CN110141564A - A kind of glyceride mixture and its preparation method and application rich in polyunsaturated fatty acid - Google Patents
A kind of glyceride mixture and its preparation method and application rich in polyunsaturated fatty acid Download PDFInfo
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- CN110141564A CN110141564A CN201910489484.3A CN201910489484A CN110141564A CN 110141564 A CN110141564 A CN 110141564A CN 201910489484 A CN201910489484 A CN 201910489484A CN 110141564 A CN110141564 A CN 110141564A
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- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 69
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 19
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 4
- 229940079593 drug Drugs 0.000 claims abstract description 3
- 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 claims description 28
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 22
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 20
- 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 claims description 18
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 18
- 229960004488 linolenic acid Drugs 0.000 claims description 18
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 claims description 16
- 229940108924 conjugated linoleic acid Drugs 0.000 claims description 16
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 16
- 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 claims description 14
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 14
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 14
- 108090001060 Lipase Proteins 0.000 claims description 12
- 102000004882 Lipase Human genes 0.000 claims description 12
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 12
- 235000021342 arachidonic acid Nutrition 0.000 claims description 11
- 229940114079 arachidonic acid Drugs 0.000 claims description 11
- 235000011187 glycerol Nutrition 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 10
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 9
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims description 8
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- IJTNSXPMYKJZPR-UHFFFAOYSA-N parinaric acid Chemical compound CCC=CC=CC=CC=CCCCCCCCC(O)=O IJTNSXPMYKJZPR-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 claims description 3
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- IJTNSXPMYKJZPR-WVRBZULHSA-N alpha-parinaric acid Natural products CCC=C/C=C/C=C/C=CCCCCCCCC(=O)O IJTNSXPMYKJZPR-WVRBZULHSA-N 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical class OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 210000004369 blood Anatomy 0.000 abstract description 19
- 239000008280 blood Substances 0.000 abstract description 19
- 150000002632 lipids Chemical class 0.000 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 13
- 150000004665 fatty acids Chemical class 0.000 description 31
- 235000014113 dietary fatty acids Nutrition 0.000 description 29
- 229930195729 fatty acid Natural products 0.000 description 29
- 239000000194 fatty acid Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 24
- 241000700159 Rattus Species 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 17
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 16
- 239000003925 fat Substances 0.000 description 16
- 235000019197 fats Nutrition 0.000 description 16
- 230000001603 reducing effect Effects 0.000 description 13
- 238000000199 molecular distillation Methods 0.000 description 10
- 238000011049 filling Methods 0.000 description 9
- 210000002966 serum Anatomy 0.000 description 8
- 108010007622 LDL Lipoproteins Proteins 0.000 description 7
- 102000007330 LDL Lipoproteins Human genes 0.000 description 7
- 235000012000 cholesterol Nutrition 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 5
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 5
- 235000009508 confectionery Nutrition 0.000 description 5
- 150000001982 diacylglycerols Chemical class 0.000 description 5
- 235000021323 fish oil Nutrition 0.000 description 5
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 5
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 5
- 229960002733 gamolenic acid Drugs 0.000 description 5
- 239000004519 grease Substances 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- 208000008589 Obesity Diseases 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 235000020824 obesity Nutrition 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- -1 diglyceride Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000037356 lipid metabolism Effects 0.000 description 3
- 230000035790 physiological processes and functions Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 108010023302 HDL Cholesterol Proteins 0.000 description 2
- 101000864057 Homo sapiens Serine/threonine-protein kinase SMG1 Proteins 0.000 description 2
- 108010028554 LDL Cholesterol Proteins 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- 108010084311 Novozyme 435 Proteins 0.000 description 2
- 102100029938 Serine/threonine-protein kinase SMG1 Human genes 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229940099352 cholate Drugs 0.000 description 2
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 235000015872 dietary supplement Nutrition 0.000 description 2
- 210000002969 egg yolk Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000000232 gallbladder Anatomy 0.000 description 2
- 235000009200 high fat diet Nutrition 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 241000228147 Penicillium camemberti Species 0.000 description 1
- 235000002245 Penicillium camembertii Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000010241 blood sampling Methods 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 235000005686 eating Nutrition 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000020808 fast-food diet Nutrition 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
- A61K31/232—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having three or more double bonds, e.g. etretinate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
Abstract
The invention discloses a kind of glyceride mixture and its preparation method and application rich in polyunsaturated fatty acid, the mixture include the glyceride not less than 95% and the free fatty acid not higher than 5wt%；The content of diglyceride is 30-98wt%, content of monoglyceride 0.1-70wt%, content of triglyceride 0-5wt% in the glyceride.The composition is made of according to a certain percentage the monoglyceride of certain density polyunsaturated fatty acid and two glyceride, improve the absorptivity of polyunsaturated fatty acid, and there is more efficient reduction blood lipid, fat-reducing effect, it can be applied in the drug or health care product for preparing Weight-reducing and lipid-lowering.
Description
Technical field
The present invention is that the glyceride composition rich in unsaturated fatty acid has more efficient absorptivity, reduces blood lipid and subtract
Fertilizer efficiency fruit.
Background technique
With the rapid development of social economy, the raising of people's lives level, rhythm of life are also constantly being accelerated, people
Dietary structure have occurred huge change, the fast food diet structure of high sugar high in fat increasingly occupies most markets.This is just
Lead to crowd's abnormalities of sugar/lipid metabolism of many countries in the world, hyperlipidemia, obesity morbidity and mortality be consequently increased,
Human health is seriously affected.Carrying out, there are the research and development of the dietary supplements of fat reducing and weight reducing function to meet becoming for social development
Gesture has a good application prospect.Currently, in the market for fat, hyperlipidemic conditions dietary supplement product mainly with a left side
It revolves based on carnitine, unsaturated fatty acid etc..
Polyunsaturated fatty acid (PUFA) is generally referred to containing two or more double bonds and carbon chain lengths are 18~22
The straight chain fatty acid of a carbon atom.To human body have special physiological function common PUFA mainly have eicosapentaenoic acid (EPA),
Docosahexaenoic acid (DHA), eicosapentaenoic acid (DPA), arachidonic acid (AA), parinaric acid (SDA), α-flax
Acid (ALA), gamma-Linolenic acid (GLA), conjugate linolenic acid (CLNA), conjugated linoleic acid (CLA).A large amount of research confirms, PUFA because
With unique physiological function, there are more and more applications in functional food, medicine, field of health care products.
Existing PUFA product reducing blood lipid, fat-reducing effect be not significant, unstable, and main cause is PUFA in various product
Content is lower, and the absorptivity of PUFA is not high when eating, and is often a variety of PUFA existence form (such as fatty acid, second in product
Ester, monoglyceride, diglyceride, triglycerides, phosphatide etc.) mixing.These non-polyunsaturated fatty acid ingredients and a variety of
The mixed presence of PUFA existence form, has seriously affected the bioavailable efficiency of various PUFA, reduces the drop of correlated product
Blood lipid.
Summary of the invention
For undesirable, the unstable problems of health-care effects such as existing PUFA product reducing blood lipid, weight-reducing, the purpose of the present invention
It is to provide a kind of high and polyunsaturated fatty acid grease composition with efficient reducing blood lipid, weight losing function of PUFA absorptivity.
A kind of glyceride mixture rich in polyunsaturated fatty acid, the mixture include the glyceride not less than 95%
With the free fatty acid for being not higher than 5wt%；The content of diglyceride is 30-98wt% in the glyceride, and content of monoglyceride is
0.1-70wt%, content of triglyceride 0-5wt%.
Preferably, the ratio of sn-1,3:sn-1,2 are not less than 1:1, sn-1 in monoglyceride in the composition of diglyceride
(3): sn-2 is not less than 1:1.
Preferably, the ratio of sn-1,3:sn-1,2 are not less than 1.5:1, sn-1 in monoglyceride in the composition of diglyceride
(3): sn-2 is not less than 1.5:1.
Preferably, the polyunsaturated fatty acid is eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), 20
Carbon 5 alkene acid (DPA), arachidonic acid (AA), parinaric acid (SDA), alpha-linolenic acid (ALA), gamma-Linolenic acid (GLA),
The mixing of one or more of conjugate linolenic acid (CLNA), conjugated linoleic acid (CLA).
Preferably, ALA content is not less than 3wt% in the polyunsaturated fatty acid, and EPA content is not less than 10wt%, DHA
Content is not less than 10wt%, and DHA:EPA mass ratio is not higher than 5:1.
Preferably, wherein the content of ALA is 10-80wt%, more preferable 15-50wt%；Wherein the content of EPA is 20-
90wt%, more preferable 20-80wt%.
Preferably, the content of ethylene oxidic ester is less than 5ppm in mixture, and 3- chloro- 1, the content of 2 propylene glycol esters is less than
5ppm。
A kind of preparation method of the mixture rich in polyunsaturated fatty acid glyceride, includes the following steps: that utilization is partially sweet
Glyceride lipase Lipase G50 catalysis polyunsaturated fatty acid is synthesized with glycerine reaction containing diglyceride and monoglyceride
Mixture is centrifuged mixture, after recycling upper oil phase, is isolated to the mixture based on glyceride.
Preferably, the additive amount of lipase Lipase G50 is 1-5% in the esterification, and moisture additive amount is 0.5-
0.9%, reaction time 12-24h.
The mixture rich in polyunsaturated fatty acid glyceride is in the drug or health care product for preparing Weight-reducing and lipid-lowering
Using.
In fat or oil composition of the invention, polyunsaturated fatty acid can be single component, be also possible to a variety of PUFA
Mixing.The present invention is oriented design and control by the structure type to polyunsaturated fatty acid glyceride, utilizes PUFA
Diglyceride and monoglyceride are being taken in and are playing the synergistic effect in physiological function, while improving the lipid-lowering effect of PUFA
Make it have more significant fat-reducing effect.The fat or oil composition of polyunsaturated fatty acid can be used as a kind of diet benefit in the present invention
Fill agent, in the diet composition for not changing people, do not change the eating habit of people, while by improving lipid-metabolism, reach
The effect of reducing blood lipid, weight-reducing.The fat or oil composition existence form of polyunsaturated fatty acid of the invention is with monoglyceride and glycerol
It is that a kind of one kind different from the product of existing commercially available dopller signal or glycerol ester type is special based on diester
The aliphatic ester of structure.With ethyl ester or triglyceride type polyunsaturated fatty acid grease after human consumption absorbs how unsaturated
The position sn-2 that fatty acid is more present in glyceride is compared, monoglyceride and diglyceride warp rich in polyunsaturated fatty acid
After crossing human body digestion and absorption, when a large amount of sn-1 (3)-monoglyceride synthesizes triglycerides again in human small intestine, greatly increase
Add polyunsaturated fatty acid in the presence of (3) sn-1, shows function affect more outstanding.
Compared with prior art, the invention has the following advantages:
The composition effectively reduces internal superabundant fats and cholesterol, to reach dredging using reducing blood lipid as function basis
Blood vessel, the effect for reducing blood lipid, losing weight and reducing blood pressure；The composition can be mentioned effectively relative to existing PUFA class product
The bioavilability of high PUFA can effectively improve reducing blood lipid and the fat-reducing effect of PUFA.
Detailed description of the invention
Fig. 1 is that liver of laboratory animal HE stained slice microscope is taken pictures picture.
Specific embodiment
The present invention will be further described for embodiment, these embodiments are only used to illustrate the present invention, is not intended to limit the present invention
Range.
Embodiment 1
Using commercially available fish oil fatty acid, algae oil fatty acid, linolenic acid, conjugated linoleic acid as raw material, it is mixed in a certain ratio
(PUFA group becomes CLA 10.85%, ALA 5.41%, GLA 3.22%, CNLA 1.04%, AA 10.28%, EPA
30.15%, DPA 3.14%, DHA 31.17%).It (is derived from using partial glyceride lipase Lipase G50
Penicilliumcamembertii, purchased from Japanese amano enzyme preparation company) catalysis fatty acid synthesizes with glycerine reaction containing sweet
The mixture of oily diester and monoglyceride, the additive amount of lipase are 1%, and moisture additive amount is 0.5%.After esterification 12h,
Mixture is centrifuged, after recycling upper oil phase and fatty acid therein is separated off using molecular distillation and obtains with sweet
Grease product as main component.Diacylglycerol content after molecular distillation in product is 51.5%, and monoglyceride content is
46.0%, content of triglyceride 2.1%, free fatty acid content 0.4%.Glyceride total fatty acids composition is shown in Table 1, this is sweet
Grease product is denoted as composition 1.
Embodiment 2
Using commercially available fish oil fatty acid, conjugated linoleic acid, linolenic acid, granada seed oil fatty acid as raw material, mix by a certain percentage
(PUFA group becomes CLA 3.24%, ALA 6.01%, GLA 1.65%, CNLA 37.55%, AA 1.31%, EPA for conjunction
20.75%, DPA 2.42%, DHA 21.42%).Fatty acid and glycerol are catalyzed using partial glyceride lipase Lipase G50
Mixture of the reaction synthesis containing diglyceride and monoglyceride, the additive amount of lipase are 1%, and moisture additive amount is 0.5%.
After esterification 12h, mixture is centrifuged, is separated off after recycling upper oil phase and using molecular distillation therein
Fatty acid is obtained with glyceride product as main component.Diacylglycerol content after molecular distillation in product is 54.3%, single
Glyceride content is 42.7%, content of triglyceride 2.2%, free fatty acid content 0.7%.Glyceride total fatty acids group
At being shown in Table 1, which is denoted as composition 2.
Embodiment 3
Using commercially available fish oil fatty acid, conjugated linoleic acid, linolenic acid, granada seed oil fatty acid as raw material, mix by a certain percentage
(PUFA group becomes CLA 3.58%, ALA 5.94%, GLA 1.58%, CNLA 37.16%, AA 1.27%, EPA for conjunction
20.53%, DPA 2.37%, DHA 21.83%).Fatty acid and glycerol are catalyzed using partial glyceride lipase Lipase G50
Mixture of the reaction synthesis containing diglyceride and monoglyceride, the additive amount of lipase are 1%, and moisture additive amount is 0.5%.
After esterification 12h, mixture is centrifuged, is separated off after recycling upper oil phase and using molecular distillation therein
Fatty acid is obtained with glyceride product as main component.Diacylglycerol content after molecular distillation in product is 88.3%, single
Glyceride content is 10.4%, content of triglyceride 1.2%, free fatty acid content 0.1%.Glyceride total fatty acids group
At being shown in Table 1, which is denoted as composition 3.
Comparative example 1
Using commercially available fish oil fatty acid, algae oil fatty acid, linolenic acid, conjugated linoleic acid as raw material, it is mixed in a certain ratio
(PUFA group becomes CLA 10.42%, ALA 5.21%, GLA 3.45%, CNLA 1.14%, AA 10.26%, EPA
30.74%, DPA 3.17%, DHA 30.88%), preparation is rich in three ester of high-purity glycerol of PUFA.Utilize lipase
Novozym435 and Lipase SMG1 joint catalytic treatment fatty acid synthesizes the mixing of the glyceride containing PUFA with glycerine reaction
Mixture is centrifuged object, after recycling upper oil phase and is separated off fatty acid therein using molecular distillation and obtains
With triglycerides product as main component.Diacylglycerol content after molecular distillation in product is 3.1%, monoglyceride content
It is 1.3%, content of triglyceride 95.4%, free fatty acid content 0.2%.Glyceride total fatty acids composition is shown in Table 1, should
Glyceride product is denoted as Comparative composition 1.
Comparative example 2
Using commercially available fish oil fatty acid, conjugated linoleic acid, linolenic acid, granada seed oil fatty acid as raw material, mix by a certain percentage
(PUFA group becomes CLA 10.85%, ALA 5.41%, GLA 3.22%, CNLA 1.04%, AA 10.28%, EPA for conjunction
30.15%, DPA 3.14%, DHA 31.17%), preparation is rich in three ester of high-purity glycerol of PUFA.Utilize lipase
Novozym435 and Lipase SMG1 joint catalytic treatment fatty acid synthesizes the mixing of the glyceride containing PUFA with glycerine reaction
Mixture is centrifuged object, after recycling upper oil phase and is separated off fatty acid therein using molecular distillation and obtains
With triglycerides product as main component.Diacylglycerol content after molecular distillation in product is 2.7%, monoglyceride content
It is 1.0%, content of triglyceride 96.2%, free fatty acid content 0.1%.Glyceride total fatty acids composition is shown in Table 1, should
Glyceride product is denoted as Comparative composition 2.
Using relevant criterion method carry out fat or oil composition fatty acid compositional analysis and reducing blood lipid of the invention, weight-reducing,
The assessment of PUFA bioavilability.Fat or oil composition fatty acid compositional analysis is by " GB 5009.168-2016 food safety country mark
Fatty acid determination in quasi- food ", the results are shown in Table 1.
1 experiment of table forms table with oil fatty acid
Reducing blood lipid evaluation:
It is assessment to phase with composition 3-5 and comparison fat or oil composition 3-4, assesses the lipid-lowering effect of the composition.It will
70 SPF grades of rat 200g or so are adapted to 7 days in the environment of 23 DEG C of humidity are 55%, and basal feed is all fed during adaptation
And drinking water, free feeding.70 rats are randomly divided into 8 groups of (blank control group, model control group, embodiments after laundering period
1-3 and comparative example 1-2), every group 10, eliminate weight rat low compared with average value and ill.Wherein blank group is being tested
Period feed basal feed, remaining set feed high lipid food (78.8% basal feed, 1% cholesterol, No. 0.2%3 cholate,
10% yolk powder, 10% lard).Stomach-filling is carried out to rat daily, wherein blank control group, model control group stomach-filling 2.5mmol/
The Tween-80 solution (10mL/ (kgbw)) of L, embodiment 1-3 and comparative example 1-3 stomach-filling are molten with the Tween-80 of 2.5mmol/L
The PUFA glyceride of liquid dissolution, dosage are 2mL/ (kgbw), every group of 10 rats.With 78.8% basal feed, 1% gallbladder
Sterol, 10% lard, 10% yolk powder and cholate 3 of 0.2% are high lipid food, and continuous raising rat makes its blood
Clearing gallbladder sterol reaches 3.77 scholar 0.41mmol/L and models successfully.Stablize and feed 6 weeks i.e. after 42 days, acquires rat blood sample.Acquisition
Blood be centrifuged immediately, take upper serum to measure its total cholesterol (TC), high-density lipoprotein cholesterol (HDL-C), low-density
Lipoprotein cholesterol (LDL-C).
The analysis of 2 experimental animal physiochemical indice of table
| TG | TC | HDL | LDL | |
| Blank group | 1.22±0.83 | 2.45±1.24 | 1.41±0.28 | 0.72±0.18 |
| Model group | 1.96±0.75 | 3.81±1.35 | 1.35±0.48 | 2.10±0.33 |
| Composition 1 | 1.03±0.47 | 2.21±1.13 | 1.533±0.58 | 0.33±0.21 |
| Composition 2 | 1.12±0.61 | 2.19±1.02 | 1.514±0.75 | 0.41±0.19 |
| Composition 3 | 1.04±0.55 | 2.10±0.72 | 1.527±0.37 | 0.36±0.16 |
| Comparative composition 1 | 1.38±0.73 | 2.43±1.32 | 1.415±0.83 | 0.73±0.08 |
| Comparative composition 2 | 1.47±0.54 | 2.61±0.97 | 1.472±0.64 | 0.77±0.11 |
By animal experiment it has been observed that as can be seen from Table 2, compared with model group, embodiment 1-3 and comparative example 1-3 stomach-filling
The ratio between low-density lipoprotein content, low-density lipoprotein and hdl concentration of silkworm chrysalis grease group rat reduce obviously,
Significant difference；Compared with model group, total cholesterol is reduced in embodiment 1-3 and comparative example 1-2PUFA glyceride group rat blood serum
Obviously；Illustrate that total cholesterol level and low-density lipoprotein in High fat diet rats serum can be significantly reduced in the glyceride rich in PUFA
Bai Hanliang.Compared to the blank group, serum total cholesterol content and low-density lipoprotein in embodiment 1-3 and comparative example 1-2
Content difference is significant, illustrates High fat diet rats blood lipid can be made extensive by the PUFA glyceride composition of stomach-filling embodiment 1-3 preparation
Normal level is arrived again.Compared to comparative example 1-2, total cholesterol, low-density lipoprotein content in embodiment 1-3 stomach-filling rat blood serum
And the ratio between low-density lipoprotein and hdl concentration significant difference, illustrate that embodiment 1-3 lipid-lowering effect is considerably better than
Comparative example 1-2.Illustrate that PUFA glyceride composition of the invention has and inhibits blood total cholesterol, blood lipid, the raised work of LDL
With, and can be improved the level of serum hdl.Moreover, its function is better than corresponding reference composition.
Weight-reducing evaluation:
It is assessment to phase with composition 1-3 and comparison fat or oil composition 1-2, assesses the fat-reducing effect of the composition.SPF grades
Male SD rat, 150 ± 20g of weight maintain feed, high lipid food, are purchased from Guangdong Medical Lab Animal Center.Modeling terminates
Afterwards, obese rat is randomly divided into 7 groups, i.e. blank control group (normal group), model control group (inducing obesity mould high in fat by weight
Type group), embodiment 1-3 and comparative example 1-2 group.Rat presses dosage gastric infusion daily, and successive administration 6 weeks.Administration
Period gives maintenance feed except blank control group, remaining each group gives high lipid food.After the test, detection rat sign refers to
Mark, as a result as shown in table 3 and Fig. 1.As can be seen from Table 3, PUFA glyceride composition of the present invention compared with the control group, weight,
Fat index, obesity index are substantially reduced, and reducing effect is better than corresponding Comparative composition.Fig. 1 is shown in certain view
In wild range, fat cell number PUFA glyceride composition (A) is considerably less than model group (B), and better than corresponding comparison
Composition group (C).The above result shows that PUFA glyceride composition provided by the invention can reduce the accumulation of fat, and
Fat-reducing effect is better than the PUFA triglycerides product of existing Comparative composition.
3 each group Growth in Rats index of table and Lipid Metabolism Determination value
| Weight | Fat index | Obesity index | Liver index | |
| Control group | 443.82±14.47 | 2.91±0.67 | 27.17±0.34 | 2.74±0.11 |
| Model group | 516±28.41 | 4.51±1.67 | 34.61±0.43 | 2.76±0.63 |
| Composition 1 | 406±22.35 | 2.31±0.65 | 22.73±0.32 | 2.56±0.55 |
| Composition 2 | 387±18.46 | 2.42±0.79 | 21.87±0.46 | 2.24±0.72 |
| Composition 3 | 394±24.63 | 2.23±0.18 | 21.44±0.39 | 2.45±0.54 |
| Comparative composition 1 | 429±20.54 | 2.78±27 | 26.47±0.33 | 2.76±0.61 |
| Comparative composition 2 | 431±26.87 | 2.86±41 | 25.93±0.45 | 2.69±0.48 |
Absorptivity evaluation:
It is assessment to phase with composition 1-3 and comparison fat or oil composition 1-2, assesses the absorption effect of the PUFA of the composition
Rate.Experimental animal selects SD rat.By the not fatty maintenance feed diet raising of rat, 5 are randomly divided into after adapting to a week
Group (embodiment 1-3 and each one group of comparative example), every group 10.All animals freely feed and drink water.PUFA is sweet
Glyceride compositions carry out stomach-filling with the dosage of 1.2mg/g.The laggard end of line venous blood sampling of stomach-filling 2h measures PUFA content in blood.
Testing result see the table below 4.
PUFA content (ug/ml) in serum lipids after 4 stomach-filling 2h of table
As can be seen from Table 4, after giving rat oral gavage 2h, PUFA glyceride composition experimental group rat provided by the invention
Content of polyunsaturated fatty acid and digestibility are noticeably greater than Comparative composition group in serum, this explanation is provided by the invention
PUFA in PUFA glyceride composition has higher absorptivity.
Claims (10)
1. a kind of glyceride mixture rich in polyunsaturated fatty acid, which is characterized in that the mixture includes being not less than
95% glyceride and free fatty acid not higher than 5wt%；The content of diglyceride is 30-98wt% in the glyceride,
Content of monoglyceride is 0.1-70wt%, content of triglyceride 0-5wt%.
2. mixture according to claim 1, which is characterized in that the ratio of sn-1,3:sn-1,2 in the composition of diglyceride
Example is not less than 1:1, and sn-1 (3): sn-2 is not less than 1:1 in monoglyceride.
3. mixture according to claim 1, which is characterized in that the ratio of sn-1,3:sn-1,2 in the composition of diglyceride
Example is not less than 1.5:1, and sn-1 (3): sn-2 is not less than 1.5:1 in monoglyceride.
4. mixture according to claim 1 or 2 or 3, which is characterized in that the polyunsaturated fatty acid is 20 light dydrocarbons
Olefin(e) acid (EPA), docosahexaenoic acid (DHA), eicosapentaenoic acid (DPA), arachidonic acid (AA), parinaric acid
(SDA), one of alpha-linolenic acid (ALA), gamma-Linolenic acid (GLA), conjugate linolenic acid (CLNA), conjugated linoleic acid (CLA) or
Two or more mixing.
5. mixture according to claim 4, which is characterized in that ALA content is not less than in the polyunsaturated fatty acid
3wt%, EPA content are not less than 10wt%, and DHA content is not less than 10wt%, and DHA:EPA mass ratio is not higher than 5:1.
6. mixture according to claim 5, which is characterized in that wherein the content of ALA is 10-80wt%, preferably 15-
50wt%；Wherein the content of EPA is 20-90wt%, preferably 20-80wt%.
7. mixture according to claim 1 or 2 or 3, which is characterized in that the content of ethylene oxidic ester is less than in mixture
The content of 5ppm, 3- chloro- 1,2 propylene glycol esters are less than 5ppm.
8. a kind of preparation method of the mixture rich in polyunsaturated fatty acid glyceride, which comprises the steps of:
It is synthesized with glycerine reaction containing diglyceride and list using partial glyceride lipase Lipase G50 catalysis polyunsaturated fatty acid
The mixture of glyceride, mixture is centrifuged, and after recycling upper oil phase, is isolated to mixed based on glyceride
Close object.
9. preparation method according to claim 8, which is characterized in that lipase Lipase G50 in the esterification
Additive amount is 1-5%, and moisture additive amount is 0.5-0.9%, reaction time 12-24h.
10. mixture made from mixture described in claim 1~7 any one or claim 8 or 9 is in preparation weight-reducing drop
The drug of rouge or the application in health care product.
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| CN111172211A (en) * | 2020-03-20 | 2020-05-19 | 江南大学 | Method for preparing long-chain polyunsaturated fatty acid glyceride rich in fish oil n-3 by enzyme method and product thereof |
| WO2020244315A1 (en) * | 2019-06-06 | 2020-12-10 | 广东省农业科学院蚕业与农产品加工研究所 | Glyceride mixture rich in polyunsaturated fatty acids, preparation method therefor and application thereof |
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