controlled by the ratio to DHA in reaction raw materials and EPA, the phosphatide type DHA contained the and phosphatide type EPA fat or oil compositions almost the same with natural antarctic krill oil is made.
Description
Technical field
The invention belongs to the field of lipid is prepared using living things catalysis, and in particular to using biological enzyme formulation as catalyst,
Using soybean lecithin, EPA or its esterification derivative and DHA or its esterification derivative as raw material, antarctic krill oil substitute is prepared
Method.
Background technology
Polyunsaturated fatty acid (PUFA) refers to that carbon atom number is no less than 18 and one kind fat containing more than two double bonds
Acid；Wherein, first double bond appears in the PUFA at the 3rd, carbochain methyl end and is known as n-3 polyunsaturated fatty acids.The more insatiable hungers of n-3
Include docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) with the representative instance of aliphatic acid.A large amount of pharmacology and animal are real
Verify bright, DHA is required for retina normal development and the enforcement of nervous system normal function.In brain and retina, DHA
About 20% and about 35% of fatty acid total amount at this is accounted for respectively, and is mainly existed with phospholipid form.Statistics indicate that DHA is from gestation
Start within 26-40 weeks to accumulate in the nerve cell of fetal central nervous system；Compared with gestation 26 weeks, the last 3 months tires of gestation
DHA content increases three to five times in youngster's brain and cerebellum.The intake for improving cradle DHA is obviously promoted big intracerebral nerve
The growth of cell and the formation of dendron, therefore help to improve ability of learning and memory.Moreover, it is old to also help prevention by DHA
The generation of dementia.Research shows that compared with healthy elderly, the DHA content of old dementia patients cerebral hippocampus cell reduces
Nearly 10%；Giving DHA then contributes to slowing down for illness.In addition, fatty acid chain length and degree of unsaturation and the photoreception in retina
The Liquidity of film, mobility, refrangibility, permeability are closely related.When DHA supplies are insufficient, the photoperceptivity and eyesight of eyes are all
It will appear apparent decline.On the other hand, EPA is as a kind of polyunsaturated fatty acid chemical messenger, in immune and inflammatory reaction
In play an important role.Specifically, EPA can be sent out by regulating and controlling the generation of phosphatidyl glycerol (PG) at blood platelet and vascular wall
Wave anti thrombotic action；It is also reduced by Reverse transcriptase via the PGE2 that arachidonic acid pathway synthesizes, so as to mitigate urgency
Property inflammatory reaction.Animal experiments show that EPA can significantly reduce blood triglyceride levels.In addition, DHA's and EPA gives jointly
Treatment for children ADHD, school-ager be aggressive and the control of act of violence and major depressive disorder, anxiety disorder and frightened
Probably certain effect is respectively provided in terms of the improvement of disease.Major nutrition mechanism of the world, which all gives the intake of DHA and EPA, to be built
View.For example, adult EPA and the DHA intake of FAO (Food and Agriculture Organization of the United Nation) and world health organisation recommendations are 250mg/ days；Gestation
EPA the and DHA intakes of phase and nursing period women are 300mg/ days.European Food Safety Authority also suggests that adult is daily ingestion of
250mgEPA and DHA.
The above-mentioned physiological function of DHA and EPA is that global researcher and consumer generally acknowledge.However, prepare commercialized DHA
Or there are still many problems for EPA dietary supplements.Particularly, commercialized DHA and EPA is mainly in the form of ethyl ester or triglycerides
In the presence of in terms of absorption efficiency and oxidation stability still undesirably.Mouse experiment shows DHA the or EPA phases with phospholipid form
Than brain, liver and kidney and other organs, which absorb ethyl ester or the rate of the DHA or EPA of triglycerides form, to be reduced more than twice.
In addition, triglycerides generally goes through as energy source and is directly entered energy metabolic pathways after digesting and assimilating in vivo for generating
ATP is transported to adipocyte as energy reserve.Therefore, the DHA or EPA of triglycerides form are merely used as fuel,
Its functionality advantage is not played.In contrast to this, the polyunsaturated fatty acid of phospholipid form is naturally occurring in internal membrane structure
In, the DHA or EPA of phospholipid form are more easy to play its bioactivity.
Antarctic krill oil is the new raw-food material of Ministry of Public Health's approval, is that unique one kind of current commercialization naturally contains phosphatide
The product of type n-3 polyunsaturated fatty acids is maximally efficient DHA and EPA dietary supplements.However, krill there is only
In antarctic waters, it is not easy to obtain in China.On the other hand, the antarctic krill oil as krill extraction has potential sensitization.This
Invention is dedicated to DHA and EPA is accessed soybean lecithin using biocatalysis technology, so as to produce phosphatide type DHA and EPA content
With the identical substitute products of antarctic krill oil.The substitute products are as the effect of DHA and EPA dietary supplements and South Pole phosphorus
Shrimp sauce is consistent；And due to being free of other sensibiligens, it is for a wider population.
As shown by bibliography 1-7, art has developed a variety of methods, by ester exchange reaction that n-3 is more
Unrighted acid accesses phosphatide.
[bibliography 1] Sun Zhaomin etc., enzyme process prepares the technique of n-3 polyunsaturated fatty acid type phosphatide,《Chinese oil》.
[bibliography 2] Xiang Li et al., Production of Structured Phosphatidylcholine
with High Content of DHA/EPA by Immobilized Phospholipase A1-Catalyzed
Transesterification, Int.J.Mol.Sci..
[bibliography 3] In-Hwan Kim etc., Synthesis of Structured Phosphatidylcholine
Containing n-3 PUFA Residues via Acidolysis Mediated by Immobilized
Phospholipase A1, J.Am.Oil.Chem.Soc..
[bibliography 4] In-Hwan Kim etc., Phospholipase A1-catalyzed synthesis of
Phospholipids enriched in n-3 polyunsaturated fatty acid residues, Enzyme and
Microbial Technology。
[bibliography 5] Hugo S.Garcia etc., Enrichment of lecithin with n-3 fatty
Acids by acidolysis using immobilized phospholipase A1, GRASAS Y ACEITES.
[bibliography 6] TingTing Zhao, Immobilized phospholipase A1-catalyzed
Modification of phosphatidylcholine with n3 polyunsaturated fatty acid, Food
Chemistry。
[bibliography 7] Lifeng Peng etc., Production of structured phospholipids by
lipase-catalyzed acidolysis:Optimization using response surface methodology,
Enzyme and Microbial Technology。
However, the method for above-mentioned document report cannot prepare phosphatide type DHA and EPA content and the complete phase of antarctic krill oil
Same product.Specifically, bibliography 1-7 is directly made with the Purified fish oil containing polyunsaturated fatty acid/aliphatic ester
For raw material.It is known in the field to be, due to the space structure difference of DHA and EPA, in the ester exchange reaction of biological enzyme
In, the access efficiency difference of the two is notable.DHA and EPA ratios have been fixed in Purified fish oil raw material, can not be by the later stage it is artificial
Its ratio is adjusted in allotment.Therefore, the technique directly prepared using natural fish oil can not realize EPA and DHA compositions and south
Pole krill oil is close.
And then bibliography 1-6 is using the exchange reaction of PLA1 enzymatics phosphatide and DHA and EPA.However, commercialization
PLA1 enzymes are liquid enzyme, there is no immobilization product at present, need to implement complicated immobilization step when in use.Therefore, it is above-mentioned
Process industry practicability is poor.
Again, bibliography 1 and 2 is carried out using ethyl ester type n-3 polyunsaturated fatty acids with phosphatide under solvent-free conditions
Ester exchange reaction, however, the limitation of the intersolubility and reaction system homogeneity due to fatty-acid ethyl ester and phosphatide, only in aliphatic acid
The weight ratio of ethyl ester and phosphatide is up to 6:1 (weight ratio nearly 14:1) reaction can be realized when more than, best total access rate is also only
For 25wt% or so.
In addition, bibliography 3-7 carries out ester exchange reaction using sequestered DHA and EPA as raw material, with phosphatide.It is such to set
The homogeneity of intersolubility and system for improving DHA and EPA and phosphatide is put, therefore greatly reduces the dosage of DHA and EPA.
It is well known, however, that compared to esters substrate, the service life that immobilised enzymes will be greatly lowered in sequestered substrate, so as to
Improve processing cost.In addition, Stine et al. provides phosphatide type or triglyceride type DHA respectively to two groups of subjects, work as phosphatide
When type DHA dosages are the 62.8% of triglyceride type DHA dosage, subject's blood can reach equal DHA and EPA refers to
Number.Hansen's et al. clinical experiments have proved that phosphatide type DHA has higher absorption efficiency than ethyl ester type DHA.With regard to this point
Speech, directly takes, above-mentioned technique is both needed to carry out further purification step to remove since sequestered aliphatic acid is not suitable for human body
A large amount of free fatty, improves manufacturing cost again in product.
At present, there has been no can accurately prepare to have the phosphatide type DHA/EPA content close with antarctic krill oil for this field
Product method.
Invention content
On the one hand, the present invention provides a kind of sides for preparing the fat or oil composition containing phosphatide type DHA and phosphatide type EPA
Method, described method includes following steps：
(1) at room temperature, DHA or its ester derivative with EPA or its ester derivative are mixed, obtains grease and mix
Object A is closed,
Wherein, the content of DHA derives not less than 75wt%, the EPA or its esters in the DHA or its ester derivative
The content of EPA is not less than 75wt%, the DHA or its ester derivative and the addition of EPA or its ester derivative in object
For：So that the weight ratio of DHA and EPA is (30-70) in rich mixture A:(70-30)；
(2) the rich mixture A for obtaining soybean lecithin and step (1) is according to (10-35):The weight ratio of (90-65)
It is mixed, obtains rich mixture B, wherein, the phosphorus level in soya lecithin fat content added in is not less than 75wt%；
(3) rich mixture that step (2) obtains is preheated to 40 DEG C -70 DEG C, adds in distilled water and mixed, it is described
The addition of distilled water is the 0-6wt% of enzyme preparation addition in step (4)；
(4) lipase of immobilization or phosphatide enzyme preparation is added in the reaction mixture obtained to step (3), 40
It is reacted at a temperature of DEG C -70 DEG C, obtains fat or oil composition C；
Wherein, the content of phosphatide type DHA and phosphatide type EPA be respectively the fat or oil composition C 9.0-15.0wt% and
18.0-25.0wt%.
On the other hand, the present invention provides contain phosphatide type DHA and phosphatide made from the method according to first aspect
The fat or oil composition of type EPA.
Specifically, the present invention is achieved through the following technical solutions：
1. a kind of method for preparing the fat or oil composition containing phosphatide type DHA and phosphatide type EPA, the method includes as follows
Step：
(1) at room temperature, DHA or its ester derivative with EPA or its ester derivative are mixed, obtains grease and mix
Object A is closed,
Wherein, the content of DHA derives not less than 75wt%, the EPA or its esters in the DHA or its ester derivative
The content of EPA is not less than 75wt%, the DHA or its ester derivative and the addition of EPA or its ester derivative in object
For：So that the weight ratio of DHA and EPA is (30-70) in rich mixture A:(70-30)；
(2) the rich mixture A for obtaining soybean lecithin and step (1) is according to (10-35):The weight ratio of (90-65)
It is mixed, obtains rich mixture B, wherein, the phosphorus level in soya lecithin fat content added in is not less than 75wt%；
(3) rich mixture that step (2) obtains is preheated to 40 DEG C -70 DEG C, adds in distilled water and mixed, it is described
The addition of distilled water is the 0-6wt% of enzyme preparation addition in step (4)；
(4) lipase of immobilization or phosphatide enzyme preparation is added in the reaction mixture obtained to step (3), 40
It is reacted at a temperature of DEG C -70 DEG C, obtains fat or oil composition C；
Wherein, the content of phosphatide type DHA and phosphatide type EPA be respectively the fat or oil composition C 9.0-15.0wt% and
18.0-25.0wt%.
2. the method as described in paragraph 1, wherein, in step (1), the DHA or its ester derivative come from fish oil, sea
The arbitrary combination of any one of algae oil, microbial grease or above-mentioned grease；The EPA or its ester derivative come from fish
The arbitrary combination of any one of oil, algal oil, microbial grease or above-mentioned grease.
3. the method as described in paragraph 1 or 2, wherein, in step (1), the DHA or its ester derivative are selected from DHA
Methyl esters type derivative, ethyl ester type derivative, glycerine ester type derivative or sequestered DHA or above-mentioned DHA or its esters derive
The arbitrary combination of object；The EPA or its ester derivative are selected from methyl esters type derivative, ethyl ester type derivative, the glyceride of EPA
The arbitrary combination of type derivative or sequestered EPA or above-mentioned EPA or its ester derivative；Preferably, the DHA or its ester
Analog derivative is DHA ethyl ester type derivative；Preferably, the EPA or its ester derivative are EPA ethyl ester type derivative.
5. the method as described in any one of paragraph 1-4, wherein, in step (1), the DHA or its ester derivative with
And the addition of EPA or its ester derivative is：So that the weight ratio of DHA and EPA is (35-45) in rich mixture A:(65-
55)。
6. the method as described in any one of paragraph 1-5, wherein, in step (2), in the soybean lecithin, phosphatide contains
Amount is not less than 85wt%.
7. the method as described in any one of paragraph 1-6, wherein, in step (2), soybean lecithin and step (1) are obtained
The rich mixture A obtained is according to (20-30):The weight ratio of (80-70) is mixed.
8. the method as described in any one of paragraph 1-7, wherein, in step (2), it is described be blended under solvent-free system into
Row.
9. the method as described in any one of paragraph 1-7, wherein, in step (2), the mixing in organic solvent into
Row, the organic solvent are selected from any one of group being made of n-hexane, isohexane, acetone or arbitrary combination；It is preferred that
Ground, the organic solvent are n-hexane.
10. the method as described in paragraph 9, wherein, the addition of the n-hexane is：Per 100mg phosphatide addition 1ml-
1.5ml n-hexane.
11. the method as described in any one of paragraph 1-10, wherein, in step (3), will preheating described in step 45 DEG C-
65℃。
12. the method as described in any one of paragraph 1-11, wherein, in step (3), the addition of the distilled water is step
Suddenly in (4) enzyme preparation addition 1.5-3.5wt%.
13. the method as described in any one of paragraph 1-12, wherein, in step (4), the lipase or phosphorus of the immobilization
Lipase preparations are the lipase preparation of immobilization.
14. the method as described in paragraph 13, wherein, the lipase preparation of the immobilization is derived from selected from following fungi
It is one or more：Rhizomucor miehei dredges the thermophilic hyphomycete of cotton like and aspergillus niger.
15. the method as described in paragraph 14, wherein, the lipase preparation of the immobilization is rhizomucor miehei RM IM fat
Fat enzyme preparation dredges the thermophilic hyphomycete TL IM lipase preparations of cotton like or aspergillus niger SP435 preparations.
16. the method as described in any one of paragraph 1-15, wherein, in step (4), the lipase or phosphorus of the immobilization
The addition of lipase preparations is the 5wt%-35wt%, preferably 10wt%-30wt% of the rich mixture B.
17. the method as described in any one of paragraph 1-16, wherein, in step (4), the reaction temperature is 45 DEG C -65
℃。
18. the method as described in any one of paragraph 1-17, wherein, in step (4), the reaction carries out 1-48 hours,
It is preferred that 8-24 hours.
19. the grease containing phosphatide type DHA and phosphatide type EPA made from the method according to any one of paragraph 1-18
Composition, wherein, the content of phosphatide type DHA and phosphatide type EPA be respectively the fat or oil composition C 9.0-15.0wt% and
18.0-25.0wt%.
" room temperature " of the present invention refers to temperature range of the environment temperature at 16-26 DEG C.
Advantageous effect
Since fungal lipase and phosphatidase are to the selectivity of substrate, the access difficulty difference of EPA and DHA are very big.This
There has been no the reports of the content for the preparing phosphatide type DHA and EPA fat or oil composition similar with antarctic krill oil in field.The present invention
It is put forward for the first time, is accurately controlled by the ratio to DHA in reaction raw materials and EPA, the phosphatide type DHA and phosphatide contained is made
Fat or oil composition almost the same with natural antarctic krill oil type EPA.In the product of the present invention, phosphatide type DHA and phosphatide
The content of type EPA is respectively the 9.0-15.0wt% and 18.0-25.0wt% of the fat or oil composition.Such ratio contributes to
DHA and EPA is fully absorbed and is utilized in vivo.
As described above, for human body, compared with triglyceride type and ethyl ester type n-3 polyunsaturated fatty acids, phosphatide type
N-3 polyunsaturated fatty acids have notable higher absorption rate, therefore are more suitable for having and promote brain development, improve angiocarpy
The consumer of health demand takes.It on the other hand, can as dietary supplements using the product of the present invention due to absorption rate height
Lipid intake total amount is reduced while the bioactivity being equal with the prior art is realized, more meets health idea.
In addition, the present invention especially has chosen commercialized immobilised enzymes as catalyst, the repeatability of reaction is improved
And commercial viability, it can realize prepared by the batch of antarctic krill oil substitute.
In a preferred embodiment, in rich mixture B add in n-hexane (《GB2760—2014》Middle processing helps
Agent), it increases soybean lecithin and the esters containing EPA or DHA is miscible, realize being greatly lowered for DHA and EPA dosages.At it
In its preferred embodiment, using the ethyl ester type derivative of DHA or EPA as raw material, yield is higher and need not be tied in reaction
Free fatty is detached after beam.However, lipase preparation catalysis EPA or the efficiency of DHA esterization reaction are by EPA or DHA itself
There are the influences of the steric hindrance caused by multiple double bonds.Particularly as EPA or DHA for using ethyl ester type, the steric hindrance
Influence it is more obvious, so as to cause the reduction of access rate.It was found by the inventors of the present invention that the addition of n-hexane causes reactant
The viscosity of system reduces, therefore improves the mobility of reactant, and ethyl ester type substrate is caused to be more easy to carry out with reacting for lipase, from
And reduce the reaction time.Therefore, n-hexane is added in system while ethyl ester type EPA or DHA is used, not only saved
Raw material reduces the reaction time, also improves yield, has higher commercial viability.
Specific embodiment
It hereafter will be apparent from the present invention.
Terms used herein " phosphatide type DHA " or " phosphatide type EPA " refer to that DHA or EPA are accessed to phosphoglycerol base 1
Position or the phosphatide of 2.Known in the field to be, phosphatide is a kind of lipid containing phosphate, is generally had hydrophilic
Head and hydrophobic tail portion；The hydrophilic head by phosphate and the substituent group being connected with phosphate (such as containing ammonia alkali or
Alcohols) it forms, the hydrophobic tail is made of fatty acid chain.The hydrophilic head of phosphatide type DHA and phosphatide type EPA can be phosphorus
Resin acid (PA), phosphatidyl choline (PC), phosphatidyl-ethanolamine (PE), phosphatidyl glycerol (PG), phosphatidylinositols (PI) etc..
In a first aspect, the present invention relates to the methods for preparing the fat or oil composition containing phosphatide type DHA and phosphatide type EPA.
In fat or oil composition prepared according to the methods of the invention, the content of phosphatide type DHA and phosphatide type EPA are respectively the grease combination
The 9.0-15.0wt% and 18.0-25.0wt% of produce product.As shown in embodiment, phosphatide type DHA in antarctic krill oil
Content with phosphatide type EPA is respectively about 13.9wt% and 22.0wt%.Therefore, the product that prepared by the method for the present invention can be advantageously
As antarctic krill oil substitute, for supplementing DHA and EPA.
In some embodiments, DHA used in the step of the method for the present invention (1) or its ester derivative and EPA
Or its ester derivative can be any source, such as from any one of fish oil, algal oil, microbial grease or above-mentioned oil
The arbitrary combination of fat.The DHA or its ester derivative can be the methyl esters type derivative, ethyl ester type derivative, glycerine ester type of DHA
The arbitrary combination of derivative either sequestered DHA or above-mentioned DHA or its ester derivative.The EPA or its esters derive
Object can be selected from methyl esters type derivative, ethyl ester type derivative, glycerine ester type derivative or the sequestered EPA, Huo Zheshang of EPA
State EPA or the arbitrary combination of its ester derivative.Preferably, the DHA or its ester derivative are DHA ethyl ester type derivative.
Preferably, the EPA or its ester derivative are EPA ethyl ester type derivative.In the DHA or its ester derivative, DHA's contains
Amount is not less than 75wt%, and in the EPA or its ester derivative, the content of EPA is not less than 75wt%.
In the step (1) of the present invention, need accurately to control DHA the and EPA ratios in rich mixture A, from
And so that phosphatide type DHA and phosphatide type EPA content are approached with antarctic krill oil in the product obtained.Preferably, the DHA or its
The addition of ester derivative and EPA or its ester derivative is：So that the weight ratio of DHA and EPA is in rich mixture A
(35-45):(65-55)。
Soybean lecithin is the raw material of industry commonly used in the art, mainly contains phosphatidic acid, phosphatidyl choline (also referred to as lecithin
Fat), phosphatidyl-ethanolamine and phosphatidylinositols, wherein phosphatidylcholine content highest.The step of the method for the present invention (2), is used
Phosphorus level in soya lecithin fat content be preferably not less than 75wt%, more desirably not less than 85wt%.Soybean lecithin and step (1)
The mixed proportion of the rich mixture A of acquisition is (10-35):The effect of the present invention can be realized when (90-65), however, according to
(20-30):The weight ratio of (80-70) mixes more preferably the two.
The step (1) and being blended under room temperature (being typically 16-26 DEG C) for step (2) of the present invention carries out.The mixing
It is carried out under conditions of solvent-free system or there are organic solvent.In order to improve dissolving each other for phosphatide and the esters containing DHA/EPA
Property, the mixing of step (2) is carried out preferably under conditions of there are organic solvent.The organic solvent is selected from by n-hexane, different
Any one of group that hexane, acetone are formed or arbitrary combination；Preferably, the organic solvent is n-hexane.It is described just oneself
The addition of alkane should be determined according to the content of phosphatide in reaction mixture.Preferably, the addition of the n-hexane is：Often
100mg phosphatide adds 1ml-1.5ml n-hexanes.
The preheating temperature of rich mixture B is 40 DEG C -70 DEG C, preferably 45 DEG C -65 DEG C in the method for the present invention step (3).Institute
The amount of the distilled water of addition needs accurate control, the 0-6wt% of enzyme preparation addition preferably in step (4), more preferably
1.5-3.5wt%.
In the step of the method for the present invention (4), the lipase or phosphatide enzyme preparation of the immobilization are the lipase of immobilization
The lipase preparation of preparation, preferably immobilization.Preferably, the lipase preparation of the immobilization is derived from selected from following fungi
It is one or more：Rhizomucor miehei (Rhizomucor miehei) dredges the thermophilic hyphomycete (Thermomyces of cotton like
) and aspergillus niger (Aspergillus niger) lanuginosus.Preferably, the lipase preparation of the immobilization is rice black root
Mucor RM IM lipase preparations dredge the thermophilic hyphomycete TL IM lipase preparations of cotton like or aspergillus niger SP435 preparations.In some realities
It applies in mode, the lipase of the immobilization or the 5wt%- that the addition of phosphatide enzyme preparation is the rich mixture B
35wt%, preferably 10wt%-30wt%.Reaction temperature is controlled at 40 DEG C -70 DEG C, preferably 45 DEG C -65 DEG C.The reaction carries out 1-
48 hours, preferably 8-24 hours.
In second aspect, the present invention relates to contain phosphatide type DHA and phosphatide made from the method according to first aspect
The fat or oil composition of type EPA, wherein, the content of phosphatide type DHA and phosphatide type EPA are respectively the 9.0- of the fat or oil composition C
15.0wt% and 18.0-25.0wt%.
Description of the drawings
Fig. 1 is the gas chromatogram analyzed using chromatography the composition of all fatty acids in grease standard sample.
Fig. 2 is the gas chromatogram for the fat or oil composition 1 that the embodiment of the present invention 1 obtains.
Fig. 3 is the gas chromatogram for the fat or oil composition 1 that comparative example 1 of the present invention obtains.
Embodiment
The present invention is described in further detail by the following examples.These embodiments are merely illustrative, and
It is limiting the scope of the present invention that should not be construed.Every technical solution realized based on the above of the present invention and its
Deformation is within the scope of the present invention.
The phosphatide used in embodiment and comparative example is purchased from Sigma-Aldrich companies (production number 1001900076), should
The content of phosphorus level in soya lecithin fat is 86wt%.DHA ester analog derivative and EPA ester analog derivative respectively purchased from BASF (in
State) Co., Ltd's (concentration DHA (ethyl ester type), 50382353) and Wuxi City it is fast up to marine organisms Products Co., Ltd (concentration EPA
(ethyl ester type, EPE150818).Wherein, the content of DHA is 79.7wt% in DHA ester analog derivative, EPA in EPA ester analog derivative
Content be 76.2wt%.Antarctic krill oil is purchased from Aker companies of Norway (0995250100).The RM IM lipase of immobilization,
It is raw that PLA1 lipase (liquid), TL IM lipase (immobilization) and SP435 lipase (immobilization) are purchased from Novi's letter (China)
Object Technology Co., Ltd. (production number is respectively CHE-20, LYN05060, LA331342, LC200266).N-hexane is pure to analyze,
Purchased from Chinese medicines group.
In embodiment and comparative example, according to the gas chromatography described in standard GB/T 28404-2012, to various kinds
The distribution of aliphatic acid and content are analyzed in product, the model Agilent 1890B of used gas chromatograph.
Specifically, to grease standard sample, (fatty acid methyl ester mixes mark, 37 kinds of C4-C24, purchased from sigma using chromatography
Company, product identification：The composition of all fatty acids is analyzed (Fig. 1) in 18919-1AMP).By the comparison with standard spectrum,
Obtain the distribution of each aliphatic acid and content in test sample.The following table 1-2 shows the raw material of the present invention obtained according to coefficients data measured by chromatography,
The content of each aliphatic acid in DHA ester analog derivative, EPA ester analog derivative and soybean lecithin.The following table 3 is listed to be obtained according to coefficients data measured by chromatography
Commercially available antarctic krill oil in each aliphatic acid content.Each fat in each fat or oil composition C for implementing to obtain with comparative example example
Acid content measures according to the method described above.It should be pointed out that the DHA or the measured value of the percentage composition of EPA that are shown in table 4 are i.e.
Access rate for DHA or EPA.
The content (wt%) of each aliphatic acid in 1 soybean lecithin of table
The content of each aliphatic acid in 2 DHA ester analog derivative of table, EPA ester analog derivative
| DHA ester analog derivative (wt%) | EPA ester analog derivative (wt%) | |
| C16:0 | 1.1 | 1.6 |
| C16:1 | 0.7 | 0.3 |
| C18:0 | 0.3 | 0.6 |
| C18:1 | 1.0 | 0.4 |
| C18:2 | 0.3 | 0.2 |
| C20:1 | 0.1 | 0.1 |
| C21:0 | 0.2 | 0.1 |
| C20:4 | 1.8 | 2.0 |
| C23:0 | 0.5 | 0.3 |
| C20:5 | 8.8 | 76.2 |
| C24:0 | 0.3 | 0.1 |
| C24:1 | 1.0 | 1.3 |
| C22:6 | 79.7 | 10.2 |
| It is unknown | 4.2 | 6.2 |
The content (wt%) of each aliphatic acid in 3 antarctic krill oil of table
Embodiment 1-8 prepares the phosphatide type DHA fat or oil compositions similar with antarctic krill oil with phosphatide type EPA content
[fat or oil composition 1]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 455mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition 1.
The gas chromatogram of fat or oil composition 1 is as shown in Figure 2.
[fat or oil composition 2]
(1) DHA ester analog derivative 315mg is weighed, EPA ester analog derivative 385mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition 2.
[fat or oil composition 3]
(1) DHA ester analog derivative 280mg is weighed, EPA ester analog derivative 520mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 200mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition 3.
[fat or oil composition 4]
(1) DHA ester analog derivative 280mg is weighed, EPA ester analog derivative 520mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 200mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg TL IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition 4.
[fat or oil composition 5]
(1) DHA ester analog derivative 280mg is weighed, EPA ester analog derivative 520mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 200mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg SP435 lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition 5.
[fat or oil composition 6]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 455mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 5.25 μ l distilled water that precision is measured
It adds in rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition 6.
[fat or oil composition 7]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 525mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 24 hours, obtains fat or oil composition 7.
[fat or oil composition 8]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 525mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 8 hours, obtains fat or oil composition 8.
Comparative example 1-3：Prepare the fat or oil composition containing phosphatide type DHA Yu phosphatide type EPA content
[fat or oil composition c1]
(1) DHA ester analog derivative 520mg is weighed, EPA ester analog derivative 180mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition c1.
The gas chromatogram of fat or oil composition c1 is as shown in Figure 3.
[fat or oil composition c2]
(1) DHA ester analog derivative 125mg is weighed, EPA ester analog derivative 575mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition c2.
[fat or oil composition c3]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 455mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 400mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition c3.
[fat or oil composition c4]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 455mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin is added in reactor, the rich mixture obtained with step (1)
A is sufficiently mixed, and obtains rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 55 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 55 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition c4.
[fat or oil composition c5]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 455mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 30 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 30 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition c5.
[fat or oil composition c6]
(1) DHA ester analog derivative 245mg is weighed, EPA ester analog derivative 455mg adds in institute in reactor at room temperature
DHA ester analog derivative and EPA ester analog derivative are stated, is sufficiently mixed, obtains rich mixture A；
(2) soybean lecithin 300mg is weighed, soybean lecithin and 3ml n-hexanes are added in reactor, is obtained with step (1)
Rich mixture A be sufficiently mixed, obtain rich mixture B；
(3) the rich mixture B that step (2) obtains is preheated to 80 DEG C, the 4.5 μ l distilled water that precision measures is added
Enter to rich mixture B, abundant mixing；
(4) 300mg RM IM lipase preparations are added in the reaction mixture obtained to step (3), in 80 DEG C of temperature
The lower reaction of degree 16 hours, obtains fat or oil composition c6.
Table 4
Claims (6)
1. a kind of method for preparing the fat or oil composition containing phosphatide type DHA and phosphatide type EPA, the method includes walking as follows
Suddenly：
(1) at room temperature, DHA or its ester derivative with EPA or its ester derivative are mixed, obtains rich mixture
A,
Wherein, the content of DHA is not less than 75wt% in the DHA or its ester derivative, in the EPA or its ester derivative
The content of EPA is not less than 75wt%, the DHA or its ester derivative and the addition of EPA or its ester derivative is：Make
The weight ratio for obtaining DHA and EPA in rich mixture A is (30-70):(70-30)；
(2) the rich mixture A for obtaining soybean lecithin and step (1) is according to (10-35):The weight ratio of (90-65) carries out
Mixing obtains rich mixture B, wherein, the phosphorus level in soya lecithin fat content added in is not less than 75wt%；
(3) rich mixture that step (2) obtains is preheated to 40 DEG C -70 DEG C, adds in distilled water and mixed, the distillation
The addition of water is the 0-6wt% of enzyme preparation addition in step (4)；
(4) lipase of immobilization or phosphatide enzyme preparation is added in the reaction mixture obtained to step (3), at 40 DEG C -70
It is reacted at a temperature of DEG C, obtains fat or oil composition C；
Wherein, the content of phosphatide type DHA and phosphatide type EPA are respectively the 9.0-15.0wt% and 18.0- of the fat or oil composition C
25.0wt%.
2. the method for claim 1, wherein in step (1), the DHA or its ester derivative come from fish oil, sea
The arbitrary combination of any one of algae oil, microbial grease or above-mentioned grease；The EPA or its ester derivative come from fish
The arbitrary combination of any one of oil, algal oil, microbial grease or above-mentioned grease；
Preferably, the methyl esters type derivative of the DHA or its ester derivative selected from DHA, ethyl ester type derivative, glycerine ester type
The arbitrary combination of derivative or sequestered DHA or above-mentioned DHA or its ester derivative；The EPA or the choosing of its ester derivative
From in the methyl esters type derivative of EPA, ethyl ester type derivative, glycerine ester type derivative or sequestered EPA or above-mentioned EPA or its
The arbitrary combination of ester derivative；Preferably, the DHA or its ester derivative are DHA ethyl ester type derivative；Preferably, institute
It is EPA ethyl ester type derivative to state EPA or its ester derivative；
Preferably, the DHA or its ester derivative and the addition of EPA or its ester derivative are：So that grease mixing
The weight ratio of DHA and EPA is (35-45) in object A:(65-55).
3. method as claimed in claim 1 or 2, wherein, in step (2), in the soybean lecithin, the content of phosphatide is not less than
85wt%；
Preferably, rich mixture A soybean lecithin and step (1) obtained is according to (20-30):The weight ratio of (80-70)
It is mixed；
Preferably, described be blended in the presence of solvent-free system or organic solvent carries out；The organic solvent is preferably chosen from
Any one of group be made of n-hexane, isohexane, acetone or arbitrary combination；Preferably, the organic solvent for just oneself
Alkane；Preferably, the addition of the n-hexane is：Per 100mg phosphatide addition 1ml-1.5ml n-hexanes.
4. the method as described in any one of claim 1-3, wherein, in step (3), by preheating described in step at 45 DEG C -65
℃；
Preferably, 1.5-3.5wt% of the addition of the distilled water for enzyme preparation addition in step (4).
5. the method as described in any one of claim 1-13, wherein, in step (4), the lipase or phosphorus of the immobilization
Lipase preparation of the lipase preparations for the lipase preparation, preferably immobilization of immobilization；The lipase preparation of the immobilization
It can derive from one or more selected from following fungi：Rhizomucor miehei dredges the thermophilic hyphomycete of cotton like and aspergillus niger；It is preferred that
Ground, the lipase preparation of the immobilization are rhizomucor miehei RM IM lipase preparations, dredge the thermophilic hyphomycete TL IM fat of cotton like
Fat enzyme preparation or aspergillus niger SP435 preparations；Preferably, the addition of the lipase of the immobilization or phosphatide enzyme preparation is described
The 5wt%-35wt% of rich mixture B, preferably 10wt%-30wt%；
Preferably, the reaction temperature is 45 DEG C -65 DEG C；The reaction is preferred to be carried out 1-48 hours, preferably 8-24 hours.
6. the grease group containing phosphatide type DHA and phosphatide type EPA made from method according to any one of claims 1-5
Close object, wherein, the content of phosphatide type DHA and phosphatide type EPA be respectively the fat or oil composition C 9.0-15.0wt% and
18.0-25.0wt%.
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