JP5185539B2 - 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脂質の製造方法 - Google Patents
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脂質の製造方法 Download PDFInfo
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- JP5185539B2 JP5185539B2 JP2007016056A JP2007016056A JP5185539B2 JP 5185539 B2 JP5185539 B2 JP 5185539B2 JP 2007016056 A JP2007016056 A JP 2007016056A JP 2007016056 A JP2007016056 A JP 2007016056A JP 5185539 B2 JP5185539 B2 JP 5185539B2
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- 150000002327 glycerophospholipids Chemical class 0.000 title claims description 42
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 68
- 150000002632 lipids Chemical class 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 25
- 238000000605 extraction Methods 0.000 claims description 19
- 241000287828 Gallus gallus Species 0.000 claims description 18
- 150000002576 ketones Chemical class 0.000 claims description 17
- 239000012046 mixed solvent Substances 0.000 claims description 17
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- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 9
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- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
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- 206010012289 Dementia Diseases 0.000 description 2
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- 230000016273 neuron death Effects 0.000 description 2
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- DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 description 2
- 150000003410 sphingosines Chemical class 0.000 description 2
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- QQVDJLLNRSOCEL-UHFFFAOYSA-N (2-aminoethyl)phosphonic acid Chemical compound [NH3+]CCP(O)([O-])=O QQVDJLLNRSOCEL-UHFFFAOYSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-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
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AERBNCYCJBRYDG-UHFFFAOYSA-N D-ribo-phytosphingosine Natural products CCCCCCCCCCCCCCC(O)C(O)C(N)CO AERBNCYCJBRYDG-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
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- ZQQLMECVOXKFJK-NXCSZAMKSA-N N-octadecanoylsphingosine 1-phosphate Chemical class CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(O)(O)=O)[C@H](O)\C=C\CCCCCCCCCCCCC ZQQLMECVOXKFJK-NXCSZAMKSA-N 0.000 description 1
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- 238000010828 elution Methods 0.000 description 1
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- 230000003020 moisturizing effect Effects 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- AERBNCYCJBRYDG-KSZLIROESA-N phytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO AERBNCYCJBRYDG-KSZLIROESA-N 0.000 description 1
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- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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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
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
Description
「J.Lipid Res.」、第44巻、第164〜171頁(2003年) 「J.Mol.Neurosci.」、第16巻、263〜272頁;discussion 279〜284頁(2001年)
(1) (A)鶏皮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、スフィンゴミエリンを主体とする不溶部と、可溶部とに分離する工程、(C)前記(B)工程で得られたスフィンゴミエリンを主体とする不溶部を、水と水溶性ケトン系溶剤との混合溶剤で抽出処理し、可溶部に含まれる非脂質成分を除去する工程、(D)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脂質の製造方法、
(2) (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(1)項に記載の方法、
(3) (C)工程における水溶性ケトン系溶剤がアセトンであり、水とアセトンとを容量比3:7〜7:3の割合で含み、かつその使用量が、(B)工程で得られたスフィンゴミエリンを主体とする不溶部の乾燥処理物1g当たり、10〜30mLである上記(1)または(2)項に記載の方法、および
(4) (D)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(1)または(2)項に記載の方法、
を提供するものである。
[(A)工程]
この(A)工程は、鶏皮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、鶏皮粉末を調製するが、その場合、ニワトリ表皮をそのまま粉末化してもよいし、必要に応じ、脱脂処理し、脂肪分をある程度除去したのち、粉末化してもよい。ニワトリ表皮の脱脂処理には、機械的方法、温水浸漬加熱方法、直接加熱方法、脂肪族炭化水素系溶媒(n−ヘキサン)による方法などを採用することができる。
[(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、スフィンゴミエリンを主体とする不溶部(以下、粗スフィンゴミエリンと称することがある。)と、可溶部とに分離する工程である。
この(C)工程は、前記(B)工程で得られたスフィンゴミエリンを主体とする不溶部を、水と水溶性ケトン系溶剤との混合溶剤で抽出処理し、可溶部に含まれる非脂質成分を除去する工程である。
[(D)工程]
この(D)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。
の構造を有し、通常動物体の脳組織のみならず、臓器組織にも広く存在する。
実施例1
鶏皮の凍結乾燥粉末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80gを得た。
(注。ELSD、エバポレイト光散乱;UV、紫外線;PC、ホスフィチジルコリン;SM、スフィンゴミエリン;PE、ホスファチジルエタノールアミン;PS、ホスファチジルセリン;PI、ホスフィチジルイニシトール;LPC、リゾホスファチジルコリン;LPE、リゾホスファチジルエタノールアミン)。
Claims (4)
- (A)鶏皮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、スフィンゴミエリンを主体とする不溶部と、可溶部とに分離する工程、(C)前記(B)工程で得られたスフィンゴミエリンを主体とする不溶部を、水と水溶性ケトン系溶剤との混合溶剤で抽出処理し、可溶部に含まれる非脂質成分を除去する工程、(D)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脂質の製造方法。
- (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である請求項1に記載の方法。
- (C)工程における水溶性ケトン系溶剤がアセトンであり、水とアセトンとを容量比3:7〜7:3の割合で含み、かつその使用量が、(B)工程で得られたスフィンゴミエリンを主体とする不溶部の乾燥処理物1g当たり、10〜30mLである請求項1または2に記載の方法。
- (D)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である請求項1または2に記載の方法。
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JP2007016056A JP5185539B2 (ja) | 2007-01-26 | 2007-01-26 | 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脂質の製造方法 |
CA002676484A CA2676484A1 (en) | 2007-01-26 | 2008-01-23 | Process for producing sphingomyelin and plasmalogen-form glycerophospholipid |
PCT/JP2008/051329 WO2008091015A1 (ja) | 2007-01-26 | 2008-01-23 | 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脂質の製造方法 |
US12/523,778 US8236978B2 (en) | 2007-01-26 | 2008-01-23 | Process for producing sphingomyelin and plasmalogen-form glycerophospholipid |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2671346C1 (ru) * | 2015-09-09 | 2018-10-30 | Ниссан Мотор Ко., Лтд. | Способ изготовления композиционного материала и устройство изготовления композиционного материала |
RU2671338C1 (ru) * | 2015-09-09 | 2018-10-30 | Ниссан Мотор Ко., Лтд. | Способ изготовления композиционного материала, устройство для изготовления композиционного материала и заготовка для композиционного материала |
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 |
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JP5774816B2 (ja) * | 2007-05-28 | 2015-09-09 | 有限会社梅田事務所 | リン脂質含有機能性素材の製造方法およびプラズマローゲン型グリセロリン脂質の製造方法 |
US8524282B2 (en) | 2008-06-20 | 2013-09-03 | Umeda Jimusho Ltd. | Method for production of highly pure phospholipid, and highly pure sphingomyelin and plasmalogen-type glycerophospholipid produced by the method |
JP5489439B2 (ja) * | 2008-09-11 | 2014-05-14 | 丸大食品株式会社 | プラズマローゲン型リン脂質及びスフィンゴ脂質の製造方法 |
WO2010131718A1 (ja) * | 2009-05-13 | 2010-11-18 | 丸大食品株式会社 | 鳥皮由来スフィンゴミエリン含有物を有効成分とする抗高血糖及び/又は抗高脂血症剤 |
WO2011083853A1 (ja) * | 2010-01-08 | 2011-07-14 | 丸大食品株式会社 | 抗アトピー性皮膚炎剤 |
EP2620154A4 (en) * | 2010-09-24 | 2014-02-19 | Fujino Brain Res Co Ltd | MEDICAMENT AGAINST IGNITION OF THE CENTRAL NERVOUS SYSTEM |
US20210077539A1 (en) * | 2018-05-16 | 2021-03-18 | Acasti Pharma Inc. | Process for the manufacture of enriched phospholipid compositions |
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JP5062873B2 (ja) * | 2005-02-24 | 2012-10-31 | 有限会社梅田事務所 | 複合脂質画分、それから単離されたヒト型スフィンゴミエリンとプラズマローゲンならびにこれらを含む機能性食品素材、医薬品素材および化粧品素材 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US11066432B2 (en) | 2014-12-08 | 2021-07-20 | Institute of Rheological Functions of Food | Ether phospholipids and method for producing the same |
RU2671346C1 (ru) * | 2015-09-09 | 2018-10-30 | Ниссан Мотор Ко., Лтд. | Способ изготовления композиционного материала и устройство изготовления композиционного материала |
RU2671338C1 (ru) * | 2015-09-09 | 2018-10-30 | Ниссан Мотор Ко., Лтд. | Способ изготовления композиционного материала, устройство для изготовления композиционного материала и заготовка для композиционного материала |
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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WO2008091015A1 (ja) | 2008-07-31 |
US8236978B2 (en) | 2012-08-07 |
JP2008179588A (ja) | 2008-08-07 |
US20100029966A1 (en) | 2010-02-04 |
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