JPH04148661A - Bitterness elimination of beta-glucooligosaccharide - Google Patents
Bitterness elimination of beta-glucooligosaccharideInfo
- Publication number
- JPH04148661A JPH04148661A JP2271352A JP27135290A JPH04148661A JP H04148661 A JPH04148661 A JP H04148661A JP 2271352 A JP2271352 A JP 2271352A JP 27135290 A JP27135290 A JP 27135290A JP H04148661 A JPH04148661 A JP H04148661A
- Authority
- JP
- Japan
- Prior art keywords
- glucooligosaccharide
- glucose
- beta
- gentiooligosyl
- glucooligosaccharides
- 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.)
- Granted
Links
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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、ダイエタリー甘味料として、あるいは腸内フ
ローラ改善物質として1食品、飲料、医薬品などに使用
できるβ−グルコオリゴ糖の苦味除去法に関する。DETAILED DESCRIPTION OF THE INVENTION "Industrial Application Field" The present invention relates to a method for removing bitterness from β-glucooligosaccharide, which can be used as a dietary sweetener or as an intestinal flora improving substance in foods, beverages, medicines, etc.
「従来の技術」
各種飲食品の製造において、砂糖、水飴、グルコース、
マルトース、異性化糖など各種の糖質が甘味料として使
用されてきた。しかし、これらの糖質は、グルコース又
はグルコースがa−グルコシド結合した糖であり、体内
で分解されてカロリー源となるため、過剰に摂取すると
、肥満を招いたり、糖尿病などの成人病を訪発するとい
う問題があった。また、アスパルテーム等のノンカロリ
ーの合成甘味料も開発されている。しかし1合成甘味料
は、自然物でないことから1人体に対する安全性に不安
があった。"Conventional technology" In the production of various food and drink products, sugar, starch syrup, glucose,
Various carbohydrates such as maltose and high fructose sugar have been used as sweeteners. However, these carbohydrates are glucose or sugars in which glucose is bound to an a-glucoside, and are broken down in the body and become a source of calories, so if consumed in excess, they can lead to obesity and lead to adult diseases such as diabetes. There was a problem. Non-caloric synthetic sweeteners such as aspartame have also been developed. However, since synthetic sweeteners are not natural products, there were concerns about their safety for humans.
一方、近年、腸内におけるフローラ(細菌叢)が人間の
健康と係わりをもっていることが知られ、腸内細菌に対
する関心が高まっている0例えばビフィズス菌は、人間
の腸内フローラを構成する主要な菌種のひとつであり、
例えば腸内の腐敗性細菌や病原菌の生育抑制など、人や
動物に対して種々の有益な生理的役割をはだすことが知
られている。このビフィズス菌は、各種の疾患や加齢に
伴ない減少又は消失するため、腸内のビフィズス菌を増
加させる各種の試みがなされている。On the other hand, in recent years, it has been known that the flora (bacterial flora) in the intestine is related to human health, and interest in intestinal bacteria is increasing. It is one of the bacterial species,
It is known that it plays a variety of beneficial physiological roles in humans and animals, such as inhibiting the growth of putrefactive bacteria and pathogenic bacteria in the intestines. Bifidobacteria decrease or disappear with various diseases and aging, so various attempts have been made to increase the number of Bifidobacteria in the intestines.
このような中で、ビフィズス菌増殖性オリゴ糖が最近脚
光を浴びており、ビフィズス菌増殖効果を有するものと
して、フラクトオリゴ糖、コンニャクオリゴ糖、イソマ
ルトオリゴ糖、ガラクトオリゴ糖などが報告されている
。Under these circumstances, bifidobacteria-proliferating oligosaccharides have recently been in the spotlight, and fructooligosaccharides, konjac oligosaccharides, isomalto-oligosaccharides, galactooligosaccharides, etc. have been reported as having a bifidobacterium-propagating effect.
ところで、β−グルコシド結合からなるグルコオリゴ糖
(以下、β−グルコオリゴ糖という)は、グルコースを
β−1,6結合及び/又はβ−1,4結合させて得られ
る糖質であり、これらのβ−グルコシド結合は、体内酵
素で分解できないため、低カロリーの糖質として利用で
きる。また、本出願人は、これらのβ−グルコオリゴ糖
がビフィズス菌及び乳酸菌に対する増殖促進効果を有し
ていることを見出し、β−グルコオリゴ糖からなる腸内
フローラ改善物質を既に提案している(特願平2−61
935号参照)。By the way, glucooligosaccharides consisting of β-glucoside bonds (hereinafter referred to as β-glucooligosaccharides) are carbohydrates obtained by combining glucose with β-1,6 bonds and/or β-1,4 bonds. - Glucoside bonds cannot be broken down by enzymes in the body, so they can be used as low-calorie carbohydrates. The applicant has also discovered that these β-glucooligosaccharides have a growth-promoting effect on bifidobacteria and lactic acid bacteria, and has already proposed an intestinal flora-improving substance consisting of β-glucooligosaccharides (specifically Ganpei 2-61
(See No. 935).
[発明が解決しようとする課題」
しかしながら、β−グルコオリゴ糖は、特有の苦味を有
しているため、食品等の種類によっては風味に悪影響を
与えるため、適用範囲が限定されるという問題点があっ
た。[Problems to be Solved by the Invention] However, β-glucooligosaccharides have a unique bitter taste, which adversely affects the flavor of some foods, so there is a problem that the scope of application is limited. there were.
したがって、本発明の目的は1食品、飲料及び医薬品に
自由に添加できるようにするため、β−グルコオリゴ糖
の苦味を除去する方法を提供することにある。Therefore, an object of the present invention is to provide a method for removing the bitter taste of β-glucooligosaccharide so that it can be freely added to foods, beverages, and medicines.
[課題を解決するための手段」
本発明者らは、ダイエクリー甘味料及び腸内フローラ改
善物質として有用なβ−グルコオリゴ糖について種々研
究した結果、その還元処理物は苦味が消失し、良好でま
ろやかな甘味を呈することを見出し、本発明を完成する
に至った。[Means for Solving the Problems] The present inventors have conducted various studies on β-glucooligosaccharide useful as a Daiecley sweetener and an intestinal flora improving substance. As a result, the reduced product has lost its bitter taste and has a good and mellow taste. They discovered that it exhibits a sweet taste and completed the present invention.
すなわち、本発明のβ−グルコオリゴ糖の苦味除去法は
、β−グルコオリゴ糖を還元処理することを特徴とする
。That is, the method for removing bitterness from β-glucooligosaccharides of the present invention is characterized by subjecting β-glucooligosaccharides to reduction treatment.
以下1本発明について具体例を挙げて更に詳細に説明す
る。Hereinafter, the present invention will be explained in more detail by giving specific examples.
本発明で用いるβ−グルコオリゴ糖は、種々の微生物起
源のβ−グルコシダーゼをグルコース及び/又はβ−グ
ルコオリゴ糖に作用させ、β−グルコシダーゼが具備す
る縮合・転移作用の極限機能を最大限に発揮させること
により容易に高収率で製造することができる。この方法
については。The β-glucooligosaccharides used in the present invention are produced by allowing β-glucosidases derived from various microorganisms to act on glucose and/or β-glucooligosaccharides to maximize the ultimate functions of condensation and transfer that β-glucosidase possesses. This allows for easy production with high yield. About this method.
先に本発明者らが提案した特開平1−222779号、
特願平1−41289号に詳細に説明されている。Japanese Patent Application Laid-Open No. 1-222779, which was previously proposed by the present inventors,
This is explained in detail in Japanese Patent Application No. 1-41289.
この製造方法の概略を説明すると、β−グルコシダーゼ
としては、各種微生物起源のものを用いることが可能で
あり1例えば、糸状菌のトリコデルマ・ビリデイ(Tr
ichodern+a viridel 、 トリコ
デルマ・リーサイ(Trichoderma rees
eil 、 トリコデルマ・コニンギ−ITricho
derea 眩■用u1.アスペルギルス・ニガー(組
囮l」」山「l、ペニシリウム・フリクエンタンス(P
enicilliumす肥μ匹膓朋)等、木材腐朽菌の
ポリポラス・トウリヒフェリー(匣by佳す捷月且堕旺
鱈)、クリソスポリウム・リグノルム(Chr sos
oriura旦旺肛憇)、 シゾフィラム・コミュー
ン1shizo h flus commune)等、
また、細菌のシュードモナス・フルオレッセンス1Ps
eudo*onasfluorescens var、
cellulosal、セルロモナス°ウダ(Cell
ulomonas udal 、 クロストリデイウム
・サーモセラム(Clostridium therm
ocelluml 、ルミノコッカス・アルバスfRu
minococcus albusl等の微生物起源の
酵素が好ましく用いられる。これらの微生物は、いずれ
も公知のものであり、容易に入手し、酵素を調製するこ
とができる。To give an overview of this production method, it is possible to use β-glucosidase derived from various microorganisms.1 For example, the filamentous fungus Trichoderma viridii (Tr
ichodern+a viridel, Trichoderma rees
eil, Trichoderma coningii-ITricho
derea dazzling u1. Aspergillus niger (P.
wood-decaying fungi such as Polyporus turihiferii (enicillium), Chrysosporium lignorum (Chr sos), etc.
oriura danwanganki), Schizophyllum commune 1shizo h flus commune), etc.
In addition, the bacteria Pseudomonas fluorescens 1Ps
eudo*onasfluorescens var,
cellulosal, Cellulomonas uda (Cell
ulomonas udal, Clostridium thermocellum
ocelluml, Ruminococcus albus fRu
Enzymes originating from microorganisms such as minococcus albusl are preferably used. All of these microorganisms are known and can be easily obtained and enzymes can be prepared from them.
また、基質としては、D−グルコース及び/又はβ−グ
ルコオリゴ糖が用いられる。ここで、基質となるβ−グ
ルコオリゴ糖は、セロビオース、ゲンチオビオース、あ
るいはそれ以上の重合度のゲンチオオリゴ糖などを意味
している。基質としてβ−グルコオリゴ糖を用いた場合
には、本酵素反応によってより高重合度のβ−グルコオ
リゴ糖を得ることができる。特に好ましくは、基質とし
てグルコース、セロビオース、ゲンチオビオースから選
ばれた少なくとも一種が用いられる。Moreover, D-glucose and/or β-glucooligosaccharide are used as the substrate. Here, the β-glucooligosaccharide used as a substrate means cellobiose, gentiobiose, or gentiooligosaccharide with a higher degree of polymerization. When β-glucooligosaccharide is used as a substrate, β-glucooligosaccharide with a higher degree of polymerization can be obtained by this enzymatic reaction. Particularly preferably, at least one selected from glucose, cellobiose, and gentiobiose is used as the substrate.
こうしてβ−グルコシダーゼをグルコース及び/又はβ
−グルコオリゴ糖に作用させると、反応生成物として、
セロビオース、ゲンチオビオース、4−0−β−D−ゲ
ンチオリゴシルーD−グルコース、6−0−β−D−ゲ
ンチオオリゴシル−〇−グルコースなどの各種β−グル
コオリゴ糖が得られる。ここで、4−0−β−〇−ゲン
チオリゴシルー〇−グルコースとは、4−0−β−D−
ゲンチオビオシルー〇−グルコース、4−0−β−D−
ゲンチオトリオシルーD−グルコースあるいはそれ以上
の重合度のものを意味する。また、6−0−β−D−ゲ
ンチオオリゴシル−〇−グルコースとは、6−0−β−
〇−ゲンチオビオシルーD−グルコース(ゲンチオトリ
オース) 、 6−0−β−D−ゲンチオトリオシルー
D−グルコース(ゲンチオテトラオース)あるいはそれ
以上の重合度のゲンチオオリゴ糖を意味する。In this way, β-glucosidase can be converted into glucose and/or β-glucosidase.
-When acting on glucooligosaccharide, as a reaction product,
Various β-glucooligosaccharides such as cellobiose, gentiobiose, 4-0-β-D-gentioligosyl-D-glucose, and 6-0-β-D-gentiooligosyl-〇-glucose are obtained. Here, 4-0-β-〇-gentioligosyl-〇-glucose means 4-0-β-D-
Genthiobiosyl-glucose, 4-0-β-D-
It means gentiotriosyl-D-glucose or one with a higher degree of polymerization. In addition, 6-0-β-D-gentiooligosyl-〇-glucose means 6-0-β-
〇-Genthiobiosyl-D-glucose (gentiotriose), 6-0-β-D-gentiotriosyl-D-glucose (gentiotetraose) or a gentio-oligosaccharide with a higher degree of polymerization.
これらの反応生成物は、使用する酵素によっても変化す
るが、基質としてグルコースやセロビオースを用いた場
合には、上記各種のβ−グルコオリゴ糖が何種類か混在
して生成されやすい傾向がある。また、基質としてゲン
チオビオースを用いた場合には、反応生成物として、6
−0−β−〇−ゲンチオビオシルーD−グルコース、6
−0−β−D−ゲンチオトリオシルーD−グルコースな
とのゲンチオオリゴ糖のみが生成されやすい傾向がある
。These reaction products vary depending on the enzyme used, but when glucose or cellobiose is used as a substrate, there is a tendency for a mixture of several types of the above-mentioned β-glucooligosaccharides to be produced. In addition, when gentiobiose is used as a substrate, 6
-0-β-〇-gentiobiosyl-D-glucose, 6
Only gentiooligosaccharides such as -0-β-D-gentiotriosyl-D-glucose tend to be produced.
なお、酵素反応条件について説明すると、基質濃度は、
特に限定されないが、通常1〜90%(固形量/容積)
が好ましく、5〜80%(固形量/容積)が更に好まし
い、また、基質に対する酵素濃度は、高ければ高いほど
良いが、通常、基質1g当りIDDggJU上使用する
ことが好ましい0反応温度及び反応pl(は、使用酵素
の最適反応条件下で行えばよい6通常、反応温度は、3
0〜80℃が好ましく、50〜70℃がより好ましい0
反応pHは3〜8程度が好ましい。反応時間は、目的と
するβ−グルコオリゴ糖が十分生成・蓄積される時間と
すればよいが1通常、2分から72時間程度が適当であ
る0反応の方法は、基質に酵素を添加して行^ばよく、
あるいは酵素を適当な固定化剤に吸着させて固定化酵素
とし、この固定化酵素を用いる連続反応方式で行っても
よい、なお、こうして得られた反応生成物を更に各種の
方法で分画して、各種のβ−グルコオリゴ糖をそれぞれ
分離・精製することもできる。In addition, to explain the enzyme reaction conditions, the substrate concentration is
Although not particularly limited, usually 1 to 90% (solid amount/volume)
is preferable, and 5 to 80% (solid amount/volume) is more preferable.Also, the higher the enzyme concentration with respect to the substrate, the better, but it is usually preferable to use 0 reaction temperature and reaction pl per 1 g of substrate. (This can be carried out under the optimum reaction conditions for the enzyme used.) Usually, the reaction temperature is 3.
0 to 80°C is preferable, and 50 to 70°C is more preferable.
The reaction pH is preferably about 3 to 8. The reaction time may be set to the time required for the desired β-glucooligosaccharide to be sufficiently produced and accumulated.1 Normally, the appropriate time is about 2 minutes to 72 hours.The reaction method is carried out by adding an enzyme to the substrate. ^Good,
Alternatively, the enzyme may be adsorbed onto a suitable immobilizing agent to obtain an immobilized enzyme, and the reaction may be carried out in a continuous reaction using this immobilized enzyme.The reaction product thus obtained may be further fractionated by various methods. It is also possible to separate and purify various β-glucooligosaccharides.
本発明では、上記のようにして得られたβ−グルコオリ
ゴ糖を還元処理する。還元処理は、糖アルコールの製造
などにおいて従来より採用されている接触還元(水添)
法が採用される6例えば。In the present invention, the β-glucooligosaccharide obtained as described above is subjected to a reduction treatment. The reduction process is catalytic reduction (hydrogenation), which has traditionally been used in the production of sugar alcohols.
The law is adopted 6 e.g.
β−グルコオリゴ糖の40〜60重量%濃度の水溶液を
調製し、この水溶液に、例えばラネー・ニッケル、白金
カーボン、ルテニウム・カーボン、パラジウム・カーボ
ン等の金属の還元触媒を添加する。そして、水素圧力を
50〜200 Kg/cm’とし、温度80〜170℃
の条件下で、30分〜数時間攪拌して反応させる0反応
終了後は、例えば活性炭を加えて触媒を除き、更にイオ
ン交換樹脂を通して脱塩し、必要に応じて濃縮又は乾燥
してβ−グルコオリゴ糖の還元処理物を得ることができ
る。An aqueous solution of β-glucooligosaccharide having a concentration of 40 to 60% by weight is prepared, and a metal reduction catalyst such as Raney nickel, platinum carbon, ruthenium carbon, palladium carbon, etc. is added to this aqueous solution. Then, the hydrogen pressure was set to 50 to 200 Kg/cm', and the temperature was set to 80 to 170°C.
After the reaction is complete, add activated carbon to remove the catalyst, pass through an ion exchange resin to desalt, and if necessary concentrate or dry the β- A reduced product of glucooligosaccharide can be obtained.
こうして得られたβ−グルコオリゴ糖の還元処理物は、
β−グルコオリゴ糖に特有な苦味が消失し、まろやかな
甘味を呈している。したがって。The reduced product of β-glucooligosaccharide obtained in this way is
The bitterness characteristic of β-glucooligosaccharides has disappeared, and the product has a mellow sweetness. therefore.
ダイエタリー甘味料として各種の食品、医薬品に使用で
き、保湿性に富むことから食品の保湿剤の他、結晶防止
剤、照り、ボディなどの付与剤などとしても有効に利用
できる。更に、β−グルコオリゴ糖の還元処理物は、ビ
フィズス菌及び乳酸菌に対する増殖促進効果を有してお
り、腸内フローラ改善作用をもたらす健康食品用機能性
糖質としても利用できる。It can be used as a dietary sweetener in various foods and medicines, and because of its high moisturizing properties, it can be effectively used as a moisturizer for foods, as well as a crystallization inhibitor, and a shine and body-imparting agent. Furthermore, the reduced product of β-glucooligosaccharide has a growth-promoting effect on bifidobacteria and lactic acid bacteria, and can also be used as a functional carbohydrate for health foods that improves intestinal flora.
なお、β−グルコオリゴ糖の還元処理物を食品や医薬品
に甘味料として添加する場合、甘味がやや不足するとき
は、他の甘味料、例えばスクロース、水飴、ブドウ糖、
マルトース、異性化糖、蜂蜜、ソルビトール、マルチト
ール、ラクチトール、L−アスパラチルフェニルアラニ
ンメチルエステル(アスパルテーム)、サッカリン、グ
リチルリチン、ステビオシトなどから選ばれた少なくと
も一種と併用してもよい。When adding the reduced product of β-glucooligosaccharide as a sweetener to foods or medicines, if the sweetness is slightly insufficient, other sweeteners such as sucrose, starch syrup, glucose, etc.
It may be used in combination with at least one selected from maltose, high fructose sugar, honey, sorbitol, maltitol, lactitol, L-asparatylphenylalanine methyl ester (aspartame), saccharin, glycyrrhizin, steviocyto, and the like.
β−グルコオリゴ糖の還元処理物は1M味、塩から味、
渋味、旨味などの他の呈味な有する各種の物質とよく調
和するので1例えば醤油、味噌、マヨネーズ、ドレッシ
ング、食酢、中華の素、天つゆ、ソース、ケチャツプ、
焼肉のタレ、カレールウ−、シチューの素、スープの素
、ダシの素。The reduced β-glucooligosaccharide has a 1M taste, a salty taste,
It blends well with various substances that have other tastes such as astringency and umami, so for example, soy sauce, miso, mayonnaise, dressing, vinegar, Chinese food, tempura soup, sauce, ketchup, etc.
Yakiniku sauce, curry roux, stew base, soup base, dashi base.
複合調味料、みりんなどの各種の調味料に使用できる。Can be used in various seasonings such as compound seasonings and mirin.
また、せんべい、あられ、餅類、まんじゅう、ついろう
、あん類、羊餐、ゼリー、カステラ、飴玉などの各種和
菓子、パン、ビスケット、クラッカー、クツキー、パイ
、プリン、パタークリーム、シュークリーム、スポンジ
ケーキ、ドーナツ、チョコレート、チューインガム、キ
ャラメル、ハードキャンデイ−などの各種洋菓子、アイ
スクリーム、シャーベットなどの氷菓子、果実のシロッ
プ漬、水密などのシロップ類、フラワーペースト、ビー
ナツツペースト、フラーペーストなどのペースト類、ジ
ャム、マーマレード、シロップ漬、糖果などの果実加工
品、福神漬、千枚漬、らっきょう清などの漬物類、ハム
、ソーセージなどの畜肉製品類、かまぼこ、竹輪などの
魚肉製品、各種珍味郭、佃煮類の他、ビール、リキュー
ル、酒等のアルコール飲料類、コーヒーココア、ジュー
ス、炭酸飲料、スタミナドリンク、乳酸飲料、乳酸菌飲
料などの清涼飲料水、インスタントジュース、インスタ
ントコーヒーなどの即席飲食品などの各種飲食物、嗜好
品にも使用できる。In addition, various Japanese sweets such as rice crackers, arare, rice cakes, manju, tsuiro, red bean paste, sheep's meal, jelly, castella, hard candy, bread, biscuits, crackers, kutsky, pies, pudding, putter cream, cream puffs, and sponge cakes. , various Western sweets such as donuts, chocolate, chewing gum, caramel, and hard candies; frozen confections such as ice cream and sorbet; syrups such as fruit pickled in syrup and watertight; pastes such as flower paste, peanut paste, and fuller paste. , processed fruit products such as jam, marmalade, syrup pickles, sugar fruit, pickles such as fukujinzuke, senmaizuke, and rakkyosei, meat products such as ham and sausage, fish products such as kamaboko and chikuwa, various delicacies, and tsukudani. In addition, various foods and drinks such as alcoholic beverages such as beer, liqueur, and alcohol, soft drinks such as coffee cocoa, juice, carbonated drinks, stamina drinks, lactic acid drinks, and lactic acid bacteria drinks, and instant food and drinks such as instant juice and instant coffee. It can also be used as a luxury item.
更に、β−グルコオリゴ糖の還元処理物を、他の生理活
性物質1例えば食物繊維、乳酸菌、ビフィズス菌、ビタ
ミン類などと混合して、健康食品、医薬品などとしても
よい、その他、飼料、餌料、化粧品など経口使用するも
の全般に添加することができる。Furthermore, the reduced product of β-glucooligosaccharide may be mixed with other physiologically active substances such as dietary fiber, lactic acid bacteria, bifidobacteria, vitamins, etc. to be used as health foods, medicines, etc. In addition, it can be used as feed, food, etc. It can be added to all products for oral use such as cosmetics.
なお、各種食品、飲料、医薬品等の原料へのβ−グルコ
オリゴ糖の還元処理物の添加量は、特に限定されないが
、0.5〜50重量%とすることが好ましく、1.0〜
30重量%とすることが更に好ましい。Note that the amount of the reduced β-glucooligosaccharide added to raw materials for various foods, beverages, pharmaceuticals, etc. is not particularly limited, but it is preferably 0.5 to 50% by weight, and 1.0 to 50% by weight.
More preferably, the content is 30% by weight.
「作用及び効果」
本発明によれば、β−グルコオリゴ糖を還元処理するこ
とにより、β−グルコオリゴ糖の苦味を消失させて、ま
ろやかな甘味を付与することができる。この還元処理物
は、β−グルコオリゴ糖と同様に、ダイエタリー甘味料
、腸内フローラ改善物質としての効果を有している。し
たがって、各種の食品や医薬品の材料として幅広く使用
でき。"Action and Effect" According to the present invention, by reducing the β-glucooligosaccharide, the bitter taste of the β-glucooligosaccharide can be eliminated and a mellow sweetness can be imparted. This reduced product has effects as a dietary sweetener and an intestinal flora improving substance, similar to β-glucooligosaccharide. Therefore, it can be widely used as a material for various foods and medicines.
ダイエタリー甘味料、腸内フローラ改善物質としての効
果を付与することができる。It can provide effects as a dietary sweetener and an intestinal flora improving substance.
「実施例」 以下に1本発明を実施例で詳細に説明する。"Example" The present invention will be explained in detail below using examples.
実施例1
fイ)D−グルコース300 gに、トリコデルマ・ビ
リデ4 (Trichoderwa viridel起
源の粗セルラーゼ製剤「メイセラーゼ」 (商品名、明
治製菓■製)より精製して調製したβ−グルコシダーゼ
を、 5.8 XIG’単位(500■l)添加しくグ
ルコース約60%、 w/vl、 pH5,0、温度6
0℃で48時間反応を行った0反応終了後、100℃で
5分間加熱処理して反応を停止させ、常法により活性炭
脱色、脱イオン精製した後、同好5分72%1m/II
まで減圧濃縮した。得られた濃縮液の糖組成を高速液
体クロマトグラフィーで分析した結果を第1表に示す。Example 1 f) To 300 g of D-glucose, β-glucosidase purified from a crude cellulase preparation "Meicelase" (trade name, manufactured by Meiji Seika Co., Ltd.) originating from Trichoderma viride 4 was added.5. 8 XIG' units (500 μl) added glucose approx. 60%, w/vl, pH 5.0, temperature 6
After the reaction was completed at 0°C for 48 hours, the reaction was stopped by heat treatment at 100°C for 5 minutes, and after decolorizing and deionizing with activated carbon by a conventional method, the mixture was heated for 5 minutes at 72% 1m/II.
The mixture was concentrated under reduced pressure. Table 1 shows the results of analyzing the sugar composition of the obtained concentrate by high performance liquid chromatography.
なお、高速液体クロマトグラフィーの分析条件は、下記
の通りである。The analysis conditions for high performance liquid chromatography are as follows.
カラム:島津製作所製5CR−101
検出器:示差屈折計
カラム温度:55℃
カラム流速; 0.8 ml/win
(ロ)次いで、(イ)で得られた反応生成糖液を、内径
2 cm 、長さ 120 craのジャケット付(6
0℃)カラムにカチオン交換樹脂rDowex 99J
(Na’″型、ダウケミカル社製)を充填した後、樹脂
量当り5〜7%(v/v)の固形分量となるように上記
糖液な負荷し、空間速度(SV、hr−’)0.35で
分画し、ゲンチオオリゴ糖画分を集めた。この両分の糖
組成を第1表に示す、収率はゲンチオオリゴ糖含有量の
98%が回収され、本操作を10回繰り返して約40
g のゲンチオオリゴ糖を得た。これを凍結乾燥して
粉末化した。Column: 5CR-101 manufactured by Shimadzu Corporation Detector: Differential refractometer Column temperature: 55°C Column flow rate: 0.8 ml/win (b) Next, the reaction product sugar solution obtained in (a) was poured into a tube with an inner diameter of 2 cm, With jacket of length 120 cr (6
0°C) Column with cation exchange resin rDowex 99J
(Na''' type, manufactured by Dow Chemical Company), the above sugar solution was loaded to a solid content of 5 to 7% (v/v) based on the amount of resin, and the space velocity (SV, hr-' ) 0.35, and the gentio-oligosaccharide fraction was collected. The sugar composition of both of these fractions is shown in Table 1. The yield was 98% of the gentio-oligosaccharide content, and this operation was repeated 10 times. About 40
g of gentio-oligosaccharide was obtained. This was freeze-dried and powdered.
(以下、余白)
第1表
(ハ)上記のようにして得られたβ−グルコオリゴ糖含
量が80%以上であるオリゴ糖シロップ(固形分50%
)200−βを、500■β容のオートクレーブに仕込
み、ラネー・ニッケル触媒12gを展開して加え、フラ
ンジを閉めた後、常温で、圧力120kg/cl1mに
達するまで水素を充填する0次いで、700回/分の速
度で撹拌しながら、温度を上げ、130℃で4時間反応
させた後、放冷し、反応液を取り出した。この反応液に
、活性炭2gを加えて撹拌し、濾過した後、イオン交換
樹脂で脱塩して還元処理したβ−グルコオリゴ糖を得た
。(Hereinafter, blank space) Table 1 (c) Oligosaccharide syrup with a β-glucooligosaccharide content of 80% or more obtained as described above (solid content 50%)
) 200-β into a 500 μ β volume autoclave, expand and add 12 g of Raney nickel catalyst, close the flange, and then fill with hydrogen at room temperature until the pressure reaches 120 kg/cl1m. The temperature was raised while stirring at a rate of 130° C. for 4 hours, the mixture was allowed to cool, and the reaction solution was taken out. To this reaction solution, 2 g of activated carbon was added, stirred, filtered, and then desalted with an ion exchange resin to obtain a reduced β-glucooligosaccharide.
この還元処理物の水素添加率を求めるため、還元処理前
と処理後のオリゴ糖液の還元糖量を、ソモギーネルソン
法により測定した結果、99.4%が還元されていた。In order to determine the hydrogenation rate of this reduced product, the amount of reducing sugar in the oligosaccharide solution before and after the reduction treatment was measured by the Somogyi-Nelson method, and as a result, 99.4% was reduced.
還元処理前と処理後のオリゴ糖液について、7名の経験
豊かなパネラ−により官能試験を行なった。糖液濃度は
5.0.0.1.0.05.0.025.0.005%
とし、苦いと感じた人の人数により判定した。A sensory test was conducted on the oligosaccharide solution before and after the reduction treatment by seven experienced panelists. Sugar solution concentration is 5.0.0.1.0.05.0.025.0.005%
Judgment was made based on the number of people who found it bitter.
その結果を第2表に示す。The results are shown in Table 2.
第2表
以上の結果から、試験した濃度において、還元処理後の
糖液に、苦味を感じた人はなく、β−グルコオリゴ糖の
還元処理物は、苦味が除去されていることがわかる。From the results in Table 2 and above, it can be seen that at the tested concentrations, no one felt bitterness in the sugar solution after reduction treatment, and it can be seen that bitterness has been removed from the reduction treatment product of β-glucooligosaccharide.
実施例2
実施例1の(ハ)におけるオリゴ糖シロップをβ−グル
コオリゴ糖含量が45%以上のオリゴ糖シロップ(固形
分50%) 200sβに代え、後は実施例1と同様に
してβ−グルコオリゴ糖の還元処理物を得た。この還元
処理物について、実施例1と同様に水素添加率を測定し
たところ、99.1%が還元されていた。この還元処理
物も苦味が消失していて良好な味覚を有するものであっ
た。Example 2 The oligosaccharide syrup in (c) of Example 1 was replaced with oligosaccharide syrup having a β-glucooligosaccharide content of 45% or more (solid content 50%) 200sβ, and the rest was carried out in the same manner as in Example 1 to prepare β-glucooligosaccharide. A reduced sugar product was obtained. When the hydrogenation rate of this reduced product was measured in the same manner as in Example 1, it was found that 99.1% was reduced. This reduced product also had no bitter taste and had a good taste.
実施例3(ハードキャンデイ−の製造)50%スクロー
ス水溶液500 g+1に、実施例1の(ハ)で得たβ
−グルコオリゴ糖の還元処理物を含有するシラツブを1
00 g加熱溶解させ、次いで減圧下で水分が2%以下
になるまで加熱濃縮し、これにクエン酸5g及び少量の
レモン香料と着色料を混和し、常法に従って成形し、ハ
ードキャンデイ−を得た。Example 3 (Manufacture of hard candy) β obtained in Example 1 (c) was added to 500 g+1 of 50% sucrose aqueous solution.
- 1 piece of Shirabu containing reduced glucooligosaccharide
00 g was heated and dissolved, and then heated and concentrated under reduced pressure until the water content was 2% or less. 5 g of citric acid and a small amount of lemon flavor and coloring were mixed with this and molded according to a conventional method to obtain a hard candy. Ta.
本島は、苦味のない良好な味覚を有するハードキャンデ
イ−であった。Honjima was a hard candy with good taste and no bitterness.
実施例4(ゼリーの製造)
ゼラチン36g、上白1!!84g、実施例2で調製し
たβ−グルコオリゴ糖の還元処理物を含有するシラツブ
を28g、ワイン420 g 、水413 gを用いて
常法によりゼリーを調製した。すなわち、あらかじめ配
合量の172の水でゼラチンを膨潤させておき、残りの
水に上白糖と上記シラツブを加えて加熱・溶解して沸騰
させ、これに膨潤ゼラチンを加えて再び沸騰させる。こ
の溶液を氷水で冷却し、50℃に至った時にワインを加
え、更に冷却して粘りが出はじめたらカップに分注し、
フタをして5℃の冷蔵庫で凝固させて製品とした。Example 4 (manufacture of jelly) 36 g of gelatin, 1 piece of jojiro! ! A jelly was prepared by a conventional method using 84 g of the reduced β-glucooligosaccharide prepared in Example 2, 28 g of Shirabu containing the reduced product of β-glucooligosaccharide, 420 g of wine, and 413 g of water. That is, gelatin is swollen in advance with a blended amount of 172 water, and caster sugar and the above-mentioned Shirabu are added to the remaining water, heated and dissolved to bring it to a boil, and the swollen gelatin is added to this and brought to a boil again. Cool this solution with ice water, add wine when it reaches 50℃, cool it further, and when it starts to thicken, dispense it into cups.
The product was covered with a lid and solidified in a refrigerator at 5°C.
本島はほどよい甘さで、高級な味覚を呈してい特許出願
人 日本食品化工株式会社同代理人 弁理士
松 井 茂Honjima has just the right amount of sweetness and has a luxurious taste.Patent applicant: Nihon Shokuhin Kako Co., Ltd. Patent attorney
Shigeru Matsui
Claims (5)
するβ−グルコオリゴ糖の苦味除去法。(1) A method for removing bitterness from β-glucooligosaccharides, which comprises subjecting β-glucooligosaccharides to a reduction treatment.
ォロース、ラミナリビオース、ゲンチオビオース、4−
¥O¥−β−¥D¥−ゲンチオオリゴシル−¥D¥−グ
ルコース及び6−¥O¥−β−¥D¥−ゲンチオオリゴ
シル−¥D¥−グルコースからなる群より選ばれた少な
くとも一種である特許請求の範囲第1項記載のβ−グル
コオリゴ糖の苦味除去法。(2) The β-glucooligosaccharide is cellobiose, sophorose, laminaribiose, gentiobiose, 4-
selected from the group consisting of ¥O¥-β-¥D¥-gentiooligosyl-¥D¥-glucose and 6-¥O¥-β-¥D¥-gentiooligosyl-¥D¥-glucose A method for removing bitterness from at least one type of β-glucooligosaccharide according to claim 1.
ル−¥D¥−グルコースが、4−¥O¥−β−¥D¥−
ゲンチオオリゴシル−¥D¥−グルコース、4−¥O¥
−β−¥D¥−ゲンチオオリゴシル−¥D¥−グルコー
ス及びそれ以上の重合度のものであり、前記6−¥O¥
−β−¥D¥−ゲンチオオリゴシル−¥D¥−グルコー
スが、6−¥O¥−β−¥D¥−ゲンチオオリゴシル−
¥D¥−グルコース(ゲンチオトリオース)、6−¥O
¥−β−¥D¥−ゲンチトリオシル−¥D¥−グルコー
ス(ゲンチオテトラオース)及びそれ以上の重合度のも
のである特許請求の範囲第2項記載のβ−グルコオリゴ
糖の苦味除去法。(3) The above 4-\O\-β-\D\-gentiooligosyl-\D\-glucose is 4-\O\-β-\D\-
Genthiooligosyl-¥D¥-glucose, 4-¥O¥
-β-¥D¥-gentiooligosyl-¥D¥-glucose and those with a higher degree of polymerization, the above-mentioned 6-¥O¥
-β-\D\-gentiooligosyl-\D\-glucose is 6-\O\-β-\D\-gentiooligosyl-
¥D¥-glucose (gentiotriose), 6-¥O
¥-β-¥D¥-gentytriosyl-¥D¥-glucose (gentiotetraose) and a method for removing bitterness from β-glucooligosaccharide according to claim 2, which has a higher degree of polymerization .
触媒を添加し、水素圧力50〜200kg/cm^2、
温度80〜170℃の条件下で、前記還元処理を行なう
特許請求の範囲第1〜3項のいずれか一つに記載のβ−
グルコオリゴ糖の苦味除去法。(4) Adding a reduction catalyst to the aqueous solution containing the β-glucooligosaccharide and hydrogen pressure of 50 to 200 kg/cm^2,
β- according to any one of claims 1 to 3, wherein the reduction treatment is performed at a temperature of 80 to 170°C.
Method for removing bitterness from glucooligosaccharides.
ーボン、ルテニウム・カーボン、パラジウム・カーボン
から選ばれた少なくとも一種を用いる特許請求の範囲第
4項記載のβ−グルコオリゴ糖の苦味除去法。(5) The method for removing bitterness from β-glucooligosaccharide according to claim 4, wherein the reduction catalyst is at least one selected from Raney nickel, platinum carbon, ruthenium carbon, and palladium carbon.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2271352A JP3020583B2 (en) | 1990-10-09 | 1990-10-09 | Method for removing bitterness of β-glucooligosaccharide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2271352A JP3020583B2 (en) | 1990-10-09 | 1990-10-09 | Method for removing bitterness of β-glucooligosaccharide |
Publications (2)
Publication Number | Publication Date |
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JPH04148661A true JPH04148661A (en) | 1992-05-21 |
JP3020583B2 JP3020583B2 (en) | 2000-03-15 |
Family
ID=17498874
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2271352A Expired - Lifetime JP3020583B2 (en) | 1990-10-09 | 1990-10-09 | Method for removing bitterness of β-glucooligosaccharide |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999036442A1 (en) * | 1998-01-20 | 1999-07-22 | Grain Processing Corporation | Reduced malto-oligosaccharides |
US6475979B2 (en) | 1999-10-20 | 2002-11-05 | Grain Processing Corporation | Reduced malto-oligosaccharide cleansing compositions |
US6610672B2 (en) | 1999-10-20 | 2003-08-26 | Grain Processing Corporation | Compositions including reduced malto-oligosaccharide preserving agents, and methods for preserving a material |
US6720418B2 (en) | 1999-08-20 | 2004-04-13 | Grain Processing Corporation | Derivatized reduced malto-oligosaccharides |
US6919446B1 (en) | 1998-01-20 | 2005-07-19 | Grain Processing Corp. | Reduced malto-oligosaccharides |
-
1990
- 1990-10-09 JP JP2271352A patent/JP3020583B2/en not_active Expired - Lifetime
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999036442A1 (en) * | 1998-01-20 | 1999-07-22 | Grain Processing Corporation | Reduced malto-oligosaccharides |
US6613898B1 (en) | 1998-01-20 | 2003-09-02 | Grain Processing Corporation | Reduced malto-oligosaccharides |
US6919446B1 (en) | 1998-01-20 | 2005-07-19 | Grain Processing Corp. | Reduced malto-oligosaccharides |
US7405293B1 (en) | 1998-01-20 | 2008-07-29 | Grain Processing Corporation | Reduced malto-oligosaccharides |
US7595393B2 (en) | 1998-01-20 | 2009-09-29 | Grain Processing Corporation | Reduced malto-oligosaccharides |
US6720418B2 (en) | 1999-08-20 | 2004-04-13 | Grain Processing Corporation | Derivatized reduced malto-oligosaccharides |
US6475979B2 (en) | 1999-10-20 | 2002-11-05 | Grain Processing Corporation | Reduced malto-oligosaccharide cleansing compositions |
US6610672B2 (en) | 1999-10-20 | 2003-08-26 | Grain Processing Corporation | Compositions including reduced malto-oligosaccharide preserving agents, and methods for preserving a material |
Also Published As
Publication number | Publication date |
---|---|
JP3020583B2 (en) | 2000-03-15 |
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