JP3531876B2 - Method for obtaining phospholipid composition containing docosahexaenoic acid - Google Patents
Method for obtaining phospholipid composition containing docosahexaenoic acidInfo
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- JP3531876B2 JP3531876B2 JP13409293A JP13409293A JP3531876B2 JP 3531876 B2 JP3531876 B2 JP 3531876B2 JP 13409293 A JP13409293 A JP 13409293A JP 13409293 A JP13409293 A JP 13409293A JP 3531876 B2 JP3531876 B2 JP 3531876B2
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- phospholipid
- dha
- chloroform
- phospholipid composition
- composition containing
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Description
【0001】[0001]
【産業上の利用分野】本発明は頭足類の皮からドコサヘ
キサエン酸(以下DHAという)を含むリン脂質組成物
を取得する方法に関するものである。該リン脂質は食
品、医薬品、化粧品、水産、化成品、農業などの分野に
おいて有用である。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for obtaining a phospholipid composition containing docosahexaenoic acid (hereinafter referred to as DHA) from cephalopod skin. The phospholipid is useful in fields such as foods, pharmaceuticals, cosmetics, marine products, chemical products, and agriculture.
【0002】[0002]
【従来の技術】DHAはω−3系列の高度不飽和脂肪酸
(以下PUFAという)として、他のω−3系列のPU
FAであるエイコサペンタエン酸(以下EPAという)
やα−リノレン酸(以下ALAという)と同様に、ω−
6系列のPUFAと拮抗する生理作用を有すると共に、
EPAやALAには見られない学習能向上作用、明度識
別能向上作用、抗アレルギー作用などが知られている。
このため、老人性痴呆症や、成人病が深刻になりつつあ
る現代社会において、医薬品や健康食品或いは化粧品へ
の応用が期待されている。2. Description of the Related Art DHA is a ω-3 series polyunsaturated fatty acid (hereinafter referred to as PUFA) and is used as another ω-3 series PU.
Eicosapentaenoic acid, which is FA (hereinafter referred to as EPA)
And α-linolenic acid (hereinafter referred to as ALA), ω-
In addition to having a physiological action that antagonizes 6 series of PUFAs,
It is known to have a learning ability improving action, a brightness discriminating ability improving action, an antiallergic action, and the like, which are not found in EPA and ALA.
Therefore, it is expected to be applied to medicines, health foods, and cosmetics in the modern society where senile dementia and adult diseases are becoming serious.
【0003】これらの用途に対するDHAの化学形とし
ては細胞毒性などの副作用がないことから、生体成分で
あるトリグリセリドやリン脂質が好ましいとされてい
る。中でもリン脂質は神経伝達物質であるアセチルコリ
ンの原料になり得るホスファチジルコリン(以下PCと
いう)、細胞膜を形成するホスファチジルエタノールア
ミン(以下PEという)、プロテインキナーゼC活性化に
関与するホスファチジルセリンなどのように、それ自体
が有用な生理作用を有することが知られている。As the chemical form of DHA for these uses, triglycerides and phospholipids, which are biological components, are said to be preferable because they have no side effects such as cytotoxicity. Among them, phospholipids are phosphatidylcholine (hereinafter referred to as PC) that can be a raw material of acetylcholine which is a neurotransmitter, phosphatidylethanolamine (hereinafter referred to as PE) that forms a cell membrane, phosphatidylserine involved in protein kinase C activation, etc. It is known that itself has a useful physiological action.
【0004】これまで、DHAを含有するリン脂質は、
海産魚類および藻類脂質、海産魚類卵、卵黄などの天然
物から抽出するか、あるいはホスフォリパーゼA2やリパ
ーゼを用いる酵素による合成法もしくは化学合成法によ
り得られている。しかしながら、上記の天然物から抽出
する方法では、天然物中のDHA含有量が低いと共に、
リン脂質としての存在量が低いため、生産コストが高く
なるという欠点がある。酵素合成法や化学合成法では、
DHA含有量の高いリン脂質を合成することができる
が、工業的な大量生産は困難であり、また生産コストは
天然物からの抽出より高くなる。このように、DHA含
有量の高いリン脂質を、安価かつ安定に大量供給しうる
入手方法は知られていなかった。So far, phospholipids containing DHA have been
It is obtained from natural products such as marine fish and algal lipids, marine fish eggs and egg yolk, or by enzymatic or chemical synthesis using phospholipase A2 or lipase. However, in the above method of extracting from natural products, the DHA content in the natural products is low, and
Since the amount of phospholipids present is low, there is a drawback that the production cost is high. In enzymatic and chemical synthesis methods,
Phospholipids with a high DHA content can be synthesized, but industrial mass production is difficult, and the production cost is higher than extraction from natural products. As described above, there has been no known method for obtaining a large amount of phospholipid having a high DHA content inexpensively and stably.
【0005】[0005]
【本発明が解決しようとする課題】本発明の目的は、D
HA含有量の高いリン脂質を安価に安定して大量供給で
きる方法を提供することにある。DISCLOSURE OF THE INVENTION The object of the present invention is to
It is intended to provide a method capable of stably and inexpensively supplying a large amount of phospholipid having a high HA content.
【0006】[0006]
【課題を解決するための手段】本発明者らは、上記の課
題を解決するために鋭意研究した結果、頭足類の皮に含
まれているリン脂質にDHAが高含有量で存在すること
を見いだし、本発明を完成するに至った。Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that phospholipids contained in the skin of cephalopods have a high content of DHA. The present invention has been completed and the present invention has been completed.
【0007】すなわち本発明は、頭足類の皮から脂質成
分を抽出し、次いで脂質成分を分画することを特徴とす
る、ドコサヘキサエン酸を含むリン脂質組成物の取得方
法に関する。That is, the present invention relates to a method for obtaining a phospholipid composition containing docosahexaenoic acid, which comprises extracting a lipid component from cephalopod skin and then fractionating the lipid component.
【0008】本発明で利用できる頭足類としてはイカ及
びタコを挙げることができる。このうち、イカは、(1)
その皮にリン脂質が湿重量当り約2%含まれること、(2)
このリン脂質の約50%がPC、20%がPEであること、
(3)DHAはPCの構成脂肪酸のうち約50%、PEの構成
脂肪酸のうち約20%を占めること、(4)DHAはPCとP
Eのsn-2位に局在していること、(5)その皮から溶剤分
別した後、既存の吸着クロマトグラフィーとイオン交換
クロマトグラフィーを組み合わせることによって、PC
とPEを他のリン脂質から別個に容易に単離できるこ
と、(6)イカの皮は、可食部を取った後、廃棄物として
大量に存在し、かつ実質的に無償で入手できること、等
の点で好ましい。イカとしては、ムラサキイカ、ヤリイ
カ、コウイカ、ホタルイカ等が挙げられる。Cephalopods that can be used in the present invention include squid and octopus. Of these, squid is (1)
The skin contains about 2% of phospholipids per wet weight, (2)
About 50% of this phospholipid is PC and 20% is PE,
(3) DHA accounts for about 50% of PC constituent fatty acids and about 20% of PE constituent fatty acids. (4) DHA accounts for PC and P
It is localized at the sn-2 position of E. (5) After the solvent fractionation from the skin, by combining the existing adsorption chromatography and ion exchange chromatography, PC
And PE can be easily isolated separately from other phospholipids, (6) Squid skin is present as a large amount of waste after removing the edible portion, and can be obtained substantially free of charge, etc. In terms of Examples of squid include purple squid, squid, cuttlefish, and firefly squid.
【0009】本発明の実施に当たっては、脂質成分の抽
出の前に、頭足類の皮を凍結乾燥した後、細かく砕いて
表面積を広げることが好ましい。脂質成分の抽出は、通
常、有機溶剤を用いることにより好適に達成される。用
いられる有機溶剤としては、リン脂質を溶解する通常の
溶剤を単独又は混合して用いることができ、例えばクロ
ロホルム、エーテル、ブチルアルコール、クロロホルム
-メタノール系、n-ヘキサン-エタノール水系、クロロホ
ルム-n-ヘキサン系、クロロホルム-エーテル系、クロロ
ホルム-エタノール系などが挙げられる。これらの溶媒
のうち、クロロホルム-メタノール系が好ましく、特
に、クロロホルムの比率が50%以上、より好ましくは
65%以上であることが脂質成分の抽出効率が良い点で
望ましい。In the practice of the present invention, it is preferable to freeze-dry the cephalopod skin before extracting the lipid component and then crush it finely to increase the surface area. Extraction of the lipid component is usually suitably achieved by using an organic solvent. As the organic solvent used, a conventional solvent that dissolves phospholipids can be used alone or in combination, and examples thereof include chloroform, ether, butyl alcohol, and chloroform.
-Methanol system, n-hexane-ethanol aqueous system, chloroform-n-hexane system, chloroform-ether system, chloroform-ethanol system and the like. Of these solvents, a chloroform-methanol system is preferable, and a ratio of chloroform is preferably 50% or more, more preferably 65% or more, in terms of good extraction efficiency of lipid components.
【0010】次いで、得られた脂質成分を分画すること
により、DHAを含むリン脂質を取得できる。分画は、
一般に有機溶剤を除去した後、脂質成分からリン脂質を
分画するのに通常用いられる方法のいずれかにより行な
うことができるが、大量に処理できる点で、分別用溶剤
を加えて不溶性物質を分離する方法、すなわち溶剤分別
法により行なうことが好ましい。分別用溶剤としては、
通常、脂質の分別に用いられる有機溶剤を用いることが
でき、例えば、アセトン、酢酸、クロロホルム、エーテ
ルなどが挙げられる。これらの溶剤のうち、分画効率が
よい点で、特に、アセトンが好ましい。また、溶剤に塩
化マグネシウム、塩化カルシウムなどを添加し、その共
存下、分別を行ってもよく、必要に応じて加熱、冷却な
どを行ってもよい。更に、得られた画分をカラムクロマ
トグラフィーで再分画し、目的とするリン脂質の画分を
集めることにより、高純度のリン脂質組成物を高収率で
得ることができる。カラムクロマトグラフィーとして
は、シリカ系クロマトグラフィー、疎水性クロマトグラ
フィー、イオン交換クロマトグラフィーなどを用いるこ
とができる。PCとPEを各々分画する必要がある場合
には、溶剤分別により得られたリン脂質組成物をまずシ
リカ系クロマトグラフィーに処してPEを分離し、次い
でイオン交換クロマトグラフィーに処することによりP
Cを分離することができる。Then, the obtained lipid component is fractionated to obtain a phospholipid containing DHA. The fraction is
Generally, after removing the organic solvent, it can be carried out by any of the methods usually used for fractionating phospholipids from lipid components. However, since a large amount can be processed, a fractionating solvent is added to separate insoluble substances. It is preferable to carry out the above method, that is, the solvent fractionation method. As a solvent for separation,
Usually, an organic solvent used for fractionating lipids can be used, and examples thereof include acetone, acetic acid, chloroform and ether. Of these solvents, acetone is particularly preferable because of its high fractionation efficiency. Further, magnesium chloride, calcium chloride or the like may be added to the solvent and the fractionation may be performed in the coexistence thereof, and heating, cooling or the like may be performed as necessary. Further, the obtained fraction is re-fractionated by column chromatography and the desired phospholipid fraction is collected, whereby a highly pure phospholipid composition can be obtained in a high yield. As column chromatography, silica-based chromatography, hydrophobic chromatography, ion exchange chromatography and the like can be used. When it is necessary to fractionate each of PC and PE, the phospholipid composition obtained by solvent fractionation is first subjected to silica-based chromatography to separate PE, and then subjected to ion exchange chromatography to obtain P.
C can be separated.
【0011】このようにして得られるリン脂質は、薄層
クロマトグラフィーとNMRで分析してその種類を同定
することができ、更に常法によって、ケン化分解、メチ
ルエステル化、又は、メタノリシスによって、脂肪酸メ
チルエステルとした後、ガスクロマトグラフィーで分析
して構成脂肪酸組成を求めることができる。更に、これ
らのリン脂質をホスフォリパーゼA2で処理し、生成した
遊離脂肪酸とリゾリン脂質を薄層クロマトグラフィーで
分画した後、上述のように脂肪酸分析を行うことによっ
て、脂肪酸のリン脂質分子内分布を決定することができ
る。The thus-obtained phospholipid can be analyzed by thin layer chromatography and NMR to identify its type, and can be further subjected to saponification, methyl esterification, or methanolysis by a conventional method. After forming the fatty acid methyl ester, it can be analyzed by gas chromatography to determine the constituent fatty acid composition. Furthermore, these phospholipids were treated with phospholipase A2, and the produced free fatty acids and lysophospholipids were fractionated by thin-layer chromatography, and then fatty acid analysis was performed as described above, thereby The distribution can be determined.
【0012】上述の方法により得られるリン脂質組成物
は、通常、PC及び/又はPEを主成分として含有し、
又その構成脂肪酸はDHA、EPA、ステアリン酸、パ
ルミチン酸などであった。The phospholipid composition obtained by the above method usually contains PC and / or PE as a main component,
The constituent fatty acids were DHA, EPA, stearic acid, palmitic acid and the like.
【0013】[0013]
【実施例】以下、実施例により本発明を更に詳細に説明
する。ただし、本発明はこれらの実施例に限定されるも
のではない。EXAMPLES The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples.
【0014】実施例 1
湿重量10gのムラサキイカの皮を凍結乾燥し、1.6gの乾
物を得た。これを細かく砕いた後、クロロホルム:メタ
ノール=2:1の混合溶剤で抽出し、0.26gの脂質成分を得
た。この脂質成分にアセトン40mlを加え、冷却しながら
撹拌を行い、中性脂質を分別濾過し、アセトン不溶分0.
22gを得た。これをシリカゲルカラムクロマトグラフィ
ーにかけ、クロロホルム:メタノール=85:15、80:20、
75:25の順で各々500ml、400ml、2000ml展開した。これ
によって、PE及びその他のリン脂質混合物に分画でき
た。次に、その他のリン脂質混合物をセファロースカラ
ムクロマトグラフィーにかけ、クロロホルム:メタノー
ル=1:4、酢酸、クロロホルム:メタノール=1:4+酢酸
アンモニウム(0.2%)を100mlづつで順次展開した。これ
によって、その他のリン脂質混合物からPCを単離でき
た。単離されたPCとPEは各々0.11gと0.04gであっ
た。これらのリン脂質はNMRで各々の構造を確認した
後、脂肪酸組成を分析したところ、DHA、EPA、ス
テアリン酸、パルミチン酸はPCでは各々51%、5%、2
%、33%、PEでは19%、33%、12%、6%であった。又、こ
れらの脂肪酸の分子内分布を分析したところ、PCのsn
-2位はすべてDHAであった。PEのsn-2位はDHA又
はEPAであった。Example 1 The skin of purple squid having a wet weight of 10 g was freeze-dried to obtain 1.6 g of a dry matter. After crushing this finely, it was extracted with a mixed solvent of chloroform: methanol = 2: 1 to obtain 0.26 g of a lipid component. To this lipid component, 40 ml of acetone was added, and the mixture was stirred while cooling, neutral lipids were separated and filtered, and the acetone-insoluble matter was reduced to 0.
I got 22g. This is subjected to silica gel column chromatography, and chloroform: methanol = 85: 15, 80:20,
In the order of 75:25, 500 ml, 400 ml, and 2000 ml were developed, respectively. This allowed fractionation into PE and other phospholipid mixtures. Next, the other phospholipid mixture was subjected to Sepharose column chromatography, and chloroform: methanol = 1: 4, acetic acid, chloroform: methanol = 1: 4 + ammonium acetate (0.2%) were sequentially developed in 100 ml portions. This allowed PC to be isolated from other phospholipid mixtures. The isolated PC and PE were 0.11 g and 0.04 g, respectively. After confirming their respective structures by NMR, the fatty acid composition of these phospholipids was analyzed.
%, 33%, PE: 19%, 33%, 12%, 6%. In addition, when the intramolecular distribution of these fatty acids was analyzed, it was found that PC sn
-2nd place was all DHA. The sn-2 position of PE was DHA or EPA.
【0015】実施例 2
湿重量30gのムラサキイカの皮を凍結乾燥し、4.8gの乾
物を得た。これを細かく砕いた後、クロロホルム:メタ
ノール=2:1の混合溶剤で抽出し、0.61gの脂質成分を得
た。この脂質成分にアセトン40mlを加え、冷却しながら
撹拌を行い、中性脂質を分別濾過し、アセトン不溶分0.
54gを得た。これをシリカゲルカラムクロマトグラフィ
ーにかけ、クロロホルム:メタノール=85:15、80:20、
75:25の順で各々500ml、400ml、2000ml展開した。これ
によって、PE及びその他のリン脂質混合物に分画でき
た。次に、その他のリン脂質混合物をセファロースカラ
ムクロマトグラフィーにかけ、クロロホルム:メタノー
ル=1:4、酢酸、クロロホルム:メタノール=1:4+酢酸
アンモニウム(0.2%)を100mlづつで順次展開した。これ
によって、その他のリン脂質混合物からPCを単離でき
た。単離されたPCとPEは各々0.29gと0.15gであっ
た。これらのリン脂質はNMRで各々の構造を確認した
後、脂肪酸組成を分析したところ、DHA、EPA、ス
テアリン酸、パルミチン酸はPCでは各々49%、6%、2
%、33%、PEでは18%、33%、11%、6%であった。又、こ
れらの脂肪酸の分子内分布を分析したところ、PCのsn
-2位はすべてDHAであった。PEのsn-2位はDHA又
はEPAであった。Example 2 The skin of purple squid having a wet weight of 30 g was freeze-dried to obtain 4.8 g of a dry matter. After crushing this finely, it was extracted with a mixed solvent of chloroform: methanol = 2: 1 to obtain 0.61 g of a lipid component. To this lipid component, 40 ml of acetone was added, and the mixture was stirred while cooling, neutral lipids were separated and filtered, and the acetone-insoluble matter was reduced to 0.
Got 54g. This is subjected to silica gel column chromatography, and chloroform: methanol = 85: 15, 80:20,
In the order of 75:25, 500 ml, 400 ml, and 2000 ml were developed, respectively. This allowed fractionation into PE and other phospholipid mixtures. Next, the other phospholipid mixture was subjected to Sepharose column chromatography, and chloroform: methanol = 1: 4, acetic acid, chloroform: methanol = 1: 4 + ammonium acetate (0.2%) were sequentially developed in 100 ml portions. This allowed PC to be isolated from other phospholipid mixtures. The isolated PC and PE were 0.29 g and 0.15 g, respectively. These phospholipids were analyzed for their fatty acid composition after confirming their structures by NMR. DHA, EPA, stearic acid and palmitic acid were found to be 49%, 6% and 2% respectively in PC.
%, 33%, 18%, 33%, 11% and 6% for PE. In addition, when the intramolecular distribution of these fatty acids was analyzed, it was found that PC sn
-2nd place was all DHA. The sn-2 position of PE was DHA or EPA.
【0016】[0016]
【発明の効果】本発明により、DHAを含むリン脂質を
大量に効率よく、しかも安価に取得することが可能とな
った。特に、脂質成分の分画を溶剤分別とカラムクロマ
トグラフィー等とを組み合わせる方法により、DHAを
含むPC及びPEを効率良く短時間で且つ容易に単離、
精製しうる。この結果、多くの有用な生理作用が期待さ
れるDHAを含むリン脂質を、研究用試薬、医薬、健康
食品、化粧品の原料などとして大量に且つ安価に供給す
ることが可能となった。INDUSTRIAL APPLICABILITY According to the present invention, a large amount of phospholipid containing DHA can be efficiently obtained at low cost. In particular, the method of combining fractionation of lipid components with solvent fractionation and column chromatography etc. efficiently and easily isolates PC and PE containing DHA in a short time,
It can be purified. As a result, it has become possible to supply a large amount of phospholipid containing DHA, which is expected to have many useful physiological effects, as a raw material for research reagents, medicines, health foods, cosmetics, etc. at low cost.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7,DB名) C07F 9/10 A23J 7/00 C11B 7/00,11/00 ─────────────────────────────────────────────────── ─── Continuation of front page (58) Fields surveyed (Int.Cl. 7 , DB name) C07F 9/10 A23J 7/00 C11B 7 / 00,11 / 00
Claims (4)
で得られた脂質成分を分画することを特徴とする、ドコ
サヘキサエン酸を含むリン脂質組成物の取得方法。1. A method for obtaining a phospholipid composition containing docosahexaenoic acid, which comprises extracting a lipid component from the skin of a cephalopod and then fractionating the obtained lipid component.
方法。2. The acquisition method according to claim 1, wherein the cephalopod is squid.
る請求項1又は2記載の取得方法。3. The acquisition method according to claim 1, wherein fractionation is performed by solvent fractionation.
ホスファチジルコリン及び/又はホスファチジルエタノ
ールアミンを主成分とするものである請求項1〜3のい
ずれかに記載の取得方法。4. The phospholipid constituting the phospholipid composition,
The method according to any one of claims 1 to 3, which comprises phosphatidylcholine and / or phosphatidylethanolamine as a main component.
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JP13409293A JP3531876B2 (en) | 1993-05-13 | 1993-05-13 | Method for obtaining phospholipid composition containing docosahexaenoic acid |
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JP13409293A JP3531876B2 (en) | 1993-05-13 | 1993-05-13 | Method for obtaining phospholipid composition containing docosahexaenoic acid |
Publications (2)
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JPH06321970A JPH06321970A (en) | 1994-11-22 |
JP3531876B2 true JP3531876B2 (en) | 2004-05-31 |
Family
ID=15120247
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US6054494A (en) * | 1996-11-13 | 2000-04-25 | Q. P. Corporation | Phospholipid composition |
JP3408958B2 (en) | 1997-10-24 | 2003-05-19 | 旭化成株式会社 | Composition containing useful substance derived from fish and shellfish and method for producing the useful substance |
GB0813598D0 (en) * | 2008-07-24 | 2008-09-03 | Pharma Marine As | Process |
JP5613872B2 (en) * | 2011-08-11 | 2014-10-29 | 洋昭 齋藤 | Method for producing lipids containing useful fatty acid residues such as docosapentaenoic acid and arachidonic acid |
WO2021132516A1 (en) | 2019-12-26 | 2021-07-01 | マルハニチロ株式会社 | Roe lipid composition containing polyvalent unsaturated fatty acid-bound phospholipid |
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