CN107549332A - Strengthen method of baby's long-chain polyunsaturated fatty acid bioavailability and products thereof - Google Patents
Strengthen method of baby's long-chain polyunsaturated fatty acid bioavailability and products thereof Download PDFInfo
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- CN107549332A CN107549332A CN201710810822.XA CN201710810822A CN107549332A CN 107549332 A CN107549332 A CN 107549332A CN 201710810822 A CN201710810822 A CN 201710810822A CN 107549332 A CN107549332 A CN 107549332A
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Abstract
The invention discloses method of enhancing baby's long-chain polyunsaturated fatty acid bioavailability and products thereof, wherein, 50~80% triglycerides molecule contains MCFA and LCFUFA simultaneously in structured lipid product.The triglycerides molecule of such a structure is more easy to be degraded to DAG or a sweet ester in baby's stomach, strengthen the water solubility of product, be advantageous to emulsification, digestion and the absorption in follow-up baby's small intestine, the shortage of itself pancreatic lipase of baby's particularly ewborn infant and cholate is made up, LCPUFA bioavailability is improved from molecular level.
Description
Technical field
The invention belongs to grease processing technology field, and in particular to enhancing baby's long-chain polyunsaturated fatty acid biological utilisation
Method of rate and products thereof.
Background technology
Lipid in human milk provides 40~60% energy for baby, and in addition to energy supply, human milk additionally provides some phosphorus
Aliphatic acid necessary to fat, glycolipid and brain and retinal development, for example, docosahexaenoic acid (DHA) and arachidonic
Sour (ARA).DHA and ARA is two kinds of important long-chain polyunsaturated fatty acids (LCPUFA) being present in human milk, and LCPUFA is
The key component of central nervous system and the cell membrane phospholipid of retinal photoreceptor is formed, the immunity of baby can be strengthened,
Brain, most organs and visual acuity to baby is most important.DHA and the baby close phase of retinal development and cognitive function
Close；In addition, arachidonic acid can also promote growing for baby, and its metabolite PG2 series can adjust inferior colliculus
Brain, so as to the release of stimulating growth hormone, pituitary adrenocorticotropic hormone, ARA is also eicosanoid hormone (prostate
Element, leukotriene and thromboxane) direct precursor.In brief, take in enough DHA and ARA be maintain baby's normal growth and
The precondition of intelligence development.
Up to the present, pertinent literature is mainly reported logical using conventional plant grease, such as soybean oil, rapeseed oil, fish oil etc.
Cross in carrying out enzyme process or chemically catalyzed interesterification with middle chain triglyceride or ethyl ester or synthesized with medium-chain fatty acid (MCFA) acidolysis
Long carbon chain structured lipid (MLCT), the product of synthesis are mostly used for nutritional emulsions, and the crowd to there is digestion and metabolism dysfunction provides
Energy supplement.But for baby, itself digestive system development is unsound, while internal gastric lipase and pancreas fat
Fat enzyme is weaker to LCPUFA hydrolysis ability, thus reduces to the LCPUFA of some important physiological functions effect such as DHA and ARA
Absorb and utilize.Even if formula milk enterprise meets standard in the total amount of addition, but due to baby's digestive system feature, finally
Cause the intake deficiency in these important LCPUFA.But there are not document and patent report at present on how to improve baby
Product and preparation method of the youngster to these important LCPUFA bioavailabilities.
The content of the invention
The purpose of this part is to summarize some aspects of embodiments of the invention and briefly introduce some preferably to implement
Example.It may do a little simplified or be omitted to avoid making our department in this part and the description of the present application summary and denomination of invention
Point, the purpose of specification digest and denomination of invention obscure, and this simplification or omit and cannot be used for limiting the scope of the present invention.
In view of the technology of the method for above-mentioned and/or existing enhancing baby's long-chain polyunsaturated fatty acid bioavailability is empty
In vain, it is proposed that the present invention.
Therefore, one of purpose of the invention is that solve deficiency of the prior art, there is provided one kind enhancing baby's long-chain
The method of polyunsaturated fatty acid bioavailability.
In order to solve the above technical problems, the invention provides following technical scheme：One kind enhancing baby's long-chain how unsaturated
The method of fatty acid biological utilization rate, including, it will be enriched in DHA or the microbial grease rich in ARA mix with medium chain fatty acid ester,
The stirring reaction at 40~90 DEG C is added after lipase, free fatty is removed, obtains the middle Long carbon chain knot rich in DHA or ARA
Structure fat.
A kind of preferred side as the method for enhancing baby's long-chain polyunsaturated fatty acid bioavailability of the present invention
Case, wherein：Its addition of the lipase is the 6~15% of substrate quality；The lipase include Liposome 435,
One or more in Lipozyme TL IM, Lipozyme RM IM or Novozyme 435.
A kind of preferred side as the method for enhancing baby's long-chain polyunsaturated fatty acid bioavailability of the present invention
Case, wherein：The stirring reaction, its mixing speed are 400~600rpm.
A kind of preferred side as the method for enhancing baby's long-chain polyunsaturated fatty acid bioavailability of the present invention
Case, wherein：The medium chain fatty acid ester includes ethyl hexanoate, ethyl caprilate, ethyl caprate, caproic acid triglycerides, sad glycerine
One or more in three esters or Triglyceride DDD.
A kind of preferred side as the method for enhancing baby's long-chain polyunsaturated fatty acid bioavailability of the present invention
Case, wherein：Described to will be enriched in DHA or the microbial grease rich in ARA mixes with medium chain fatty acid ester, it is by the more insatiable hungers of long-chain
With fatty acid triglycercide and Medium chain fatty acetoacetic ester in molar ratio 1:2~8 mixing or by long-chain polyunsaturated fatty acid glycerine
Three esters and MCT Oil in molar ratio 1:0.8~1.5 mixing.
Another object of the present invention is that solve deficiency of the prior art, then provides another enhancing baby long-chain more not
The method of saturated fatty acid bioavailability.
In order to solve the above technical problems, the invention provides following technical scheme：One kind enhancing baby's long-chain how unsaturated
The method of fatty acid biological utilization rate, including, it will be enriched in DHA or the microbial grease rich in ARA mix with medium chain fatty acid, add
Enter to account for after the lipase of substrate quality 6~15% stirring reaction under 40~90 DEG C, 400~600rpm, remove free fatty,
Obtain the middle Long carbon chain structured lipid rich in DHA or ARA；The medium chain fatty acid include caproic acid, octanoic acid or capric acid in one kind or
It is several.
A kind of preferred side as the method for enhancing baby's long-chain polyunsaturated fatty acid bioavailability of the present invention
Case, wherein：Described to will be enriched in DHA or the microbial grease rich in ARA mixes with medium chain fatty acid, it is by long-chain how unsaturated
Fatty acid triglycercide and medium chain fatty acid in molar ratio 1:4~12 mixing.
Another object of the present invention is that solve deficiency of the prior art, there is provided another enhancing more insatiable hunger of baby's long-chain
With the method for fatty acid biological utilization rate.
In order to solve the above technical problems, the invention provides following technical scheme：One kind enhancing baby's long-chain how unsaturated
The method of fatty acid biological utilization rate, will be enriched in DHA or the microbial grease rich in ARA mixes with medium chain fatty acid ester, add
The base catalyst of substrate quality 0.2~3% is accounted for, the stirring reaction at 60~120 DEG C, free fatty is removed, is rich in
DHA or ARA middle Long carbon chain structured lipid；The base catalyst includes potassium hydroxide or caustic alcohol；The medium chain fatty acid ester
Including one in ethyl hexanoate, ethyl caprilate, ethyl caprate, caproic acid triglycerides, Trivent OCG or Triglyceride DDD
Kind is several.
A kind of preferred side as the method for enhancing baby's long-chain polyunsaturated fatty acid bioavailability of the present invention
Case, wherein：Described to will be enriched in DHA or the microbial grease rich in ARA mixes with medium chain fatty acid ester, it is by the more insatiable hungers of long-chain
1 is pressed with fatty acid triglycercide and Medium chain fatty acetoacetic ester:2~8 mixing or by long-chain polyunsaturated fatty acid triglycerides with
MCT Oil presses 1：0.8~1.5.
Another object of the present invention is that solve deficiency of the prior art, there is provided one kind enhancing more insatiable hungers of baby's long-chain
With the structured lipid nourishing additive agent of fatty acid biological utilization rate.
In order to solve the above technical problems, the invention provides following technical scheme：One kind enhancing baby's long-chain how unsaturated
The structured lipid nourishing additive agent of fatty acid biological utilization rate, 50~80% triglycerides molecule is simultaneously in structured lipid product
Contain MCFA and LCFUFA.
Beneficial effect possessed by the present invention：
Based on baby's digestive system feature, i.e., gastric lipase activity is higher and pancreatic lipase and cholate content it is relatively low, utilize
The relatively strong water-soluble and facile hydrolysis of medium chain fatty acid (MCFA), by ester exchange or acidolysis reaction by MCFA with having to baby
The LCPUFA of important physiological function is commonly connected to same triglycerides molecule, forms the structure glycerine rich in MCFA and LCPUFA
Three ester products, molecule of the triglycerides simultaneously containing MCFA and LCPUFA accounts for more than 50% in product, the glycerine three of such a structure
Ester molecule is more easy to be degraded to DAG or a sweet ester in baby's stomach, strengthens the water solubility of product, is advantageous to follow-up baby's small intestine
In emulsification, digestion and absorption, the shortage of itself pancreatic lipase of baby's particularly ewborn infant and cholate is made up, from molecular level
Improve LCPUFA bioavailability.Meanwhile primary raw material used is the algae oil rich in LCPUFA such as ARA or DHA, belonging to can be again
Production-goods source, securely and reliably, used method are ester exchange or acidolysis reaction, simple and easy to do, efficiency high, are suitable for industrial big rule
Mould produces.Therefore, product involved in the present invention and preparation method thereof is respectively provided with obvious beneficial effect, has larger city
Field prospect.
Brief description of the drawings
In order to illustrate the technical solution of the embodiments of the present invention more clearly, required use in being described below to embodiment
Accompanying drawing be briefly described, it should be apparent that, drawings in the following description are only some embodiments of the present invention, for this
For the those of ordinary skill of field, without having to pay creative labor, it can also be obtained according to these accompanying drawings other
Accompanying drawing.Wherein：
Fig. 1 is the triglycerides liquid chromatogram of the physical mixture of embodiment 1 (A) and end-product (B)；
Fig. 2 is the triglycerides liquid chromatogram of the reaction raw materials of embodiment 3 (A) and end-product (B).
Embodiment
In order to facilitate the understanding of the purposes, features and advantages of the present invention, with reference to specific embodiment pair
The embodiment of the present invention is described in detail.
Many details are elaborated in the following description to facilitate a thorough understanding of the present invention, still the present invention can be with
It is different from other manner described here using other to implement, those skilled in the art can be without prejudice to intension of the present invention
In the case of do similar popularization, therefore the present invention is not limited by following public specific embodiment.
Secondly, " one embodiment " or " embodiment " referred to herein refers to may be included at least one realization side of the present invention
Special characteristic, structure or characteristic in formula." in one embodiment " that different places occur in this manual not refers both to
Same embodiment, nor the single or selective embodiment mutually exclusive with other embodiment.
Embodiment 1
In batch reactor, pungent Triglyceride DDD and the algae oil rich in arachidonic acid (ARA) are 1 in molar ratio:1
Mixed, 8% immobilized lipase Lipozyme 435 of addition, stirring reaction 3h, speed of agitator 500r/ at 60 DEG C of normal pressure
Min, after reaction terminates, lipase is filtered to remove, and free fatty is removed by molecular distillation, obtain being rich in arachidonic acid
(ARA) middle Long carbon chain structured lipid, analyze through HPLC, and the middle Long carbon chain structured lipid containing MCFA and ARA contains simultaneously in molecule
Amount reaches 53.75%.React starting material, physical mixture and the aliphatic acid composition of reaction product and distribution is as shown in table 1, it is sweet
Oily three esters composition is shown in Table 2, and its HPLC collection of illustrative plates is as shown in Figure 1.The fat of the reactant of table 1, physical mixture and ester exchange offspring
Acid composition and distribution.
Triglycerides forms in the reactant of table 2
| Triglycerides title | Triglycerides (%) |
| MMM | 6.12 |
| MLCT | 53.75 |
| LLL | 40.13 |
Embodiment 2
In batch reactor, will be enriched in ARA algae oil and capric acid is 1 in molar ratio:4 are mixed, and it is solid to add 10%
Immobilized lipase Lipozyme RMIM, stirring reaction 4h, speed of agitator 400r/min at 50 DEG C of normal pressure, after reaction terminates, mistake
Lipase is filtered out, and free fatty is removed by molecular distillation, the middle Long carbon chain structured lipid rich in ARA is obtained, through HPLC
Analyze, the content of the middle Long carbon chain structured lipid containing MCFA and ARA reaches 55.31% simultaneously in molecule.The fat of reaction product
Acid composition and distribution are as shown in table 3, and triglycerides composition is as shown in table 4.
The aliphatic acid composition of the acid hydrolysate of table 3 and distribution
Triglycerides forms in the reactant of table 4
| Triglycerides title | Triglycerides (%) |
| MLCT | 55.31 |
| LLL | 44.69 |
Embodiment 3
A certain amount of DHA algal oil and octanoic acid are placed in batch reactor, mol ratio 1:5, add 10% fixation
Change Lipozyme RMIM, stirring reaction 6h, speed of agitator 400r/min at 55 DEG C of normal pressure, after reaction terminates, filtering
Lipase is removed, the middle Long carbon chain structure fat prod of acquisition contains 46.4% octanoic acid, simultaneously containing MCFA's and DHA in molecule
The content of middle Long carbon chain structured lipid reaches 51.55%.The aliphatic acid composition of acid hydrolysate and distribution are as shown in table 5, in reactant
Triglycerides composition is as shown in table 6.
The aliphatic acid composition of the acid hydrolysate of table 5 and distribution
Triglycerides forms in the reactant of table 6
| Triglycerides title | Triglycerides (%) |
| MLCT | 51.55 |
| LLL | 39.45 |
Embodiment 4
A certain amount of DHA algal oil and pungent Triglyceride DDD are placed in reactor, mol ratio 1:1.5, add 8%
Immobilized lipase Lipozyme TL IM, stirring reaction 4h at 55 DEG C of normal pressure, speed of agitator 600r/min, reaction terminate
Afterwards, lipase is filtered to remove, and free fatty is removed by molecular distillation, obtains the middle Long carbon chain structured lipid rich in DHA, warp
HPLC is analyzed, and the content of the middle Long carbon chain structured lipid containing MCFA and DHA reaches 55.37% simultaneously in molecule.Reaction product
Aliphatic acid forms and distribution is as shown in table 7, and triglycerides composition is as shown in table 8.
The aliphatic acid composition of the acid hydrolysate of table 7 and distribution
Triglycerides forms in the reactant of table 8
| Triglycerides title | Triglycerides (%) |
| MMM | 15.7 |
| MLCT | 55.37 |
| LLL | 28.93 |
Embodiment 5
A certain amount of DHA algal oil and pungent Triglyceride DDD are placed in reactor, mol ratio 1:1.5, addition accounts for bottom
The caustic alcohol of amount of substance 1%, stirring reaction 3h, speed of agitator 800r/min at 100 DEG C of normal pressure, after reaction terminates, cross and filter out
Lipase is removed, and free fatty is removed by molecular distillation, the middle Long carbon chain structured lipid rich in DHA is obtained, is analyzed through HPLC,
The content of the middle Long carbon chain structured lipid containing MCFA and DHA reaches 53.73% simultaneously in molecule.
Embodiment 6
Ester exchange reaction products obtained therefrom (example 1,4 and 5), and the product (example 2 and 3) of acidolysis reaction, in glycerine three
Ester composition has higher similitude respectively.Example 1 and the product in example 3 and the algae oil rich in DHA and ARA are selected respectively
Carry out baby's external digestion simulated experiment.The vigor of baby's gastric lipase is similar with being grown up, but the concentration of pancreatic lipase is adult's
5-10%, the content of cholate only have be grown up 50%.Therefore, in vitro in simulated test, its pancreas is reduced in the level of adult
Lipase concentration is 10%, and cholate content is 50%.In simulated test, the concentration of gastric lipase is 100 μ g/mL, and the gastric juice of people
Concentration is consistent, and cholate and pancreatic lipase solution concentration are diluted to 2mM and 25 μ g/mL in small intestine simulated test.Experiment is in 37 degree of 50mL
Thermostatic container in carry out, rotor speed 1,000rpm.15mL samples and 3mL peptic digest liquid are added in 0min, adjusts pH
Value takes 1mL samples to be detected respectively to 5.5 in 29min；In 30min, pH to 6.25 is adjusted, adds small intestine digestive juice,
The separately sampled detections of 60th and 90min.Acquired results are as follows：
By lipid digestion experiment outside infants it is obvious that by being rich in MLCT product in example 1 and 3 in stomach
And the production rate of the partial glyceride in small intestine illustrates that such product is improving baby apparently higher than single DHA and ARA algae oils
Youngster in terms of functional lipids digestion to having obvious advantage.
Relatively strong water-soluble and facile hydrolysis of the invention based on MCFA, pass through enzyme process or chemically catalyzed interesterification or enzyme process acidolysis
MCFA and the LCPUFA for having important physiological function to baby are commonly connected to same triglycerides molecule by reaction, and formation is rich in
MCFA and LCPUFA structured triglyceride product, molecule of the triglycerides simultaneously containing MCFA and LCPUFA accounts for 50% in product
More than, the triglycerides molecule of such a structure is more easy to be degraded to DAG or a sweet ester in baby's stomach, strengthens the water-soluble of product
Property, be advantageous to emulsification, digestion and the absorption in follow-up baby's small intestine, make up itself pancreatic lipase of baby's particularly ewborn infant and courage
The shortage of salt, LCPUFA bioavailability is improved from molecular level.
It should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention and it is unrestricted, although with reference to preferable
The present invention is described in detail embodiment, it will be understood by those within the art that, can be to the technology of the present invention
Scheme is modified or equivalent substitution, and without departing from the spirit and scope of technical solution of the present invention, it all should cover in this hair
Among bright right.
Claims (10)
- A kind of 1. method for strengthening baby's long-chain polyunsaturated fatty acid bioavailability, it is characterised in that：Including,It will be enriched in DHA or the microbial grease rich in ARA mix with medium chain fatty acid ester；Add lipase after at 40~90 DEG C stirring reaction；Free fatty is removed, obtains the middle Long carbon chain structured lipid rich in DHA or ARA.
- 2. strengthen the method for baby's long-chain polyunsaturated fatty acid bioavailability according to claim 1, it is characterised in that：Its addition of the lipase is the 6~15% of substrate quality；The lipase is included in Liposome 435, Lipozyme TL IM, Lipozyme RM IM or Novozyme 435 One or more.
- 3. the method for enhancing baby's long-chain polyunsaturated fatty acid bioavailability according to claim 1 or claim 2, its feature exist In：The stirring reaction, its mixing speed are 400~600rpm.
- 4. strengthen the method for baby's long-chain polyunsaturated fatty acid bioavailability according to claim 1, it is characterised in that： The medium chain fatty acid ester includes ethyl hexanoate, ethyl caprilate, ethyl caprate, caproic acid triglycerides, Trivent OCG or the last of the ten Heavenly stems One or more in acid glycerol three ester.
- 5. strengthen the method for baby's long-chain polyunsaturated fatty acid bioavailability according to claim 1, it is characterised in that： Described to will be enriched in DHA or the microbial grease rich in ARA mixes with medium chain fatty acid ester, it is by long-chain polyunsaturated fatty acid Triglycerides and Medium chain fatty acetoacetic ester in molar ratio 1:2~8 mix or by long-chain polyunsaturated fatty acid triglycerides with Chain fatty acid triglycerides in molar ratio 1:0.8~1.5 mixing.
- A kind of 6. method for strengthening baby's long-chain polyunsaturated fatty acid bioavailability, it is characterised in that：Including,It will be enriched in DHA or the microbial grease rich in ARA mix with medium chain fatty acid；Add and account for after the lipase of substrate quality 6~15% stirring reaction under 40~90 DEG C, 400~600rpm；Free fatty is removed, obtains the middle Long carbon chain structured lipid rich in DHA or ARA；The medium chain fatty acid includes the one or more in caproic acid, octanoic acid or capric acid.
- 7. strengthen the method for baby's long-chain polyunsaturated fatty acid bioavailability according to claim 6, it is characterised in that： Described to will be enriched in DHA or the microbial grease rich in ARA mixes with medium chain fatty acid, it is that long-chain polyunsaturated fatty acid is sweet Oily three esters and medium chain fatty acid in molar ratio 1:4~12 mixing.
- A kind of 8. method for strengthening baby's long-chain polyunsaturated fatty acid bioavailability, it is characterised in that：Including,It will be enriched in DHA or the microbial grease rich in ARA mix with medium chain fatty acid ester；Add and account for after the base catalyst of substrate quality 0.2~3% stirring reaction at 60~120 DEG C；Free fatty is removed, obtains the middle Long carbon chain structured lipid rich in DHA or ARA；The base catalyst includes potassium hydroxide or caustic alcohol；The medium chain fatty acid ester includes ethyl hexanoate, ethyl caprilate, ethyl caprate, caproic acid triglycerides, Trivent OCG Or the one or more in Triglyceride DDD.
- 9. strengthen the method for baby's long-chain polyunsaturated fatty acid bioavailability according to claim 8, it is characterised in that： Described to will be enriched in DHA or the microbial grease rich in ARA mixes with medium chain fatty acid ester, it is by long-chain polyunsaturated fatty acid Triglycerides presses 1 with Medium chain fatty acetoacetic ester:2~8 mixing or by long-chain polyunsaturated fatty acid triglycerides and Medium chain fatty Acid glycerol three ester presses 1：0.8~1.5.
- 10. a kind of structured lipid nourishing additive agent for strengthening baby's long-chain polyunsaturated fatty acid bioavailability, its feature exist In：50~80% triglycerides molecule contains MCFA and LCFUFA simultaneously in structured lipid product.
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| CN108652010A (en) * | 2018-03-27 | 2018-10-16 | 广州天来宝生物科技有限公司 | A kind of 3 quick-dissolving agent of omega and preparation method thereof |
| CN111363766A (en) * | 2020-03-20 | 2020-07-03 | 江南大学 | Preparation method of structural lipid for improving DHA bioavailability and product thereof |
| WO2020248710A1 (en) * | 2019-06-14 | 2020-12-17 | 广东省农业科学院蚕业与农产品加工研究所 | Grease composition and preparation method therefor |
| CN115976125A (en) * | 2022-12-02 | 2023-04-18 | 河北康睿达脂质有限公司 | Structured lipid, method for producing same, structured fat emulsion, and structured fat emulsion preparation |
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