CN106138026A - A kind of diglyceride fluid composition rich in punicic acid and its preparation method and application - Google Patents
A kind of diglyceride fluid composition rich in punicic acid and its preparation method and application Download PDFInfo
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Abstract
The present invention relates to a kind of diglyceride fluid composition rich in punicic acid, this diglyceride fluid composition is made up of following components by mass percentage: 55～the monoglyceride of the triglyceride of the diglyceride of 85%, 10～45%, 0.2～8% and 0.03～the residue of 9%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, punicic acid is 0.3～0.7:1 with the mass ratio of fatty acid, and described residue is free fatty and glycerol；Further relate to the preparation method of said composition and controlling body weight, the application improved in blood fat and the functional food of raising immunity and medicine.The diglyceride fluid composition rich in punicic acid in the present invention had both had the effect of weight reducing of diglyceride, also there is the effects such as the antiinflammatory of punicic acid, fat-reducing simultaneously, so that said composition can be widely used in control body weight, improve in blood fat and the functional food of raising immunity and medicine, in a word, the preparation technology of said composition is simple, low cost, has broad application prospects.
Description
Technical field
The present invention relates to applied chemistry technical field, particularly relate to a kind of diglyceride fluid composition rich in punicic acid and its preparation method and application.
Background technology
Diglyceride (Diacylglycerol) is the structured lipid that in a quasi-glycerol three-ester (Triacylglycerol), a fatty acid is optionally substituted by a hydroxyl group, it is micro constitutent and the endogenous centre of body fat metabolism of natural plant grease, it has two kinds of natural isomerss, i.e. 1,2-diglyceride and 1,3-diglyceride, as shown in Equation 1.
Formula 1 diglyceride structural representation (wherein COR, COR ' be saturated or unsaturated fatty acyl group)
7 kinds of article such as at present, finding through multinomial safety evaluation, diglyceride is harmless to human non-toxic, is regarded as " It is generally accepted safety " material by U.S. FDA, No. 18 bulletin approval triglyceride oil of ministry of Health of China in 2009 are new resource food.Although diglyceride and triglyceride can be worth and on absorbance essentially identical, but there is larger difference in they metabolism in vivo, short-term and long-term animal and human trial show, compared with the triglyceride formed containing same or similar fatty acid, 1,3-DAG has control and treats high blood triglyceride disease, obesity and the effect of complication thereof.Therefore, the edible oil rich in 1,3-DAG is possible not only to the oil for health care substituting triglyceride edible oil as healthy population, it is also possible to for obese people and the nutrition treatment of related complication crowd.
At present, the preparation method of diglyceride mainly has following several: (1) triglyceride alcoholysis method: i.e. under the catalysis of lipase, triglyceride reacts with lower alcohol, generate diglyceride and low-carbon-ester, but lipase the Novozyme 435 and Lipozyme IM that the method uses can only specific cleavage or synthesis sn-1 position or the ester bond of sn-3 position, therefore can only obtain 1,2-diglyceride.(2) partial hydrolysis, esterification process: i.e. first partial hydrolysis triglyceride obtains fatty acid, add glycerol, under the catalysis of sn-1 and sn-3 position selected fat enzyme, the fatty acid generation esterification that glycerol and partial hydrolysis obtain generates 1, 3-diglyceride, current most diglyceride includes that the EnovaTMOil that KAO. Corp. SA produces develops based on this principle, the shortcoming of the method maximum is that technological process is complicated, multistep is needed to separate, in addition the utilization rate of raw material is low, additionally need use lipase, and lipase price is higher, there is the problems such as high cost for industrial scale produces diglyceride.(3) glycerol solution: will triglyceride oil and glycerol and a kind of mix containing monocarboxylic acid or the alkali metal salt of dicarboxylic acids or alkali salt or its mixture (making catalyst), by the glycerolysis of triglyceride, prepare business, food stage 1,3-triglyceride oil, but conventional glycerol rhizolomy needs to react under the high temperature of 220～260 DEG C so that the Oxidation of triglyceride, diglyceride and fatty acid particularly unsaturated fatty acid strengthens.At present, prepare triglyceride oil to be mainly by triglyceride type oil and fat preparations such as soybean oil, Oleum Brassicae campestris, Oleum Arachidis hypogaeae semen and Semen Maydis oil, prepare diglyceride with fish oil etc. for raw material and the most also have a small amount of report, as (2010) such as Feltes prepare the diglyceride rich in n-3PUFA with lipase Novozyme 435 by triglyceride alcoholysis method；Eoma etc. (2010) synthesize the diglyceride rich in n-3PUFA with lipase RMIM and Novozyme 435 by hydrolysis, esterification process.
Conjugated fatty acid is to polyunsaturated fatty acid position and the common name of stereoisomer with conjugate double bond system, if there being a methyl between two double bonds, we can be referred to as the double bond that methyl separates, if there being multiple methyl, we term it the double bond that many methyl separate, if two double bond conjugated are together, we term it conjugated fatty acid.Conjugated fatty acid can be with the form being diene, triolefin or tetraene, the most common conjugated fatty acid is octadecadienoic acid and jeceric acid, namely conjugated linoleic acid (conjugated linoleic acid, and conjugate linolenic acid (conjugated linolenic acid, CLNA) CLA).Conjugate linolenic acid is different with configuration and have multiple isomer due to position of double bond, punicic acid (Punicic acid) has another name called trichosanic acid, because of it respectively found in Semen Granati and Seeds of Trichosanthes kirilowii, but is accredited as same material later, now it is collectively referred to as punicic acid, punicic acid is 9,11,13 double bond conjugation, 9 and 13 double bonds are configured as cis, 11 double bonds are configured as trans conjugate linolenic acid (9c, 11t, 13c CLNA).Punicic acid and 9c, 11t CLA (9,11 double bond conjugation, 9 double bonds are configured as cis, 11 double bonds are configured as trans, the most important a kind of isomer of conjugated linoleic acid) similarity be that their fatty acid chain the 9th and the 11st is all undersaturated double bond, and spatial configuration is identical.Punicic acid can be converted to 9c, 11t CLA in animal and human body, therefore can be as 9c, natural diets source (Tsuzuki etc., 2006) important for 11t CLA.
Conjugated fatty acid has the special physiological function different from conventional polyunsaturated fatty acid.It is reported, CLA has the most favourable physiological function, as improved humans and animals blood fat, and atherosclerosis, obesity, anticancer, antihypertensive effect (Rainer etc., 2004).CLA is in the whole world, and particularly American-European countries is used widely as the functional food such as fat-reducing, blood fat reducing and health product.CLA is primarily present in milk lipid, cheese and ruminant meat.But, CLA content in these foods only has about 1% (Sehat etc., 1998), and this makes it can not make the sanatory food containing CLA or medicine with the CLA that natural resources exists.The CLA of commercial is that this isomerization product generally comprises equimolar 9c, 11t-CLA and 10t, 12c-CLA (Pariza etc., 2001) and other isomers by the oily isomerization rich in oleic acid is obtained.There is the consideration of the aspects such as safety to the CLA of preparation of industrialization in consumer, CLA industrialized production Costco Wholesale is higher, and the CLA of preparation of industrialization has various isomeric forms, and is not that every kind of isomer all has the function useful to human body.
Punicic acid and 9c, the crucial difference of 11t-CLA is the 3rd undersaturated double bond of punicic acid, and punicic acid has a cis double bond the 13rd of fatty acid chain.So, punicic acid has again the feature of " polyunsaturated fatty acid ".Polyunsaturated fatty acid has important nutritive value, and triglyceride and cholesterol in humans and animals body are had useful effect, can reduce the danger of cardiovascular and cerebrovascular disease, promotes g and D.At present, polyunsaturated fatty acid is widely used in the development adding growth promoter and the intelligence promoting baby in baby food to.
Research finds that conjugate linolenic acid main isomer punicic acid has anticancer, the metabolic syndromes such as prevention and treatment obesity, improve the functions such as immunity, as United States Patent (USP) (US8258188B2) utilize punicic acid height body's immunity and treatment and with prevention of inflammation and inflammation associated metabolic syndrome such as inflammatory bowel etc., United States Patent (USP) (US 20080146664 A1) utilizes the relevant disease that punicic acid and Punica granatum L. acid esters therapy apparatus body fat too much cause, United States Patent (USP) (US 8367072 B2) utilizes the granada seed oil rich in punicic acid to be combined process treatment obesity with fucoxanthin.
Summary of the invention
First to be solved by this invention technical problem is that and provide a kind of diglyceride fluid composition rich in punicic acid for prior art.
Second to be solved by this invention technical problem is that the preparation method providing a kind of above-mentioned diglyceride fluid composition rich in punicic acid for prior art.
3rd to be solved by this invention technical problem is that the application providing a kind of above-mentioned diglyceride fluid composition rich in punicic acid for prior art.
The present invention solves the technical scheme that first technical problem used: a kind of diglyceride fluid composition rich in punicic acid, it is characterized in that, this diglyceride fluid composition is made up of following components by mass percentage: 55～the monoglyceride of the triglyceride of the diglyceride of 85%, 10～45%, 0.2～8% and 0.03～the residue of 9%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, punicic acid is 0.3～0.7:1 with the mass ratio of fatty acid, and described residue is free fatty and glycerol.
The present invention solves the technical scheme that second technical problem used: the preparation method rich in the diglyceride fluid composition of punicic acid in such scheme comprises the following steps:
The first step, the extraction of punicic acid:
(1) pretreatment: Semen Granati or Fructus Trichosanthis seed are cleaned, drain, is dried at 40～60 DEG C；
(2) punicic acid triglyceride extracts: dried Semen Granati or Fructus Trichosanthis seed obtain dry powder after pulverizing, dry powder is through solvent extraction supercritical extraction or directly colds pressing and squeezes to obtain punicic acid triglyceride crude extract, and the refine after degumming, deacidification, decolouring, deodorize, dewaxing of punicic acid triglyceride crude extract prepares punicic acid triglyceride；
(3) preparation of punicic acid: the punicic acid triglyceride prepared in described step (2) is obtained punicic acid after saponification, acidifying；
(4) purification: the punicic acid and the Punica granatum L. acid esters that step (3) are obtained are dissolved in organic solvent, is respectively the punicic acid of 95～98% by two step freeze crystallization isolated purity；
Second step, the punicic acid of said extracted and glycerol are mixed to form mixture with the ratio of 2～9:1, add lipozyme RMIM in the mixture and carry out the prepared diglyceride fluid composition crude product rich in punicic acid of enzymic catalytic reaction under vacuo, reaction temperature is 30～60 DEG C, in the response time 8～12h, described mixture is 200～500:1 with the mass ratio of lipozyme RMIM；
3rd step, to the above-mentioned prepared diglyceride fluid composition crude product rich in punicic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, uses the method for decolouring, deodorize and filtration to refine the diglyceride fluid composition rich in punicic acid needed for acquisition the most again.
As preferably, the extractant in described step (2) is one or more mixture in normal hexane, petroleum ether, ether, ethanol, methanol, chloroform, n-butyl alcohol, acetone, hexamethylene.
As preferably, described two-step crystallization method includes that first step crystallization and second step crystallize, and the crystallization temperature of this first step crystallization is 4 DEG C, and crystallization time is 8～16h, and crystallization pressure is normal pressure；The crystallization temperature of second step crystallization is-20 DEG C～-70 DEG C, and crystallisation times is 3-5 time, and each crystallization time is 8～16h, and crystallization pressure is normal pressure.
The present invention solves the 3rd technical scheme that technical problem is used: should be rich in the application in functional food and medicine of the diglyceride fluid composition of punicic acid, and described functional food and medicine are at least for controlling body weight, improving blood fat or the wherein one side improving in immunity.
Compared with prior art, it is an advantage of the current invention that: the diglyceride fluid composition rich in punicic acid in the present invention combines with punicic acid with triglyceride form, compared with conventional diglyceride product, the preventive effect to fat generation can be strengthened, thus reach to control the purpose of body weight, and said composition also has various nutritional labelings and the physiological advantages of punicic acid in addition to having the structural stability of oil, hence in so that the product prepared with said composition for active component more superiority compared with conventional products, the most both there is the effect of weight reducing of diglyceride, also there is the antiinflammatory of punicic acid simultaneously, the effects such as fat-reducing, so that said composition can be widely used in control body weight, improve in blood fat and the functional food of raising immunity and medicine.Meanwhile, in the preparation process of said composition, prepare punicic acid, abundant raw material source with Semen Granati or Fructus Trichosanthis seed for raw material, edible safety is high, and the punicic acid high purity 94～97% prepared, in a word, the preparation technology of said composition is simple, and low cost has broad application prospects.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1:
Collecting Semen Granati, pulverize to obtain dry powder 1000g after 40 DEG C of oven for drying, obtain the triglyceride crude extract of green with the petroleum ether of 5 times of volumes at less than 60 DEG C after reflux, extract, 6h, oil yield is 28.2%.Take triglyceride crude extract 50mL and add the potassium hydroxide-ethanol solution 200mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 50mL petroleum ether after adding 50mL water and remove not saponification compound; add in 6M hydrochloric acid 100mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying, then after rotary evaporation in vacuo, obtaining punicic acid crude extract.Punicic acid crude extract dissolves in ethanol, and the lower 4 DEG C of crystallization 8h of normal pressure remove satisfied fatty acid, and the ethanol solution obtained crystallizes 16h in subzero 20 DEG C the most at ambient pressure, is repeated 3 times the highly purified punicic acid of freezing and crystallizing isolated.The punicic acid using above-mentioned technique to prepare in the present embodiment reaches 97% through gas chromatographic analysis purity.
The punicic acid of said extracted and glycerol are mixed to form mixture with the ratio of 2:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in punicic acid of enzymic catalytic reaction under vacuo, reaction temperature is 30 DEG C, response time 10h, said mixture is 200:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in punicic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, then the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in punicic acid needed for acquisition.
After testing, diglyceride fluid composition rich in punicic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 55%, the triglyceride of 28%, the monoglyceride of 8% and the residue of 9%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, punicic acid is 0.3:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 2:
Collect Fructus Trichosanthis seed, the dry powder 1000g of particle diameter 0.4～0.5mm is pulverized to obtain after natural air drying under sunlight, at 30MPa, use SCF-CO 2 (the HA221-50-06 type supercritical extraction unit that Nantong city Huaan supercritical extraction unit produces) 2h under the conditions of 40 DEG C, obtaining the triglyceride crude extract (crude oil) of green at separating pressure 15MPa, separation temperature 50 DEG C, oil yield is 30.2%；Crude oil refine after degumming, deacidification, decolouring, deodorize, dewaxing prepares triglyceride.Take triglyceride crude extract 50mL and add the potassium hydroxide-ethanol solution 200mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 50mL petroleum ether after adding 50mL water and remove not saponification compound; add in 6M hydrochloric acid 100mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying, then after rotary evaporation in vacuo, obtaining punicic acid crude extract.Punicic acid crude extract dissolves in acetone, and the lower 4 DEG C of crystallization 8h of normal pressure remove satisfied fatty acid, then crystallize 8h in subzero 45 DEG C at ambient pressure, repeat more than 5 the highly purified punicic acid of freezing and crystallizing isolated.The punicic acid using above-mentioned technique to prepare in the present embodiment reaches 94% through gas chromatographic analysis purity.
The punicic acid of said extracted and glycerol are mixed to form mixture with the ratio of 9:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in punicic acid of enzymic catalytic reaction under vacuo, reaction temperature is 60 DEG C, response time 12h, said mixture is 500:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in punicic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, then the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in punicic acid needed for acquisition.
After testing, diglyceride fluid composition rich in punicic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 70%, the triglyceride of 19%, the monoglyceride of 5% and the residue of 6%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, punicic acid is 0.7:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 3:
Collecting Semen Granati, pulverize to obtain dry powder 1000g after 40 DEG C of oven for drying, obtain green punicic acid triglyceride crude extract after at room temperature extract 24h with the chloroform of 5 times of volumes and methanol mixed solution (volume ratio is as 1:1), oil yield is 29.7%.Take triglyceride crude extract 100mL and add the sodium hydroxide ethanol solution 400mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 100mL petroleum ether after adding 1000mL water and remove not saponification compound; add in 6M hydrochloric acid 200mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying; punicic acid crude extract 4 DEG C of crystallization 10h at ambient pressure remove satisfied fatty acid; crystallize 12h in subzero 40 DEG C the most at ambient pressure, be repeated 4 times the highly purified punicic acid of freezing and crystallizing isolated.The punicic acid using above-mentioned technique to prepare in the present embodiment reaches 96% through gas chromatographic analysis purity.
The punicic acid of said extracted and glycerol are mixed to form mixture with the ratio of 6:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in punicic acid of enzymic catalytic reaction under vacuo, reaction temperature is 45 DEG C, response time 8h, said mixture is 300:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in punicic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, then the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in punicic acid needed for acquisition.
After testing, diglyceride fluid composition rich in punicic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 85%, the triglyceride of 10%, the monoglyceride of 0.2% and the residue of 4.8%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, punicic acid is 0.5:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 4:
Collecting Fructus Trichosanthis seed, pulverize to obtain the dry powder 1000g of particle diameter 0.4～0.5mm, obtain punicic acid triglyceride crude extract with the petroleum ether of 5 times of volumes at less than 80 DEG C after reflux, extract, 6h under sunlight after natural air drying, oil yield is 28.8%.The refine after degumming, deacidification, decolouring, deodorize, dewaxing of punicic acid triglyceride crude extract prepares triglyceride.Take triglyceride crude extract 50mL and add the potassium hydroxide-ethanol solution 200mL of 2M 90% saponification 2h at nitrogen protects lower 60 DEG C; add three extractings of 50mL petroleum ether after adding 50mL water and remove not saponification compound; add in 6M hydrochloric acid 100mL and go to upper strata to obtain petroleum ether solution with petroleum ether extracting after acidifying, then after rotary evaporation in vacuo, obtaining punicic acid crude extract.Punicic acid crude extract dissolves in acetone, and the lower 4 DEG C of crystallization 8h of normal pressure remove satisfied fatty acid, then crystallize 8h in subzero 45 DEG C at ambient pressure, repeat more than 5 the highly purified punicic acid of freezing and crystallizing isolated.The punicic acid using above-mentioned technique to prepare in the present embodiment reaches 94% through gas chromatographic analysis purity.
The punicic acid of said extracted and glycerol are mixed to form mixture with the ratio of 4:1, add lipozyme RMIM (Novozymes Company of Denmark) in the mixture and carry out the prepared diglyceride fluid composition crude product rich in punicic acid of enzymic catalytic reaction under vacuo, reaction temperature is 40 DEG C, response time 10h, said mixture is 200:1 with the mass ratio of lipozyme RMIM.To the above-mentioned prepared diglyceride fluid composition crude product rich in punicic acid by the acid of molecular distillation fractionation of fatty and monoglyceride, then the method for decolouring, deodorize and filtration is used to refine the diglyceride fluid composition rich in punicic acid needed for acquisition.
After testing, diglyceride fluid composition rich in punicic acid prepared by the present embodiment is made up of following components in parts by weight: the diglyceride of 53.97%, the triglyceride of 45%, the monoglyceride of 1% and the residue of 0.03%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride, punicic acid is 0.4:1 with the mass ratio of fatty acid, and above-mentioned residue is free fatty and glycerol.
Embodiment 5:
5.1, rich in control action to body weight of the diglyceride fluid composition of punicic acid (Punicic acid)
Appointing to take and carried out zoopery by the diglyceride fluid composition rich in punicic acid prepared in above-described embodiment 1～4, research said composition is the most inhibited to the increase of body weight and body fat.
The male ICR mouse of 6 week old is provided by Zhejiang Province's Experimental Animal Center, and ICR mice is randomly divided into 2 groups after adapting to 7 days, often group 10.Following 6 week, 2 groups of mices are in addition to feeding feedstuff, respectively to give each mice rich in the diglyceride fluid composition of punicic acid and per os gavage of consumption of punicic acid triglyceride oil (its punicic acid content is for 78%) 50mg/kg body weight every day, measuring the body weight of each mice every two weeks, the meansigma methods of surveyed body weight is as shown in table 1.As it can be seen from table 1 compared with punicic acid triglyceride line of oils, Mouse Weight can be significantly inhibited rich in the diglyceride fluid composition of punicic acid and gather way, control the growth of body weight.
Table 1 is rich in the impact on Mouse Weight of the diglyceride fluid composition of punicic acid
5.2, the impact on blood fat
Appointing to take and carried out zoopery by the diglyceride fluid composition rich in punicic acid prepared in above-described embodiment 1～4, whether research said composition has improvement result to blood fat.
The male ICR mouse of 6 week old is provided by Zhejiang Province's Experimental Animal Center, and ICR mice is randomly divided into 2 groups after adapting to 7 days, often group 10.Following 6 week, 2 groups of mices are in addition to feeding feedstuff, respectively to give each mice rich in the diglyceride fluid composition of punicic acid and per os gavage of consumption of punicic acid triglyceride oil (its punicic acid content is for 78%) 50mg/kg body weight every day, experiment takes snow and measures lipid of mice after terminating.The meansigma methods of surveyed blood fat is as shown in table 2.As can be seen from Table 2, compared with punicic acid triglyceride line of oils, diglyceride fluid composition rich in punicic acid can significantly improve mice HDL-C content (HDL-C), reduce low-density lipoprotein cholesterol (LDL-C) content, improving the ratio of LDL-C Yu HDL-C, this shows to significantly improve lipid of mice rich in the diglyceride fluid composition of punicic acid.
Table 2 is rich in the impact on lipid of mice of the diglyceride fluid composition of punicic acid
Claims (5)
1. the diglyceride fluid composition rich in punicic acid, it is characterised in that this diglyceride fluid composition presses matter
Amount percent meter is made up of following components: 55～the glycerol of the triglyceride of the diglyceride of 85%, 10～45%, 0.2～8%
One ester and 0.03～the residue of 9%, in the whole glyceride being made up of above-mentioned monoglyceride, diglyceride and triglyceride
Punicic acid is 0.3～0.7:1 with the mass ratio of fatty acid, and described residue is free fatty and glycerol.
2. a preparation method for the diglyceride fluid composition rich in punicic acid as claimed in claim 1, its feature
It is to comprise the following steps: the first step, the extraction of punicic acid:
(1) pretreatment: Semen Granati or Fructus Trichosanthis seed are cleaned, drain, is dried at 40～60 DEG C；
(2) punicic acid triglyceride extracts: dried Semen Granati or Fructus Trichosanthis seed obtain dry powder after pulverizing, and dry powder is through solvent
Extraction, supercritical extraction or directly cold pressing and squeeze to obtain punicic acid triglyceride crude extract, punicic acid triglyceride crude extract warp
After degumming, deacidification, decolouring, deodorize, dewaxing, refine prepares punicic acid triglyceride；
(3) preparation of punicic acid: the punicic acid triglyceride prepared in described step (2) is obtained after saponification, acidifying
To punicic acid；
(4) purification: the punicic acid and the Punica granatum L. acid esters that step (3) are obtained are dissolved in organic solvent, freezing by two steps
Crystallization process isolated purity is respectively the punicic acid of 94～97%；
Second step, is mixed to form mixture with the ratio of 2～9:1, at this mixture by the punicic acid of said extracted and glycerol
Middle addition lipozyme RMIM carries out enzymic catalytic reaction under vacuo and prepares the diglyceride fluid composition rich in punicic acid
Crude product, reaction temperature is 30～60 DEG C, the response time 8～12h, described mixture and the mass ratio of lipozyme RMIM
It is 200～500:1；
3rd step, to the above-mentioned prepared diglyceride fluid composition crude product rich in punicic acid by molecular distillation fractionation of fatty
Acid and monoglyceride, then use the method for decolouring, deodorize and filtration to refine the diglyceride rich in punicic acid needed for acquisition
Fluid composition.
3. the preparation method of the diglyceride fluid composition rich in punicic acid as claimed in claim 2, it is characterised in that
Extractant in described step (2) be normal hexane, petroleum ether, ether, ethanol, methanol, chloroform, n-butyl alcohol,
One or more mixture in acetone, hexamethylene.
4. the preparation method of the diglyceride fluid composition rich in punicic acid as claimed in claim 2, it is characterised in that
Described two-step crystallization method includes that first step crystallization and second step crystallize, and the crystallization temperature of this first step crystallization is 4 DEG C, crystallization
Time is 8～16h, and crystallization pressure is normal pressure；The crystallization temperature of second step crystallization is-20 DEG C～-70 DEG C, and crystallisation times is 3-5
Secondary, each crystallization time is 8～16h, and crystallization pressure is normal pressure.
5. the diglyceride fluid composition rich in punicic acid as claimed in claim 1 is in functional food and medicine
Application, described functional food and medicine are at least for controlling body weight, improving blood fat or improve the wherein side in immunity
Face.
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| CN106822081A (en) * | 2016-12-30 | 2017-06-13 | 浙江海洋大学 | A kind of phosphatide type punicic acid fat or oil composition and its preparation method and application |
| CN116077422A (en) * | 2023-01-04 | 2023-05-09 | 成都大学 | Pomegranate seed oil diglyceride nanoemulsion gel |
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| CN101033188A (en) * | 2007-03-26 | 2007-09-12 | 浙江大学 | Method of preparing punicic acid, its salt and ester |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106822081A (en) * | 2016-12-30 | 2017-06-13 | 浙江海洋大学 | A kind of phosphatide type punicic acid fat or oil composition and its preparation method and application |
| CN116077422A (en) * | 2023-01-04 | 2023-05-09 | 成都大学 | Pomegranate seed oil diglyceride nanoemulsion gel |
| CN116077422B (en) * | 2023-01-04 | 2024-02-13 | 成都大学 | Pomegranate seed oil diglyceride nanoemulsion gel |
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