CN106822081A - A kind of phosphatide type punicic acid fat or oil composition and its preparation method and application - Google Patents
A kind of phosphatide type punicic acid fat or oil composition and its preparation method and application Download PDFInfo
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- CN106822081A CN106822081A CN201611251171.7A CN201611251171A CN106822081A CN 106822081 A CN106822081 A CN 106822081A CN 201611251171 A CN201611251171 A CN 201611251171A CN 106822081 A CN106822081 A CN 106822081A
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- Prior art keywords
- acid
- pomegranate
- punicic
- punicic acid
- fat
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- CUXYLFPMQMFGPL-BGDVVUGTSA-N (9Z,11E,13Z)-octadecatrienoic acid Chemical compound CCCC\C=C/C=C/C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-BGDVVUGTSA-N 0.000 title claims abstract description 205
- CUXYLFPMQMFGPL-UYWAGRGNSA-N trichosanic acid Natural products CCCCC=C/C=C/C=CCCCCCCCC(=O)O CUXYLFPMQMFGPL-UYWAGRGNSA-N 0.000 title claims abstract description 103
- 239000000203 mixture Substances 0.000 title claims abstract description 93
- 238000002360 preparation method Methods 0.000 title claims abstract description 32
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 177
- 239000002253 acid Substances 0.000 claims abstract description 105
- 241000219991 Lythraceae Species 0.000 claims abstract description 92
- 235000014360 Punica granatum Nutrition 0.000 claims abstract description 92
- 235000011187 glycerol Nutrition 0.000 claims abstract description 70
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 26
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000008280 blood Substances 0.000 claims abstract description 16
- 210000004369 blood Anatomy 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- 230000037396 body weight Effects 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 11
- 235000013376 functional food Nutrition 0.000 claims abstract description 11
- 230000036039 immunity Effects 0.000 claims abstract description 10
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 7
- 230000006872 improvement Effects 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims description 50
- 238000002425 crystallisation Methods 0.000 claims description 49
- 230000008025 crystallization Effects 0.000 claims description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 108010048733 Lipozyme Proteins 0.000 claims description 11
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 9
- 238000004332 deodorization Methods 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 9
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 238000006555 catalytic reaction Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 240000006023 Trichosanthes kirilowii Species 0.000 claims description 6
- 235000009818 Trichosanthes kirilowii Nutrition 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 claims description 5
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 claims description 5
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 5
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 5
- 235000008326 Trichosanthes anguina Nutrition 0.000 claims description 5
- 244000078912 Trichosanthes cucumerina Species 0.000 claims description 5
- 235000013399 edible fruits Nutrition 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000005194 fractionation Methods 0.000 claims description 5
- 229930007503 menthone Natural products 0.000 claims description 5
- 238000000199 molecular distillation Methods 0.000 claims description 5
- 238000003825 pressing Methods 0.000 claims description 5
- 238000007670 refining Methods 0.000 claims description 5
- 235000021283 resveratrol Nutrition 0.000 claims description 5
- 229940016667 resveratrol Drugs 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004970 Chain extender Substances 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 238000005189 flocculation Methods 0.000 claims description 4
- 230000016615 flocculation Effects 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 4
- -1 diglyceride Chemical compound 0.000 claims description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 16
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 235000019197 fats Nutrition 0.000 description 46
- 239000003921 oil Substances 0.000 description 43
- 235000019198 oils Nutrition 0.000 description 43
- 238000000034 method Methods 0.000 description 14
- 241000699666 Mus <mouse, genus> Species 0.000 description 11
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 10
- 150000002632 lipids Chemical class 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 5
- 239000004367 Lipase Substances 0.000 description 5
- 102000004882 Lipase Human genes 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000287 crude extract Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 4
- 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 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229960004488 linolenic acid Drugs 0.000 description 4
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 108010028554 LDL Cholesterol Proteins 0.000 description 3
- 108010084311 Novozyme 435 Proteins 0.000 description 3
- 241000030538 Thecla Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 231100000957 no side effect Toxicity 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 125000003473 lipid group Chemical group 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 102000015779 HDL Lipoproteins Human genes 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940108924 conjugated linoleic acid Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009329 sexual behaviour Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000005672 tetraenes Chemical class 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Edible Oils And Fats (AREA)
Abstract
The present invention provides a kind of phosphatide type punicic acid fat or oil composition and its preparation method and application, is made up of following component by mass percentage：55 ~ 85% diglyceride, 10 ~ 45% triglycerides, 0.2 ~ 8% monoglyceride and 0.03 ~ 9% residue, the mass ratio of punicic acid and aliphatic acid is 0.3 ~ 0.7 in the whole glyceride be made up of above-mentioned monoglyceride, diglyceride and triglycerides:1, residue is free fatty and glycerine.Further relate to the use of the preparation method and composition of this composition in functional food and medicine.The phosphatide type pomegranate acid composition prepared in the present invention had both had the effect of weight reducing of diglyceride, also there is the effects such as anti-inflammatory, fat-reducing of punicic acid simultaneously, so that this composition eats in the functional food and medicine of control body weight, improvement blood fat and enhance immunity, in a word, the preparation process is simple of this composition, low cost, has broad application prospects.
Description
Technical field
The present invention relates to applied chemistry technical field, more particularly to a kind of phosphatide type punicic acid fat or oil composition and its preparation
Methods and applications.
Background technology
Diglyceride（Diacylglycerol）It is a quasi-glycerol three-ester（Triacylglycerol）In an aliphatic acid quilt
The structured lipid of hydroxyl substitution, is the endogenous centre of micro constitutent and the body fat metabolism of natural plant grease, and it has two
Plant natural isomer, i.e. 1,2- diglycerides and 1,3-DAG
At present, found through multinomial safety evaluation, diglyceride is nontoxic to human body, regarded as by U.S. FDA " general public
Recognize safety " material, it is new resource food that No. 18 bulletin of ministry of Health of China in 2009 ratifies 7 kinds of articles such as triglyceride oil.To the greatest extent
Pipe diglyceride and triglycerides can be worth and absorptivity on it is essentially identical, but there is larger difference in their metabolism in vivo
Different, short-term and long-term animal and human trial shows, compared with the triglycerides constituted containing same or similar aliphatic acid, 1,
3- diglycerides have control and treat the effect of blood triglyceride disease high, obesity and its complication.Therefore, it is sweet rich in 1,3-
The edible oil of oily diester can not only substitute for health care oil of the triglyceride edible oil as healthy population, it is also possible to for obesity
Crowd and the nutrition treatment of related complication crowd.
At present, the preparation method of diglyceride mainly has following several：（1）Triglycerides alcoholysis method：I.e. in lipase
Under catalysis, triglycerides reacts with lower alcohol, generates diglyceride and low-carbon-ester, but the lipase that the method is used
Novozyme 435 and Lipozyme IM can only specific cleavage or the synthesis ester bond of sn-1 or sn-3, therefore can only obtain
To 1,2- diglycerides.（2）Partial hydrolysis, esterification process：I.e. first partial hydrolysis triglycerides obtains aliphatic acid, adds glycerine,
Under the sn-1 and sn-3 catalysis of selected fat enzyme, there is esterification generation in the aliphatic acid that glycerine is obtained with partial hydrolysis
1,3-DAG, current most diglyceride includes that the EnovaTM Oil of KAO. Corp. SA's production are former based on this
Reason exploitation, the maximum shortcoming of the method is that technological process is complicated, it is necessary to multistep separation, the utilization rate of raw material is low in addition, in addition
Lipase is needed to use, and lipase price is higher, there is high cost etc. for industrial scale production diglyceride
Problem.（3）Glycerine solution：Will triglyceride oil and glycerine and a kind of alkali metal salt containing monocarboxylic acid or dicarboxylic acids
Or alkali salt or its mixture（Make catalyst）Mixing, by the glycerolysis of triglycerides, is obtained business, food-grade
1,3-DAG oil, but conventional glycerol rhizolomy needs the reaction at a high temperature of 220 ~ 260 DEG C so that triglycerides, diglyceride
Oxidation with aliphatic acid particularly unrighted acid is increased.At present, prepare triglyceride oil be mainly by soybean oil,
The triglyceride type oil and fat preparation such as rapeseed oil, peanut oil and corn oil, it is nearest for raw material prepares diglyceride with fish oil etc.
Also there are a small amount of report, such as Feltes（2010）Prepared by triglycerides alcoholysis method with lipase Novozyme 435 and be rich in
The diglyceride of n-3 PUFA；Eoma etc.（2010）Synthesized by hydrolysis, esterification process with lipase RMIM and Novozyme 435
Diglyceride rich in n-3 PUFA.
Conjugated fatty acid is the common name to polyunsaturated fatty acid position and stereoisomer with conjugate double bond system,
If a methyl between two double bonds, we can be referred to as the double bond that methyl separates, and if multiple methyl, we are referred to as
It is the double bond that many methyl separate, if two double bond conjugateds are together, we term it conjugated fatty acid.Conjugated fatty acid
Can be the form of diene, triolefin or tetraene, most common conjugated fatty acid is octadecadienoic acid and octatecatrienoic acid,
It is exactly CLA（conjugated linoleic acid, CLA）And conjugate linolenic acid（conjugated
linolenic acid, CLNA）.Conjugate linolenic acid has various isomers because position of double bond is different with configuration, punicic acid
(Punicic acid, PA) also known as trichosanic acid, because it is respectively from found in pomegranate seed and Seeds of Trichosanthes kirilowii, but were accredited as later
Same material, is now collectively referred to as punicic acid, and punicic acid is 9,11,13 double bonds conjugation, and 9 and 13 double bonds are configured as suitable
Formula, 11 double bonds are configured as trans conjugate linolenic acid（9c, 11t, 13c CLNA）.Punicic acid and 9c, 11t CLA（9,11
Double bond is conjugated, and 9 double bonds are configured as cis, and 11 double bonds are configured as a kind of trans, the most important isomers of CLA）'s
Similarity is that their fatty acid chain the 9th and the 11st is all undersaturated double bond, and spatial configuration is identical.Punicic acid
9c, 11t CLA can be converted in animal and human body, therefore can be as 9c, 11t CLA important natural diets source
（Tsuzuki etc., 2006）.
Conjugated fatty acid has the special physiological functions different from conventional polyunsaturated fatty acid.It is reported that CLA has
Many favourable physiological functions, such as improve humans and animals blood fat, antiatherosclerosis, anti-obesity, anticancer, antihypertensive work
With（Rainer etc., 2004）.CLA is in the whole world, particularly American-European countries as the functional food such as fat-reducing, reducing blood lipid and guarantor
Strong product are used widely.CLA is primarily present in milk lipid, cheese and ruminant meat.However, CLA contains in these foods
Amount only has about 1% (Sehat etc., 1998), and this makes the CLA that it can not possibly exist with natural resources to make the promotion health containing CLA
Food or medicine.The CLA of commercial is this isomerization product by obtained from the oily isomerization rich in oleic acid
Generally comprise equimolar 9c, 11t-CLA and 10t, 12c-CLA (Pariza etc., 2001) and other isomers.Consumption
There is the consideration of the aspects such as safety to the CLA of preparation of industrialization in person, CLA industrialized production Costco Wholesales are higher, and industrialization system
Standby CLA has various isomeric forms, and is not that every kind of isomers all has the function beneficial to human body.
The crucial difference of punicic acid and 9c, 11t-CLA is the 3rd undersaturated double bond, punicic acid of punicic acid
The 13rd in fatty acid chain has a cis double bond.So, punicic acid has the feature of " polyunsaturated fatty acid " again.It is many
Unrighted acid has important nutritive value, has beneficial effect to triglycerides in humans and animals body and cholesterol,
The danger of cardiovascular and cerebrovascular disease can be reduced, promotes growth and development.At present, polyunsaturated fatty acid is widely used in and is added to baby
Promote the development grown with intelligence of baby in food.
Prior art such as Authorization Notice No. CN100441559C Chinese inventions granted patent document punicic acid and its salt and
A kind of preparation method of the ester disclosure of the invention preparation method of punicic acid and its salt and ester.With pomegranate seed, Seeds of Trichosanthes kirilowii as former
Material, after cleaning, draining, less than 60 degrees Celsius of dryings, drying means includes natural air drying, low temperature drying, vacuum drying and freezes
Dry；Dried seed is extracted, the squeezing of directly colding pressing of supercritical extract or seed is obtained by after crushing using organic solvent
Pomegranate acid glycerol three ester crude extract crude oil, after degumming, depickling, decolouring, deodorization, dewaxing, refining is obtained pomegranate acid glycerol to crude oil
Three esters；Pomegranate acid glycerol three ester obtains pomegranate hydrochlorate after saponification, further obtains punicic acid after acidifying.Punicic acid is after esterification
Pomegranate acid esters is obtained, also pomegranate acid esters can be obtained by pomegranate acid glycerol three ester direct esterification.By pomegranate prepared by the inventive method
Acid and its punicic acid high purity 30-80% contained by ester and salt, the invention with edible natural with plant as raw material, products obtained therefrom peace
Quan Xinggao, there is a more wide application prospect, but effect of extracting and crude oil decolorizing effect in the method also has room for promotion.
The content of the invention
The present invention provides a kind of phosphatide type punicic acid fat or oil composition and preparation method thereof and answers for above-mentioned technical problem
With raw material abstraction pomegranate acid glycerol three ester excellent effect in preparation process, the pomegranate acid content of preparation is high, phosphatide type punicic acid oil
The high conversion rate of oil/fat composition and can be used in functional food and medicine.
It is of the invention to be for the scheme that above-mentioned technical problem is taken：A kind of phosphatide type punicic acid fat or oil composition, pomegranate
Acid lipid composition is made up of following component by mass percentage：55 ~ 85% diglyceride, 10 ~ 45% triglycerides,
0.2 ~ 8% monoglyceride and 0.03 ~ 9% residue, the whole being made up of above-mentioned monoglyceride, diglyceride and triglycerides
Punicic acid and the mass ratio of aliphatic acid are 0.3 ~ 0.7 in glyceride:1, residue is free fatty and glycerine.Stone of the invention
Pomegranate acid lipid composition can strengthen the preventive effect built up to fat, can also improve blood fat, body immunity be improved, beneficial to human body
Easily absorb, digest, green has no side effect, with certain healthcare function.
A kind of phosphatide type punicic acid fat or oil composition preparation method, comprises the following steps：The first step, the extraction of punicic acid：
1）Pretreatment：Pomegranate seed or Snakegourd Fruit seed are cleaned, is drained, dried；
2）Extract：Dry powder is obtained after dried pomegranate seed or Seeds of Trichosanthes kirilowii are crushed, dry powder is extracted through extractant, supercritical extract
Or directly cold pressing and squeeze to obtain pomegranate acid glycerol three ester CE, by pomegranate acid glycerol three ester CE degumming, decolouring, de-
Pomegranate acid glycerol three ester is refined to obtain after acid, deodorization, dewaxing；
3）The preparation of punicic acid：By step（2）In obtained pomegranate acid glycerol three ester by saponification, acidifying, esterification after pomegranate
Acid and pomegranate acid esters；
4）Purifying：By step（3）The punicic acid and pomegranate acid esters of acquisition are dissolved in organic solvent, by two step freeze crystallizations point
From obtain purity be 94 ~ 97% punicic acid；
Second step, mixture is mixed to form by the punicic acid of said extracted and glycerine, and lipozyme is added in the mixture
RMIM carries out enzymic catalytic reaction and phosphatide type pomegranate acid composition crude product is obtained under vacuo, and reaction temperature is 30 ~ 60 DEG C, reaction
6 ~ 12h of time, mixture is 200 ~ 500 with the mass ratio of lipozyme RMIM:1；
3rd step, to phosphatide type pomegranate acid composition crude product obtained above by the acid of molecular distillation fractionation of fatty and glycerine one
Ester, then through decolouring, deodorization and filtering, the phosphatide type punicic acid fat or oil composition needed for refining acquisition.
The method that the present invention prepares pomegranate acid lipid is simple, reasonable, and raw material is easy to get and economical, using two step freeze crystallizations
The punicic acid of high-purity is obtained, pomegranate acid content, the phosphatide type pomegranate of preparation in the phosphatide type pomegranate acid composition for preparing is lifted
Acid composition has excellent performance in terms of control body weight, improvement blood fat, enhance immunity, is also imitated with certain health care
Really.
Preferably, extractant in step 2 be n-hexane, petroleum ether, ether, ethanol, methyl alcohol, chloroform, n-butanol,
One or more mixtures in acetone, hexamethylene.The content for obtaining pomegranate acid glycerol three ester CE can be effectively increased, be carried
Effect of extracting is risen, organic solvent also has excellent stability.
Preferably, pomegranate acid glycerol three ester CE is decolourized using decolorising agent in step 2, decolorising agent is by following
Composition and weight portion are constituted：35 ~ 55 parts of dicyanodiamine, 8 ~ 35 parts of ammonium chloride, 0.001 ~ 0.002 part of menthone glycerol ketals, first
5 ~ 50 parts of aldehyde solution, 1 ~ 5 part of catalyst, 0.002 ~ 0.01 part of resveratrol, 0.5 ~ 1 part of chain extender, 40 ~ 60 parts of water, flocculation aid
20 ~ 50 parts, 2 ~ 5 parts of polyacrylamide.Decolorising agent reaction efficiency is high, good decolorizing effect, can lift the anti-of pomegranate acid glycerol three ester
Oxidisability.Catalyst uses glycerine solution custom catalystses, through experiment, the conventional Sexual behavior mode of catalyst and the difference of decolorizing effect
Property is little.And the effect of menthone glycerol ketals, resveratrol shows significant difference.Two-step crystallization method includes first step knot
The crystallization of brilliant and second step, the crystallization temperature of first step crystallization is 4 DEG C, and crystallization time is 8 ~ 16h, and crystallization pressure is 101KPa；
The crystallization temperature of second step crystallization is -20 ~ -70 DEG C, and crystallisation times are 3 ~ 5 times, and each crystallization time is 8 ~ 16h, crystallization pressure
It is 101KPa.The punicic acid of high-purity is obtained, and saves the time.
Preferably, the punicic acid and glycerine mixed proportion in second step are punicic acid：Glycerine=2 ~ 9:1, glycerine is by sweet
An oily ester, diglyceride, triglycerides composition, improve the pomegranate acid content in the punicic acid fat or oil composition for obtaining.
A kind of use of phosphatide type punicic acid fat or oil composition in functional food and medicine, functional food and medicine are at least
Wherein one side in for control body weight, improvement blood fat or enhance immunity.
Compared with prior art, beneficial effects of the present invention are：Phosphatide type punicic acid fat or oil composition is in stone in the present invention
Punicic acid is extracted in pomegranate seed or Snakegourd Fruit seed, material is easy to get, and it is economical, the phosphatide type punicic acid fat or oil composition of preparation is oily except having
Structural stability outside also with punicic acid various nutritional ingredients and physiological advantages, therefore using this composition for activity into
Point product for preparing more superiority with conventional products compared with, especially both has the effect of weight reducing of diglyceride, while also having
There is the effects such as anti-inflammatory, fat-reducing of punicic acid, thus this composition is widely used in control body weight, improved blood fat and raising
In the functional food and medicine of immunity, meanwhile, in the preparation process of this composition, preparation method is simple, rationally, punicic acid oil
Oil/fat composition edible safety is high, and obtained punicic acid high purity 94 ~ 97%, phosphatide type grease combination prepared by the present invention
The preparation process is simple of thing, low cost has broad application prospects.
Specific embodiment
It is described in further detail with reference to embodiments：
Embodiment 1：
A kind of phosphatide type punicic acid fat or oil composition, is made up of following component by mass percentage：55 ~ 85% diglyceride,
10 ~ 45% triglycerides, 0.2 ~ 8% monoglyceride and 0.03 ~ 9% residue, by above-mentioned monoglyceride, diglyceride and
Punicic acid and the mass ratio of aliphatic acid are 0.3 ~ 0.7 in whole glyceride of triglycerides composition:1, residue is free-fat
Acid and glycerine.Punicic acid fat or oil composition of the invention can strengthen the preventive effect built up to fat, can also improve blood fat, improve
Body immunity, easily absorbs beneficial to human body, digests, and green has no side effect, with certain healthcare function.
A kind of phosphatide type punicic acid fat or oil composition preparation method, comprises the following steps：The first step, the extraction of punicic acid：
1）Pretreatment：Pomegranate seed or Snakegourd Fruit seed are cleaned, is drained, dried；
2）Extract：Dry powder is obtained after dried pomegranate seed or Seeds of Trichosanthes kirilowii are crushed, dry powder is extracted through extractant, supercritical extract
Or directly cold pressing and squeeze to obtain pomegranate acid glycerol three ester CE, by pomegranate acid glycerol three ester CE degumming, decolouring, de-
Pomegranate acid glycerol three ester is refined to obtain after acid, deodorization, dewaxing；
3）The preparation of punicic acid：By step（2）In obtained pomegranate acid glycerol three ester by saponification, acidifying, esterification after pomegranate
Acid and pomegranate acid esters；
4）Purifying：By step（3）The punicic acid and pomegranate acid esters of acquisition are dissolved in organic solvent, by two step freeze crystallizations point
From obtain purity be 94 ~ 97% punicic acid；
Second step, mixture is mixed to form by the punicic acid of said extracted and glycerine, and lipozyme is added in the mixture
RMIM carries out enzymic catalytic reaction and phosphatide type pomegranate acid composition crude product is obtained under vacuo, and reaction temperature is 30 ~ 60 DEG C, reaction
6 ~ 12h of time, mixture is 200 ~ 500 with the mass ratio of lipozyme RMIM:1；
3rd step, to phosphatide type pomegranate acid composition crude product obtained above by the acid of molecular distillation fractionation of fatty and glycerine one
Ester, then through decolouring, deodorization and filtering, the phosphatide type punicic acid fat or oil composition needed for refining acquisition.
The method that the present invention prepares pomegranate acid lipid is simple, reasonable, and raw material is easy to get and economical, using two step freeze crystallizations
The punicic acid of high-purity is obtained, pomegranate acid content, the phosphatide type pomegranate of preparation in the phosphatide type pomegranate acid composition for preparing is lifted
Acid composition has excellent performance in terms of control body weight, improvement blood fat, enhance immunity, is also imitated with certain health care
Really.
Extractant in step 2 is n-hexane, petroleum ether, ether, ethanol, methyl alcohol, chloroform, n-butanol, acetone, hexamethylene
One or more mixtures in alkane.The content for obtaining pomegranate acid glycerol three ester CE, lifting extraction effect can be effectively increased
Really, organic solvent also has excellent stability.
Pomegranate acid glycerol three ester CE is decolourized using decolorising agent in step 2, and decolorising agent is by following component and weight
Amount part composition：35 ~ 55 parts of dicyanodiamine, 8 ~ 35 parts of ammonium chloride, 0.001 ~ 0.002 part of menthone glycerol ketals, formalin 5 ~
50 parts, 1 ~ 5 part of catalyst, 0.002 ~ 0.01 part of resveratrol, 0.5 ~ 1 part of chain extender, 40 ~ 60 parts of water, 20 ~ 50 parts of flocculation aid,
2 ~ 5 parts of polyacrylamide.Decolorising agent reaction efficiency is high, good decolorizing effect, can lift the inoxidizability of pomegranate acid glycerol three ester.
Two-step crystallization method includes first step crystallization and second step crystallization, and the crystallization temperature of first step crystallization is 4 DEG C, crystallization
Time is 8 ~ 16h, and crystallization pressure is 101KPa；The crystallization temperature of second step crystallization is -20 ~ -70 DEG C, and crystallisation times are 3 ~ 5
Secondary, each crystallization time is 8 ~ 16h, and crystallization pressure is 101KPa.The punicic acid of high-purity is obtained, and saves the time.
Punicic acid and glycerine mixed proportion in second step are punicic acid：Glycerine=2 ~ 9:1, glycerine is by monoglyceride, sweet
Oily diester, triglycerides composition, improve the pomegranate acid content in the punicic acid fat or oil composition for obtaining.
A kind of use of phosphatide type punicic acid fat or oil composition in functional food and medicine, functional food and medicine are at least
Wherein one side in for control body weight, improvement blood fat or enhance immunity.
Embodiment 2：
A kind of phosphatide type punicic acid fat or oil composition, is made up of by preferred mass percentage following component：60% glycerine two
Ester, 30% triglycerides, 6% monoglyceride and 1% residue, by above-mentioned monoglyceride, diglyceride and triglycerides group
Into whole glyceride in the mass ratio of punicic acid and aliphatic acid be preferably 0.5:1, residue is free fatty and glycerine.This
The punicic acid fat or oil composition of invention can strengthen the preventive effect built up to fat, can also improve blood fat, improve body immunity,
Easily absorbed beneficial to human body, digested, green has no side effect, with certain healthcare function.
Monoglyceride, diglyceride and triglycerides composition whole glyceride in punicic acid and aliphatic acid mass ratio not
It is only limitted to 0.3 ~ 0.7：1, also include：0.31：1、0.32：1、0.33：1、0.34：1……0.67：1、0.68：1、069：1、
0.7：1.
A kind of phosphatide type punicic acid fat or oil composition preparation method, comprises the following steps：The first step, the extraction of punicic acid：
1）Pretreatment：Pomegranate seed or Snakegourd Fruit seed are cleaned, is drained, dried；
2）Extract：Dry powder is obtained after dried pomegranate seed or Seeds of Trichosanthes kirilowii are crushed, dry powder is extracted through extractant, supercritical extract
Or directly cold pressing and squeeze to obtain pomegranate acid glycerol three ester CE, by pomegranate acid glycerol three ester CE degumming, decolouring, de-
Pomegranate acid glycerol three ester is refined to obtain after acid, deodorization, dewaxing；
3）The preparation of punicic acid：By step（2）In obtained pomegranate acid glycerol three ester by saponification, acidifying, esterification after pomegranate
Acid and pomegranate acid esters；
4）Purifying：By step（3）The punicic acid and pomegranate acid esters of acquisition are dissolved in organic solvent, by two step freeze crystallizations point
From the crystallization temperature of first step crystallization is 4 DEG C, and crystallization time is 8 ~ 16h, and crystallization pressure is 101KPa；The knot of second step crystallization
Brilliant temperature is -20 ~ -70 DEG C, and crystallisation times are 3 ~ 5 times, and each crystallization time is 8 ~ 16h, and crystallization pressure is 101KPa, is obtained
Purity is 94 ~ 97% punicic acid；
Second step, by the punicic acid of said extracted and glycerine with 2 ~ 9:1 ratio is mixed to form mixture, adds in the mixture
Enter lipozyme RMIM carries out the prepared phosphatide type pomegranate acid composition crude product of enzymic catalytic reaction under vacuo, and reaction temperature is 30
~ 60 DEG C, 6 ~ 12h of reaction time, mixture is preferably 300 with the mass ratio of lipozyme RMIM:1；
3rd step, to phosphatide type pomegranate acid composition crude product obtained above by the acid of molecular distillation fractionation of fatty and glycerine one
Ester, then through decolouring, deodorization and filtering, the phosphatide type punicic acid fat or oil composition needed for refining acquisition.
In the prior art of the routine techniques dawn known to those skilled in the art in the first step to the 3rd step, do not make herein in detail
Thin narration.
Pomegranate acid glycerol three ester CE is decolourized using decolorising agent in step 2, and decolorising agent is by following component and excellent
The weight portion composition of choosing：40 parts of dicyanodiamine, 30 parts of ammonium chloride, 0.0018 part of menthone glycerol ketals, 30 parts of formalin, urge
4 parts of agent, 0.0029 part of resveratrol, 0.6 part of chain extender, 55 parts of water, 35 parts of flocculation aid, 4 parts of polyacrylamide.Decolorising agent is anti-
Answering efficiency high, good decolorizing effect can lift the inoxidizability of pomegranate acid glycerol three ester.
Punicic acid in second step is to be not limited only to punicic acid with glycerine mixed proportion：Glycerine=2 ~ 9:1, also including pomegranate
Acid：Glycerine=2.01：1、2.02：1、2.03：1、2.04：1……8.97：1、8.98：1、8.99：1、9：1.
Embodiment 3：
Pomegranate seed is collected, dry powder 1000g is crushed to obtain after 40 DEG C of oven for drying, with 5 times of petroleum ethers of volume at less than 60 DEG C
The triglycerides crude extract of green is obtained after refluxing extraction 6h, oil yield is 28.2%.Triglycerides crude extract 50mL is taken to add
Enter the potassium hydroxide-ethanol solution 200mL of the 2M 90% saponification 2h at nitrogen protection is lower 60 DEG C, added after adding 50mL water
The extracting of 50mL petroleum ethers three times removes not saponification compounds, adds in 6M hydrochloric acid 100mL and is extracted with petroleum ether after acidifying and goes
Upper strata obtains petroleum ether solution, then by obtaining punicic acid crude extract after rotary evaporation in vacuo.Punicic acid crude extract is dissolved in second
In alcohol, the lower 4 DEG C of crystallizations 8h of normal pressure removes saturated fatty acid, and the ethanol solution for obtaining is further at ambient pressure in subzero 20 DEG C knots
Brilliant 16h, repeats 3 punicic acids of the isolated high-purity of freezing and crystallizing.Stone obtained in above-mentioned technique is used in the present embodiment
Pomegranate acid is through gas chromatographic analysis purity up to 97%.
By the punicic acid of said extracted and glycerine with 2:1 ratio is mixed to form mixture, adds in the mixture
It is thick that lipozyme RMIM (Novozymes Company of Denmark) carry out the prepared phosphatide type pomegranate acid composition of enzymic catalytic reaction under vacuo
Product, reaction temperature is 30 DEG C, reaction time 10h, and said mixture is 200 with the mass ratio of lipozyme RMIM:1.To upper
Obtained phosphatide type pomegranate acid composition crude product is stated by the acid of molecular distillation fractionation of fatty and monoglyceride, then used decolouring, taken off
Smelly and filtering method refines the phosphatide type punicic acid fat or oil composition needed for obtaining.
After testing, phosphatide type punicic acid fat or oil composition manufactured in the present embodiment is as mass fraction by following components structure
Into：55% diglyceride, 28% triglycerides, 8% monoglyceride and 9% residue, by above-mentioned monoglyceride, sweet
Punicic acid and the mass ratio of aliphatic acid are 0.3 in whole glyceride of oily diester and triglycerides composition:1, above-mentioned residue is
Free fatty and glycerine.
Taking phosphatide type punicic acid fat or oil composition carries out zoopery to the control action of body weight, and research said composition is to body
Whether the increase of weight and body fat is inhibited.
The male ICR mouse of 6 week old are provided by Zhejiang Province's Experimental Animal Center, and ICR mouse are divided at random after adapting to 7 days
It is 2 groups, every group 10.Following 6 week, 2 groups of mouse in addition to feeding feed, respectively with phosphatide type pomegranate acid lipid group
The consumption once oral gavage of compound and pomegranate acid triglyceride oil (its pomegranate acid content 78%) 50mg/kg body weight daily
To each mouse, the body weight of each mouse is determined every two weeks, the average value of survey body weight is as shown in table 1.From table 1 as can be seen that and stone
Pomegranate acid triglyceride oil group is compared, and phosphatide type punicic acid fat or oil composition can significantly inhibit Mouse Weight and gather way, control volume
The growth of weight.
Influence to blood fat：Taking phosphatide type punicic acid fat or oil composition carries out zoopery, and research said composition is to blood fat
Whether improvement result is had.
The male ICR mouse of 6 week old are provided by Zhejiang Province's Experimental Animal Center, and ICR mouse are divided at random after adapting to 7 days
It is 2 groups, every group 10.Following 6 week, 2 groups of mouse in addition to feeding feed, respectively with phosphatide type pomegranate acid lipid group
The consumption of 50mg/kg body weight is once orally filled daily for compound and pomegranate acid triglyceride oil (its pomegranate acid content is 78%)
Stomach takes hematometry to each mouse, experiment and determines lipid of mice after terminating.The average value of surveyed blood fat is as shown in table 2.Can be with from table 2
Find out, compared with pomegranate acid triglyceride oil group, phosphatide type punicic acid fat or oil composition can significantly improve mouse high density lipoprotein level
White cholesterol level (HDL-C), reduces LDL-C (LDL-C) content, improves the ratio of LDL-C and HDL-C
Value, this shows that phosphatide type punicic acid fat or oil composition can significantly improve lipid of mice.
Embodiment of above is merely to illustrate the present invention, and not limitation of the present invention, the ordinary skill people of this area
Member, without departing from the spirit and scope of the present invention, can also make a variety of changes and modification.Therefore, it is all equivalent
Technical scheme fall within scope of the invention, scope of patent protection of the invention should be defined by the claims.
Claims (7)
1. a kind of phosphatide type punicic acid fat or oil composition, it is characterised in that：The punicic acid fat or oil composition is by weight percent
Meter is made up of following component：55 ~ 85% diglyceride, 10 ~ 45% triglycerides, 0.2 ~ 8% monoglyceride and 0.03 ~ 9%
Residue, punicic acid and aliphatic acid in the whole glyceride be made up of above-mentioned monoglyceride, diglyceride and triglycerides
Mass ratio is 0.3 ~ 0.7:1, the residue is free fatty and glycerine.
2. a kind of phosphatide type punicic acid fat or oil composition preparation method, it is characterised in that：Comprise the following steps：The first step, pomegranate
The extraction of acid：
1）Pretreatment：Pomegranate seed or Snakegourd Fruit seed are cleaned, is drained, dried；
2）Extract：Dry powder is obtained after dried pomegranate seed or Seeds of Trichosanthes kirilowii are crushed, dry powder is extracted through extractant, supercritical extract
Or directly cold pressing and squeeze to obtain pomegranate acid glycerol three ester CE, by pomegranate acid glycerol three ester CE degumming, decolouring, de-
Pomegranate acid glycerol three ester is refined to obtain after acid, deodorization, dewaxing；
3）The preparation of punicic acid：By the step（2）In obtained pomegranate acid glycerol three ester by saponification, acidifying, esterification after
Punicic acid and pomegranate acid esters；
4）Purifying：By step（3）The punicic acid and pomegranate acid esters of acquisition are dissolved in organic solvent, by two step freeze crystallizations point
From obtain purity be 94 ~ 97% punicic acid；
Second step, mixture is mixed to form by the punicic acid of said extracted and glycerine, and lipozyme is added in the mixture
RMIM carries out enzymic catalytic reaction and phosphatide type pomegranate acid composition crude product is obtained under vacuo, and reaction temperature is 30 ~ 60 DEG C, reaction
6 ~ 12h of time, mixture is 200 ~ 500 with the mass ratio of lipozyme RMIM:1；
3rd step, to phosphatide type pomegranate acid composition crude product obtained above by the acid of molecular distillation fractionation of fatty and glycerine one
Ester, then through decolouring, deodorization and filtering, the phosphatide type punicic acid fat or oil composition needed for refining acquisition.
3. a kind of phosphatide type punicic acid fat or oil composition preparation method according to claim 2, it is characterised in that：The step
Extractant in rapid 2 is the one kind in n-hexane, petroleum ether, ether, ethanol, methyl alcohol, chloroform, n-butanol, acetone, hexamethylene
Or several mixtures.
4. a kind of phosphatide type punicic acid fat or oil composition preparation method according to claim 2, it is characterised in that：The step
Pomegranate acid glycerol three ester CE is decolourized using decolorising agent in rapid 2, and the decolorising agent is by following component and weight portion group
Into：35 ~ 55 parts of dicyanodiamine, 8 ~ 35 parts of ammonium chloride, 0.001 ~ 0.002 part of menthone glycerol ketals, 5 ~ 50 parts of formalin, urge
1 ~ 5 part of agent, 0.002 ~ 0.01 part of resveratrol, 0.5 ~ 1 part of chain extender, 40 ~ 60 parts of water, 20 ~ 50 parts of flocculation aid, polyacrylamide
2 ~ 5 parts of amine.
5. a kind of phosphatide type punicic acid fat or oil composition preparation method according to claim 2, it is characterised in that：It is described
Two-step crystallization method include the first step crystallization and second step crystallization, the first step crystallization crystallization temperature be 4 DEG C, crystallization time be 8 ~
16h, crystallization pressure is 101KPa；The crystallization temperature of second step crystallization is -20 ~ -70 DEG C, and crystallisation times are 3 ~ 5 times, every time knot
The brilliant time is 8 ~ 16h, and crystallization pressure is 101KPa.
6. a kind of phosphatide type punicic acid fat or oil composition preparation method according to claim 2, it is characterised in that：Described
Punicic acid and glycerine mixed proportion in two steps are punicic acid：Glycerine=2 ~ 9:1, glycerine is by monoglyceride, diglyceride, glycerine
Three esters are constituted.
7. use of a kind of phosphatide type punicic acid fat or oil composition in functional food and medicine, the functional food and medicine are extremely
The wherein one side being used for less in control body weight, improvement blood fat or enhance immunity.
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| CN108456699A (en) * | 2018-02-26 | 2018-08-28 | 浙江海洋大学 | A kind of phosphatide type calendic acid fat or oil composition and its preparation method and application |
| CN108477309A (en) * | 2018-02-26 | 2018-09-04 | 浙江海洋大学 | A kind of phosphatide type catalpic acid fat or oil composition and its preparation method and application |
| CN110141564A (en) * | 2019-06-06 | 2019-08-20 | 广东省农业科学院蚕业与农产品加工研究所 | A kind of glyceride mixture and its preparation method and application rich in polyunsaturated fatty acid |
| CN113498808A (en) * | 2021-07-05 | 2021-10-15 | 广东粤膳特医营养科技有限公司 | Coconut oil composition and preparation method and application thereof |
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Cited By (5)
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|---|---|---|---|---|
| CN108456699A (en) * | 2018-02-26 | 2018-08-28 | 浙江海洋大学 | A kind of phosphatide type calendic acid fat or oil composition and its preparation method and application |
| CN108477309A (en) * | 2018-02-26 | 2018-09-04 | 浙江海洋大学 | A kind of phosphatide type catalpic acid fat or oil composition and its preparation method and application |
| CN110141564A (en) * | 2019-06-06 | 2019-08-20 | 广东省农业科学院蚕业与农产品加工研究所 | A kind of glyceride mixture and its preparation method and application rich in polyunsaturated fatty acid |
| CN113498808A (en) * | 2021-07-05 | 2021-10-15 | 广东粤膳特医营养科技有限公司 | Coconut oil composition and preparation method and application thereof |
| CN113498808B (en) * | 2021-07-05 | 2023-09-19 | 广东粤膳特医营养科技有限公司 | Coconut oil composition and preparation method and application thereof |
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