JP3098560B2 - Weight gain inhibitor - Google Patents
Weight gain inhibitorInfo
- Publication number
- JP3098560B2 JP3098560B2 JP03064840A JP6484091A JP3098560B2 JP 3098560 B2 JP3098560 B2 JP 3098560B2 JP 03064840 A JP03064840 A JP 03064840A JP 6484091 A JP6484091 A JP 6484091A JP 3098560 B2 JP3098560 B2 JP 3098560B2
- Authority
- JP
- Japan
- Prior art keywords
- diglyceride
- weight gain
- acid
- lipase
- fatty acid
- 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.)
- Expired - Lifetime
Links
Description
【０００１】[0001]
【産業上の利用分野】本発明は体重増加抑制剤に関し、
更に詳細には脂質の過剰摂取による肥満を防止し、体重
の増加を抑制する薬剤に関する。FIELD OF THE INVENTION The present invention relates to a weight gain inhibitor,
More specifically, the present invention relates to a drug that prevents obesity due to excessive intake of lipids and suppresses weight gain.
【０００２】[0002]
【従来の技術】近年、食生活の変化に伴ない肥満症が増
加しつつある。肥満症は、心機能の低下、血圧の上昇、
動脈硬化の発生など種々の疾患の危険因子となる。かか
る肥満症の治療の基本は、食餌療法と運動である。しか
し、食餌療法は、カロリー計算が繁雑であり、また管理
の困難さから必ずしも良好な効果を得難い。一方、運動
量の増加は、効果に充分にでないという問題がある。2. Description of the Related Art In recent years, obesity has been increasing with changes in eating habits. Obesity is associated with decreased heart function, increased blood pressure,
It is a risk factor for various diseases such as the development of arteriosclerosis. The basis for the treatment of such obesity is diet and exercise. However, calorie calculation is complicated in diet, and it is not always possible to obtain a favorable effect due to difficulty in management. On the other hand, there is a problem that the increase in the amount of exercise is not sufficient for the effect.
【０００３】[0003]
【発明が解決しようとする課題】従って、食餌量を低下
させることなく体重の増加を抑制できる肥満防止剤の開
発が望まれていた。Accordingly, it has been desired to develop an anti-obesity agent capable of suppressing weight gain without reducing the amount of food.
【０００４】[0004]
【課題を解決するための手段】そこで、本発明者らは上
記課題を解決すべく種々検討した結果、トリグリセリド
の代わりにジグリセリドを含有する食餌を摂取すれば食
欲を低下させることなく、体重を低下させることができ
ることを見出し、本発明を完成した。The inventors of the present invention have conducted various studies to solve the above-mentioned problems. As a result, the ingestion of a diet containing diglyceride in place of triglyceride results in a decrease in weight without reducing appetite. The inventors have found that the present invention can be performed, and completed the present invention.
【０００５】すなわち、本発明は、下記の（１）式で表
わされるジグリセリドを有効成分とする体重増加抑制剤
を提供するものである。[0005] That is, the present invention provides a weight gain inhibitor comprising diglyceride represented by the following formula (1) as an active ingredient.
【０００６】本発明の体重増加抑制剤に用いられるジグ
リセリドは次の一般式（１）で表わされる。The diglyceride used in the weight gain inhibitor of the present invention is represented by the following general formula (1).
【０００７】[0007]
【化２】 Embedded image
【０００８】〔式中、Ｒ1、Ｒ2及びＲ3のうち２個はオ
レイン酸、リノール酸、リノレン酸、エイコサペンタエ
ン酸及びドコサヘキサエン酸から選ばれるアシル基を示
し、残余は水素原子を示す〕[Wherein, two of R 1 , R 2 and R 3 represent an acyl group selected from oleic acid, linoleic acid, linolenic acid, eicosapentaenoic acid and docosahexaenoic acid, and the remainder represents hydrogen atoms]
【０００９】かかるジグリセリドの製造法は、特に制限
されないが、例えば油脂とグリセリンの混合物をアルカ
リ金属及び／又はアルカリ土類金属の水酸化物の存在下
でエステル交換反応させるか、あるいは脂肪酸又は脂肪
酸エステルとグリセリンとの混合物にリパーゼを作用さ
せてエステル化反応を行なうことにより製造される。エ
ステル交換反応の具体例を挙げれば、リノール酸高含有
トリグリセリド 100部とリノレン酸高含有トリグリセリ
ド 100部との混合物に精製グリセリン30〜100部（好ま
しくは約50部）を配合し、触媒としてCa(OH)2 を 0.2部
添加し、窒素気流減圧下で 230℃、30分間攪拌を続けて
ランダムエステル交換反応を行う。冷却後脱グリセリン
し、薄膜式分子蒸留にてモノグリセリドを除去する。蒸
留残渣物として濃度85％のジグリセリドを得る。本製造
で用いるリノール酸高含有トリグリセリドとしてサフラ
ワー油、大豆油、トウモロコシ油等が挙げられるが、特
にサフラワー油が好ましい。またリノレン酸高含有トリ
グリセリドとしてアマニ油、シソ油、トウハゼ精油、エ
ノ油等が挙げられるが、特にアマニ油が好ましい。The method for producing such a diglyceride is not particularly limited. For example, a mixture of a fat or oil and glycerin is subjected to a transesterification reaction in the presence of a hydroxide of an alkali metal and / or an alkaline earth metal, or a mixture of a fatty acid and a fatty acid ester. It is produced by reacting a mixture of glycerin and glycerin with lipase to carry out an esterification reaction. As a specific example of the transesterification reaction, 30 to 100 parts (preferably about 50 parts) of purified glycerin is mixed with a mixture of 100 parts of linoleic acid-rich triglyceride and 100 parts of linolenic acid-rich triglyceride. OH) 2 is added, and the mixture is stirred at 230 ° C. for 30 minutes under reduced pressure of a nitrogen stream to perform a random transesterification reaction. After cooling, deglycerin is removed, and monoglyceride is removed by thin-film molecular distillation. A diglyceride having a concentration of 85% is obtained as a distillation residue. Examples of the linoleic acid-rich triglyceride used in the present production include safflower oil, soybean oil, corn oil, and the like. Safflower oil is particularly preferred. Linolenic acid-rich triglycerides include linseed oil, perilla oil, spruce essential oil, eno oil and the like, with linseed oil being particularly preferred.
【００１０】また、リパーゼによるエステル化反応の具
体例を挙げれば、グリセリン１モルに対し脂肪酸又は脂
肪酸エステル 1.5モル以上を添加した混合物に、リパー
ゼを脂肪酸又は脂肪酸エステル１ｇに対し 200〜1000un
its 添加し、40℃で21時間攪拌を続けてエステル化反応
を行なう。反応終了物よりリパーゼをろ別後、未反応脂
肪酸又は脂肪酸エステル及びモノグリセリドを分子蒸留
にて除去することにより、ジグリセリドを得る。使用す
る脂肪酸は、目的とするジグリセリドに応じて選択すれ
ばよい。また、脂肪酸エステルとしては、炭素数１〜３
の低級アルコール類とのエステルが好ましい。ここで炭
素数１〜３の低級アルコールとしては、例えばメタノー
ル、エタノール、プロパノール、イソプロパノールなど
が挙げられる。これらの脂肪酸又は脂肪酸エステルは単
独又は２種以上を混合して用いることができる。また、
リパーゼとしては、固定化又は菌体内１，３−位選択的
リパーゼが挙げられる。固定化１，３−位選択的リパー
ゼは１，３−位選択的リパーゼを公知の方法で固定化す
ることにより得られる。固定化のための公知の方法は、
例えば「固定化酵素」千畑一郎編集、講談社刊、９〜85
頁及び「固定化生体触媒」千畑一郎編、講談社刊、12〜
101 頁に記載されているが、イオン交換樹脂により固定
する方法が好ましいものとして例示される。固定化に用
いられる１，３−位選択的リパーゼとしては、リゾプス
（Rhizopus）属、アスペルギルス（Aspergillus）属、
ムコール（Mucor）属等の微生物由来のリパーゼ、膵臓
リパーゼ等がある。例えばリゾプス・デレマー（Rhizop
us delemar）、リゾプス・ジャポニカス（Rhizopus jap
onicus）、リゾプス・ニベウス（Rhizopus niveus）、
アスペルギルス・ニガー（Aspergillus niger）、ムコ
ール・ジャパニカス（Mucorjavanicus）、ムコール・ミ
ーハイ（Mucor miehei）などを起源とするリパーゼを使
用することができる。市販の固定化１，３−位選択的リ
パーゼとしては、ノボ・インダストリーＡ．Ｓ．社製の
商品名「Lipozyme3A」がある。菌体内１，３−位選択的
リパーゼは、微生物菌体に１，３−位選択的リパーゼが
吸着又は結合したもので、市販品としては、大阪細菌研
究所製の商品名「オリパーゼ」がある。これらのうち、
イオン交換樹脂で固定化したリパーゼを用いるのが特に
好ましい。得られたジグリセリド粗生成物中のジグリセ
リド含量は、蒸留法又はケイ酸カラムクロマトグラフ法
等により増加させることができる。Further, as a specific example of the esterification reaction with lipase, a mixture of 1.5 mol or more of fatty acid or fatty acid ester with respect to 1 mol of glycerin, and adding lipase with 200 to 1000 unper gram of 1 g of fatty acid or fatty acid ester.
Add it and continue the stirring at 40 ° C for 21 hours to carry out the esterification reaction. After filtering off the lipase from the reaction product, unreacted fatty acids or fatty acid esters and monoglycerides are removed by molecular distillation to obtain diglycerides. The fatty acid used may be selected according to the desired diglyceride. In addition, as the fatty acid ester, it has 1 to 3 carbon atoms.
And esters with lower alcohols are preferred. Here, examples of the lower alcohol having 1 to 3 carbon atoms include methanol, ethanol, propanol, and isopropanol. These fatty acids or fatty acid esters can be used alone or in combination of two or more. Also,
Examples of the lipase include lipase which is immobilized or 1,3-position selective in a bacterial cell. The immobilized 1,3-position selective lipase can be obtained by immobilizing the 1,3-position selective lipase by a known method. Known methods for immobilization are:
For example, "Immobilized enzyme" edited by Ichiro Chibatake, published by Kodansha, 9-85
Page and "Immobilized Biocatalyst" edited by Ichiro Chibatake, published by Kodansha, 12-
As described on page 101, a method of fixing with an ion exchange resin is exemplified as a preferable method. Examples of the 1,3-position selective lipase used for immobilization include genus Rhizopus, genus Aspergillus,
Lipases derived from microorganisms such as Mucor, pancreatic lipase, and the like. For example, Rhizop delemar
us delemar), Rhizopus jap
onicus), Rhizopus niveus,
Lipases originating from Aspergillus niger, Mucorjavanicus, Mucor miehei and the like can be used. Commercially available immobilized 1,3-position selective lipases include Novo Industry A. S. There is a brand name "Lipozyme3A" made by the company. The intracellular 1,3-position selective lipase is obtained by adsorbing or binding a 1,3-position selective lipase to a microbial cell, and a commercially available product is "Olipase" manufactured by Osaka Bacteria Research Institute. . Of these,
It is particularly preferable to use a lipase immobilized with an ion exchange resin. The diglyceride content in the obtained diglyceride crude product can be increased by a distillation method or a silica column chromatography method.
【００１１】これらのジグセリドのラットにおける経口
急性毒性は10g/kg体重以上であり、安全性の高いもので
ある。[0011] The oral acute toxicity of these digserides in rats is 10 g / kg body weight or more, and is highly safe.
【００１２】本発明の体重増加抑制剤は、経口、非経口
の何れの方法によっても投与することができ、経口投与
用の剤型としては、例えば錠剤、カプセル剤、散剤、顆
粒剤及びシロップ剤等が挙げられ、非経口投与用の剤型
としては注射剤、経腸用製剤等が挙げられる。これらの
調製には通常の賦形剤、崩壊剤、結合剤、滑沢剤、色
素、希釈剤などが用いられる。The weight gain inhibitor of the present invention can be administered by any of oral and parenteral methods. Examples of dosage forms for oral administration include tablets, capsules, powders, granules and syrups. And dosage forms for parenteral administration include injections, enteral preparations and the like. For these preparations, ordinary excipients, disintegrants, binders, lubricants, pigments, diluents and the like are used.
【００１３】賦形剤としてはブドウ糖、乳糖などが、崩
壊剤としてはデンプン、アルギン酸ナトリウムなどが、
滑沢剤としてはステアリン酸マグネシウム、硫酸パラフ
ィン、タルクなどが、結合剤としてはジメチルセルロー
ス、ゼラチン、ポリビニルピロリドンなどが用いられ
る。投与量は通常成人においてジグリセリドとして１日
１ｇ〜70ｇであるが、年齢、症状等により増減すること
ができる。なお、好ましい投与形態は通常の食事への添
加であり、食事成分中の脂質の50重量％以上をジグリセ
リドに置き換えるのが好ましい。Excipients include glucose and lactose, and disintegrants include starch and sodium alginate.
Magnesium stearate, paraffin sulfate, talc and the like are used as lubricants, and dimethyl cellulose, gelatin, polyvinyl pyrrolidone and the like are used as binders. The dosage is usually 1 g to 70 g per day as diglyceride in adults, but can be increased or decreased depending on age, symptoms and the like. In addition, a preferable administration form is addition to a normal meal, and it is preferable to replace 50% by weight or more of the lipid in the meal component with diglyceride.
【００１４】[0014]
【実施例】次に実施例を挙げて本発明を更に説明する
が、本発明はこれに限定されるものではない。Next, the present invention will be further described with reference to examples, but the present invention is not limited to these examples.
【００１５】参考例１ ジグリセリドの製造： なたね油（ヨウ素価 168）375gにグリセリン125gを配合
し、全系に対して0.1重量％の水酸化カルシウムを添加
して、窒素雰囲気下、 230℃で30分間攪拌を続けてラン
ダムエステル交換反応を行なった。冷却後、反応物を分
液ロートに移し分層後、下層を除去した。更に10％クエ
ン酸水溶液 500ml加えて攪拌し、放置分離後、上層部を
脱水ろ過し、粗なたね油脂肪酸組成ジグリセリドを得
た。更に粗なたね油脂肪酸組成ジグリセリドを 190℃、
0.01mmHgの条件下で薄膜式分子蒸留器に通して、本発明
に適するジグリセリドを含有する反応生成物を165g得
た。得られた反応生成物の脂肪酸組成及び含有分子種を
表１及び表２にそれぞれ示す。なお、これらの表中には
トリグリセリドとしてなたね油についての分析結果も併
せて示す。Reference Example 1 Production of diglyceride: 375 g of rapeseed oil (iodine value: 168) was mixed with 125 g of glycerin, 0.1% by weight of calcium hydroxide was added to the whole system, and the mixture was heated at 230 ° C. for 30 minutes in a nitrogen atmosphere. Stirring was continued to perform a random transesterification reaction. After cooling, the reaction product was transferred to a separating funnel, and after separating, the lower layer was removed. Further, 500 ml of a 10% aqueous citric acid solution was added thereto, followed by stirring. After standing and separating, the upper layer was subjected to dehydration filtration to obtain a crude diglyceride of rapeseed oil fatty acid composition. Furthermore, the crude glycerol oil fatty acid composition at 190 ° C
The solution was passed through a thin film molecular still under the condition of 0.01 mmHg to obtain 165 g of a reaction product containing a diglyceride suitable for the present invention. Tables 1 and 2 show the fatty acid composition and molecular species contained in the obtained reaction product. In addition, in these tables, the analysis results of rapeseed oil as triglycerides are also shown.
【００１６】[0016]
【表１】 [Table 1]
【００１７】[0017]
【表２】 [Table 2]
【００１８】実施例１ （実験方法）表３の組成の食餌を雄性ddY マウスに100
日間投与し、体重変動を追跡した。Example 1 (Experimental method) A male ddY mouse was fed 100% of a diet having the composition shown in Table 3.
Dosing for one day and body weight changes were followed.
【００１９】[0019]
【表３】 [Table 3]
【００２０】（実験結果）得られた結果を表４に示す。(Experimental results) Table 4 shows the obtained results.
【００２１】[0021]
【表４】 [Table 4]
【００２２】表４より、ジグリセリド食群は、トリグリ
セリド食群に比べ、飼料は多く摂取しているにもかかわ
らず、体重は低下しており、ジグリセリドに体重増加抑
制作用があることが明らかとなった。From Table 4, it is evident that the diglyceride diet group had a lower body weight than the triglyceride diet group despite the fact that they consumed more feed, and that diglyceride had an effect of suppressing weight gain. Was.
【００２３】実施例２ 軟カプセル剤皮組成 ゼラチン 70.0％ グリセリン 22.9％ パラオキシ安息香酸メチル 0.15％ パラオキシ安息香酸プロピル 0.15％ 水 適量 計 100％ 上記成分から成る軟カプセル剤皮の中に参考例１の製造
物 500mg（ジグリセリドとして 395mg含有）を常法によ
り充填し、軟カプセル剤を製造した。Example 2 Composition of Soft Capsule Skin Gelatin 70.0% Glycerin 22.9% Methyl paraoxybenzoate 0.15% Propyl paraoxybenzoate 0.15% Water qty 100% Preparation of Reference Example 1 in soft capsule skin composed of the above components 500 mg (containing 395 mg as diglyceride) was filled by a conventional method to produce a soft capsule.
【００２４】[0024]
【発明の効果】本発明によれば、ジグリセリドを投与す
ることにより、食欲を低下させることなく、体重の増加
を抑制することができる。According to the present invention, by administering diglyceride, an increase in body weight can be suppressed without lowering appetite.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 大辻 一也 栃木県宇都宮市平松本町466−14 (56)参考文献 特開 昭56−18939（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) A61K 31/231 A61K 31/232 A61P 3/04 ＣＡ（ＳＴＮ) ＥＭＢＡＳＥ（ＳＴＮ) ＭＥＤＬＩＮＥ（ＳＴＮ)──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Kazuya Otsuji 466-14 Hiramatsuhoncho, Utsunomiya-city, Tochigi Prefecture (56) References JP-A-56-18939 (JP, A) (58) Fields investigated (Int. . 7, DB name) A61K 31/231 A61K 31/232 A61P 3/04 CA (STN) EMBASE (STN) MEDLINE (STN)
Claims (1)
ノール酸、リノレン酸、エイコサペンタエン酸及びドコ
サヘキサエン酸から選ばれるアシル基を示し、残余は水
素原子を示す〕で表わされるジグリセリドを有効成分と
する体重増加抑制剤。1. The following general formula: [In the formula, two of R 1 , R 2 and R 3 represent an acyl group selected from oleic acid, linoleic acid, linolenic acid, eicosapentaenoic acid and docosahexaenoic acid, and the remainder represents a hydrogen atom.] A weight gain inhibitor containing diglyceride as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03064840A JP3098560B2 (en) | 1991-03-28 | 1991-03-28 | Weight gain inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03064840A JP3098560B2 (en) | 1991-03-28 | 1991-03-28 | Weight gain inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04300826A JPH04300826A (en) | 1992-10-23 |
| JP3098560B2 true JP3098560B2 (en) | 2000-10-16 |
Family
ID=13269832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP03064840A Expired - Lifetime JP3098560B2 (en) | 1991-03-28 | 1991-03-28 | Weight gain inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3098560B2 (en) |
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1991
- 1991-03-28 JP JP03064840A patent/JP3098560B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005060954A1 (en) * | 2003-12-19 | 2005-07-07 | Pronova Biocare As | Use of a fatty acid composition comprising at least one of epa and dha or any combinations thereof |
| US9282760B2 (en) | 2003-12-19 | 2016-03-15 | Pronova Biopharma Norge As | Use of a fatty acid composition comprising at least one of EPA and DHA or any combinations thereof |
| KR101814697B1 (en) | 2014-08-18 | 2018-01-03 | 주식회사 후레씨네코리아 | Tunnel box structure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04300826A (en) | 1992-10-23 |
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