WO2008146942A1 - Procédé de production d'une substance fonctionnelle contenant des phospholipides, et procédé de production d'un glycérophospholipide de type plasmalogène - Google Patents
Procédé de production d'une substance fonctionnelle contenant des phospholipides, et procédé de production d'un glycérophospholipide de type plasmalogène Download PDFInfo
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- WO2008146942A1 WO2008146942A1 PCT/JP2008/060120 JP2008060120W WO2008146942A1 WO 2008146942 A1 WO2008146942 A1 WO 2008146942A1 JP 2008060120 W JP2008060120 W JP 2008060120W WO 2008146942 A1 WO2008146942 A1 WO 2008146942A1
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- WIPO (PCT)
- Prior art keywords
- plasmalogen
- phospholipid
- type
- mass
- poultry
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- 150000003904 phospholipids Chemical class 0.000 title claims abstract description 97
- 239000000463 material Substances 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 150000002327 glycerophospholipids Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 51
- 244000144977 poultry Species 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 24
- 239000000843 powder Substances 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 239000002270 dispersing agent Substances 0.000 claims abstract description 4
- 230000001804 emulsifying effect Effects 0.000 claims abstract description 4
- 150000002632 lipids Chemical class 0.000 claims description 57
- 235000013330 chicken meat Nutrition 0.000 claims description 55
- 241000287828 Gallus gallus Species 0.000 claims description 52
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- 235000013594 poultry meat Nutrition 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 16
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 16
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 11
- 239000012046 mixed solvent Substances 0.000 claims description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 235000013372 meat Nutrition 0.000 abstract description 32
- 210000000481 breast Anatomy 0.000 abstract description 7
- 230000001131 transforming effect Effects 0.000 abstract description 2
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 description 18
- 210000003491 skin Anatomy 0.000 description 14
- 239000002699 waste material Substances 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 235000013601 eggs Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000000105 evaporative light scattering detection Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000209094 Oryza Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 238000009395 breeding Methods 0.000 description 4
- 230000001488 breeding effect Effects 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
- 238000007796 conventional method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000002615 epidermis Anatomy 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 235000013376 functional food Nutrition 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000787 lecithin Substances 0.000 description 4
- 235000010445 lecithin Nutrition 0.000 description 4
- 229940067606 lecithin Drugs 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 206010034203 Pectus Carinatum Diseases 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000009329 organic farming Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- -1 sphingolipid lipid Chemical class 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000004895 Lipoproteins Human genes 0.000 description 2
- 108090001030 Lipoproteins Proteins 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 230000005754 cellular signaling Effects 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000004665 fatty acids Chemical group 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 150000002339 glycosphingolipids Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000013632 homeostatic process Effects 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 238000001474 liquid chromatography-evaporative light scattering detection Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000016273 neuron death Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000009461 vacuum packaging Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- JSPNNZKWADNWHI-PNANGNLXSA-N (2r)-2-hydroxy-n-[(2s,3r,4e,8e)-3-hydroxy-9-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]heptadecanamide Chemical compound CCCCCCCCCCCCCCC[C@@H](O)C(=O)N[C@H]([C@H](O)\C=C\CC\C=C(/C)CCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JSPNNZKWADNWHI-PNANGNLXSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000006386 Myelin Proteins Human genes 0.000 description 1
- 108010083674 Myelin Proteins Proteins 0.000 description 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- JCABVIFDXFFRMT-DIPNUNPCSA-N [(2r)-1-[ethoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC)OC(=O)CCCCCCCC=CCCCCCCCC JCABVIFDXFFRMT-DIPNUNPCSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 235000019726 broiler meat Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- 229930183167 cerebroside Natural products 0.000 description 1
- RIZIAUKTHDLMQX-UHFFFAOYSA-N cerebroside D Natural products CCCCCCCCCCCCCCCCC(O)C(=O)NC(C(O)C=CCCC=C(C)CCCCCCCCC)COC1OC(CO)C(O)C(O)C1O RIZIAUKTHDLMQX-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000003374 diacylglycerol group Chemical group 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000005012 myelin Anatomy 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 235000021441 organic meat Nutrition 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000004003 subcutaneous fat Anatomy 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- 210000000689 upper leg Anatomy 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
- A23J1/02—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from meat
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Definitions
- the present invention provides a simple operation of a phospholipid-containing functional material useful as a functional food material, a pharmaceutical material, a cosmetic material, etc.
- the present invention relates to a method for producing with good yield, and also relates to a plasmalogen type glyceport phospholipid. Background art
- Lipid refers to a substance that has a long-chain fatty acid or a similar hydrocarbon chain in a molecule and exists in a living body or is derived from a living organism. This lipid can be classified into simple lipids and complex lipids. Simple lipids are composed of C, H, and O, and are generally soluble in acetone. The simple lipid triacylglycerol exists in an animal body as a reservoir of energy in adipose tissue. On the other hand, complex lipids are a group of lipids including phosphoric acid P and base N. Therefore, complex lipids consist of a hydrophobic part (fatty acid part) and a hydrophilic part (phosphoric acid or base part), exhibiting amphipathic properties. Generally, the simple lipid is soluble in acetone. In contrast, complex lipids are insoluble in acetone. Such complex lipids are constituents of biological membranes.
- the complex lipid examples include (1) glyceline phospholipids [phosphatidylcholine (also known as lecithin), phosphatidylethanolamine, and the like. ], (2) Sphingolin lipids (sphingomyelin, ceramide dosylatin, etc.), (3) Glycosphingolipids (celebral mouthsides, sulfatides) TJP2008 / 060120 and Gandarioside belong. ), And (4) Groseroglycolipids (including those in which various cocoons are bound to diacylglycerol present in microorganisms and higher plants).
- the (2) sphingolipid lipid and the (3) sphingoglycolipid are collectively referred to as sphingolipids.
- the glyceport phospholipid is a general term for phospholipids having daricerophosphate as a skeleton, and includes phosphatidylcholine (lecithin), phosphatidylethanolanolin, diphosphitidylglycerol, and the like.
- the nonpolar part is often an ester of a fatty acid, but there is also a plasmalogen type having a butyl ether bond.
- This glyceport phospholipid is important as a component of biological membranes.
- plasmalogen-type glycerophospholipid has been recently attracting attention as an antioxidant phospholipid because it is highly sensitive to vinyl ether bonds. It has been.
- plasmalogen-type glyceport phospholipids have contributed to the oxidative stability of phospholipid membranes containing cholesterol by a mechanism different from that of ⁇ -tocopherol (vitamin E), an antioxidant component of cell membranes. (See, for example, “J. Lipid Res.”, Pp. 44, pp.
- Such plasmalogen-type glyceport phospholipids are expected to prevent brain neuronal cell death in dementia, but in reality there are no sources that are safe and available in large quantities.
- sphingomyelin in order to produce a relatively large amount of sphingomyelin from total lipids of foods, animal tissues, etc., it can be produced by elution stepwise in a column chromatography using a key acid or the like, or a solvent Manufactured by fractionation using a fractionation method. Both require complex procedures.
- acetone is added to total lipids to precipitate complex lipids (phospholipids) (insoluble part), and the insoluble part is washed with ether to remove the glyceport phospholipids.
- a method of fractionation is common. This fraction contains not only sphingomyelin but also glycosphingolipids such as cerebroside.
- chicken skin phospholipids are rich in human sphingomyelin and plasmalogen-type dariceroline qualities.
- Chicken skin is more useful as a raw material for human sphingomyelin compared to conventional raw material sources, but it contains a large amount of subcutaneous fat, sometimes exceeding 70% by mass, and this removal is extremely complicated. There's a problem. Chicken skin contains plasmalogen-type glycerophospholipid at the same level as human sphingomyelin, and the ratio of phosphatidylcholine (lecithin) and phosphatidinorethanolamine is significantly higher in the latter. is there.
- the present inventors have eagerly developed a raw material that surpasses chicken skin, and the neutral lipid content in chicken meat, especially rice meat, is 30 to 70 times smaller than chicken skin, and it is a human sphingo.
- the total content of myelin and plasmalogen-type glyceport phospholipids is several times greater.
- the ratio of plasmalogen-type glyceguchi phospholipids to human sphingomyelin is more than 85% by mass
- the composition ratio of plasma mouth type darisserophospholipid is 50-75% by mass in adult chickens, phosphatidylcholine in young chickens, and phosphatidylethanolamine in young chickens.
- Plasmalogen-type phosphatidylcholine content is more than 30 times that of chicken skin, plasmalogen-type phosphatidylethanol in young chickens As a raw material for extraction of plasmalogen-type glyce mouth phospholipid (mixed in two kinds), plasmalogen-type phosphatidylcholine alone, and plasmalogen-type phosphatidylethanolamine alone, which is about twice as low as chicken skin, conventional examples We succeeded in finding a poultry fillet that was not cost-effective.
- Adult fillet has 1 mass of total fat. /. 80% of them are phospholipids (neutral lipids are as small as 0.2% by mass), of which 45% by mass is plasmalogen-type glycerophospholipid (70% of which is plasmalogen-type) in phospha Chijirukori down) content in the raw breast 0s. 3 6 wt% (human type Sufi Ngomierin is slightly 0.0 3 mass 0/0), which is high, Rudake be processed as a main material Can be used to prepare functional foods with high added value.
- phospholipids neutral lipids are as small as 0.2% by mass
- poultry fillet along with thighs, has a high rate of meat collection, but because it is hard and crunchy and lacks juicy taste, it has been treated as low-use meat for a long time despite being healthy. Is receiving.
- the annual meat culled from 100 million hens and 200,000 tons of minced meat is 15,000 tons, and it is strongly required to use them as domestic livestock. Disclosure of the invention
- the present invention is a method for producing a functional material containing a large amount of plasmalogen-type glyce mouth phospholipid from poultry, particularly chicken fillet, and poultry fillet powder
- An object of the present invention is to provide a method for producing a high-purity plasmalogen-type glyceport phospholipid from the above functional material with a simple operation and in a high yield.
- the present inventors have obtained a functional material containing a large amount of plasmalogen-type glycerophospholipid by applying a specific process to poultry, particularly chicken fillet. It has been found that high-purity plasma-single-type glycepore phospholipids can be obtained efficiently by applying a specific process to poultry fillet powder, and based on this finding, the present invention is It came to be completed.
- Poultry fillet (a) Mince process at low temperature and low oxygen atmosphere, (b) Paste process at low temperature using emulsifying dispersant (c) Low temperature drying A method for producing a functional material containing a phospholipid by transforming its shape by at least one process selected from the powdering processes of the above, comprising the sum of plasmalogen-type glycerophospholipid and sphingomyelin A phospholipid-containing functional material in which the content of the former in the amount is 85% by mass or more and the content of all phospholipids in the total lipid is 40% by mass or more is obtained. , Manufacturing method of functional material containing phospholipid,
- the poultry are adult chickens (hereinafter sometimes referred to as abandoned chickens), and the former is 40% by mass or more in the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerophospholipid.
- the poultry are adult broiler chickens and males, and the composition ratio of phosphatidinorecholine and phosphatidylethanolamine in plasmalogen-type glycerophospholipid is 50% by mass or more, (1) or the method described in (2), (5)
- the poultry is a pleuler, and the latter is 50% by mass or more in the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycepore phospholipid, as described in (1) or (2) above the method of,
- the mixed solvent in step (B) contains n-hexane and acetone in a volume ratio of 4: 6 to 6: 4, and the amount used is 1 per 1 g of dry total lipid.
- step (C) The water-soluble ketone solvent in step (C) is acetone, and the amount used is 10 to 30 mL per 1 g of the dried processed product of the soluble part obtained in step (B).
- a plasmalogen-type glyce mouth which is useful as a functional food material, a pharmaceutical material, a cosmetic material, etc. from poultry, particularly chicken breast meat.
- Plasmalogen-type glycerophospholipid, plasmalogen-type phosphatidylcholine simple substance, and plasmalogen-type phosphatidinoleethanolamine simple substance can be provided.
- the poultry fillet shape-changing technology of the present invention and the pasting technology using emulsified and dispersed natural preparations are secondary functions that do not harden by heat treatment and maintain a succulent feeling with no by-product dripping even during freezing and thawing treatment. Therefore, the rice paste is extremely useful as a high-value-added food material for rice meat, and the present invention is the beginning of high-value-added rice meat, resulting in an increase in consumption. It is expected to contribute to health promotion.
- Fig. 1 ELS D detection chromatogram of substances obtained from waste chicken fillet by each operation.
- Fig. 2 ELSD detection chromatograms of substances obtained by each operation from waste chicken fillet of organic farming breeding hens (local chickens).
- Fig. 3 ELSD detection chromatograms of substances obtained from each operation of commercially available young chicken breast meat.
- the method for producing a phospholipid-containing functional material of the present invention comprises at least one step selected from the following steps ( a ), (b) and (c):
- the production method of type glyceguchi phospholipid is composed of (A) step, (B) step and (C) step.
- This step (a) is a mincing step in a low temperature / low oxygen atmosphere.
- poultry fillet, especially chicken fillet if it has a skin, it is first skinned with a skinner treatment and then minced as usual. Lower the temperature, preferably 5. It is desirable to set the minced size and minced rate with priority given to avoiding local heat generation at the shredded portion after cooling to C or lower.
- the minced meat and air exposure after mincing is minimized, and furthermore, with air purifiers to suppress air oxidation and bacterial infection, the room temperature is low, preferably in a semi-enclosed space of 15 ° C or less It is preferable to implement the treatment and its sealed packaging.
- the obtained mince should be vacuum-packed with a high barrier film and stored refrigerated.
- This step (b) is a pasting step at a low temperature using an emulsifying dispersant.
- step (b) skinned fillet meat, preferably the meat that has been minced in the step (a) and vacuum-packed refrigerated and stored, preferably a non-enzymatic emulsion-dispersed natural preparation for protein foodstuffs.
- Add an aqueous solution dissolved in an appropriate amount of water mix evenly with an appropriate cutter mixer or processor, and paste into a straight (straight type). It is recommended that the pasted type be prepared, and this paste be cooled with a high-parity film and then cooled and stored at a low temperature, preferably refrigerated. Refrigeration is possible for long-term storage.
- This step (c) is a powdering step by low temperature drying.
- step (c) skinned meat, preferably minced meat that has been refrigerated and stored in vacuum in the step (a), or in some cases, any of the straight type pastes in the step (b)
- it is better to dry it in a minimally invasive manner with a commercially available freeze-drying device, and if necessary, pulverize it by low-temperature pulverization, and store this powder refrigerated under light shielding after vacuum packaging of a hybrid film.
- the content ratio of the former in the total amount of plasmalogen glyce mouth phospholipid and sphingomyelin is 85% by mass or more, and The total content of phospholipids is 40% by mass or more.
- the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glyce mouth phospholipid is 50% by mass or more of the former, and adult broiler chickens .
- the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerin lipid is 50 masses in the former. / Is 0 or more, if a broiler, phosphine Achijiruko Li down and the component ratio of phosphatidyl ethanolamine plasmalogen type glycerin port Li down lipids, the latter 5 0 mass. / 0 or more.
- This step (A) is a step of extracting the total fat from the poultry fillet powder, preferably the chicken fillet powder, and drying it.
- poultry fillet powder is prepared.
- the rice trimet meat may be dried and pulverized as it is, and minced and pasted as necessary. Then, it may be dried and powdered.
- a powder that is refrigerated and stored in a shaded state after vacuum packaging of the high barrier film obtained in [Step (c)] is used.
- the total lipid is extracted from the poultry fillet powder thus obtained using a solvent and dried to obtain a dry total lipid.
- Solvents used for extraction of total lipids are those that are safe for food hygiene and have good extraction efficiency. As such a solvent, ethanol is particularly suitable. This extraction process can be performed according to a conventional method. However, ethanol-soluble non-lipid components are also extracted in this extraction process.
- the extract can be obtained by removing the solvent using a rotary evaporator or by introducing nitrogen gas.
- the dry total lipid obtained in the step (A) is extracted with a mixed solvent of an aliphatic hydrocarbon solvent and a water-soluble ketone solvent, and an insoluble portion and a soluble portion are extracted. It is the process of separating into.
- examples of the aliphatic hydrocarbon solvent that is one component of the mixed solvent used for the extraction treatment of the dried total lipid include n-pentane, isopentane, n-hexane, isohexane, n Examples include monoheptane, isoheptane, cyclopentane, cyclohexane, etc., and these may be used alone or in combination of two or more. N Monohexane is preferred.
- water-soluble ketone solvent which is the other component of the mixed solvent
- acetone and / or methyl ethyl ketone can be used, and among these, acetone is preferable.
- the ratio is preferably 4: 6 to 6: 4 in terms of volume ratio, and 4.5: 5.5 to 5.5: 4.5. Is more preferable.
- the amount of the mixed solvent is usually about 10 to 30 mL per gram of dry total lipid.
- the soluble part obtained in the step (B) is dried and then extracted with a water-soluble ketone solvent, and the insoluble part (hereinafter referred to as plasmalogen-type glyceport phospholipid) This is sometimes referred to as crude plasmalogen-type glycepore phospholipid.
- the soluble part obtained in the step (B) is dried according to a conventional method.
- a method of distilling off the mixed solvent in the soluble part using a rotary evaporator can be used.
- the dried product obtained in this way is extracted with a water-soluble ketone solvent according to a conventional method.
- the water-soluble ketone solvent used in this case include acetone and / or methyl ethyl ketone, but aceton is preferable.
- acetone When acetone is used as the extraction solvent, it is usually about 10 to 30 mL per lg of dried product. If the amount of solvent used is less than 10 mL, the extraction process cannot be performed sufficiently, and the purity and recovery rate of the plasmalogen-type glycepore phospholipid in the insoluble part may be reduced. Meanwhile, over 30 mL Therefore, the effect of improving the purity and recovery rate of plasmalogen-type glycerophospholipid is hardly exhibited for the amount.
- the preferable amount of the solvent used is 15 to 25 mL per 1 g of the dried processed product.
- the extraction solution can be separated into a soluble part and an insoluble part (crude plasmalogen-type darice cellophospholipid) mainly composed of plasmalogen-type glycepore phospholipid by subjecting it to a centrifugal separation treatment.
- the amount of plasmalogen-type glyceport phospholipid in the insoluble part is usually 40% by mass or more.
- plasmalogen-type glyceport phospholipid can be produced with high purity and high yield from the total fat of poultry fillet, preferably chicken fillet, by simple means. .
- 0.1 to 3 mass of crude plasma mouth-type glyce mouth phospholipid is usually obtained from the dry powder of chicken breast meat. / 0 can be obtained at a rate of about 0 .
- the crude plasmalogen glycerophospholipid obtained by the method of the present invention mainly contains phosphatidylcholine (P C) and partly phosphatidylethanolamine (P E). About 30% by mass of the PC is a plasmalogen type, and PE contains about 65% by mass of a plasma single-gen type.
- R 1 , R 2 long chain aliphatic group
- glyce mouth phospholipid is a glycerol sn-1 (position 1) as shown in formula (II).
- glycerol sn-1 position 1 as shown in formula (II).
- the plasmalogen type has a butyl ether bond with an alkenyl group on sn-1 of glycerol as shown in formula (III).
- X is an aminomino group, it is phosphatidylethanolamine, and when X is a trimethylaminoethyl group, it is phosphatidylcholine.
- the plasmalogen glycerophospholipid is attracting attention as an antioxidant phospholipid because of its high radical sensitivity of vinyl ether bond, and is known to contribute to the oxidative stability of phospholipid membranes containing cholesterol. .
- plasmalogen-type glyceport phospholipids are not only involved in the antioxidant properties of cell membranes and lipoproteins, but also have an important role in the cell signaling system.
- Such plasmalogen-type glyceport phospholipids are expected to have the effect of preventing brain neuronal cell death in dementia and the onset prevention effect of atherosclerosis.
- the present invention is also characterized by being obtained using the method of the present invention described above.
- a plasmalogen-type glyceport phospholipid is also provided.
- Freshly degassed and chilled chilled meat harvested from organic chicken laying hens (manufactured by Agricultural Union Enchikin (Chiran-cho, Minamikyushu-shi, Kagoshima)) (hereinafter sometimes referred to as "organic meat") )
- organic meat a commercial minced device installed in an air-cooled chamber while minimizing air exposure during the process
- 1 mm of minced with a size of several millimeters while maintaining the internal temperature at 1 oC or less 95 mass
- Take the mince obtained in% yield in a high-paria film wrapping material immediately deaerate and store in a refrigerator.
- the refrigerated mince was subjected to the following component analysis.
- composition ratio and the content are mass%.
- the characteristics of the fillet phospholipids in the waste chickens of organic farming breeding eggs are as follows.
- PL-PC is the next higher function type, followed by P L_P E is large, but SM is extremely small.
- Higher-order function type refers to a function that is directly involved in life homeostasis; for example, a function that inhibits apoptosis of cranial neurons or a function related to myocardial homeostasis.
- the total PC is actually less than 70%.
- total PE is less than 20%, of which 60% is P L-PE, in contrast to P L-PC in total PC, which is just over 20%. It is also noteworthy that the SM content is extremely low at 2% by mass, even compared to the skin described later.
- composition ratio and the content are mass%.
- the characteristic feature of the henrye phospholipids is that, first of all, it accounts for more than 80% of the total lipids with a content of only 1% by mass. Furthermore, almost 70% of the total PC is overwhelmingly large. Reflecting this, the higher-order function type has a high P L_PC of 30% by mass or more, but the SM is extremely low. Next to this, total PE is slightly over 17% by mass, of which, over 75% by mass is PL-PE, and in contrast to that PL-PC in total PC is over 45% by mass. It is. It is also noted that the SM content is extremely low at 3.2% by mass even compared to the epidermis described later.
- composition of the phospholipid by HP LC / ELSD analysis was as follows: p1PC (21.4%), p1PE (13.4%), PC (50.3%), PE (4.8 %), SM (1.3%), the composition ratio of p1 type total is
- composition ratio and content rate are mass%.
- the deoiled minced skin prepared in Example 3 to be described later is 1.
- composition ratio and the content are mass%.
- the total lipid content jumps to at least about three times this, so the content of phospholipids decreases evenly by a fraction.
- Freshly evacuated packaged chilled meat (produced by the Agricultural Union Act, artificial nuchikin) taken from waste eggs from egg-laying hens, preferably 1.2) described in mince 3 550 g, protein-treated natural preparation KO— X (Prepared by Osamu Kukino (Ichiki Kushikino Nashina 1126-1)) Dissolve 50 g in 2 50 ml of cold water, mix with refrigerated mince, and quickly with a food processor of a commercial home appliance. Then, 34.3 g of seasonings and spices were added and mixed well to obtain 6500 g of seasoned fillet minced meat (yield 95% by mass). This was deaerated and sealed and left in the refrigerator for several hours.
- Example 1 of waste chicken fillet 3. Extraction of 400 g of freeze-dried powder using the method described above using 100 mL of ethanol as an extraction solvent, followed by extraction The effluent was dried by a rotary evaporator to obtain 12 g of total lipids. Then, the dried total lipids, per the lg, 2 0111] ⁇ 1 1 over hexane / Aseton (volume ratio 1Z 1) mixed solvent was added and 1 hour extraction process under ice cooling. Thereafter, the extraction solution was centrifuged at 100 G for 10 minutes to separate the soluble portion and the precipitate (insoluble portion) of the supernatant.
- Example 1 1. 3) Concentrated and separated in the same manner as in Example 2 1. using 2 g of the total lipid obtained in (1) to obtain a concentrated phospholipid fraction of 1.4 g (yield 7 0%) was prepared. As a result of this HP L C_ ELSD analysis, [pi PC (70%) + 1 PE (30%)] 0.5 9 g (yield 4 2%) and [PC (9 4%) + PE ( 6%)] 0.69 g (yield 49.5%). 2) Female laying hens
- Example 1 1. 3) Concentrated and separated in the same manner as in Example 2 1. using 2 g of the total lipid obtained in (2). Rate 63.7%) was prepared. As a result of this HPLC / ELSD analysis, [pl PC (60%) + p1PE (4 0%)] 0.45 g (yield 35.3%) and [PC (9 0%) + It was found to be PE (1 0%)] 0.71 g (yield 55.7%).
- Fresh epidermis collected from waste chickens of egg-collecting hens was minced 8 mm under low temperature using the above-mentioned apparatus to obtain 4700 g (yield 94% by mass) of chicken skin mince. This was vacuum-packed with a high barrier film wrapping material and stored refrigerated. 300 g of this chicken skin minced is heated and deoiled minimally invasively at 105 ° C for 15 minutes with a low-oxygen hybrid steam heating device (made by Taiyoichi Seisakusho Co., Ltd. (Hito-Shimizugawa); hi-L0HS device). Thus, deoiled chicken skin 8 mm mince 14 45 g (yield 48 mass%) was obtained, vacuum-packed with a high barrier film packaging material, and stored refrigerated.
- Refrigerated seasoned minced meat minced 45 5 g with chilled deoiled chicken skin minced 50 g After mixing, fryer with meatball molding device (1700 ° CZ for 3 minutes) To give about 30 g of meatballs 4550 g (yield 90 mass%) in a half-fried state. This half-fried meatball is heated at the above-mentioned hi-L0HS 1 1 5 ° C for 5.5 minutes, then left for 5 minutes and left to heat (Fig. 4). 3% by mass) was obtained. This was allowed to cool at room temperature, and then stored in a deaerated package frozen.
- the frozen cooked chicken meat poles 10 pieces 2 95 5 g were thawed and heated in a microwave oven, and 2 9 2 g (yield 99% by mass) of hot chicken meat tops were obtained without dripping. .
- the hot chicken meat pole obtained above was subjected to a two-choice sensory test with 12 adult men and women. As shown in Table 2, a high score was obtained. There were many impressions that the fried food was not oily and refreshed, and the texture was soft and juicy, and the taste and aroma of chicken were delicious.
- composition ratio and the content are mass%.
- Oral phospholipids can be produced with high yield by simple operations.
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Abstract
La présente invention concerne un procédé de production d'une substance fonctionnelle contenant des phospholipides ou d'un glycérophospholipide de type plasmalogène de pureté élevée à partir d'une viande de poitrine de volaille par une manipulation simple et avec un rendement élevé. La présente invention concerne spécifiquement : un procédé de production d'une substance fonctionnelle contenant des phospholipides en transformant la forme d'une viande de poitrine de volaille par au moins un procédé choisi parmi les procédés suivants (a) à (c) : (a) un procédé de hachage de la viande de poitrine de volaille à faible température et dans une atmosphère avec un faible taux d'oxygène ; (b) un procédé d'empâtage de la viande de poitrine de volaille conjointement avec un agent émulsifiant/dispersant à faible température ; et (c) un procédé de mise en poudre de la viande de poitrine de volaille par un séchage à faible température ; et un procédé de production d'un glycérophospholipide de type plasmalogène, qui comprend les étapes suivantes (A) à (C) consistant à : (A) extraire la totalité de la substance grasse à partir d'une poudre d'une viande de poitrine de volaille et sécher la substance grasse extraite ; (B) extraire la totalité de la substance grasse séchée avec un solvant afin de séparer en une fraction insoluble et une fraction soluble ; et (C) extraire la fraction soluble avec un solvant afin de séparer et de collecter la fraction insoluble.
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