JP2731948B2 - New oligosaccharides and their production and use - Google Patents
New oligosaccharides and their production and useInfo
- Publication number
- JP2731948B2 JP2731948B2 JP17160889A JP17160889A JP2731948B2 JP 2731948 B2 JP2731948 B2 JP 2731948B2 JP 17160889 A JP17160889 A JP 17160889A JP 17160889 A JP17160889 A JP 17160889A JP 2731948 B2 JP2731948 B2 JP 2731948B2
- Authority
- JP
- Japan
- Prior art keywords
- oligosaccharide
- lactulose
- present
- galactopyranosyl
- bifidobacteria
- 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.)
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- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、生体内におけるビフィズス菌に対して優れ
た増殖作用を有し、また、食物繊維、乳糖ならばにラク
チュロースと併用して摂取した場合、顕著な便秘改善作
用を示す新規なオリゴ糖とその製造法及び利用に関す
る。The present invention has an excellent proliferating action on bifidobacteria in a living body, and, in addition to dietary fiber, lactose, when taken in combination with lactulose, The present invention relates to a novel oligosaccharide exhibiting a remarkable constipation-ameliorating effect, and a method for producing and using the same.
従来の技術的背景 近年、生体内における有用菌として知られているビフ
ィズス菌の増殖を促進する物質（以下ビフィズス菌増殖
因子と称する）について多くの研究がなされており、そ
の増殖因子としてオリゴ糖が注目されている。2. Description of the Related Art In recent years, much research has been conducted on substances that promote the growth of bifidobacteria (hereinafter referred to as bifidobacterium growth factors), which are known as useful bacteria in vivo, and oligosaccharides are used as growth factors. Attention has been paid.
このようなオリゴ糖としてガラクトシルラクチュロー
スの増殖活性が報告されており、その製造法として、ラ
クチュロースにβ−ガラクトシダーゼを反応させてガラ
クトース転移反応を行わせる方法が提案されている特開
昭63-94987）。すなわち、この方法によると、下記式で
表わされるオリゴ糖が得られる。The growth activity of galactosyl lactulose has been reported as such an oligosaccharide, and a method for producing galactose transfer reaction by reacting lactulose with β-galactosidase has been proposed as a method for producing the oligosaccharide (JP-A-63-94987). . That is, according to this method, an oligosaccharide represented by the following formula is obtained.
β−Ｄ−ガラクトピラノシル−（１→６）−β−Ｄ−ガ
ラクトピラノシル−（１→４）−Ｄ−フラクトース 本発明者は、ビフィズス菌増殖作用を有するオリゴ糖
について検討した結果、ラクチュロースにβ−グルコシ
ダーゼを作用させることにより、上記増殖作用に加えて
便秘改善にも利用し得る新規オリゴ糖を見出し、本発明
をなすに至つた。β-D-galactopyranosyl- (1 → 6) -β-D-galactopyranosyl- (1 → 4) -D-fructose The present inventors have studied the results of oligosaccharides having a bifidobacterial growth activity. By making β-glucosidase act on lactulose, a novel oligosaccharide that can be used for improving constipation in addition to the above proliferating action was found, and the present invention was accomplished.
発明が解決しようとする課題 したがつて、本発明は、ビフィズス菌増殖作用に加え
てさらに便秘改善作用も有する新規オリゴ糖とその製造
法、さらにはこれらの作用を利用したビフィズス菌増殖
促進組成物及び便秘改善組成物を提供することを課題と
する。Accordingly, the present invention provides a novel oligosaccharide having a constipation-improving effect in addition to a bifidobacterium-proliferating effect, a method for producing the same, and a composition for promoting bifidobacterial growth utilizing these effects. And to provide a constipation improving composition.
課題を解決するための手段 本発明に係るオリゴ糖は、下記の式（Ｉ）及び（II）
で表わされる。Means for Solving the Problems The oligosaccharide according to the present invention has the following formulas (I) and (II)
Is represented by
Ｏ−β−Ｄ−ガラクトピラノシル−（１→３）−Ｏ−β
−Ｄ−ガラクトピラノシル−（１→４）−Ｄ−フラクト
ース（Ｉ） Ｏ−β−Ｄ−ガラクトピラノシル−（１→３）−Ｏ−β
−Ｄ−ガラクトピラノシル−（１→３）−Ｏ−β−Ｄ−
ガラクトピラノシル−（１→４）−Ｄ−フラクトース
（II） 次に、これらのオリゴ糖の物性値を示す。O-β-D-galactopyranosyl- (1 → 3) -O-β
-D-galactopyranosyl- (1 → 4) -D-fructose (I) O-β-D-galactopyranosyl- (1 → 3) -O-β
-D-galactopyranosyl- (1 → 3) -O-β-D-
Galactopyranosyl- (1 → 4) -D-fructose (II) Next, the physical properties of these oligosaccharides are shown.
（イ）分子量 式（Ｉ）……504 式（II）……666 （ロ）色調 乾燥、粉末化したものはいずれも白色を呈する。(B) Molecular weight Formula (I) 504 Formula (II) 666 (b) Color tone Both dried and powdered powders exhibit white color.
（ハ）酸性、塩基性及び中性の区別 いずれも中性を示す。(C) Distinguishing between acidic, basic, and neutral.
（ニ）溶解性 いずれも水に可溶性であるが、ベンゼン、クロロホル
ム、アセトンに難溶である。(D) Solubility Although all are soluble in water, they are poorly soluble in benzene, chloroform and acetone.
（ホ）呈色反応 硝酸銀反応 陰性（−） アンスロン硫酸反応 陽性（＋） ニンヒドリン反応 陰性（−） ビュレット反応 陰性（−） （ヘ）構成糖 本発明に係るオリゴ糖をそれぞれ0.5N-HC1により100
℃の温度で２時間加水分解して得られる生成糖のモル比
は、ガラクトース：フラクトース＝2:1であることから
２分子のガラクトースと１分子のフラクトースから成る
オリゴ糖と、ガラクトース：フラクトース＝3:1である
ことから３分子のガラクトースと１分子のフラクトース
から成るオリゴ糖であることが確認し得る。(E) Color reaction Silver nitrate reaction negative (-) Anthrone sulfate reaction positive (+) Ninhydrin reaction negative (-) Burette reaction negative (-) (f) Constituent sugars The oligosaccharides according to the present invention are each 100% by 0.5N-HC1.
Since the molar ratio of the produced sugar obtained by hydrolysis at a temperature of 2 ° C. for 2 hours is galactose: fructose = 2: 1, the oligosaccharide composed of two molecules of galactose and one molecule of fructose, and the galactose: fructose = 3 : 1, it can be confirmed that the oligosaccharide is composed of three molecules of galactose and one molecule of fructose.
（ト）構成糖及びオリゴ糖の結合態様 本発明に係るオリゴ糖をそれぞれ高速液体クロマトグ
ラフィー（HPLC）もしくは活性炭カラムクロマトグラフ
ィーにより分離精製した後、常法によりメチル化分析し
た結果、表１に示す結合態様が確認された。(G) Conjugation Mode of Constituent Sugar and Oligosaccharide The oligosaccharide according to the present invention was separated and purified by high performance liquid chromatography (HPLC) or activated carbon column chromatography, and then subjected to methylation analysis by a conventional method. The binding mode was confirmed.
（チ）β−配位 本発明に係るオリゴ糖は、β−ガラクトシダーゼの作
用によりガラクトースとフラクトースを生成することか
ら、β配置であることが確認し得る。 (H) β-coordination The oligosaccharide according to the present invention produces galactose and fructose by the action of β-galactosidase, so it can be confirmed that the oligosaccharide has the β configuration.
上記（イ）乃至（チ）に示した物性に鑑み、本発明に
係るオリゴ糖は前記式（Ｉ）及び（II）でそれぞれ表わ
されるものであると同定し得る。In view of the physical properties shown in (A) to (H) above, the oligosaccharide according to the present invention can be identified as those represented by the formulas (I) and (II), respectively.
次に、本発明に係るオリゴ糖の製造方法について説明
する。Next, the method for producing an oligosaccharide according to the present invention will be described.
本オリゴ糖は、ラクチュロースもしくはラクチュロー
ス含有物にβ−グルコシダーゼを作用させて、ラクチュ
ロース分子中のガラクトース残基に転移反応を行わせる
ことにより得ることができる。The present oligosaccharide can be obtained by reacting lactulose or a lactulose-containing substance with β-glucosidase to cause a galactose residue in the lactulose molecule to undergo a transfer reaction.
ここで出発物質として用いるラクチュロースもしくは
ラクチュロース含有物としては市販のラクチュロースま
たはラクチュロースシロップなどのラクチュロース含有
物を例示し得る。Here, as the lactulose or lactulose-containing material used as a starting material, commercially available lactulose or lactulose-containing materials such as lactulose syrup can be exemplified.
また、これらの出発物質に作用させるβ−グルコシダ
ーゼの起源について特に限定されるものではなく、スィ
ートアーモンドから得られた市販のβ−グルコシダーゼ
を例示できる。更に、高純度に精製された酵素ばかりで
なく、粗酵素を用いる事もできる。The source of β-glucosidase acting on these starting materials is not particularly limited, and commercially available β-glucosidase obtained from sweet almonds can be exemplified. Furthermore, not only a highly purified enzyme but also a crude enzyme can be used.
本発明では、出発物質としてラクチュロースもしくは
ラクチュロース含有物を５〜80重量％のラクチュロース
濃度に調整した溶液を用い、β−グルコシダーゼを１〜
1000単位/mlの酵素濃度で添加し、pH3〜８、10〜60℃の
温度で１時間乃至数日間、酵素反応を行うことが好まし
い。In the present invention, lactulose or a solution containing lactulose containing lactulose adjusted to a lactulose concentration of 5 to 80% by weight is used as a starting material, and β-glucosidase is used as a starting material.
It is preferable to add the enzyme at a concentration of 1000 units / ml and carry out the enzyme reaction at a temperature of pH 3 to 8 and 10 to 60 ° C for 1 hour to several days.
上記の酵素反応によりガラクトース転移反応が起り、
ガラクトシルラクチュロースが生成する。このようにし
て生成したガラクトシルラクチュロースは、90℃以上の
温度で１〜５分間加熱して酵素を失活させた後、通常起
われるオリゴ糖の分離、精製法に従って、効率よく調整
することができる。The galactose transfer reaction occurs by the above enzyme reaction,
Galactosyl lactulose is produced. The galactosyl lactulose thus produced can be efficiently adjusted according to a method for separating and purifying oligosaccharides which usually occurs after heating the enzyme at a temperature of 90 ° C. or higher for 1 to 5 minutes to inactivate the enzyme. .
上述のようにして得られるオリゴ糖は、既に言及した
ごとく、生体内のビフィズス菌に対して優れた増殖作用
を有し、また食物繊維や乳糖等と併用して摂取すると顕
著な便秘改善作用を示すので、ビフィズス菌増殖促進剤
及び便秘改善剤の有効成分として利用することが可能で
ある。As described above, the oligosaccharide obtained as described above has an excellent proliferative effect on bifidobacteria in a living body, and has a remarkable constipation improving effect when taken in combination with dietary fiber or lactose. As shown, it can be used as an active ingredient of a bifidobacterium growth promoter and a constipation improving agent.
次に、本発明に係るオリゴ糖のビフィズス菌に対する
増殖促進効果及び便秘改善効果を試験した結果を示す。Next, the results of testing the growth promoting effect and the constipation improving effect of the oligosaccharide according to the present invention on bifidobacteria are shown.
ビフィズス菌に対する増殖試験 試験方法 10匹を１群とするカニクイサルを供試動物として用
い、その各々に乳糖を５重量％添加した市販育児用粉乳
を５週間与えた後、本発明による糖アルコール（粉末形
態）を５重量％添加した育児用粉乳を更に３週間与え、
その間各サルの糞便を採取して便中のビフィズス菌の割
合を測定した。結果は添付の図面に示すとおりである。Bifidobacterium Proliferation Test Test Method Cynomolgus monkeys consisting of 10 animals as a group were used as test animals, and each of them was fed with a powdered milk for commercial use to which lactose was added at 5% by weight for 5 weeks. Form) was added to the milk powder for child care to which 5% by weight was added for another 3 weeks,
In the meantime, feces of each monkey were collected, and the proportion of bifidobacteria in the feces was measured. The results are as shown in the attached drawings.
図にみられるとおり、乳糖を添加して与えた期間中の
糞便中のビフィズス菌を割合に比べ、本発明によるオリ
ゴ糖を添加して与えた期間中の糞便中のビフィズス菌の
割合は著しく上昇している。As can be seen, the proportion of bifidobacteria in feces during the period in which the oligosaccharide was added was significantly increased compared to the ratio of bifidobacteria in the feces during the period in which lactose was added. doing.
すなわち、本発明によるオリゴ糖は生体内におけるビ
フィズス菌の増殖促進に極めて優れた効果を奏するもの
であり、また、人間の腸管内に生育する種々のビフィズ
ス菌、例えばビフィドバクテリウム・ロンガム、ビフィ
ドバクテリウム・ブリーベ、ビフィドバクテリウム・ビ
フィダム、ビフィドバクテリウム・アトレスセンティ
ス、ビフィドバクテリウム・インファンティス等の広範
囲な種類のビフィズス菌に対して高い増殖活性を示すこ
とが認められる。That is, the oligosaccharide according to the present invention has an extremely excellent effect on promoting the growth of bifidobacteria in a living body, and various kinds of bifidobacteria growing in the human intestinal tract, such as bifidobacterium longum, bifidobacterium longum, and the like. High growth activity against a wide variety of Bifidobacteria such as Fidobacterium brive, Bifidobacterium bifidum, Bifidobacterium atrescentis, and Bifidobacterium infantis .
したがって、本発明によるオリゴ糖は、粉乳、発酵乳
のごとき乳製品に配合したり、また、整腸剤のような薬
剤の成分として添加して用いることができる。Therefore, the oligosaccharide according to the present invention can be used in dairy products such as powdered milk and fermented milk, or can be used by adding as an ingredient of a drug such as an intestinal medicine.
因に、本発明によるオリゴ糖を２重量％添加した乳飲
料を調製し、これを健康成人30名に投与したところ、こ
れらの糞便中の全菌数に占めるビフィズス菌の比率の増
加は、乳糖を２重量％を添加した乳飲料を同様に投与し
た場合に比較して約２倍であることが認められた。By the way, when a milk beverage containing 2% by weight of the oligosaccharide according to the present invention was prepared and administered to 30 healthy adults, the ratio of bifidobacteria to the total number of bacteria in the feces was increased by Was about twice as much as when a milk beverage containing 2% by weight of was added in the same manner.
便秘改善試験 試験方法： 上記により得たオリゴ糖粉末を、日常的に便秘ぎみを
訴える健康な老人20名を４名づつの５つのグループに分
け、試験区No.1乃至No.5として、下記割合の量を投与し
た。試験区 オリゴ糖投与量（ｇ） No.1 ５ No.2 ４ No.3 ３ No.4（対照区） ２ No.5（対照区） ０ なお、各試験区ともに、上記量のオリゴ糖をそれぞれ
１日１回の割合で２週間投与して、投与前の２週間と投
与中の２週間における排便回数及び各排便毎の糞便の硬
さを官能的に評価した。Constipation improvement test Test method: The oligosaccharide powder obtained above was divided into five groups of four healthy elderly people who complain of constipation on a daily basis. Percentage doses were administered. Test group oligosaccharide dose (g) No.1 5 No.2 4 No.3 3 No.4 (control group) 2 No.5 (control group) 0 In each test group, use the above amount of oligosaccharide. Each dose was administered once a day for 2 weeks, and the number of defecations during the two weeks before the administration and during the two weeks during the administration, and the stool hardness of each defecation were sensorially evaluated.
結果は表２に示すとおりである。 The results are as shown in Table 2.
表２にみられるとおり、本発明によるオリゴ糖を投与
したグループでは3g以上の投与において排便回数の顕著
な増加と糞便の軟化が認められた。因に、対照区では排
便回数の増加及び糞便の軟化はほとんど認められなかっ
た。 As shown in Table 2, in the group to which the oligosaccharide according to the present invention was administered, a remarkable increase in the number of defecations and softening of feces were observed at a dose of 3 g or more. By the way, in the control group, increase in the number of defecations and softening of feces were hardly observed.
上述したとおり、本発明によるオリゴ糖の単独投与に
より顕著な便秘改善の効果が認められるようになる。そ
して、このような効果は、ヒト小腸微絨毛に存在するβ
−ガラクトシダーゼが大きいため、本発明によるオリゴ
糖は小腸で分解されずに大腸まで到達し、その結果、大
腸内の浸透圧が高くなって糞便を軟化して便秘を改善す
るものと推定される。As described above, the single administration of the oligosaccharide according to the present invention has a remarkable effect of improving constipation. And, such an effect is due to β β present in human small intestinal microvilli.
-Due to the large galactosidase, it is presumed that the oligosaccharide according to the present invention reaches the large intestine without being decomposed in the small intestine, and as a result, the osmotic pressure in the large intestine increases to soften feces and improve constipation.
発明の効果 以上述べたとおり、本発明に係るオリゴ糖は、ビフィ
ズス菌に対して優れた増殖促進効果を示し、さらに、便
秘改善効果についても排便回数の増加及び糞便の軟化を
もたらすという優れた効果を示す。Effect of the Invention As described above, the oligosaccharide according to the present invention exhibits an excellent growth-promoting effect on bifidobacteria, and also has an excellent effect of improving constipation, increasing the number of defecations and softening feces. Is shown.
以下に実施例を示して本発明によるオリゴ糖の調製に
ついて具体的に説明する。Hereinafter, the preparation of the oligosaccharide according to the present invention will be specifically described with reference to examples.
実施例 オリゴ糖の調製 ラクチュロース10kgを温水15kgに溶解した溶液にクエ
ン酸を加えてpHを5.0に調製したものに、β−グルコシ
ダーゼ50,000単位を加え、40℃の温度で10時間反応させ
た。得られた反応混合液を105℃の温度で２秒間加熱し
て酵素を失活させた。Example Preparation of Oligosaccharide To a solution prepared by dissolving 10 kg of lactulose in 15 kg of hot water and adjusting the pH to 5.0 by adding citric acid, 50,000 units of β-glucosidase was added and reacted at a temperature of 40 ° C. for 10 hours. The resulting reaction mixture was heated at 105 ° C. for 2 seconds to deactivate the enzyme.
次いで、この反応混合液2kgを活性炭−セライト（2:
1）のカラム（φ20cm×50cm）に通してラクチュロース
と転移オリゴ糖を吸着させた。次いで、15kgの水をカラ
ムに通して単糖と未吸着のラクチュロースを溶出し、除
去した後、５％エタノール20kgをカラムに通して吸着し
たラクチュロースを完全に溶出し、除去した。Then, 2 kg of the reaction mixture was charged with activated carbon-celite (2:
Lactulose and the transfer oligosaccharide were adsorbed through the column (1) (φ20 cm × 50 cm). Then, 15 kg of water was passed through the column to elute and remove the monosaccharide and unadsorbed lactulose, and then 20 kg of 5% ethanol was passed through the column to completely elute and remove the adsorbed lactulose.
次に、40％エタノール10kgをカラムに通して得られた
溶出液を減圧濃縮後、凍結乾燥してオリゴ糖95重量％以
上を含む粉末100gを得た。Next, the eluate obtained by passing 10 kg of 40% ethanol through the column was concentrated under reduced pressure, and lyophilized to obtain 100 g of a powder containing 95% by weight or more of oligosaccharide.
添付図は、本発明によるオリゴ糖のビフィズス菌に対す
る増殖試験をカニクイサルについて行った結果を示した
ものである。The attached figure shows the results of the growth test of the oligosaccharides of the present invention on bifidobacteria in cynomolgus monkeys.
Claims (5)
−Ｄ−ガラクトピラノシル−（１→４）−Ｄ−フラクト
ース（Ｉ）で表わされるオリゴ糖。(1) Formula (1) O-β-D-galactopyranosyl- (1 → 3) -O-β
An oligosaccharide represented by -D-galactopyranosyl- (1 → 4) -D-fructose (I).
−Ｄ−ガラクトピラノシル−（１→３）−Ｏ−β−Ｄ−
ガラクトピラノシル−（１→４）−Ｄ−フラクトース
（II）で表わされるオリゴ糖。2. Formula (II) O-β-D-galactopyranosyl- (1 → 3) -O-β
-D-galactopyranosyl- (1 → 3) -O-β-D-
An oligosaccharide represented by galactopyranosyl- (1 → 4) -D-fructose (II).
にβ−グルコシダーゼを作用させてガラクトース転移反
応を行わせることを特徴とする式（Ｉ）及び式（II）を
有するオリゴ糖を製造する方法。3. A method for producing an oligosaccharide having formulas (I) and (II), wherein β-glucosidase is allowed to act on lactulose or a lactulose-containing substance to cause a galactose transfer reaction.
ルラクチュロースから成るオリゴ糖を活性成分として含
有するビフィドバクテリウム菌の増殖促進組成物。4. A composition for promoting the growth of Bifidobacterium comprising an oligosaccharide comprising galactosyl lactulose having formulas (I) and (II) as an active ingredient.
ルラクチュロースから成るオリゴ糖を活性成分として含
有する便秘改善組成物。5. A composition for improving constipation, comprising an oligosaccharide comprising galactosyl lactulose having formulas (I) and (II) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17160889A JP2731948B2 (en) | 1989-07-03 | 1989-07-03 | New oligosaccharides and their production and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17160889A JP2731948B2 (en) | 1989-07-03 | 1989-07-03 | New oligosaccharides and their production and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0338593A JPH0338593A (en) | 1991-02-19 |
| JP2731948B2 true JP2731948B2 (en) | 1998-03-25 |
Family
ID=15926325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17160889A Expired - Fee Related JP2731948B2 (en) | 1989-07-03 | 1989-07-03 | New oligosaccharides and their production and use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2731948B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2561421B2 (en) * | 1993-05-17 | 1996-12-11 | 株式会社ウエスタン・アームス | Toy gun with automatic bullet feeding mechanism |
| JP2561429B2 (en) * | 1993-10-08 | 1996-12-11 | 株式会社ウエスタン・アームス | Toy gun with automatic bullet feeding mechanism |
| US10132591B2 (en) | 2016-08-29 | 2018-11-20 | Unit Solutions, Inc. | Non-lethal gas operated gun |
| US10801804B2 (en) | 2016-08-29 | 2020-10-13 | Unit Solutions, Inc. | Non-lethal gas operated gun |
-
1989
- 1989-07-03 JP JP17160889A patent/JP2731948B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0338593A (en) | 1991-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |