JP2002265360A - Neutral fat-reducing agent - Google Patents
Neutral fat-reducing agentInfo
- Publication number
- JP2002265360A JP2002265360A JP2001061472A JP2001061472A JP2002265360A JP 2002265360 A JP2002265360 A JP 2002265360A JP 2001061472 A JP2001061472 A JP 2001061472A JP 2001061472 A JP2001061472 A JP 2001061472A JP 2002265360 A JP2002265360 A JP 2002265360A
- Authority
- JP
- Japan
- Prior art keywords
- conjugated
- fatty acid
- acid
- reducing agent
- neutral fat
- 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
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、血清及び肝臓中の
中性脂肪を低減させる中性脂肪低減剤に関する。TECHNICAL FIELD The present invention relates to a neutral fat reducing agent for reducing neutral fat in serum and liver.
【０００２】[0002]
【従来の技術】近年、過食や運動不足、食生活の欧米化
に伴い動物性脂肪の摂取増加により、血液中のトリグリ
セリドやコレステロール等の中性脂肪が正常範囲を越え
て増加した状態、いわゆる高脂血症が増え、これに伴う
動脈硬化や脳卒中等が問題となっている。高脂血症は自
覚症状はないが、治癒には長時間を有し、継続的な治療
が必要な病気である。従って、安全性が高く、日常的に
投与あるいは摂取しても副作用が生じず、また食事等に
添加しても味に影響することのない中性脂肪の低減効果
のある素材が求められている。2. Description of the Related Art In recent years, due to the overeating, lack of exercise, and the westernization of dietary habits, the intake of animal fats has increased, and the triglyceride and cholesterol levels of triglycerides and cholesterol in the blood have increased beyond the normal range. Lipidemia is increasing, and arteriosclerosis and stroke associated therewith are becoming problems. Hyperlipidemia has no subjective symptoms, but has a long time to heal and is a disease requiring continuous treatment. Therefore, there is a need for a material that is highly safe, has no side effects even when administered or ingested daily, and has a neutral fat reducing effect that does not affect the taste even when added to a meal or the like. .
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、優れ
た中性脂肪低減作用を有し、且つ安全性が高く副作用の
少ない脂肪酸又はその誘導体を有効成分として含有する
中性脂肪低減剤を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a neutral fat reducing agent containing a fatty acid or a derivative thereof having an excellent action of reducing neutral fat and having high safety and few side effects as an active ingredient. To provide.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、上記目的
を達成するために鋭意研究を重ねた結果、共役長鎖高度
不飽和脂肪酸が優れた中性脂肪低減作用を有しているこ
とを知見した。Means for Solving the Problems The present inventors have made intensive studies to achieve the above object, and as a result, have found that conjugated long-chain highly unsaturated fatty acids have an excellent neutral fat reducing action. Was found.
【０００５】本発明は、上記知見にもとづいてなされた
もので、共役二重結合を有する炭素数２０以上の脂肪
酸、あるいは該脂肪酸の、エステルもしくは金属塩又は
その他の薬理学上許容される形態物を有効成分とする血
清及び肝臓中の中性脂肪低減剤を提供するものである。The present invention has been made based on the above findings, and is a fatty acid having 20 or more carbon atoms having a conjugated double bond, or an ester or metal salt of the fatty acid or other pharmaceutically acceptable forms thereof. And an agent for reducing serum neutral fat in the liver and liver.
【０００６】また、本発明は、上記脂肪酸が、全共役二
重結合中に、共役ジエンを４０〜７０％及びトリエン以
上の共役ポリエンを６０〜３０％含むものである上記中
性脂肪低減剤を提供するものである。The present invention also provides the neutral fat reducing agent, wherein the fatty acid contains 40 to 70% of a conjugated diene and 60 to 30% of a conjugated polyene of at least triene in the total conjugated double bond. Things.
【０００７】また、本発明は、上記脂肪酸が、共役アラ
キドン酸、共役エイコサペンタエン酸、共役ドコサヘキ
サエン酸、共役ドコサペンタエン酸及びα−エレオステ
アリン酸からなる群から選ばれた１種又は２種以上の脂
肪酸である上記中性脂肪低減剤を提供するものである。[0007] The present invention also relates to the present invention, wherein the fatty acid is one or two selected from the group consisting of conjugated arachidonic acid, conjugated eicosapentaenoic acid, conjugated docosahexaenoic acid, conjugated docosapentaenoic acid and α-eleostearic acid. An object of the present invention is to provide the above neutral fat reducing agent which is a fatty acid.
【０００８】また、本発明は、上記脂肪酸のエステル
が、上記脂肪酸と、炭素数１〜１０のアルコール、エチ
レングリコール、プロピレングリコール及びグリセリン
からなる群から選ばれた１種又は２種以上のアルコール
類とのエステルである上記中性脂肪低減剤を提供するも
のである。[0008] The present invention also relates to the present invention, wherein the ester of the fatty acid is one or more alcohols selected from the group consisting of the fatty acid and an alcohol having 1 to 10 carbon atoms, ethylene glycol, propylene glycol and glycerin. And a neutral fat reducing agent, which is an ester of the above.
【０００９】また、本発明は、上記脂肪酸の金属塩が、
ナトリウム塩、カリウム塩、カルシウム塩、亜鉛塩及び
マグネシウム塩からなる群から選ばれた１種又は２種以
上の塩である上記中性脂肪低減剤を提供するものであ
る。[0009] Further, the present invention provides the above-mentioned metal salt of a fatty acid,
An object of the present invention is to provide the above neutral fat reducing agent, which is one or more salts selected from the group consisting of sodium salt, potassium salt, calcium salt, zinc salt and magnesium salt.
【００１０】また、本発明は、上記の何れかの中性脂肪
低減剤を含有する飲食品を提供するものである。[0010] The present invention also provides a food or drink containing any of the above neutral fat reducing agents.
【００１１】[0011]
【発明の実施の形態】以下、本発明の中性脂肪低減剤に
ついて詳述する。本発明の中性脂肪低減剤の有効成分で
ある脂肪酸は、上述のとおり、共役二重結合を有する炭
素数２０以上の脂肪酸（以下、共役長鎖高度不飽和脂肪
酸という）であり、炭素数が上記範囲外となると本発明
の目的とするような優れた中性脂肪低減作用が得られな
い。BEST MODE FOR CARRYING OUT THE INVENTION The neutral fat reducing agent of the present invention will be described in detail below. As described above, the fatty acid that is an active ingredient of the neutral fat reducing agent of the present invention is a fatty acid having a conjugated double bond and having 20 or more carbon atoms (hereinafter, referred to as a conjugated long-chain highly unsaturated fatty acid), If the amount is outside the above range, an excellent neutral fat reducing effect as intended by the present invention cannot be obtained.
【００１２】このような共役長鎖高度不飽和脂肪酸とし
ては、共役アラキドン酸（ＣＡＡ）、共役エイコサペン
タエン酸（ＣＥＰＡ）、共役ドコサヘキサエン酸（ＣＤ
ＨＡ）、共役ドコサペンタエン酸（ＣＤＰＡ）、α−エ
レオステアリン酸（α−ＥＳ）等の共役長鎖高度不飽和
脂肪酸及びこれらの共役長鎖高度不飽和脂肪酸を２種以
上混合した共役長鎖高度不飽和脂肪酸組成物等が挙げら
れるが、これらの例示に限定されるものではない。Such conjugated long-chain highly unsaturated fatty acids include conjugated arachidonic acid (CAA), conjugated eicosapentaenoic acid (CEPA), and conjugated docosahexaenoic acid (CD
HA), conjugated docosapentaenoic acid (CDPA), α-eleostearic acid (α-ES), and other conjugated long-chain highly unsaturated fatty acids, and conjugate lengths obtained by mixing two or more of these conjugated long-chain highly unsaturated fatty acids. Examples thereof include high-chain unsaturated fatty acid compositions, but are not limited to these examples.
【００１３】上記共役長鎖高度不飽和脂肪酸は、脂肪酸
のままでもよく、エステルもしくは金属塩の形態であっ
てもよい。上記共役長鎖高度不飽和脂肪酸のエステルと
しては、上記共役長鎖高度不飽和脂肪酸と、炭素数１〜
１０のアルコール、エチレングリコール、プロピレング
リコール及びグリセリンからなる群から選ばれた１種又
は２種以上のアルコール類とのエステル等が挙げられ
る。また、上記共役長鎖高度不飽和脂肪酸の金属塩とし
ては、ナトリウム塩、カリウム塩、カルシウム塩、亜鉛
塩及びマグネシウム塩からなる群から選ばれた１種又は
２種以上の金属塩等が挙げられる。The conjugated long-chain highly unsaturated fatty acid may be a fatty acid, or may be in the form of an ester or a metal salt. As the ester of the conjugated long-chain highly unsaturated fatty acid, the conjugated long-chain highly unsaturated fatty acid,
And an ester with one or more alcohols selected from the group consisting of 10 alcohols, ethylene glycol, propylene glycol and glycerin. Further, examples of the metal salt of the conjugated long-chain highly unsaturated fatty acid include one or more metal salts selected from the group consisting of sodium salt, potassium salt, calcium salt, zinc salt and magnesium salt. .
【００１４】さらに、上記共役長鎖高度不飽和脂肪酸
は、上記のエステルもしくは金属塩の形態の他、アミド
やリン脂質等の任意の他の薬理学上許容される形態物で
あってもよい。The conjugated long-chain highly unsaturated fatty acid may be in the form of the above-mentioned ester or metal salt, or may be in any other pharmacologically acceptable form such as amide or phospholipid.
【００１５】上記共役長鎖高度不飽和脂肪酸は、通常の
方法、即ち長鎖高度不飽和脂肪酸、そのエステル又は長
鎖高度不飽和脂肪酸を含有する油脂（魚油等）をエチレ
ングリコールに代表される有機溶媒中にてアルカリ共役
化することにより容易に得られる。共役化率は、反応条
件を制御することにより８０％以上、好ましくは９０％
以上、特に好ましくは９５％以上とするのがよい。The conjugated long-chain polyunsaturated fatty acid is prepared by a conventional method, that is, by converting a long-chain polyunsaturated fatty acid, an ester thereof, or a fat or oil (such as fish oil) containing the long-chain polyunsaturated fatty acid into an organic compound represented by ethylene glycol. It can be easily obtained by alkali conjugation in a solvent. The conjugation rate is controlled to 80% or more, preferably 90%, by controlling the reaction conditions.
Above, particularly preferably 95% or more.
【００１６】また、上記共役長鎖高度不飽和脂肪酸は、
全共役二重結合中に、共役ジエンを４０〜７０％及びト
リエン以上の共役ポリエンを６０〜３０％含むものが好
ましい。さらに好ましくは、トリエン以上の共役ポリエ
ンとして、全共役二重結合中に、共役トリエンを１５〜
３５％、共役テトラエンを１０〜２０％、それ以上の共
役ポリエンを３〜１５％含むものである。Further, the conjugated long-chain highly unsaturated fatty acid is
It is preferable that the total conjugated double bond contains 40 to 70% of a conjugated diene and 60 to 30% of a conjugated polyene of at least triene. More preferably, as a conjugated polyene equal to or greater than a triene, a conjugated triene in all conjugated double bonds is 15 to
35%, 10 to 20% of a conjugated tetraene, and 3 to 15% of a conjugated polyene.
【００１７】全共役二重結合中に含まれる共役ジエン、
共役トリエン等の含有割合は、共役長鎖高度不飽和脂肪
酸のＵＶスペクトルを測定することにより算出すること
ができる。即ち、既知濃度の共役長鎖高度不飽和脂肪酸
の２，２，４−トリメチルペンタン溶液（又はヘキサ
ン、ヘプタン、シクロヘキサン溶液）を吸収セルに入
れ、溶解に用いた溶剤を対照にして、２３３、２６２、
２６８、２７４、３０８、３１５、３２２及び３４６ｎ
ｍの吸光度を測定する。得られた吸光度から規定の計算
式（日本油化学協会編、基準油脂分析試験法2.4.3.1)に
従って、共役ジエン酸、共役トリエン酸、共役テトラエ
ン酸、共役ペンタエン酸の含有割合を算出する。A conjugated diene contained in all conjugated double bonds,
The content ratio of the conjugated triene or the like can be calculated by measuring the UV spectrum of the conjugated long-chain highly unsaturated fatty acid. That is, a 2,2,4-trimethylpentane solution (or a hexane, heptane, or cyclohexane solution) of a conjugated long-chain highly unsaturated fatty acid of a known concentration is placed in an absorption cell, and the solvent used for dissolution is used as a control, and 233,262. ,
268, 274, 308, 315, 322 and 346n
Measure absorbance at m. From the obtained absorbance, the content ratio of conjugated dienoic acid, conjugated trienoic acid, conjugated tetraenoic acid, and conjugated pentaenoic acid is calculated according to a prescribed calculation formula (edited by the Japan Oil Chemists' Society, Standard Fatty Acid Analysis Test Method 2.4.3.1).
【００１８】また、上記共役長鎖高度不飽和脂肪酸を含
む油脂をそのまま、あるいは加工して使用してもよい。
例えば、α−エレオステアリン酸を含有する桐油及びに
がうり種子油等が挙げられる。また、魚油中にも、少量
の上記共役長鎖高度不飽和脂肪酸が含まれており、また
魚油はＤＨＡ、ＥＰＡ等の長鎖高度不飽和脂肪酸を多量
に含んでおり、これを焼くことにより、少量の上記共役
高度不飽和脂肪酸が生成するので、これらを利用するこ
ともできる。The fat or oil containing the conjugated long-chain highly unsaturated fatty acid may be used as it is or after processing.
Examples include tung oil and bittern seed oil containing α-eleostearic acid. In addition, fish oil also contains a small amount of the above-mentioned conjugated long-chain highly unsaturated fatty acids, and fish oil contains a large amount of long-chain highly unsaturated fatty acids such as DHA and EPA. Since a small amount of the above-mentioned conjugated polyunsaturated fatty acid is produced, these can also be used.
【００１９】上記共役長鎖高度不飽和脂肪酸の中性脂肪
低減剤としての作用機序は不明である。しかしながら、
上記共役長鎖高度不飽和脂肪酸を有効成分とする本発明
の中性脂肪低減剤は、後述の実施例に示すように優れた
中性脂肪低減作用を示す。従って、本発明の中性脂肪低
減剤を様々な様態で投与することにより極めて有効な中
性脂肪低減効果を示すと期待される。本発明の中性脂肪
低減剤は、高脂血症の治療のための投与のみならず、予
防のために投与してもよい。The mechanism of action of the conjugated long-chain highly unsaturated fatty acid as a neutral fat reducing agent is unknown. However,
The neutral fat reducing agent of the present invention containing the above-mentioned conjugated long-chain highly unsaturated fatty acid as an active ingredient shows an excellent neutral fat reducing action as shown in Examples described later. Therefore, it is expected that the administration of the neutral fat reducing agent of the present invention in various modes will exhibit a very effective neutral fat reducing effect. The neutral fat reducing agent of the present invention may be administered not only for treatment of hyperlipidemia but also for prevention.
【００２０】上記共役長鎖高度不飽和脂肪酸、該脂肪酸
のエステルもしくは金属塩又はその他の形態物を有効成
分とする本発明の中性脂肪低減剤の形態は、制限される
ものではなく、注射液、座薬、軟膏、錠剤、カプセル
剤、散剤、顆粒剤、ドリンク剤等の種々の形態を適宜選
択することができる。本発明の中性脂肪低減剤には、上
記形態に応じて、薬理上許される希釈剤、安定剤、賦形
剤等を含有させることができる。本発明の中性脂肪低減
剤中の、上記共役長鎖高度不飽和脂肪酸、該脂肪酸のエ
ステルもしくは金属塩又はその他の形態物の含有量は、
後述する投与量（治療上有効量）を目安にし、１日の服
用回数や用量を考慮して決定すればよい。The form of the neutral fat reducing agent of the present invention comprising the above-mentioned conjugated long-chain highly unsaturated fatty acid, ester or metal salt of the fatty acid or other forms as an active ingredient is not limited. , Suppositories, ointments, tablets, capsules, powders, granules, drinks and the like can be appropriately selected. The neutral fat reducing agent of the present invention may contain pharmacologically acceptable diluents, stabilizers, excipients, and the like, depending on the form. In the neutral fat reducing agent of the present invention, the content of the conjugated long-chain highly unsaturated fatty acid, the ester or metal salt of the fatty acid or other forms,
The dose may be determined in consideration of the dose (therapeutically effective amount) described later and the number of doses and doses per day.
【００２１】本発明の中性脂肪低減剤の投与方法として
は、静脈内注射、皮下注射、座薬、軟膏等による非経口
投与法、錠剤、カプセル剤、散剤、顆粒剤等による経口
投与法が可能である。また、本発明の中性脂肪低減剤
は、食用油脂組成物、食用乳化油脂組成物、ベーカリー
製品、調理食品、飲料等の飲食品に混合して用いてもよ
い。このような飲食品としては、具体的にはマーガリ
ン、ショートニング、クリーム、アイスクリーム、バタ
ー、チーズ、スープ、パン、ケーキ、ビスケット、クラ
ッカー、クッキー、ジャム等が挙げられるが、これらに
限定されるものではない。The method for administering the neutral fat reducing agent of the present invention includes intravenous injection, subcutaneous injection, parenteral administration using suppositories, ointments and the like, and oral administration using tablets, capsules, powders, granules and the like. It is. Further, the neutral fat reducing agent of the present invention may be used as a mixture with edible fat and oil compositions, edible emulsified fat and oil compositions, bakery products, cooked foods, and foods and beverages such as beverages. Specific examples of such foods and drinks include, but are not limited to, margarine, shortening, cream, ice cream, butter, cheese, soup, bread, cake, biscuits, crackers, cookies, jams, and the like. is not.
【００２２】本発明の中性脂肪低減剤の投与量は、治療
上有効量であり、高脂血症の症状の度合いにより一概に
言えないが、大凡、例えば成人（体重６０kg）の場合、
１日当たり上記共役長鎖高度不飽和脂肪酸の量として１
２０〜８，７００ｍｇ、好ましくは１５６〜１，５６０
ｍｇである。本発明の中性脂肪低減剤は、適宜、公知の
中性脂肪低減剤を含む他の治療薬と併用することもでき
る。The dosage of the neutral fat reducing agent of the present invention is a therapeutically effective amount, and cannot be determined unconditionally depending on the degree of the symptoms of hyperlipidemia.
The amount of the conjugated long-chain highly unsaturated fatty acid per day is 1
20 to 8,700 mg, preferably 156 to 1,560
mg. The neutral fat reducing agent of the present invention can be used in combination with other therapeutic agents including known neutral fat reducing agents as appropriate.
【００２３】[0023]
【実施例】以下、実施例により本発明を具体的に説明す
るが、本発明は、これらの実施例により何等制限される
ものではない。EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited to these examples.
【００２４】実施例１ エチレングリコール３００ｇ及び水酸化カリウム１００
ｇを２リットル容四つ口フラスコに入れ、窒素を吹き込
みながら、１００℃まで昇温した。次にエイコサペンタ
エン酸エチル２００ｇをフラスコに加え、窒素気流下、
２．５時間加熱した。反応溶液を室温まで冷却した後、
塩酸を加えて反応溶液のｐＨをｐＨ３に調整し、さらに
蒸留水５０ｍｌを加えて、５分間撹拌した。次いで、ヘ
キサン抽出を３回行った後、ヘキサン溶液を５％ＮａＣ
ｌ、蒸留水で順次洗浄した。ヘキサン溶液に無水硫酸ナ
トリウムを加えて脱水濾過後、ロータリーエバポレータ
ーを用いてヘキサンを留去し、共役エイコサペンタエン
酸（ＣＥＰＡ）を得た。得られた共役エイコサペンタエ
ン酸中の共役不飽和脂肪酸含量をＵＶスペクトル法（日
本油化学協会編、基準油脂分析試験法2.4.3.1)により測
定したところ、共役化率は９９．１％であった。また、
全共役二重結合中の各エンの割合は、共役ジエン５１
％、共役トリエン２３％、共役テトラエン１７％、共役
ペンタエン９％であった。得られた本発明品の共役エイ
コサペンタエン酸について、後記の＜試験＞を行った。Example 1 300 g of ethylene glycol and 100 of potassium hydroxide
g was placed in a two-liter four-necked flask and heated to 100 ° C. while blowing nitrogen. Next, 200 g of ethyl eicosapentaenoate was added to the flask, and under a nitrogen stream,
Heated for 2.5 hours. After cooling the reaction solution to room temperature,
The pH of the reaction solution was adjusted to pH 3 by adding hydrochloric acid, 50 ml of distilled water was further added, and the mixture was stirred for 5 minutes. Then, after hexane extraction was performed three times, the hexane solution was extracted with 5% NaC.
1 and sequentially washed with distilled water. Anhydrous sodium sulfate was added to the hexane solution, and after dehydration filtration, hexane was distilled off using a rotary evaporator to obtain conjugated eicosapentaenoic acid (CEPA). The conjugated unsaturated fatty acid content in the obtained conjugated eicosapentaenoic acid was measured by a UV spectrum method (edited by the Japan Oil Chemists' Society, Standard Fatty Acid Analysis Test Method 2.4.3.1), and the conjugation ratio was 99.1%. . Also,
The proportion of each ene in the total conjugated double bond is conjugated diene 51
%, Conjugated triene 23%, conjugated tetraene 17%, and conjugated pentaene 9%. <Test> described below was performed on the obtained conjugated eicosapentaenoic acid of the product of the present invention.
【００２５】実施例２及び３ 実施例１の製法に準じて、共役ドコサヘキサエン酸（Ｃ
ＤＨＡ）及び共役アラキドン酸（ＣＡＡ）をそれぞれ得
た。これらの共役化率及び全共役二重結合中の各エンの
割合は次の通りであった。 （共役ドコサヘキサエン酸） ・共役化率；９９％・共役ジエン；５１％・共役トリエ
ン；１８％・共役テトラエン；１８％・共役ペンタエ
ン；１３％ （共役アラキドン酸） ・共役化率；９７％・共役ジエン；６６％・共役トリエ
ン；２２％・共役テトラエン；１２％ 得られた本発明品の共役ドコサヘキサエン酸（実施例
２）及び共役アラキドン酸（実施例３）について、後記
の＜試験＞を行った。Examples 2 and 3 According to the production method of Example 1, conjugated docosahexaenoic acid (C
DHA) and conjugated arachidonic acid (CAA), respectively. The conjugation ratio and the ratio of each ene in the total conjugated double bond were as follows. (Conjugated docosahexaenoic acid) Conjugation ratio; 99% Conjugated diene; 51% Conjugated triene; 18% Conjugated tetraene; 18% Conjugated pentaene; 13% Conjugated arachidonic acid Conjugation ratio; 97% Conjugated Diene: 66% conjugated triene; 22% conjugated tetraene; 12% The conjugated docosahexaenoic acid (Example 2) and the conjugated arachidonic acid (Example 3) of the obtained product of the present invention were subjected to the following <test>. .
【００２６】実施例４ α−エレオステアリン酸（シス−９、トランス−１１、
トランス−１３−オクタデカトリエン酸）を用いて、後
記の＜試験＞を行った。Example 4 α-eleostearic acid (cis-9, trans-11,
(Trans-13-octadecatrienoic acid), and the following <test> was performed.
【００２７】比較例１〜５ エイコサペンタエン酸（ＥＰＡ、比較例１）、ドコサヘ
キサエン酸（ＤＨＡ、比較例２）、アラキドン酸（Ａ
Ａ、比較例３）、リノール酸（ＬＡ、比較例４）及び共
役リノール酸（ＣＬＡ、比較例５）を被験物質として用
いた以外は実施例と同様に、下記の＜試験＞を行った。Comparative Examples 1 to 5 Eicosapentaenoic acid (EPA, Comparative Example 1), docosahexaenoic acid (DHA, Comparative Example 2), arachidonic acid (A
A, Comparative Example 3), linoleic acid (LA, Comparative Example 4) and conjugated linoleic acid (CLA, Comparative Example 5) were used in the same manner as in Example except that the following <test> was performed.
【００２８】＜試験＞雄ラットに、３週間、試験油脂を
１０重量％含む飼料を摂取させた。試験油脂は、パーム
／大豆（１：１）混合油（control)をベースとして油脂
中の１０重量％（飼料中の１重量％）が当該共役脂肪酸
となるように調整した。また、試験油脂のP/M/S 比を一
定（約１）にして脂肪酸組成が偏った食餌条件を避け
た。試験期間終了後、約８時間絶食させてエーテル麻酔
下で腹大動脈より採血し、各組織を回収した。血漿中の
脂質として、総コレステロール、ＨＬＤコレステロー
ル、トリグリセリド、リン脂質の量を常法により測定し
た。また、ＨＬＤ／総コレステロールの値を計算した。
これらの結果を下記表１に示す。また、血漿と肝臓中の
ＰＧ（プロスタグランジン）をPowellの方法に従ってSe
p-PakC18カートリッジ（Waters）を用いて精製後、ＥＩ
Ａ法による市販分析キット（Amersham）を用いてＰＧＥ
2 レベル（プロスタグランジンＥ2 レベル）を測定し
た。その結果を下記表２に示す。下記表２に示す結果よ
り、本発明品（実施例１〜４）を摂取させたラットは代
謝系に異常が見られないことから、本発明品は安全性が
高く副作用が少ないことがわかる。<Test> Male rats were fed a diet containing 10% by weight of test oils and fats for 3 weeks. The test fat was adjusted so that 10% by weight in fat (1% by weight in feed) was the conjugated fatty acid based on a palm / soybean (1: 1) mixed oil (control). The P / M / S ratio of the test fat was kept constant (about 1) to avoid dietary conditions in which the fatty acid composition was uneven. After the end of the test period, the animals were fasted for about 8 hours, and blood was collected from the abdominal aorta under ether anesthesia to recover each tissue. The amounts of total cholesterol, HLD cholesterol, triglycerides, and phospholipids as plasma lipids were measured by a conventional method. Also, the value of HLD / total cholesterol was calculated.
The results are shown in Table 1 below. In addition, PG (prostaglandin) in plasma and liver was purified according to Powell's method.
After purification using p-PakC 18 cartridge (Waters), EI
PGE using commercial analysis kit (Amersham) by Method A
Was measured a two-level (prostaglandin E 2 level). The results are shown in Table 2 below. The results shown in Table 2 below show that the rats ingested with the product of the present invention (Examples 1 to 4) showed no abnormalities in the metabolic system, indicating that the product of the present invention is highly safe and has few side effects.
【００２９】[0029]
【表１】 [Table 1]
【００３０】[0030]
【表２】 [Table 2]
【００３１】実施例５（マーガリンの製造例） パーム油：パーム硬化油：菜種油：ソルビタン脂肪酸エ
ステルを、３０：５０：２０：０．３の割合（重量比）
で含有する食用油脂１００部（重量部、以下同じ）を７
０℃で融解し、これに実施例１で得た共役エイコサペン
タエン酸（ＣＥＰＡ）５部を添加し、ホモミキサーで攪
拌しながら、７０℃に加温した水１６部に脱脂粉乳０．
５部及び食塩１部を溶解させた溶液を徐々に添加・混合
した後、急冷可塑化を行い、本発明のマーガリン（共役
長鎖高度不飽和脂肪酸含量４．０重量％）を得た。Example 5 (Production example of margarine) Palm oil: palm hydrogenated oil: rapeseed oil: sorbitan fatty acid ester in a ratio of 30: 50: 20: 0.3 (weight ratio)
100 parts (parts by weight, hereinafter the same) of edible oils and fats contained in 7
The mixture was melted at 0 ° C., 5 parts of the conjugated eicosapentaenoic acid (CEPA) obtained in Example 1 was added thereto, and while stirring with a homomixer, the skim milk powder was added to 16 parts of water heated to 70 ° C.
After slowly adding and mixing a solution in which 5 parts and 1 part of salt were dissolved, quenching plasticization was performed to obtain margarine (a conjugated long-chain highly unsaturated fatty acid content of 4.0% by weight) of the present invention.
【００３２】[0032]
【発明の効果】本発明の中性脂肪低減剤は、優れた中性
脂肪低減作用を有し、且つ安全性が高く副作用の少ない
脂肪酸又はその誘導体を有効成分として含有するもので
ある。The neutral fat reducing agent of the present invention has an excellent action of reducing neutral fat, and contains a fatty acid or a derivative thereof having high safety and few side effects as an active ingredient.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ａ６１Ｐ 3/06 Ａ６１Ｐ 3/06 (72)発明者 東海林 義和 東京都荒川区東尾久７丁目２番35号 旭電 化工業株式会社内 (72)発明者 藤本 健四郎 宮城県仙台市泉区桂二丁目３番地の13 Ｆターム(参考） 4B018 LB01 LB07 LB09 LE05 MD10 MD11 MD12 ME04 MF10 4C206 AA01 AA02 DA04 DA05 DB07 DB09 DB43 DB45 DB47 MA01 MA04 MA72 NA14 ZC33 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) A61P 3/06 A61P 3/06 (72) Inventor Yoshikazu Tokaibayashi 7-35 Higashiogu, Arakawa-ku, Tokyo Asahi Denki Kogyo Co., Ltd. (72) Inventor Kenshiro Fujimoto 13F term at 2-3-3 Katsura, Izumi-ku, Sendai, Miyagi Prefecture 4B018 LB01 LB07 LB09 LE05 MD10 MD11 MD12 ME04 MF10 4C206 AA01 AA02 DA04 DA05 DB07 DB09 DB43 DB45 DB47 MA01 MA04 MA72 NA14 ZC33
Claims (6)
脂肪酸、あるいは該脂肪酸の、エステルもしくは金属塩
又はその他の薬理学上許容される形態物を有効成分とす
る血清及び肝臓中の中性脂肪低減剤。1. Neutral serum and liver containing a fatty acid having 20 or more carbon atoms having a conjugated double bond, or an ester or metal salt or other pharmacologically acceptable form of the fatty acid as an active ingredient. Fat reducing agent.
役ジエンを４０〜７０％及びトリエン以上の共役ポリエ
ンを６０〜３０％含むものである請求項１記載の中性脂
肪低減剤。2. The neutral fat reducing agent according to claim 1, wherein the fatty acid contains 40 to 70% of a conjugated diene and 60 to 30% of a conjugated polyene of at least triene in all conjugated double bonds.
エイコサペンタエン酸、共役ドコサヘキサエン酸、共役
ドコサペンタエン酸及びα−エレオステアリン酸からな
る群から選ばれた１種又は２種以上の脂肪酸である請求
項１又は２記載の中性脂肪低減剤。3. The fatty acid is one or more fatty acids selected from the group consisting of conjugated arachidonic acid, conjugated eicosapentaenoic acid, conjugated docosahexaenoic acid, conjugated docosapentaenoic acid and α-eleostearic acid. The neutral fat reducing agent according to claim 1 or 2.
と、炭素数１〜１０のアルコール、エチレングリコー
ル、プロピレングリコール及びグリセリンからなる群か
ら選ばれた１種又は２種以上のアルコール類とのエステ
ルである請求項１〜３の何れかに記載の中性脂肪低減
剤。4. The ester of the fatty acid is an ester of the fatty acid with one or more alcohols selected from the group consisting of alcohols having 1 to 10 carbon atoms, ethylene glycol, propylene glycol and glycerin. The neutral fat reducing agent according to any one of claims 1 to 3.
カリウム塩、カルシウム塩、亜鉛塩及びマグネシウム塩
からなる群から選ばれた１種又は２種以上の塩である請
求項１〜３の何れかに記載の中性脂肪低減剤。5. The metal salt of the fatty acid is a sodium salt,
The neutral fat reducing agent according to any one of claims 1 to 3, which is one or more salts selected from the group consisting of potassium salts, calcium salts, zinc salts and magnesium salts.
低減剤を含有する飲食品。6. A food or drink comprising the neutral fat reducing agent according to any one of claims 1 to 5.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001061472A JP2002265360A (en) | 2001-03-06 | 2001-03-06 | Neutral fat-reducing agent |
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|---|---|
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Family
ID=18920760
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107970232A (en) * | 2016-10-21 | 2018-05-01 | 玛鲁哈日鲁株式会社 | Application of the composition and n-3 systems unrighted acid of the unrighted acid of system containing n-3 in the manufacture of said composition |
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| WO2000064854A1 (en) * | 1999-04-27 | 2000-11-02 | Kabushiki Kaisha Yakult Honsha | Conjugated fatty acid esters |
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| JP2001505579A (en) * | 1996-12-04 | 2001-04-24 | ウィスコンシン アラムニ リサーチ ファンデーション | Method for controlling body fat and / or body weight of animal and pharmaceutical composition used therefor |
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2001
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| JP2001505579A (en) * | 1996-12-04 | 2001-04-24 | ウィスコンシン アラムニ リサーチ ファンデーション | Method for controlling body fat and / or body weight of animal and pharmaceutical composition used therefor |
| WO1998043497A2 (en) * | 1997-03-27 | 1998-10-08 | The Procter & Gamble Company | Oral compositions having enhanced mouthfeel |
| JP2000355538A (en) * | 1999-04-15 | 2000-12-26 | Kanegafuchi Chem Ind Co Ltd | Receptor agonist responsive to peroxisome activator |
| WO2000064854A1 (en) * | 1999-04-27 | 2000-11-02 | Kabushiki Kaisha Yakult Honsha | Conjugated fatty acid esters |
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| CN107970232A (en) * | 2016-10-21 | 2018-05-01 | 玛鲁哈日鲁株式会社 | Application of the composition and n-3 systems unrighted acid of the unrighted acid of system containing n-3 in the manufacture of said composition |
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