JP2820945B2 - Method for removing bitterness of glycyrrhizin-containing liquid - Google Patents
Method for removing bitterness of glycyrrhizin-containing liquidInfo
- Publication number
- JP2820945B2 JP2820945B2 JP1029297A JP2929789A JP2820945B2 JP 2820945 B2 JP2820945 B2 JP 2820945B2 JP 1029297 A JP1029297 A JP 1029297A JP 2929789 A JP2929789 A JP 2929789A JP 2820945 B2 JP2820945 B2 JP 2820945B2
- Authority
- JP
- Japan
- Prior art keywords
- glycyrrhizin
- product
- present
- solution
- bitterness
- 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.)
- Expired - Fee Related
Links
- 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 title claims description 94
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 title claims description 92
- 229960004949 glycyrrhizic acid Drugs 0.000 title claims description 92
- 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 title claims description 92
- 235000019410 glycyrrhizin Nutrition 0.000 title claims description 92
- 239000004378 Glycyrrhizin Substances 0.000 title claims description 91
- 235000019658 bitter taste Nutrition 0.000 title claims description 40
- 239000007788 liquid Substances 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 10
- 239000000126 substance Substances 0.000 claims description 30
- 229920002472 Starch Polymers 0.000 claims description 19
- 239000008107 starch Substances 0.000 claims description 19
- 235000019698 starch Nutrition 0.000 claims description 19
- 229940069445 licorice extract Drugs 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 claims description 2
- 244000303040 Glycyrrhiza glabra Species 0.000 claims 1
- 235000011477 liquorice Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 description 74
- 239000000243 solution Substances 0.000 description 43
- 108090000790 Enzymes Proteins 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 12
- 235000019606 astringent taste Nutrition 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 9
- 235000019640 taste Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 102100022624 Glucoamylase Human genes 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 241000193830 Bacillus <bacterium> Species 0.000 description 4
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 4
- 229920001353 Dextrin Polymers 0.000 description 4
- 239000004375 Dextrin Substances 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 235000019425 dextrin Nutrition 0.000 description 4
- 230000035622 drinking Effects 0.000 description 4
- 229940088679 drug related substance Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000193752 Bacillus circulans Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 102220547770 Inducible T-cell costimulator_A23L_mutation Human genes 0.000 description 2
- 238000011481 absorbance measurement Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000013555 soy sauce Nutrition 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 241000194107 Bacillus megaterium Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 241000202807 Glycyrrhiza Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 etc. Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 239000001685 glycyrrhizic acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 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 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- General Preparation And Processing Of Foods (AREA)
- Seasonings (AREA)
Description
【発明の詳細な説明】 発明の技術分野 本発明は、グリチルリチン含有液の苦味除去方法に関
し、さらに詳しくは、グリチルリチン含有液の甘味を保
持しつつ苦味だけを除去することができるようなグリチ
ルリチン含有液の苦味除去方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for removing bitterness of a glycyrrhizin-containing liquid, and more particularly, to a glycyrrhizin-containing liquid capable of removing only bitterness while maintaining the sweetness of the glycyrrhizin-containing liquid. And a method for removing bitterness.
発明の技術的背景ならびにその問題点 従来、甘草から抽出された甘草エキスなどのグリチル
リチン含有液は苦味・渋味（以下単に苦味という）を有
するため、このグリチルリチン含有液の精製法に関して
種々報告されている（特開昭52−139,710号公報、特開
昭56−51,500号公報など）。またたとえば、特開昭58−
870号公報には、グリチルリチンと澱粉質とを含有する
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、α−グルコシルグリチルリチンを含む
反応混合物を得ることにより、グリチルリチンが有する
苦味および他の異味などを除去するための方法が開示さ
れており、このようにして得られたα−グルコシルグリ
チルリチンを含有する反応混合物は、飲食物などに用い
ることができると教示されている。Technical Background of the Invention and Problems Thereof Conventionally, since glycyrrhizin-containing liquids such as licorice extract extracted from licorice have bitterness / astringency (hereinafter, simply referred to as bitterness), various reports have been made on methods for purifying glycyrrhizin-containing liquids. (JP-A-52-139,710, JP-A-56-51,500, etc.). In addition, for example, see
No. 870 discloses that a cyclodextrin glucanotransferase is acted on an aqueous solution containing glycyrrhizin and starch to obtain a reaction mixture containing α-glucosylglycyrrhizin, thereby removing bitterness and other off-flavors of glycyrrhizin. And that the reaction mixture containing α-glucosylglycyrrhizin thus obtained can be used for food and drink.
しかしながら、この特開昭58−870号公報に記載され
ているような方法によれば、グリチルリチン含有液から
苦味等が除去されるのみならず、グリチルリチン含有液
の甘味までも低下されてしまうという問題点があった。However, according to the method described in JP-A-58-870, not only the bitterness and the like are removed from the glycyrrhizin-containing solution, but also the sweetness of the glycyrrhizin-containing solution is reduced. There was a point.
このような問題点を解決すべく本発明者らは検討した
ところ、グリチルリチン自身は苦味を全く有しておら
ず、またグリチルリチンをα−グルコシル化して得られ
るα−グルコシル化グリチルリチンは全く甘味も苦味も
有していないことを見出した。そして上記のような知見
に基いて本発明者らはさらに検討したところ、甘草エキ
スなどのグリチルリチン含有液が苦味を有するのは、グ
リチルリチン以外の苦味物質が存在するためであり、し
かもこの苦味物質はグリチルリチンよりも容易にα−グ
ルコシル化されやすいことを見出した。本発明者らは、
さらに上記のような知見に基いて検討したところ、上記
のような苦味物質を含有するグリチルリチン含有液に澱
粉質の存在下でα−グルコシル転移酵素をグリチルリチ
ンのα−グルコシル化率が５％以下であるように作用さ
せれば、グリチルリチン含有液中の苦味物質はほとんど
α−グルコシル化されるのに対し、グリチルリチンはほ
とんどα−グルコシル化されないため、グリチルリチン
含有液の甘味を保持しつつ苦味だけを除去しうることを
見出して本発明を完成するに至った。The present inventors have studied to solve such problems and found that glycyrrhizin itself has no bitter taste, and α-glucosylated glycyrrhizin obtained by α-glucosylation of glycyrrhizin has no sweetness or bitterness. Not even have. And based on the above findings, the present inventors further studied, the glycyrrhizin-containing solution such as licorice extract has a bitter taste is due to the presence of bitter substances other than glycyrrhizin, and moreover, this bitter substance is It has been found that α-glucosylation is more easily performed than glycyrrhizin. We have:
Further investigations based on the above findings show that α-glucosyltransferase can be added to a glycyrrhizin-containing solution containing the above-mentioned bitter substance in the presence of starch in which the α-glucosylation rate of glycyrrhizin is 5% or less. By acting as such, bitter substances in the glycyrrhizin-containing liquid are almost α-glucosylated, whereas glycyrrhizin is hardly α-glucosylated, so that only the bitterness is removed while maintaining the sweetness of the glycyrrhizin-containing liquid. The inventors have found that the present invention can be performed, and have completed the present invention.
発明の目的 本発明は、上記のような従来技術における問題点を解
決しようとするものであって、甘草エキスなどのグリチ
ルリチン含有液の甘味を保持しつつ苦味だけを除去する
ことができるようなグリチルリチン含有液の苦味除去方
法を提供することを目的としている。An object of the present invention is to solve the problems in the prior art as described above, and a glycyrrhizin capable of removing only bitterness while maintaining the sweetness of a glycyrrhizin-containing solution such as a licorice extract. It is an object of the present invention to provide a method for removing the bitterness of a contained liquid.
発明の概要 本発明に係るグリチルリチン含有液の苦味除去方法
は、グリチルリチンおよびα−グルコシル化可能な甘草
エキス由来の苦味物質を含むグリチルリチン含有液と、
澱粉質との混合物に、α−グルコシル転移酵素を作用さ
せ、グリチルリチン含有液中に含まれる苦味物質をα−
グルコシル化するとともにグリチルリチンのα−グルコ
シル化率を５％以下さらに好ましくは３％以下特に好ま
しくは０％に抑えることを特徴としている。SUMMARY OF THE INVENTION A method for removing bitterness of a glycyrrhizin-containing liquid according to the present invention includes a glycyrrhizin-containing liquid containing glycyrrhizin and a bitter substance derived from an α-glucosylatable licorice extract,
Α-Glucosyltransferase is allowed to act on the mixture with starch to remove the bitter tastant contained in the glycyrrhizin-containing solution by α-glucosyltransferase.
It is characterized in that the glucosylation and the α-glucosylation rate of glycyrrhizin are suppressed to 5% or less, more preferably 3% or less, and particularly preferably 0%.
本発明によれば、苦味物質を含有するグリチルリチン
含有液から甘味を低下させることなく苦味だけを効率よ
く除去することができる。According to the present invention, only bitterness can be efficiently removed from a glycyrrhizin-containing liquid containing a bitter substance without reducing sweetness.
発明の具体的説明 以下本発明に係るグリチルリチン含有液の苦味除去方
法について具体的に説明する。DETAILED DESCRIPTION OF THE INVENTION Hereinafter, the method for removing bitterness of a glycyrrhizin-containing liquid according to the present invention will be specifically described.
グリチルリチン含有液 本発明で原料として用いられるグリチルリチン含有液
は、グリチルリチンを含有する液であればよく、たとえ
ば甘草エキスなどが用いられる。Glycyrrhizin-Containing Liquid The glycyrrhizin-containing liquid used as a raw material in the present invention may be any liquid containing glycyrrhizin, such as licorice extract.
上記のようなグリチルリチン含有液において、グリチ
ルリチンは、通常グリチルリチン酸またはその塩として
含有されている。In the glycyrrhizin-containing liquid as described above, glycyrrhizin is usually contained as glycyrrhizic acid or a salt thereof.
また上記のようなグリチルリチン含有液は、グリチル
リチンとともにα−グルコシル化可能な苦味物質を含有
している。この苦味物質は、配糖体であろうと推定され
るが、その構造は現状では特定されていない。The glycyrrhizin-containing liquid as described above contains a bitter substance capable of α-glucosylation together with glycyrrhizin. This bitter tastant is presumed to be a glycoside, but its structure has not been identified at present.
この苦味物質は、後述するように、澱粉質の存在下で
α−グルコシル転移酵素と接触すると、グリチルリチン
よりもはるかに容易にα−グルコシル化される。This bitter tastant is much more easily α-glucosylated than glycyrrhizin when contacted with α-glucosyltransferase in the presence of starch, as described below.
澱 粉 質 本発明で用いられる澱粉質としては、α−グルコシル
転移酵素の基質となるものであればよく、具体的には、
たとえばアミロース、アミロペクチン、澱粉等だけでな
く、澱粉加水分解物、たとえばシクロデキストリン、DE
1〜50程度の澱粉液化物、澱粉糖化物が用いられる。Starch The starch used in the present invention may be any substance as long as it serves as a substrate for α-glucosyltransferase.
For example, amylose, amylopectin, starch, etc., as well as starch hydrolysates such as cyclodextrin, DE
About 1 to 50 liquefied starch and saccharified starch are used.
本発明においては、このような澱粉質は、グリチルリ
チン含有液中に含まれるグリチルリチン１重量部に対し
て、通常、0.05〜5.0重量部、好ましくは0.1〜1.5重量
部、更に好ましくは0.1〜0.45重量部の量で用いられる
ことが望ましい。In the present invention, such starch is usually 0.05 to 5.0 parts by weight, preferably 0.1 to 1.5 parts by weight, more preferably 0.1 to 0.45 parts by weight, based on 1 part by weight of glycyrrhizin contained in the glycyrrhizin-containing solution. Desirably, it is used in parts amounts.
α−グルコシル転移酵素 本発明で用いられるα−グルコシル転移酵素として
は、グリチルリチン含有液の苦味物質を澱粉質の存在下
にα−グルコシル化し得る酵素であれば、どのような酵
素でも用いることができるが、具体的には、バチルス
マセランス、バチルス メガテリウム バチルス サー
キュランス、バチルス ポリミキサ、バチルス スティ
ア サーモフィラスなどのバチルス属、クレプトシーラ
ニューモニエなどのクレプトシーラ属などの細菌によ
って生産されるシクロデキストリン グルカノトランス
フェラーゼなどを用いることができる。α-Glucosyltransferase As the α-glucosyltransferase used in the present invention, any enzyme capable of α-glucosylating a bitter substance in a glycyrrhizin-containing solution in the presence of starch can be used. But specifically, Bacillus
Cyclodextrin glucanotransferase produced by a bacterium such as Macerans, Bacillus megaterium, Bacillus circulans, Bacillus polymixer, Bacillus genus such as Bacillus stear thermophilus, or a bacterium such as Creptoseala genus such as Creptosea pneumoniae can be used.
このようなα−グルコシル転移酵素としては、必ずし
も精製して使用する必要はなく、通常は粗精製の酵素で
も充分である。Such an α-glucosyltransferase does not necessarily need to be purified and used, and a crude enzyme is usually sufficient.
α−グルコシル転移酵素は、グリチルリチン含有液と
混合される澱粉質100g当り、通常、100〜50,000単位、
好ましくは、1000〜2000単位の量で、グリチルリチン含
有物と澱粉質との混合物中に添加されることが望まし
い。α-glucosyltransferase is usually 100 to 50,000 units per 100 g of starch mixed with a glycyrrhizin-containing solution,
Preferably, it is added to the mixture of the glycyrrhizin-containing substance and the starch in an amount of 1000 to 2000 units.
なお本発明においては、グリチルリチン含有液と澱粉
質とα−グルコシル転移酵素との混合順序は特に限定さ
れず、たとえば上記成分を同時に混合してもよいし、グ
リチルリチン含有液と澱粉質とを混合した後にα−グル
コシル転移酵素を添加し混合してもよい。In the present invention, the mixing order of the glycyrrhizin-containing solution, the starch and the α-glucosyltransferase is not particularly limited. For example, the above components may be mixed simultaneously, or the glycyrrhizin-containing solution and the starch may be mixed. Later, α-glucosyltransferase may be added and mixed.
上記のようなグリチルリチン含有液と澱粉質との混合
物に、α−グルコシル転移酵素を作用させるに際して
は、系のpHは３〜10、好ましくは5.0〜6.0であり、系の
温度は20〜90℃、好ましくは50〜70℃であり、反応時間
は温度あるいは酵素の濃度などによって大きく変化する
が、通常１〜120分、好ましくは５〜60分であることが
望ましい。When α-glucosyltransferase is allowed to act on a mixture of the glycyrrhizin-containing solution and the starch as described above, the pH of the system is 3 to 10, preferably 5.0 to 6.0, and the temperature of the system is 20 to 90 ° C. The reaction time varies greatly depending on the temperature, the concentration of the enzyme, and the like, but is usually 1 to 120 minutes, preferably 5 to 60 minutes.
このようにして苦味物質を含むグリチルリチン含有液
と澱粉質との混合物にα−グルコシル転移酵素を作用さ
せると、該苦味物質はほとんどα−グルコシル化され、
一方グリチルリチンのα−グルコシル化率を５％以下、
好ましくは３％以下、特に好ましくは０％に抑えること
ができる。これは、上述のように苦味物質はグリチルリ
チンよりもはるかに容易にα−グルコシル化されるため
であると考えられる。したがって、本発明によって処理
されたグリチルリチン含有液は、苦味がほぼ除去される
にもかかわらず甘味はほとんど低下しない。なお、苦味
物質の除去率は50％以上、好ましくは80％以上であるこ
とが望ましい。When α-glucosyltransferase is allowed to act on a mixture of a glycyrrhizin-containing liquid containing a bitter substance and starch, the bitter substance is almost α-glucosylated,
On the other hand, the α-glucosylation rate of glycyrrhizin is 5% or less,
Preferably it can be suppressed to 3% or less, particularly preferably to 0%. This is thought to be because bitter substances are much more easily α-glucosylated than glycyrrhizin, as described above. Therefore, the glycyrrhizin-containing liquid treated according to the present invention hardly loses sweetness even though bitterness is almost removed. The removal rate of the bitter substance is desirably 50% or more, preferably 80% or more.
上記のような現象は、苦味物質はＤ−グルコースなど
を残基とする配糖体であり、容易にα−グルコシル化さ
れるのに対し、グリチルリチンはＤ−グルクロン酸を残
基とする配糖体であり、極めてα−グルコシル化されに
くいために起ると考えられる。The phenomenon described above indicates that the bitter substance is a glycoside having D-glucose or the like as a residue and is easily α-glucosylated, whereas glycyrrhizin is a glycoside having D-glucuronic acid as a residue. It is considered to be caused by the fact that it is very hard to be α-glucosylated.
このようにして処理されて、苦味が除去され、甘味が
保持されたグリチルリチン含有液は、そのまま飲食に供
することもできるが、通常、該グリチルリチン含有液を
加熱して酵素を失活させた後に飲食に供する。また場合
によっては、該グリチルリチン含有液を濃縮したり、乾
燥して粉末化したりして飲食に供することもできる。さ
らに場合によっては、該グリチルリチン含有液を、脱色
剤、イオン交換樹脂、吸着樹脂等を用いて精製して飲食
に供することもできる。The glycyrrhizin-containing liquid that has been treated in this way to remove bitterness and retain its sweetness can be directly used for eating and drinking.However, usually, the glycyrrhizin-containing liquid is heated to inactivate the enzyme and then eat and drink. To serve. In some cases, the glycyrrhizin-containing liquid can be concentrated or dried to be powdered before being provided for eating and drinking. Further, in some cases, the glycyrrhizin-containing liquid can be purified using a decolorizing agent, an ion-exchange resin, an adsorption resin, or the like, and provided for eating and drinking.
また、上記のようにして処理されたグリチルリチン含
有液からグリチルリチンを精製して、飲食に供すること
もできる。In addition, glycyrrhizin can be purified from the glycyrrhizin-containing liquid treated as described above and provided for eating and drinking.
発明の効果 本発明によれば、苦味物質を含むグリチルリチン含有
液から、甘味を低下させることなく苦味だけを効率よく
除去することができる。Effects of the Invention According to the present invention, only a bitter taste can be efficiently removed from a glycyrrhizin-containing liquid containing a bitter substance without reducing sweetness.
［実施例］ 次に、本発明を実施例により、さらに具体的に説明す
るが、本発明はこれらの実施例に限定されるものではな
い。[Examples] Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
なお、以下の記載において、「％」はとくに断りのな
い限り「重量％」を意味する （実施例１） 甘草抽出物製剤（丸善化成（株）製、商品名；リコス
ター（甘草抽出物）100重量部にクエン酸三ナトリウム6
0重量部を配合したもの）100gとデキストリン（松谷化
学工業（株）製、商品名；パインデックス＃100、DE2〜
５）20gとを、固形分濃度が40％になるように水に溶解
し、この溶液のpH値を5.3、温度を55℃に調整した（原
体溶液）。この溶液にバチルス・サーキュランス由来の
α−グルコシル化酵素、シクロデキストリングルカノト
ランスフェラーゼ300単位を加え、５分間α−グルコシ
ル化反応させた後、直ちに沸騰水中で15分間加熱し、酵
素を失活させた（CGT−アーゼ反応液）。この液を濾過
して得られた濾液を減圧下に濃縮した後、乾燥して、α
化反応物118gを得た（以下これを本発明品という）。In the following description, “%” means “% by weight” unless otherwise specified. (Example 1) Licorice extract preparation (manufactured by Maruzen Kasei Co., Ltd., trade name; Licostar (licorice extract) 100 Trisodium citrate 6 parts by weight
100 g of dextrin (product containing 0 parts by weight) and dextrin (trade name, manufactured by Matsutani Chemical Industry Co., Ltd .; Paindex # 100, DE2 ~)
5) 20 g was dissolved in water so that the solid content concentration became 40%, and the pH value of this solution was adjusted to 5.3, and the temperature was adjusted to 55 ° C (stock solution). To this solution was added 300 units of α-glucosylation enzyme derived from Bacillus circulans, cyclodextrin glucanotransferase, and the mixture was subjected to α-glucosylation reaction for 5 minutes, and immediately heated in boiling water for 15 minutes to inactivate the enzyme. (CGT-ase reaction solution). The filtrate obtained by filtering this solution was concentrated under reduced pressure, and then dried to obtain α.
As a result, 118 g of a reaction product was obtained (hereinafter referred to as the product of the present invention).
この本発明品のグリチルリチン含有率を高速液体クロ
マトグラフィーを用いて次のような条件で測定したとこ
ろ、本発明品中におけるグリチルリチン含有率は18.8％
であった。When the glycyrrhizin content of the product of the present invention was measured under the following conditions using high performance liquid chromatography, the glycyrrhizin content in the product of the present invention was 18.8%.
Met.
（高速液体クロマトグラフィーの測定条件） カラム ：μ−Bondapark C−18 キャリヤー液 :2％酢酸水溶液；アセトニトリル＝2
0:11（容量） 検出波長 :254nm 温度 :42℃ 感度 ：×0.32 チャートスピード:5mm/分 次に下記のような対照品（Ｉ）、（II）を調製し、上
記の本発明品中に含まれるグリチルリチンのα−グルコ
シル化率等を調べた。(Measurement conditions of high performance liquid chromatography) Column: μ-Bondapark C-18 Carrier solution: 2% acetic acid aqueous solution; acetonitrile = 2
0:11 (capacity) Detection wavelength: 254 nm Temperature: 42 ° C. Sensitivity: × 0.32 Chart speed: 5 mm / min Next, the following control products (I) and (II) were prepared and contained in the above-mentioned product of the present invention. The α-glucosylation rate and the like of glycyrrhizin contained therein were examined.
対照品（Ｉ）の調製 上記本発明品の調製の際の操作と同様に、甘草抽出物
製剤100gとデキストリン20gとを固形分濃度が40％にな
るように水に溶解し、この溶液のpH値を5.3、温度を55
℃に調整した。Preparation of Control Product (I) In the same manner as in the preparation of the product of the present invention described above, 100 g of a licorice extract preparation and 20 g of dextrin were dissolved in water so that the solid content concentration became 40%, and the pH of this solution was adjusted. Value 5.3, temperature 55
Adjusted to ° C.
この溶液にα−グルコシル化酵素を加えることなく、
次いで、この溶液を濾過、濃縮、乾燥して、対照品
（Ｉ）118gを得た。Without adding α-glucosylating enzyme to this solution,
Next, this solution was filtered, concentrated and dried to obtain 118 g of a control product (I).
得られた対照品（Ｉ）のグリチルリチン含有率を、本
発明品と同じ条件で高速液体クロマトグラフィーを用い
て測定したところ、この対照品（Ｉ）中におけるグリチ
ルリチン含有率は19.2％であった。The glycyrrhizin content of the obtained control product (I) was measured using high performance liquid chromatography under the same conditions as those of the product of the present invention. The glycyrrhizin content in this control product (I) was 19.2%.
対照品（II）の調製 上記本発明品の調製の際の操作と同様に、甘草抽出物
製剤100gとデキストリン20gとを固形分濃度が40％にな
るように水に溶解し、この溶液のpH値を5.3、温度を55
℃に調整した。Preparation of Control Product (II) In the same manner as in the preparation of the product of the present invention described above, 100 g of the licorice extract preparation and 20 g of dextrin were dissolved in water so that the solid content concentration became 40%, and the pH of this solution was adjusted. Value 5.3, temperature 55
Adjusted to ° C.
このようにして得られた溶液を直ちに沸騰水中に保持
して加熱し、この時点で酵素（シクロデキストリングル
カノトランスフェラーゼ）を加えた以外は上記本発明品
の調製と同様に操作して、対照品（II）118gを得た。The solution thus obtained was immediately held in boiling water and heated. At this point, the same procedure as in the preparation of the product of the present invention was performed except that an enzyme (cyclodextrin glucanotransferase) was added. (II) 118 g were obtained.
得られた対照品（II）のグリチルリチン含有率を、本
発明品の分析の際に採用した条件と同様の条件で高速ク
ロマトグラフィーにて測定したところ、対照品（II）中
におけるグリチルリチン含有率は19.2％であった。When the glycyrrhizin content of the obtained control product (II) was measured by high-performance chromatography under the same conditions as those used in the analysis of the product of the present invention, the glycyrrhizin content in the control product (II) was 19.2%.
α−グルコシル化率 上記のように対照品（Ｉ）、（II）におけるグリチル
リチンの含有率は共に19.2％であった。また、本発明品
のグリチルリチンの含有率は18.8％であった。α-Glucosylation rate As described above, the content of glycyrrhizin in each of the control products (I) and (II) was 19.2%. The glycyrrhizin content of the product of the present invention was 18.8%.
従って、対照品（Ｉ）あるいは（II）のグリチルリチ
ン含量をベース（100％）とすると、本発明品における
グリチルリチンの含有率は98％に相当する。すなわち、
本発明品を製造する際のα−グルコシル化反応によって
は僅かに２％のグリチルリチンがα−グルコシル化され
たに過ぎない。従って、本発明品の甘味の減少程度は非
常に僅かであるが、このα−グルコシル化にともなって
苦味および渋味は除去された。Therefore, based on the glycyrrhizin content of the control product (I) or (II) as a base (100%), the content of glycyrrhizin in the product of the present invention is equivalent to 98%. That is,
Only 2% of glycyrrhizin was α-glucosylated by the α-glucosylation reaction in producing the product of the present invention. Therefore, although the degree of sweetness reduction of the product of the present invention was very slight, bitterness and astringency were removed with this α-glucosylation.
以下、本発明品の甘味並びに苦味および渋味について
の試験結果を示す。Hereinafter, test results on the sweetness, bitterness and astringency of the product of the present invention will be shown.
苦味除去率の測定 本発明品、対照品（Ｉ）、（II）の三点について、官
能検査によって苦味除去率を求めた。即ち、本発明品を
濃度１％の水溶液として、これと同等の苦味、渋味とな
る対照品（Ｉ）、（II）の濃度を求め、苦味除去率とし
た。なお、パネルは利味（ききあじ）経験者10名にて、
室温で行なった。Measurement of Bitter Removal Rate The bitterness removal rate was determined by a sensory test for three points of the product of the present invention, the control product (I), and (II). That is, the product of the present invention was used as an aqueous solution having a concentration of 1%, and the concentrations of the control products (I) and (II) having the same bitterness and astringency as the aqueous solution were determined, and the results were defined as the bitterness removal rate. In addition, the panel is 10 people who have experience
Performed at room temperature.
結果を表１に示す。 Table 1 shows the results.
上記結果の通り、本発明品は対照品（Ｉ）、（II）に
くらべ約80％程度苦味が除去され、呈味がすぐれてい
た。なお、確認のため甘味テストも行ったが、本発明品
は対照品（Ｉ）、（II）にくらべ甘味度に変化はなかっ
た。 As shown in the above results, the product of the present invention had about 80% less bitterness than the control products (I) and (II), and had excellent taste. Although a sweetness test was also performed for confirmation, the product of the present invention did not change in the degree of sweetness as compared with the control products (I) and (II).
呈味比較試験（砂糖液） 濃度８％の砂糖液に本発明品、対照品（Ｉ）、（II）
をそれぞれ総重量に対して0.1％となるような量で添加
し、これらを濃度12％の砂糖液を対照として利味による
呈味の比較を行った。なお、パネルは利味経験者10名で
室温にて行った。Taste comparison test (sugar solution) A sugar solution having a concentration of 8% was added to a product of the present invention, a control product (I), and (II).
Were added in such an amount as to be 0.1% with respect to the total weight, and the taste was compared by taste using a sugar solution having a concentration of 12% as a control. In addition, the panel was performed at room temperature by 10 experienced people.
結果を表２に示す。 Table 2 shows the results.
本発明品を配合した砂糖水には、苦味、渋味がなく、
スッキリとした甘味となり、後引き（あとびき）も少な
く、砂糖液中にグリチルリチンの甘味がよく調和した味
であった。従って、本発明品は、従来の苦味物質を含む
グリチルリチンに比べて多量に使用したとしても、苦味
および渋味がなく、砂糖とグリチルリチンとの混合物中
におけるグリチルリチンの配合量を高めることが可能と
なる。 Sugar water containing the product of the present invention has no bitterness or astringency,
The sweetness was refreshing, and there was little after-drawing (afterglow), and the sweetness of glycyrrhizin in the sugar solution was well balanced. Therefore, the product of the present invention has no bitterness and astringency, and can increase the amount of glycyrrhizin in a mixture of sugar and glycyrrhizin, even when used in a larger amount than glycyrrhizin containing a conventional bitter substance. .
これに対して、対照品（Ｉ）、（II）は、苦味、渋味
が強く、両者の間に苦味および渋味に差はなかった。ま
た、これらの味が後引きし、砂糖の前甘味と分離して、
呈味としてバランスが極めてわるかった。In contrast, the control products (I) and (II) had strong bitterness and astringency, and there was no difference in bitterness and astringency between the two. In addition, these tastes are delayed, separated from the pre-sweetness of sugar,
The taste was very unbalanced.
呈味比較試験（調味液） 市販醤油（キッコーマン本醸造）に本発明品、対照品
（Ｉ）、（II）をそれぞれ総重量に対して0.2％となる
ような量で添加した。これを水で２倍に希釈して、呈味
を比較した。なおパネルは利味経験者10名で室温にて行
った。Taste Comparison Test (Seasoning Solution) The commercially available soy sauce (Kikkoman Honzo Brewery) was added with the product of the present invention, the control products (I) and (II) in an amount of 0.2% based on the total weight. This was diluted twice with water, and the taste was compared. The panel was performed at room temperature with 10 experienced experts.
結果を表３に示す。 Table 3 shows the results.
本発明品を配合した醤油は、苦味、渋味もなくスッキ
リとした甘味となり全体の呈味の調和も良かった。 The soy sauce blended with the product of the present invention was refreshingly sweet without bitterness and astringency, and had good overall harmony in taste.
これに対して対照品（Ｉ）、（II）は後引きが強く、
苦み、渋味を感じた。On the other hand, the control products (I) and (II) have a strong retraction,
I felt bitterness and astringency.
このように本発明品は、苦味および渋味がなく、しか
も甘味の減衰もなかった。さらに、このようなα−グル
コシル化に伴って、例えば酸性領域における安定性等の
特性にも変化は見られなかった。Thus, the product of the present invention did not have bitterness and astringency, and did not attenuate sweetness. Further, with such α-glucosylation, there was no change in properties such as stability in an acidic region.
酸性領域における安定性試験 （試験方法） （１）Mcllvaine氏緩衝液（pH2.5、3.0、3.5、4.0）を
調整した。Stability test in acidic region (Test method) (1) Mcllvaine buffer (pH 2.5, 3.0, 3.5, 4.0) was prepared.
（２）上記各pH調整液に本発明品、対照品（Ｉ）、（I
I）をそれぞれ濃度0.1％となるような量で添加し、試験
液とした。(2) Each of the above pH-adjusted solutions was added to the product of the present invention, control product (I),
I) was added in such an amount as to give a concentration of 0.1%, to give test solutions.
（３）上記各試験液をそのまま室温に放置（24時間）し
たもの、および上記各試験液を一旦80℃にて15分間加熱
後、濾過し、得られた濾液を冷凍後、解凍したものにつ
いて安定性（混濁、沈澱等の有無）をテストした。(3) Each of the above test liquids was left at room temperature (24 hours), and each of the above test liquids was heated at 80 ° C. for 15 minutes, filtered, and the obtained filtrate was frozen and thawed. Stability (presence or absence of turbidity, sedimentation, etc.) was tested.
これは通常用いる加速テストの方法である。 This is a commonly used acceleration test method.
（結果） 結果を表４および表５に示す。(Results) The results are shown in Tables 4 and 5.
上記の通り、本発明品は対照品にくらべ酸性域での安
定性には何ら差は認められなかった。 As described above, the product of the present invention did not show any difference in stability in the acidic region as compared with the control product.
比較例１ 実施例１において、酵素を加えた後24時間反応させた
以外は実施例１と同様にして、反応品118gを得た。Comparative Example 1 A reaction product of 118 g was obtained in the same manner as in Example 1 except that the reaction was carried out for 24 hours after adding the enzyme.
この反応品のグリチルリチンの含有率を、実施例１記
載の本発明品と同じ条件で高速液体クロマトグラフィー
を用いて測定したところ、この反応品のグリチルリチン
含有率は10.0％であった。The glycyrrhizin content of this reaction product was measured using high performance liquid chromatography under the same conditions as the product of the present invention described in Example 1, and the glycyrrhizin content of this reaction product was 10.0%.
この反応品を対照品（III）とし、本発明品、対照品
（Ｉ）および対照品（II）と以下のような比較を行なっ
た。This reaction product was used as a control product (III), and the following comparisons were made with the product of the present invention, the control product (I) and the control product (II).
α−グルコシル化率 実施例１における場合と同様に、対照品（II）のグリ
チルリチン含有をベース（100％）とすると、対照品（I
II）中におけるグリチルリチンの含有率は52％に相当し
ており、対照品（III）では、グリチルリチンのα−グ
ルコシル化率（グリチルリチンの減少率）は48％であっ
た。α-Glucosylation rate As in Example 1, when the glycyrrhizin content of the control product (II) was used as the base (100%), the control product (I
The content of glycyrrhizin in II) was equivalent to 52%, and in the control product (III), the α-glucosylation rate of glycyrrhizin (decrease rate of glycyrrhizin) was 48%.
本発明品および対照品（Ｉ）〜（III）のグリチルリ
チン含量およびグリチルリチンのα−グルコシル化率を
併せて表６に示す。Table 6 also shows the glycyrrhizin content and the α-glucosylation rate of glycyrrhizin of the product of the present invention and the control products (I) to (III).
甘味度の測定 対照品（Ｉ）の0.20％水溶液を調製し、これと同等の
甘味を有する本発明品、対照品（II）、（III）の濃度
を求めた。なお、パネルは利味経験者10名で行い、室温
でテストした。 Measurement of Degree of Sweetness A 0.20% aqueous solution of the control product (I) was prepared, and the concentrations of the present invention product, the control products (II), and (III) having the same sweetness were determined. In addition, the panel was performed by 10 experienced persons and tested at room temperature.
結果を表７に示す。 Table 7 shows the results.
対照品（III）では対照品（Ｉ）にくらべ甘味が半減
していた。これは前記グリチルリチン含量の分析値と対
応しており、グリチルリチン含量が減少し、α−グルコ
シル化率が上昇すればするだけ甘味が失われる。従っ
て、砂糖に代えて、本発明品よりも甘味に乏しい対照品
（III）を用いようとすると、実用上コスト的に不利と
なることを示している。 The sweetness of the control product (III) was reduced to half that of the control product (I). This corresponds to the analysis value of the glycyrrhizin content, and the sweetness is lost as much as the glycyrrhizin content decreases and the α-glucosylation rate increases. Therefore, if the control product (III), which is less sweet than the product of the present invention, is used instead of sugar, it is practically disadvantageous in terms of cost.
また苦味質については、本発明品と対照品（III）と
の間に大差はなかった。As for the bitter taste, there was no significant difference between the product of the present invention and the control product (III).
苦味物質の苦味復元試験 実施例１の本発明品と全く同様の方法で、調製した本
発明品50gを水150mlに溶解し、pH値はそのまま（5.3）
で、温度45℃に調整した後、グルコアミラーゼ（加水分
解酵素、長瀬産業（株）製50000単位を加え２時間反応
させた。Bitter taste recovery test of bitter substance 50 g of the prepared product of the present invention was dissolved in 150 ml of water in exactly the same manner as the product of the present invention of Example 1, and the pH value was maintained as it was (5.3)
After adjusting the temperature to 45 ° C., glucoamylase (hydrolytic enzyme, manufactured by Nagase & Co., Ltd., 50,000 units) was added and reacted for 2 hours.
このように反応させて得られた溶液を直ちに沸騰水中
で加熱し、酵素を失活させた（グルコアミラーゼ処理
液）。次いでこの液を真空濃縮した後、乾燥して粉末に
した（加水分解物（Ｉ）とする）。The solution obtained by such a reaction was immediately heated in boiling water to inactivate the enzyme (glucoamylase-treated solution). Next, this liquid was concentrated in vacuo and dried to obtain a powder (referred to as hydrolyzate (I)).
本発明品と加水分解物（Ｉ）、対照品（Ｉ）、（II）
の４点について、前記と同様にして苦味除去率を測定し
た。Product of the present invention and hydrolyzate (I), control product (I), (II)
For the four points, the bitterness removal rate was measured in the same manner as described above.
結果を表８に示す。 Table 8 shows the results.
上記結果の通り、本発明品に加水分解酵素グルコアミ
ラーゼを作用させると対照品（Ｉ）、（II）の苦味と同
じ強さに苦味が復元した。これは、一旦苦味物質のα−
グルコシル化反応によって、グルコースが転移したα−
化苦味物質に、加水分解酵素を作用させることにより、
グルコースが切断され、再び元の苦味物質に戻り苦味が
復元したものと考えられる。 As described above, when the hydrolase glucoamylase was allowed to act on the product of the present invention, the bitterness was restored to the same intensity as that of the control products (I) and (II). This is because the bitter substance α-
Α- to which glucose is transferred by the glucosylation reaction
By acting on hydrolyzing enzymes,
It is considered that glucose was cut and returned to the original bitter substance to restore bitter taste.
このことは、下記のような高速液体クロマトグラフィ
ーによる吸光度測定の結果とも対応している。This also corresponds to the results of absorbance measurement by high performance liquid chromatography as described below.
高速液体クロマトグラフィーによる吸光度測定 本発明品の調製過程で得られた前記「原体溶液」、
「CGT−アーゼ反応液」、および本発明品をグルコアミ
ラーゼで処理して得られた前記「グルコアミラーゼ処理
液」について、実施例１に示した条件と同様な条件で、
高速液体クロマトグラフィーを用いて、グリチルリチン
および苦味物質の吸光度の測定を行ない、原体溶液とCG
T−アーゼ反応液とを比較すると、一つの苦味物質に起
因すると考えられるピークは、原体溶液においては相当
吸光度が高いのに対して、α−グルコシル化することに
よって得られるCGT−アーゼ反応液においてはこのピー
クは相当低くなっており、従って、α−グルコシル化に
よって苦味物質がα−化されたことがわかる。Absorbance measurement by high-performance liquid chromatography The above "constituent solution" obtained in the preparation process of the product of the present invention,
For the “CGT-ase reaction solution” and the “glucoamylase-treated solution” obtained by treating the product of the present invention with glucoamylase, under the same conditions as those described in Example 1,
Using high performance liquid chromatography, the absorbance of glycyrrhizin and bitter substances was measured, and the drug substance solution and CG
When compared with the T-ase reaction solution, the peak considered to be due to one bitter substance has a considerably high absorbance in the drug substance solution, but the CGT-ase reaction solution obtained by α-glucosylation. In Fig. 7, this peak is considerably low, and it can be seen that the bitter substance has been converted to α-glucosylation by α-glucosylation.
次にCGT−アーゼ反応液とグルコアミラーゼ処理液に
ついて高速液体クロマトグラフィーによる吸光度を比較
すると、α−グルコシル化によって減少した上記の苦味
物質に起因するピークは、加水分解によって再び出現
し、この苦味物質の相対的な吸光度は原体溶液における
相対的強度とほぼ同等の値となる。すなわち、α−グル
コシル化によってα−化された苦味物質はグルコアミラ
ーゼを用いた加水分解反応によって加水分解され、再び
苦味物質となることがわかる。Next, comparing the absorbance of the CGT-ase reaction solution and the glucoamylase-treated solution by high-performance liquid chromatography, the peak due to the bitter substance reduced by α-glucosylation appears again by hydrolysis, and this bitter substance Has a value substantially equivalent to the relative intensity in the drug substance solution. That is, it is understood that the bitter substance α-converted by α-glucosylation is hydrolyzed by a hydrolysis reaction using glucoamylase, and becomes a bitter substance again.
なお、本発明において、α−化反応によるグリチルリ
チンのα−化率は低いために、原体溶液、CGT−アーゼ
反応液およびグルコアミラーゼ処理液のいずれにおいて
もグリチルリチンに起因するピークにはほとんど変化が
見られず、グリチルリチンは実質的にα−化されていな
いことがわかる。In the present invention, since the α-formation rate of glycyrrhizin due to the α-formation reaction is low, there is almost no change in the peak due to glycyrrhizin in any of the drug substance solution, the CGT-ase reaction solution and the glucoamylase-treated solution. It can be seen that glycyrrhizin is not substantially α-formated.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 高屋 幾夫 千葉県市原市岩崎西１―６―41 東洋精 糖株式会社千葉工場内 (58)調査した分野(Int.Cl.6，ＤＢ名) A23L 1/22 - 1/237 A23L 1/24 ＪＩＣＳＴファイル（ＪＯＩＳ)──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Ikuo Takaya 1-6-41 Iwasaki Nishi, Ichihara-shi, Chiba Pref. Toyo Sugar Co., Ltd. Chiba Plant (58) Field surveyed (Int.Cl. 6 , DB name) A23L 1/22-1/237 A23L 1/24 JICST file (JOIS)
Claims (1)
能な甘草エキス由来の苦味物質を含むグリチルリチン含
有液と、澱粉質との混合物に、α−グルコシル転移酵素
を作用させ、グリチルリチン含有液中に含まれる苦味物
質をα−グルコシル化するとともにグリチルリチンのα
−グルコシル化率を５％以下に抑えることを特徴とする
グリチルリチン含有液の苦味除去方法。1. A mixture of a glycyrrhizin-containing liquorice extract-derived bitter substance derived from glycyrrhizin and an α-glucosylatable licorice extract and a starch, which is treated with α-glucosyltransferase to give a bitterness contained in the glycyrrhizin-containing liquid. The substance is α-glucosylated and the α of glycyrrhizin
-A method for removing bitterness of a glycyrrhizin-containing solution, wherein the glucosylation rate is suppressed to 5% or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1029297A JP2820945B2 (en) | 1989-02-08 | 1989-02-08 | Method for removing bitterness of glycyrrhizin-containing liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1029297A JP2820945B2 (en) | 1989-02-08 | 1989-02-08 | Method for removing bitterness of glycyrrhizin-containing liquid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02207768A JPH02207768A (en) | 1990-08-17 |
| JP2820945B2 true JP2820945B2 (en) | 1998-11-05 |
Family
ID=12272307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1029297A Expired - Fee Related JP2820945B2 (en) | 1989-02-08 | 1989-02-08 | Method for removing bitterness of glycyrrhizin-containing liquid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2820945B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4786041B2 (en) * | 2001-03-02 | 2011-10-05 | 丸善製薬株式会社 | Method for reducing astringency and astringency and lotus germ extract preparation for reducing astringency and astringency |
| CN103783476B (en) * | 2013-12-10 | 2016-08-17 | 上海百润投资控股集团股份有限公司 | A kind of bitterness covers up essence |
-
1989
- 1989-02-08 JP JP1029297A patent/JP2820945B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02207768A (en) | 1990-08-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1295533B1 (en) | Sweetener and process for producing the same | |
| JP2949019B2 (en) | Salty taste enhancing composition and enhancing method | |
| JPH05981B2 (en) | ||
| JPH06209784A (en) | Method of cleaving starch nonrandomly and low d.e. inverted product produced by said method | |
| JPH03503238A (en) | Enzymatic synthesis method of oligodextran useful for producing sugar substitutes and novel oligodextran | |
| US5332803A (en) | Processes for the preparation of amylase inhibitor | |
| GB2110235A (en) | Alcohol-containing powers | |
| Sejr Olsen et al. | The estimation of vicine and convicine in fababeans (Vicia faba L.) and isolated fababean proteins | |
| JP2820945B2 (en) | Method for removing bitterness of glycyrrhizin-containing liquid | |
| JPH07107972A (en) | Production of soluble flavonoid | |
| JPS6258983A (en) | Production of beer of high fermentation degree | |
| JP3515078B2 (en) | Taste improvement of food and drink by coffee oligosaccharide | |
| JPH07184597A (en) | Method for removing bitter taste, puckery taste and astringent taste from leaf extract of gymnema inodorum | |
| JP6906346B2 (en) | Aroma component retention agent and aroma component retention method for food and drink | |
| JPH0441997B2 (en) | ||
| JPH0683674B2 (en) | Cellobiose manufacturing method | |
| JPS6037950A (en) | How to improve the taste of stevia sweetener | |
| JPH11146778A (en) | Fermented malt beverage and its production | |
| JPH012552A (en) | Method for reducing bitterness of Gymnema sylvestre extract | |
| JP3101640B2 (en) | Pectin degrading enzyme | |
| JPH07327602A (en) | Method for removing bitter taste/astringency of hydrangea leaf extract | |
| JPH0688908B2 (en) | How to remove the bitterness and astringency of Gymnema sylvestre leaf extract | |
| JPH02131592A (en) | Sweetener manufacturing method | |
| JPH05982B2 (en) | ||
| JP2989217B2 (en) | Exo-.BETA.-1,4-galactanase and its use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |