JPH02219585A - Reaction of starch substance and preparation and use of reaction product thereof - Google Patents
Reaction of starch substance and preparation and use of reaction product thereofInfo
- Publication number
- JPH02219585A JPH02219585A JP1336707A JP33670789A JPH02219585A JP H02219585 A JPH02219585 A JP H02219585A JP 1336707 A JP1336707 A JP 1336707A JP 33670789 A JP33670789 A JP 33670789A JP H02219585 A JPH02219585 A JP H02219585A
- Authority
- JP
- Japan
- Prior art keywords
- starch
- glycyrrhizin
- glycosylglycyrrhizin
- product
- products
- 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
- 229920002472 Starch Polymers 0.000 title claims abstract description 79
- 239000008107 starch Substances 0.000 title claims abstract description 79
- 235000019698 starch Nutrition 0.000 title claims abstract description 79
- 239000000126 substance Substances 0.000 title claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 title description 20
- 238000002360 preparation method Methods 0.000 title description 6
- 239000007795 chemical reaction product Substances 0.000 title description 2
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- 229960004949 glycyrrhizic acid Drugs 0.000 claims abstract description 64
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims abstract description 64
- 235000019410 glycyrrhizin Nutrition 0.000 claims abstract description 64
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims abstract description 64
- 239000004378 Glycyrrhizin Substances 0.000 claims abstract description 63
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 40
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- 239000007787 solid Substances 0.000 claims abstract description 11
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 29
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 claims description 21
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- 239000003463 adsorbent Substances 0.000 description 7
- 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 description 7
- 235000019688 fish Nutrition 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 6
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- 238000009835 boiling Methods 0.000 description 5
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- 150000003839 salts Chemical class 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YBHQCJILTOVLHD-YVMONPNESA-N Mirin Chemical compound S1C(N)=NC(=O)\C1=C\C1=CC=C(O)C=C1 YBHQCJILTOVLHD-YVMONPNESA-N 0.000 description 4
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- 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 description 2
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Abstract
Description
【発明の詳細な説明】
本発明は、澱粉質の反応方法とその反応物の製造方法並
びに用途に関し、更に詳細には、澱粉質とともにグリチ
ルリチンを含有する水溶液にシクロデキストリン・グル
カノトランスフェラーゼ(Cyclodextrin
glucanotransferase、 EC2,4
゜1.19)を作用させることを特徴とする澱粉質の反
応方法、および、該作用により生成される反応生酸物を
採取することを特徴とする澱粉部分分解物およびα−グ
リコシルグリチルリチン含有製品の製造方法、並びに、
該作用により得られる澱粉部分分解物およびα−グリコ
シルグリチルリチン含有製品を含有せしめることを特徴
とする飲食物の製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for reacting starch, a method for producing the reactant, and its uses.
glucanotransferase, EC2,4
゜1.19) A starch reaction method, and a starch partial decomposition product and α-glycosylglycyrrhizin-containing product, characterized in that a reaction product acid produced by the action is collected. A manufacturing method, and
The present invention relates to a method for producing a food or drink, characterized in that it contains a starch partial decomposition product obtained by this action and a product containing α-glycosylglycyrrhizin.
シクロデキストリン・グルカノトランスフェラーゼは、
澱粉質からシクロデキストリンを生成する糖転移酵素と
して古くから知られている。Cyclodextrin glucanotransferase is
It has long been known as a glycosyltransferase that generates cyclodextrin from starch.
近年、澱粉質にシクロデキストリン・グルカノトランス
フェラーゼを作用させて、工業的にシクロデキストリン
が製造されるようになってきた。In recent years, cyclodextrin has been industrially produced by allowing cyclodextrin glucanotransferase to act on starch.
本発明は、澱粉質とともにグリチルリチンを含有する水
溶液にシクロデキストリン・グルカノトランスフェラー
ゼを作用とせようとするものである。The present invention aims to cause cyclodextrin glucanotransferase to act on an aqueous solution containing glycyrrhizin as well as starch.
グリチルリチン(G Iycyrrh iz in )
は、豆科の多年生植物甘草(Licorice) 、(
Glycyrrhiza glabraLinn4 v
ar、 glandulifera Regal et
Herder、 Glycyrrhtza ural
ensis Fishey)の根およびストロン(st
olon)を水抽出して製造される甘味物質で、古来よ
り甘味料、医薬品などとして広く利用され、その構造は
、次式に示すグリチルリチンrm (Glyrrhiz
ic acid)又はその塩である。Glycyrrhizin (GIycyrrhizin)
Licorice is a perennial plant of the legume family.
Glycyrrhiza glabraLinn4 v
ar, glandulifera Regal et.
Herder, Glycyrrhtza ural
ensis Fishey) roots and stolons (st
Glyrrhizin rm (Glyrrhiz
ic acid) or its salts.
グリチルリチンは、砂糖などの糖類甘味料と比較して一
般に次の欠点を有している。Glycyrrhizin generally has the following disadvantages compared to sugar sweeteners such as sugar.
(1)甘味以外に苦味、渋味、えぐ昧などの嫌味や、薬
品臭を有しており、そのままでは列置甘味を楽しめるも
のではない。(1) In addition to sweetness, it has unpleasant tastes such as bitterness, astringency, and acridity, as well as a chemical odor, and it is not possible to enjoy the sweetness as it is.
(2)甘味が砂糖よりもはるかに遅れて現れ、その甘味
が前記の嫌味とともに後味として長(尾を引き、不快感
を与える。(2) Sweetness appears much later than sugar, and the sweetness, along with the aforementioned unpleasantness, lingers as an aftertaste, giving a feeling of discomfort.
(3)水溶液を酸性側にすると、沈澱を生じたり、ゲル
化したりして、低pH食品に使用しにくく、調味料とし
て用途が制限されている。(3) If the aqueous solution is made acidic, it may precipitate or gel, making it difficult to use in low-pH foods and limiting its use as a seasoning.
(4)グリチルリチン水溶液は、撹拌、濃縮、煮詰めな
どにより発泡しやす(、必要に応じて消泡剤を使用する
などその取扱いに苦心している。(4) Glycyrrhizin aqueous solutions tend to foam when stirred, concentrated, boiled down, etc. (However, it is difficult to handle them, such as using antifoaming agents as necessary.
グリチルリチンのこれら欠点を改良するために、例えば
特公昭49−7227号公報では、クエン酸ナトリウム
をグリチルリチンの30%乃至500%添加して混合使
用することによりグリチルリチンの呈味を改善すること
を提案し、また、特公昭43−17721号公報では、
甘草の水油出物にアルカリ金属塩および澱粉分解物を加
えて加熱することにより、酸性下での沈澱やゲル形成を
防止することを提案し、更に、特開昭50−29777
号公報では、酸性下でのグリチルリチンの使用に際し、
グルコノデルタラクトンとアルカリ金属塩類とを併用す
ることによりグリチルリチンの沈澱やゲル形成を防止す
ることを提案している。しかしながら、これら提案にお
いてもその改良はなお不十分であることが判明した。In order to improve these drawbacks of glycyrrhizin, for example, Japanese Patent Publication No. 49-7227 proposes to improve the taste of glycyrrhizin by adding sodium citrate in an amount of 30% to 500% of glycyrrhizin. , and in Japanese Patent Publication No. 43-17721,
He proposed that precipitation and gel formation under acidic conditions could be prevented by adding alkali metal salts and starch decomposition products to the water-oil extract of licorice and heating the mixture.
In the publication, when using glycyrrhizin under acidic conditions,
It is proposed that the precipitation and gel formation of glycyrrhizin can be prevented by using glucono delta-lactone and an alkali metal salt in combination. However, even with these proposals, it has been found that the improvements are still insufficient.
本発明者等は、グリチルリチンの前記欠点を解消するこ
とを目的に鋭意研究した。The present inventors conducted extensive research with the aim of eliminating the above-mentioned drawbacks of glycyrrhizin.
その結果、澱粉質とともにグリチルリチンを含有する水
iWWにシクロデキストリン・グルカノトランスフェラ
ーゼを作用きせることにより、澱粉部分分解物とともに
グリチルリチン分子にα−グルコシル残基が等モル以上
結合したα−グリコシルグリチルリチンが生成されるこ
とを見出し、更に、この反応で生成きれる澱粉部分分解
物およびα−グリコシルグリチルリチン含有製品は、従
来のグリチルリチン製品とは全く違って、(1)嫌味、
薬品臭がなく、まろやかな甘味を呈する。As a result, by applying cyclodextrin glucanotransferase to water iWW containing glycyrrhizin as well as starch, α-glycosylglycyrrhizin, in which more than the same mole of α-glucosyl residues are bound to glycyrrhizin molecules, is produced together with starch partial decomposition products. Furthermore, the starch partial decomposition products and α-glycosylglycyrrhizin-containing products produced by this reaction are completely different from conventional glycyrrhizin products in that they have: (1) unpleasant taste;
It has no chemical odor and has a mild sweet taste.
(2)甘味が早く現れ、後味として長く尾を引かない。(2) Sweetness appears quickly and does not linger as an aftertaste.
(3)酸性下においても沈澱形成、ゲル形成が極度に抑
えられる。(3) Precipitate formation and gel formation are extremely suppressed even under acidic conditions.
(4)泡立ちが抑制され、取扱いが容易となる。(4) Foaming is suppressed and handling becomes easy.
などの極めて優れた性質を有していること、とりわけ、
α−グリコシルグリチルリチン含有製品に澱粉部分分解
物の共存は、特に泡立ての抑制、呈味改良に大きく寄与
していることを見出し、これが飲食物などの甘味付け、
呈味改良に好適であることを確認して、本発明を完成し
た。In particular, it has extremely excellent properties such as,
We found that the coexistence of starch partial decomposition products in α-glycosylglycyrrhizin-containing products greatly contributes to suppressing foaming and improving taste, and this contributes greatly to the sweetening of foods and drinks, etc.
The present invention was completed after confirming that it is suitable for improving taste.
本発明でいう飲食物などとは単に飲料および食品だけで
なく、味覚刺激を味わうことので参る物品全般を意味し
、例えば酒類、清涼飲料などの飲料類、甘味料などの調
味料、菓子、漬物などの食品類、飼料、餌料類、リップ
クリーム、#!I磨などの化粧品類、うがい薬、内服薬
などの医薬品類などを意味する。Foods and drinks as used in the present invention refer not only to beverages and foods, but also to general goods that provide taste stimulation, such as alcoholic beverages, beverages such as soft drinks, seasonings such as sweeteners, sweets, and pickles. Foods, feed, feedstuffs, lip balm, #! It refers to cosmetics such as I-washing products, and pharmaceutical products such as mouthwashes and oral medicines.
本発明でいうα−グリコシルグリチルリチンは、グリチ
ルリチン分子にα−グルコシル残基が等モル以上結合し
たα−グリコシルグリチルリチンを含有しておればよい
。The α-glycosylglycyrrhizin referred to in the present invention may contain α-glycosylglycyrrhizin in which equal moles or more of α-glucosyl residues are bound to a glycyrrhizin molecule.
本発明の反応方法としては、澱粉質とともにグリチルリ
チンを含有する水溶液にシクロデキストリン・グルカノ
トランスフェラーゼ(E C2,4,1゜19)を作用
させる方法を採用すればよい。As a reaction method of the present invention, a method may be employed in which cyclodextrin glucanotransferase (EC2,4,1°19) is allowed to act on an aqueous solution containing glycyrrhizin as well as starch.
以下、この反応方法をより詳細に説明する。This reaction method will be explained in more detail below.
本発明に用いる澱粉質としては、シクロデキストリン・
グルカノトランスフェラーゼの基質となり、そのα−グ
ルコシル残基の1又は2分子以上がグリチルリチン分子
に転移されα−グリコシルグリチルリチンを生成しうる
ものであればよく、通常、アミロース、アミロペクチン
、澱粉tこけでな(、例えばシクロデキストリン、DE
l乃至50程度の澱粉液化、物、澱粉糖化物などの澱粉
部分分解物も好んで用いられる。また、原料の澱粉は、
甘藷、馬鈴薯などの地下系澱粉であワても、米、小麦、
コーンなどの地上系澱粉であ)てもよ(、更に粗グリチ
ルリチンなどに共存している甘草由来の澱粉であっても
よい。The starch used in the present invention includes cyclodextrin,
Any substance that can serve as a substrate for glucanotransferase and generate α-glycosylglycyrrhizin by transferring one or more molecules of its α-glucosyl residue to a glycyrrhizin molecule is sufficient, usually amylose, amylopectin, starch and moss. (e.g. cyclodextrin, DE
Partially decomposed starch products such as starch liquefaction products, starch saccharified products, and the like having a concentration of about 1 to 50% are also preferably used. In addition, the raw material starch is
Even if the underground starch such as sweet potato and potato is used, rice, wheat,
It may be ground-based starch such as corn (or starch derived from licorice, which coexists with crude glycyrrhizin etc.).
また、本発明に用いるグリチルリチンは、グリチルリチ
ン酸又はその塩を含有し、α−グリコシルグリチルリチ
ンを生成するものであればよい。Further, the glycyrrhizin used in the present invention may be any glycyrrhizin containing glycyrrhizic acid or a salt thereof and producing α-glycosylglycyrrhizin.
従って、高度に精Ii!すれたグリチルリチン製品だけ
でなく、甘草からのグリチルリチンを含有する粗抽出物
であってもよい。Therefore, highly refined Ii! It can be a crude glycyrrhizin product as well as a crude extract containing glycyrrhizin from licorice.
シクロデキストリン会グルカノトランスフェラーゼは、
例えば、特開昭47−20373号公報、特開昭50−
63189号公報、特開昭50−88:190号公報、
ハンス・ベンダー(Hans Bender) 、アー
カイブスーオブ・マイクロバイオロジー(Archiv
es of旧crobiology)、第111巻、第
271乃至282頁(1977年)などに示されている
ように、バチルス・マセランス(Bacillusma
cerans) 、バチルス・メガテリウム(Baci
llusmegat、erium) 、バチルス・サー
キュランス(Baa目lus cjrculans)
、バチルス中ポリミキサ(Bacillus poly
myxa) 、バチルス・ステアロサーモフィラス(B
acillus stearothermophilu
s)などのバチルス属、クレブシーラ・ニューモニアエ
(に1ebsiella pneumonias)など
のクレブシーラ属などの細菌によって生産されることが
知られており、何れも本発明に自由に用いることができ
る。また、シクロデキストリン会グルカノトランスフェ
ラーゼは、必ずしも精製して使用する必要はなく、通常
は粗酵素で目的を達成することができる。Cyclodextrin-associated glucanotransferase is
For example, JP-A-47-20373, JP-A-50-
No. 63189, Japanese Patent Application Laid-open No. 1988-190,
Hans Bender, Archives of Microbiology
es of crobiology, Vol. 111, pp. 271-282 (1977), Bacillus macerans
cerans), Bacillus megaterium (Bacillus
llusmegat, erium), Bacillus circulans (Baaales lus cjrculans)
, Bacillus polymixer
myxa), Bacillus stearothermophilus (B
acillus stearothermophilu
It is known to be produced by bacteria of the genus Bacillus, such as S. s), and of the genus Klebsiella, such as Klebsiella pneumoniae, and any of them can be freely used in the present invention. Furthermore, cyclodextrin-associated glucanotransferase does not necessarily need to be purified before use, and the purpose can usually be achieved with crude enzyme.
また、必要ならば、シクロデキストリン・グルカノトラ
ンスフェラーゼを固定化してバッチ式で反応に繰返し利
用することも、連続式で利用することも随意である。Furthermore, if necessary, it is optional to immobilize cyclodextrin glucanotransferase and use it repeatedly in batchwise reactions or continuously.
シクロデキストリン・グルカノトランスフェラーゼの反
応条件は、澱粉質とグリチルリチンとを含有する水溶液
にシクロデキストリン・グルカノトランスフェラーゼを
反応きせることができればよい。The reaction conditions for cyclodextrin glucanotransferase may be as long as they allow cyclodextrin glucanotransferase to react with an aqueous solution containing starch and glycyrrhizin.
通常、澱粉質を溶解して反応液中の濃度を約1乃至50
W/v%とし、グリチルリチンの濃度を約0.1乃至2
5v/W%とすればよく、また、澱粉質とグリチルリチ
ンとの比率は、澱粉質をグリチルリチンに対して固形物
当り約0.5乃至500倍の範囲にするのが好ましい。Usually, by dissolving starch, the concentration in the reaction solution is about 1 to 50.
W/v%, and the concentration of glycyrrhizin is approximately 0.1 to 2.
The ratio of starch to glycyrrhizin is preferably about 0.5 to 500 times that of glycyrrhizin on a solid basis.
反応液のPHと温度はシクロデキストリン・グルカノト
ランスフェラーゼが作用できればよく、通常pH3乃至
101温度20乃至80℃の範囲から選ばれる。The pH and temperature of the reaction solution may be selected as long as the cyclodextrin glucanotransferase can act, and are usually selected from the range of pH 3 to 101 and temperature 20 to 80°C.
また、シクロデキストリン・グルカノトランスフェラー
ゼの作用によって、澱粉部分分解物とともにα−グリコ
シルグリチルリチンを生成させ、更に必要ならば、α−
アミラーゼ、β−アミラーゼなどを作用させ、その粘度
、呈味などが改善きれた澱粉部分分解物およびα−グリ
コシルグリチルリチン含有製品にすることも随意である
。In addition, by the action of cyclodextrin glucanotransferase, α-glycosylglycyrrhizin is produced together with starch partial decomposition products, and if necessary, α-
It is also optional to use amylase, β-amylase, etc. to act on the product to produce starch partial decomposition products and α-glycosylglycyrrhizin-containing products with improved viscosity, taste, etc.
本発明では、目的によっては、反応液そのままでも澱粉
部分分解物およびα−グリコシルグリチルリチン含有製
品として使用できるが、必要に応じて反応後に酵素を加
熱失活させた後、ケイ酸アルミン酸マグネシウム(例え
ば、富士化学工業株式会社製造、商品名ノイシリン)、
マグネシア系吸着剤(例えば、北海道曹達株式会社製造
、商品名M−511)など1有色夾雑物を吸着除去し、
その非吸着部分を採取してV粉部分分解物およびα−グ
リコシルグリチルリチン含有製品とするが、更に、これ
を濃縮してシラツブ状の澱粉部分分解物およびα−グリ
コシルグリチルリチン含有製品、或いは、更に、乾燥し
て粉末状の澱粉部分分解物およびα−グリコシルグリチ
ルリチン含有製品とすることもできる。In the present invention, depending on the purpose, the reaction solution can be used as it is as a starch partial decomposition product and α-glycosylglycyrrhizin-containing product. , manufactured by Fuji Chemical Industry Co., Ltd. (trade name: Neusilin),
A magnesia-based adsorbent (for example, manufactured by Hokkaido Soda Co., Ltd., trade name M-511) adsorbs and removes colored impurities,
The non-adsorbed portion is collected to produce a V powder partial decomposition product and an α-glycosylglycyrrhizin-containing product, which is then concentrated to produce a slag-like starch partial decomposition product and an α-glycosylglycyrrhizin-containing product, or further, It can also be dried into powdered starch partial decomposition products and α-glycosylglycyrrhizin-containing products.
必要ならば、H型イオン交換樹脂を用いて脱塩精製した
澱粉部分分解物およびα−グリコシルグリチルリチン含
有製品にすることもできる。If necessary, starch partial decomposition products and α-glycosylglycyrrhizin-containing products that have been desalted and purified using an H-type ion exchange resin can also be produced.
これらの澱粉部分分解物およびα−グリコシルグリチル
リチン含有製品に含まれるα−グリコシルグリチルリチ
ンなどのグリチルリチン化合物と遊離の澱粉部分分解物
とを分離する必要がある場合には、合成吸着剤(例えば
、三菱化成工業株式会社製造、商品名HP−10、HP
−20、又は、ローム社製−フ社製造、商品名アンバー
ライトXAD−2、アンバーライトX A D−7など
)を充填したカラムに通液すれば、α−グリコシルグリ
チルリチン、未反応のグリチルリチンなどのグリチルリ
チン化合物は吸着され、多量に共存する水溶性澱粉部分
分解物は吸着されることなくそのまま流出する。この流
出液から、シクロデキストリンなどの澱粉部分分解物を
採取することも随意である。更に、この多孔性合成吸着
剤を希アルカリ水、水などで洗浄した後、比較的少量の
有機溶媒または有機溶媒と水との混合液、例えばメタノ
ール水、エタノール水などを通液すれば、まず遊離の澱
粉部分分解物を含まないα−グリコシルグリチルリチン
が溶出され、次いで、通液量を増すか有機溶媒濃度を高
めるかすれば、未反応のグリチルリチンが1容出してく
る。このα−グリコシルグリチルリチン高含有溶出液を
照温して、まず有機溶媒を除去し、これを適当な濃度ま
で濃縮してシラツブ状高純度α−グリコシルグリチルリ
チン含有製品とするか、更には乾燥粉末化して粉末状高
純度α−グリコシルグリチルリチン含有製品とすること
ができる。If it is necessary to separate free starch partial decomposition products from glycyrrhizin compounds such as α-glycosylglycyrrhizin contained in products containing these starch partial decomposition products and α-glycosylglycyrrhizin, synthetic adsorbents (for example, Mitsubishi Chemical Manufactured by Kogyo Co., Ltd., product name HP-10, HP
If the liquid is passed through a column filled with Amberlite XAD-2, Amberlite XAD-2, Amberlite The glycyrrhizin compound is adsorbed, and the water-soluble starch partial decomposition products that coexist in large quantities flow out without being adsorbed. It is also optional to collect starch partial decomposition products such as cyclodextrin from this effluent. Furthermore, after washing this porous synthetic adsorbent with dilute alkaline water, water, etc., if a relatively small amount of an organic solvent or a mixture of an organic solvent and water, such as methanol water or ethanol water, is passed through it, α-glycosylglycyrrhizin that does not contain free starch partial decomposition products is eluted, and then, by increasing the flow rate or increasing the organic solvent concentration, one volume of unreacted glycyrrhizin comes out. This α-glycosylglycyrrhizin-rich eluate is heated to remove the organic solvent, and it is concentrated to an appropriate concentration to produce a sill-like high-purity α-glycosylglycyrrhizin-containing product, or it can be further converted into a dry powder. A product containing powdered high-purity α-glycosylglycyrrhizin can be obtained.
このようにして得られる各種α−グリコシルグリチルリ
チン含有製品は、従来極めて遅かった甘味の発現が著し
く早まるため甘味度の比較は困難であるが、最大発現時
で比較すれば、使用したグリチルリチン固形物重量に見
合う甘味度とばば同程度乃至やや弱い程度である。また
、その甘味の質は、粉末状のものをそのまま口に含んで
も苦味、渋味、えぐ昧などの嫌味をほとんど呈すること
なく、まろやかな甘味を呈し、残り味の切れもよい。It is difficult to compare the sweetness of various α-glycosylglycyrrhizin-containing products obtained in this way because the onset of sweetness, which was conventionally extremely slow, is significantly accelerated. The sweetness level is about the same as that of Baba, or slightly weaker. In addition, the quality of the sweetness is such that even when the powdered product is taken directly into the mouth, it exhibits almost no unpleasant tastes such as bitterness, astringency, or astringency, and exhibits a mellow sweetness with a good lingering taste.
また、α−グリコシルグリチルリチンを含有するシラツ
ブ状製品は、酸性下においても沈澱形成、ゲル形成が極
度に抑えられ、低pH飲料、低pH食品の甘味付け、調
味などに自由に利用できることが判明した。In addition, it was found that the slag-like product containing α-glycosylglycyrrhizin has extremely low precipitation and gel formation even under acidic conditions, and can be freely used for sweetening and seasoning of low-pH beverages and low-pH foods. .
また、α−グリコシルグリチルリチンを含有するシラツ
ブ状製品、とりわけ、澱粉部分分解物およびα−グリコ
シルグリチルリチン含有製品は、グリチルリチンの場合
と比較して泡立ちが極めて少な(、その取り扱いの容易
であること、更に、呈味改良効果の高いことが判明した
。In addition, slag-like products containing α-glycosylglycyrrhizin, especially starch partial decomposition products and α-glycosylglycyrrhizin-containing products, have extremely low foaming (, ease of handling, and , was found to be highly effective in improving taste.
また、α−グリコシルグリチルリチンを含有する粉末状
製品は、それに含まれる各α−グリコジル化合物が互い
に溶は合ったいわゆる固溶体の粉末である。従って、こ
の粉末の水に対する溶解速度は、瞬時に溶解できる程大
きく、しかもその溶解度には際限がないので、シラツブ
状からベースト状になる程の高濃度にも自由に溶解する
ことができる。Further, the powdered product containing α-glycosylglycyrrhizin is a so-called solid solution powder in which the various α-glycodyl compounds contained therein are dissolved in each other. Therefore, the dissolution rate of this powder in water is so high that it can be dissolved instantaneously, and there is no limit to its solubility, so that it can be freely dissolved at such high concentrations that it changes from a slag-like shape to a base-like state.
また、α−グリコシルグリチルリチン含有製品は、その
ママで甘味付け、呈味改良などのために調味料として使
用できる。必要ならば、例えば水飴、グルコース、マル
トース、異性化糖、カップリングシュガー(林原株式会
社の登録商I!!A)、砂糖、蜂蜜、メーブルシュガー
、ソルビット、マルチトール、ラクチトール、ジヒドロ
カルコン、L−アスパラチルフェニルアラニンメチルエ
ステル、サッカリン、グリシン、アラニン、グリチルリ
チン、ステビオシト、α−グリコシルステビオシド、レ
バウディオシドAなどのような他の甘味料と、またクエ
ン酸、リンゴ酸などの有機酸又はその塩、グルタミン酸
、アスパラギン酸などのアミノ酸又はその塩、またデキ
ストリン、澱粉、乳糖などのような増量剤、更には着香
料、着色料などと混合して使用することも随意である。Furthermore, α-glycosylglycyrrhizin-containing products can be used as seasonings for sweetening, improving taste, etc. If necessary, for example, starch syrup, glucose, maltose, isomerized sugar, coupling sugar (registered trademark I!!A of Hayashibara Co., Ltd.), sugar, honey, maable sugar, sorbitol, maltitol, lactitol, dihydrochalcone, L- With other sweeteners such as asparatyl phenylalanine methyl ester, saccharin, glycine, alanine, glycyrrhizin, steviocyto, alpha-glycosyl stevioside, rebaudioside A etc., and also with organic acids or their salts such as citric acid, malic acid, glutamic acid, asparagine. It is also optional to use it in combination with amino acids such as acids or salts thereof, fillers such as dextrin, starch, lactose, etc., as well as flavoring agents, coloring agents, and the like.
また、α−グリコシルグリチルリチン含有製品の粉末品
は、そのまま又は必要に応じて増量剤、賦型剤と混合し
て顆粒状、球状、タブレット状などに成型して使用する
こともでき、液状品は使用上便利なように、その濃度を
調節することもできる。Powdered products containing α-glycosylglycyrrhizin can be used as they are or mixed with fillers and excipients as needed to form granules, spheres, tablets, etc., and liquid products can be used as is. The concentration can also be adjusted for convenience in use.
α−グリコシルグリチルリチン含有製品の甘味度は、前
記したように反応に用いた固形物重量に見合う甘味度と
ほぼ同程度乃至やや弱い程度であることから、反応に用
いる澱粉質とグリチルリチンとの固形物重量当りの比率
によって変わってくる。As mentioned above, the sweetness of α-glycosylglycyrrhizin-containing products is approximately the same or slightly weaker than the sweetness commensurate with the weight of the solid material used in the reaction. It varies depending on the weight ratio.
砂糖の甘味度より高い甘味度のα−グリコシルグリチル
リチン含有製品で甘味付けする場合には、必要甘味に対
する製品の使用量が砂糖よりも大幅に低下することから
、甘味付けされた飲食物、嗜好物などのカロリーを低下
させることができる。When sweetening with α-glycosylglycyrrhizin-containing products with a sweetness level higher than that of sugar, the amount of the product used for the required sweetness is significantly lower than that of sugar. can reduce calories.
換言すれば、α−グリコシルグリチルリチン含有製品は
、糖尿病者、肥満者などのカロリーを制限している人な
どのための低カロリー製品として、また低カロリー飲食
物、低カロリー嗜好物など、いわゆる美容食、健康食、
ダイエツト食への甘味付けに利用できるのである。In other words, α-glycosylglycyrrhizin-containing products can be used as low-calorie products for people who are restricting their calories, such as diabetics and obese people, as well as for so-called beauty foods such as low-calorie drinks and low-calorie luxury foods. , healthy food,
It can be used to sweeten diet foods.
また、α−グリコシルグリチルリチン含有製品は、虫歯
原因菌などによって発酵きれにくいことなどより、虫歯
を起こしにくい甘味料としても利用できる。例えば、チ
ューインガム、チョコレート、ビスケット、クツキー、
キャラメル、キャンデーなどの菓子類、コーラ、サイダ
ー、ジュース、コーヒー、乳酸飲料などの飲料水類など
における虫歯を起こしにくい飲食物、嗜好物などへの甘
味付けに好適である。また、うがい水や諌歯耶なと、化
粧品、医薬品などへも虫歯を懸念することなく甘味付け
できるので好都合である。Products containing α-glycosylglycyrrhizin can also be used as sweeteners that are less likely to cause dental caries, as they are less likely to be fermented by caries-causing bacteria. For example, chewing gum, chocolate, biscuits, kutsky,
It is suitable for sweetening foods and beverages that are less likely to cause dental caries, such as confectionery such as caramel and candy, drinking water such as cola, cider, juice, coffee, and lactic acid drinks, and favorite foods. It is also advantageous because it can be used to sweeten gargle water, cosmetics, medicines, etc. without worrying about cavities.
更に、α−グリコシルグリチルリチン含有製品は、酸味
、塩から味、渋味、旨味、苦味などの他の呈味を有する
各種物質ともよく調和し、耐酸性、耐熱性も大きいので
、今まで述べたような特殊な場合だけでなく、普通一般
の飲食物、嗜好物などへの甘味付けに、また呈味改良な
どの目的で利用することも随意である。例えば、醤油、
粉末醤油、味噌、粉末味噌、もろみ、ひしお、マヨネー
ズ、ドレッシング、食酢、三杯酢、粉末すし酢、中華の
素、天つゆ、麺つゆ、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、
複合調味料、みりん、新みりん、テーブルシラツブなど
の各種調味料、せんべい、あられ、おこし、餅類、まん
じゅう、ういろう、あん類、羊焚、水羊舜、錦玉、ゼリ
ー、カステラ、th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、シューク
リーム、ワツフル、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、キャンデーなど
の各種洋菓子、アイスクリーム、シャーベットなどの氷
菓、果実のシロップ漬、水蜜などのシロップ類、バター
クリーム、カスタードクリーム、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スプレッド、
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、野菜の加工食品類、福神漬、べったら漬、
午枚漬、らっきょう潰などの漬物類、ハム、ソーセージ
などの畜肉製品類、魚肉ハム、魚肉ソーセージ、カマボ
コ、チクワ、天ぷらなどの魚肉製品、ウニ、イカの塩辛
、ききするめ、ふぐのみりん干しなどの各種珍味類、の
り、山菜、するめ、小魚、貝などで製造されるつくだ魚
類、煮豆、ポテトサラダ、コンブ巻などのそう菜食品、
魚肉、畜肉、果実、野菜などのビン詰、缶詰類、合成酒
、果実酒、洋酒などの酒類、コーヒー、ココア、ジュー
ス、炭酸飲料、乳酸飲料、乳酸菌飲料などの清涼飲料水
、プリンミックス、ホットケーキミックス、即席ジュー
ス、即席コーヒー、即席しるこなど即席飲食品などの各
種飲食物、嗜好物の甘味付け、呈味改良などに使用する
ことも随意である。Furthermore, α-glycosylglycyrrhizin-containing products blend well with various substances having other tastes such as sour, salty, astringent, umami, and bitter, and have high acid resistance and heat resistance, so they are highly resistant to acids and heat. It can be used not only in such special cases, but also for the purpose of sweetening ordinary foods, drinks, favorite foods, etc., and for improving taste. For example, soy sauce,
Powdered soy sauce, miso, powdered miso, moromi, hishio, mayonnaise, dressing, vinegar, sambai vinegar, powdered sushi vinegar, Chinese base, tempura soup, mentsuyu, sauce, ketchup, yakiniku sauce, curry roux, stew base, soup base , dashi stock,
Compound seasonings, various seasonings such as mirin, new mirin, and table sardines, rice crackers, arare, okoshi, rice cakes, manju, sweet bean paste, red bean paste, sheep-roasted, water yolk shun, nishikidama, jelly, castella, and th-dama. Various Japanese sweets such as bread, biscuits, crackers, cutlets, pies, puddings, cream puffs, Watsufules, sponge cakes, donuts, chocolates, chewing gum, caramels, various Western sweets such as candies, frozen confections such as ice cream and sorbet, fruits pickled in syrup , syrups such as honey, spreads such as butter cream, custard cream, flower paste, peanut paste, fuller paste,
Processed fruits and vegetables such as pastes, jams, marmalade, syrup pickles, sugar fruits, Fukujinzuke, Bettarazuke,
Pickles such as pickles and crushed rakkyo, meat products such as ham and sausages, fish products such as fish ham, fish sausage, kamaboko, chikuwa, and tempura, salted sea urchin and squid, kikisurume, mirin-dried blowfish, etc. Various kinds of delicacies, seaweed, wild vegetables, dried dried dried dried dried dried dried fish, small fish, shellfish, etc., vegetable foods such as boiled beans, potato salad, kelp rolls, etc.
Bottled and canned foods such as fish, meat, fruits, and vegetables, alcoholic beverages such as synthetic liquor, fruit liquor, and Western liquor, soft drinks such as coffee, cocoa, juice, carbonated drinks, lactic acid drinks, and lactic acid bacteria drinks, pudding mixes, and hot drinks. It can also be optionally used to sweeten and improve the taste of various foods and beverages such as cake mixes, instant juices, instant coffee, instant shiruko, and other instant foods and beverages, as well as favorite foods.
また、家畜、家禽、その他蜜蜂、蚕、魚などの飼育動物
のための飼料、飼料、ベットフードなどの嗜好性を向上
させる目的で使用することもできる。Moreover, it can also be used for the purpose of improving the palatability of livestock, poultry, and other domesticated animals such as bees, silkworms, and fish, fodder, and bed food.
その他、タバコ、線側り口紅、リップクリーム、内服薬
、トローチ、肝油ドロップ、口中清涼剤、口中香錠、う
がい薬など各種固型状、ペースト状、液状の嗜好物、化
粧品、医薬品などへの甘味剤として、又は呈味改良剤、
矯味剤などとして利用することも有利に実施できる。Other sweeteners include cigarettes, lipstick, lip balm, oral medications, pastilles, cod liver oil drops, mouth fresheners, pastilles, gargles, and other solid, paste, and liquid favorites, cosmetics, and pharmaceuticals. as a taste improver,
It can also be advantageously used as a flavoring agent.
更に、α−グリコシルグリチルリチン含有製品を生薬甘
草と同じ薬効用途、すなわち消炎、ioi。Furthermore, α-glycosylglycyrrhizin-containing products can be used for the same medicinal purposes as the herbal medicine licorice, namely anti-inflammatory, Ioi.
営よ痰、咳止め、抗ウィルス剤、抗アレルギー剤などの
用途にも使用することができ、例えば咳止めシロップ、
ぜんそくの発作を抑える錠剤などとして使用で沙る。It can also be used as a cough suppressant, antiviral agent, antiallergic agent, etc. For example, cough syrup,
It is used as a tablet to suppress asthma attacks.
特に、澱粉部分分解物およびα−グリコシルグリチルリ
チン含有製品の場合には、泡立ちが極度に抑制され、呈
味改良効果も高いので、例えば、醤油、麺つゆ、飲料な
どの液状飲食物、ハードキャンデー、佃煮などの煮詰工
程を必要とする飲食物、ドリンク剤、シロップなどの液
状医薬品などへの用途に有利に利用できる。In particular, in the case of products containing starch partial decomposition products and α-glycosylglycyrrhizin, foaming is extremely suppressed and the taste improvement effect is high. It can be advantageously used in foods and beverages that require a boiling process such as tsukudani, drinks, and liquid pharmaceuticals such as syrup.
以上述べたような飲食物、嗜好物、飼料、餌料、化粧品
、医薬品などにα−グリコシルグリチルリチン含有製品
を使用するには、その最終製品が完成するまでの工程に
、例えば、混和、混捏、溶解、浸漬、滲透、散布、塗布
、噴霧、注入など公知の方法で適宜含有せしめることに
より行なわれる。In order to use α-glycosylglycyrrhizin-containing products for foods and beverages, luxury foods, feeds, feedstuffs, cosmetics, pharmaceuticals, etc., there are many steps required to complete the final product, such as mixing, kneading, and dissolving. This can be carried out by appropriately incorporating them by known methods such as dipping, percolation, scattering, coating, spraying, and injection.
以下、α−グリコシルグリチルリチン含有製品を実験に
基づいて説明する。Hereinafter, α-glycosylglycyrrhizin-containing products will be explained based on experiments.
実 !91 α−グリコシルグリチルリチン含有製品の
調製
1−1 グルコシル転移酵素の調製
バチルス・ステアロサーモフィラス(Bacillus
stearothermophilus) FERN−
P No、2222をソリュブルスターチ2W/V%、
硝酸アンモニウムIW/V%、リン酸2カリウム0.I
W/V%、硫酸マグネシウム・7水塩0.05W/V%
、:1−ンスfイーフIJカー0.5V/V%、炭酸カ
ルシウムIW/V%および水からなる殺菌した液体培地
!OLに植菌し、50℃で3日間通気撹拌培養した。得
られた培養液を遠心分離して、その上清を硫安0.7飽
和で塩析し、シクロデキストリン・グルカノトランスフ
ェラーゼ(EC2,4,1,19)の活性約go、oo
o単位を有する粗酵素標品を得た。ここでいう活性1単
位とは、pH5,5,0,02Mの酢酸緩衝液および2
X10−3Mの塩化カルシウムを含む0.3W/V%の
ソリュブルスターチ溶液5■Lに、適当に希釈した酵素
液0.2糺を加え、40℃で10分間反応させた後、そ
の反応液0.5糺をとり、0.02N−硫酸水溶液15
mLに混合して反応を停止させ、ざらにこの反応停止液
に0.INヨウ素ヨウ化カリウム溶液0.2■Lを加え
て発色させ、次いで660n−における吸光度を測定し
て、40℃で10分間反応きせることによりソリュブル
スターチ15mgのヨウ素の呈色を完全に消失きせる酵
素量をいう。fruit ! 91 Preparation of α-glycosylglycyrrhizin-containing products 1-1 Preparation of glucosyltransferase Bacillus stearothermophilus
stearothermophilus) FERN-
P No. 2222 with soluble starch 2W/V%,
Ammonium nitrate IW/V%, dipotassium phosphate 0. I
W/V%, magnesium sulfate heptahydrate 0.05W/V%
A sterile liquid medium consisting of: 1-nsf IJ car 0.5 V/V%, calcium carbonate IW/V% and water! The cells were inoculated into OL and cultured with aeration at 50°C for 3 days. The obtained culture solution was centrifuged, and the supernatant was salted out with 0.7 saturated ammonium sulfate to determine the activity of cyclodextrin glucanotransferase (EC2, 4, 1, 19), approximately go, oo.
A crude enzyme preparation having o units was obtained. 1 unit of activity here means acetate buffer with pH 5, 5, 0, 2M and 2
Add 0.2 liters of an appropriately diluted enzyme solution to 5 L of a 0.3 W/V% soluble starch solution containing X10-3M calcium chloride, react at 40°C for 10 minutes, and then .5 Remove the glue and add 0.02N sulfuric acid aqueous solution 15
mL to stop the reaction, add roughly 0.0 ml to this reaction stop solution. An enzyme that completely eliminates the coloration of iodine in 15 mg of soluble starch by adding 0.2 L of IN iodine potassium iodide solution to develop color, then measuring the absorbance at 660 n-, and reacting at 40°C for 10 minutes. Refers to quantity.
1−2 酵素反応
精製グリチルリチン(丸善化成株式会社製造、商品名純
グリチミン) 100gと、澱粉質としてマルトデキス
トリン(D E30) 500gとを水5Lに加熱溶解
した後、60℃に冷却すると共に、pHa、。1-2 After heating and dissolving 100 g of enzyme reaction purified glycyrrhizin (manufactured by Maruzen Kasei Co., Ltd., trade name: pure glycymin) and 500 g of maltodextrin (D E30) as a starch substance in 5 L of water, the solution was cooled to 60°C and the pH ,.
に調整し、これに前述の粗シクロデキストリン・グルカ
ノトランスフェラーゼ標品のs 、 ooo単位を加え
、pH6,0,60℃に維持しつつ24時間反応させた
。この反応液を95℃に10分間保って酵素を加熱失活
させた(この標品は第1表の試料No、3に相当する。The s and ooo units of the crude cyclodextrin glucanotransferase preparation described above were added to this, and the mixture was reacted for 24 hours while maintaining the pH at 6.0 and 60°C. This reaction solution was kept at 95° C. for 10 minutes to inactivate the enzyme by heating (this sample corresponds to sample No. 3 in Table 1).
)後、濾過して得た濾液を70℃以下で減圧濃縮すると
ともに、乾燥して粉末品(この標品は第1表の試料No
、4に相当する。)を得た。), the filtrate obtained by filtration was concentrated under reduced pressure at 70°C or lower, and dried to form a powder (this specimen is sample No. 1 in Table 1).
, corresponds to 4. ) was obtained.
対照品は同様に加熱溶解後、反応工程、加熱失活工程ま
でを経たもので、その配合組成は第1表に示す。The control product was similarly subjected to heat dissolution, reaction step, and heat deactivation step, and its composition is shown in Table 1.
第1表
実 験2 甘味の質の比較テスト
予備テストから求めた甘味度から算出して、各試料を1
0%砂糖水溶液に相当する甘味度の水溶液に調製した。Table 1 Experiment 2 Sweet taste quality comparison test Calculated from the sweetness level obtained from the preliminary test, each sample was
An aqueous solution having a sweetness level equivalent to a 0% aqueous sugar solution was prepared.
そして、最も劣っているものと、最も優れているものを
各1つずつ選出させ、かつ味質について意見を求めた。They were then asked to select one item as the worst and one as the best, and asked for their opinions on the taste quality.
20名のパネル員で25℃の室温で行った。その結果は
、第2表に示す通りであった。The test was conducted at room temperature of 25°C with 20 panel members. The results were as shown in Table 2.
第2表
第2表の結果から、試料No、1、No、2の対照品は
、甘味の質が劣っており、これに対し、澱粉部分分解物
とグリチルリチンとを含有する水溶液にシクロデキスト
リン・グルカノトランスフェラーゼを作用させて得られ
た試料No、3、No、4の本発明品は、甘味の質が砂
糖のそれに近く優れている。Table 2 From the results shown in Table 2, the control products of Samples No. 1, No. 2, and No. 2 had poor quality of sweetness. The products of the present invention, samples No. 3, No. 4, obtained by the action of glucanotransferase, have excellent sweetness quality that is close to that of sugar.
従って、澱粉部分分解物およびα−グリコシルグリチル
リチン含有製品は、従来のグリチルリチン、またはグリ
チルリチンと澱粉部分分解物との単なる混合物などとは
違って、嫌味がなく、まろやかな砂糖に近い甘味を有し
ており、しかも残り味の切れもよいことから、そのまま
口に含んで甘味を味わうことのできる極めて優れた甘味
料である。Therefore, products containing starch partial decomposition products and α-glycosylglycyrrhizin, unlike conventional glycyrrhizin or a simple mixture of glycyrrhizin and starch partial decomposition products, have no unpleasant taste and have a mellow sweetness similar to sugar. It is an extremely excellent sweetener that can be put in the mouth and enjoy the sweetness as it has a good flavor and leaves no residual flavor.
実 験3 α−グリコシルグリチルリチンの確認実験1
−2で調製した試料No、4の15gを水100mLに
溶解して得られる溶液を、合成吸着剤(三菱化成工業株
式会社製造、商品名HP −20) 100■Lのカラ
ムに通液した後、充分水洗して遊離の澱粉部分分解物を
除去した。次いで、このカラムに50V/V%メタノー
ル300aLを通してα−グリコシルグリチルリチンな
どのグリチルリチン化合物を溶出し、濃縮、乾燥、粉砕
して約2.5gの粉末(試料No、5)を得た。Experiment 3 Confirmation experiment 1 of α-glycosylglycyrrhizin
A solution obtained by dissolving 15 g of sample No. 4 prepared in -2 in 100 mL of water was passed through a 100 μL column of synthetic adsorbent (manufactured by Mitsubishi Chemical Corporation, trade name HP-20). The free starch partial decomposition products were removed by thorough washing with water. Next, 300 aL of 50V/V% methanol was passed through this column to elute glycyrrhizin compounds such as α-glycosylglycyrrhizin, concentrated, dried, and pulverized to obtain about 2.5 g of powder (sample No. 5).
この試料No、5は水に極めてよく溶け、まろやかな甘
味を有する無臭、無色でほぼ中性の物質である。また、
酸性下においては、グリチルリチンと比較すれば、著し
くゲル形成を起こしにくい物質である。This sample No. 5 is an odorless, colorless, and almost neutral substance that is extremely soluble in water and has a mellow sweet taste. Also,
Under acidic conditions, it is a substance that is significantly less likely to form a gel than glycyrrhizin.
また、メタノール、エタノール、n−ブタノールなどの
低級アルコールには一部溶け、クロロホルムやエチルエ
ーテルには難溶性の物質である。Furthermore, it is a substance that partially dissolves in lower alcohols such as methanol, ethanol, and n-butanol, and is sparingly soluble in chloroform and ethyl ether.
試料No、5のにBr錠剤法による赤外線吸収スペクト
ルを図に示した。この図で840cm−’付近の吸収は
α−結合に特有な吸収であって、原料のグリチルリチン
の場合には見られない吸収である。The infrared absorption spectrum of sample No. 5 obtained by the Br tablet method is shown in the figure. In this figure, the absorption near 840 cm-' is an absorption specific to α-bonds, and is not observed in the case of the raw material glycyrrhizin.
試料No、5の一部を少量の水に溶解した溶液に市販の
結晶グルコアミラーゼ(E C3,2,1,3)を0.
02M酢酸塩!1街液(p H5,0)の存在下のもと
に50℃で作用させて、経時的にサンプリングし、薄層
板(メルク社製造、商品名Kiese1gel F 2
54)にスポットし、展開溶媒、酢酸エチル:メタノー
ル:水=2.5 + 1 : 1の混合溶媒を使用して
上昇法で展開させた。これを乾燥した後、グリチルリチ
ン化合物を紫外線照射で確認し、更に51J/V%バニ
リン50V/V%硫酸メタノール溶液からなる発色剤を
噴霧して発色させた。また、試料No、11No、5お
よびD−グルコースを同様にスポットして比較してみた
。Commercially available crystalline glucoamylase (E C3,2,1,3) was added to a solution in which a portion of sample No. 5 was dissolved in a small amount of water.
02M acetate! It was applied at 50°C in the presence of a liquid solution (pH 5,0), sampled over time, and a thin layer plate (manufactured by Merck & Co., trade name: Kieselgel F2) was applied at 50°C.
54), and was developed by the ascending method using a developing solvent, a mixed solvent of ethyl acetate:methanol:water=2.5+1:1. After drying this, the glycyrrhizin compound was confirmed by ultraviolet irradiation, and a coloring agent consisting of a 51 J/V% vanillin 50 V/V% sulfuric acid methanol solution was sprayed to develop color. In addition, samples No. 11, No. 5, and D-glucose were spotted in the same manner for comparison.
その結果、試料No、5には、試料No、1のグリチル
リチンに相当するRfO,70付近のスポット以外に、
新たにR,0,66、RfO,60,R,0,5?、R
fO,54、RfO,51、RfO,48、R,0,4
4、R,0,40、RfO,34および原点近くに分離
不充分なRfO,22ならびにRfO,11のスポット
が確認できた。As a result, in addition to the spot near RfO, 70, which corresponds to glycyrrhizin in sample No. 1, sample No. 5 had
New R,0,66, RfO,60, R,0,5? ,R
fO,54, RfO,51, RfO,48, R,0,4
4, R,0,40, RfO,34, and insufficiently separated spots of RfO,22 and RfO,11 were confirmed near the origin.
これらの新たなスポットは、グリチルリチン同様に紫外
線照射による蛍光で、紫外線吸収スポットとして確認さ
れ、発色剤で青色に発色した。These new spots, like glycyrrhizin, were confirmed as ultraviolet absorbing spots due to fluorescence caused by ultraviolet irradiation, and were colored blue by the coloring agent.
また、試NHo、5にグルコアミラーゼを作用ざ廿、経
時的にサンプリングして同様にクロマト分析したものは
、反応時間とともに新しいスポットを示す物質が徐々に
加水分解を受け、最終的に青色のR,0,70のスポッ
トを示すグリチルリチンと緑褐色のRfO,57のスポ
ットを示すD−グルコースとになることが判明した。In addition, when glucoamylase was applied to sample NHo, 5, samples were taken over time and chromatographically analyzed in the same way. As the reaction time progressed, the substance showing new spots gradually underwent hydrolysis, and finally the blue R , 0.70 spots, and greenish-brown RfO, D-glucose showing 57 spots.
また、試料No、5にβ−アミラーゼを作用させ、経時
的にサンプリングして同様に薄層クロマト分析したもの
は、反応時間とともにRfO,54以下の新しいスポッ
トを示す物質が徐々に加水分解を受け、最終的に青色の
RfO,70のスポットを示すグリチルリチン、青色の
RfO,66、R,0,60゜R,0,57のスポット
を示す新しい物質および緑褐色のR,0,36のスポッ
トを示すマルトースとなることが判明した。In addition, when sample No. 5 was treated with β-amylase, sampled over time, and similarly thin-layer chromatographically analyzed, the substance showing new spots of RfO, 54 or less gradually underwent hydrolysis with the reaction time. , finally glycyrrhizin showing a blue RfO,70 spot, a new substance showing a blue RfO,66,R,0,60°R,0,57 spot, and a green-brown R,0,36 spot. It turned out to be maltose.
以上の事実から、RfO,66、R,0,60、R,0
,5?、RfO,54、RfO,51、RfO,48、
RfO,44、RfO,40゜R,0,34、RfO,
22、R,0,11などを示す新しい物質は、グリチル
リチンにD−グルコースが等モル以上α−グルコシド結
合しているものと判断きれる。従って、試11No、5
は、シフ0デキストリン・グルカノトランスフェラーゼ
によって新たに生じたRfO,66、RfO,60、R
,0,5?、R,0,54、RfO,51,R,0,4
a、RfO,44、R,0,401RfO,34、R,
0,22、R,0,11を示す新物質と少量の未反応の
グリチルリチンとの混合物である。From the above facts, RfO,66, R,0,60, R,0
,5? , RfO,54, RfO,51, RfO,48,
RfO, 44, RfO, 40°R, 0, 34, RfO,
It can be concluded that new substances exhibiting 22, R, 0, 11, etc. have an equal mole or more of D-glucose bonded to glycyrrhizin by α-glucoside. Therefore, test 11 No. 5
are RfO,66, RfO,60, and RfO, newly generated by Schif0 dextrin glucanotransferase.
,0,5? ,R,0,54,RfO,51,R,0,4
a,RfO,44,R,0,401RfO,34,R,
It is a mixture of a new substance exhibiting 0,22, R, 0,11 and a small amount of unreacted glycyrrhizin.
また、試料No、5と同様にして調製した試料にβ−ア
ミラーゼを作用させたものを用いて、酢酸エチル:メタ
ノール:水=2.5 i 1 + 1の混合溶媒を使用
してシリカゲルカラムクロマトグラフィーを行って、前
述の薄層クロマトグラフィーでRfO,66、R,0,
60、R,0,57のスポットを示す新物質の混合物を
分離し、乾燥して粉末を得た。In addition, using a sample prepared in the same manner as Sample No. 5 and treated with β-amylase, silica gel column chromatography was performed using a mixed solvent of ethyl acetate: methanol: water = 2.5 i 1 + 1. RfO,66, R,0,
A mixture of new substances showing spots of 60, R, 0, 57 was separated and dried to obtain a powder.
本粉末は、試料No、5と同様に水によ(溶け、まろや
かな甘味を有する無臭、無色でほぼ中性の物質である。This powder, like Sample No. 5, is an odorless, colorless, and almost neutral substance that dissolves in water and has a mellow sweet taste.
また、酸性下においては、グリチルリチンと比較すれば
著しくゲル形成を起こしに(い物質である。In addition, under acidic conditions, it is a substance that tends to form a gel significantly compared to glycyrrhizin.
まな、メタノール、エタノール、n−ブタノールなどの
低級アルコールには一部溶け、クロロホルムやエチルエ
ーテルには難溶性の物質である。However, it is partially soluble in lower alcohols such as methanol, ethanol, and n-butanol, but is sparingly soluble in chloroform and ethyl ether.
また、本粉末のKBr錠剤法による赤外線吸収スペクト
ルを求めたところ、試料No、5の場合と同様に、α−
結合に特有な840cm−’付近の吸収が見られた。In addition, when the infrared absorption spectrum of this powder was determined by the KBr tablet method, it was found that α-
Absorption around 840 cm-', which is characteristic of bonding, was observed.
また、これら新物質は、豚の肝臓から抽出し、部分精製
したα−グルコシダーゼによっても同様にグリチルリチ
ンとD−グルコースとに加水分解されることが判明した
。このことから、これら新物質は、人や動物が摂取する
とき、体内でグリチルリチンとD−グルコースとに容易
に分解きれることを示唆している。It has also been found that these new substances can be similarly hydrolyzed into glycyrrhizin and D-glucose by partially purified α-glucosidase extracted from pig liver. This suggests that these new substances can be easily broken down into glycyrrhizin and D-glucose in the body when ingested by humans or animals.
また、試料No、5は、実験2で使用した試料No、3
および試料No、4と同様に、嫌味、薬品臭な(まろや
かな甘味で甘味の発現も早く、残り味の切れもよく、砂
糖に近い優れた甘味を有していることから、本発明のα
−グリコシルグリチルリチン含有製品として好適である
。In addition, sample No. 5 is sample No. 3 used in Experiment 2.
Similar to Sample No. 4, it has a mellow sweetness, a quick onset of sweetness, a good lingering taste, and an excellent sweetness close to that of sugar.
- Suitable as a glycosylglycyrrhizin-containing product.
従って、本発明のグリチルリチンの欠点を解消するとい
う目的は、澱粉質とグリチルリチンとを含有する水溶液
にシクロデキストリン・グルカノトランスフェラーゼを
作用させて澱粉部分分解物とともにα−グリコシルグリ
チルリチンを生成させ、α−グリコシルグリチルリチン
含有製品に変換せしめることによって達成されるものと
判断される。Therefore, the purpose of the present invention to eliminate the drawbacks of glycyrrhizin is to produce α-glycosylglycyrrhizin together with starch partial decomposition products by causing cyclodextrin glucanotransferase to act on an aqueous solution containing starch and glycyrrhizin. It is considered that this can be achieved by converting it into a glycosylglycyrrhizin-containing product.
次に実施例を述べる。Next, an example will be described.
実施例 1 澱粉部分分解物およびα−グリコシルグ
リチルリチン含有製品
バチルス・メガテリウム FERN−P Ho、935
を、実験1−1の培地5Lに植菌し、28℃で3日間通
気撹拌培養した。培養終了後、遠心分離して得た上清に
硫安を0.7飽和にし、更に遠心分離して沈澱を採取し
た。Example 1 Starch partial decomposition product and α-glycosylglycyrrhizin-containing product Bacillus megaterium FERN-P Ho, 935
was inoculated into 5 L of the medium from Experiment 1-1, and cultured with aeration at 28° C. for 3 days. After completion of the culture, the supernatant obtained by centrifugation was made 0.7 saturated with ammonium sulfate, and further centrifuged to collect the precipitate.
この沈澱は、実験1−1に記載する活性の測定方法でシ
クロデキストリン・グルカノトランスフェラーゼ(E
C2,4,1,19)を30万単位含んでいた。This precipitate was used to measure cyclodextrin glucanotransferase (E) using the activity measurement method described in Experiment 1-1.
It contained 300,000 units of C2,4,1,19).
コーンスターチを301J/IJ%、PH6,0で市販
の液化酵素剤を澱粉固形物当り0.2%加え、温度95
乃至98℃連続液化し、90℃で反応を進めてDE20
になった時に液化酵素を加熱失活させた。この液化液に
、精製グリチルリチン(丸善化成株式会社製造、商品名
純グリチミン)を固形物重量でグリチルリチン:澱粉部
分分解物の比が1:3になるように溶解して50℃に冷
却し、これに上記のシクロデキストリン・グルカノトラ
ンスフェラーゼを原料澱粉固形物ダラム当りlO単位の
割合で加え、50℃、1)85.5で48時間反応させ
た。Corn starch was added at 301 J/IJ% and a commercially available liquefied enzyme agent was added at 0.2% based on the starch solids at a pH of 6.0, and the temperature was 95%.
Continuous liquefaction at 98°C and reaction at 90°C until DE20
The liquefaction enzyme was inactivated by heating. Purified glycyrrhizin (manufactured by Maruzen Kasei Co., Ltd., trade name: pure glycimin) was dissolved in this liquefied liquid so that the ratio of glycyrrhizin to starch partial decomposition product was 1:3 by solid weight, and the mixture was cooled to 50°C. The above-mentioned cyclodextrin glucanotransferase was added at a rate of 10 units per duram of raw starch solids, and the mixture was reacted at 50° C. and 1) 85.5 ml for 48 hours.
反応液の酵素を加熱失活きせて濾過した後、濾液にケイ
酸アルミン酸マグネシウム(富士化学工業株式会社製造
、商品名ノイシリン)を原料澱粉固形物当り0.3%加
え、徐々に撹拌しつつ30分間保った後、濾過し、次い
で減圧濃縮、乾燥、粉末化して、粉末状の澱粉部分分解
物およびα−グリコシルグリチルリチン含有製品を固形
物収率的95%で得た。減圧濃縮中の発泡は極めて抑制
されていた。After inactivating the enzyme in the reaction solution by heating and filtering it, magnesium aluminate silicate (manufactured by Fuji Chemical Industry Co., Ltd., trade name: Neusilin) was added to the filtrate in an amount of 0.3% based on the solid material starch, and the mixture was gradually stirred. After keeping for 30 minutes, the mixture was filtered, concentrated under reduced pressure, dried, and powdered to obtain a powdered starch partial decomposition product and α-glycosylglycyrrhizin-containing product with a solid yield of 95%. Foaming during vacuum concentration was extremely suppressed.
本製品は、吸湿性が少な(、取扱いが容易である。また
、水に対する溶解速度は極めて大きく、冷水に容易に溶
け、また溶解量も非常に大で、本製品がペースト状にな
る程の高濃度にまで容易に溶けた。This product has low hygroscopicity (and is easy to handle). Also, the dissolution rate in water is extremely high, easily dissolving in cold water, and the amount of dissolution is extremely large, so that the product becomes paste-like. Easily dissolved to high concentrations.
本製品は、固形物当りの甘味度が砂糖の約25倍であっ
て、甘味の質もまろやかで残り味の切れもよい。本製品
は、甘味付けまたは呈味改良を必要とするあらゆる場合
に利用できるが、中でも低カロリー甘味料、低う触性甘
味料などとして好適である。The sweetness of this product per solid substance is about 25 times that of sugar, and the quality of the sweetness is mellow and the residual taste is easy to cut through. This product can be used in any case that requires sweetening or taste improvement, but is particularly suitable as a low-calorie sweetener, a low-cariogenic sweetener, etc.
また、本製品は、泡立ちが極度に抑制きれ、呈味改良効
果も高いので、例えば、醤油、麺つゆ、飲料などの液状
飲食物、ハードキャンデー佃煮などの煮詰工程を必要と
する飲食物、ドリンク剤、シロップなどの液状医薬品な
どへの用途に有利に利用できる。In addition, this product can extremely suppress foaming and has a high taste improvement effect, so it can be used for liquid foods such as soy sauce, noodle soup, and beverages, as well as for foods and beverages that require a boiling process such as hard candy tsukudani. It can be advantageously used for liquid pharmaceuticals such as drugs and syrups.
実施例 2 α−グリコシルグリチルリチン含有製品
β−シクロデキストリン500gとグリチルリチン酸三
ナトリウム(東京化成株式会社製造) 100gとを水
5Lに加熱溶解し、60℃に冷却してpH5,5に調整
し、これに実験1の方法で調製したシクロデキストリン
・グルカノトランスフェラーゼをβ−シクロデキストリ
ン固形物ダラム当り100単位の割合で加え、60℃、
pH5,5に24時間保った。Example 2 α-Glycosylglycyrrhizin-containing product 500 g of β-cyclodextrin and 100 g of trisodium glycyrrhizinate (manufactured by Tokyo Kasei Co., Ltd.) were heated and dissolved in 5 L of water, cooled to 60°C, adjusted to pH 5.5, and dissolved. Cyclodextrin glucanotransferase prepared by the method of Experiment 1 was added at a rate of 100 units per solid duram of β-cyclodextrin, and the mixture was heated at 60°C.
The pH was kept at 5.5 for 24 hours.
反応液の酵素を加熱失活させて濾過した後、濾液にマグ
ネシア系吸着剤(北海道曹達株式会社製造、商品名M
−511) 2gを加え、徐々に撹拌しつつ30分間保
ち、次いで、濾過し得られた濾液を、合成吸着剤(ロー
ム&ハース社製造、商品名XAD−7)4Lを充填した
カラムに通液し、このカラムを充分水洗して遊離の澱粉
部分分解物を除去した。次いで、このカラムに50V/
V%エタノールIOLを通してα−グリコシルグリチル
リチンを溶出し、濃縮、乾燥して約150gの粉末状の
α−グリコシルグリチルリチン含有製品を得た。After inactivating the enzyme in the reaction solution by heating and filtering it, the filtrate is treated with a magnesia-based adsorbent (manufactured by Hokkaido Soda Co., Ltd., trade name: M).
-511) 2g was added, kept for 30 minutes while stirring gradually, and then filtered, and the resulting filtrate was passed through a column filled with 4L of synthetic adsorbent (manufactured by Rohm & Haas, trade name: XAD-7). Then, the column was thoroughly washed with water to remove free starch partial decomposition products. This column was then energized at 50V/
α-Glycosylglycyrrhizin was eluted through the V% ethanol IOL, concentrated and dried to obtain about 150 g of a powdered α-glycosylglycyrrhizin-containing product.
水晶を実験3の試料No、5の場合と同様に薄層クロマ
トグラフィーで調べたところ、RfO,70付近の小ス
ポットを示すグリチルリチン以外に、新たにRfO,6
7付近、R,0,59付近のスポットを示す物質、更に
原点からR,0,26付近に至る分離不充分で巨大なス
ポットを示す物質などがシクロデキストリン令グルカノ
トランスフェラーゼによって生成していることが確認さ
れた。また、試料No、5の場合と同様・に、これら新
しい物質はグルコアミラーゼによってグリチルリチンと
D−グルコースとに徐々に加水分解されることも確認さ
れた。When the crystal was examined by thin layer chromatography in the same manner as in Samples No. 5 of Experiment 3, it was found that in addition to glycyrrhizin, which showed a small spot near RfO, 70, new
Substances that show spots near R, 7, R, 0, 59, and insufficiently separated and huge spots from the origin to R, 0, 26 are generated by cyclodextrin-aged glucanotransferase. was confirmed. Furthermore, as in the case of Sample No. 5, it was also confirmed that these new substances were gradually hydrolyzed into glycyrrhizin and D-glucose by glucoamylase.
本製品は、固形物当りの甘味度が砂糖の約60倍であっ
て、甘味の質もまろやかで、残り味の切れもよい。従っ
て、各種飲食物、嗜好物など多方面への甘味付け、呈味
改良などに有利に利用でざる。また、実施例1の場合と
同様に、低カロリー甘味料、低う触性甘味料などとして
利用することも随意である。This product has a sweetness level of about 60 times that of sugar per solid substance, has a mellow sweetness, and has a good lingering taste. Therefore, it can be advantageously used for sweetening various foods, drinks, luxury foods, etc., and improving taste. Further, as in the case of Example 1, it is optional to use it as a low-calorie sweetener, a low-cariogenic sweetener, etc.
実施例 3I!!粉部分分解物およびα−グリコシルグ
リチルリチン含有製品
マルトデキストリン(D E 18) 100gと純グ
リチルリチンを約25%しか含有せず黄褐色をしたグリ
チルリチン粗製品(丸善化成株式会社製造、商品名リコ
ゲン) 100gとを水3Lに加熱溶解しな後、60℃
に冷却し、pH5,5に調整した。これに実験1の方法
で調製したシクロデキストリン・グルカノトランスフェ
ラーゼ標品の3.000単位を加え、p H5,5,6
0℃に維持しつつ44時間反応させた。この反応液を加
熱して酵素を失活ぎせた後濾過し、濾液に実施例2の場
合に用いたマグネシア系吸着剤5gを加え、徐々に撹拌
しつつ20分間保ち、次いで濾過し得られた濾液を、減
圧濃縮し、水分sowiw%の淡黄色液状(シラツブ状
)の澱粉部分分解物およびα−グリコシルグリチルリチ
ン含有製品を原料固形物当り約97%の収率で得た。減
圧濃縮中の発泡は極めて抑制されていた。Example 3I! ! Powder partial decomposition products and α-glycosylglycyrrhizin-containing products: 100 g of maltodextrin (D E 18) and 100 g of a yellow-brown glycyrrhizin crude product containing only about 25% pure glycyrrhizin (manufactured by Maruzen Kasei Co., Ltd., trade name: Licogen). After heating and dissolving in 3L of water, 60℃
The mixture was cooled to pH 5.5. Add 3,000 units of the cyclodextrin glucanotransferase preparation prepared by the method in Experiment 1 to this, and adjust the pH to 5, 5, 6.
The reaction was carried out for 44 hours while maintaining the temperature at 0°C. This reaction solution was heated to inactivate the enzyme, and then filtered. 5 g of the magnesia-based adsorbent used in Example 2 was added to the filtrate, kept for 20 minutes with gradual stirring, and then filtered. The filtrate was concentrated under reduced pressure to obtain a starch partial decomposition product and α-glycosylglycyrrhizin-containing product in the form of a light yellow liquid (silk) with a moisture content of sowiw% at a yield of about 97% based on the solid material. Foaming during vacuum concentration was extremely suppressed.
本製品は、精製グリチルリチンを用いる場合以上に甘味
の質の改良の著しいことがわかった。It was found that this product significantly improved the quality of sweetness compared to when purified glycyrrhizin was used.
本製品の甘味度は、砂糖の約4倍であって、各種飲食物
、嗜好物、医薬品などの甘味付け、呈味改良などに有利
に利用できる。The sweetness of this product is about four times that of sugar, and it can be advantageously used to sweeten various foods, luxury foods, medicines, etc., and improve the taste.
本製品の製造には、原料の粗グリチルリチンからの有色
夾雑物の完全除去にやや難点があるが、色にこだわらな
い、例えば、醤油、ソース、味噌、マヨネーズ、焼肉の
なれ、スープの素などの調味料、福神漬、沢庵漬、奈良
漬などの漬物類、チョコレート、ココア、チューインガ
ム、プリン、あんなどの菓子類、その他佃煮、珍味、塩
辛、乳酸飲料などの製造には高度に精製したグリチルリ
チンを用いる場合よりも安価に大量に供給できるので好
都合である。Although there is a slight difficulty in the complete removal of colored impurities from the raw material crude glycyrrhizin in the production of this product, it can be used in products that are not particular about color, such as soy sauce, sauce, miso, mayonnaise, yakiniku sauce, soup stock, etc. Highly purified glycyrrhizin is used in the production of seasonings, pickles such as Fukujinzuke, Takuanzuke, and Narazuke, chocolate, cocoa, chewing gum, pudding, confectionery such as Anna, and other foods such as tsukudani, delicacies, salted fish, and lactic acid drinks. This is advantageous because it can be supplied in large quantities at a lower cost.
また、本製品は泡立ちが極度に抑制され、呈味改良効果
も高いので、例えば、醤油、麺つゆ、飲料などの液状飲
食物、ハードキャンデー、佃煮などの煮詰め工程を必要
とする飲食物、ドリンク剤、シロップなどの液状医薬品
などへの用途に有利に実施できる。In addition, this product extremely suppresses foaming and has a high taste improvement effect, so it can be used for liquid foods such as soy sauce, noodle soup, and drinks, as well as for foods and drinks that require a boiling process such as hard candy and tsukudani. This method can be advantageously applied to liquid pharmaceuticals such as drugs and syrups.
実施例 4 甘 昧 籾
還元麦芽糖水飴(株式会社林原生物化学研究所製造、商
品名マビット) 1kgに実施例1の方法で製造した澱
粉部分分解物およびα−グリコシルグリチルリチン含有
製品10gを溶解して調製した液状甘味料は、甘味の質
が優れ、砂糖と同程度の甘味を有し、カロリーは砂糖の
約1720である。Example 4 Sweet rice reduced maltose starch syrup (manufactured by Hayashibara Biochemical Research Institute Co., Ltd., trade name Mavit) Prepared by dissolving 10 g of the starch partial decomposition product produced by the method of Example 1 and α-glycosylglycyrrhizin-containing product in 1 kg. The liquid sweetener has excellent sweetness, has a sweetness comparable to that of sugar, and has about 1,720 calories compared to sugar.
本甘味料は、低カロリー甘味料としてカロリー摂取を制
限をしている人、例えば、肥満者、糖尿病者などのため
の、低カロリー飲食物、嗜好物の甘味付けに好適であり
、またこのままテーブルシラツブとしても自由に利用で
きる。また、虫歯原因菌によって酸の生成もなく、水不
溶性グルカンの生成もないことより、虫歯を予防する飲
食物などへの甘味付けに好適である。As a low-calorie sweetener, this sweetener is suitable for sweetening low-calorie drinks and favorite foods for people who are restricting their calorie intake, such as obese people and diabetics. It can also be freely used as a bookmark. In addition, since it does not produce acid or water-insoluble glucan by caries-causing bacteria, it is suitable for sweetening foods and drinks that prevent dental caries.
実施例 5 甘 味 料
グルコース800gに、砂1f!200g1実施例2の
方法で製造したα−グリコシルグリチルリチン含有製品
5gとを均一に混合して粉末化したものに、少量の水を
スプレーしてかる(圧縮して成形し、角砂糖様形状の甘
味料を製造した。Example 5 800g of sweetener glucose and 1f of sand! A small amount of water is sprayed onto a mixture of 200 g and 5 g of the α-glycosylglycyrrhizin-containing product produced by the method of Example 2, and then sprayed with a small amount of water. was manufactured.
本甘味料は、砂糖とほぼ同程度の甘味度を有すると同時
に、極めて優れた甘味質を持っていて、冷水にも容易に
溶ける。冷水に溶かしたものは、そのままでも清涼飲料
水に好適である。This sweetener has almost the same degree of sweetness as sugar, has extremely excellent sweetness, and is easily soluble in cold water. When dissolved in cold water, it is suitable as a soft drink.
本甘味料の甘味の質が優れているのは、これら混合した
三つの甘味源の相乗効果と判断された。The excellent quality of sweetness of this sweetener was judged to be due to the synergistic effect of these three sweetness sources mixed together.
実施例 6 甘 味 料
実施例2の方法で製造したα−グリコシルグリチルリチ
ン含有製品lagを水20社に溶かσ込み、これに蜂蜜
IKgを均一に混合して複合甘味料を得た。Example 6 Sweetener The α-glycosylglycyrrhizin-containing product lag produced by the method of Example 2 was dissolved in water and mixed with Ikg of honey uniformly to obtain a composite sweetener.
本甘味料は、甘、昧度が砂糖の約2倍であって、甘味の
質も極めて優れており、蜂蜜の香りを一段とひき立たせ
た。The sweetness and sourness of this sweetener were approximately twice that of sugar, and the quality of the sweetness was also extremely excellent, further enhancing the aroma of honey.
本甘味料は、美容飲料、i1康食品、ダイエツトフード
などへのせ味付や医薬品などの矯味剤などに有利に利用
できる。The present sweetener can be advantageously used as a flavoring agent for beauty drinks, health foods, diet foods, etc., and as a flavoring agent for pharmaceuticals.
実施例 7 ハードキャンデー
還元麦芽糖水飴(株式会社林原生物化学研究所製造、商
品名マビット) 15kgに実施例1の方法で製造した
澱粉部分分解物およびα−グリコシルグリチルリチン含
有製品Bogを溶解した後、減圧下で水分が約2%以下
になるまで加熱濃縮し、これにクエン酸150gおよび
少量のレモン香料と着色料とを混和し、次いで、常法に
従って成形しハードキャンデーを得た。グリチルリチン
を使用する場合と比較して、加熱濃縮時の泡立ちは極p
で抑制、されていた。Example 7 Hard candy reduced maltose starch syrup (manufactured by Hayashibara Biochemical Research Institute Co., Ltd., trade name Mavit) After dissolving the starch partial decomposition product and α-glycosylglycyrrhizin-containing product Bog produced by the method of Example 1 in 15 kg, the mixture was reduced under reduced pressure. The mixture was heated and concentrated until the moisture content was reduced to about 2% or less, and 150 g of citric acid and a small amount of lemon flavor and coloring were mixed therein, and then molded according to a conventional method to obtain a hard candy. Compared to using glycyrrhizin, foaming during heating and concentration is extremely low.
It was suppressed.
本品は、高甘味、低カロリー、低う練性のハードキャン
デーである。This product is a hard candy with high sweetness, low calories, and low chewability.
実施例 8 チューインガム
ガムベース2kgを柔らかくなる程度に加熱溶融し、こ
れにう・クチトール(結晶粉末) 6kg、実施例2の
方法で製造したα−グリコシルグリチルリチン含有製品
160g 、ソルビトール(結晶粉末)1kgおよび少
量のハツカ香料と着色料とを混合した後、常法に従って
、ロールにより練り合せ、成型することによってチュー
インガムを得た。Example 8 2 kg of chewing gum gum base was heated and melted to the extent that it became soft, followed by 6 kg of cutitol (crystalline powder), 160 g of the α-glycosylglycyrrhizin-containing product produced by the method of Example 2, 1 kg of sorbitol (crystalline powder), and a small amount. A chewing gum was obtained by mixing the peppermint flavor and coloring agent, then kneading and molding with a roll according to a conventional method.
本品は、テクスチャー、甘味ともに良好で、低カロリー
、低う練性のチューインガムである。This product is a chewing gum that has good texture and sweetness, and is low in calories and chewable.
実施例 9 チョコレート
カカオペースト40kg 1力カオバター10kg、麦
芽糖10Kg、乳糖5Kg 、全脂粉乳20Kgおよび
実施例1の方法で製造した澱粉部分分解物およびα−グ
リコシルグリチルリチン含有製品1にgを混合し、レフ
ァイナーを通した。そして粒度を下げた後、コンチエに
入れてレシチン500gを加え、50℃で二昼夜練り上
げた。次いで、常法に従い成型機に流し込み固化成型す
ることにより製品とした。Example 9 40 kg of chocolate cacao paste, 10 kg of cacao butter, 10 kg of maltose, 5 kg of lactose, 20 kg of whole milk powder, and 1 g were mixed with starch partial decomposition product and α-glycosylglycyrrhizin-containing product 1 produced by the method of Example 1, and processed into a refiner. passed through. After reducing the particle size, the mixture was placed in a contier, 500 g of lecithin was added, and the mixture was kneaded at 50°C for two days and nights. Next, the mixture was poured into a molding machine and solidified and molded according to a conventional method to obtain a product.
本品は、泡の混入、ファツトブルームおよびシュガーブ
ルームの恐れがなく、舌にのせた時の融は具合、風味と
もに良好で、低う練性のチョコレートである。This product has no fear of bubbles, fat bloom, or sugar bloom, has a good melting texture and flavor when placed on the tongue, and is a low-plastic chocolate.
実施例10乳酸飲料
10kgの脱脂乳を80℃で20分間加熱殺菌した後、
40℃に冷却し、これにスターター300gを加え35
乃至37℃で10時間発酵させた。次いで、これをホモ
ゲナイズした後、実施例1の方法で製造した澱粉部分分
解物およびα−グリコシルグリチルリチン含有製品2K
gとカップリングシュガー2kgとを加え80乃至85
℃で撹拌混合しつつ殺菌した。Example 10 Lactic acid drink After heat sterilizing 10 kg of skim milk at 80°C for 20 minutes,
Cool to 40℃ and add 300g of starter to it
Fermentation was carried out at 37°C to 37°C for 10 hours. Next, after homogenizing this, the starch partial decomposition product and α-glycosylglycyrrhizin-containing product 2K produced by the method of Example 1
Add 2 kg of coupling sugar and 80 to 85 g.
The mixture was sterilized at ℃ while stirring and mixing.
これを冷却した後、少量の香料を加えてピン詰めし、製
品とした。After cooling, a small amount of fragrance was added and the product was packed into pins.
本品は、泡立ちもなく、風味良好な低う練性の乳酸飲料
である。This product is a low-plastic lactic acid drink with no foaming and good flavor.
実施例 11 佃 煮
常法に従って、砂取り、酸処理して角切りした昆布25
0gに、醤油212mL、アミノ酸液318吐、粉飴5
0g1プルラン1gおよび実施例3の方法で製造した澱
粉部分分解物およびα−グリコシルグリチルリチン含有
製品10gを加えて煮込みつつ、更にグルタミン酸ソー
ダ12g1カラメル8g、みりん21社を加えて炊き上
げ、昆布の佃煮を得た。Example 11 Tsukuda 25 pieces of kelp diced after sand removal and acid treatment according to the usual boiling method
0 g, 212 mL of soy sauce, 318 mL of amino acid solution, 5 powdered candy
1 g of pullulan and 10 g of the starch partial decomposition product and α-glycosylglycyrrhizin-containing product produced by the method of Example 3 were added and simmered, and 12 g of sodium glutamate, 8 g of caramel, and 21 mirin were added and boiled to make kelp tsukudani. Obtained.
グリチルリチンを使用する場合と比較して、煮込時の泡
立ちは極めて抑制きれていた。Compared to the case of using glycyrrhizin, foaming during boiling was extremely suppressed.
本品は、味、香りだけでなく、色、艶も充分で食欲をそ
そる商品価値の高い製品であった。This product not only had a good taste and aroma, but also a good color and luster, and was an appetizing product with high commercial value.
実施例 12 ラッキョウ漬
生ラッキョウ5Kgを、常法に従って、約20%食塩水
2.5しに塩漬けして3週間の後、水切りして得た塩漬
ラッキョウを水2.OL、氷酢酸80mL s食塩80
gからなる酢酸液に1ケ月間酢漬けした。Example 12 Pickled Rakkyo 5 kg of raw rakkyo was pickled in about 2.5 kg of 20% saline according to a conventional method.After 3 weeks, the salted rakkyo obtained by draining the water was soaked in 2.5 kg of water. OL, glacial acetic acid 80mL s salt 80
It was pickled in vinegar for one month in an acetic acid solution consisting of g.
得られた酢漬ラッキョウを、更に食酢800■L1みり
ん400mL 、唐辛子10gおよび実施例2の方法で
製造したα−グリコシルグリチルリチン含有製品log
からなる調味液に10日間漬けて風味豊かなラッキョウ
のせ酢潰を得た。The obtained pickled rakkyo was further mixed with 800 ml of vinegar, 400 ml of mirin, 10 g of chili pepper, and a log of the α-glycosylglycyrrhizin-containing product produced by the method of Example 2.
A flavorful rakkyo topped with vinegar was obtained by soaking it in a seasoning liquid for 10 days.
実施例 13 錠 剤
アスピリン50gに、麦芽糖13g1コーンスターチ4
gおよび実施例2の方法で製造したα−グリコシルグリ
チルリチン含有製品1gを均一に混合した後、直径12
−瞳、20R杵を用いて1錠680mg1錠剤の厚き5
.25mm、硬度8kg±1kgで打錠した。Example 13 Tablets 50g of aspirin, 13g of maltose, 4g of cornstarch
g and 1 g of the α-glycosylglycyrrhizin-containing product produced by the method of Example 2 were mixed uniformly, and then
- Pupil, 1 tablet 680mg 1 tablet thickness 5 using 20R pestle
.. It was compressed into tablets of 25 mm and a hardness of 8 kg±1 kg.
水晶は、適度の甘味を有する飲み易い錠剤である。Quartz is an easy-to-swallow tablet with a moderate sweetness.
実施例 14 練 歯 磨
配合
第2リン酸力ルシウム
プ ル ラ ン
ラウリル硫酸ナトリウム
グ リ セ リ ン
ポリオキ9エチレン ソルビタンモノラウレート防
腐 剤
実施例2の方法で製造したα−グ
リコジルグリチルリチン含有製品
45.0
2.75
1.5
0.5
0.05
0.2
水 30
.0 %上記の材料を常法に従って混合し、練歯磨を得
た。Example 14 Toothpaste formulation Dibasic phosphate lucium chloride Sodium lauryl sulfate Glycerin Polyoxy 9 ethylene Sorbitan monolaurate
α-Glycodylglycyrrhizin-containing product produced by the method of Preservative Example 2 45.0 2.75 1.5 0.5 0.05 0.2 Water 30
.. 0% The above materials were mixed according to a conventional method to obtain a toothpaste.
水晶は適度の甘味を有しており、子供用練歯磨として利
用できる。Quartz has a moderate sweetness and can be used as a toothpaste for children.
図は、実験3で得た試料No、5の赤外線吸収スペクト
ル図を示す。The figure shows infrared absorption spectra of samples No. 5 obtained in Experiment 3.
Claims (4)
フェラーゼを作用させるに際し、澱粉質とともにグリチ
ルリチンを含有する水溶液にシクロデキストリン・グル
カノトランスフェラーゼを作用させることを特徴とする
澱粉質の反応方法。(1) A method for reacting starch, which comprises allowing cyclodextrin/glucanotransferase to act on an aqueous solution containing glycyrrhizin together with starch.
にシクロデキストリン・グルカノトランスフェラーゼを
作用させるに際し、澱粉質をグリチルリチンに対して固
形物当り約0.5乃至500倍の範囲にして、シクロデ
キストリン・グルカノトランスフェラーゼを作用させる
ことを特徴とする特許請求の範囲第(1)項記載の澱粉
質の反応方法。(2) When cyclodextrin glucanotransferase is allowed to act on an aqueous solution containing glycyrrhizin as well as starch, the amount of starch is about 0.5 to 500 times that of glycyrrhizin per solid substance, and cyclodextrin glucanotransferase is The method for reacting starch according to claim (1), characterized in that a transferase is allowed to act.
にシクロデキストリン・グルカノトランスフェラーゼを
作用させ、澱粉部分分解物とともにα−グリコシルグリ
チルリチンを生成せしめ、これを採取することを特徴と
する澱粉部分分解物およびα−グリコシルグリチルリチ
ン含有製品の製造方法。(3) Starch partial decomposition product and α-glycosylglycyrrhizin are produced together with starch partial decomposition product by causing cyclodextrin glucanotransferase to act on an aqueous solution containing glycyrrhizin together with starch, and collecting the α-glycosylglycyrrhizin product. - A method for producing a glycosylglycyrrhizin-containing product.
にシクロデキストリン・グルカノトランスフェラーゼを
作用させ、得られる澱粉部分分解物およびα−グリコシ
ルグリチルリチン含有製品を含有せしめることを特徴と
する飲食物の製造方法。(4) A method for producing a food or drink, which comprises making an aqueous solution containing starch and glycyrrhizin act with cyclodextrin glucanotransferase, and containing the obtained starch partial decomposition product and an α-glycosylglycyrrhizin-containing product.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1336707A JPH02219585A (en) | 1989-12-27 | 1989-12-27 | Reaction of starch substance and preparation and use of reaction product thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1336707A JPH02219585A (en) | 1989-12-27 | 1989-12-27 | Reaction of starch substance and preparation and use of reaction product thereof |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP56095714A Division JPS58870A (en) | 1981-06-20 | 1981-06-20 | Method of sweetening food or beverage |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2298542A Division JPH03164193A (en) | 1990-11-03 | 1990-11-03 | Partially decomposed starch containing alpha-glycosyl-glycyrrhizin, its production and use thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH02219585A true JPH02219585A (en) | 1990-09-03 |
JPH0336518B2 JPH0336518B2 (en) | 1991-05-31 |
Family
ID=18301963
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1336707A Granted JPH02219585A (en) | 1989-12-27 | 1989-12-27 | Reaction of starch substance and preparation and use of reaction product thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02219585A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2006022173A1 (en) * | 2004-08-23 | 2008-05-08 | 株式会社林原生物化学研究所 | Moisturizer containing α-glycosylglycyrrhizin as an active ingredient and use thereof |
-
1989
- 1989-12-27 JP JP1336707A patent/JPH02219585A/en active Granted
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2006022173A1 (en) * | 2004-08-23 | 2008-05-08 | 株式会社林原生物化学研究所 | Moisturizer containing α-glycosylglycyrrhizin as an active ingredient and use thereof |
JP4982644B2 (en) * | 2004-08-23 | 2012-07-25 | 株式会社林原 | Moisturizer containing α-glycosylglycyrrhizin as an active ingredient and use thereof |
Also Published As
Publication number | Publication date |
---|---|
JPH0336518B2 (en) | 1991-05-31 |
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