JP2002128791A - New saccharide and its use as antimicrobial agent - Google Patents
New saccharide and its use as antimicrobial agentInfo
- Publication number
- JP2002128791A JP2002128791A JP2000323890A JP2000323890A JP2002128791A JP 2002128791 A JP2002128791 A JP 2002128791A JP 2000323890 A JP2000323890 A JP 2000323890A JP 2000323890 A JP2000323890 A JP 2000323890A JP 2002128791 A JP2002128791 A JP 2002128791A
- Authority
- JP
- Japan
- Prior art keywords
- saccharide
- retention time
- present
- ion exchange
- minutes
- 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.)
- Withdrawn
Links
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は新規糖質およびその
抗菌剤としての使用に関する。[0001] The present invention relates to a novel saccharide and its use as an antibacterial agent.
【０００２】[0002]
【従来の技術】従来、食品などの保存料として安息香酸
やソルビン酸など種々の化学物質が合成され利用されて
いる。しかし、近年、健康と食物に対する関心が深ま
り、食品の安全性に対する要求も高まると共に天然また
は自然に近い食品に対する関心が高まってきている。こ
のような指向の高まりは、保存料に対する要求にも著し
い影響を与えており、合成保存料を避け、これに代わる
安全な抗菌性物質の使用が望まれ多くの研究開発が成さ
れてきた。近年、多糖類である澱粉から酵素の作用によ
り生産できる、１,５−Ｄ−アンヒドロフルクトースに
ついて抗酸化性や抗菌性といった特性を持つことが報告
されている。2. Description of the Related Art Conventionally, various chemical substances such as benzoic acid and sorbic acid have been synthesized and used as preservatives for foods and the like. However, in recent years, interest in health and food has increased, and demand for food safety has increased, and interest in natural or near-natural foods has increased. Such an increase in orientation has also significantly affected the demand for preservatives, and it has been desired to use a safe antibacterial substance instead of synthetic preservatives, and much research and development has been carried out. In recent years, it has been reported that 1,5-D-anhydrofructose, which can be produced from starch, which is a polysaccharide by the action of an enzyme, has properties such as antioxidant properties and antibacterial properties.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、抗菌
能力を有する新規糖質を提供することにある。本発明の
他の目的は、１,５−Ｄ−アンヒドロフルクトースを加
熱して生成されうる抗菌能力を有する新規糖質を提供す
ることにある。本発明のさらに他の目的は、本発明の新
規糖質を抗菌剤として使用することを提供することにあ
る。本発明のさらに他の目的および利点は、以下の説明
から明らかになろう。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel saccharide having antibacterial ability. It is another object of the present invention to provide a novel saccharide having an antibacterial ability that can be produced by heating 1,5-D-anhydrofructose. Still another object of the present invention is to provide use of the novel saccharide of the present invention as an antibacterial agent. Still other objects and advantages of the present invention will become apparent from the following description.
【０００４】[0004]
【課題を解決するための手段】本発明の上記目的および
利点は、本発明によれば、第１に、高速液体クロマトグ
ラフィーで、スチレンとジビニルベンゼンとの架橋度８
％の共重合体であり且つナトリウムスルホネート基をイ
オン交換基とする強酸性イオン交換樹脂を充填剤とする
カラム（三菱化学ＭＣＩ ＧＥＬ ＣＫ ０８ Ｓ）を
用い、カラム温度４０℃、水を媒体とし流速１ｍｌ／分
で測定した場合、標準物質のマルトースの保持時間が
８.８±０.２分、フルクトースの保持時間が１２.５±
０.２分であるとき、保持時間２４.０±０.２分を示す
ことを特徴とする新規糖質によって達成される。本発明
の上記目的および利点は、第２に、本発明の新規糖質の
抗菌剤としての使用によって達成される。SUMMARY OF THE INVENTION The above objects and advantages of the present invention are as follows. According to the present invention, first, the degree of crosslinking between styrene and divinylbenzene by high performance liquid chromatography is 8%.
% Of the copolymer (Mitsubishi Chemical MCI GEL CK 08 S) using a highly acidic ion exchange resin having a sodium sulfonate group as an ion exchange group and a column temperature of 40 ° C., water as a medium, and a flow rate. When measured at 1 ml / min, the retention time of maltose as a standard substance is 8.8 ± 0.2 minutes, and the retention time of fructose is 12.5 ±
This is achieved by a novel saccharide characterized by exhibiting a retention time of 24.0 ± 0.2 minutes when it is 0.2 minutes. The above objects and advantages of the present invention are secondly achieved by using the novel saccharide of the present invention as an antibacterial agent.
【０００５】以下、本発明について詳細する。本発明の
新規糖質は、例えば、３０重量％の濃度で溶解した１,
５−Ｄ−アンヒドロフルクトース溶液を、１００℃以上
の温度、より好ましくは１２０℃で、６０分間加熱処理
することによって製造することができる。Hereinafter, the present invention will be described in detail. The novel saccharide of the present invention is, for example, 1,1% dissolved at a concentration of 30% by weight.
The 5-D-anhydrofructose solution can be produced by heat-treating at a temperature of 100 ° C or higher, more preferably at 120 ° C, for 60 minutes.
【０００６】すなわち、加熱処理された溶液を、スチレ
ンとジビニルベンゼンとの架橋度８％の共重合体であり
且つナトリウムスルホネート基をイオン交換基とする強
酸性イオン交換樹脂を充填剤とするカラム（三菱化学Ｍ
ＣＩ ＧＥＬ ＣＫ ０８Ｓ）を用い、カラム温度４０
℃、溶媒に水を用い流速１ｍｌ／分、検出器に屈折率計
を用いた高速液体クロマトグラフィーにより分析し、さ
らにその高速液体クロマトグラフィーを用いて、分取に
よる精製を繰り返し、最終的に９９％以上の純度を示す
新規糖質が得られた。That is, the heat-treated solution is converted into a column using a strongly acidic ion exchange resin as a filler, which is a copolymer of styrene and divinylbenzene having a degree of crosslinking of 8% and has sodium sulfonate groups as ion exchange groups. Mitsubishi Chemical M
CI GEL CK 08S) and a column temperature of 40.
The solution was analyzed by high performance liquid chromatography using water as a solvent, a flow rate of 1 ml / min, and a refractometer as a detector. Purification by preparative separation was repeated using the high performance liquid chromatography. %, A new saccharide having a purity of not less than 10% was obtained.
【０００７】その糖質の特性を高速液体クロマトグラフ
ィーにより測定した。高速液体クロマトグラフィーは三
菱化学ＭＣＩ ＧＥＬ ＣＫ ０８ Ｓを用い流速１ｍ
ｌ／分、カラム温度４０℃、水を溶媒とし、検出器には
示差屈折計を用いた。この条件で新規糖質の保持時間は
２４.０±０.２分であった。また、そのとき標準物質の
マルトースおよびフラクトースの保持時間はそれぞれ
８.８±０.２分および１２.５±０.２分であった。[0007] The characteristics of the saccharide were measured by high performance liquid chromatography. High performance liquid chromatography was performed using Mitsubishi Chemical MCI GEL CK 08 S at a flow rate of 1 m.
1 / min, a column temperature of 40 ° C., water was used as a solvent, and a differential refractometer was used as a detector. Under these conditions, the retention time of the new saccharide was 24.0 ± 0.2 minutes. At that time, the retention times of maltose and fructose as standard substances were 8.8 ± 0.2 minutes and 12.5 ± 0.2 minutes, respectively.
【０００８】本発明の新規糖質を製造するために用いら
れた１,５−Ｄ−アンヒドロフルクトースは、モチトウ
モロコシ澱粉に紅藻から抽出・精製したグルカンリアー
ゼを作用させ、ゲル濾過クロマトグラフィーで精製する
ことにより製造することができる。すなわち、かくして
製造された１,５−Ｄ−アンヒドロフルクトースは核磁
気共鳴により同定したところ、既に報告されている１,
５−Ｄ−アンヒドロフルクトースと炭素化学シフト値が
すべて一致した。また高速液体クロマトグラフィーによ
り測定したこの１,５−Ｄ−アンヒドロフルクトースの
純度は約９９％であった。本発明の新規糖質は強力な抗
菌能力を有する。The 1,5-D-anhydrofructose used for producing the novel saccharide of the present invention is obtained by reacting glucan lyase extracted and purified from red algae on waxy maize starch, and performing gel filtration chromatography. It can be produced by purification. That is, the thus-produced 1,5-D-anhydrofructose was identified by nuclear magnetic resonance.
The 5-D-anhydrofructose and carbon chemical shift values were all the same. The purity of this 1,5-D-anhydrofructose measured by high performance liquid chromatography was about 99%. The novel saccharide of the present invention has a strong antibacterial ability.
【０００９】本発明の新規糖質存在下で各種細菌を培養
し増殖に及ぼす影響を調べた。第一に、本発明の糖質の
各種細菌に対する最小生育阻止濃度を試験した。菌株を
生理食塩水に懸濁後、寒天培地に白金耳を用いて接種
し、コロニーが形成されるまで培養した。次いで、滅菌
した楊枝を用いて細菌をコロニーから本発明の糖質を含
む寒天培地に接種した。コントロールには本発明の糖質
の代わりに１,５−Ｄ−アンヒドロフルクトースを接種
した同培地を用いた。増殖能の判定は一晩培養後、目視
により形成されたコロニーを観察することにより行っ
た。結果を表１に示す。[0009] In the presence of the novel carbohydrate of the present invention, various bacteria were cultured and their effects on growth were examined. First, the minimum inhibitory concentration of the saccharide of the present invention against various bacteria was tested. After suspending the strain in physiological saline, the agar medium was inoculated using a platinum loop and cultured until a colony was formed. Next, bacteria were inoculated from the colony to the agar medium containing the saccharide of the present invention using a sterilized toothpick. As a control, the same medium inoculated with 1,5-D-anhydrofructose instead of the saccharide of the present invention was used. The proliferation ability was determined by observing the formed colonies visually after culturing overnight. Table 1 shows the results.
【表1】 【table 1】
【００１０】表１より、いずれの細菌に対しても、本発
明の新規糖質は、０.３％以下の濃度で増殖阻害効果を
持つこと、中でも耐熱、好酸性菌Alicyclobacillus ac
idoterrestrisに対しても低濃度で増殖阻害効果を持つ
ことがわかる。よってこの糖質は、１,５−Ｄ−アンヒ
ドロフルクトースよりも更に高い抗菌活性を持つ物質で
あることが明らかとなった。本発明によれば、それ故上
記のとおり、本発明の新規糖質を抗菌剤として使用する
ことが同様に提供される。本発明の新規糖質は、食品工
業、医薬品工業、化学工業などで抗菌剤として利用可能
である。利用方法としては、例えば、本発明の糖質を食
品の原料または製品に添加して抗菌剤として利用するこ
とが可能である。From Table 1, it can be seen that the novel carbohydrate of the present invention has a growth inhibitory effect at a concentration of 0.3% or less against any of the bacteria, especially, a heat-resistant, acidophile Alicyclobacillus ac.
It can be seen that even at a low concentration, idoterrestris has a growth inhibitory effect. Therefore, it was revealed that this saccharide is a substance having an even higher antibacterial activity than 1,5-D-anhydrofructose. According to the present invention, therefore, there is also provided, as described above, the use of the novel saccharides of the present invention as antibacterial agents. The novel saccharide of the present invention can be used as an antibacterial agent in the food industry, pharmaceutical industry, chemical industry and the like. As an application method, for example, the saccharide of the present invention can be added to a raw material or product of food and used as an antibacterial agent.
【００１１】[0011]
【発明の効果】本発明によれば、優れた抗菌能力を有す
る新規な糖質が提供される。本発明の新規糖質は水溶性
の糖質であり且つ安定性が高く、例えば種々の食品に直
接混合して使用することによってわずかな量で強力な抗
菌作用を維持することが可能である。According to the present invention, a novel saccharide having excellent antibacterial ability is provided. The novel carbohydrate of the present invention is a water-soluble carbohydrate and has high stability. For example, it is possible to maintain a strong antibacterial action in a small amount by directly mixing it with various foods.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 藤末 真実 鹿児島県鹿児島市南栄３−20 日本澱粉工 業株式会社内 Ｆターム(参考） 4B064 AF01 AF02 BH05 CA21 CC03 CD19 CE10 DA02 DA10 4C057 AA13 BB01 4C086 AA01 AA02 AA03 AA04 EA01 MA01 MA04 NA14 ZB35 ────────────────────────────────────────────────── ─── Continuing from the front page (72) Inventor Mami Fujisue 3-20 Minamiei, Kagoshima City, Kagoshima Prefecture Japan Starch Industries Co., Ltd. F-term (reference) 4B064 AF01 AF02 BH05 CA21 CC03 CD19 CE10 DA02 DA10 4C057 AA13 BB01 4C086 AA01 AA02 AA03 AA04 EA01 MA01 MA04 NA14 ZB35
Claims (3)
ンとジビニルベンゼンとの架橋度８％の共重合体であり
且つナトリウムスルホネート基をイオン交換基とする強
酸性イオン交換樹脂を充填剤とするカラムを用い、カラ
ム温度４０℃、水を溶媒とし流速１ｍｌ／分で測定した
場合、標準物質のマルトースの保持時間が８.８±０.２
分、フルクトースの保持時間が１２.５±０.２分である
時、保持時間２４.０±０.２分を示すことを特徴とする
新規糖質。1. A high-performance liquid chromatography using a column comprising a strongly acidic ion exchange resin which is a copolymer of styrene and divinylbenzene with a degree of crosslinking of 8% and has sodium sulfonate groups as ion exchange groups. When measured at a column temperature of 40 ° C. and a flow rate of 1 ml / min using water as a solvent, the retention time of maltose as a standard substance was 8.8 ± 0.2.
A novel saccharide characterized by exhibiting a retention time of 24.0 ± 0.2 minutes when the retention time of fructose is 12.5 ± 0.2 minutes.
溶解した溶液を１００℃以上の温度で６０分間加熱して
生成される請求項１に記載の新規糖質。2. The novel saccharide according to claim 1, which is produced by heating a solution in which 1,5-D-anhydrofructose is dissolved at a temperature of 100 ° C. or higher for 60 minutes.
ての使用。3. Use of the novel saccharide according to claim 1 as an antibacterial agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000323890A JP2002128791A (en) | 2000-10-24 | 2000-10-24 | New saccharide and its use as antimicrobial agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000323890A JP2002128791A (en) | 2000-10-24 | 2000-10-24 | New saccharide and its use as antimicrobial agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002128791A true JP2002128791A (en) | 2002-05-09 |
Family
ID=18801500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000323890A Withdrawn JP2002128791A (en) | 2000-10-24 | 2000-10-24 | New saccharide and its use as antimicrobial agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002128791A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4726629B2 (en) * | 2003-12-12 | 2011-07-20 | 株式会社ニチレイフーズ | Bacterial growth inhibitor or inhibitor using substances derived from acerola fruit |
| JP2016129508A (en) * | 2015-01-14 | 2016-07-21 | アサマ化成株式会社 | Taste modifier |
-
2000
- 2000-10-24 JP JP2000323890A patent/JP2002128791A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4726629B2 (en) * | 2003-12-12 | 2011-07-20 | 株式会社ニチレイフーズ | Bacterial growth inhibitor or inhibitor using substances derived from acerola fruit |
| JP2016129508A (en) * | 2015-01-14 | 2016-07-21 | アサマ化成株式会社 | Taste modifier |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Withdrawal of application because of no request for examination |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20080108 |