JPH02234667A - Proliferation promoter for lactobacillus bifidus and production thereof - Google Patents
Proliferation promoter for lactobacillus bifidus and production thereofInfo
- Publication number
- JPH02234667A JPH02234667A JP5494689A JP5494689A JPH02234667A JP H02234667 A JPH02234667 A JP H02234667A JP 5494689 A JP5494689 A JP 5494689A JP 5494689 A JP5494689 A JP 5494689A JP H02234667 A JPH02234667 A JP H02234667A
- Authority
- JP
- Japan
- Prior art keywords
- sorbitol
- glucose
- bifidobacteria
- glucosylsorbitol
- glucosyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 42
- 230000035755 proliferation Effects 0.000 title abstract description 6
- 229940068140 lactobacillus bifidus Drugs 0.000 title abstract 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 50
- 239000000600 sorbitol Substances 0.000 claims abstract description 50
- 235000001727 glucose Nutrition 0.000 claims abstract description 41
- 239000008103 glucose Substances 0.000 claims abstract description 39
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 38
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims abstract description 35
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 17
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- 239000003377 acid catalyst Substances 0.000 claims abstract description 14
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 10
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 150000002304 glucoses Chemical class 0.000 claims abstract 2
- 241000186000 Bifidobacterium Species 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 32
- 150000002016 disaccharides Chemical class 0.000 claims description 25
- 239000007952 growth promoter Substances 0.000 claims description 20
- 150000004043 trisaccharides Chemical class 0.000 claims description 14
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- 150000004044 tetrasaccharides Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
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- 150000007513 acids Chemical class 0.000 claims description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 8
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- 239000000047 product Substances 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- YXCQQSJTEBUHOD-RTPHMHGBSA-N (2R,3S,4R,5R)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]hexane-1,2,3,4,5,6-hexol Chemical compound [C@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO YXCQQSJTEBUHOD-RTPHMHGBSA-N 0.000 description 5
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Landscapes
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Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明はビフィズス菌に選択的に利用されて、これを生
育、増殖させるオリゴ糖からなる、ビフィズス菌増殖促
進剤及びその製造方法に関するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a bifidobacterium growth promoter comprising an oligosaccharide that is selectively utilized by bifidobacteria to grow and multiply them, and a method for producing the same. be.
更に詳しくは、ソルビトールにグルコースがβ1−1結
合、β1−6結合或いはβ1−4結合(本明細書ではこ
れらの結合を総称してβ結合という)している二糖を有
効成分とするビフィズス菌増殖促進剤、該二糖のグルコ
ース部分又はソルビトール部分に更にグルコースが1乃
至3個β結合している三糖、四糖、若しくは五糖を有効
成分とするビフィズス菌増殖促進剤、或いは該二糖類、
該三糖類、該四糖類及び該五糖類からなる群から2種類
以上の糖を選んでなる組成物を有効成分とするビフィズ
ス菌増殖促進剤、及び以上のビフィズス増殖促進剤の製
造方法に関する。More specifically, bifidobacterium containing as an active ingredient a disaccharide in which glucose is bonded to sorbitol by β1-1, β1-6 or β1-4 (herein, these bonds are collectively referred to as β-bonds). A growth promoter, a Bifidobacterium growth promoter whose active ingredient is a trisaccharide, tetrasaccharide, or pentasaccharide in which 1 to 3 glucose molecules are β-linked to the glucose moiety or sorbitol moiety of the disaccharide, or the disaccharide. ,
The present invention relates to a bifidobacteria growth promoter whose active ingredient is a composition comprising two or more types of saccharides selected from the group consisting of the trisaccharide, the tetrasaccharide, and the pentasaccharide, and a method for producing the above bifidobacterium growth promoter.
(従来の技術及び発明が解決しようとする課題)ビフィ
ズス菌(Bifidobacterium+に属する菌
種の総称)はヒトを含む咄乳動物や鳥類の腸内に生育し
ており、病原性菌の生育を抑制することによって騙内の
腐敗や有害物質の生成を抑制し、またビタミン等の有用
物質の産生を行う、等の働きを持つことが知られている
。その結果として、便秘や下痢、更には発癌を押さえる
効果があり、生体の健康を維持、増進するのに役立って
いるとされている。(Prior art and problems to be solved by the invention) Bifidobacteria (a general term for bacterial species belonging to Bifidobacterium+) grow in the intestines of mammals including humans and birds, and suppress the growth of pathogenic bacteria. It is known to have the function of suppressing the decay and production of harmful substances in the interior of the cabinet, as well as producing useful substances such as vitamins. As a result, it has the effect of suppressing constipation, diarrhea, and even cancer, and is said to be useful for maintaining and promoting the health of living organisms.
そこでビフィズス菌のみを選択的に増殖させてその生育
●増殖を促進し、以て腸の機能を良好に保つ物質(ビフ
ィズス菌増殖促進剤)の探索が続けられている。Therefore, the search for substances (bifidobacteria growth promoters) that selectively proliferate only bifidobacteria and promote their growth/proliferation, thereby maintaining good intestinal function, is ongoing.
そして糖の中でビフィズス菌増殖促進剤としての機能を
持つものには、ラフィノース、ラクチュロース、庶糖の
異性体であるバラチノース(特開昭57−91193)
、庶糖にフラクトースが1〜4分子結合したフラクト
オリゴ糖(特公昭59−53834)、グルコース分子
のα1−6結合を有する分岐オリゴ糖(特開昭61−2
2777)及び該分岐オリゴ糖の還元生成物(特開昭6
2−145020) 、イソマルトシルモノグルコース
の還元物(特公昭62−51585)等が知られている
。Sugars that function as bifidobacteria growth promoters include raffinose, lactulose, and baratinose, an isomer of sucrose (Japanese Patent Laid-Open No. 57-91193).
, fructooligosaccharides in which 1 to 4 fructose molecules are bonded to sucrose (Japanese Patent Publication No. 59-53834), branched oligosaccharides having α1-6 bonds of glucose molecules (Japanese Patent Publication No. 61-2
2777) and the reduction product of the branched oligosaccharide (Japanese Unexamined Patent Publication No. 6
2-145020), a reduced product of isomaltosyl monoglucose (Japanese Patent Publication No. 62-51585), and the like are known.
上記の糖は何れもビフィズス菌増殖促進作用に関しては
一応満足できるレベルにある。しかし製造方法について
見ると、工程が煩雑であったり、原料が高価なために製
造コストがかかるものが多かりた。また、従来の製造方
法でつくられた上記の糖の中で市販されている製品の中
には、原料由来の庶糖がかなりの量含まれているが、庶
糖は騙内の有害菌を増殖させるばかりではな《、虫歯や
肥満の原因にもなるものである。そこで従来の方法で製
造された製品を庶糖を含有しない純度の高い製品とする
ためには、更に精製工程を増やさなければならないが、
それによって製品のコストが更に高《なってしまうとい
う問題点があった。All of the above-mentioned sugars are at a somewhat satisfactory level in terms of their ability to promote the growth of Bifidobacterium. However, when looking at manufacturing methods, many of them are expensive due to complicated processes and expensive raw materials. Additionally, some commercially available sugar products made using conventional manufacturing methods contain a considerable amount of sucrose derived from raw materials, but sucrose can cause harmful bacteria to grow inside the sugar. Not only that, but it can also cause tooth decay and obesity. Therefore, in order to make products manufactured by conventional methods into highly pure products that do not contain sucrose, it is necessary to further increase the purification process.
This poses a problem in that the cost of the product becomes even higher.
このような状況の下で、庶糖を原料とせずに製造でき、
しかもコストが安価なビフィズス菌増殖促進剤とその製
造方法の開発が望まれていた。Under these circumstances, it is possible to produce sucrose without using sucrose as a raw material.
Furthermore, it has been desired to develop an inexpensive bifidobacteria growth promoter and a method for producing the same.
(課題を解決するための手段)
本発明者らはビフィズス菌増殖促進剤について鋭意研究
を行った結果、ソルビトールにグルコースがβ結合して
いる二糖、或いは該二糖のグルコース部分又はソルビト
ール部分に更にグルコースが1乃至3個β結合している
三糖乃至五糖が、ビフィズス菌を選択的に増殖させ、E
scherichiacoli, Clostridi
um perfringenss Bacteroid
esvulgatusなどの腸内の有害菌を増殖させな
いことを見い出した。(Means for Solving the Problems) As a result of intensive research into bifidobacteria growth promoters, the present inventors found that a disaccharide in which glucose is β-bonded to sorbitol, or a glucose moiety or a sorbitol moiety of the disaccharide, Furthermore, trisaccharides to pentasaccharides in which one to three glucose molecules are β-linked selectively proliferate Bifidobacterium, and E.
scherichiacoli, Clostridi
um perfringenss Bacteroid
It was discovered that harmful bacteria in the intestines such as S. esvulgatus do not proliferate.
ソルビトールにグルコースがα結合しているオリゴ糖(
以下α−グルコシルソルビトールという)がビフィズス
菌増殖促進活性を持っていることは先に述べたように特
開昭62〜145020や特公昭62−51686に記
載されているが、ソルビトールにグルコースがβ結合し
ている二糖、或0は該二糖のグルコース部分又はソルビ
トール部分に更にグルコースが1乃至3個β結合してい
る三糖乃至五糖がビフィズス菌を選択的に増殖する作用
を有することは、本発明者らが初めて見い出したもので
ある。An oligosaccharide in which glucose is α-linked to sorbitol (
As mentioned above, it is described in JP-A-62-145020 and JP-A-62-51686 that α-glucosyl sorbitol (hereinafter referred to as α-glucosyl sorbitol) has bifidobacterial growth promoting activity. It is believed that disaccharides, or trisaccharides and pentasaccharides in which 1 to 3 glucoses are β-linked to the glucose moiety or sorbitol moiety of the disaccharide, have the effect of selectively proliferating bifidobacteria. , was discovered for the first time by the present inventors.
また本発明者らは、原料として共に安価なグルコースと
ソルビトールとを、これも又安価な酸触媒の存在下で、
単に加熱処理を行うだけで上記の二糖乃至五糖を含む組
成物が得られることを見い出した。本出願の方法は酵素
を用いる製造方法と比較してコストが安く、製造工程も
簡便な製造方法である。The present inventors also used glucose and sorbitol, which are both cheap as raw materials, in the presence of an acid catalyst, which is also cheap.
It has been found that a composition containing the above disaccharides to pentasaccharides can be obtained simply by heat treatment. The method of the present application is a manufacturing method that is lower in cost and has a simpler manufacturing process than a manufacturing method using enzymes.
以下の本発明について更に詳しく記載する。The invention will be described in more detail below.
本発明の目的の一つは、ソルビトールにグルコースがβ
結合でつながった二糖、或いは該二糖のグルコース部分
又はソルビトール部分に更にグルコースが1乃至3個β
結合している三糖乃至五糖(以下β−グルコシルソルビ
トールという)を含有するビフィズス菌増殖促進剤に関
するものである。然して本発明でいうβ−グルコシルソ
ルビトールを二糖類と三糖類について例示すると、二糖
類ではβ−D−グルコシル−(1−1)−D−ソルビト
ール、β−D−グルコシル−(1−4)−D−ソルビ1
・−ル、β一D−グルコシル−(1−6)一D−ソルビ
トール、三糖類ではβ一D−グルコシル−( 1. −
6 )一β−D−グルコシル−(1−1)−D−ソル
ビl・−ル、β一D−グルコシル−(1−6)一β一D
−グルコシル−(1−4)一D−ソルビトール、β−D
−グルコシルー(1−6)一β−D−グルコシル−(1
−8)−D−ソルビトール等が挙げられる。One of the objects of the present invention is that sorbitol contains glucose
A disaccharide connected by a bond, or 1 to 3 glucose units β in the glucose moiety or sorbitol moiety of the disaccharide
The present invention relates to a bifidobacteria growth promoter containing bound trisaccharides to pentasaccharides (hereinafter referred to as β-glucosylsorbitol). However, to illustrate β-glucosyl sorbitol as used in the present invention with respect to disaccharides and trisaccharides, the disaccharides include β-D-glucosyl-(1-1)-D-sorbitol, β-D-glucosyl-(1-4)- D-Solbi 1
・-1.
6) -β-D-glucosyl-(1-1)-D-sorbyl, β-D-glucosyl-(1-6)-β-D
-Glucosyl-(1-4)-D-sorbitol, β-D
-glucosyl(1-6)-β-D-glucosyl-(1
-8)-D-sorbitol and the like.
本発明で使用されるβ−グルコシルソルビトールを使用
に供する形態は、製造して得られるシロップの状態のま
ま、或いは適宜の手段で該シロップを粉末化した上で用
いる等、自由に選択し得る。The form in which the β-glucosyl sorbitol used in the present invention is used can be freely selected, such as in the form of a syrup obtained by production, or after powdering the syrup by an appropriate means.
β−グルコシルソルビトールのビフィズス菌増殖促進効
果を利用する具体的な例としては、まずこれを単独でビ
フィズス菌増殖剤として供することが出来る。又、適当
な食品にこれを添加して、該食品を腸内のビフィズス菌
を増やす食品となさしめることが出来る。以上のように
して供する場合、生きたビフィズス菌と混合して用〜)
れば腸内ビフィズス菌を増加させる効果は一段と高くな
る。なお、β−グルコシルソルビトールは単独では庶糖
と比較して約1/8の甘味があり、本発明製造方法によ
り得られるα−グルコシルソルビトールとの混合物では
庶糖の約1/6の甘味を脊する。そのため甘味料として
、単独で或いは他の1千味剤と混合して使用することも
出来る。更にβ−グルコシルソルビトールは、叙上のビ
フィズス菌増殖促進作用を有する食品の製造や甘味料へ
の適用の他に、発酵工業や微生物学の研究におけるビフ
ィズス菌の増殖或いは大量生産用の培地成分として用い
られることも期待出来る。As a specific example of utilizing the bifidobacteria growth promoting effect of β-glucosylsorbitol, it can be used alone as a bifidobacteria growth agent. Furthermore, by adding it to a suitable food, the food can be made to increase the number of bifidobacteria in the intestine. When serving as above, mix with live bifidobacteria.)
If so, the effect of increasing intestinal bifidobacteria will be even higher. Note that β-glucosyl sorbitol alone has about 1/8 sweetness compared to sucrose, and when mixed with α-glucosyl sorbitol obtained by the production method of the present invention, it has about 1/6 the sweetness of sucrose. Therefore, it can be used as a sweetener alone or in combination with other flavoring agents. Furthermore, β-glucosyl sorbitol is used in the production of foods and sweeteners that have the above-mentioned effect of promoting the growth of bifidobacteria, as well as as a medium component for the growth or mass production of bifidobacteria in the fermentation industry and microbiological research. We can also expect it to be used.
β−グルコシルソルビトールはビフィズス菌増殖促進剤
としての使用に当たっては、必要の応じて単一の化合物
にまで精製して供してもよいし、以下に記載する製造例
等に従って得られる複数の種類のβ−グルコシルソルビ
トール化合物からなる混合物を精製せずにそのまま組成
物としても供してもよい。更に実施例1乃至5に記載さ
れている反応生成物のように、β−グルコンルソルビ1
・ールとα−グルコシルソルビトールとの混合組成物と
してもビフィズス菌増殖促進剤として使用され得る。When β-glucosylsorbitol is used as a bifidobacterial growth promoter, it may be purified into a single compound as necessary, or it can be purified into a single compound as required, or it can be used as a β-glucosyl sorbitol of multiple types obtained according to the production examples described below. - A mixture consisting of glucosylsorbitol compounds may be used as a composition without being purified. Furthermore, as the reaction products described in Examples 1 to 5, β-gluconrusorubi 1
・A mixed composition of alcohol and α-glucosyl sorbitol can also be used as a bifidobacteria growth promoter.
本発明に係るβ−グルコシルソルビトールを製造するに
は公知の方法を採ることが出来るが、後に示す表1から
も明らかなように、β−グルコシルソルビトールのビフ
ィズス菌増殖促進剤としての効果は製造方法によって何
等変わるものではなII1。腸内でビフィズス菌以外の
有害細菌をも増殖させ、虫歯や肥満の原因ともなる反応
基質由来のグルコースを反応生成物から除去するには、
活性炭素がβ−グルコシルソルビトール及びα−グルコ
シルソルビトールのようなオリゴ糖をグルコース及びソ
ルビトールのような単糖よりも強く吸着する性質(Na
kanishi, K. at al. :(+983
) Enz.Microbiol. Technol.
, 5, 115−120)を利用して、種々の製造方
法で得られた二糖乃至五糖を含む反応生成物を活性炭素
カラムに通し、吸着された糖類をエタノール水溶液等で
溶出させる工程を追加すればよい。Known methods can be used to produce β-glucosylsorbitol according to the present invention, but as is clear from Table 1 shown later, the effectiveness of β-glucosylsorbitol as a bifidobacteria growth promoter is determined by the manufacturing method. It doesn't change anything depending on II1. In order to remove glucose derived from the reaction substrate from the reaction product, which causes harmful bacteria other than Bifidobacterium to grow in the intestines and causes tooth decay and obesity,
The property of activated carbon to adsorb oligosaccharides such as β-glucosylsorbitol and α-glucosylsorbitol more strongly than monosaccharides such as glucose and sorbitol (Na
Kanishi, K. at al. :(+983
) Enz. Microbiol. Technol.
, 5, 115-120), the reaction products containing disaccharides to pentasaccharides obtained by various production methods are passed through an activated carbon column, and the adsorbed saccharides are eluted with an aqueous ethanol solution. Just add it.
以下の製造例では、反応生成物がα−グルコシルソルビ
トールを含まないように製造する方法として、グルコー
スとソルビトールとからなる混合水溶液にβ−グルコシ
ダーゼを作用させ、加水分解の逆反応により製造する方
法、及びソルビトールを構造の中に有していないβ結合
を有するオリゴ糖(本製造例ではセロオリゴ糖)を還元
する製造方法を示す。この他に、β結合を有するオリゴ
糖、例えばセロオリゴ糖からソルビトールへグリコシル
トランスフェラーゼを用いて糖を転移させる反応を利用
することによっても製造することができる。In the following production examples, as a method of producing the reaction product so that it does not contain α-glucosylsorbitol, a method of producing it by reacting β-glucosidase on a mixed aqueous solution consisting of glucose and sorbitol and performing a reverse reaction of hydrolysis; and a production method for reducing an oligosaccharide (cellooligosaccharide in this production example) having a β bond that does not have sorbitol in its structure. In addition, it can also be produced by utilizing a reaction in which sugar is transferred from an oligosaccharide having a β bond, such as a cellooligosaccharide, to sorbitol using a glycosyltransferase.
(製造例1:β−グルコシダーゼの利用による)グルコ
ース Igとソルビトール IEとを0,1M酢酸緩衝
液(pH 5.0) 0.5−に溶解し、アーモンド由
来のβ−グルコシダーゼ(シグマ社製)5mgcioo
ユニット)を加えて37℃に保ったまま2日間反応させ
た。加熱により酵素を失活させた後、蒸留水で希釈して
酵素を濾別除去し、得られた濾液をIIPLcにより分
析したところ、54%がβ−グル1〇一
コシルソルビトール組成物であった。このシロップ状の
反応生成物を活性炭素カラム(2cmφ×50am)に
吸着させ、蒸留水300+nQを通してカラムをよく洗
浄した。次いで200艷のlO%エタノール水溶液によ
り吸着物を溶出させ、エバボレーターにより濃縮したと
ころ、0.73gのシロップが得られた。(Production Example 1: By using β-glucosidase) Glucose Ig and sorbitol IE were dissolved in 0.1M acetate buffer (pH 5.0), and almond-derived β-glucosidase (manufactured by Sigma) was added. 5mgcioo
Unit) was added and the mixture was allowed to react for 2 days while being kept at 37°C. After inactivating the enzyme by heating, it was diluted with distilled water and the enzyme was removed by filtration, and the resulting filtrate was analyzed by IIPLc, and it was found that 54% was a β-glu 101 cosyl sorbitol composition. Ta. This syrupy reaction product was adsorbed onto an activated carbon column (2 cmφ x 50 am), and the column was thoroughly washed by passing 300+nQ of distilled water. Next, the adsorbed matter was eluted with 200 lO% aqueous ethanol solution and concentrated using an evaporator to obtain 0.73 g of syrup.
このシロップをHPLCで分析したところ、二糖類が6
5%、三糖類が23%、四糖類がlO%、五糖類が2%
からなるβ−グルコシルソルビトール組成物であった。When this syrup was analyzed by HPLC, it was found that 6 disaccharides were present.
5%, trisaccharides 23%, tetrasaccharides 10%, pentasaccharides 2%
It was a β-glucosyl sorbitol composition consisting of.
(製造例2: β結合を有するオリゴ糖の還元による)
ゲンチオビオース(構造はβ一D−グルコシル− (1
−6) 一D−グルコース)Igを蒸留水25ml+に
溶解させ、これにIgの水素化硼素ナトリウムを少量ず
つ添加した。次いで1時間攪拌し、その後2%酢酸50
−を少しずつ添加した。更に1時間攪拌した後、反応液
をエバボレーターによって濃縮した。該濃縮物を蒸留水
5−に溶解した後、■“型にしたダウケミカル社製のダ
ウエックス50W−X80カラム(2cmφX50 c
m)に通過させた。(Production Example 2: By reduction of oligosaccharides having β-bonds)
Gentiobiose (structure is β-D-glucosyl- (1
-6) Ig (1D-glucose) was dissolved in 25 ml+ of distilled water, and sodium borohydride of Ig was added little by little. It was then stirred for 1 hour, and then 2% acetic acid 50
- was added little by little. After further stirring for 1 hour, the reaction solution was concentrated using an evaporator. After dissolving the concentrate in distilled water, a
m).
+1−
更に得られた通過液をOH一型にした東京有機化学工業
社製のアンバーライトCG−400のカラム(2cIl
φ×50c■)を通過させた。該通過液をエバボレータ
ーにより濃縮した後、濃縮残渣を2艷の蒸留水に溶解し
、活性炭素力ラム(2cm+φX50cm)に吸着させ
た。蒸留水300m9をカラムに通すことにより活性炭
素カラムをよ《洗浄した後、lo%エタノール水溶液2
0Mで溶出させた。溶出液をエバボレーターで濃縮した
ところ、ほぼ純粋な350mgのβ一Dグルコシル−(
1−6)−D−ソルビトールを得た。+1- Furthermore, the obtained permeate was subjected to a column of Amberlite CG-400 manufactured by Tokyo Organic Chemical Industry Co., Ltd. (2 cIl
φ×50c■). After concentrating the permeate using an evaporator, the concentrated residue was dissolved in two bottles of distilled water and adsorbed on an activated carbon force ram (2 cm + φ x 50 cm). After thoroughly washing the activated carbon column by passing 300 m9 of distilled water through the column, a lo% ethanol aqueous solution 2
Eluted at 0M. When the eluate was concentrated using an evaporator, 350 mg of almost pure β-D glucosyl (
1-6)-D-Sorbitol was obtained.
次に本発明のもう一つの目的であるβ−グルコシルソル
ビトールの製造方法について述べる。本発明方法はグル
コースとソルビトールとを原料とし、酸触媒の存在下で
該原料混合水溶液を加熱することからなるβ−グルコシ
ルソルビトール組成物の製造方法である。この製造方法
を用いると、上に述べた酵素を触媒として用いる製造方
法と異なり、β−グルコシルソルビトールとα−グルコ
シルソルビトールとの混合物が生成されるが、β12一
ーグルコシルソルビトール及びα−グルコシルソルビト
ールは共に選択的なビフィズス菌増殖促進剤であるから
、混合物のままでビフィズス菌増殖促進剤として使用に
供することができる。Next, a method for producing β-glucosylsorbitol, which is another object of the present invention, will be described. The method of the present invention is a method for producing a β-glucosylsorbitol composition using glucose and sorbitol as raw materials and heating an aqueous solution of the raw material mixture in the presence of an acid catalyst. When this production method is used, unlike the production method using an enzyme as a catalyst, a mixture of β-glucosylsorbitol and α-glucosylsorbitol is produced, but β12-glucosylsorbitol and α-glucosylsorbitol are Since both are selective bifidobacteria growth promoters, the mixture can be used as a bifidobacterium growth promoter.
ここで酸触媒とは、塩酸や硫酸等の鉱酸、酢酸、クエン
酸、リンゴ酸、コハク酸等の有機酸、更にはH4型陽イ
オン交換樹脂をも包含するものである。Here, the acid catalyst includes mineral acids such as hydrochloric acid and sulfuric acid, organic acids such as acetic acid, citric acid, malic acid, and succinic acid, and even H4 type cation exchange resins.
鉱酸や有機酸を酸触媒として用いる場合は、グルコース
とソルビトールとの混合水溶液に添加する。When using a mineral acid or an organic acid as an acid catalyst, it is added to a mixed aqueous solution of glucose and sorbitol.
H4型陽イオン交換樹脂を酸触媒として用いる場合には
、鉱酸や有機酸を酸触媒として用いる場合と同様にグル
コースとソルビトールとの混合水溶液に添加するか、或
いは上記イオン交換樹脂をカラムに詰め、グルコースと
ソルビトールの混合水溶液を通過させる。次に加熱温度
について述べると、70℃以上であれば反応が進行し、
温度が高いほど反応速度は速くなるが、120℃を越え
ると反応生成物が着色し始め、150’Cを越えると着
色の度合が著しくなる。そのため70〜150℃が実質
的に適用し得る温度範囲であり、更に反応速度の向上と
商品としての見栄えの両者を勘案すれば85〜120℃
の範囲が好ましい。When using an H4 type cation exchange resin as an acid catalyst, it can be added to a mixed aqueous solution of glucose and sorbitol in the same way as when mineral acids or organic acids are used as acid catalysts, or the ion exchange resin can be packed in a column. , a mixed aqueous solution of glucose and sorbitol is passed through. Next, regarding the heating temperature, if it is 70°C or higher, the reaction will proceed;
The higher the temperature, the faster the reaction rate; however, when the temperature exceeds 120°C, the reaction product begins to be colored, and when the temperature exceeds 150'C, the degree of coloration becomes significant. Therefore, the practically applicable temperature range is 70 to 150℃, and 85 to 120℃ considering both the improvement of reaction rate and the appearance of the product.
A range of is preferred.
上記製造方法により得られた反応組成物から未反応のグ
ルコースやソルビトールを除去するには、製造例l及び
製造例2の中にも記載があるように、該反応組成物を活
性炭素カラムに通し、カラムに吸着された糖をエタノー
ル水溶液等で溶出すればよい。In order to remove unreacted glucose and sorbitol from the reaction composition obtained by the above production method, as described in Production Example 1 and Production Example 2, the reaction composition is passed through an activated carbon column. , the sugars adsorbed on the column may be eluted with an ethanol aqueous solution or the like.
(実施例)
以下に本発明を実施例として記載するが、本発明がこれ
らに限定されるものではないことは勿論である。なお、
製造方法に関する実施例において生成されるグルコシル
ソルビトールは、先にも記したように全てβ−グルコシ
ルソルビトールとα−グルコシルソルビトールとの混合
物であるので、該混合物を実施例中では単にグルコシル
ソルビトールと記載する。(Examples) The present invention will be described below as examples, but it goes without saying that the present invention is not limited to these examples. In addition,
As mentioned above, the glucosyl sorbitol produced in the examples regarding the production method is a mixture of β-glucosyl sorbitol and α-glucosyl sorbitol, so this mixture is simply referred to as glucosyl sorbitol in the examples. .
(実施例1:酸触媒として塩酸を用いた製造方法)10
0■gのグルコースと300mgのソルビトールとを蒸
留水に溶解して全量を0. 5m9とし、これにlOΔ
のl3
濃塩酸を加えて85゛Cに保ったままで3時間反応させ
た。反応終了後冷却し、O.lNのNaOHで反応液を
中和してンロップ状の反応生成物を得た。HPLCでこ
の反応生成物の組成を分析したところ、未反応のグルコ
ースとソルビトールが合わせて47.1%、二糖類のグ
ルコンルソルビトールが372%、三糖類のグルコシル
ソルビ1・−ルが15.7%であった。(Example 1: Production method using hydrochloric acid as an acid catalyst) 10
Dissolve 0 g of glucose and 300 mg of sorbitol in distilled water and adjust the total amount to 0.0 g. 5m9, and lOΔ
13 concentrated hydrochloric acid was added, and the mixture was allowed to react for 3 hours while maintaining the temperature at 85°C. After the reaction was completed, it was cooled and O. The reaction solution was neutralized with 1N NaOH to obtain a sloppy reaction product. When the composition of this reaction product was analyzed by HPLC, the total amount of unreacted glucose and sorbitol was 47.1%, the disaccharide gluconorbitol was 372%, and the trisaccharide glucosylsorbitol was 15.7%. %Met.
(実施例2:酸触媒としてクエン酸を用いた製造方法)
85℃に熱せられたオイルバスの中に浸された22の反
応容器に250−の蒸留水を入れ、この蒸留水を撹拌装
置で激しく撹拌しつつ、該反応容器内へ500gのグル
コースと500gのソルビトールを少量づつ交互に加え
ていった。グルコースとソルビトールの全量を加え終わ
った後にクエン酸20gを該反応容器内に入れ、更にオ
イルバスの温度を105℃に」二げた。そのままの状態
で40時間撹拌して反応を行わせた後、オイルバスの温
度を80℃に下げて0.8NのNaO}Iを加えて反応
生成物を中和した。(Example 2: Production method using citric acid as an acid catalyst) 250-g distilled water was put into 22 reaction vessels immersed in an oil bath heated to 85°C, and the distilled water was mixed with a stirring device. While stirring vigorously, 500 g of glucose and 500 g of sorbitol were alternately added in small portions into the reaction vessel. After adding all of the glucose and sorbitol, 20 g of citric acid was added to the reaction vessel, and the temperature of the oil bath was raised to 105°C. After stirring for 40 hours to carry out the reaction, the temperature of the oil bath was lowered to 80°C and 0.8N NaO}I was added to neutralize the reaction product.
オイルバスの温度を80℃に保ったまま500−の蒸留
=15−
水をこれに加えて希釈した。シロップ状の反応生成物を
取り出して冷却後、反応生成物の組成をHPLCにより
分析したところ、グルコースとソルビトールが合わせて
45.2%、二糖類のグルコシルソルビトールが38.
1%、三糖類のグルコシルソルビトールが16,7%で
あった。Distillation of 500- = 15- water was added to this to dilute it while keeping the temperature of the oil bath at 80°C. After taking out the syrup-like reaction product and cooling it, the composition of the reaction product was analyzed by HPLC, and it was found that the total content of glucose and sorbitol was 45.2%, and the disaccharide glucosylsorbitol was 38%.
1%, and the trisaccharide glucosylsorbitol was 16.7%.
上で得られた希釈後のシロップ状の反応生成物を1.5
艷取って、活性炭素力ラム(2cmφX50cm)に通
してこれに吸着させ、蒸留水500艷を通してカラムを
よく洗浄した後、20%エタノール水溶液500叔で吸
着した全糖を溶出させ、エバポレーターによって濃縮し
たところ、0.62gのシロップ状の組成物が得られた
(下の実施例5ではこの組成物を使用して実験を行った
)。この組成物をHPLCで分析したところ、グルコー
ス及びソルビトールは合わせても2%以下となっており
、二糖類のグルコシルソルビトールが64%、三糖類の
グルコシルソルビトールが34%であった。The syrup-like reaction product after dilution obtained above was diluted with 1.5
The column was taken out, passed through an activated carbon force column (2 cmφ x 50 cm), and adsorbed onto it.The column was thoroughly washed by passing 500 mm of distilled water through it, and then all the adsorbed sugars were eluted with 500 mm of a 20% ethanol aqueous solution, and concentrated using an evaporator. Thus, 0.62 g of syrupy composition was obtained (experiment was carried out using this composition in Example 5 below). When this composition was analyzed by HPLC, the total content of glucose and sorbitol was less than 2%, with the disaccharide glucosylsorbitol accounting for 64% and the trisaccharide glucosylsorbitol accounting for 34%.
(実施例3:酸触媒としてH1形陽イオン交換樹脂をバ
ッチ式に用いた製造方法)
85℃のオイルバスに浸漬させた容器に蒸留水250艷
を入れ、これを激しく撹拌しながらグルコース500g
とソルビトール500 gとを加えてこれらを溶解した
。この混合物水溶液に乾燥したH4型ダウエックス50
W−X8イオン交換樹脂(ダウケミカル社製)50gを
添加して、オイルバスの温度を105℃に上昇させてそ
のまま40時間攪拌しつつ反応させた。(Example 3: Manufacturing method using H1 type cation exchange resin as an acid catalyst in batch mode) 250 g of distilled water was put into a container immersed in an oil bath at 85° C., and while stirring vigorously, 500 g of glucose was added.
and 500 g of sorbitol were added to dissolve these. Dry H4 type Dowex 50 is added to this mixture aqueous solution.
50 g of W-X8 ion exchange resin (manufactured by Dow Chemical Company) was added, and the temperature of the oil bath was raised to 105° C., and the mixture was allowed to react with stirring for 40 hours.
反応終了後85℃までオイルバスを冷却し、蒸留水80
0艷を加えて希釈してから、反応物をフィルターを通過
させて上記イオン交換樹脂を除去した。After the reaction, cool the oil bath to 85°C and add distilled water to 85°C.
After diluting by adding 0.0 liters of water, the reaction mixture was passed through a filter to remove the ion exchange resin.
得られた濾液に蒸留水を加え、全量で29のシロップを
得た。Distilled water was added to the obtained filtrate to obtain a total of 29 syrups.
このシロップをHPLC及びIOOMHZ ”C NM
Rにより詳細に分析したところ、グルコースとソルビト
ールとがα1−1、α1−6、β1−1若しくはβ1−
6結合した二糖のグルコシルソルビトール及び該二糖の
グルコシルソルビトールに更にグルコースが結合した三
糖以上のグルコシルソルビトールが含まれていることが
判明した。二糖以上からなるグルコシルソルビトールの
糖全体に対する割合は59%であった。This syrup was analyzed by HPLC and IOOMHZ "C NM"
Detailed analysis by R revealed that glucose and sorbitol are α1-1, α1-6, β1-1 or β1-
It was found that glucosylsorbitol, which is a hexa-linked disaccharide, and glucosylsorbitol, which is a trisaccharide or more, in which glucose is further bonded to the disaccharide glucosylsorbitol, are contained. The ratio of glucosylsorbitol consisting of disaccharides or more to the total sugars was 59%.
(実施例4:酸触媒としてH4形陽イオン交換樹脂力ラ
ムを用いた製造方法)
グルコース5gとソルビトール5gとを蒸留水8艷に溶
解し、乾燥した3gのH4型ダウエックス50W−X8
イオン交換樹脂を詰めたカラム(2 c誼φX50c
m)に該水溶液をペリスクリックポンプにより約1載/
分の速度で連続循環を開始した。(Example 4: Production method using H4 type cation exchange resin power ram as acid catalyst) 5 g of glucose and 5 g of sorbitol were dissolved in 8 bottles of distilled water, and 3 g of H4 type DOWEX 50W-X8 was dried.
Column packed with ion exchange resin (2 cm φX50c
m) about 1 load of the aqueous solution using a peri-click pump.
Continuous circulation was started at a rate of 1 minute.
そのまま16時間循環を続けて反応を行わせた。上記カ
ラムは該水溶液を循環させている間はオイルバヌ(こ浸
漬して85℃に保っておいた。反応終了後、ボンブを止
めてカラムからシロップ状の循環液を取り出した。該シ
ロップ中の糖組成をl{PLOにより分析したところ、
グルコシルソルビトールは45%の割合で含まれていた
。更に該シロップを100Mtlz I3C NMRに
かけ、得られたスペクトルをより詳細に分析したところ
、グルコースとソルビトールとがα1−1、α1−6、
β1−1若しくはβ1−6結合した二糖からなるグルコ
シルソルビトール、及び該二糖からなるグルコシルソル
ビトール+8−
に更にグルコースが一つ以上結合した三糖以上のグルコ
シルソルビトールが含まれていることが判明した。The reaction was continued by continuing circulation for 16 hours. While the aqueous solution was being circulated, the column was immersed in oil and kept at 85°C. After the reaction was completed, the bomb was stopped and the circulating liquid in the form of syrup was taken out from the column. When the composition was analyzed by l{PLO,
Glucosylsorbitol was contained at a rate of 45%. Further, the syrup was subjected to 100 Mtlz I3C NMR, and the resulting spectrum was analyzed in more detail.
It was found that glucosyl sorbitol, which consists of a disaccharide with β1-1 or β1-6 bonds, and glucosyl sorbitol, which consists of glucosyl sorbitol +8-, which consists of the disaccharide and trisaccharide or more, in which one or more glucose is further bonded, are contained. .
(実施例5:グルコシルソルビトールの選択的なビフィ
ズス菌増殖促進作用)
用いた菌は、ビフィズス菌としてBif idobac
te−rium breve (理化学研究所保存株タ
イブSI;以下B. braveという)N Bif
idobacterium infantis(理化学
研究所保存株タイプS12 ;以下B.infanti
sという) 、Blfidobacterium bi
fidum (理化学研究所保存株aE319;以下B
. bifidumという)、Blfidobacte
rium longum (ATCC 1570
8; 以下B.longumという)を、ラクトバチ
ルス菌としてLactobacillus acido
phllus (JCM 1132:以下L.ac i
doph l Iusという)を、そして対照の腸内細
菌として、Eschelichia coli (JC
M 1649;以下E.coliという) N En
terococcus faecalis (ATCC
19433 ;以下Ent. faecalisとい
う) 、Bacte−roldes vulgatus
(JCM 5828;以下Bact.vulgat
usという)X Clostridium perf
ringens(JCM 3817;以下C. per
fringensという)であった。(Example 5: Selective action of glucosylsorbitol to promote growth of Bifidobacteria) The bacteria used were Bifidobacteria as Bifidobacteria.
te-rium breve (RIKEN preserved stock T. SI; hereinafter referred to as B. brave)
idobacterium infantis (RIKEN preserved strain type S12; hereinafter referred to as B. infantis)
), Blfidobacterium bi
fidum (RIKEN stock aE319; hereinafter B
.. bifidum), Blfidobacterium
rium longum (ATCC 1570
8; Below B. Lactobacillus acido (called Lactobacillus longum)
phllus (JCM 1132: hereafter L.ac i
doph l Ius) and Escherichia coli (JC
M 1649; hereinafter referred to as E. coli) N En
terococcus faecalis (ATCC
19433; hereinafter Ent. faecalis), Bacte-roldes vulgatus
(JCM 5828; hereafter Bact.vulgat
us)X Clostridium perf
ringens (JCM 3817; hereinafter referred to as C. per
It was called fringens).
培地は、ビフィズス菌及びラクトバチルス菌にはLB発
酵試験培地を、その他の菌にはPYFプロス(Pept
one yeast extract Fildes
solutionbroth)を用いた。培地の組成は
以下の通りである。The medium used was LB fermentation test medium for Bifidobacterium and Lactobacillus, and PYF Pros (Peptide) for other bacteria.
one yeast extract
solutionbroth) was used. The composition of the medium is as follows.
堕i鼠跋l亙1
Bacto−Liver (Difco)浸出液
1.000ntQProteose peptone
No.3 (Difco) 10gTrypti
case (BBL) 5gYe
ast extract (Difco)
3gTween 80
1 gSolution B
5ynllL−cysteine−Hcl−H
20 0.2 g指示薬溶液
20艷Agar (Dirco)
1.5gpoはビフィズス菌用で
は?.2、L. acidophilusでは6.5に
調整した。Fallen Rat Invasion 1 Bacto-Liver (Difco) Leachate
1.000ntQProteose peptone
No. 3 (Difco) 10g Trypti
case (BBL) 5gYe
ast extract (Difco)
3gTween 80
1gSolution B
5ynllL-cysteine-Hcl-H
20 0.2 g indicator solution
20 Agar (Dirco)
Is 1.5gpo for bifidobacteria? .. 2.L. acidophilus, it was adjusted to 6.5.
上の表中でBacto−Liver浸出液とは、Bac
to−Liver(D+fco)5.5 gに1,05
0+u9の精製水ー20一
を加え、50〜60℃温浴中で時々攪拌しながら約1時
間浸出した後、濾紙で濾過した濾液である。
\Soluti
on Bとは、Mg2SOa4}1p0 10g1
FeSOA4H20 0.5g1NaCI 0.5g.
及びMnSO40.337 gを250m9の精製水に
溶解したものである。In the above table, Bacto-Liver infusion solution refers to Bacto-Liver infusion solution.
to-Liver (D+fco) 5.5 g to 1.05
This is the filtrate obtained by adding 0+u9 purified water-20-1, infusing in a 50-60°C hot bath for about 1 hour with occasional stirring, and then filtering with a filter paper.
\Soluti
on B means Mg2SOa4}1p0 10g1
FeSOA4H20 0.5g1NaCI 0.5g.
and MnSO40.337 g were dissolved in 250 m9 of purified water.
指示薬溶液とは、L. acldophllusの同定
の場合、 l gのクロロフェノールレッドを0.1N
NaOHで微アルカリ性にして精製水で総量500m
9にしたものであり、ビフィズス菌の同定の場合、プロ
モクレゾールパープルIg少量の純メタノールに溶解さ
せた後、0.1N NaOHで微アルカリ性とし、精製
水で総i1500m9にしたものである。The indicator solution is L. acldophllus, 1 g of chlorophenol red was diluted with 0.1N
Make it slightly alkaline with NaOH and add purified water to a total volume of 500m.
In the case of identifying bifidobacteria, promocresol purple Ig was dissolved in a small amount of pure methanol, made slightly alkaline with 0.1N NaOH, and made with purified water to a total i of 1500m9.
PYFブロス
Tryptone (BBL)
10gYeast extract (Dirco)
5gFildes solution
40wn9Salts solut
[on 40dL−cystei
ne4cl−H20 0.5
g精製水 92〇一pHは
7.2に調整した。PYF Broth Tryptone (BBL)
10gYeast extract (Dirco)
5gFildes solution
40wn9Saltssolut
[on 40dL-cystei
ne4cl-H20 0.5
g Purified water 9201 pH was adjusted to 7.2.
上の表中でFildes solutionの作り方は
以下の通り。生理食塩水150mll,濃塩酸6艷、馬
血液50d及びペブシン(1:10,000、Difc
o)Igを250ml2フラスコに入れてよく混合し、
55℃に保ったウォーターバスで一晩放置して馬血液を
ペプシンにより消化させる。20%のNaOH溶液12
−を加え、I)l’lが正確に7.6になるように N
aOH又はHCIで修正する。このようにして出来上が
ったFildes solutionはクロロフォルム
2mllを添加して冷蔵保存する。The method for creating the Fildes solution in the table above is as follows. 150 ml of physiological saline, 6 liters of concentrated hydrochloric acid, 50 d of horse blood, and pevcin (1:10,000, Difc
o) Add Ig to 250ml2 flask and mix well.
Horse blood is digested with pepsin by leaving it overnight in a water bath kept at 55°C. 20% NaOH solution 12
-, so that I)l'l becomes exactly 7.6 N
Correct with aOH or HCI. The Fildes solution thus prepared was added with 2 ml of chloroform and stored in a refrigerator.
上の表中のSalts solutionの作り方は以
下の通り。無水CaCl20.2g+!:MgSOn
0.2gとを300艷の精製水に溶解し、次いでこの溶
液をよく攪拌しつつ精製水500−を加えN K2HP
O41 gsKHaPOa 1 g, NaHC031
0 g及びNaCl2gを加えて完全に溶かし、更に2
00m9の精製水を加えて混合する。このようにして出
来上がったSalt=21−
solutionは4℃で保存する。How to make the Salts solution in the table above is as follows. Anhydrous CaCl20.2g+! :MgSOn
Dissolve 0.2g in 300ml of purified water, then add 500ml of purified water while stirring the solution well.
O41 gsKHaPOa 1 g, NaHC031
Add 0 g and 2 g of NaCl to dissolve completely, and then add 2 g of NaCl.
Add 00 m9 of purified water and mix. The Salt=21-solution thus prepared is stored at 4°C.
これらの培地は指示薬溶液以外の成分を加熱して溶解し
、IlMを指定の値に調整して指示薬溶液を添加、12
1℃20分間の蒸気威菌を行った。For these media, components other than the indicator solution are dissolved by heating, IIM is adjusted to the specified value, and the indicator solution is added.
Steam incubation was performed at 1°C for 20 minutes.
濾過戚菌した純度90%のβ−グルフシルソルビトール
、本発明の製造例1、製造例2又は実施例2で最終的に
得られたグルコシルソルビトール組成物の100Ill
g/Iu9水溶液1 00dをそれぞれ無菌的に上記滅
菌済みの培地2dに加えた。一方対照としてグルコース
、ラフィノース、ソルビトール及び純度90%のα−グ
ルコシルソルビトールの各100mg/艷水溶液100
dをそれぞれ無菌的に上記滅菌済みの培地2艷に加えた
培地を用意した。以上を本実施例に供する培地とした。Filtered β-glufusyl sorbitol with a purity of 90%, 100 Ill of the glucosyl sorbitol composition finally obtained in Production Example 1, Production Example 2 or Example 2 of the present invention
100 d of g/Iu9 aqueous solution was aseptically added to 2 d of the above-mentioned sterilized medium. On the other hand, as a control, 100 mg each of glucose, raffinose, sorbitol, and α-glucosyl sorbitol with a purity of 90%/100 g of aqueous solution
d was added aseptically to the two sterilized mediums described above to prepare a medium. The above was used as the medium used in this example.
以上のようにして用意した各培地に、上記各菌を含む生
理食塩水(菌濃度は約10”〜!09個/艷)を50ρ
ずつ植え付けて培養を開始した。ビフィズス菌% B
act. vulgatus及びC. perfrin
gensはGasPack法を用いて嫌気的条件下で、
他の菌はロータリーシェーカーにより攪拌しつつ好気的
条件下でそれぞれ3日間、37℃で培養した。50 ρ of physiological saline containing each of the above bacteria (bacteria concentration is approximately 10"~!09 cells/barb) was added to each culture medium prepared as above.
They were planted and culture started. Bifidobacteria% B
act. C. vulgatus and C. vulgatus. perfrin
gens under anaerobic conditions using the GasPack method.
The other bacteria were each cultured at 37° C. for 3 days under aerobic conditions with stirring using a rotary shaker.
菌の増殖は、培地のpHの低下を主な指標とし、これに
測度を加味して判定した。判定の基準は以下の通りであ
る。菌を加えずに上記培養条件と同じ状態に置いておい
た培地をコントロールとして、原則としては菌を入れた
培地のpHの低下が2.0以上のものを柑、1.01〜
2.0のものを丑、0.51〜1.0のものを士、0.
31〜0、50のものを士、0.30以下のものをーと
した。これに目視による濁度の評価も考慮して最終的に
菌増殖の判断を下した。結果を表1に示す。Bacterial growth was determined by using the decrease in pH of the medium as the main indicator, taking measurements into account. The criteria for judgment are as follows. As a general rule, if the pH of the culture medium containing bacteria decreases by 2.0 or more, using a medium that is kept under the same culture conditions as above without adding bacteria, it is classified as citrus, 1.01~
2.0 is ox, 0.51-1.0 is shi, 0.
Those with a rating of 31 to 0 and 50 were designated as -, and those with a rating of 0.30 or less were designated as -. In addition, a visual evaluation of turbidity was taken into consideration and the final judgment of bacterial growth was made. The results are shown in Table 1.
(以下余白)
=24
表1が示すように、純度90%のβ−グルコシルソルビ
トール或いは、本発明の製造例1、製造例2又は実施例
2により得られたグルコシルソルビトール組成物は、い
ずれもビフィズス菌の増殖促進作用があるのに対してN
Bact. vulgatuss E.coll
及びC. perfringensの増殖促進作用は全
く無く、ビフィズス菌に対する選択性が非常に高い。(The following is a blank space) = 24 As shown in Table 1, β-glucosyl sorbitol with a purity of 90% or the glucosyl sorbitol composition obtained in Production Example 1, Production Example 2, or Example 2 of the present invention are all bifidus. While N has the effect of promoting bacterial growth,
Bact. vulgatuss E. coll
and C. Perfringens has no growth-promoting effect at all, and has very high selectivity for Bifidobacteria.
これに対し、従来ビフィズス菌を選択的に増殖させると
されているラフィノースはBact. vulgatu
s及びC. parfringensをかなり増殖させ
る。又、本発明に係るβ−グルコシルソルビトールと構
造が極めて類似しているα−グルコシルソルビトールも
、低レベルとはいえ、Bact. vulgatus及
びC.perfr ingensを増殖させる作用があ
る。On the other hand, raffinose, which is conventionally thought to selectively grow Bifidobacteria, is Bact. Vulgatu
s and C.S. parfringens grows considerably. Furthermore, α-glucosylsorbitol, which has a very similar structure to β-glucosylsorbitol according to the present invention, is also found in Bact. C. vulgatus and C. vulgatus. It has the effect of proliferating perfringens.
以上から、ビフィズス菌に対する選択性においてβ−グ
ルコシルソルビトールは、従来知られているビフィズス
菌増殖促進剤よりも優れていることが示される。From the above, it is shown that β-glucosylsorbitol is superior to conventionally known bifidobacteria growth promoters in selectivity for bifidobacteria.
以」二I"2
Claims (1)
有効成分とするビフィズス菌増殖促進剤。 2、請求項1の二糖のグルコース部分又はソルビトール
部分に更にグルコースが1乃至3個β結合している三糖
、四糖、若しくは五糖を有効成分とするビフィズス菌増
殖促進剤。3、請求項1に記載の二糖、請求項2に記載
の三糖、四糖及び五糖、からなる群から2種類以上の糖
を選んでなる組成物を有効成分とするビフィズス菌増殖
促進剤。 4、ソルビトールとグルコースとの混合水溶液を酸触媒
の存在下、加熱することを特徴とする請求項1乃至請求
項3のビフィズス菌増殖促進剤の製造方法。 5、酸触媒が鉱酸、有機酸、及びH^+形陽イオン交換
樹脂からなる群から選ばれたものである請求項4のビフ
ィズス菌増殖促進剤の製造方法。 6、ソルビトールに対するグルコースの重量比が0.2
乃至5である請求項4の製造方法。 7、加熱温度が70℃乃至150℃である請求項4の製
造方法。[Scope of Claims] 1. A bifidobacteria growth promoter containing a disaccharide in which glucose is β-linked to sorbitol as an active ingredient. 2. A bifidobacteria growth promoter comprising a trisaccharide, tetrasaccharide, or pentasaccharide as an active ingredient, in which 1 to 3 glucoses are further β-linked to the glucose moiety or sorbitol moiety of the disaccharide according to claim 1. 3. Bifidobacteria growth promotion using a composition comprising two or more types of saccharides selected from the group consisting of the disaccharide according to claim 1 and the trisaccharide, tetrasaccharide, and pentasaccharide according to claim 2 as an active ingredient. agent. 4. The method for producing a bifidobacteria growth promoter according to any one of claims 1 to 3, characterized in that the mixed aqueous solution of sorbitol and glucose is heated in the presence of an acid catalyst. 5. The method for producing a bifidobacteria growth promoter according to claim 4, wherein the acid catalyst is selected from the group consisting of mineral acids, organic acids, and H^+ type cation exchange resins. 6. Weight ratio of glucose to sorbitol is 0.2
5. The manufacturing method according to claim 4. 7. The manufacturing method according to claim 4, wherein the heating temperature is 70°C to 150°C.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5494689A JPH02234667A (en) | 1989-03-09 | 1989-03-09 | Proliferation promoter for lactobacillus bifidus and production thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5494689A JPH02234667A (en) | 1989-03-09 | 1989-03-09 | Proliferation promoter for lactobacillus bifidus and production thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH02234667A true JPH02234667A (en) | 1990-09-17 |
Family
ID=12984821
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP5494689A Pending JPH02234667A (en) | 1989-03-09 | 1989-03-09 | Proliferation promoter for lactobacillus bifidus and production thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02234667A (en) |
-
1989
- 1989-03-09 JP JP5494689A patent/JPH02234667A/en active Pending
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