JP5774816B2 - Method for producing phospholipid-containing functional material and method for producing plasmalogen-type glycerophospholipid - Google Patents
Method for producing phospholipid-containing functional material and method for producing plasmalogen-type glycerophospholipid Download PDFInfo
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- JP5774816B2 JP5774816B2 JP2009516384A JP2009516384A JP5774816B2 JP 5774816 B2 JP5774816 B2 JP 5774816B2 JP 2009516384 A JP2009516384 A JP 2009516384A JP 2009516384 A JP2009516384 A JP 2009516384A JP 5774816 B2 JP5774816 B2 JP 5774816B2
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- glycerophospholipid
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- 150000002327 glycerophospholipids Chemical class 0.000 title claims description 64
- 150000003904 phospholipids Chemical class 0.000 title claims description 47
- 239000000463 material Substances 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 241000287828 Gallus gallus Species 0.000 claims description 66
- 150000002632 lipids Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 34
- 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 33
- 239000002904 solvent Substances 0.000 claims description 27
- 238000000605 extraction Methods 0.000 claims description 14
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 11
- 239000012046 mixed solvent Substances 0.000 claims description 10
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- 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
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- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
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- 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
- 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
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- 241001465754 Metazoa Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 230000013632 homeostatic process Effects 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000016273 neuron death Effects 0.000 description 2
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- 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
- 230000035945 sensitivity Effects 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003408 sphingolipids Chemical class 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 238000003860 storage Methods 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
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- 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
- 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 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 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
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 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
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003792 cranial nerve Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001982 diacylglycerols Chemical group 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 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
- 235000011194 food seasoning agent Nutrition 0.000 description 1
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- 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
- 150000002270 gangliosides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 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
- 125000003473 lipid group Chemical group 0.000 description 1
- 239000007788 liquid Substances 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
- 239000008204 material by function Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000002107 myocardial effect Effects 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 210000004003 subcutaneous fat Anatomy 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000001629 suppression Effects 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
Images
Classifications
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- 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
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Fodder In General (AREA)
Description
本発明は、家禽、特にニワトリのムネ肉から、機能性食品素材、医薬品素材、化粧品素材などとして有用なリン脂質含有機能性素材とプラズマローゲン型グリセロリン脂質を、簡単な操作で収率よく製造する方法、並びにプラズマローゲン型グリセロリン脂質に関するものである。 The present invention produces phospholipid-containing functional materials and plasmalogen-type glycerophospholipids that are useful as functional food materials, pharmaceutical materials, cosmetic materials, and the like from poultry, particularly chicken breast meat, with a simple operation and in high yield. The present invention relates to a method and a plasmalogen-type glycerophospholipid.
脂質とは、分子中に長鎖脂肪酸または類似の炭化水素鎖をもち、生体内に存在するか、生物に由来する物質を指す。この脂質は、単純脂質と複合脂質に分類することができる。単純脂質は、Ｃ、ＨおよびＯより構成され、一般にアセトンに可溶で、単純脂質のトリアシルグリセロールは動物体では、脂肪組織にエネルギーの貯蔵体として存在する。一方、複合脂質は、リン酸のＰや塩基のＮなどを含む脂質群である。したがって、複合脂質は、疎水性部分（脂肪酸部分）と親水性部分（リン酸や塩基の部分）からなり、両親媒性を示し、一般的には、前記単純脂質がアセトンに可溶であるのに対し、複合脂質はアセトンに不溶である。このような複合脂質は生体膜の構成成分となっている。
前記複合脂質は、（１）グリセロリン脂質［ホスファチジルコリン（別名レシチン）、ホスファチジルエタノールアミンなどが属する。］、（２）スフィンゴリン脂質（スフィンゴミエリン、セラミドシリアチンなどが属する。）、（３）スフィンゴ糖脂質（セレブロシド、スルファチド、ガングリオシドなどが属する。）、および（４）グロセロ糖脂質（微生物や高等植物に存在するジアシルグリセロールに種々の糖が結合したものなどがある。）に大別することができる。なお、前記（２）スフィンゴリン脂質および（３）のスフィンゴ糖脂質を総称してスフィンゴ脂質と呼ばれる。
前記グリセロリン脂質は、グリセロリン酸を骨格にもつリン脂質の総称で、ホスファチジルコリン（レシチン）、ホスファチジルエタノールアミン、ジホスフィチジルグリセロールなどがある。このグリセロリン脂質は、非極性部分が脂肪酸のエステルであるものが多いがビニルエーテル結合をもつプラズマローゲン型のものもある。
このグリセロリン脂質は、生体膜の構成成分として重要であるが、中でもプラズマローゲン型のグリセロリン脂質は、ビニルエーテル結合のラジカル感受性が高いため、抗酸化性を有するリン脂質として、近年注目されている。最近、プラズマローゲン型グリセロリン脂質が、細胞膜の抗酸化性分であるα−トコフェロール（ビタミンＥ）とは異なった機構により、コレステロールを含むリン脂質膜の酸化安定性に寄与していることが報告されており（例えば、「Ｊ．Ｌｉｐｉｄ Ｒｅｓ．」、第４４巻、第１６４〜１７１頁（２００３年）参照。）、またプラズマローゲン型グリセロリン脂質は、細胞膜やリポタンパク質の抗酸化性に関与するだけでなく、細胞の情報伝達システムに重要な役割を有することが指摘されている（例えば、「Ｊ．Ｍｏｌ．Ｎｅｕｒｏｓｃｉ．」、第１６巻、２６３〜２７２頁；ｄｉｓｃｕｓｓｉｏｎ ２７９〜２８４頁（２００１年）参照）。
このようなプラズマローゲン型グリセロリン脂質は、痴呆症における脳の神経細胞死を防止する作用が期待されているが、安全で大量に入手可能な供給源は見当たらないのが実状である。
ところで、食品、動物組織などの総脂質から比較的多量のスフィンゴミエリンを製造するためには、ケイ酸などを使用したカラムクロマトグラフィーで段階的に溶出して製造するか、あるいは、溶媒分画法で段階的に分画して製造されている。いずれも、複雑な手順が必要である。溶媒分画法では総脂質にアセトンを加えて複合脂質（リン脂質）を沈殿させ（不溶部）、その不溶部をエーテルで洗ってグリセロリン脂質を除いたものを粗スフィンゴ脂質画分とする方法が一般的である。この画分にはスフィンゴミエリンだけでなくセレブロシドなどのスフィンゴ糖脂質も含まれる。
鶏皮のリン脂質には、ヒト型スフィンゴミエリンおよびプラズマローゲン型グリセロリン資質が多く含まれていることが知られている。
鶏皮は、従来の原料源に比べ、ヒト型スフィンゴミエリンの原料としてその有用性が高いが、皮下脂肪が極めて多く、場合によっては７０質量％を超え、この除去が煩雑を極めるという問題がある。又、鶏皮にはヒト型スフィンゴミエリンと同レベルのプラズマローゲン型グリセロリン脂質が含まれ、そのホスファチジルコリン（レシチン）とホスファチジルエタノールアミンの割合は、後者が顕著に高いのが特徴である。
本発明者らは、鶏皮を凌ぐ原料の開発に鋭意取り組み、鶏肉、特にムネ肉中に中性脂質含量が鶏皮に比べ３０〜７０分の１レベルと極小で、ヒト型スフィンゴミエリンとプラズマローゲン型グリセロリン脂質合計の含有量が数倍の著量で、然も、プラズマローゲン型グリセロリン脂質とヒト型スフィンゴミエリンの割合が、前者が８５質量％強で、更に、プラズマローゲン型グリセロリン脂質の構成比が、成鶏では５０〜７５質量％がホスファチジルコリン、若鶏では逆に６割程度がホスファチジルエタノールアミンであり、成鶏中のプラズマローゲン型ホスファチジルコリン含有量は鶏皮の３０倍以上、若鶏中のプラズマローゲン型ホスファチジルエタノールアミンは鶏皮の２倍弱という、プラズマローゲン型グリセロリン脂質（２種混合）、プラズマローゲン型ホスファチジルコリン単体、及びプラズマローゲン型ホスファチジルエタノールアミン単体、各々の抽出原料として、従来その例を見ない費用対効果に優れた家禽肉のムネ肉を見出すことに成功した。
成鶏ムネ肉は、総脂質が１質量％と僅少で、その８割がリン脂質（中性脂質は０．２質量％と極小）であって、その内プラズマローゲン型グリセロリン脂質は４５質量％（その内の７割がプラズマローゲン型ホスファチジルコリン）で、生ムネ肉中の含有率は０．３６質量％（ヒト型スフィンゴミエリンは僅かに０．０３質量％）と高く、これを主材として加工するだけで付加価値の高い機能性食品を調製出来る。因みに、家禽ムネ肉は、もも肉と並んで採肉率が高いが、硬くてパサ付く食感とジューシー感に欠ける食味性のため、ヘルシーにも拘わらず長い間現在まで食肉としては低利用の扱いを受けている。年間間引かれる採卵廃鶏１億羽、２０万トンから採肉されるムネ肉は１５千トンに上り、国産畜肉として大事に利用することが強く求められる。A lipid refers to a substance having a long-chain fatty acid or a similar hydrocarbon chain in a molecule and existing in a living body or derived from an organism. These lipids 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, the complex lipid is a lipid group containing P of phosphate, N of base and the like. Therefore, the complex lipid is composed of a hydrophobic part (fatty acid part) and a hydrophilic part (phosphoric acid or base part) and exhibits 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 includes (1) glycerophospholipid [phosphatidylcholine (also known as lecithin), phosphatidylethanolamine, and the like. ], (2) sphingophospholipid (sphingomyelin, ceramide serialin, etc.), (3) glycosphingolipid (cerebrosid, sulfatide, ganglioside, etc.), and (4) gloeroglycolipid (microorganisms and higher). There are those in which various sugars are bound to diacylglycerols existing in plants, etc.). The (2) sphingophospholipid and the (3) sphingoglycolipid are collectively referred to as sphingolipids.
The glycerophospholipid is a general term for phospholipids having glycerophosphate as a skeleton, and includes phosphatidylcholine (lecithin), phosphatidylethanolamine, diphosphitidylglycerol, and the like. Many of these glycerophospholipids are non-polar moieties that are esters of fatty acids, but there are also plasmalogen types that have vinyl ether bonds.
This glycerophospholipid is important as a component of biological membranes. Among them, plasmalogen-type glycerophospholipid has recently attracted attention as an antioxidative phospholipid because of its high radical sensitivity of vinyl ether bond. Recently, it has been reported that plasmalogen-type glycerophospholipid contributes to oxidative stability of phospholipid membranes containing cholesterol by a mechanism different from that of α-tocopherol (vitamin E), which is an antioxidant component of cell membranes. (See, for example, “J. Lipid Res.”, Vol. 44, pp. 164-171 (2003)), and plasmalogen-type glycerophospholipids are only involved in the antioxidant properties of cell membranes and lipoproteins. However, it has been pointed out to have an important role in the cell information transmission system (for example, “J. Mol. Neurosci.”, Vol. 16, pp. 263 to 272; disclosure 279 to 284 (2001)). reference).
Such plasmalogen-type glycerophospholipid is expected to have an effect of preventing neuronal cell death of the brain in dementia, but in reality there are no sources that are safe and available in large quantities.
By the way, in order to produce a relatively large amount of sphingomyelin from total lipids of foods, animal tissues, etc., it is produced by elution stepwise by column chromatography using silicic acid or the like, or solvent fractionation method. It is manufactured by fractionating in stages. Both require complex procedures. In the solvent fractionation method, acetone is added to total lipids to precipitate complex lipids (phospholipids) (insoluble part), and the insoluble part is washed with ether to remove the glycerophospholipids to obtain a crude sphingolipid fraction. It is common. This fraction contains not only sphingomyelin but also glycosphingolipids such as cerebroside.
It is known that chicken skin phospholipids are rich in human sphingomyelin and plasmalogen glyceroline qualities.
Chicken skin is more useful as a raw material for human-type sphingomyelin than conventional raw material sources, but it has a large amount of subcutaneous fat, sometimes exceeding 70% by mass, and the removal is extremely complicated. . Chicken skin contains plasmalogen-type glycerophospholipid at the same level as human-type sphingomyelin, and the ratio of phosphatidylcholine (lecithin) and phosphatidylethanolamine is markedly higher in the latter.
The present inventors have eagerly developed a raw material that surpasses chicken skin, and the content of neutral lipids in chicken meat, particularly rice meat, is 30 to 70 times smaller than chicken skin, and human-type sphingomyelin and plasma. The total content of Rogen-type glycerophospholipid is a significant amount, but the ratio of plasmalogen-type glycerophospholipid and human-type sphingomyelin is more than 85% by mass, and the composition of plasmalogen-type glycerophospholipid. The ratio of phosphatidylcholine is 50 to 75% by mass in adult chickens, and conversely about 60% is phosphatidylethanolamine in young chickens, and the content of plasmalogen-type phosphatidylcholine in adult chickens is more than 30 times that of chicken skin, Plasmalogen-type phosphatidylethanolamine is less than twice as thick as chicken skin , Plasmalogen type phosphatidylcholine alone and plasmalogen-type phosphatidylethanolamine alone, as each of the extracted material, and succeeded in finding a breast excellent poultry to see not cost-effective conventional examples thereof.
Adult chicken meat is a little 1% by mass of total lipid, 80% of which is phospholipid (neutral lipid is 0.2% by mass), of which 45% by mass is plasmalogen glycerophospholipid. (70% of that is plasmalogen-type phosphatidylcholine), and the content of raw fillet meat is as high as 0.36% by mass (human-type sphingomyelin is only 0.03% by mass). A functional food with high added value can be prepared just by doing. By the way, poultry fillet has a high rate of harvesting along with thighs, but because of its hard and crunchy texture and lack of juiciness, it has been treated as low-use meat for a long time despite being healthy. Is receiving. Over 100 million chickens collected annually and 200,000 tons of minced meat are 15,000 tons, and it is strongly required to use them domestically.
本発明は、このような事情のもとで、家禽、特にニワトリのムネ肉から、プラズマローゲン型グリセロリン脂質を多く含有する機能性素材を製造する方法、及び家禽ムネ肉粉末、好ましくは上記機能性素材から純度の高いプラズマローゲン型グリセロリン脂質を、簡単な操作で収率よく製造する方法を提供することを目的とするものである。 Under such circumstances, the present invention provides a method for producing a functional material containing a large amount of plasmalogen-type glycerophospholipid from poultry, particularly chicken fillet, and poultry fillet powder, preferably the above-mentioned functionality. An object of the present invention is to provide a method for producing a high-purity plasmalogen-type glycerophospholipid from a raw material with a simple operation and with a high yield.
本発明者らは、前記目的を達成するために鋭意研究を重ねた結果、家禽、特に鶏のムネ肉に特定の工程を施すことにより、プラズマローゲン型グリセロリン脂質を多く含有する機能性素材が効率よく得られること、そして家禽ムネ肉粉末に特定の工程を施すことにより、純度の高いプラズマローゲン型グリセロリン脂質が効率よく得られることを見出し、この知見に基づいて本発明を完成するに至った。
すなわち、本発明は、
（１） 家禽ムネ肉を、（ａ）低温・低酸素雰囲気下でのミンチ化工程、（ｂ）乳化分散剤を用いた低温下でのペースト化工程および（ｃ）低温乾燥での粉末化工程の中から選ばれる少なくとも一つの工程によって形状変換することにより、リン脂質含有機能性素材を製造する方法であって、プラズマローゲン型グリセロリン脂質とスフィンゴミエリンとの合計量中の前者の含有割合が８５質量％以上であり、かつ総脂質中の全リン脂質の含有割合が４０質量％以上であるリン脂質含有機能性素材を得ることを特徴とする、リン脂質含有機能性素材の製造方法、
（２） 家禽ムネ肉が皮剥ぎムネ肉である上記（１）項に記載の方法、
（３） 家禽が成鶏（以下、廃鶏ということがある）であり、かつプラズマローゲン型グリセロリン脂質中のホスファチジルコリンとホスファチジルエタノールアミンの構成比率において、前者が４０質量％以上である、上記（１）または（２）項に記載の方法、
（４）家禽がブロイラー種鶏雌雄の成鶏であり、かつプラズマローゲン型グリセロリン脂質中のホスファチジルコリンとホスファチジルエタノールアミンの構成比率において、前者が５０質量％以上である、上記（１）または（２）項に記載の方法、
（５） 家禽がブロイラーであり、かつプラズマローゲン型グリセロリン脂質中のホスファチジルコリンとホスファチジルエタノールアミンの構成比率において、後者が５０質量％以上である、上記（１）または（２）項に記載の方法、
（６） （Ａ）家禽ムネ肉粉末から総脂質を抽出し、乾燥処理する工程、（Ｂ）前記（Ａ）工程で得られた乾燥総脂質を、脂肪族炭化水素系溶剤と水溶性ケトン系溶剤との混合溶剤で抽出処理し、不溶部と、プラズマローゲン型グリセロリン脂質を主体とする可溶部とに分離する工程、（Ｃ）前記（Ｂ）工程で得られた可溶部を乾燥処理後、水溶性ケトン系溶剤で抽出処理し、プラズマローゲン型グリセロリン脂質を主体とする不溶部を分離回収する工程、を含むことを特徴とするプラズマローゲン型グリセロリン脂質の製造方法、
（７） （Ｂ）工程における混合溶剤が、ｎ−ヘキサンとアセトンとを容量比４：６〜６：４の割合で含み、かつその使用量が、乾燥総脂質１ｇ当たり、１０〜３０ｍＬである上記（６）項に記載の方法、
（８） （Ｃ）工程における水溶性ケトン系溶剤がアセトンであり、その使用量が、（Ｂ）工程で得られた可溶部の乾燥処理物１ｇ当たり、１０〜３０ｍＬである上記（６）または（７）項に記載の方法、
（９） 上記（６）〜（８）項のいずれか１項に記載の方法を用いて得られたことを特徴とするプラズマローゲン型グリセロリン脂質、
を提供するものである。As a result of intensive studies to achieve the above object, the present inventors have made a functional material containing a large amount of plasmalogen-type glycerophospholipids by applying a specific process to poultry, especially chicken fillet. It has been found that a high-purity plasmalogen-type glycerophospholipid can be obtained efficiently by applying a specific process to the poultry fillet powder, and the present invention has been completed based on this finding.
That is, the present invention
(1) Poultry fillet, (a) Mincing step under low temperature and low oxygen atmosphere, (b) Pasting step under low temperature using emulsifying dispersant and (c) Powdering step under low temperature drying Is a method for producing a phospholipid-containing functional material by converting its shape by at least one process selected from among the above, wherein the former content ratio in the total amount of plasmalogen-type glycerophospholipid and sphingomyelin is 85 A method for producing a phospholipid-containing functional material, characterized in that the phospholipid-containing functional material is at least 40% by mass, and the total phospholipid content in the total lipid is 40% by mass or more,
(2) The method according to (1) above, wherein the poultry fillet is a peeled fillet,
(3) The above (1) wherein the poultry is an adult chicken (hereinafter sometimes referred to as abandoned chicken) and the former is 40% by mass or more in the constituent ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerophospholipid. ) Or the method according to (2),
(4) The above (1) or (2), wherein the poultry are adult broiler chickens and males, and the former is 50% by mass or more in the constituent ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerophospholipid The method according to the paragraph,
(5) The method according to (1) or (2) above, wherein the poultry is a broiler and the latter is 50% by mass or more in the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerophospholipid.
(6) (A) Extracting total lipid from poultry fillet powder and drying it, (B) Dry total lipid obtained in the above (A) step, aliphatic hydrocarbon solvent and water-soluble ketone Extracting with a mixed solvent with a solvent, separating the insoluble part into a soluble part mainly composed of plasmalogen-type glycerophospholipid, (C) drying the soluble part obtained in the step (B) A method for producing a plasmalogen-type glycerophospholipid, comprising: a step of performing extraction with a water-soluble ketone solvent and separating and recovering an insoluble part mainly composed of plasmalogen-type glycerophospholipid;
(7) 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 10 to 30 mL per 1 g of dry total lipid. The method according to (6) above,
(8) 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 dried product of the soluble part obtained in step (B) (6) Or the method according to (7),
(9) A plasmalogen-type glycerophospholipid obtained by using the method according to any one of (6) to (8) above,
Is to provide.
本発明によれば、家禽、特にニワトリのムネ肉から、機能性食品素材、医薬品素材、化粧品素材などとして有用な、プラズマローゲン型グリセロリン脂質とスフィンゴミエリンの構成比で前者が８割以上で、総脂質中の全リン脂質の割合が４割以上占めるリン脂質含有機能性素材を製造する方法、及び家畜ムネ肉粉末あるいは当該リン脂質含有機能性素材からプラズマローゲン型グリセロリン脂質、プラズマローゲン型ホスファチジルコリン単体、及びプラズマローゲン型ホスファチジルエタノールアミン単体を、簡単な操作で収率よく製造する方法、並びにこの方法で得られたプラズマローゲン型グリセロリン脂質、プラズマローゲン型ホスファチジルコリン単体、及びプラズマローゲン型ホスファチジルエタノールアミン単体を提供することができる。
本発明の家禽ムネ肉の形状変換技術、乳化分散天然製剤によるペースト化技術は、加熱処理で硬くならず、冷凍・解凍処理でも副生ドリップがなくジューシー感を保つ副次的機能を有する故、当該ムネ肉ペーストはムネ肉の高付加価値化食材として極めて有用であり、本発明がムネ肉の高付加価値化の端緒となって、その消費が拡大される結果として人々の健康増進に貢献するものと期待される。According to the present invention, the composition ratio of plasmalogen-type glycerophospholipid and sphingomyelin is useful as a functional food material, pharmaceutical material, cosmetic material, etc. from poultry, especially chicken breast meat. A method for producing a phospholipid-containing functional material in which the proportion of total phospholipids in the lipid is 40% or more, and livestock breast meat powder or the phospholipid-containing functional material, plasmalogen-type glycerophospholipid, plasmalogen-type phosphatidylcholine alone, And plasmalogen-type phosphatidylethanolamine simple substance with high yield, and plasmalogen-type glycerophospholipid, plasmalogen-type phosphatidylcholine simple substance, and plasmalogen-type phosphatidylethanolamine simple substance obtained by this method are provided. Do Door can be.
The shape conversion technology of poultry meat of the present invention, paste-making technology by emulsified dispersion natural preparation, because it does not become hard by heat treatment, and has a secondary function of maintaining a juicy feeling without by-product drip even in freezing and thawing treatment, The breast paste is extremely useful as a high-value-added food material for breast meat, and the present invention contributes to the promotion of people's health as a result of expanding the consumption of the high-value-added meat meat. Expected.
本発明のリン脂質含有機能性素材の製造方法は、以下に示す（ａ）工程、（ｂ）工程および（ｃ）工程の中から遺ばれる少なくとも一つの工程から構成されており、プラズマローゲン型グリセロリン脂質の製造方法は、（Ａ）工程、（Ｂ）工程および（Ｃ）工程から構成されている。
まず、本発明のリン脂質含有機能性素材の製造方法について説明する。
［（ａ）工程］
この（ａ）工程は、低温・低酸素雰囲気下でのミンチ化工程である。
当該（ａ）工程では、家禽ムネ肉、特に鶏ムネ肉、皮付きの場合には先ずスキナー処理で皮を剥いた後、常法通りミンチ化するが、その際に、ムネ肉の品温を低く、好ましくは５℃以下に冷却し、ミンチ化サイズとミンチ化速度も細断部の局所的な発熱を回避することを優先させて設定することが望ましい。又、ミンチ化後のミンチ肉と空気暴露を最少化させ、更に、空気酸化と雑菌感染を抑制するため空気清浄化装置付きの、室温を低く、好ましくは１５℃以下の準密閉空間内で当該処理とその密封包装を実施することが好ましい。得られたミンチは、ハイバリアー性フィルムで真空包装し、冷蔵保存するのがよい。
［（ｂ）工程］
この（ｂ）工程は、乳化分散剤を用いた低温下でのペースト化工程である。
当該（ｂ）工程では、皮剥きムネ肉、好ましくは、上記（ａ）工程でミンチ化処理後真空包装冷蔵保管された肉に、好ましくは非酵素系の蛋白質食材用乳化分散化天然製剤を適量の水で溶解させた水溶液を添加して、適宜なカッターやミキサー乃至はプロセッサーで均一に混合してペースト化（ストレートタイプ）後、場合により適量の香辛料等を加えて分散混合させて調味済みタイプとし、このペーストをハイバリアー性のフィルムで真空包装後冷却して、低温、好ましくは冷蔵保管するのがよい。長期間保管には冷凍も可能である。
［（ｃ）工程］
この（ｃ）工程は、低温乾燥での粉末化工程である。
当該（ｃ）工程では、皮剥きムネ肉、好ましくは上記（ａ）工程で真空包装冷蔵保管されたミンチ肉、場合によっては、上記（ｂ）工程のストレートタイプペーストの何れかを常法に従い市販の凍結乾燥装置で適宜に低侵襲的に乾燥し、必要により低温粉砕により粉末化し、この粉末をハイバリアー性フィルム真空包装後遮光下で冷蔵保管するのがよい。
このようにして得られたリン脂質含有機能性素材においては、プラズマローゲン型グリセロリン脂質とスフィンゴミエリンとの合計量中の前者の含有割合が８５質量％以上であり、かつ総脂質中の全リン脂質の含有割合が４０質量％以上である。
また、家禽が成鶏である場合、プラズマローゲン型グリセロリン脂質中のホスファチジルコリンとホスファチジルエタノールアミンの構成比率は、前者が５０質量％以上であり、ブロイラー種鶏雌雄の成鶏である場合、プラズマローゲン型グリセロリン脂質中のホスファチジルコリンとホスファチジルエタノールアミンの構成比率は、前者が５０質量％以上であり、ブロイラーである場合、プラズマローゲン型グリセロリン脂質中のホスファチジルコリンとホスファチジルエタノールアミンの構成比率は、後者が５０質量％以上である。
次に、本発明のプラズマローゲン型グリセロリン脂質の製造方法について説明する。
［（Ａ）工程］
この（Ａ）工程は、家禽ムネ肉粉末、好ましくは鶏ムネ肉粉末から総脂質を抽出し、乾燥処理する工程である。当該（Ａ）工程においては、まず、家禽ムネ肉粉末を調製するが、その場合、ニワトリムネ肉をそのまま乾燥・粉末化してもよいし、必要に応じ、ミンチ化、及びペースト化処理して、乾燥・粉末化してもよい。好ましくは、前記［（ｃ）工程］で得られるハイバリアー性フィルム真空包装後遮光下で冷蔵保管した粉末を使う。
次いで、このようにして得られた家禽ムネ肉粉末から、溶剤を用いて、総脂質を抽出し、乾燥処理して、乾燥総脂質を得る。総脂質の抽出に用いる溶剤としては、食品衛生上安全であって、かつ抽出効率のよいものが用いられる。このような溶剤としては、特にエタノールが好適である。この抽出処理は、常法に従って行うことができる。ただし、この抽出工程ではエタノール可溶の非脂質成分も抽出される。
抽出液は、常法に従い、ロータリエバポレーターなどを用いて溶剤を留去させることにより、あるいは窒素ガスを導入することなどにより、乾燥総脂質が得られる。
［（Ｂ）工程］
この（Ｂ）工程は、前記（Ａ）工程で得られた乾燥総脂質を、脂肪族炭化水素系溶剤と水溶性ケトン系溶剤との混合溶剤で抽出処理し、不溶部と、可溶部とに分離する工程である。
当該（Ｂ）工程において、乾燥総脂質の抽出処理に用いられる混合溶剤の一成分である脂肪族系炭化水素系溶剤としては、例えばｎ−ペンタン、イソペンタン、ｎ−ヘキサン、イソヘキサン、ｎ−ヘプタン、イソヘプタン、シクロペンタン、シクロヘキサンなどが挙げられ、これらは１種を単独で用いてもよく、２種以上を混合して用いてもよいが、これらの中でｎ−ヘキサンが好適である。
また、前記混合溶剤の他方の成分である水溶性ケトン系溶剤としては、例えばアセトンおよび／またはメチルエチルケトンなどを用いることができるが、これらの中でアセトンが好適である。
混合溶剤として、ｎ−ヘキサンとアセトンとの混合物を用いる場合、その割合は、容量比で４：６〜６：４が好ましく、４．５：５．５〜５．５：４．５がより好ましい。
また、この混合溶剤の使用量は、乾燥総脂質１ｇ当たり、通常１０〜３０ｍＬ程度である。
［（Ｃ）工程］
この（Ｃ）工程は、前記（Ｂ）工程で得られた可溶部を乾燥処理後、水溶性ケトン系溶剤で抽出処理し、プラズマローゲン型グリセロリン脂質を主体とする不溶部（以下、粗プラズマローゲン型グリセロリン脂質と称することがある。）を分離回収する工程である。
当該（Ｃ）工程においては、まず、前記（Ｂ）工程で得られた可溶部を、常法に従って乾燥処理する。例えばロータリエバポレーターを用いて、前記可溶部中の混合溶剤を留去させる方法などを用いることができる。次いで、このようにして得られた乾燥処理物を、水溶性ケトン系溶剤により、常法に従って抽出処理する。この際使用する水溶性ケトン系溶剤としては、アセトンおよび／またはメチルエチルケトンを挙げることができるが、アセトンが好適である。
抽出溶剤としてアセトンを使用する場合、乾燥処理物１ｇ当たり、通常１０〜３０ｍＬ程度である。溶剤の使用量が１０ｍＬ未満では、抽出処理を十分に行うことができず、不溶部中のプラズマローゲン型グリセロリン脂質の純度低下や回収率の低下を招くおそれがある。一方３０ｍＬを超えると、その量の割にはプラズマローゲン型グリセロリン脂質の純度や回収率の向上効果が発揮されにくい。溶剤の好ましい使用量は、乾燥処理物１ｇ当たり、１５〜２５ｍＬである。
抽出処理液は、遠心分離処理を施すことにより、可溶部とプラズマローゲン型グリセロリン脂質を主体とする不溶部（粗プラズマローゲン型グリセロリン脂質）に分離することができる。不溶部におけるプラズマローゲン型グリセロリン脂質の量は、通常４０質量％以上である。
このような本発明の方法によれば、家禽ムネ肉、好ましくは鶏ムネ肉の総脂質から、簡単な手段によって、プラズマローゲン型グリセロリン脂質を、高い純度で収率よく製造することができる。
本発明の方法によれば、鶏ムネ肉の乾燥粉末から、通常、粗プラズマローゲン型グリセロリン脂質を０．１〜３質量％程度の割合で得ることができる。
本発明の方法で得られる粗プラズマローゲン型グリセロリン脂質には、主としてホスファチジルコリン（ＰＣ）が含まれており、一部ホスファチジルエタノールアミン（ＰＥ）が含まれている。前記ＰＣは、約３０質量％がプラズマローゲン型であり、またＰＥには約６５質量％のプラズマローゲン型が含まれている。
下記の式（ＩＩ）および式（ＩＩＩ）に、それぞれジアシル型グリセロリン脂質およびプラズマローゲン型グリセロリン脂質の構造を示す。
なお、Ｘがアミノエチル基である場合、ホスファチジルエタノールアミンであり、Ｘがトリメチルアミノエチル基である場合、ホスファチジルコリンである。
前記プラズマローゲン型グリセロリン脂質は、ビニルエーテル結合のラジカル感受性が高いため抗酸化性リン脂質として注目されており、コレステロールを含むリン脂質膜の酸化安定性に寄与していることが知られている。またプラズマローゲン型グリセロリン脂質は、細胞膜やリポタンパク質の抗酸化性に関与するだけでなく、細胞の情報伝達システムに重要な役割を有することが指摘されている。このようなプラズマローゲン型グリセロリン脂質は、痴呆症における脳の神経細胞死を防止する作用や、アテローム性動脈硬化症の発症予防効果などが期待されている。
本発明はまた、前述した本発明の方法を用いて得られたことを特徴とするプラズマローゲン型グリセロリン脂質をも提供する。The method for producing a phospholipid-containing functional material of the present invention comprises at least one step left from among the following steps (a), (b) and (c), and comprises plasmalogen-type glyceroline: The method for producing lipid is composed of (A) step, (B) step and (C) step.
First, the manufacturing method of the phospholipid containing functional material of this invention is demonstrated.
[Step (a)]
This step (a) is a minching step under a low temperature and low oxygen atmosphere.
In the step (a), in the case of poultry fillet, especially chicken fillet, with skin, first skinned by skinner treatment and then minced as usual. It is desirable that the temperature is low, preferably cooled to 5 ° C. or less, and the minced size and minced rate are set with priority given to avoiding local heat generation at the shredded portion. In addition, to minimize minced meat and air exposure after mincing, and to suppress air oxidation and bacterial infection, the room temperature is low, preferably within 15 ° C or less in a semi-enclosed space. It is preferable to carry out the treatment and its sealed packaging. The obtained mince is preferably vacuum-packed with a high barrier film and stored refrigerated.
[Step (b)]
This step (b) is a pasting step at a low temperature using an emulsifying dispersant.
In the step (b), an appropriate amount of a non-enzymatic emulsion-dispersed natural preparation for protein foods is preferably added to the peeled minced meat, preferably the meat that has been minced in the step (a) and refrigerated and stored in a vacuum package. After adding an aqueous solution dissolved in water and mixing evenly with an appropriate cutter, mixer or processor to make a paste (straight type), add an appropriate amount of spices, etc. in some cases and disperse and mix to make a seasoned type The paste is cooled after being vacuum-packed with a high barrier film, and then stored at a low temperature, preferably refrigerated. Refrigeration is possible for long-term storage.
[(C) Step]
This step (c) is a powdering step by low temperature drying.
In the step (c), peeled meat, preferably minced meat refrigerated and vacuum-stored in the step (a), and in some cases, any of the straight type pastes in the step (b) is commercially available according to a conventional method. It is preferable to dry it in a minimally invasive manner with a freeze-drying apparatus, pulverize it by low-temperature pulverization if necessary, and store this powder refrigerated under light shielding after vacuum packaging of a high barrier film.
In the phospholipid-containing functional material thus obtained, the former content in the total amount of plasmalogen-type glycerophospholipid and sphingomyelin is 85% by mass or more, and the total phospholipid in the total lipid Is 40 mass% or more.
Further, when the poultry is an adult chicken, the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerophospholipid is 50% by mass or more, and when the poultry is a male and female broiler breeder, the plasmalogen type The composition ratio of phosphatidylcholine and phosphatidylethanolamine in the glycerophospholipid is 50% by mass or more for the former, and when it is a broiler, the composition ratio of phosphatidylcholine and phosphatidylethanolamine in the plasmalogen-type glycerophospholipid is 50% by mass for the latter. That's it.
Next, the manufacturing method of the plasmalogen type | mold glycerophospholipid of this invention is demonstrated.
[Step (A)]
This (A) process is a process of extracting and drying-processing total lipid from poultry fillet powder, preferably chicken fillet powder. In the step (A), first, poultry fillet powder is prepared. In that case, the chick trimet meat may be dried and powdered as it is, and if necessary, minced and pasted, and dried. -It may be pulverized. Preferably, the high barrier film vacuum packaging obtained in the above [(c) step] is used after refrigerated storage under light shielding.
Next, the total fat is extracted from the poultry fillet powder thus obtained using a solvent and dried to obtain dry total lipid. As a solvent used for extraction of total lipids, a solvent that is safe for food hygiene and has good extraction efficiency is used. 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 step.
As for the extract, a dry total lipid can be obtained by distilling off the solvent using a rotary evaporator or the like or introducing nitrogen gas according to a conventional method.
[Step (B)]
In the step (B), 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 part, a soluble part, It is the process of separating.
In the step (B), examples of the aliphatic hydrocarbon solvent that is one component of the mixed solvent used for the extraction treatment of the dry total lipid include n-pentane, isopentane, n-hexane, isohexane, n-heptane, Examples thereof include isoheptane, cyclopentane, cyclohexane, and the like. These may be used alone or in combination of two or more. Among these, n-hexane is preferred.
Moreover, as a water-soluble ketone solvent which is the other component of the mixed solvent, for example, acetone and / or methyl ethyl ketone can be used, and among these, acetone is preferable.
When a mixture of n-hexane and acetone is used as the mixed solvent, the ratio is preferably from 4: 6 to 6: 4, more preferably from 4.5: 5.5 to 5.5: 4.5. preferable.
Moreover, the usage-amount of this mixed solvent is about 10-30 mL normally per 1g of dry total lipids.
[Step (C)]
In the step (C), the soluble part obtained in the step (B) is dried and then extracted with a water-soluble ketone solvent, and an insoluble part (hereinafter, crude plasma) mainly composed of plasmalogen-type glycerophospholipid. This is a step of separating and collecting Rogen glycerophospholipid).
In the step (C), first, the soluble part obtained in the step (B) is dried according to a conventional method. For example, a method of distilling off the mixed solvent in the soluble part using a rotary evaporator can be used. Next, the dry-treated product thus obtained is extracted with a water-soluble ketone solvent according to a conventional method. Examples of the water-soluble ketone solvent used at this time include acetone and / or methyl ethyl ketone, and acetone is preferred.
When acetone is used as the extraction solvent, it is usually about 10 to 30 mL per 1 g of the dried product. If the amount of the solvent used is less than 10 mL, the extraction process cannot be sufficiently performed, and there is a possibility that the purity of the plasmalogen-type glycerophospholipid in the insoluble part is lowered and the recovery rate is lowered. On the other hand, if it exceeds 30 mL, the effect of improving the purity and recovery rate of the plasmalogen-type glycerophospholipid is hardly exhibited for the amount. The preferable usage-amount of a solvent is 15-25 mL per g of dry processed material.
The extraction treatment liquid can be separated into a soluble part and an insoluble part (crude plasmalogen-type glycerophospholipid) mainly composed of plasmalogen-type glycerophospholipid by performing a centrifugal separation treatment. The amount of plasmalogen-type glycerophospholipid in the insoluble part is usually 40% by mass or more.
According to such a method of the present invention, plasmalogen-type glycerophospholipid can be produced with high purity and high yield from the total fat of poultry fillet, preferably chicken fillet, by simple means.
According to the method of the present invention, a crude plasmalogen-type glycerophospholipid can be usually obtained at a ratio of about 0.1 to 3% by mass from a dry powder of chicken breast meat.
The crude plasmalogen glycerophospholipid obtained by the method of the present invention mainly contains phosphatidylcholine (PC), and partly contains phosphatidylethanolamine (PE). About 30% by mass of the PC is a plasmalogen type, and PE contains about 65% by mass of a plasmalogen type.
The structures of diacyl glycerophospholipid and plasmalogen glycerophospholipid are shown in the following formulas (II) and (III), respectively.
In addition, when X is an aminoethyl group, it is phosphatidylethanolamine, and when X is a trimethylaminoethyl group, it is phosphatidylcholine.
The plasmalogen-type glycerophospholipid has attracted 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. In addition, it has been pointed out that plasmalogen-type glycerophospholipid is not only involved in the antioxidant properties of cell membranes and lipoproteins, but also has an important role in the cell information transmission system. Such a plasmalogen type glycerophospholipid is expected to have an effect of preventing brain neuronal cell death in dementia, an onset prevention effect of atherosclerosis, and the like.
The present invention also provides a plasmalogen type glycerophospholipid obtained by using the above-described method of the present invention.
次に、本発明を実施例により、さらに詳細に説明するが、本発明は、これらの例によってなんら限定されるものではない。
実施例１
１．高次機能性リン脂質含有機能性ミンチ
１）有機農法育成採卵鶏の廃鶏のムネ肉
有機農法育成採卵鶏の廃鶏から採肉された新鮮な脱気包装冷蔵ムネ肉（農事組合法人エヌチキン（鹿児島県南九州市知覧町）製）（以下、「有機ムネ肉」と言うことがある。）１ｋｇを、工程中の空気暴露を最少化しながら空冷室内に設置した市販ミンチ装置でその装置内温度を１０℃以下に保持しながら数ｍｍサイズのミンチ処理を行い、９５質量％収率で得られたミンチを高バリア性フィルム包材に取り、直ちに脱気包装して冷蔵保管する。
該冷蔵ミンチを以下の成分分析に供した。
常法により該ミンチ１０ｇをＢｌｉｇｈ ＆ Ｄｙｅｒ法で抽出した総脂質２０６．２ｍｇをアセトン１０ｍｌで沈殿させて９９ｍｇの総リン脂質（含有率０．９９質量％）を得た。これをＨＰＬＣで分析し、蒸発光散乱法（ＥＬＳＤ）でそのピーク面積比から構成リン脂質の構成比を計算した。これを基にリン脂質分子の含有率とその含有量を求めて結果を表１に示した。
２）採卵廃鶏のムネ肉
１．１）と同様に、脂質分析を実施した。その結果を纏めて表２に示した。
３）ブロイラー種鶏雌雄の成鶏
（１）ブロイラー種鶏雄の成鶏
チャンキー種５羽（平均質量５．９ｋｇ）から採肉された脱気包装冷蔵の新鮮な皮剥きムネ肉（（農事組合法人）エヌチキン製）各々から２０ｇのサンプルを採取し、前記１）と同様に総脂質平均０．２ｇ（平均収率１％）を抽出した。各々の総脂質から平均７５質量％のリン脂質画分０．１５ｇを分離した。該リン脂質のＨＰＬＣ／ＥＬＳＤ分析による組成は、ｐｌＰＣ（２８．７％），ｐｌＰＥ（１１．２％），ＰＣ（４３．７％），ＰＥ（３．２％），ＳＭ（５．１％）で、ｐｌ型合計の構成比は３９．９％（ムネ肉中の含有率０．２８％）を示した。
（２）ブロイラー種鶏雌の成鶏
チャンキー種５羽（平均質量３．８ｋｇ）から採肉された脱気包装冷蔵の新鮮な皮剥きムネ肉（（農事組合法人）エヌチキン製）各々から２０ｇのサンプルを採取し、前記１）と同様に総脂質平均０．４７ｇ（平均収率２．３５％）を抽出した。各々の総脂質から平均６５質量％のリン脂質画分０．３ｇを分離した。該リン脂質のＨＰＬＣ／ＥＬＳＤ分析による組成は、ｐｌＰＣ（２１．４％），ｐｌＰＥ（１３．４％），ＰＣ（５０．３％），ＰＥ（４．８％），ＳＭ（１．３％）で、ｐｌ型合計の構成比は３５％（ムネ肉中の含有率０．５４％）を示した。
４）若鶏のムネ肉
市販のブロイラーを調達して１．１）と同様に、脂質分析を実施した。その結果を纏めて表３に示した。若鶏（ブロイラー）のムネ肉リン脂質の特徴は、前２例の成鶏の場合と同様に、僅かに１質量％強の総脂質に占める割合が２／３と多く、総ＰＣが７割弱と最大，次いで総ＰＥが２割強である。高次機能型では、ＳＭが２質量％と低く、総ＰＥの７割弱がＰＬ−ＰＥである点は成鶏と類似しているが、総ＰＣの組成が前２例の成鶏の場合と異なり、ＰＬ−ＰＣの占める割合は１３質量％台と著減し、その含有率も１／３と低下している。
後述の実施例３で調製した脱油ミンチ皮を１．１）と同様に、脂質分析を実施した。その結果を纏めて表４に示した。
生表皮では、総脂質含有量が、少なくともこの３倍程度に跳ね上がるので、リン脂質類の含有率は一様に数分の一に著減する。
２．高次機能性リン脂質含有機能性ペーストの調製
採卵鶏の廃鶏から採肉された脱気包装冷蔵の新鮮なムネ肉（農事組合法人エヌチキン製）、好ましくは上記１．２）記載ミンチ３５０ｇに、蛋白質処理天然製剤ＫＯ−Ｘ（久木野修（いちき串木野市下名１１２６−１）調製）５０ｇを２５０ｍｌの冷水に溶解させて、冷蔵ミンチに加えて市販家電のフードプロセッサーで手早く混合し、均一なペースト状態になったら調味料・香辛料合わせて３４．３ｇを加えて良く混合して調味済みムネ肉ミンチ６５０ｇ（歩留り９５質量％）を得た。これを脱気密封して冷蔵庫内で数時間静置した。
３．ムネ肉の凍結乾燥
１．２）で調製・包装・保存した採卵廃鶏のムネ肉ミンチ１００ｇを常法通り、市販の凍結乾燥装置で凍結乾燥を施して、乾燥粉末ムネ肉３１．５ｇ（収率９８質量％）を得た。
実施例２ プラズマローゲン型グリセロリン脂質の濃縮と分離
１．廃鶏ムネ肉
廃鶏ムネ肉の実施例１−３．記載の方法で凍結乾燥した粉末４００ｇを、抽出溶剤としてエタノール１０００ｍＬを用いて抽出処理したのち、抽出液をロータリエバポレーターにより乾燥して、総脂質１２ｇを得た。
次いで、この乾燥総脂質に、その１ｇ当たり、２０ｍＬのｎ−ヘキサン／アセトン（容量比１／１）混合溶剤を加え、氷冷下に１時間抽出処理した。その後、抽出処理液を、１０００Ｇにて１０分間遠心処理して上清の可溶部と沈殿物（不溶部）を分離した。 次に、可溶部をロータリエバポレーターにより乾燥して得られた乾燥物に、その１ｇ当たり、２０ｍＬのアセトンを加えて抽出処理した。その後、抽出処理液を、１０００Ｇにて１０分間遠心処理して、上清の可溶部と沈殿物（不溶部）を分離した。不溶部として、スフィンゴミエリンが除かれたリン脂質画分８．６ｇが得られ、その大部分はプラズマローゲン型グリセロリン脂質（４５質量％）とＰＣ・ＰＥの混合物（４５質量％）であった。そのＨＰＬＣチャートを図１に示した。
２．有機育成採卵廃鶏のムネ肉
同上１．と同様に凍結乾燥粉末４００ｇを供試し、分離総脂質２５ｇから１０．８ｇのリン脂質画分を得た。そのＨＰＬＣ測定結果（図２）から主要成分はＰＬ−ＰＣ＋ＰＬ−ＰＥ（２８質量％）とＰＣ（５３質量％）であることが示された。
３．ブロイラー種鶏雌雄の成鶏
１）ブロイラー種鶏雄の成鶏
実施例１ １．３）（１）で得られた総脂質２ｇを用いて、実施例２ １．と同様に濃縮・分離処理を行って濃縮リン脂質画分１．４ｇ（収率７０％）を調製した。このＨＰＬＣ／ＥＬＳＤ分析の結果、［ｐｌＰＣ（７０％）＋ｐｌＰＥ（３０％）］０．５９ｇ（収率４２％）及び［ＰＣ（９４％）＋ＰＥ（６％）］０．６９ｇ（収率４９．５％）であることが判明した。
２）採卵鶏種鶏の廃鶏雌
実施例１ １．３）（２）で得られた総脂質２ｇを用いて、実施例２ １．と同様に濃縮・分離操作を行って濃縮リン脂質画分１．２７ｇ（収率６３．７％）を調製した。このＨＰＬＣ／ＥＬＳＤ分析の結果、［ｐｌＰＣ（６０％）＋ｐｌＰＥ（４０％）］０．４５ｇ（収率３５．３％）及び［ＰＣ（９０％）＋ＰＥ（１０％）］０．７１ｇ（収率５５．７％）であることが判明した。
４．若鶏（ブロイラー）のムネ肉
同上１．と同様に凍結乾燥粉末４００ｇを供試し、分離総脂質１３．５ｇから８．７ｇのリン脂質画分を得た。そのＨＰＬＣ測定結果（図３）から主要成分はＰＣ（６０質量％）とＰＬ−ＰＣ＋ＰＬ−ＰＥ（２３質量％）であることが示された。
実施例３ 高次機能性リン脂質含有機能性チキンミートボールの調製
１）ミンチ化脱油した採卵鶏廃鶏表皮の調製
採卵鶏の廃鶏から採取された新鮮表皮５００ｇ冷蔵品を前述装置で低温下８ｍｍミンチ化し４７０ｇ（収率９４質量％）の鶏皮ミンチを得た。これを高バリア性フィルム包材で真空パックして冷蔵保管した。この鶏皮ミンチ３００ｇを低酸素ハイブリッドスチーム加熱装置（（株）タイヨー製作所（北斗市清水川）製；ｈｉ−ＬＯＨＳ装置）で１０５℃１５分間低侵襲的に加熱脱油して脱油鶏皮８ｍｍミンチ１４５ｇ（収率４８質量％）を得、高バリア性フィルム包材で真空パックして冷蔵保管した。
２）チキンミートボールの調製
冷蔵調味済みムネ肉ミンチ４５０ｇに冷蔵脱油鶏皮ミンチ５０ｇを加えて混合後に、ミートボール成型装置付きフライヤー（１７０℃／３分間）に供給して、半揚げ状態の約３０ｇのミートボール４５０ｇ（収率９０質量％）を得た。この半揚げ状態のミートボール前記ｈｉ−ＬＯＨＳ１１５℃５．５分間加熱後に５分間静置して余熱加熱を施して（図４）、調理チキンミートボール４２０ｇ（収率９３質量％）を得た。これを室温で放冷後に、脱気包装冷凍保管した。
該冷凍調理済みチキンミートボール１０個２９５ｇを電子レンジ解凍・加温しドリップの副生なく２９２ｇ（収率９９質量％）のホットチキンミートボールが得られた。
３）冷凍・解凍チキンミートボールの官能試験
上記で得られたホットチキンミートボールを成人男女１２名で２択形式の官能試験を実施した。表２に示した様に、高いスコアが得られた。揚げ物にしては油っぽくなくさっぱりとして、歯ざわりがソフトでジューシー、鶏の味と香りがあって美味しいという感想が多かった。
冷凍チキンミートボールの脂質成分分析を行った。
表６に示した様に使用原料由来のヒト型スフィンゴミエリンとプラズマローゲン型グリセロリン脂質のラズマローゲン型ホスフィチジルコリン及びラズマローゲン型ホスファチジルエタノールアミンが損耗せずに冷凍チキンミートボール中に残存していることが明らかにされた。
Example 1
1. High-order functional phospholipid-containing functional mince 1) Organic farm-grown egg-laying chicken waste meat Fresh organically-developed egg-laying chicken chilled meat Manufactured by Chirancho, Minamikyushu City, Kagoshima Prefecture) (hereinafter sometimes referred to as “organic fillet meat”) 1kg of the temperature inside the device is set in a commercial mincing device installed in an air-cooled room while minimizing air exposure during the process. While maintaining the temperature at 10 ° C. or lower, a several mm size mince treatment is performed, the mince obtained in a yield of 95% by mass is taken up in a highly barrier film packaging material, immediately degassed and stored in a refrigerator.
The refrigerated mince was subjected to the following component analysis.
206.2 mg of total lipid obtained by extracting 10 g of the mince by the Bligh & Dyer method by a conventional method was precipitated with 10 ml of acetone to obtain 99 mg of total phospholipid (content 0.99% by mass). This was analyzed by HPLC, and the constituent ratio of constituent phospholipids was calculated from the peak area ratio by the evaporative light scattering method (ELSD). Based on this, the content of phospholipid molecules and the content thereof were determined, and the results are shown in Table 1.
2) Egg waste from chicken collection The lipid analysis was performed in the same manner as in 1.1). The results are summarized in Table 2.
3) Adult broiler breeder male and female (1) Adult broiler breeder male and fowl Freshly peeled meat with deaerated packaging chilled from 5 chunky breeds (average mass 5.9 kg) A 20 g sample was taken from each of the associations (produced by Enchikin) and an average total lipid of 0.2 g (average yield of 1%) was extracted in the same manner as in 1) above. An average of 75% by mass of the phospholipid fraction of 0.15 g was separated from each total lipid. The composition of the phospholipid by HPLC / ELSD analysis was plPC (28.7%), plPE (11.2%), PC (43.7%), PE (3.2%), SM (5.1%). ), The composition ratio of the pl-type total was 39.9% (content ratio in fillet 0.28%).
(2) Adult broiler breeder hens 20 g from each of freshly peeled chilled meat (development association) manufactured by Enchikin, extracted from 5 chunky breeds (average mass 3.8 kg) In the same manner as in 1) above, an average total lipid of 0.47 g (average yield of 2.35%) was extracted. From each total lipid, 0.3 g of an average 65 mass% phospholipid fraction was separated. The composition of the phospholipid by HPLC / ELSD analysis was as follows: plPC (21.4%), plPE (13.4%), PC (50.3%), PE (4.8%), SM (1.3% ), The composition ratio of the pl-type total was 35% (content ratio in the fillet 0.54%).
4) Young chicken breast meat A commercially available broiler was procured and lipid analysis was performed in the same manner as in 1.1). The results are summarized in Table 3. The characteristics of young chicken (broiler) fillet phospholipids, like the previous two adult chickens, accounted for only 2/3 of the total lipids of slightly over 1% by mass, with a total PC of 70%. Weak and maximum, then total PE is just over 20%. In the high-order functional type, SM is as low as 2% by mass, and almost 70% of the total PE is PL-PE, but it is similar to adult chickens. Unlike the case, the proportion occupied by PL-PC is markedly reduced to the 13% by mass range, and the content is also reduced to 1/3.
In the raw epidermis, the total lipid content jumps up to at least about three times, so that the content of phospholipids is uniformly reduced by a fraction.
2. Preparation of functional paste containing higher-order functional phospholipids Degassed and refrigerated fresh fillet (produced by Agricultural Union Co., Ltd.) taken from waste chickens of egg-laying hens, preferably 350 g of mince described in 1.2) above , 50g of protein-treated natural preparation KO-X (prepared by Osamu Kukino (Ichiki Kushikino Shimona 1126-1)) dissolved in 250 ml of cold water, added to refrigerated mince, and quickly mixed with a food processor of a commercial home appliance. When it was in a paste state, 34.3 g of seasonings and spices were added and mixed well to obtain 650 g of seasoned fillet mince (yield 95 mass%). This was deaerated and sealed and allowed to stand in the refrigerator for several hours.
3. 100g of minced minced chicken hen meat prepared, packaged and stored in lyophilized fillet 1.2) is freeze-dried using a commercial lyophilizer as usual, and 31.5 g of dried powdered meat (yield) 98 mass%) was obtained.
Example 2 Concentration and separation of plasmalogen glycerophospholipid Waste chicken fillet Example 1-3 of waste chicken fillet 400 g of the powder lyophilized by the method described above was extracted using 1000 mL of ethanol as an extraction solvent, and then the extract was dried by a rotary evaporator to obtain 12 g of total lipid.
Subsequently, 20 mL of a mixed solvent of n-hexane / acetone (
2.
3. Broiler breeder adult male and female 1) Broiler breeder male and adult Example 1 1.3) Example 2 using 2 g of the total lipid obtained in (1). Concentration / separation treatment was performed in the same manner as described above to prepare 1.4 g (yield 70%) of the concentrated phospholipid fraction. As a result of this HPLC / ELSD analysis, [plPC (70%) + plPE (30%)] 0.59 g (42% yield) and [PC (94%) + PE (6%)] 0.69 g (49. 5%).
2) Waste chicken female of egg-laying chicken breed Example 1 1.3) Example 2 using 2 g of the total lipid obtained in (2). Concentration / separation operations were performed in the same manner as above to prepare a concentrated phospholipid fraction 1.27 g (yield 63.7%). As a result of this HPLC / ELSD analysis, [plPC (60%) + plPE (40%)] 0.45 g (yield 35.3%) and [PC (90%) + PE (10%)] 0.71 g (yield) 55.7%).
4). Broiler chicken fillet as above 1. In the same manner as above, 400 g of freeze-dried powder was used to obtain a phospholipid fraction of 13.5 g to 8.7 g of separated total lipid. From the HPLC measurement results (FIG. 3), it was shown that the main components were PC (60 mass%) and PL-PC + PL-PE (23 mass%).
Example 3 Preparation of Functional Chicken Meatballs Containing Higher Functional Phospholipids 1) Preparation of Minced Deoiled Egg-Delivered Egg Collection Chicken Epidermis 500 g of fresh epidermis collected from the egg-laying hen's waste chicken was chilled at the above-mentioned temperature. The bottom minced 8 mm to obtain 470 g (yield 94 mass%) chicken skin mince. This was vacuum-packed with a high barrier film wrapping material and stored refrigerated. 300 g of this chicken skin mince was heated and deoiled minimally invasively at 105 ° C. for 15 minutes with a low-oxygen hybrid steam heating device (manufactured by Taiyo Mfg. Co., Ltd. (Shimizugawa, Hokuto); hi-LOHS device) and
2) Preparation of chicken meatballs Add 50g of chilled deoiled chicken skin minced to 450g of chilled seasoned minced meat minced meat and feed it to a fryer with a meatball molding device (170 ° C for 3 minutes). About 30 g of meatballs 450 g (
295 g of the frozen cooked chicken meatballs (295 g) were thawed and heated in a microwave oven to obtain 292 g (yield 99% by mass) of hot chicken meatballs without by-product of drip.
3) Sensory test of frozen and thawed chicken meatballs The hot chicken meatballs obtained above were 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, the texture was soft and juicy, and the taste and aroma of chicken were delicious.
As shown in Table 6, human-type sphingomyelin derived from raw materials used, and plasmalogen-type glycerophospholipid, raspomalogen-type phosphitidylcholine and raspomalogen-type phosphatidylethanolamine, remain in the frozen chicken meatballs without wear. It was revealed that
本発明のリン脂質含有機能性素材及びプラズマローゲン型グリセロリン脂質の製造方法によれば、機能性食品素材、医薬品素材、化粧品素材などとして有用なリン脂質含有機能性素材及びプラズマローゲン型グリセロリン脂質を、簡単な操作で収率よく製造することができる。 According to the method for producing a phospholipid-containing functional material and a plasmalogen-type glycerophospholipid of the present invention, a phospholipid-containing functional material and a plasmalogen-type glycerophospholipid useful as a functional food material, a pharmaceutical material, a cosmetic material, etc. It can be produced with high yield by a simple operation.
Claims (7)
（Ｂ）前記（Ａ）工程で得られた乾燥総脂質を、脂肪族炭化水素系溶剤と水溶性ケトン系溶剤との混合溶剤で抽出処理し、不溶部と、プラズマローゲン型グリセロリン脂質を主体とする可溶部とに分離する工程、
（Ｃ）前記（Ｂ）工程で得られた可溶部を乾燥処理後、水溶性ケトン系溶剤で抽出処理し、プラズマローゲン型グリセロリン脂質を主体とする不溶部を分離回収する工程、
を含むことを特徴とするプラズマローゲン型グリセロリン脂質の製造方法。 (A) a skinning breast chicken selected from adult chicken or spent hen, phospholipid-containing functional obtained by shape conversion by trituration step with mincing step and low temperature drying under low temperature and low oxygen atmosphere A process of extracting total lipid from the material and drying it,
(B) 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 mainly contains an insoluble portion and plasmalogen-type glycerophospholipid. Separating into soluble parts
(C) A step of drying the soluble part obtained in the step (B), followed by extraction with a water-soluble ketone solvent, and separating and recovering an insoluble part mainly composed of plasmalogen-type glycerophospholipid,
A method for producing a plasmalogen-type glycerophospholipid, comprising:
The method according to claim 1 or 5 , wherein the chicken is an egg-laying waste chicken.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10653708B2 (en) | 2017-06-16 | 2020-05-19 | Institute of Rheological Functions of Food | Uses of ether phospholipids in treating diseases |
| US11066432B2 (en) | 2014-12-08 | 2021-07-20 | Institute of Rheological Functions of Food | Ether phospholipids and method for producing the same |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5430566B2 (en) * | 2008-06-20 | 2014-03-05 | 有限会社梅田事務所 | Method for producing high purity phospholipid and high purity sphingomyelin and plasmalogen glycerophospholipid obtained by the method |
| WO2010047404A1 (en) * | 2008-10-24 | 2010-04-29 | 有限会社梅田事務所 | Method for producing functional dried material having room temperature storage stability or ground product thereof and extraction fraction of the material or the ground product, and use of the material, the ground product or the extraction fraction |
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| KR20190003570A (en) * | 2016-05-02 | 2019-01-09 | 우메다 지무쇼 리미티드 | Methods for Determining Infectious Conditions of Safe, Stable Plasma Genogens, Agents and Dyslipidemia |
| WO2017191838A1 (en) * | 2016-05-02 | 2017-11-09 | 有限会社梅田事務所 | Safe and stable plasmalogen, formulation thereof, and method for assessing presymptomatic state of dementia |
| JP6603923B2 (en) * | 2016-05-02 | 2019-11-13 | 有限会社梅田事務所 | A chicken breast-derived plasmalogen composition having an effect of improving cognitive function, and a food composition or supplement for improving and / or improving cognitive function comprising the composition |
| JP6542408B1 (en) | 2018-02-21 | 2019-07-10 | 丸大食品株式会社 | Phospholipid concentrate production method |
| JP6585749B2 (en) | 2018-02-21 | 2019-10-02 | 丸大食品株式会社 | Method for producing phospholipid concentrate |
| US11517594B2 (en) * | 2018-03-08 | 2022-12-06 | Nihon Pharmaceutical Co., Ltd. | Methods for producing compositions containing plasmalogen |
Citations (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5350358A (en) * | 1976-10-16 | 1978-05-08 | Nippon Suisan Kaisha Ltd | Method of producing process food |
| JPS59220168A (en) * | 1983-05-27 | 1984-12-11 | Taiyo Fishery Co Ltd | Preparation of pasty protein food or protein ingredient |
| JPS6360979B2 (en) * | 1985-03-28 | 1988-11-28 | ||
| JPH01179667A (en) * | 1988-01-06 | 1989-07-17 | Toyo Jozo Co Ltd | Paste product of low-fat meat and preparation thereof |
| JPH02145156A (en) * | 1988-11-28 | 1990-06-04 | Hosokawa Micron Corp | Crushing method for food materials |
| JPH03273096A (en) * | 1990-03-20 | 1991-12-04 | Sumitomo Seika Chem Co Ltd | Method for extraction of lipid mixture |
| JPH07250614A (en) * | 1994-03-14 | 1995-10-03 | Nippon Sanso Kk | Method for individually freezing mince-like food and apparatus therefor |
| JPH0970239A (en) * | 1995-09-05 | 1997-03-18 | Kazuto Hattori | Poultry farming with saved energy by utilizing culled chicken regenerated with wild grass |
| JPH09275947A (en) * | 1996-04-15 | 1997-10-28 | Ito Ham Kk | Production of instant meat soup having form of mashed meat |
| JPH09308459A (en) * | 1996-05-20 | 1997-12-02 | Nof Corp | Nutritive composition containing highly unsaturated fatty acid |
| JPH11103766A (en) * | 1997-10-06 | 1999-04-20 | Ishii Shokuhin Kk | Production of chicken mince |
| JP2002045155A (en) * | 2000-08-04 | 2002-02-12 | National Food Research Institute | New reconstitutable concentrated extract having normal temperature storage stability and method for producing the same |
| JP2003102436A (en) * | 2001-09-28 | 2003-04-08 | New Food Creation Gijutsu Kenkyu Kumiai | Substance of chicken essence treated with membrane and method for producing the same |
| JP2004008188A (en) * | 2002-06-04 | 2004-01-15 | Asahi Broiler:Kk | Snack food from chicken as raw material, having new palatability and taste and method for producing the same |
| JP2004141146A (en) * | 2002-08-27 | 2004-05-20 | Sanei Gen Ffi Inc | Livestock meat-processed food |
| JP2004154028A (en) * | 2002-11-05 | 2004-06-03 | Ezaki Glico Co Ltd | Method for producing roux |
| JP2004522426A (en) * | 2000-11-27 | 2004-07-29 | サイトキネティクス | Cofilin of Aspergillus fumigatus |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60170700A (en) * | 1984-02-15 | 1985-09-04 | 鈴木 康夫 | Method of obtaining higher fatty acid |
| JPH0488963A (en) * | 1990-08-02 | 1992-03-23 | Sagami Chem Res Center | Functional healthy food and feed |
| JP2001164286A (en) * | 1999-12-10 | 2001-06-19 | Nof Corp | Oil and fat composition |
| JP2004002663A (en) * | 2002-03-29 | 2004-01-08 | Shizuoka Prefecture | Method for extracting lipid composition containing phospholipid with polyunsaturated fatty acid as constituent from fish internal organ |
| JP4549719B2 (en) * | 2004-04-05 | 2010-09-22 | キユーピー株式会社 | Method for producing phospholipid composition and pharmaceutical composition, cosmetic composition, or food composition using the same |
| JP5185539B2 (en) * | 2007-01-26 | 2013-04-17 | 有限会社梅田事務所 | Method for producing sphingomyelin and plasmalogen-type glycerophospholipid |
-
2008
- 2008-05-27 JP JP2009516384A patent/JP5774816B2/en active Active
- 2008-05-27 WO PCT/JP2008/060120 patent/WO2008146942A1/en active Application Filing
Patent Citations (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5350358A (en) * | 1976-10-16 | 1978-05-08 | Nippon Suisan Kaisha Ltd | Method of producing process food |
| JPS59220168A (en) * | 1983-05-27 | 1984-12-11 | Taiyo Fishery Co Ltd | Preparation of pasty protein food or protein ingredient |
| JPS6360979B2 (en) * | 1985-03-28 | 1988-11-28 | ||
| JPH01179667A (en) * | 1988-01-06 | 1989-07-17 | Toyo Jozo Co Ltd | Paste product of low-fat meat and preparation thereof |
| JPH02145156A (en) * | 1988-11-28 | 1990-06-04 | Hosokawa Micron Corp | Crushing method for food materials |
| JPH03273096A (en) * | 1990-03-20 | 1991-12-04 | Sumitomo Seika Chem Co Ltd | Method for extraction of lipid mixture |
| JPH07250614A (en) * | 1994-03-14 | 1995-10-03 | Nippon Sanso Kk | Method for individually freezing mince-like food and apparatus therefor |
| JPH0970239A (en) * | 1995-09-05 | 1997-03-18 | Kazuto Hattori | Poultry farming with saved energy by utilizing culled chicken regenerated with wild grass |
| JPH09275947A (en) * | 1996-04-15 | 1997-10-28 | Ito Ham Kk | Production of instant meat soup having form of mashed meat |
| JPH09308459A (en) * | 1996-05-20 | 1997-12-02 | Nof Corp | Nutritive composition containing highly unsaturated fatty acid |
| JPH11103766A (en) * | 1997-10-06 | 1999-04-20 | Ishii Shokuhin Kk | Production of chicken mince |
| JP2002045155A (en) * | 2000-08-04 | 2002-02-12 | National Food Research Institute | New reconstitutable concentrated extract having normal temperature storage stability and method for producing the same |
| JP2004522426A (en) * | 2000-11-27 | 2004-07-29 | サイトキネティクス | Cofilin of Aspergillus fumigatus |
| JP2003102436A (en) * | 2001-09-28 | 2003-04-08 | New Food Creation Gijutsu Kenkyu Kumiai | Substance of chicken essence treated with membrane and method for producing the same |
| JP2004008188A (en) * | 2002-06-04 | 2004-01-15 | Asahi Broiler:Kk | Snack food from chicken as raw material, having new palatability and taste and method for producing the same |
| JP2004141146A (en) * | 2002-08-27 | 2004-05-20 | Sanei Gen Ffi Inc | Livestock meat-processed food |
| JP2004154028A (en) * | 2002-11-05 | 2004-06-03 | Ezaki Glico Co Ltd | Method for producing roux |
Non-Patent Citations (3)
| Title |
|---|
| JPN6013028913; Ｉｎｔ Ｊ Ｆｏｏｄ Ｓｃｉ Ｔｅｃｈｎｏｌ， （１９９１）， Ｖｏｌ．２６， Ｎｏ．４，, Ｐ．３６３-３７１ * |
| JPN6013028914; Ｉｎｔ Ｊ Ｆｏｏｄ Ｓｃｉ Ｔｅｃｈｎｏｌ， （１９９０）， Ｖｏｌ．２５， Ｎｏ．３，, Ｐ．３０４-３１２ * |
| JPN6013028915; 日本食品科学工学会大５３回大会講演集， （２００６）， , Ｐ．７７ * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11066432B2 (en) | 2014-12-08 | 2021-07-20 | Institute of Rheological Functions of Food | Ether phospholipids and method for producing the same |
| US10653708B2 (en) | 2017-06-16 | 2020-05-19 | Institute of Rheological Functions of Food | Uses of ether phospholipids in treating diseases |
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| Publication number | Publication date |
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| JPWO2008146942A1 (en) | 2010-08-19 |
| WO2008146942A1 (en) | 2008-12-04 |
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