CN111838676A - Medium-long chain fatty acid grease rich in 1, 3-dilaurate-2-palmitic acid triglyceride and preparation and application thereof - Google Patents
Medium-long chain fatty acid grease rich in 1, 3-dilaurate-2-palmitic acid triglyceride and preparation and application thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
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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
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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Abstract
The application discloses medium-long chain fatty acid grease rich in 1, 3-dilauric acid-2-palmitic acid triglyceride and preparation and application thereof, wherein the preparation method comprises the following steps: carrying out acidolysis reaction by using lauric acid and palm stearin as substrates and sn-1, 3-position specific lipase as a catalyst, and removing the catalyst and free fatty acid after the reaction is finished to obtain the medium-long-chain fatty acid oil, wherein the content of 1, 3-dilauric acid-2-palmitic acid triglyceride in the medium-long-chain fatty acid oil is 20-40%. The medium-long chain fatty acid grease rich in 1, 3-dilaurate-2-palmitic acid triglyceride is applied to weight increment of special people or animals.
Description
Technical Field
The invention relates to the field of biological manufacturing of functional oil, in particular to a preparation method and application of medium-long-chain fatty acid oil rich in 1, 3-dilaurate-2-palmitic acid triglyceride.
Background
The oil and fat is an important component of food, the chemical structure of the oil and fat is mainly ester formed by glycerol and fatty acid, and the oil and fat is one of indispensable nutrient elements for organisms and has the advantages of providing energy for the organisms and playing a special health role. The metabolism is influenced by the difference of the types and the positions of fatty acids in triglyceride, medium-chain fatty acid lipid (MCT) is metabolized faster than long-chain fatty acid Lipid (LCT), MCT can be hydrolyzed rapidly and enters portal vein to be absorbed, LCT is hydrolyzed slowly and needs to be combined with chylomicron to be transported into a circulatory system to be absorbed through a lymphatic system. The MLM (Middle-long-chain-like) in the medium-long-chain fatty acid grease can take the metabolic and functional advantages of medium-chain fatty acid and long-chain fatty acid into consideration, on one hand, the long-chain fatty acid provides more energy for organisms, and fat accumulation cannot be caused by the presence of the medium-chain fatty acid, and on the other hand, the MLM is faster in metabolism than LCT and can supply energy quickly. Therefore, the type also becomes a main research and development direction of medium-long chain fatty acid grease.
Different kinds of fatty acids have different benefits in human metabolism, such as the benefits of long-chain fatty acids EPA, DHA on cardiovascular and cerebrovascular vessels, and the improvement of short-chain fatty acid butyric acid on the intestinal health of animals. Lauric acid is a specific fatty acid, the carbon chain of which is the longest in medium-chain fatty acids, and although it is a saturated fatty acid, it is not at risk for cardiovascular disease like other long-chain saturated fatty acids. Lauric acid is mainly derived from coconut oil, and accounts for about 50% of fatty acids. Research shows that coconut oil has good health function, and coconut oil is used as a main source of dietary fat in some areas such as south Asia, and the risk of cardiovascular diseases is reduced. Lauric acid also has some special functions, such as bacteriostasis, antiphlogosis, etc. In addition, on one hand, MCT rich in lauric acid is introduced into the market, is used for nutrition supplement or cooking, has a good health function, and on the other hand, compared with medium-long-chain fatty acid oil synthesized by traditional caprylic acid and capric acid, the novel medium-long-chain fatty acid oil rich in lauric acid has a higher smoke point and a wider application range. These studies indicate that lauric acid has a unique advantage as a medium-chain fatty acid in synthesizing a medium-long-chain fatty acid.
Breast milk is an important food required in the growth and development process of infants, about 20% of palmitic acid exists in human milk, and the palmitic acid is mainly located at sn-2 position of triglyceride in human milk, and researches show that the structure has more benefits for infants. Furthermore, lauric acid (4.73%) is present in human milk more than caprylic acid (0.16%) and capric acid (1.23%), which also highlights the nutritional value of lauric acid. In conclusion, the MLCT rich in 1, 3-dilaurate-2-palmitic acid triglyceride contains more medium-chain fatty acid lauric acid in breast milk on one hand and more Sn-2-palmitic acid on the other hand, so that the grease has better application value.
The most common mode for relatively late research on MLCT in China is an ester interchange method of MCT and LCT, and although the method has high efficiency and raw material utilization rate, the obtained product fatty acid cannot ensure a specific site, and only the doping rate of medium-chain fatty acid in LCT is simply pursued. With the intensive research on functional oil, the structural lipid meets the requirements of common consumers and concerns the requirements of special people, such as infants, hospital patients and the like, and in order to meet the requirements, products with special structures and functions need to be designed, so that the traditional medium-long chain fatty acid oil has certain limitations. At present, medium-long chain fatty acid grease with specific structure and function is not rich in on the market. The invention application document CN109666541A discloses a preparation method of high-purity medium-long chain fatty acid grease, which is to synthesize a target product by utilizing the enzymatic transesterification reaction of octyl/decanoic acid MCT and long-chain fatty acid triglyceride. Although the target product with high medium-chain fatty acid incorporation rate can be obtained by the method, the fatty acid in the target product has no specific site, and triglyceride molecules have no special structure, so that the nutrition and health functions have certain limitation, and meanwhile, lauric acid is not involved in the invention. The invention application document CN103897811A also discloses a method for producing medium-long chain fatty acid grease, which comprises the step of carrying out ester interchange reaction on medium-chain fatty acid triglyceride with 6-12 carbons and long-chain fatty acid triglyceride with 16-24 carbons, so as to achieve the effect that the medium-chain fatty acid and the long-chain fatty acid are positioned on the same triglyceride molecule, and has similar limitations to the method mentioned in the above patent. The invention patent publication CN105104583B discloses a preparation method of medium-long chain fatty acid oil, which relates to a method for synthesizing a target product by catalyzing edible oil to react with medium-chain fatty acids (including caprylic acid, capric acid and lauric acid) by using a solid acid catalyst. The solid acid catalyst has no site specificity, the method does not pursue the insertion of specific medium-chain fatty acid into a specific site, the raw material edible oil has no distinct characteristics, and the synthesized target product does not have the characteristic of being rich in 1, 3-dilaurate-2-palmitic acid triglyceride.
Disclosure of Invention
In order to solve the limitation of the traditional medium-long-chain fatty acid grease and obtain the medium-long-chain fatty acid grease with special structure and function, the invention provides a preparation method of the medium-long-chain fatty acid grease rich in 1, 3-dilauric acid-2-palmitic acid triglyceride for the first time.
The preparation method of the medium-long chain fatty acid grease rich in 1, 3-dilaurate-2-palmitic acid triglyceride comprises the following steps:
carrying out acidolysis reaction by using lauric acid and palm stearin as substrates and sn-1, 3-position specific lipase as a catalyst, and removing the catalyst and free fatty acid after the reaction is finished to obtain the medium-long-chain fatty acid grease, wherein the content of 1, 3-dilauric acid-2-palmitic acid triglyceride in the medium-long-chain fatty acid grease is 20-40%.
Several alternatives are provided below, but not as an additional limitation to the above general solution, but merely as a further addition or preference, each alternative being combinable individually for the above general solution or among several alternatives without technical or logical contradictions.
Optionally, the molar ratio of the palm stearin to the lauric acid is 1: 4-12
Optionally, the dosage of the catalyst is 4-12% of the total mass of the substrate
Optionally, the reaction temperature of the acidolysis reaction is 50-65 ℃; the reaction time is 1-16 h.
Optionally, the acidolysis reaction is carried out under the protection of inert gas or under the vacuum condition that the air residual pressure is less than 90mm Hg. The inert gas may be nitrogen, helium, or the like.
Alternatively, the sn-1,3 position specific lipase may be a commercially available lipase, such as TL lipase, RM lipase, or a lipase derived from a microorganism and having such a property.
The content of the sn-2-palmitic acid of the palm stearin is more than or equal to 50 percent. The purity of the used lauric acid is more than or equal to 98 percent, and the lauric acid is preferentially used in food grade.
Optionally, the method for removing free fatty acids comprises: distilling or neutralizing, extracting and deacidifying.
The application also provides the application of the medium-long chain fatty acid grease rich in 1, 3-dilauric acid-2-palmitic acid triglyceride in weight increment of special people or animals.
Alternatively, the application can refer to the use of medium-long chain fatty acid grease rich in 1, 3-dilaurate-2-palmitic acid triglyceride as a weighting agent for special people or animals. The special population can be infants or other people needing weight gain, and the animals can be poultry, livestock, aquatic products and the like.
The target product medium-long-chain fatty acid oil is triglyceride with more structural and functional advantages, and the preparation method has the advantages of low raw material price, mild process conditions, low reaction condition requirement and low energy consumption. The target grease has a plurality of brand-new triglyceride molecular structures, has good application value, and has the effect of remarkably promoting the weight gain of organisms through the safety and the functionality of animal experiment evaluation, and abnormal lipid metabolism and insignificant inflammatory reaction are often generated along with the weight gain.
Drawings
FIG. 1 is a mass spectrum of 1, 3-dilauric acid-2-palmitic acid triglyceride.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.
Example 1
(1) Adding 5.0g of palm stearin and 12.12g of lauric acid (the molar ratio is 1:10) into a 100ml round bottom flask, filling nitrogen, covering a turning plug, placing the flask in a constant-temperature water bath oscillator at 65 ℃ for a period of time, adding 1.712g (w/w is 10%) of AO IM lipase (provided by Hangzhou Kangyuan food science and technology Co., Ltd.) after reaction substrates are uniformly mixed and are in a liquid state, filling nitrogen for protection, covering the turning plug, and reacting for 2.5 hours under the condition of 200 r/min.
(2) And after the reaction is finished, filtering to remove the immobilized enzyme, collecting the mixed material, neutralizing free fatty acid by using KOH, extracting glyceride by using n-hexane, and distilling to remove the n-hexane to obtain the target product. The content of 1, 3-dilauric-2-palmitic acid triglyceride in the obtained product was 39.59% as determined by GC.
The mass spectrum of 1, 3-dilauric acid-2-palmitic acid triglyceride is shown in figure 1, the triglyceride generally has 4 fragment ions in the mass spectrum, namely RCO, M-RCOO, RCO +74 and RCO +128 ions, the RCO corresponds to acyl ions, the spectrum has only two, and the M/z is 183 and 239, and the lauric acid and the palmitic acid correspond to each other. M-RCOO is a diglyceride ion, M/z is 439 and 495 and corresponds to 24-and 26-carbon diglyceride, RCO +74 and RCO +128 ions correspond to the acyl ions, and M/z is 257, 313, 311 and 367 and corresponds to lauric acid and palmitic acid. From these 8 characteristic ions, it was confirmed that the triglyceride contained 2-lauric acid and 1-palmitic acid, and since the enzyme used was a sn-1, 3-specific lipase and the influence of acyl group migration was small, the majority of the triglyceride was 1, 3-dilauric acid-2-palmitic acid.
GC assay conditions (same as in the following examples): agilent 7890A-5975C, chromatographic column: DB-1HT,15 m.times.0.25 mm.times.0.10 μm; sample inlet temperature: 320 ℃; sample introduction amount: 1 mu L of the solution; the split ratio is as follows: 10: 1; constant flow mode, column flow rate: 1 mL/min; column temperature procedure: heating to 350 deg.C at 200 deg.C/min, and maintaining for 5 min; mass spectrum conditions: an ion source: EI; ion source temperature: 300 ℃; quadrupole temperature: 200 ℃; mass number scan range: 33-1000 amu.
Table 1 shows medium-long chain fatty acid oil with different 1, 3-dilaurate-2-palmitic acid triglyceride contents obtained by using the enzyme under different conditions:
TABLE 1
Example 2
(1) Adding 5.0g of palm stearin and 9.7g of lauric acid (the molar ratio is 1:8) into a 100ml round-bottom flask, filling nitrogen, covering a flanging plug, placing the flask in a constant-temperature water bath oscillator at 60 ℃ for a period of time, adding 1.178g of RM IM lipase (w/w is 8%) after reaction substrates are uniformly mixed and are in a liquid state, then filling nitrogen for protection, covering the flanging plug, and reacting for 7 hours at the speed of 200 r/min.
(2) And after the reaction is finished, filtering to remove the immobilized enzyme, collecting the mixed material, neutralizing free fatty acid by using KOH, extracting glyceride by using n-hexane, and distilling to remove the n-hexane to obtain the target product. The content of 1, 3-dilauric-2-palmitic acid triglyceride in the obtained product was 31.76% as determined by GC.
Example 3(1) into a 100ml round bottom flask were added 5.0g of palm stearin and 9.7g of lauric acid (molar ratio 1:8), nitrogen was introduced, a tip-off plug was closed, the flask was placed in a 60 ℃ constant temperature water bath oscillator for a while, after the substrates were uniformly mixed and in a liquid state, 1.178g of TL IM lipase (w/w: 8%) was added, and the flask was then purged with nitrogen and then covered with a tip-off plug to react for 16 hours at 200 r/min.
(2) And after the reaction is finished, filtering to remove the immobilized enzyme, collecting the mixed material, neutralizing free fatty acid by using KOH, extracting glyceride by using n-hexane, and distilling to remove the n-hexane to obtain the target product. The content of 1, 3-dilauric acid-2-palmitic acid triglyceride in the obtained product was 24% as determined by GC.
Example 4
(1) Adding 5.0g of palm stearin and 9.7g of lauric acid (the molar ratio is 1:8) into a 100ml round-bottom flask, filling nitrogen, covering a turning plug, placing the flask in a constant-temperature water bath oscillator at 50 ℃ for a period of time, adding 1.178g of Lpase DF (manufactured by Amano, Japan) lipase (w/w is 8 percent) after reaction substrates are uniformly mixed and are in a liquid state, covering the turning plug, vacuumizing and protecting, and reacting for 5 hours under the condition of 200 r/min.
(2) After the reaction is finished, carrying out centrifugation to remove lipase, collecting the mixed material, neutralizing free fatty acid by using KOH, extracting glyceride by using n-hexane, and distilling to remove the n-hexane to obtain a target product. The content of 1, 3-dilaurate-2-palmitic acid triglyceride was 36.83% as determined by GC.
Example 5
Safety and functionality assessment test
The test method comprises the following steps: medium-long chain fatty acid oil with 39.59% of 1, 3-dilaurate-2-palmitic acid triglyceride content is selected as the test oil. 60 healthy C57BL/6 mice (20 g. + -.1 g) were randomized into 4 groups: the high fat group (HFD), the palm stearin group (PS), the medium-long chain fatty acid fat group (MLCT) and the normal feed group (NCD), wherein the HFD is the feed group containing 20.68% of lard oil, the fat energy ratio is 45%, the PS and MLCT groups are experimental groups for half replacing the lard oil by unmodified palm stearin and synthesized medium-long chain fatty acid fat respectively, the former three groups are all high fat groups, and the NCD group is the normal feed group with the fat energy ratio of 10%. Each group of mice was fed the corresponding feed for a total of 10 weeks.
Weekly body weight and food intake of mice were recorded, after 10 weeks all animals were fasted for 16h, bled from the orbit, and centrifuged to obtain mouse serum. Serum Total Cholesterol (TC), high density lipoprotein cholesterol (HDL-C), Leptin (LEP) levels, as well as Lipopolysaccharide (LPS), Lipopolysaccharide Binding Protein (LBP), alkaline phosphatase (ALP) levels were measured in mice and the results are shown in Table 2.
Table 2 safety and functionality evaluation test results
| Group of | HFD | PS | MLCT | NCD |
| Body weight growth ratio (%) | 161.58±4.21b | 156.98±2.56bc | 178.47±4.01a | 145.59±1.69c |
| Total energy intake (Kj) | 113.74±1.82a | 117.53±8.32a | 111.96±6.61a | 115.21±5.61a |
| TC(mmol/L) | 5.91±0.34a | 6.05±0.31a | 6.54±0.34a | 4.78±0.13b |
| HDL-C(mmol/L) | 2.83±0.08a | 2.72±0.06a | 2.63±0.09a | 2.22±0.03b |
| LEP(pg/ml) | 285.30±13.88a | 306.90±13.25a | 285.20±11.29a | 272.40±7.18a |
| LPS(ng/ml) | 18.54±0.50a | 19.10±0.58a | 17.78±0.59a | 17.73±0.68a |
| LBP(ng/ml) | 2.67±0.09ab | 2.82±0.06a | 2.78±0.05ab | 2.57±0.07b |
| ALP(pg/ml) | 124.60±5.66a | 131.60±6.21a | 139.00±5.24a | 130.20±4.26a |
Note: the different letters in each column represent significant differences P <0.05
From the above data, the HFD group and MLCT group showed significantly higher body weight average than NCD; the weight gain effect of the prepared MLCT product is obviously higher than that of an HFD control group, and simultaneously, the TC and the HDL-C are not obviously different. There were no significant differences in the 4 groups with respect to inflammatory factors. Therefore, the product has better weight gain effect than lard oil, and has no significant difference in energy intake and no significant difference in blood fat and inflammatory factors. Meanwhile, the product shows obvious weight gain compared with unmodified palm stearin, but TC and HDL-C have no obvious difference, and the product synthesized by doping the palm stearin with lauric acid at a fixed point is proved to have a new function.
In conclusion, the prepared structured lipid has a good weight-gaining effect, particularly has a weight-gaining effect more obvious than that of lard, does not have a weight-losing effect caused by shortening of fatty acid chains, does not have a remarkable change in some physiological indexes caused by weight gaining compared with lard, and can be applied to the aspects of rapid energy supply, weight gaining and the like of organisms.
The above-mentioned embodiments only express several embodiments of the present application, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the concept of the present application, which falls within the scope of protection of the present application. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (8)
1. The preparation method of the medium-long chain fatty acid grease rich in 1, 3-dilaurate-2-palmitic acid triglyceride is characterized by comprising the following steps:
carrying out acidolysis reaction by using lauric acid and palm stearin as substrates and sn-1, 3-position specific lipase as a catalyst, and removing the catalyst and free fatty acid after the reaction is finished to obtain the medium-long-chain fatty acid oil, wherein the content of 1, 3-dilauric acid-2-palmitic acid triglyceride in the medium-long-chain fatty acid oil is 20-40%.
2. The preparation method according to claim 1, wherein the molar ratio of the palm stearin to the lauric acid is 1: 4-12.
3. The process according to claim 1, wherein the catalyst is used in an amount of 4 to 12% by mass based on the total mass of the substrate.
4. The method according to claim 1, wherein the reaction temperature of the acidolysis reaction is 50 to 65 ℃; the reaction time is 1-16 h.
5. The method as claimed in claim 1, wherein the acidolysis is carried out under an inert gas atmosphere or under a vacuum with an air residual pressure of less than 90mm Hg.
6. The medium-long chain fatty acid oil rich in 1, 3-dilaurate-2-palmitic acid triglyceride prepared by the preparation method according to any one of claims 1 to 5.
7. The use of medium-long chain fatty acid lipids according to claim 6 for weight gain in specific populations or animals.
8. The use according to claim 7, wherein the medium-long chain fatty acid oil is used as a weighting agent for a specific population or animal.
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| CN113229369A (en) * | 2021-04-26 | 2021-08-10 | 澳优乳业（中国）有限公司 | sn-2 saturated fatty acid active structured lipid composition and preparation method and application thereof |
| CN113755538A (en) * | 2021-09-14 | 2021-12-07 | 杭州龙宇生物科技有限公司 | Preparation and application of dilauryl glyceride rich in monobutyric acid |
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| CN113229369A (en) * | 2021-04-26 | 2021-08-10 | 澳优乳业（中国）有限公司 | sn-2 saturated fatty acid active structured lipid composition and preparation method and application thereof |
| CN113755538A (en) * | 2021-09-14 | 2021-12-07 | 杭州龙宇生物科技有限公司 | Preparation and application of dilauryl glyceride rich in monobutyric acid |
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