CN111172211A - Method for preparing long-chain polyunsaturated fatty acid glyceride rich in fish oil n-3 by enzyme method and product thereof - Google Patents
Method for preparing long-chain polyunsaturated fatty acid glyceride rich in fish oil n-3 by enzyme method and product thereof Download PDFInfo
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- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 98
- 235000021323 fish oil Nutrition 0.000 title claims abstract description 46
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims description 48
- 102000004190 Enzymes Human genes 0.000 title claims description 25
- 108090000790 Enzymes Proteins 0.000 title claims description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 72
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 68
- 108090001060 Lipase Proteins 0.000 claims abstract description 27
- 102000004882 Lipase Human genes 0.000 claims abstract description 27
- 239000004367 Lipase Substances 0.000 claims abstract description 27
- 235000019421 lipase Nutrition 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 238000003756 stirring Methods 0.000 claims abstract description 20
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 16
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 13
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 19
- 229930195729 fatty acid Natural products 0.000 claims description 19
- 239000000194 fatty acid Substances 0.000 claims description 19
- 238000000199 molecular distillation Methods 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 14
- 108010084311 Novozyme 435 Proteins 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 108010048733 Lipozyme Proteins 0.000 claims description 7
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 abstract description 5
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract description 5
- 238000011112 process operation Methods 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 100
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 19
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 18
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 18
- 150000003626 triacylglycerols Chemical class 0.000 description 11
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 241000238366 Cephalopoda Species 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 241001125046 Sardina pilchardus Species 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 230000036996 cardiovascular health Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007407 health benefit Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
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Abstract
本发明公开了一种酶法制备富含鱼油n‑3长链多不饱和脂肪酸甘油酯的方法及其产品，包括，酶催化醇解反应获得富含n‑3长链多不饱和脂肪酸的中间酶解产品；将中间酶解产品与甘油按照摩尔比为1:3～6加入间歇反应器中，加入3～12wt％的脂肪酶，在温度30～70℃，搅拌速率为300～800rpm的条件下反应6～12小时，获得甘油一酯产品；将中间酶解产品与甘油按照摩尔比为1:0.5～2加入间歇反应器中，加入4～14wt％的脂肪酶，在温度30～70℃，搅拌速率为300～800rpm的条件下反应6～12小时，获得甘油二酯产品。本发明将酶法醇解富集与酶法甘油解相结合制备富含n‑3长链多不饱和脂肪酸的甘油二酯或甘油一酯产品，工艺操作简单，得到的甘油二酯或甘油一酯产品n‑3长链多不饱和脂肪酸含量高。The invention discloses an enzymatic method for preparing glycerides rich in n-3 long-chain polyunsaturated fatty acids in fish oil and a product thereof. Enzymatic hydrolysis product; the intermediate enzymatic hydrolysis product and glycerol are added into the batch reactor according to the molar ratio of 1:3～6, 3～12wt% lipase is added, and the temperature is 30～70℃, and the stirring speed is 300～800rpm. The reaction is carried out for 6-12 hours to obtain a monoglyceride product; the intermediate enzymatic hydrolysis product and glycerol are added to the batch reactor according to the molar ratio of 1:0.5-2, 4-14 wt% lipase is added, and the temperature is 30-70 ° C. , and the reaction is carried out for 6 to 12 hours under the condition that the stirring speed is 300 to 800 rpm to obtain a diglyceride product. The invention combines enzymatic alcoholysis enrichment and enzymatic glycerolysis to prepare diglyceride or monoglyceride products rich in n-3 long-chain polyunsaturated fatty acids, and the process operation is simple, and the obtained diglyceride or monoglyceride The ester product has a high content of n-3 long-chain polyunsaturated fatty acids.
Description
Technical Field
The invention belongs to the technical field of grease, and particularly relates to a method for preparing long-chain polyunsaturated fatty glyceride rich in fish oil n-3 by an enzyme method and a product thereof.
Background
fish oil in the deep sea is a major source of n-3 long chain polyunsaturated fatty acids (mainly eicosapentaenoic acid, EPA, C20:5n-3 and docosahexaenoic acid, DHA, C22:6 n-3). n-3 long chain polyunsaturated fatty acids have long been healthy nutritional supplements with many health benefits, including effects to improve cardiovascular health, brain function and overall health during pregnancy EPA and DHA are non-essential n-3 fatty acids because the human body can convert essential α -linolenic acid (ALA) to EPA and DHA.
Because digestive enzymes in human bodies have certain substrate selectivity, the hydrolysis activity of long-chain polyunsaturated fatty acid is not high, and the digestion and absorption of the deep sea fish oil are influenced to a certain extent. In view of the important physiological functions of the n-3 polyunsaturated fatty acids of fish oil, it can be converted into diglyceride or (and) monoglyceride forms by a process which can act as a predigestion and is beneficial to the digestive absorption of fish oil. Meanwhile, diglyceride or (and) monoglyceride rich in n-3 polyunsaturated fatty acid can be used as an emulsifier in food, so that fish oil is developed into an important food additive to be applied to common food, and a new channel is provided for the public to supplement n-3 polyunsaturated fatty acid.
However, when the existing research process is used for preparing diglyceride or (and) monoglyceride of fish oil source, fish oil is generally directly used as raw material, and the product is obtained by using a glycerolysis method, wherein the content of n-3 polyunsaturated fatty acid in the product is not high, and the additional value of the fish oil derived product is limited to a certain extent. Therefore, a method for enriching the fish oil n-3 long-chain polyunsaturated fatty acid glyceride and a product thereof are needed in the field.
Disclosure of Invention
This section is for the purpose of summarizing some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. In this section, as well as in the abstract and the title of the invention of this application, simplifications or omissions may be made to avoid obscuring the purpose of the section, the abstract and the title, and such simplifications or omissions are not intended to limit the scope of the invention.
The present invention has been made in view of the above-mentioned technical drawbacks.
Therefore, in one aspect of the invention, the defects in the prior art are overcome, and the method for preparing the long-chain polyunsaturated fatty acid glyceride rich in the fish oil n-3 by the enzyme method is provided.
In order to solve the technical problems, the invention provides the following technical scheme: a method for preparing long-chain polyunsaturated fatty acid glyceride rich in fish oil n-3 by an enzyme method comprises the following steps: adding fish oil and ethanol into an intermittent reactor according to a substrate molar ratio of 1: 3-9, adding 4-15 wt% of lipase, reacting for 4-12 hours at a temperature of 25-45 ℃ and a stirring speed of 300-800 rpm, and obtaining an intermediate enzymolysis product rich in n-3 long-chain polyunsaturated fatty acid, wherein the content of monoglyceride and diglyceride in the intermediate enzymolysis product is more than 30%, and the content of monoglyceride is more than 3%; preparing monoglyceride: after ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, adding the intermediate enzymolysis product and glycerol into an intermittent reactor according to the molar ratio of 1: 3-6, adding 3-12 wt% of lipase, and reacting for 6-12 hours at the temperature of 30-70 ℃ and the stirring speed of 300-800 rpm to obtain a monoglyceride product rich in n-3 long-chain polyunsaturated fatty acids, wherein the content of the monoglyceride is more than 65%, the content of the n-3 long-chain polyunsaturated fatty acids is more than 45%, and the content of the n-3 long-chain polyunsaturated fatty acids in the monoglyceride is more than 50%; preparing diglyceride: after ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, adding the intermediate enzymolysis product and glycerol into an intermittent reactor according to the molar ratio of 1: 0.5-2, adding 4-14 wt% of lipase, and reacting for 6-12 hours at the temperature of 30-70 ℃ and the stirring speed of 300-800 rpm to obtain a diglyceride product rich in n-3 long-chain polyunsaturated fatty acid, wherein the content of diglyceride is more than 50%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, and the content of n-3 long-chain polyunsaturated fatty acid in diglyceride is more than 50%.
As a preferable scheme of the method for preparing the fish oil-rich n-3 long-chain polyunsaturated fatty acid glyceride by the enzyme method, the method comprises the following steps: the fish oil is deep sea fish oil, and the content of EPA and DHA is more than 20%.
As a preferable scheme of the method for preparing the fish oil-rich n-3 long-chain polyunsaturated fatty acid glyceride by the enzyme method, the method comprises the following steps: the enzyme catalyzes alcoholysis reaction, wherein the Lipase is one or more of Lipozyme RM IM, Lipozyme TL IM and Lipase AY-30 SD.
As a preferable scheme of the method for preparing the fish oil-rich n-3 long-chain polyunsaturated fatty acid glyceride by the enzyme method, the method comprises the following steps: the enzyme catalyzes alcoholysis reaction, wherein the content of n-3 long-chain polyunsaturated fatty acid in the intermediate enzymolysis product is more than 45%.
As a preferable scheme of the method for preparing the fish oil-rich n-3 long-chain polyunsaturated fatty acid glyceride by the enzyme method, the method comprises the following steps: the monoglyceride is prepared, wherein the lipase is a lipase Novozym 435.
As a preferable scheme of the method for preparing the fish oil-rich n-3 long-chain polyunsaturated fatty acid glyceride by the enzyme method, the method comprises the following steps: the preparation of diglyceride is described, wherein the lipase is lipase Novozym 435.
As a preferable scheme of the method for preparing the fish oil-rich n-3 long-chain polyunsaturated fatty acid glyceride by the enzyme method, the method comprises the following steps: the enzyme catalyzes alcoholysis reaction, wherein the molar ratio of fish oil to ethanol is 1:3, the addition amount of lipase is 15 wt%, the reaction temperature is 25 ℃, and the reaction time is 4 hours.
As another aspect of the invention, the invention overcomes the defects in the prior art and provides a glyceride product prepared by an enzymatic method for preparing the glyceride rich in the fish oil n-3 long-chain polyunsaturated fatty acid.
As a preferred embodiment of the glyceride product of the present invention: the glyceride products include monoglyceride products rich in n-3 long chain polyunsaturated fatty acids and diglyceride products rich in n-3 long chain polyunsaturated fatty acids.
As a preferred embodiment of the glyceride product of the present invention: the content of monoglyceride in the monoglyceride product is more than 65%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, the content of n-3 long-chain polyunsaturated fatty acid in the monoglyceride is more than 50%, the content of diglyceride in the diglyceride product is more than 50%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, and the content of n-3 long-chain polyunsaturated fatty acid in the diglyceride is more than 50%.
The invention has the beneficial effects that:
(1) the method comprises the steps of firstly preparing a glyceride product rich in n-3 long-chain polyunsaturated fatty acid by adopting a two-step enzyme method, enriching the n-3 long-chain polyunsaturated fatty acid by utilizing the inertia of lipase to the n-3 long-chain polyunsaturated fatty acid through an enzymatic alcoholysis reaction, and obtaining an intermediate enzymolysis product rich in the n-3 long-chain polyunsaturated fatty acid; removing ethanol and fatty acid ethyl ester by vacuum distillation and molecular distillation, performing glycerolysis reaction under enzyme catalysis, and preferably selecting conditions to obtain diglyceride or monoglyceride product rich in n-3 long-chain polyunsaturated fatty acid, wherein the content of monoglyceride in the monoglyceride product is more than 65%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, the content of n-3 long-chain polyunsaturated fatty acid in monoglyceride is more than 50%, the content of diglyceride in the diglyceride product is more than 50%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, and the content of n-3 long-chain polyunsaturated fatty acid in diglyceride is more than 50%.
(2) The invention combines enzymatic alcoholysis enrichment and enzymatic glycerolysis to prepare the diglyceride or monoglyceride product rich in n-3 long-chain polyunsaturated fatty acid, the process operation is simple and the industrial application is easy, the n-3 long-chain polyunsaturated fatty acid content of the obtained diglyceride or monoglyceride product is high, meanwhile, the product form is beneficial to the digestion and absorption of the n-3 long-chain polyunsaturated fatty acid, and the product can be further purified to be used as a food emulsifier, thereby expanding the channel of common people for taking in the n-3 long-chain polyunsaturated fatty acid.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with examples are described in detail below.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
Furthermore, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1
(1) Tuna oil and ethanol are added into a sealable batch reactor according to the substrate molar ratio of 1:3 (fish oil/ethanol), 15 wt% of Lipozyme RM IM is added, the mixture reacts for 4 hours at the temperature of 25 ℃ and the stirring speed of 400rpm, the content of n-3 long-chain polyunsaturated fatty acid in the intermediate enzymatic hydrolysis product is analyzed, and the chemical composition of the intermediate enzymatic hydrolysis product is shown in Table 1.
TABLE 1
(2) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, adding the intermediate enzymolysis product and glycerol into an intermittent reactor according to the substrate molar ratio of 1:6 (intermediate enzymolysis product/glycerol), adding 3 wt% of Novozym 435, and reacting for 12 hours at the temperature of 70 ℃ and the stirring speed of 800rpm to obtain the monoglyceride product. The composition of the obtained monoglyceride product is shown in Table 2, and the composition of each component n-3 long-chain polyunsaturated fatty acid in the monoglyceride product is shown in Table 3.
TABLE 2
| Glyceride composition | Content (%) |
| Triglycerides | 7.3 |
| Diglyceride | 22.1 |
| Monoglyceride | 70.6 |
TABLE 3
| Fatty acids | Triglycerides | Diglyceride | Monoglyceride |
| C20:5(n-3)EPA | 13.1 | 15.6 | 15.4 |
| C22:6(n-3)DHA | 37.6 | 42.9 | 41.2 |
| EPA+DHA | 50.7 | 58.5 | 56.6 |
(3) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by reduced pressure distillation and molecular distillation, the intermediate enzymolysis product and glycerol are added into an intermittent reactor according to the substrate molar ratio of 1:0.5 (intermediate enzymolysis product/glycerol), 14 wt% of Novozym 435 is added, and the reaction is carried out for 12 hours at the temperature of 50 ℃ and the stirring speed of 600rpm, so as to obtain the diglyceride product. The composition of the resulting diglyceride product is shown in Table 4, and the composition of the n-3 long-chain polyunsaturated fatty acids as the respective components in the diglyceride product is shown in Table 5.
TABLE 4
| Glyceride composition | Content (%) |
| Triglycerides | 27.5 |
| Diglyceride | 56.4 |
| Monoglyceride | 16.1 |
TABLE 5
Example 2
(1) Adding squid oil and ethanol into a sealable batch reactor according to a substrate molar ratio of 1:6 (fish oil/ethanol), respectively adding 10 wt% Lipozyme TL IM, and reacting for 12 hours at the temperature of 30 ℃ and the stirring speed of 600rpm to obtain an intermediate enzymolysis product rich in n-3 long-chain polyunsaturated fatty acid. The fatty acid composition of the intermediate enzymatic product obtained is shown in table 6.
TABLE 6
| Fatty acids | Fish oil (%) | Intermediate enzymatic product (%) | Glyceride composition | Content (wt.) |
| C14:0 | 6.4 | 2.4 | Triglycerides | 65.2 |
| C16:0 | 14.7 | 7.3 | Diglyceride | 30.3 |
| C16:1 | 7.5 | 2.6 | Monoglyceride | 4.5 |
| C18:0 | 2.3 | 0.8 | ||
| C18:1 | 17.3 | 8.4 | ||
| C18:2 | 2.1 | 1.1 | ||
| C18:3 | 2.4 | 1.2 | ||
| C20:1 | 10.3 | 12.5 | ||
| C20:4 | 1.9 | 4.1 | ||
| C20:5(n-3)EPA | 8.5 | 15.7 | ||
| C22:1 | 4.1 | 8.5 | ||
| C22:6(n-3)DHA | 22.1 | 34.8 | ||
| EPA+DHA | 30.6 | 50.5 |
(2) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, the intermediate enzymolysis product and glycerol are added into a batch reactor according to the substrate molar ratio of 1:4 (intermediate enzymolysis product/glycerol), 8 wt% of Novozym 435 is added, and the reaction is carried out for 8 hours under the conditions that the temperature is 50 ℃ and the stirring speed is 600rpm, so as to obtain the monoglyceride product. The composition of the obtained monoglyceride product is shown in Table 7, and the composition of each component n-3 long-chain polyunsaturated fatty acid in the monoglyceride product is shown in Table 8.
TABLE 7
TABLE 8
| Triglycerides | Diglyceride | Monoglyceride | |
| C20:5(n-3)EPA | 14.1 | 17 | 17.5 |
| C22:6(n-3)DHA | 30.8 | 36.2 | 36.5 |
| EPA+DHA | 44.9 | 53.2 | 54 |
(3) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, the intermediate enzymolysis product and glycerol are added into a batch reactor according to the substrate molar ratio of 1:1 (intermediate enzymolysis product/glycerol), 8 wt% of Novozym 435 is added, and the reaction is carried out for 9 hours under the conditions that the temperature is 70 ℃ and the stirring speed is 400rpm, so as to obtain the diglyceride product. The composition of the resulting diglyceride product is shown in Table 9, and the composition of the n-3 long-chain polyunsaturated fatty acids as the respective components in the diglyceride product is shown in Table 10.
TABLE 9
| Glyceride composition | Content (%) |
| Triglycerides | 28.5 |
| Diglyceride | 57.8 |
| Monoglyceride | 13.7 |
Watch 10
| Triglycerides | Diglyceride | Monoglyceride | |
| C20:5(n-3)EPA | 14.3 | 16.5 | 17.2 |
| C22:6(n-3)DHA | 32.2 | 35.7 | 35.9 |
| EPA+DHA | 46.5 | 52.2 | 53.1 |
Example 3
(1) Adding sardine oil and ethanol into a sealable batch reactor according to the substrate molar ratio of 1:9 (fish oil/ethanol), respectively adding 4 wt% of Lipase AY-30SD, and reacting for 8 hours at the temperature of 45 ℃ and the stirring speed of 800rpm to obtain an intermediate enzymolysis product rich in n-3 long-chain polyunsaturated fatty acid. The fatty acid composition of the intermediate enzymatic product obtained is shown in table 11.
TABLE 11
(2) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, the intermediate enzymolysis product and glycerol are added into a batch reactor according to the substrate molar ratio of 1:3 (intermediate enzymolysis product/glycerol), 12 wt% of Novozym 435 is added, and the reaction is carried out for 6 hours under the conditions that the temperature is 30 ℃ and the stirring speed is 400rpm, so as to obtain the monoglyceride product. The composition of the obtained monoglyceride product is shown in Table 12, and the composition of each component n-3 long-chain polyunsaturated fatty acid in the monoglyceride product is shown in Table 13.
TABLE 12
| Glyceride composition | Content (%) |
| Triglycerides | 10.1 |
| Diglyceride | 23.2 |
| Monoglyceride | 66.7 |
Watch 13
| Triglycerides | Diglyceride | Monoglyceride | |
| C20:5(n-3)EPA | 31.3 | 35.8 | 36.6 |
| C22:6(n-3)DHA | 16.1 | 18.7 | 19.4 |
| EPA+DHA | 47.4 | 54.5 | 56 |
(3) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, the intermediate enzymolysis product and glycerol are added into a batch reactor according to the substrate molar ratio of 1:2 (intermediate enzymolysis product/glycerol), 4 wt% of Novozym 435 is added, and the reaction is carried out for 6 hours under the conditions that the temperature is 60 ℃ and the stirring speed is 800rpm, so as to obtain the diglyceride product. The composition of the resulting diglyceride product is shown in Table 14, and the composition of the n-3 long-chain polyunsaturated fatty acids as the respective components in the diglyceride product is shown in Table 15.
TABLE 14
| Glyceride composition | Content (%) |
| Triglycerides | 25.1 |
| Diglyceride | 53.3 |
| Monoglyceride | 21.6 |
Watch 15
| Triglycerides | Diglyceride | Monoglyceride | |
| C20:5(n-3)EPA | 32.1 | 35.1 | 35.8 |
| C22:6(n-3)DHA | 16.6 | 18.8 | 19.3 |
| EPA+DHA | 48.7 | 53.9 | 55.1 |
Example 4
(1) Adding squid oil and ethanol into a sealable batch reactor according to a substrate molar ratio of 1:1 (fish oil/ethanol), respectively adding 12 wt% of Lipozyme RM IM, and reacting for 12 hours at the temperature of 40 ℃ and the stirring speed of 800rpm to obtain an intermediate enzymolysis product rich in n-3 long-chain polyunsaturated fatty acid, wherein the content of diglyceride in the product is 14.2%, the content of monoglyceride in the product is 1.7%, and the content of n-3 long-chain polyunsaturated fatty acid is 41.6%.
(2) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, the intermediate enzymolysis product and glycerol are added into an intermittent reactor according to the substrate molar ratio of 1:5 (intermediate enzymolysis product/glycerol), 10 wt% of Novozym 435 is added, and the reaction is carried out for 8 hours at the temperature of 60 ℃ and the stirring speed of 600rpm, so as to obtain the monoglyceride product, wherein the monoglyceride content is 51.1%, the diglyceride content is 20.3%, and the n-3 long-chain polyunsaturated fatty acid content in the monoglyceride is 43.4%.
(3) After ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, the intermediate enzymolysis product and glycerol are added into an intermittent reactor according to the substrate molar ratio of 1:1.5 (intermediate enzymolysis product/glycerol), 10 wt% of Novozym 435 is added, and the reaction is carried out for 10 hours at the temperature of 60 ℃ and the stirring speed of 400rpm, so as to obtain the diglyceride product, wherein the content of diglyceride is 38.3%, the content of monoglyceride is 25.5%, and the content of n-3 long-chain polyunsaturated fatty acid in the diglyceride is 42.1%.
In view of the fact that the content of n-3 long-chain polyunsaturated fatty acid in glyceride prepared by the conventional method is low, the method adopts a two-step enzyme method reaction to prepare the monoglyceride or diglyceride product rich in the n-3 long-chain polyunsaturated fatty acid.
Step 1, catalyzing alcoholysis reaction of fish oil by using Lipase RM IM, Lipase TL IM or Lipase AY-30SD which is low in activity and mainly contains EPA and DHA as n-3 long-chain polyunsaturated fatty acids as catalysts to obtain an intermediate enzymolysis product with high n-3 long-chain polyunsaturated fatty acid content, wherein the n-3 long-chain polyunsaturated fatty acid content is more than 45%;
step 2, ethanol and fatty acid ethyl ester in the intermediate enzymatic product are respectively removed by reduced pressure distillation and molecular distillation, the intermediate enzymatic product is catalyzed and hydrolyzed by Novozym 435 lipase, through condition adjustment, monoglyceride or diglyceride products are respectively prepared, wherein the content of monoglyceride in the monoglyceride product is more than 65%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, the content of n-3 long-chain polyunsaturated fatty acid in the monoglyceride is more than 50%, the content of diglyceride in the diglyceride product is more than 50%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, and the content of n-3 long-chain polyunsaturated fatty acid in the diglyceride is more than 50%, so that the problem that the content of n-3 long-chain polyunsaturated fatty acid in the monoglyceride or diglyceride products prepared by the conventional method is low is solved. The inventors have further studied and found that the content of n-3 long-chain polyunsaturated fatty acids in the monoglyceride product and the diglyceride product is low when the process and conditions of the present invention are not used.
Meanwhile, as a glyceride product is generated through alcoholysis reaction in the step (1), in the reaction in the step (2), a certain amount of monoglyceride and diglyceride exist, so that emulsification can be achieved in the reaction process, and after the glycerol is added and stirred, the reaction system is changed into a microemulsion system, so that the contact area of the glycerol and the grease is increased, and the specific surface area of the lipase in play is increased, and meanwhile, due to the existence of a large number of oil-water interfaces, the lipase is favorable for opening a cover of an active center, and the lipase is favorable for playing a catalytic role, so that in the reaction in the step (2), the reaction rate is higher, and the production efficiency is greatly improved.
In conclusion, the glyceride product rich in n-3 long-chain polyunsaturated fatty acid is prepared by adopting a two-step enzyme method reaction for the first time, firstly, n-3 long-chain polyunsaturated fatty acid is enriched by utilizing the 'inertia' of lipase to n-3 long-chain polyunsaturated fatty acid through an enzyme-catalyzed alcoholysis reaction, and an intermediate enzymolysis product rich in n-3 long-chain polyunsaturated fatty acid is obtained; after ethanol and fatty acid ethyl ester are respectively removed by reduced pressure distillation and molecular distillation, the diglyceride or monoglyceride product rich in n-3 long-chain polyunsaturated fatty acid is respectively obtained by the glycerolysis reaction catalyzed by enzyme and the adjustment of conditions.
It should be noted that the above-mentioned embodiments are only for illustrating the technical solutions of the present invention and not for limiting, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, which should be covered by the claims of the present invention.
Claims (10)
1. A method for preparing long-chain polyunsaturated fatty acid glyceride rich in fish oil n-3 by an enzyme method is characterized by comprising the following steps: comprises the steps of (a) preparing a mixture of a plurality of raw materials,
enzyme catalysis alcoholysis reaction: adding fish oil and ethanol into an intermittent reactor according to a substrate molar ratio of 1: 3-9, adding 4-15 wt% of lipase, reacting for 4-12 hours at a temperature of 25-45 ℃ and a stirring speed of 300-800 rpm, and obtaining an intermediate enzymolysis product rich in n-3 long-chain polyunsaturated fatty acid, wherein the content of monoglyceride and diglyceride in the intermediate enzymolysis product is more than 30%, and the content of monoglyceride is more than 3%;
preparing monoglyceride: after ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, adding the intermediate enzymolysis product and glycerol into an intermittent reactor according to the molar ratio of 1: 3-6, adding 3-12 wt% of lipase, and reacting for 6-12 hours at the temperature of 30-70 ℃ and the stirring speed of 300-800 rpm to obtain a monoglyceride product rich in n-3 long-chain polyunsaturated fatty acids, wherein the content of the monoglyceride is more than 65%, the content of the n-3 long-chain polyunsaturated fatty acids is more than 45%, and the content of the n-3 long-chain polyunsaturated fatty acids in the monoglyceride is more than 50%;
preparing diglyceride: after ethanol and fatty acid ethyl ester of the intermediate enzymolysis product are respectively removed by adopting reduced pressure distillation and molecular distillation, adding the intermediate enzymolysis product and glycerol into an intermittent reactor according to the molar ratio of 1: 0.5-2, adding 4-14 wt% of lipase, and reacting for 6-12 hours at the temperature of 30-70 ℃ and the stirring speed of 300-800 rpm to obtain a diglyceride product rich in n-3 long-chain polyunsaturated fatty acid, wherein the content of diglyceride is more than 50%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, and the content of n-3 long-chain polyunsaturated fatty acid in diglyceride is more than 50%.
2. The enzymatic process for the preparation of fish oil-rich n-3 long chain polyunsaturated fatty acid glycerides as claimed in claim 1, wherein: the fish oil is deep sea fish oil, and the content of EPA and DHA is more than 20%.
3. The enzymatic process for the preparation of fish oil-rich n-3 long chain polyunsaturated fatty acid glycerides as claimed in claim 1, wherein: the enzyme catalyzes alcoholysis reaction, wherein the Lipase is one or more of Lipozyme RM IM, Lipozyme TLIM and Lipase AY-30 SD.
4. The enzymatic process for the preparation of fish oil-rich n-3 long chain polyunsaturated fatty acid glycerides as claimed in claim 1, wherein: the enzyme catalyzes alcoholysis reaction, wherein the content of n-3 long-chain polyunsaturated fatty acid in the intermediate enzymolysis product is more than 45%.
5. The enzymatic process for the preparation of fish oil-rich n-3 long chain polyunsaturated fatty acid glycerides as claimed in claim 1, wherein: the monoglyceride is prepared, wherein the lipase is a lipase Novozym 435.
6. The enzymatic process for the preparation of fish oil-rich n-3 long chain polyunsaturated fatty acid glycerides as claimed in claim 1, wherein: the preparation of diglyceride is described, wherein the lipase is lipase Novozym 435.
7. The enzymatic process for the preparation of fish oil-rich n-3 long chain polyunsaturated fatty acid glycerides as claimed in claim 1, wherein: the enzyme catalyzes alcoholysis reaction, wherein the molar ratio of fish oil to ethanol is 1:3, the addition amount of lipase is 15 wt%, the reaction temperature is 25 ℃, and the reaction time is 4 hours.
8. A glyceride product prepared by the method for preparing the glyceride rich in the fish oil n-3 long-chain polyunsaturated fatty acid by the enzyme method according to any one of claims 1 to 7.
9. The glyceride product obtained by the enzymatic method for preparing glyceride rich in fish oil n-3 long-chain polyunsaturated fatty acid according to claim 8, wherein: the glyceride products include monoglyceride products rich in n-3 long chain polyunsaturated fatty acids and diglyceride products rich in n-3 long chain polyunsaturated fatty acids.
10. The glyceride product obtained by the enzymatic method for preparing glyceride rich in fish oil n-3 long-chain polyunsaturated fatty acids according to claim 9, wherein: the content of monoglyceride in the monoglyceride product is more than 65%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, the content of n-3 long-chain polyunsaturated fatty acid in the monoglyceride is more than 50%, the content of diglyceride in the diglyceride product is more than 50%, the content of n-3 long-chain polyunsaturated fatty acid is more than 45%, and the content of n-3 long-chain polyunsaturated fatty acid in the diglyceride is more than 50%.
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| CN116869166A (en) * | 2023-07-24 | 2023-10-13 | 广东海洋大学 | A fish oil emulsion and its preparation method and application |
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