JPH1135587A - Production of lipid consisting essentially of arachidonic acid-containing lipid - Google Patents
Production of lipid consisting essentially of arachidonic acid-containing lipidInfo
- Publication number
- JPH1135587A JPH1135587A JP22419497A JP22419497A JPH1135587A JP H1135587 A JPH1135587 A JP H1135587A JP 22419497 A JP22419497 A JP 22419497A JP 22419497 A JP22419497 A JP 22419497A JP H1135587 A JPH1135587 A JP H1135587A
- Authority
- JP
- Japan
- Prior art keywords
- arachidonic acid
- lipid
- phospholipid
- solvent
- content
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Extraction Or Liquid Replacement (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新鮮な家畜の内臓
より、アラキドン酸を多量に含むリン脂質を含有する脂
質を製造する方法、そのようにして製造されたアラキド
ン酸高含有リン脂質を主成分とする脂質、及び該脂質を
配合してなる食品組成物に関する。TECHNICAL FIELD The present invention relates to a method for producing a lipid containing arachidonic acid-rich phospholipid from the gut of a fresh domestic animal, and a method for producing a lipid containing arachidonic acid-rich phospholipid produced in such a manner. The present invention relates to a lipid as a component and a food composition containing the lipid.
【０００２】[0002]
【従来の技術】アラキドン酸（ａｒａｃｈｉｄｏｎｉｃ
ａｃｉｄ，全シス５，８，１１，１４−エイコサテト
ラエン酸）は、プロスタグランジン、ロイコトリエンな
どの種々の生理活性物質を生合成する一連の酵素反応で
あるアラキドン酸カスケードの最初に位置する高度不飽
和脂肪酸であり、必須脂肪酸の１つとされている。アラ
キドン酸は母乳にも含まれており、胎児期から乳児期に
至る成長の過程に関与していると考えられることから、
育児用の粉ミルクにアラキドン酸を配合することが望ま
れる。そのような目的には、不要な物質の混入を回避す
るために、できるだけ高純度のアラキドン酸を含有する
安全な製品を配合する必要がある。従来、アラキドン酸
含有脂質製品は、魚油や卵黄油から抽出するか、モルテ
ィエレラ属等の菌にアラキドン酸を多量に含有するトリ
グリセリドを生成させ、菌体から精製する方法で得られ
ていた。BACKGROUND OF THE INVENTION Arachidonic acid
acid, all cis 5,8,11,14-eicosatetraenoic acid) is at the beginning of the arachidonic acid cascade, a series of enzymatic reactions that biosynthesize various bioactive substances such as prostaglandins, leukotrienes and the like. It is a highly unsaturated fatty acid and one of the essential fatty acids. Arachidonic acid is also found in breast milk and is thought to be involved in the growth process from fetal to infancy,
It is desired to mix arachidonic acid with infant formula. For such purposes, it is necessary to formulate a safe product containing arachidonic acid with as high a purity as possible in order to avoid contamination with unnecessary substances. Conventionally, arachidonic acid-containing lipid products have been obtained by extracting from fish oil or egg yolk oil, or by producing a triglyceride containing a large amount of arachidonic acid in a bacterium such as Mortierella and purifying it from the cells.
【０００３】[0003]
【発明が解決しようとする課題】しかし、魚油や卵黄油
における構成脂肪酸中のアラキドン酸含有量は１〜５重
量％にすぎず、効率良く、高濃度（高純度）のアラキド
ン酸を得ることができなかった。一方、微生物を用いる
方法の場合、微生物由来のタンパク質による汚染の恐れ
があり、製品の安全性の点で万全とは言い難いものであ
った。However, the content of arachidonic acid in the constituent fatty acids in fish oil and egg yolk oil is only 1 to 5% by weight, and it is necessary to obtain arachidonic acid of high concentration (high purity) efficiently. could not. On the other hand, in the case of a method using a microorganism, there is a risk of contamination by a protein derived from the microorganism, and it has been difficult to say that the method is perfect in terms of product safety.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、高濃度
（高純度）のアラキドン酸を含有し、しかも安全性の高
い製品を供給することを目的として、鋭意研究を重ねた
結果、食品として広く利用されている家畜の内臓を適当
に処理し、特定の方法で抽出することにより、該目的に
適うアラキドン酸含有抽出物を得ることができることを
見出し、本発明を完成するに至った。即ち、本発明は、
家畜の内臓を乾燥した後、有機溶剤で抽出し、次いで、
該溶剤を留去することを特徴とするアラキドン酸含有リ
ン脂質の製造法、及びそのようにして得られたアラキド
ン酸含有リン脂質を主成分とする脂質、さらには該脂質
を配合してなる食品組成物提供するものである。なお、
本発明において、アラキドン酸含有リン脂質、リン脂質
中アラキドン酸含有量などと記載するとき、「アラキド
ン含有」とは、リン脂質の構成脂肪酸としてアラキドン
酸を含む前記リン脂質を意味するものである。また、本
発明でいうリン脂質とは、分子種としてホスファチジル
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
ジン酸及びこれらのリゾ体であるアシル型グリセロリン
脂質の少なくとも１種以上を主成分として含み、さらに
スフィンゴミエリン、カルジオリピン等の成分を含む混
合リン脂質を指す。Means for Solving the Problems The inventors of the present invention have conducted intensive studies for the purpose of supplying a highly safe (high-purity) arachidonic acid-containing product with high safety. The present inventors have found that an arachidonic acid-containing extract suitable for the purpose can be obtained by appropriately treating the internal organs of livestock widely used as an extract and extracting it by a specific method, thereby completing the present invention. That is, the present invention
After drying the internal organs of the livestock, extract it with an organic solvent,
A method for producing an arachidonic acid-containing phospholipid, comprising distilling off the solvent, a lipid containing the arachidonic acid-containing phospholipid as a main component, and a food comprising the lipid. A composition is provided. In addition,
In the present invention, when describing arachidonic acid-containing phospholipids, arachidonic acid content in phospholipids, and the like, “arachidone-containing” means the phospholipids containing arachidonic acid as a constituent fatty acid of the phospholipid. Further, the phospholipid referred to in the present invention includes, as a main component, at least one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, phosphatidic acid and acyl glycerophospholipids that are lyso forms thereof as molecular species. Further, it refers to a mixed phospholipid containing components such as sphingomyelin and cardiolipin.
【０００５】[0005]
【発明の実施の形態】本発明の方法には、食肉の原料で
ある、豚、牛、馬、羊など、任意の家畜の内臓を用いる
ことができるが、豚又は牛が好ましい。また、アラキド
ン酸を含有することを条件として任意の内臓組織を用い
ることができるが、脂質含有率、総脂質中のアラキドン
酸含有量、総脂質中のリン脂質含量、リン脂質中のアラ
キドン酸含有量などの点、とりわけリン脂質中のアラキ
ドン酸含有量が比較的高い点を考慮して肝臓、脾臓、小
腸、大腸等が好ましい。より好ましいのは、肝臓、脾臓
及び小腸であり、最も好ましいのは肝臓である。ただ
し、これらに限定されず、本発明の目的に適う限り、任
意の動物の任意の臓器を使用できる。BEST MODE FOR CARRYING OUT THE INVENTION In the method of the present invention, any viscera of livestock such as pigs, cows, horses and sheep, which is a raw material of meat, can be used, but pigs or cows are preferred. In addition, any visceral tissue can be used provided that it contains arachidonic acid, but lipid content, arachidonic acid content in total lipids, phospholipid content in total lipids, arachidonic acid content in phospholipids The liver, spleen, small intestine, large intestine and the like are preferable in consideration of the amount and the like, particularly, the point that the arachidonic acid content in the phospholipid is relatively high. More preferred are the liver, spleen and small intestine, most preferred is the liver. However, the present invention is not limited thereto, and any organ of any animal can be used as long as it meets the purpose of the present invention.
【０００６】まず、原料中のアラキドン酸含有リン脂質
の品質が維持される条件下、水分含量が４０重量％以
下、好ましくは１０重量％以下になるまで乾燥する。乾
燥処理は、原料中のアラキドン酸含有リン脂質が酸化等
によって分解、変質しない温度範囲（７０℃以下、好ま
しくは−２０〜７０℃、さらに好ましくは−５〜５０
℃）で行うことが望ましい。熱風乾燥法、真空乾燥法、
凍結乾燥法（フリーズドライ）、低温・低湿度乾燥法等
を利用することができるが、真空乾燥法及び凍結乾燥法
を、単独で又は組み合わせて用いることが好ましい。凍
結乾燥法は、常法通り行われる。また、真空乾燥法は、
７０℃以下、好ましくは０〜７０℃の範囲の温度で約５
００ｍｍＨｇ以下の条件において行われる。[0006] First, the arachidonic acid-containing phospholipid in the raw material is dried until the water content becomes 40% by weight or less, preferably 10% by weight or less under the condition of maintaining the quality. The drying treatment is performed in a temperature range in which the arachidonic acid-containing phospholipid in the raw material is not decomposed or deteriorated by oxidation or the like (70 ° C. or lower, preferably −20 to 70 ° C., more preferably −5 to 50 ° C.).
C). Hot air drying, vacuum drying,
A freeze-drying method (freeze drying), a low-temperature / low-humidity drying method, or the like can be used, but it is preferable to use a vacuum drying method and a freeze-drying method alone or in combination. The freeze-drying method is performed as usual. In addition, the vacuum drying method,
70 ° C. or less, preferably in the range of 0-70 ° C. for about 5
It is performed under the condition of 00 mmHg or less.
【０００７】有機溶剤としては、メタノール、エタノー
ル、イソプロパノール及びオクタノール等のアルコール
系溶剤、ヘキサン、アセトン、或いはクロロホルム、メ
チルクロライド等の塩素系溶剤が挙げられ、これらを単
独または混合して用いることができるが、安全性等か
ら、エタノール若しくはヘキサン、又はこれらの混合溶
剤が適し、エタノール又はエタノールとヘキサンとの混
合溶剤が好ましい。エタノールとヘキサンとの混合比率
は任意であるが、エタノール／ヘキサン（容積比）＝
０．１〜１０が好ましく、さらには０．５〜２がより好
ましい。前記溶剤の使用量としては、最低限、抽出処理
すべき乾燥原料が浸漬できる量が必要であるが、通常、
重量比で乾燥原料の約２〜１０倍、好ましくは約３〜５
倍の溶媒を用いる。抽出温度は、アラキドン酸含有リン
脂質の品質が低下しない範囲であれば良く、通常、約１
０〜８０℃、好ましくは３０〜７０℃、より好ましくは
５０〜７０℃である。なお、抽出処理をエタノール単独
で行う場合、エタノールの還流温度以下に維持すること
が好ましい。該温度を越えると、リン脂質が変質、着色
しやすくなる。抽出時間は、原料の種類と状態、処理温
度、溶剤の種類及び使用量等により異なるが、一般に約
０．５〜５時間、好ましくは約１〜２時間程度である。
抽出操作は通常、１回でよいが、所望により数回繰り返
すこともできる。抽出効率を高めるためには、適宜、原
料を細断したり、撹拌しながら抽出してもよい。このよ
うにして得られた抽出液は、リン脂質を構成する脂肪酸
のうちアラキドン酸を高濃度に含有するリン脂質を主成
分とし、これとトリグリセリドとの混合物を含んでい
る。Examples of the organic solvent include alcohol solvents such as methanol, ethanol, isopropanol and octanol, and chlorinated solvents such as hexane, acetone and chloroform and methyl chloride. These can be used alone or in combination. However, from the viewpoint of safety and the like, ethanol or hexane or a mixed solvent thereof is suitable, and ethanol or a mixed solvent of ethanol and hexane is preferable. The mixing ratio of ethanol and hexane is arbitrary, but ethanol / hexane (volume ratio) =
0.1-10 are preferable, and 0.5-2 are more preferable. The amount of the solvent used is at least an amount that can immerse the dry raw material to be extracted,
About 2 to 10 times, preferably about 3 to 5 times by weight the dry raw material
Use twice the amount of solvent. The extraction temperature may be within a range where the quality of the arachidonic acid-containing phospholipid does not deteriorate, and is usually about 1
The temperature is 0 to 80 ° C, preferably 30 to 70 ° C, more preferably 50 to 70 ° C. When the extraction treatment is performed using ethanol alone, it is preferable to maintain the temperature at or below the reflux temperature of ethanol. If the temperature is exceeded, the phospholipids are liable to be altered and colored. The extraction time varies depending on the type and state of the raw materials, the processing temperature, the type of the solvent and the amount used, but is generally about 0.5 to 5 hours, preferably about 1 to 2 hours.
The extraction operation may usually be performed once, but may be repeated several times as desired. In order to increase the extraction efficiency, the raw material may be appropriately chopped or extracted with stirring. The extract thus obtained contains, as a main component, a phospholipid containing arachidonic acid at a high concentration among the fatty acids constituting the phospholipid, and contains a mixture of the phospholipid and triglyceride.
【０００８】次いで、前記抽出液から、約７０℃以下、
好ましくは３０〜７０℃、さらにより好ましくは４０〜
６０℃以下で溶剤を留去する。このように低温で処理す
ることによって、原料中のアラキドン酸含有リン脂質等
の抽出成分の酸化、劣化、分解、変質等を防止でき、本
発明の目的物を高品質の状態で製造できる。溶剤を留去
する手段としては、蒸留処理が好適である。蒸留は減
圧、好ましくは高真空（５〜３０ｍＨｇ）下で行う。こ
のようにして回収された溶剤は新たな抽出処理に再利用
できる。蒸留には市販の任意の蒸留機が用いられるが、
残留溶媒を完全に除去するためには流下膜式又は遠心式
の分子蒸留機が好ましい。分子蒸留の条件は特に限定さ
れないが、温度７０℃以下、真空度１０−５〜０．１ｍ
ｍＨｇ、好ましくは１０−３ｍｍＨｇにおいて、溶剤の
除去に必要な回数、循環させればよい。循環回数は任意
であるが、通常、３〜５回程度で十分である。また、分
子蒸留等による精製処理物を多量（２〜１０倍程度）の
アセトンと共存させ、不溶性成分であるリン脂質を分
離、採取することにより、抽出物中のアラキドン酸含有
リン脂質の含有量をさらに高めることができる。次い
で、凍結乾燥法等により、低温下、アセトンを除去して
最終製品とする。[0008] Next, from the above-mentioned extract, about 70 ° C or less
Preferably from 30 to 70 ° C, even more preferably from 40 to 70 ° C.
The solvent is distilled off at 60 ° C. or lower. By performing the treatment at such a low temperature, oxidation, deterioration, decomposition, alteration, and the like of the extracted components such as arachidonic acid-containing phospholipids in the raw materials can be prevented, and the object of the present invention can be produced in a high quality state. As a means for distilling off the solvent, a distillation treatment is preferable. Distillation is performed under reduced pressure, preferably under high vacuum (5-30 mHg). The solvent recovered in this way can be reused for a new extraction process. Any commercially available distillation machine is used for distillation,
In order to completely remove the residual solvent, a falling film type or centrifugal type molecular still is preferred. The conditions for molecular distillation are not particularly limited, but the temperature is 70 ° C. or less, and the degree of vacuum is 10 −5 to 0.1 m.
At mHg, preferably 10 −3 mmHg, circulation may be performed as many times as necessary to remove the solvent. The number of circulations is arbitrary, but usually about 3 to 5 times is sufficient. In addition, a purified product obtained by molecular distillation or the like is allowed to coexist with a large amount (about 2 to 10 times) of acetone, and phospholipids, which are insoluble components, are separated and collected, whereby the content of arachidonic acid-containing phospholipids in the extract is determined. Can be further enhanced. Next, acetone is removed at a low temperature by a freeze-drying method or the like to obtain a final product.
【０００９】本発明方法によれば、通常の食品原料から
高純度のアラキドン酸含有リン脂質を効率良く抽出、濃
縮することができる。本発明の方法で得られるリン脂質
抽出物は、構成脂肪酸組成として高濃度のアラキドン酸
を含有しており、抽出原料中の総脂質含有量、総脂質中
のリン脂質含有量、リン脂質中のアラキドン酸含有量は
原料によって変化するが、それぞれ約１０〜６０重量
％、約４５〜９０重量％、及び約１０〜５０重量％の範
囲の高濃度である。とりわけリン脂質中のアラキドン酸
含有量が１５重量％以上、具体的には１５〜３０重量％
のものがより好ましい。According to the method of the present invention, high-purity arachidonic acid-containing phospholipids can be efficiently extracted and concentrated from ordinary food materials. The phospholipid extract obtained by the method of the present invention contains a high concentration of arachidonic acid as a constituent fatty acid composition, the total lipid content in the extraction raw material, the phospholipid content in the total lipid, and the phospholipid content in the phospholipid. The arachidonic acid content varies with the feedstock, but is at a high concentration in the range of about 10-60% by weight, about 45-90% by weight, and about 10-50% by weight, respectively. In particular, the arachidonic acid content in the phospholipid is 15% by weight or more, specifically, 15 to 30% by weight.
Are more preferred.
【００１０】このように、本発明の方法で得られる抽出
物は、アラキドン酸を高濃度で含有し、かつ安全である
ことから、アラキドン酸が有用とされる食品や医薬品等
の任意の分野で、そのまま或いは適当な組成物に含有さ
せて用いることができる。食品の例として、粉ミルク、
ベビーフード、顆粒やソフトカプセル等の形態の健康食
品、バター、マーガリン、缶詰、佃煮等の通常の食品、
味噌、醤油、ソース、マヨネーズ、ドレッシング等の調
味料、チョコレート、ガム、キャンディ等の嗜好品、乳
酸菌飲料、茶、ジュース、ドリンク等の各種飲料が挙げ
られる。本発明の抽出物は、高いアラキドン酸含有率と
安全性の点から、とりわけ粉ミルクや離乳食等の乳幼児
の育児用食品に対する添加物として極めて有用である。[0010] As described above, the extract obtained by the method of the present invention contains arachidonic acid at a high concentration and is safe. Therefore, the extract is useful in any fields such as food and medicine where arachidonic acid is useful. Can be used as it is or in a suitable composition. Examples of foods include powdered milk,
Health foods in the form of baby food, granules and soft capsules, ordinary foods such as butter, margarine, canned food, boiled foods,
Examples include miso, soy sauce, sauces, mayonnaise, dressings and other seasonings, chocolates, gums, candy and other favorite items, lactic acid bacteria drinks, teas, juices, drinks and other various drinks. INDUSTRIAL APPLICABILITY The extract of the present invention is extremely useful as an additive to infant foods such as powdered milk and baby food, especially from the viewpoint of high arachidonic acid content and safety.
【００１１】以下に実施例を挙げ、本発明をさらに詳し
く説明するが、これらは本発明を制限するものではな
い。Hereinafter, the present invention will be described in more detail with reference to examples, but these examples do not limit the present invention.
【実施例】実施例１ 豚の各臓器を２日間、凍結乾燥した。生重量と乾燥後の
重量を表１に示す。 EXAMPLE 1 Each organ of a pig was freeze-dried for 2 days. The raw weight and the weight after drying are shown in Table 1.
【００１２】表１ ☆Table 1 ☆
【表１】 １）：生の内臓の水分含有率（重量％）[Table 1] 1): Water content of raw offal (% by weight)
【００１３】次に、表１に記載の乾燥物１０ｇに１０倍
量のヘキサン−エタノール（１：１）混合溶剤を加え、
ホモジナイズ後、６０℃で２時間静置下に抽出し、抽出
液をろ別した。このろ液を、ロータリーエバポレーター
を用いて、７０℃の温浴中にて３０ｍｍＨｇの減圧下で
濃縮し、エタノール２〜４重量％を含む濃縮物を得た。
次いで、該濃縮物を品温約６０℃、蒸発面温度約１００
℃、流下物温度６５〜７０℃の条件下で３回分子蒸留処
理し、ペースト状の抽出物（総脂質）を得た。また、前
記抽出物を約５倍量のアセトンに添加、撹拌した後、不
溶成分をろ別し、３０℃で真空乾燥してリン脂質を得
た。さらに、前記の総脂質及びリン脂質の各々につい
て、塩酸−メタノール法（１０％塩酸・メタノール溶
液、８０℃にて３時間加熱）により脂質の加水分解及び
脂肪酸のメチルエステル化反応を行わせた後、これをガ
スクロマトグラフィーに供して、各脂質の構成脂肪酸を
分析し、とくにアラキドン酸含有率を求めた。この結果
を表２に示す。なお、表２において、脂質含有率（重量
％）＝（総脂質の重量／臓器乾燥物の重量）ｘ１００、
総脂質中のリン脂質含有率（重量％）＝（リン脂質の重
量／総脂質の重量）ｘ１００、また総脂質中又はリン脂
質中のアラキドン酸含有率（重量％）は、各脂質の構成
脂肪酸中のアラキドン酸成分の含有割合である。Next, a 10-fold amount of a hexane-ethanol (1: 1) mixed solvent was added to 10 g of the dried product shown in Table 1,
After homogenization, the mixture was extracted at 60 ° C. for 2 hours while standing, and the extract was filtered. The filtrate was concentrated under reduced pressure of 30 mmHg in a hot bath at 70 ° C. using a rotary evaporator to obtain a concentrate containing 2 to 4% by weight of ethanol.
Next, the concentrate is heated at a product temperature of about 60 ° C and an evaporation surface temperature of about 100 ° C.
The mixture was subjected to a molecular distillation treatment three times at a temperature of 65 ° C. and a falling temperature of 65 ° C. to obtain a paste-like extract (total lipid). The extract was added to about 5 times the amount of acetone, and the mixture was stirred. Then, insoluble components were filtered off and dried at 30 ° C. in vacuo to obtain phospholipids. Further, for each of the above total lipids and phospholipids, hydrolysis of lipids and methyl esterification of fatty acids were performed by the hydrochloric acid-methanol method (10% hydrochloric acid / methanol solution, heating at 80 ° C. for 3 hours). This was subjected to gas chromatography to analyze the constituent fatty acids of each lipid, and particularly the arachidonic acid content was determined. Table 2 shows the results. In Table 2, lipid content (% by weight) = (weight of total lipid / weight of dried organ) × 100,
Phospholipid content in total lipids (% by weight) = (weight of phospholipids / weight of total lipids) × 100, and arachidonic acid content in total lipids or in phospholipids (% by weight) is determined by the constituent fatty acids of each lipid. It is a content ratio of an arachidonic acid component therein.
【００１４】表２ ☆Table 2 ☆
【表２】 注：ＴＬ：総脂質、ＰＬ：リン脂質、ＡＡ：アラキドン
酸 表中、（）内の数値は異常値と認め、平均値の算出の対
象から除外した。[Table 2] Note: TL: Total lipid, PL: Phospholipid, AA: Arachidonic acid In the table, values in parentheses were recognized as abnormal values, and were excluded from the calculation of average values.
【００１５】表２は、肝臓及び脾臓からの抽出物は、総
脂質及びリン脂質の構成脂肪酸としてアラキドン酸を高
濃度で含有しており、これらの臓器が本発明の原料とし
て適することを示している。小腸の場合、総脂質の含有
量が低いが、リン脂質の構成脂肪酸のうちアラキドン酸
含有量が高いことから、原料として利用可能である。し
かし、胃と大腸は、総脂質及びリン脂質の各アラキドン
酸含有量の点で、原料として不適当と考えられる。本実
施例で得られたリン脂質、特に肝臓、脾臓、及び小腸か
ら得られた製品は従来の卵黄からのリン脂質製品（構成
脂肪酸中、アラキドン酸含有量は、１〜５重量％）に比
較して、構成脂肪酸のうちアラキドン酸含有量が高く、
リン脂質にも富むことから、アラキドン酸を強化した組
成物とりわけ育児用粉ミルクの添加物として好適であ
る。Table 2 shows that extracts from liver and spleen contain high concentrations of arachidonic acid as a constituent fatty acid of total lipids and phospholipids, and these organs are suitable as raw materials of the present invention. I have. In the case of the small intestine, the content of total lipids is low, but the content of arachidonic acid among the constituent fatty acids of phospholipids is high, so that it can be used as a raw material. However, the stomach and large intestine are considered to be unsuitable as raw materials in terms of the arachidonic acid content of total lipids and phospholipids. The phospholipids obtained in this example, especially products obtained from the liver, spleen, and small intestine, were compared with conventional phospholipid products from yolk (the content of arachidonic acid in the constituent fatty acids was 1 to 5% by weight). And the arachidonic acid content of the constituent fatty acids is high,
Because it is rich in phospholipids, it is suitable as an additive to a composition enriched with arachidonic acid, especially an infant milk powder.
【００１６】実施例２ 牛の肝臓を用いて、実施例１と同様に乾燥し（乾燥物の
水分含量２５．６重量％）、ヘキサン−エタノール
（１：１）混合溶剤により抽出次いでろ過し、抽出液か
ら溶剤を留去して総脂質を得た。さらにこれをアセトン
処理してリン脂質を得た。また、得られた各脂質の構成
脂肪酸のメチルエステル化物をガスクロマトグラフィー
で分析した結果、総脂質含有率１５．７％；総脂質中の
アラキドン酸含有率１８．５％；総脂質中のリン脂質含
有率４１．７％、リン脂質中のアラキドン酸含有率２
２．５％であった。これは、牛の内臓も本発明の原料に
適することを示している。 Example 2 Using bovine liver, drying was performed in the same manner as in Example 1 (moisture content of the dried product: 25.6% by weight), extracted with a mixed solvent of hexane-ethanol (1: 1) and filtered. The solvent was distilled off from the extract to obtain total lipids. This was further treated with acetone to obtain a phospholipid. Further, as a result of analyzing the obtained methyl ester of the constituent fatty acid of each lipid by gas chromatography, the total lipid content was 15.7%; the arachidonic acid content in the total lipid was 18.5%; Lipid content 41.7%, arachidonic acid content 2 in phospholipids
2.5%. This indicates that beef offal is also suitable for the raw material of the present invention.
【００１７】実施例３ 市販の乳児用調製粉乳（森永乳業（株）製、商品名：森
永ドライミルク）１００ｇに、アラキドン酸高含有脂質
（豚の肝臓及び脾臓の混合物から実施例１記載の方法で
抽出、精製したもの。総脂質中のリン脂質含有率：８
４．０重量％、リン脂質の構成脂肪酸のうちアラキドン
酸含有率：２３．５重量％。）２．５ｇを混合してアラ
キドン酸高含有調製粉乳を試作した。本試作品には、１
００ｇあたりアラキドン酸が５５０ｍｇ含まれ、そのう
ち４９０ｍｇがリン脂質の形態で含有されており、粉末
状態、及びこれを温湯に溶解ないし分散させたミルク状
態のいずれにおいても風味や食感に違和感がないもので
あった。 Example 3 A method as described in Example 1 was prepared by adding 100 g of a commercially available infant formula (Morinaga Milk Co., Ltd., trade name: Morinaga dry milk) to a lipid rich in arachidonic acid (a mixture of pig liver and spleen). Extracted and purified in step 2. Phospholipid content in total lipid: 8
4.0% by weight, arachidonic acid content of the constituent fatty acids of the phospholipid: 23.5% by weight. ) 2.5 g was mixed to prepare an arachidonic acid-rich formula milk powder. In this prototype, 1
Contains 550 mg of arachidonic acid per 00 g, of which 490 mg is contained in the form of phospholipid, and has no unpleasant taste or texture in both powdered form and milk form in which this is dissolved or dispersed in hot water. Met.
【００１８】[0018]
【発明の効果】本発明によれば、構成脂肪酸中アラキド
ン酸を多量に含むリン脂質及び該リン脂質を主成分とし
て含む脂質を簡便かつ安全に製造することができる。本
発明により得られるアラキドン酸高含有リン脂質及び該
リン脂質含有脂質は食品、医薬品等の分野において好適
なアラキドン酸供給源として利用でき、とりわけ粉ミル
クや離乳食等の乳幼児用食品への添加物等として有用で
ある。According to the present invention, a phospholipid containing a large amount of arachidonic acid in a constituent fatty acid and a lipid containing the phospholipid as a main component can be easily and safely produced. The arachidonic acid-rich phospholipid and the phospholipid-containing lipid obtained by the present invention can be used as a suitable source of arachidonic acid in the fields of foods, pharmaceuticals, and the like, and particularly as an additive to infant foods such as powdered milk and baby food. Useful.
Claims (9)
出し、次いで、該溶剤を留去することを特徴とするアラ
キドン酸含有リン脂質を主成分とする脂質の製造法。1. A method for producing a lipid comprising arachidonic acid-containing phospholipid as a main component, comprising drying an internal organ of a domestic animal, extracting the organ with an organic solvent, and distilling off the solvent.
法。2. The method according to claim 1, wherein the livestock is a pig or a cow.
１又は２に記載の方法。3. The method according to claim 1, wherein the internal organ is a liver, spleen or small intestine.
の混合物である請求項１〜３のいずれか１項に記載の方
法。4. The method according to claim 1, wherein the organic solvent is ethanol, hexane or a mixture thereof.
請求項１〜４のいずれか１項に記載の方法。5. The method according to claim 1, wherein the drying and the removal of the solvent are carried out at 70 ° C. or lower.
法で得られたアラキドン酸含有リン脂質を主成分とする
脂質。6. A lipid containing arachidonic acid-containing phospholipid as a main component, which is obtained by the method according to any one of claims 1 to 5.
含有率が１０〜５０％の範囲である、請求項６に記載の
脂質。7. The lipid according to claim 6, wherein the arachidonic acid content in the constituent fatty acids of the phospholipid is in the range of 10 to 50%.
有リン脂質を主成分とする脂質を配合してなる食品組成
物。8. A food composition comprising the lipid containing the arachidonic acid-containing phospholipid according to claim 6 or 7 as a main component.
８に記載の食品組成物。9. The food composition according to claim 8, wherein the composition is an infant formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22419497A JPH1135587A (en) | 1997-07-15 | 1997-07-15 | Production of lipid consisting essentially of arachidonic acid-containing lipid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22419497A JPH1135587A (en) | 1997-07-15 | 1997-07-15 | Production of lipid consisting essentially of arachidonic acid-containing lipid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH1135587A true JPH1135587A (en) | 1999-02-09 |
Family
ID=16810003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22419497A Pending JPH1135587A (en) | 1997-07-15 | 1997-07-15 | Production of lipid consisting essentially of arachidonic acid-containing lipid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH1135587A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007144472A1 (en) * | 2006-06-16 | 2007-12-21 | Helsingfors Institution För Bioimmunterapi Ab | Dairy based foodstuff containing central nervous system lipids |
| US7847113B2 (en) | 2004-03-01 | 2010-12-07 | Suntory Holdings Limited | Phospholipids including long-chain polyunsaturated fatty acids as constituents, and use of such phospholipids |
| JP2021155565A (en) * | 2020-03-27 | 2021-10-07 | 株式会社 ビーアンドエス・コーポレーション | Method for producing functional material containing ether-type glycerophospholipids |
-
1997
- 1997-07-15 JP JP22419497A patent/JPH1135587A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7847113B2 (en) | 2004-03-01 | 2010-12-07 | Suntory Holdings Limited | Phospholipids including long-chain polyunsaturated fatty acids as constituents, and use of such phospholipids |
| US7968737B2 (en) | 2004-03-01 | 2011-06-28 | Suntory Holdings Limited | Producing method of phospholipids including long-chain polyunsaturated fatty acids as constituents, and use of such phospholipids |
| WO2007144472A1 (en) * | 2006-06-16 | 2007-12-21 | Helsingfors Institution För Bioimmunterapi Ab | Dairy based foodstuff containing central nervous system lipids |
| US8110227B2 (en) | 2006-06-16 | 2012-02-07 | Oy Neurofood Ab | Dairy based foodstuff containing central nervous system lipids |
| JP2021155565A (en) * | 2020-03-27 | 2021-10-07 | 株式会社 ビーアンドエス・コーポレーション | Method for producing functional material containing ether-type glycerophospholipids |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0304819B1 (en) | Animal feed supplement | |
| EP2335494A1 (en) | Method for concentrating lipid | |
| WO1999021434A1 (en) | Composition containing useful substances originating in fishes and shellfishes and process for the preparation of the substances | |
| FR2541897A1 (en) | PROCESS FOR THE PREPARATION OF EXTRACTS FROM FISH, MOLLUSCS AND CRUSTACEANS USED AS MEDICAMENTS, IN PARTICULAR IN THE TREATMENT OF ULCERS, DIABETES AND LIPEMIA | |
| AU2020286152A1 (en) | One step procedure for producing a protein oleogel | |
| JPH09194362A (en) | Composition consisting of phospholipid containing docosahexanenoic acid and eicosapentanenoic acid | |
| JP6056093B2 (en) | Health promoting food containing ethyl ester of fatty acid as linen oil and method for producing the same | |
| EP0519916B1 (en) | Process for enrichment of fat with regard to polyunsaturated fatty acids and phospholipids, and application of such enriched fat | |
| JPH0517918B2 (en) | ||
| JPH1135587A (en) | Production of lipid consisting essentially of arachidonic acid-containing lipid | |
| JPH08325192A (en) | Production of phospholipid containing docosahexaenoic acid | |
| JP2009269865A (en) | Oral administration agent | |
| JP2013031415A (en) | Method of manufacturing food including function nutrient composition obtained by extracting unused part of beef cattle as raw material | |
| JP7021953B2 (en) | Method for producing ether-type glycerophospholipid | |
| JP4273741B2 (en) | Fish oil odor masking method | |
| JPH10237480A (en) | Fat and oil composition | |
| KR101370457B1 (en) | Annimal food comprising omega-3 fatic acid | |
| JPH08275734A (en) | Production of feed additive | |
| JP7466852B2 (en) | Methods for Producing Compositions Comprising Collagen Peptides | |
| JP5167199B2 (en) | Emulsified liquid nutritional food | |
| RU2183414C1 (en) | Biologically active additive and method of its production | |
| WO2021231586A1 (en) | Method for producing fish oil | |
| JPH06343388A (en) | Milk composition | |
| JPH05252901A (en) | Food additive for supplementing vitamin d | |
| JPH01247045A (en) | Feed for broiler |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040714 |
|
| A711 | Notification of change in applicant |
Effective date: 20050225 Free format text: JAPANESE INTERMEDIATE CODE: A711 |
|
| A521 | Written amendment |
Effective date: 20050506 Free format text: JAPANESE INTERMEDIATE CODE: A523 |
|
| A521 | Written amendment |
Effective date: 20050708 Free format text: JAPANESE INTERMEDIATE CODE: A523 |
|
| A977 | Report on retrieval |
Effective date: 20061102 Free format text: JAPANESE INTERMEDIATE CODE: A971007 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070306 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20070821 |