JP2008038011A5 - - Google Patents
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- JP2008038011A5 JP2008038011A5 JP2006213727A JP2006213727A JP2008038011A5 JP 2008038011 A5 JP2008038011 A5 JP 2008038011A5 JP 2006213727 A JP2006213727 A JP 2006213727A JP 2006213727 A JP2006213727 A JP 2006213727A JP 2008038011 A5 JP2008038011 A5 JP 2008038011A5
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- JP
- Japan
- Prior art keywords
- phospholipid
- silica gel
- gel column
- egg yolk
- acetone
- Prior art date
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- 150000003904 phospholipids Chemical class 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229940067631 Phospholipids Drugs 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 210000002969 Egg Yolk Anatomy 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 235000013345 egg yolk Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N Isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000008344 egg yolk phospholipid Substances 0.000 description 2
- 230000004634 feeding behavior Effects 0.000 description 2
- 239000008079 hexane Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005445 natural product Substances 0.000 description 2
- 229930014626 natural products Natural products 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- PFTAWBLQPZVEMU-DZGCQCFKSA-N Catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- 229940100626 Catechin Drugs 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 229950001002 Cianidanol Drugs 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007842 Glycine max Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 210000001672 Ovary Anatomy 0.000 description 1
- UNJJBGNPUUVVFQ-ZJUUUORDSA-N Phosphatidylserine Chemical compound CCCC(=O)O[C@H](COC(=O)CC)COP(O)(=O)OC[C@H](N)C(O)=O UNJJBGNPUUVVFQ-ZJUUUORDSA-N 0.000 description 1
- 229940068065 Phytosterols Drugs 0.000 description 1
- 241000508269 Psidium Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N Silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 210000001550 Testis Anatomy 0.000 description 1
- 229960001295 Tocopherol Drugs 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Vitamin C Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229940046009 Vitamin E Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229930016253 catechin Natural products 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000007882 dietary composition Nutrition 0.000 description 1
- 235000021271 drinking Nutrition 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000001804 emulsifying Effects 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011031 large scale production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000008103 phosphatidic acids Chemical class 0.000 description 1
- 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 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008345 purified egg yolk phospholipid Substances 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229930003799 tocopherols Natural products 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 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 1
Description
リン脂質は動物、植物等の生体内に広く分布しており、その植物性、動物性のいずれもが利用価値の高い物質である。例えば、リン脂質はその界面活性機能から食品分野、化粧品分野、医薬品分野に利用されている。特にリン脂質含量が高純度に精製されたリン脂質は乳化特性、安全性に優れていることから脂質輸液など医薬品分野での利用開発が行われている。
従来のリン脂質の精製法としては、アセトン分別法(特許文献1)とシリカゲルカラム法(特許文献2)が挙げられる。例えば、卵黄由来リン脂質としては、割卵分離して得られた卵黄液を一旦乾燥して乾燥卵黄としたものに、アルコールを作用させてアルコール可溶性成分を抽出した後、該アルコールを除去して得られたものが知られている。精製卵黄リン脂質を得る方法としては、こうして得られた卵黄リン脂質を原料として、リン脂質はアセトンに不溶であるが、中性脂質はアセトンに可溶であるとの性質を利用する方法がよく知られている(アセトン分別法)。しかし、アセトン分別法は大規模な製造には適していないことや、アセトンの残留を減らすことが容易でないだけでなく、さらにその縮合体で特有の臭いを有するメシチルオキサイドやイソホロンなどの有害物質が生成することが、欠点として挙げられる。
一方、シリカゲルカラム法は原料の卵黄リン脂質をシリカゲルカラムに負荷し、クロロホルム−メタノール混液のメタノール含量を除々に増加して中性脂質を溶出した後、リン脂質を溶出させる方法がよく知られている(シリカゲルカラム法)。しかし、シリカゲルカラム法はクロロホルムやメタノールを使用することから、食品分野へは利用できない。また、シリカゲルカラム法は2種類の溶媒を濃度調整するため操作が煩雑である。
Phospholipids are widely distributed in living organisms such as animals and plants, and both plant and animal are highly useful substances. For example, phospholipids are used in the food field, cosmetic field, and pharmaceutical field because of their surface active function. In particular, phospholipids purified to a high purity with a high phospholipid content are excellent in emulsifying properties and safety, and are being developed for use in the pharmaceutical field such as lipid infusion.
Conventional methods for purifying phospholipids include acetone fractionation (Patent Document 1) and silica gel column method (Patent Document 2). For example, as egg yolk-derived phospholipid, the yolk liquid obtained by splitting egg yolk is dried once to obtain a dried egg yolk, and then alcohol is allowed to act to extract the alcohol-soluble component, and then the alcohol is removed. What is obtained is known. As a method for obtaining purified egg yolk phospholipid, a method utilizing the property that phospholipid is insoluble in acetone, but neutral lipid is soluble in acetone, using the egg yolk phospholipid thus obtained as a raw material is often used. Known (acetone fractionation method). However, the acetone fractionation method is not suitable for large-scale production, and it is not easy to reduce the residue of acetone, but also its condensate has a unique odor and harmful substances such as mesityl oxide and isophorone There can be generated, and as a disadvantage.
On the other hand, the silica gel column method is well known in which the raw material egg yolk phospholipid is loaded onto a silica gel column, the methanol content in the chloroform-methanol mixture is gradually increased to elute the neutral lipid, and then the phospholipid is eluted. (Silica gel column method). However, since the silica gel column method uses chloroform or methanol, it cannot be used in the food field. In addition, the silica gel column method is complicated to adjust the concentration of two types of solvents.
本発明は、従来全く想像すらされていなかった精製(製造)方法を用いて、高純度かつ有害な有機溶媒の混入のないリン脂質を提供することを可能にする。
(定義)
本明細書において使用する場合、用語「リン脂質」とは、リンを含む脂質をいう。リン脂質としては、ホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルセリン、ホスファチジルイノシトール、ホスファチジン酸が挙げられるが、これに限定されない。本明細書において使用する場合、リン脂質供給源としては、天然物原料、化学合成品、などが挙げられる。リン脂質供給源としての天然物原料としては、例えば、卵黄、卵巣、精巣、大豆、魚卵、魚介類(例えば、イカの可食部)などが挙げられるが、これに限定されない。
本明細書において使用する場合、用語「油脂成分」とは、天然または非天然のリン脂質供給源より有機溶媒によって抽出される成分であって、かつ、リン脂質を含有する成分をいう。
本明細書において使用する場合、用語「極性の低い有機溶媒」とは、シリカゲルカラムに負荷する物質を調製するために油脂成分と混合される有機溶媒であって、例えば、ヘキサンが挙げられるが、これに限定されない。
本明細書において使用する場合、用語「シリカゲル」とは、SiO2・nH2Oの非晶質ケイ酸をいう。本発明において使用する場合、好ましくは、シリカゲルの粒子径は0.005mm〜10mmであり、球状でも破砕状でもよい。
本明細書において使用する場合、用語「抽出用有機溶媒」とは、本発明の方法によって高純度なリン脂質を製造するために極性の低い有機溶媒と混合されるための油脂成分を抽出によって調製する際に、その抽出に使用される有機溶媒をいう。抽出用有機溶媒としては、エタノール、ヘキサン、イソプロピルアルコール、酢酸エチル、アセトン、エーテル、クロロホルム、メタノール、あるいはこれらの混合物、が挙げられるが、これに限定されない。
また、本発明で製造される高純度リン脂質は、食品としての経口摂取が可能であることから、健康食品としての利用も可能である。
The present invention makes it possible to provide a high-purity phospholipid free from harmful organic solvents using a purification (manufacturing) method that has never been imagined.
(Definition)
As used herein, the term “phospholipid” refers to a lipid containing phosphorus. Phospholipids include, but are not limited to, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, and phosphatidic acid. As used herein, phospholipid sources include natural product raw materials, chemically synthesized products, and the like. Examples of the natural product raw material as a phospholipid supply source include, but are not limited to, egg yolk, ovary, testis, soybean, fish egg, and seafood (for example, edible portion of squid).
As used herein, the term “fat component” refers to a component that is extracted from a natural or non-natural phospholipid source by an organic solvent and contains a phospholipid.
As used herein, the term "lower organic polar solvents" is an organic solvent that is mixed with oil components in order to prepare the material loaded on a silica gel column, for example, there may be mentioned hexane However, the present invention is not limited to this.
As used herein, the term “silica gel” refers to an amorphous silicic acid of SiO 2 .nH 2 O. When used in the present invention, the silica gel preferably has a particle size of 0.005 mm to 10 mm and may be spherical or crushed.
As used herein, the term “organic solvent for extraction” refers to the extraction of oil components to be mixed with a less polar organic solvent to produce high purity phospholipids by the method of the present invention. In this case, it means an organic solvent used for the extraction. Examples of the organic solvent for extraction include, but are not limited to, ethanol, hexane, isopropyl alcohol, ethyl acetate, acetone, ether, chloroform, methanol, or a mixture thereof.
In addition, since the high-purity phospholipid produced in the present invention can be taken orally as a food, it can also be used as a health food.
本発明の薬学的組成物および飲食用組成物は、高度に精製されたリン脂質を有効成分として含有する。本発明の薬学的組成物および飲食用組成物は、活性成分としてリン脂質のみを単独で配合した形態、あるいはリン脂質以外の活性成分と組み合わせた形態において構成され、望ましくはリン脂質の含有量が20重量%以上、さらに好ましくは30重量%以上である。本発明の所望の効果を阻害しない範囲および程度であれば、他の公知の成分あるいは原材料を適宜に併用せしめてもよい。これらの例としてアスコルビン酸、アミノ酸、ペプチド、蛋白質およびこの分解物、各種糖質、澱粉およびこの分解物、ミネラル類、ビタミンE、トコフェロール、フィトステロール、カテキン、グァバ葉等のポリフェノール類等およびこれらの誘導体を挙げることができるが、これらに限定されない。
The pharmaceutical composition and the composition for eating and drinking of the present invention contain highly purified phospholipid as an active ingredient. Pharmaceutical compositions and dietary compositions of the present invention, a form of phospholipid only blended alone as the active ingredient, or is Oite constructed in the form state combined with an active ingredient other than a phospholipid, preferably a phospholipid The content is 20% by weight or more, more preferably 30% by weight or more. Other known components or raw materials may be used in combination as appropriate as long as they do not interfere with the desired effects of the present invention. Examples thereof include ascorbic acid, amino acids, peptides, proteins and degradation products thereof, various sugars, starches and degradation products thereof, minerals, vitamin E, tocopherol, phytosterols, polyphenols such as catechin and guava leaves, and derivatives thereof. Although not limited to these, it is not limited to these.
Priority Applications (1)
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JP2006213727A JP2008038011A (en) | 2006-08-04 | 2006-08-04 | Method for producing highly pure phospholipid |
Applications Claiming Priority (1)
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JP2006213727A JP2008038011A (en) | 2006-08-04 | 2006-08-04 | Method for producing highly pure phospholipid |
Publications (2)
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JP2008038011A JP2008038011A (en) | 2008-02-21 |
JP2008038011A5 true JP2008038011A5 (en) | 2009-08-27 |
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JP2006213727A Pending JP2008038011A (en) | 2006-08-04 | 2006-08-04 | Method for producing highly pure phospholipid |
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JP7357471B2 (en) * | 2019-06-13 | 2023-10-06 | キユーピー株式会社 | Phospholipid purification method |
TWI815067B (en) | 2019-12-26 | 2023-09-11 | 日商瑪魯哈日魯股份有限公司 | Fish egg lipid composition containing phospholipids combined with polyunsaturated fatty acids |
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JP2909508B2 (en) * | 1989-02-14 | 1999-06-23 | マルハ株式会社 | Krill phospholipid fractionation method |
JP2646421B2 (en) * | 1993-10-12 | 1997-08-27 | 日清製油株式会社 | Obesity prevention agent |
JP3009017B2 (en) * | 1993-10-19 | 2000-02-14 | 日清製油株式会社 | Blood lipid lowering agent |
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