JPH10226701A - Antibacterial composition containing oligoglacturonic acid and its production - Google Patents
Antibacterial composition containing oligoglacturonic acid and its productionInfo
- Publication number
- JPH10226701A JPH10226701A JP3019397A JP3019397A JPH10226701A JP H10226701 A JPH10226701 A JP H10226701A JP 3019397 A JP3019397 A JP 3019397A JP 3019397 A JP3019397 A JP 3019397A JP H10226701 A JPH10226701 A JP H10226701A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- oligogalacturonic acid
- oligogalacturonic
- composition
- unsaturated
- 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
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規なペクチン分
解物組成物、その製造方法及びそれを含有する抗菌性組
成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel pectin degradation product composition, a method for producing the same, and an antibacterial composition containing the same.
【０００２】[0002]
【従来の技術】ペクチンは、植物体等に広く分布してい
るコロイド性の多糖類で、主に、Ｄ−ガラクツロン酸の
α−１，４結合による直鎖状重合体のカルボキシル基が
一部メチルエステル基となった構造を有しており、従来
その高い粘度等の物理的特性及び長年の食習慣により立
証された生体に対する安全性を利用して、食品加工の分
野においてゲル化剤、増粘剤等として、また医薬の分野
において生理活性物質の吸収遅延剤等として利用されて
いる。2. Description of the Related Art Pectin is a colloidal polysaccharide widely distributed in plants and the like. Mainly, carboxyl groups of a linear polymer formed by α-1,4 bonds of D-galacturonic acid are partially contained. It has a structure that has become a methyl ester group, and by utilizing its physical properties such as high viscosity and safety against living organisms that have been proven by long-standing eating habits, gelling agents have been used in the field of food processing. It is used as a thickener, etc., and as a retarder of absorption of a physiologically active substance in the field of medicine.
【０００３】また、ペクチンの分解物は抗菌作用を示す
ことが知られており、安全な天然由来の抗菌剤又は防腐
剤として食品等への使用の可能性が検討されている。例
えば、特公昭６２−５３１４０号公報には、ペクチンを
酵素、酸、アルカリ等により６００〜５０００にした分
解物が開示されている。しかしながら、ペクチン分解物
の高い安全性を有し飲食品等の人体に対する安全性が求
められる製品に使用でき、且つさらに抗菌作用の強い物
質が求められている。[0003] In addition, pectin degradation products are known to exhibit an antibacterial effect, and the possibility of using them as safe natural antibacterial agents or preservatives in foods and the like has been studied. For example, JP-B-62-53140 discloses a degradation product obtained by converting pectin to 600 to 5000 with an enzyme, acid, alkali or the like. However, there is a need for a substance which has high safety of a pectin degradation product and which can be used for products requiring safety to the human body, such as food and drink, and which has a stronger antibacterial action.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、安全
性、及び従来のペクチン分解物よりさらに強い抗菌作用
を備える物質を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a substance having safety and an antibacterial action which is stronger than that of conventional pectin degradation products.
【０００５】本発明の他の目的は、前記物質を簡便に製
造する製造方法を提供することにある。[0005] Another object of the present invention is to provide a production method for easily producing the above-mentioned substance.
【０００６】[0006]
【課題を解決するための手段】本発明によれば、６〜１
５量体のオリゴガラクツロン酸及び２〜１５量体の４，
５−不飽和オリゴガラクツロン酸を含有するオリゴガラ
クツロン酸含有組成物が提供される。According to the present invention, 6-1
Pentameric oligogalacturonic acid and 2-15 mer 4,4
Oligogalacturonic acid-containing compositions containing 5-unsaturated oligogalacturonic acids are provided.
【０００７】また本発明によれば、ペクチンを、ｐＨ
６．５〜７．２に調整した水溶液中において８０〜１０
０℃に加熱して分子量１０００〜５０００のオリゴガラ
クツロン酸及び分子量３００〜５０００の４，５−不飽
和オリゴガラクツロン酸の混合物を得、次いでペクチナ
ーゼにより酵素反応させることを特徴とする、前記オリ
ゴガラクツロン酸組成物の製造方法が提供される。[0007] According to the present invention, pectin is converted to pH
80 to 10 in an aqueous solution adjusted to 6.5 to 7.2
Heating the mixture to 0 ° C. to obtain a mixture of oligogalacturonic acid having a molecular weight of 1,000 to 5,000 and 4,5-unsaturated oligogalacturonic acid having a molecular weight of 300 to 5,000, followed by an enzymatic reaction with pectinase; A method of making a composition is provided.
【０００８】さらに本発明によれば、６〜１５量体のオ
リゴガラクツロン酸及び２〜１５量体の４，５−不飽和
オリゴガラクツロン酸を含有する抗菌性組成物が提供さ
れる。Further, according to the present invention, there is provided an antibacterial composition containing 6 to 15-mer oligogalacturonic acid and 2 to 15-mer 4,5-unsaturated oligogalacturonic acid.
【０００９】[0009]
【発明の実施の形態】本発明のオリゴガラクツロン酸含
有組成物は、オリゴガラクツロン酸及び４，５−不飽和
オリゴガラクツロン酸を含有する。DETAILED DESCRIPTION OF THE INVENTION The oligogalacturonic acid-containing composition of the present invention contains oligogalacturonic acid and 4,5-unsaturated oligogalacturonic acid.
【００１０】前記オリゴガラクツロン酸とは、複数のガ
ラクツロン酸がα−１，４結合により結合したものを意
味する。また、前記４，５−不飽和オリゴガラクツロン
酸とは、その非還元末端に、下記式（１）で表される不
飽和ガラクツロン酸を有するオリゴガラクツロン酸を意
味する。The oligogalacturonic acid means a plurality of galacturonic acids linked by α-1,4 bonds. The 4,5-unsaturated oligogalacturonic acid means an oligogalacturonic acid having an unsaturated galacturonic acid represented by the following formula (1) at its non-reducing terminal.
【００１１】[0011]
【化１】 Embedded image
【００１２】本発明のオリゴガラクツロン酸含有組成物
中の前記オリゴガラクツロン酸は、６〜１５量体、好ま
しくは６〜１０量体であり、前記４，５−不飽和オリゴ
ガラクツロン酸は、２〜１５量体、好ましくは２〜１０
量体である。また、本発明のオリゴガラクツロン酸含有
組成物中の前記オリゴガラクツロン酸及び４，５−不飽
和オリゴガラクツロン酸の含有割合は、７：３〜９：１
が好ましい。The oligogalacturonic acid in the oligogalacturonic acid-containing composition of the present invention is a 6- to 15-mer, preferably a 6- to 10-mer, and the 4,5-unsaturated oligogalacturonic acid is a 2- to 5-mer. 15 mer, preferably 2 to 10
Is a monomer. The content ratio of the oligogalacturonic acid and 4,5-unsaturated oligogalacturonic acid in the oligogalacturonic acid-containing composition of the present invention is 7: 3 to 9: 1.
Is preferred.
【００１３】本発明のオリゴガラクツロン酸組成物の製
造方法では、原料としてペクチンを用いる。前記ペクチ
ンとしては、特に限定されず、メチル基含量２〜１２％
の通常のものを使用することができるが、特にメチル基
含量２〜６％の低メトキシルペクチンを用いることが、
好ましい組成の組成物を容易に製造できるため好まし
い。また前記ペクチンは、特に限定されないが、ブド
ウ、リンゴ、柑橘類等の植物等の天然物由来のものを用
いることが、製品を飲食品等人体に対する安全性が求め
られる用途に使用した場合の安全性が確保できるため好
ましい。In the method for producing an oligogalacturonic acid composition of the present invention, pectin is used as a raw material. The pectin is not particularly limited, and has a methyl group content of 2 to 12%.
Can be used. Particularly, it is preferable to use low methoxyl pectin having a methyl group content of 2 to 6%.
It is preferable because a composition having a preferable composition can be easily produced. Further, the pectin is not particularly limited, but it is possible to use those derived from natural products such as plants such as grapes, apples, citrus fruits, and the like, if the product is used for applications requiring safety to the human body such as food and drink. Is preferable because it can secure
【００１４】本発明の製造方法では、前記ペクチンを、
ｐＨ６．５〜７．２、好ましくは６．８〜７．０に調整
した水溶液中において８０〜１００℃、好ましくは９５
〜９８℃に加熱して分子量１０００〜５０００のオリゴ
ガラクツロン酸及び分子量３００〜５０００、好ましく
は３００〜２０００の４，５−不飽和オリゴガラクツロ
ン酸の混合物を得る。前記ｐＨの調整方法は、特に限定
されないが、ＮａＯＨ及び／又はＨＣｌ等を加えること
により行うことができる。また、前記加熱は、特に限定
されないが、反応液中の４，５−不飽和ガラクツロン酸
量の増加をチオバルビツール酸反応等で経時的に測定
し、４，５−不飽和ガラクツロン酸量が一定となった時
点で反応を終了することができる。このような加熱反応
を行うことにより、特に前述の低メトキシルペクチンを
用いた場合、通常ペクチン鎖中のメチル基を含有するガ
ラクツロン酸単位の非還元末端側の結合がトランス脱離
により切断され好ましい分子量の生成物を容易に得るこ
とができるので好ましい。In the production method of the present invention, the pectin is
80-100 ° C, preferably 95, in an aqueous solution adjusted to pH 6.5-7.2, preferably 6.8-7.0.
Heat to ~ 98 ° C to obtain a mixture of oligogalacturonic acid with a molecular weight of 1000-5000 and 4,5-unsaturated oligogalacturonic acid with a molecular weight of 300-5000, preferably 300-2000. The method of adjusting the pH is not particularly limited, but can be performed by adding NaOH and / or HCl. The heating is not particularly limited, but the increase in the amount of 4,5-unsaturated galacturonic acid in the reaction solution is measured over time by a thiobarbituric acid reaction or the like, and the amount of 4,5-unsaturated galacturonic acid is measured. The reaction can be terminated at a certain point. By performing such a heating reaction, particularly when the above-mentioned low methoxyl pectin is used, the bond at the non-reducing terminal side of the galacturonic acid unit containing a methyl group in the pectin chain is usually cleaved by trans-elimination and has a preferable molecular weight. Is preferred because the product of formula (1) can be easily obtained.
【００１５】本発明の製造方法では、次に、ペクチナー
ゼにより酵素反応を行う。Next, in the production method of the present invention, an enzymatic reaction is carried out with pectinase.
【００１６】前記ペクチナーゼとしては、アスペルギル
ス属(Aspergillus sp.)由来のもの、好ましくはアスペ
ルギルス・ニガー(Aspergillus niger)より抽出したも
の等を使用することができ、これらのペクチナーゼを、
例えば前記反応液に添加し、温度を好ましい範囲に保つ
ことにより酵素反応を行うことができる。As the pectinase, those derived from the genus Aspergillus sp., Preferably those extracted from Aspergillus niger, and the like can be used.
For example, the enzyme reaction can be carried out by adding the mixture to the reaction solution and keeping the temperature within a preferable range.
【００１７】前記ペクチナーゼの添加量は、特に限定さ
れないが、例えばアスペルギルス・ニガー由来の力価１
０００Ｕ／ｇのペクチナーゼを使用した場合、反応系内
の基質／酵素（重量比）の値が１００〜３００となるよ
う添加することが好ましい。The amount of the pectinase to be added is not particularly limited. For example, the titer derived from Aspergillus niger is 1
When 000 U / g pectinase is used, it is preferably added so that the value of the substrate / enzyme (weight ratio) in the reaction system becomes 100 to 300.
【００１８】前記酵素反応の反応温度は常温〜６０℃、
好ましくは３５〜４５℃であることが望ましい。また反
応時間は、反応中に経時的に反応系内のオリゴガラクツ
ロン酸及び４，５−不飽和オリゴガラクツロン酸の量を
ＨＰＬＣ（高速液体クロマトグラフィー）、カルバゾー
ル硫酸法等にて測定し、全ガラクツロン酸量に対するこ
れらの割合が、５０〜９０重量％、好ましくは７０〜８
０重量％となった時点で反応を終了することが好まし
い。The reaction temperature of the enzyme reaction is from room temperature to 60 ° C.
Preferably it is 35-45 degreeC. The reaction time is determined by measuring the amounts of oligogalacturonic acid and 4,5-unsaturated oligogalacturonic acid in the reaction system over time during the reaction by HPLC (high performance liquid chromatography), carbazole sulfate method, etc. These ratios to the acid amount are 50 to 90% by weight, preferably 70 to 8%.
It is preferable to terminate the reaction at the time when the weight becomes 0% by weight.
【００１９】本発明の抗菌性組成物は、前記オリゴガラ
クツロン酸組成物を含有する。本発明の抗菌性組成物
は、前記オリゴガラクツロン酸及び前記４，５−不飽和
オリゴガラクツロン酸の両方の相乗効果により、それぞ
れ単独のものよりも高い抗菌作用を示す。The antibacterial composition of the present invention contains the oligogalacturonic acid composition. The antibacterial composition of the present invention exhibits a higher antibacterial activity than the oligogalacturonic acid and the 4,5-unsaturated oligogalacturonic acid alone, respectively, due to the synergistic effect of both.
【００２０】本発明の抗菌組成物は、飲食品；乳液、化
粧水、コールドクリーム等の化粧品；花卉；青果物；水
耕栽培用資材；養殖用資材；あるいはウェットティッシ
ュ、コンタクトレンズ洗浄液等の衛生用品、事務用品等
の家庭用品等の抗菌剤として使用することができる。The antimicrobial composition of the present invention comprises foods and drinks; cosmetics such as milky lotions, lotions, cold creams, etc .; flowers; fruits and vegetables; materials for hydroponic cultivation; materials for aquaculture; or sanitary articles such as wet tissues and contact lens cleaning liquids. It can be used as an antibacterial agent for household goods such as office supplies.
【００２１】本発明の抗菌組成物の使用形態としては、
特に限定されないが、例えば飲食品等の場合、これらの
製品に０．１〜５．０重量％の割合で添加することによ
り抗菌作用を発現することができる。また紙又は繊維製
の衛生用品又は事務用品等の場合、原料となるパルプ等
に、０．１〜５．０重量％の割合で混合することによ
り、得られる製品に抗菌作用を与えることができる。あ
るいは本発明の抗菌組成物は、エタノール等のアルコー
ル等に０．１〜５．０重量％の割合で含有させ、抗菌
剤、除菌剤、殺菌剤等として細菌の増殖を抑制したい部
位に塗布して、あるいは細菌の増殖を抑制したい部位を
浸漬して使用することができる。The use form of the antimicrobial composition of the present invention includes
Although not particularly limited, for example, in the case of foods and drinks, an antibacterial effect can be exhibited by adding 0.1 to 5.0% by weight to these products. In the case of paper or textile sanitary articles or office supplies, antibacterial action can be imparted to the resulting product by mixing it with pulp or the like at a ratio of 0.1 to 5.0% by weight. . Alternatively, the antibacterial composition of the present invention is contained in an alcohol such as ethanol at a ratio of 0.1 to 5.0% by weight, and applied to a site where bacterial growth is to be suppressed as an antibacterial agent, a disinfectant, a bactericide, or the like. Or by immersing a site where bacterial growth is to be suppressed.
【００２２】[0022]
【発明の効果】本発明のオリゴガラクツロン酸組成物
は、特定のオリゴガラクツロン酸及び特定の４，５−不
飽和オリゴガラクツロン酸を含有するので、安全性、及
び従来のペクチン分解物よりさらに強い抗菌作用を備え
る組成物として有用である。Industrial Applicability The oligogalacturonic acid composition of the present invention contains a specific oligogalacturonic acid and a specific 4,5-unsaturated oligogalacturonic acid, so that it is safer and has a stronger antibacterial activity than conventional pectin degradation products. It is useful as a composition having an effect.
【００２３】また、本発明のオリゴガラクツロン酸組成
物の製造方法は、前記ガラクツロン酸組成物を簡便に製
造することができる製造方法として有用である。The method for producing an oligogalacturonic acid composition according to the present invention is useful as a method for producing the galacturonic acid composition easily.
【００２４】さらに、本発明の抗菌性組成物は、特定の
オリゴガラクツロン酸及び特定の４，５−不飽和オリゴ
ガラクツロン酸を含有するので、安全性、及び従来のペ
クチン分解物よりさらに強い抗菌作用を備え、飲食物を
はじめ人体に対する安全性が必要とされる様々な製品の
抗菌性組成物として有用である。Furthermore, since the antibacterial composition of the present invention contains a specific oligogalacturonic acid and a specific 4,5-unsaturated oligogalacturonic acid, it is safe and has a stronger antibacterial activity than conventional pectin degradation products. It is useful as an antibacterial composition for various products that require safety for human body including food and drink.
【００２５】[0025]
【実施例】以下実施例及び比較例により本発明をより詳
細に説明するが、本発明は、これらに限定されるもので
はない。EXAMPLES The present invention will be described in more detail with reference to the following Examples and Comparative Examples, but the present invention is not limited thereto.
【００２６】[0026]
【実施例１】 （オリゴガラクツロン酸組成物の製造）植物由来のペク
チン（メチル基含有量約２〜６％）を水に溶解し、５重
量％の水溶液とした。これにＮａＯＨを加えてｐＨを中
性に調整した後９８℃で加熱した。反応液中の４，５−
不飽和ガラクツロン酸量の増加をチオバルビツール酸反
応で経時的に測定し、４，５−不飽和ガラクツロン酸量
が一定となった時点で反応を終了した。反応終了後、反
応液を４０℃まで冷却した。この溶液に、アスペルギル
ス・ニガー由来のペクチナーゼ（１０００Ｕ／ｇ）を基
質／酵素比（重量比）が２００となるよう加えた後、４
０℃でインキュベートして反応させた。反応中、経時的
に反応液中に存在する６〜１５量体のオリゴガラクツロ
ン酸及び２〜１５量体の４，５−不飽和オリゴガラクツ
ロン酸の量をＨＰＬＣ法及びカルバゾール硫酸法により
測定し、両オリゴガラクツロン酸合計量が全ガラクツロ
ン酸量の７０〜８０重量％生成した時点で反応を終了さ
せた。反応終了後、反応液を孔径１μ以下の濾過剤で不
純物、未分解物を除き、調製ゲルクロマトグラフィー及
びイオン交換樹脂処理により精製し、オリゴガラクツロ
ン酸組成物の溶液を得た。得られた溶液中には、６〜１
５量体のオリゴガラクツロン酸及び２〜１５量体の４，
５−不飽和オリゴガラクツロン酸が、重量比で７：３の
割合で含まれていた。またオリゴガラクツロン酸の合計
量の、出発物質のペクチンに対する割合は８０重量％で
あった。Example 1 (Production of oligogalacturonic acid composition) Plant-derived pectin (methyl group content: about 2 to 6%) was dissolved in water to prepare a 5% by weight aqueous solution. NaOH was added thereto to adjust the pH to neutral, and then the mixture was heated at 98 ° C. 4,5- in the reaction solution
The increase in the amount of unsaturated galacturonic acid was measured over time by a thiobarbituric acid reaction, and the reaction was terminated when the amount of 4,5-unsaturated galacturonic acid became constant. After the completion of the reaction, the reaction solution was cooled to 40 ° C. To this solution was added pectinase (1000 U / g) derived from Aspergillus niger such that the substrate / enzyme ratio (weight ratio) was 200, and then 4
The reaction was performed by incubation at 0 ° C. During the reaction, the amount of the 6- to 15-mer oligogalacturonic acid and the 2 to 15-mer 4,5-unsaturated oligogalacturonic acid present in the reaction solution over time were measured by HPLC method and carbazole sulfate method, The reaction was terminated when the total amount of both oligogalacturonic acids was 70 to 80% by weight of the total galacturonic acid amount. After the completion of the reaction, the reaction solution was purified by a preparative gel chromatography and an ion-exchange resin treatment to remove impurities and undecomposed substances using a filtering agent having a pore diameter of 1 μ or less to obtain a solution of an oligogalacturonic acid composition. In the resulting solution, 6-1
Pentameric oligogalacturonic acid and 2-15 mer 4,4
The content of 5-unsaturated oligogalacturonic acid was 7: 3 by weight. The ratio of the total amount of oligogalacturonic acid to pectin as a starting material was 80% by weight.
【００２７】[0027]
【実施例２】 （オリゴガラクツロン酸組成物の抗菌活性）各種の細菌
類、酵母類又はカビ類について、実施例１で得られたオ
リゴガラクツロン酸組成物の最小発育阻止濃度（ＭＩ
Ｃ）を測定した。なお培地は、細菌類ではNutrient bro
th、酵母類ではＹＭ培地、カビ類ではＹＭ寒天培地を使
用した。結果を表１に示す。また、比較のため、加熱に
より４，５−不飽和オリゴガラクツロン酸を生成させる
工程を行わなかった他は実施例１と同様の操作を行って
得た、６〜１５量体のオリゴガラクツロン酸のみを含む
ペクチン分解物についても同様にＭＩＣを測定した。結
果を表１に示す。Example 2 (Antimicrobial activity of oligogalacturonic acid composition) The minimum growth inhibitory concentration (MI) of the oligogalacturonic acid composition obtained in Example 1 for various bacteria, yeasts and molds
C) was measured. The culture medium is Nutrient bro
th, YM medium was used for yeasts, and YM agar medium was used for molds. Table 1 shows the results. For comparison, only the 6- to 15-mer oligogalacturonic acid obtained by performing the same operation as in Example 1 except that the step of generating 4,5-unsaturated oligogalacturonic acid by heating was not performed. The MIC was also measured for pectin degradation products containing Table 1 shows the results.
【００２８】[0028]
【表１】 [Table 1]
【００２９】[0029]
【実施例３】 （オリゴガラクツロン酸組成物を含む抗菌剤）実施例１
で得られたオリゴガラクツロン酸組成物を、エタノール
４５重量％を含む水溶液中に、０．５重量％の割合とな
るよう溶解し、抗菌剤溶液とした。この溶液について、
簡易細菌検査スタンプ法によりその抗菌作用を評価し
た。即ち、大腸菌(Escherichia coli)又はブドウ状球菌
(Staphylococcus aureus)を生理食塩水中に菌数１０3個
／ｍｌとなるよう懸濁させたものを０．１ｍｌ分取し
て、平坦な台上に滴下した。次に前記抗菌剤溶液を１０
ｃｍ2当たり０．３ｍｌ塗抹する操作を３回行った。さ
らに２〜３分後、塗抹表面をスタンプ処理し、３０℃、
２４時間の条件で培養した。培養終了後、台上の１０ｃ
ｍ2当たりの菌数を計測した。結果を表２に示す。Example 3 (Antimicrobial Agent Containing Oligogalacturonic Acid Composition) Example 1
The oligogalacturonic acid composition obtained in the above was dissolved in an aqueous solution containing 45% by weight of ethanol at a ratio of 0.5% by weight to obtain an antibacterial agent solution. About this solution,
The antibacterial activity was evaluated by the simple bacterial test stamp method. That is, Escherichia coli or Staphylococcus
(Staphylococcus aureus) suspended in physiological saline so that the number of bacteria was 10 3 cells / ml was collected in 0.1 ml portions and dropped on a flat table. Next, the antibacterial agent solution was added to 10
The operation of smearing 0.3 ml per cm 2 was performed three times. After a few minutes, the smeared surface is stamped,
The cells were cultured for 24 hours. After cultivation, 10c on the table
It was measured number of bacteria per m 2. Table 2 shows the results.
【００３０】また、比較のため、滅菌水、及びオリゴガ
ラクツロン酸組成物を含まない４５重量％エタノール水
溶液について、前記抗菌剤溶液と同様にスタンプ法によ
りその抗菌作用を測定した。結果を表２に示す。For comparison, the antibacterial activity of sterilized water and a 45% by weight aqueous ethanol solution containing no oligogalacturonic acid composition was measured by the stamp method in the same manner as in the above antibacterial agent solution. Table 2 shows the results.
【００３１】[0031]
【表２】 [Table 2]
【００３２】[0032]
【実施例４】 （スポンジケーキへの塗抹による抗菌作用）実施例１で
得られたオリゴガラクツロン酸組成物を、５重量％エタ
ノール溶液中に０．６重量％の割合となるように溶解
し、抗菌剤溶液とした。Example 4 (Antibacterial action by smearing on sponge cake) The oligogalacturonic acid composition obtained in Example 1 was dissolved in a 5% by weight ethanol solution to a ratio of 0.6% by weight, An antimicrobial solution was used.
【００３３】この両抗菌剤溶液について、一般生菌数測
定法（ペトリフィルム法）によりその抗菌作用を評価し
た。すなわち、スポンジケーキ（７×３×５ｃｍ）の全
面に抗菌剤溶液を３ｍｌ塗抹し、１５℃で４日間保存
し、生菌数を測定した。また、対照として、抗菌剤溶液
の代わりにオリゴガラクツロン酸組成物を含まない滅菌
水又は５重量％エタノール溶液を用いた他は同様に操作
したものについて、生菌数を測定して保存性の比較を行
った。結果を表３に示す。The antimicrobial activity of the two antimicrobial solutions was evaluated by a general viable cell count method (Petrifilm method). That is, 3 ml of the antibacterial agent solution was smeared on the entire surface of the sponge cake (7 × 3 × 5 cm), stored at 15 ° C. for 4 days, and the viable cell count was measured. As a control, the number of viable cells was measured and the storage stability was compared for the same operation except that sterilized water or a 5% by weight ethanol solution containing no oligogalacturonic acid composition was used instead of the antibacterial agent solution. Was done. Table 3 shows the results.
【００３４】[0034]
【表３】 [Table 3]
【００３５】[0035]
【実施例５】 （ポテトサラダへの添加による抗菌作用）表４に示す配
合比でポテトサラダを製造した。これを２０℃で保存
し、ペトリフィルム法にて生菌数を測定した。また、対
照としてオリゴガラクツロン酸組成物を添加しなかった
他は同様に製造したポテトサラダについても同様に操作
し、生菌数を測定した。結果を表５に示す。Example 5 (Antibacterial activity by addition to potato salad) Potato salad was produced at the compounding ratio shown in Table 4. This was stored at 20 ° C., and the viable cell count was measured by the Petri film method. As a control, the same procedure was applied to a potato salad similarly prepared except that the oligogalacturonic acid composition was not added, and the viable cell count was measured. Table 5 shows the results.
【００３６】[0036]
【表４】 [Table 4]
【００３７】[0037]
【表５】 [Table 5]
Claims (3)
び２〜１５量体の４，５−不飽和オリゴガラクツロン酸
を含有するオリゴガラクツロン酸含有組成物。An oligogalacturonic acid-containing composition comprising a 6 to 15-mer oligogalacturonic acid and a 2 to 15-mer 4,5-unsaturated oligogalacturonic acid.
した水溶液中において８０〜１００℃に加熱して分子量
１０００〜５０００のオリゴガラクツロン酸及び分子量
３００〜５０００の４，５−不飽和オリゴガラクツロン
酸の混合物を得、次いでペクチナーゼにより酵素反応さ
せることを特徴とする、請求項１記載のオリゴガラクツ
ロン酸組成物の製造方法。2. A pectin is heated to 80 to 100 ° C. in an aqueous solution adjusted to pH 6.5 to 7.2 to produce oligogalacturonic acid having a molecular weight of 1,000 to 5,000 and a 4,5-unsaturated oligogalacturonic acid having a molecular weight of 300 to 5,000. The method for producing an oligogalacturonic acid composition according to claim 1, wherein a mixture of galacturonic acid is obtained, and the mixture is then subjected to an enzymatic reaction with pectinase.
び２〜１５量体の４，５−不飽和オリゴガラクツロン酸
を含有する抗菌性組成物。3. An antibacterial composition containing a 6 to 15-mer oligogalacturonic acid and a 2 to 15-mer 4,5-unsaturated oligogalacturonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3019397A JPH10226701A (en) | 1997-02-14 | 1997-02-14 | Antibacterial composition containing oligoglacturonic acid and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3019397A JPH10226701A (en) | 1997-02-14 | 1997-02-14 | Antibacterial composition containing oligoglacturonic acid and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10226701A true JPH10226701A (en) | 1998-08-25 |
Family
ID=12296926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3019397A Pending JPH10226701A (en) | 1997-02-14 | 1997-02-14 | Antibacterial composition containing oligoglacturonic acid and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH10226701A (en) |
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|---|---|---|---|---|
| EP1207194A1 (en) * | 2000-11-03 | 2002-05-22 | Bernhard Hanke | Cleaning agent additives comprising oligogalacturonides |
| EP1267891A2 (en) * | 2000-02-16 | 2003-01-02 | N.V. Nutricia | Antiadhesive carbohydrates |
| JP2004194634A (en) * | 2002-12-18 | 2004-07-15 | Toho Chem Ind Co Ltd | Method for producing polygalacturonic acid transparently soluble in water |
| JP2007230920A (en) * | 2006-03-01 | 2007-09-13 | Toppan Printing Co Ltd | Antibacterial and antifungal agent |
| FR2916447A1 (en) * | 2007-05-25 | 2008-11-28 | Univ Picardie Jules Verne Etab | PROCESS FOR THE PRODUCTION AND USE OF OLIGOMERIC FAMILIES OF GALACTURONIC ACID |
| WO2010044649A1 (en) * | 2008-10-16 | 2010-04-22 | Martinez Tellez Miguel Angel | Method for controlling colouration in table grapes based on oligogalacturonides |
| JP2019511569A (en) * | 2016-02-22 | 2019-04-25 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | Antimicrobial composition and use thereof |
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-
1997
- 1997-02-14 JP JP3019397A patent/JPH10226701A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7919479B2 (en) * | 2000-02-16 | 2011-04-05 | N. V. Nutricia | Antiadhesive carbohydrates |
| EP1267891A2 (en) * | 2000-02-16 | 2003-01-02 | N.V. Nutricia | Antiadhesive carbohydrates |
| EP1267891B1 (en) * | 2000-02-16 | 2011-07-27 | N.V. Nutricia | Antiadhesive carbohydrates |
| EP2305270A1 (en) * | 2000-02-16 | 2011-04-06 | N.V. Nutricia | Anti-adhesive carbohydrates |
| US7759324B2 (en) * | 2000-02-16 | 2010-07-20 | N.V. Nutricia | Antiadhesive carbohydrates |
| EP2298325A1 (en) * | 2000-02-16 | 2011-03-23 | N.V. Nutricia | Combinations comprising anti-adhesive and prebiotic carbohydrates |
| EP1207194A1 (en) * | 2000-11-03 | 2002-05-22 | Bernhard Hanke | Cleaning agent additives comprising oligogalacturonides |
| JP2004194634A (en) * | 2002-12-18 | 2004-07-15 | Toho Chem Ind Co Ltd | Method for producing polygalacturonic acid transparently soluble in water |
| JP2007230920A (en) * | 2006-03-01 | 2007-09-13 | Toppan Printing Co Ltd | Antibacterial and antifungal agent |
| FR2916447A1 (en) * | 2007-05-25 | 2008-11-28 | Univ Picardie Jules Verne Etab | PROCESS FOR THE PRODUCTION AND USE OF OLIGOMERIC FAMILIES OF GALACTURONIC ACID |
| WO2009004153A1 (en) * | 2007-05-25 | 2009-01-08 | Université de Picardie Jules Verne | Method for producing families of galacturonic acid oligomers and use thereof |
| WO2010044649A1 (en) * | 2008-10-16 | 2010-04-22 | Martinez Tellez Miguel Angel | Method for controlling colouration in table grapes based on oligogalacturonides |
| JP2019511569A (en) * | 2016-02-22 | 2019-04-25 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | Antimicrobial composition and use thereof |
| US11065223B2 (en) | 2016-02-22 | 2021-07-20 | Board Of Regents, The University Of Texas System | Antimicrobial compositions and uses thereof |
| JP2021193130A (en) * | 2016-02-22 | 2021-12-23 | ボード オブ リージェンツ, ザ ユニバーシティ オブ テキサス システムBoard Of Regents, The University Of Texas System | Antimicrobial compositions and uses thereof |
| US11826332B2 (en) | 2016-02-22 | 2023-11-28 | Board Of Regents, The University Of Texas System | Antimicrobial compositions and uses thereof |
| CN115849973A (en) * | 2022-11-28 | 2023-03-28 | 史丹利农业集团股份有限公司 | Preparation method of composite galacturonic acid fertilizer synergist |
| CN115849973B (en) * | 2022-11-28 | 2023-07-18 | 史丹利农业集团股份有限公司 | Preparation method of compound galacturonic acid fertilizer synergist |
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