JPH012552A - Method for reducing bitterness of Gymnema sylvestre extract - Google Patents
Method for reducing bitterness of Gymnema sylvestre extractInfo
- Publication number
- JPH012552A JPH012552A JP62-155303A JP15530387A JPH012552A JP H012552 A JPH012552 A JP H012552A JP 15530387 A JP15530387 A JP 15530387A JP H012552 A JPH012552 A JP H012552A
- Authority
- JP
- Japan
- Prior art keywords
- bitterness
- starch
- extract
- crude
- gymnema sylvestre
- 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
- 235000019658 bitter taste Nutrition 0.000 title claims description 35
- 239000000284 extract Substances 0.000 title claims description 28
- 230000001603 reducing effect Effects 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 241000208253 Gymnema sylvestre Species 0.000 title claims description 6
- 229920002472 Starch Polymers 0.000 claims description 28
- 235000019698 starch Nutrition 0.000 claims description 28
- 239000008107 starch Substances 0.000 claims description 28
- 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 claims description 11
- 239000008103 glucose Substances 0.000 claims description 11
- 238000012546 transfer Methods 0.000 claims description 11
- 229920000858 Cyclodextrin Polymers 0.000 claims description 6
- 229930183009 gymnemic acid Natural products 0.000 claims description 5
- 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 description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 102000000340 Glucosyltransferases Human genes 0.000 claims description 2
- 108010055629 Glucosyltransferases Proteins 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229930182470 glycoside Natural products 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000008351 acetate buffer Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003648 triterpenes Chemical class 0.000 description 3
- VKJLHZZPVLQJKG-ABHKXHSUSA-N (3r,4r,4ar,5s,6ar,6as,6br,8ar,9r,10s,12ar,14bs)-4a,9-bis(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,4,5,10-tetrol Chemical group C([C@@]12C)C[C@H](O)[C@@](C)(CO)[C@@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3CC(C)(C)[C@@H](O)[C@H](O)[C@]3(CO)[C@@H](O)C[C@]21C VKJLHZZPVLQJKG-ABHKXHSUSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 2
- 102100022624 Glucoamylase Human genes 0.000 description 2
- 241000208251 Gymnema Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 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 2
- 238000011161 development Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 241000208327 Apocynaceae Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102100037487 Histone H1.0 Human genes 0.000 description 1
- 101001026554 Homo sapiens Histone H1.0 Proteins 0.000 description 1
- DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 description 1
- 241000178960 Paenibacillus macerans Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VKJLHZZPVLQJKG-UHFFFAOYSA-N Theasapogenol A Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)C(O)C(O)C3(CO)C(O)CC21C VKJLHZZPVLQJKG-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 230000000675 anti-caries Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000004075 cariostatic agent Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000003563 glycoside group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
イ１発明の目的
産業上の利用分野
本発明は、薬用及び低カロリー飲食物として有用なギム
ネマ・シルベスタ抽出物の苦味を低減する方法に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION (1) Object of the Invention Industrial Application Field The present invention relates to a method for reducing the bitterness of a Gymnema sylvestre extract useful as a medicinal and low-calorie food or drink.
従来の技術
ギムネマｓシルベスタ（Ｇｙｍｎｅｍａ、 ５ｙｌｖｅ
ｓｔｒｅ Ｒ。Conventional technology Gymnema, 5ylve
stre R.
Ｂｒ、−以下ＧＳと云う）はインド、中国、東南アジア
、アフリカ等の熱帯、亜熱帯に自生するカガイモ科に属
する植物で、ＧＳの水又はアルコール抽出物は甘味抑制
効果がある一方、腸管における糖の吸収抑制効果もある
ことが判り、薬用及び低カロリー飲食物への利用が可能
である。又抗頒蝕効果があることも判り、虫歯予防剤と
しての利用も可能である。Br, -hereinafter referred to as GS) is a plant belonging to the family Asclepiadaceae that grows naturally in tropical and subtropical countries such as India, China, Southeast Asia, and Africa.Aqueous or alcoholic extracts of GS have the effect of suppressing sweet taste, while inhibiting sugar levels in the intestinal tract. It has also been found to have an absorption-suppressing effect, and can be used for medicinal purposes and low-calorie foods and drinks. It has also been found to have an anti-caries effect, and can be used as an anti-caries agent.
伝統的にＧＳを用いているインドでは乾燥葉自体を粉末
化して食用しており、糖尿病その他の病気の治療薬とし
て用いられている。その薬効成分はＧＳの水等による抽
出物にあると論じられており、下記ギムネマ酸を含む複
合成分の相互作用によると考えられている。In India, where GS is traditionally used, the dried leaves themselves are powdered and eaten, and are used as a treatment for diabetes and other diseases. It has been argued that the medicinal component lies in the extract of GS with water, etc., and is thought to be due to the interaction of complex components including gymnemic acid described below.
このような効果を示すＧＳの有効成分はギムネマ酸（以
下ＧＡと云う）と云われ、ギムネマ酸は八！〜Ａ４の同
族体があり、その基本構造は、トリテルペンでるギムネ
マゲニン（３β、１６β。The active ingredient in GS that exhibits such effects is called gymnemic acid (hereinafter referred to as GA), and gymnemic acid has eight! There are homologues of ~A4, whose basic structure is gymnemagenin (3β, 16β), which is a triterpene.
２１β、２２α、２３．２８−ヘキサヒドロキシオシア
ン−１２エン）の誘導体とＤ−グルクロン酸から成る配
糖体である。又トリテルペンの水酸基は種々の有機酸で
エステル化されており、有機酸の種類はそれぞれの同族
体で異っている。It is a glycoside consisting of a derivative of (21β, 22α, 23.28-hexahydroxyocyan-12ene) and D-glucuronic acid. Furthermore, the hydroxyl group of triterpenes is esterified with various organic acids, and the types of organic acids differ for each homolog.
ＧＳの利用に際しては、ＧＳを水又はアルコールで抽出
し１次いで濃縮した後噴霧乾燥した粉末として各種の用
途に用いられている。When using GS, GS is extracted with water or alcohol, first concentrated, and then spray-dried as a powder for various purposes.
しかしながら、このＧＳ抽出物は苦味が強く、食用及び
薬用への適用に大きな妨げとなっているが、有効な苦味
除去法は未だ確立されていない。However, this GS extract has a strong bitter taste, which greatly hinders its use in food and medicine, but an effective method for removing bitterness has not yet been established.
天然の配糖体は苦味を呈するものが多く、その苦味の低
減について各種の方法が考案され実用化されているが、
ＧＳ抽出物の苦味の低減には有効でない。Many natural glycosides have a bitter taste, and various methods have been devised and put into practical use to reduce the bitter taste.
It is not effective in reducing the bitterness of GS extract.
１が しようと る、 貞
本発明はＧＳ抽出物の服用に妨げとなる苦味を低減する
方法を提供することを目的とする。The purpose of the present invention is to provide a method for reducing the bitterness that hinders the administration of GS extracts.
口０発明の構成
１、 直 るための
本発明のＧＳ抽出物の苦味低減方法は、ＧＳ抽出物に、
その５重量倍以上の澱粉を加え、水相でサイクロデキス
トリン−グルコシル命トランスフェラーゼ（ｃｙｃｌｏ
ｄｅｘｔｒｉｎ ｇｌｕｃａｎｏ ｔｒａｎｓｆｅｒａ
ｓｅ：以下ＣＧＴと云う）を作用させてＧＳ抽出物中の
ＧＡにグルコースを転移させると共に、同時に生成する
γ−サイクロデキストリンによる包接を行わせることを
特徴とする。Structure 1 of the invention: The method for reducing the bitterness of a GS extract of the present invention for curing the bitterness of the GS extract comprises:
At least 5 times the weight of starch was added, and in the aqueous phase, cyclodextrin-glucosyl biotransferase (cyclodextrin-glucosyl biotransferase) was added.
dextrin glucano transfera
se: hereinafter referred to as CGT) to transfer glucose to GA in the GS extract, and at the same time cause inclusion by γ-cyclodextrin to be produced.
ＣＧＴはＢ、Ｍａｃｅｒａｎｓ、 Ｂ、Ｍｅｇａｔｅｒ
ｉｕｍ％Ｃが分泌する酵素で、Ｂ、Ｍａｃｅｒａｎｓ由
来のものはコンチザイム（天野製薬（財）製）の名で市
販されている。その特質は、澱粉単独に作用させるとサ
イクロデキス！・リン（以下ＣＤと云う）を生成し、澱
粉と配糖体が存在すると配糖体の糖部にグルコース残基
を転移させる作用がある。CGT is B, Macerans, B, Megater
The enzyme secreted by B. Macerans is commercially available under the name Contizyme (manufactured by Amano Pharmaceutical Co., Ltd.). Its characteristic is that when it acts on starch alone, it becomes cyclodextrin! - It produces phosphorus (hereinafter referred to as CD), and when starch and glycosides are present, it has the effect of transferring glucose residues to the sugar moieties of glycosides.
ＧＳの場合、有効成分であり且つ苦味成分であるＧＡの
基本構造から、そのＤ−グルクロン酸部位への酵素によ
るグルコース転移と疎水性トリテルペン部位のＣＤの包
接が行われる。In the case of GS, the basic structure of GA, which is an active ingredient and a bitter component, involves enzymatic glucose transfer to its D-glucuronic acid site and inclusion of CD at a hydrophobic triterpene site.
ＣＤにはα、β、γの３つの型があるが、包接して苦味
を抑える効果を有するのはγ型のみであり（後記参考側
参照）、ＣＧＴの作用により澱粉から生成したγ−ＣＤ
によりＧＳの半ば以上を包接するには、ＧＳ抽出物に、
その５重量倍以上、好ましくは１０重量倍以上の澱粉を
加える必要がある。There are three types of CD: α, β, and γ, but only the γ type has the effect of suppressing bitterness through inclusion (see reference side below), and γ-CD produced from starch by the action of CGT.
In order to include more than half of GS, in the GS extract,
It is necessary to add starch in an amount of 5 times or more by weight, preferably 10 times or more by weight.
以下実施例、比較例及び参考例により本発明の構成及び
効果を説明する。The structure and effects of the present invention will be explained below using Examples, Comparative Examples, and Reference Examples.
［試料調ｍ１
ＧＳの水又はアルコール抽出物には有効成分であるＧＡ
の他に葉緑素等の多くの物質が含まれており、これらの
中には苦味を呈する物質も少なくないので、実験の効果
を明確にするため、ＧＡ以外の苦味物質を下記の方法に
より前以って除去した。[Sample preparation m1 The water or alcohol extract of GS contains GA, which is an active ingredient.
In addition, it contains many other substances such as chlorophyll, and many of these substances have a bitter taste. Therefore, in order to clarify the effect of the experiment, bitter substances other than GA were previously prepared using the following method. I removed it.
ＧＳの含水エタノール抽出物の水溶液に塩酸を加え、ｐ
Ｈ１，０〜２．０として酸析し、析出した沈殿をエタノ
ールで抽出し抽出物を蒸発屹固した。乾固物を水に溶解
し、水飽和ｎ−ブタノールで抽出し、抽出したブタノー
ル層にジエチルエーテルを加え再結晶させた。結晶は遠
心分離し沈殿物を乾燥し粗ＧＡとした。なお必要な場合
はジエチルエーテル再結晶操作をさらに一回繰返しても
よい。Hydrochloric acid was added to an aqueous solution of a hydrous ethanol extract of GS, and p
Acid precipitation was carried out as H1.0 to 2.0, the precipitated precipitate was extracted with ethanol, and the extract was evaporated and solidified. The dried product was dissolved in water, extracted with water-saturated n-butanol, and diethyl ether was added to the extracted butanol layer for recrystallization. The crystals were centrifuged and the precipitate was dried to obtain crude GA. If necessary, the diethyl ether recrystallization operation may be repeated one more time.
こうして得られたＧＳ抽出物精製品（粗ＧＡ）は少量の
不純物を含むがＧＡの異性体の集合物であり、前述の各
種の効力を強力に示すが１強い苦味を呈する。The purified GS extract product (crude GA) thus obtained contains a small amount of impurities, but is a collection of isomers of GA, and strongly exhibits the various efficacies described above, but exhibits a strong bitter taste.
［比較例１］
前記の［ＧＡに３ｆｆｉ駿倍の澱粉を加えてＣＧＴを作
用させ、苦味の低減程度及びグルコース転移の確認をし
た。[Comparative Example 1] 3ffi of starch was added to the above-mentioned [GA and CGT was allowed to act, and the degree of reduction in bitterness and glucose transfer were confirmed.
粗ＧＡ４００ｍｇ及び可溶性澱粉１２００ｍｇをｌＯｍ
Ｊｌの酢酸バッファーでｐＨ６，０の水溶液とし、ＣＧ
Ｔとしてコンチザイムｌｌ０Ｕを加え５０℃で４８時間
反応させた。100mg of crude GA and 1200mg of soluble starch
Make an aqueous solution at pH 6.0 with Jl acetate buffer, and add CG
Contizyme 110U was added as T and reacted at 50°C for 48 hours.
ここでＩＵとは、ｐＨ５，５，０，０２Ｍの酢ｓ緩衝液
及び２Ｘ１０−３Ｍの塩化カルシウムを含む０．３ｆｆ
ｉ量％のソリュブルスターチ溶液５ｍｉに適当に希釈し
た酵素液０．２ｍｆＬを加え４０℃で１０分間反応した
後、その反応液０．５ｍＪＬをとり、０．０２Ｎ硫酸水
溶液１５ｍ２に混合して反応を停止させ、さらにこの反
応停止液にＯ，ＬＮヨウ素ヨウ化カリウム溶液０．２ｍ
ｆＬを加えて発色させ、ついで６６０ｎｍにおける吸光
度を測定して、４０℃で４０分間反応させることにより
ソリュブルスターチ１５ｍｇのヨウ素の呈色を完全に消
失させる酵素量のユニットをいう。Here, IU means 0.3ff containing vinegar s buffer of pH 5,5,0,02M and calcium chloride of 2X10-3M.
Add 0.2 mfL of an appropriately diluted enzyme solution to 5 m2 of a soluble starch solution of i% by weight, react at 40°C for 10 minutes, then take 0.5 mJL of the reaction solution, mix it with 15 m2 of a 0.02N sulfuric acid aqueous solution, and start the reaction. Stop the reaction, and add 0.2 m of O, LN iodine potassium iodide solution to the reaction stop solution.
It refers to the amount of enzyme that completely eliminates the coloration of iodine in 15 mg of soluble starch by adding fL to develop color, then measuring the absorbance at 660 nm, and reacting at 40°C for 40 minutes.
反応後沸騰水浴中で酵素を失活させ、苦味の評価および
薄層クロマトグラフィ（以下ＴＬＣと云う）によるグル
コース転移の確認を行った。After the reaction, the enzyme was inactivated in a boiling water bath, and bitterness was evaluated and glucose transfer was confirmed by thin layer chromatography (hereinafter referred to as TLC).
苦味は男女各５名づつのｌＯ大のパネルによる味覚試験
で評価した。Bitterness was evaluated by a taste test using a 10-sized panel of 5 men and 5 men.
ＴＬＣは反応前後の試料につき一次展開の後、分離した
スポットにグルコアミラーゼ（生化学工業■製）を噴霧
し二次展開した６反応前のＴＬＣは直線であり、反応後
は転移グルコース残基が分離していることからグルコー
ス転移を確認した。TLC was performed on samples before and after the reaction, and after primary development, glucoamylase (manufactured by Seikagaku Corporation) was sprayed onto the separated spots and secondary development was performed. 6 TLC before reaction was a straight line, and after reaction, transferred glucose residues were Glucose transfer was confirmed from the separation.
ＴＬＣ条件
プレート：メルクＨＰＴＬＣＡｒｔ ５Ｅ１３１展開溶
媒： ＣＨｚＣｌ：ＣＨ３０Ｈ：Ｈ２０冨８０：３５：
１０９色ｔｉｌｌ ： ２Ｎ Ｈ２ＳＯ４，０，５％
バニリン比較例１において粗ＧＡへのグルコース転移は
確認されたが、反応液の苦味は幾分弱くなった程度であ
り、グルコース転移だけでは苦味低減効果は殆ど認めら
れなかった。TLC condition plate: Merck HPTLCArt 5E131 developing solvent: CHzCl:CH30H:H20 concentration 80:35:
109 colors till: 2N H2SO4,0.5%
Although glucose transfer to crude GA was confirmed in Vanillin Comparative Example 1, the bitterness of the reaction solution was only slightly weakened, and almost no bitterness reducing effect was observed by glucose transfer alone.
［参考例］
ＣＤにより包接が行われることは各種の実験で判明して
いるが、ＣＤにはα、β、γの３つの型があり、いずれ
の型が苦味低減効果が優れているのかを見た。[Reference example] Various experiments have shown that inclusion occurs due to CD, but there are three types of CD: α, β, and γ, and which type is better in reducing bitterness? I saw it.
前記粗ＧＡ１００ｍｇに対して、α−１β−又はγ−Ｃ
Ｄ各１００ｍｇを水１０ｍ見に溶かし、２時間攪拌した
後苦味を見た。結果は次の通りである。For 100 mg of the crude GA, α-1β- or γ-C
100 mg of each of D was dissolved in 10 ml of water, stirred for 2 hours, and then checked for bitterness. The results are as follows.
α−ＣＤ 苦味あり
β−ＣＤ 苦味あり
γ−ＣＤ 苦味は弱くなっている従ってγ−ＣＤ
による包接のみが苦味低減効果のあることが判るが、γ
−ＣＤはＣＤの内でも高価であり、実際の使用ではコス
トアップとなる。α-CD Bitter β-CD Bitter γ-CD Bitterness is weaker, so γ-CD
It can be seen that only inclusion by γ has a bitterness reducing effect, but γ
-CDs are more expensive than other CDs, and the cost increases in actual use.
Ｂ、Ｎａｃｅｒａｎｓ由来のＣＧＴは、澱粉に作用させ
ると、たとえば９０分では、α：β：γ＝２．２：１．
０：０．７の割合でＣＤを生成するとされている。（ア
ミラーゼシンポジウム（１９７３）、８．Ｐ２１〜２７
；開田等）
またＣＤによる包接効果の効率が良いのは等モル比付近
であるとされている。ＧＡの平均分子量は約ａＯＯ１γ
−ＣＤの分子量は１２９７であるので、Ｓ粉からＣＧＴ
によるグルコース転移と、生成するγ−ＣＤによる包接
効果を期待するには多量の澱粉が必要であると予想され
る。B. When CGT derived from Nacerans acts on starch, for example, in 90 minutes, α:β:γ=2.2:1.
It is said that CDs are generated at a ratio of 0:0.7. (Amylase Symposium (1973), 8. P21-27
; Kaida et al.) Furthermore, it is said that the efficiency of the inclusion effect by CD is good when the molar ratio is around equimolar. The average molecular weight of GA is approximately aOO1γ
- Since the molecular weight of CD is 1297, CGT from S powder
It is expected that a large amount of starch is required to expect the glucose transfer by γ-CD and the inclusion effect by the generated γ-CD.
［実施例１及び２］
前記のＧＳ抽出物精製品（粗ＧＡ）１００ｍｇに対して
澱粉５００ｍｇ （実施例１）又は（実施例２）１５０
０ｍｇを１０ｍＪｌの２０ｍモル酢酸バッファー（ｐＨ
＝６．０）に溶解し、ＣＧＴとしてコンチザム１２０Ｕ
を加え５４℃で４８時間反応させ、反応終了後沸騰水浴
中で酵素を失活させたのち苦味を見た。又生成したγ−
ＣＤを測定した。結果を第１表に示す。[Examples 1 and 2] Starch 500 mg (Example 1) or (Example 2) 150 mg per 100 mg of the purified GS extract product (crude GA)
0mg to 10mJl of 20mmol acetate buffer (pH
= 6.0) and contisum 120U as CGT.
After the reaction was completed, the enzyme was deactivated in a boiling water bath and the bitter taste was examined. Also generated γ-
CD was measured. The results are shown in Table 1.
第１表
なおＣＤは、反応液にグルコアミラーゼを加え５０℃で
２００時間反応せ残存澱粉を分解し、沸騰水浴中で酵素
を失活させた後、高速液体クロマトグラフィー（ＨＰＬ
Ｃ）により測定した。Table 1: CD was prepared by adding glucoamylase to the reaction solution and reacting at 50°C for 200 hours to decompose the remaining starch, inactivating the enzyme in a boiling water bath, and then performing high performance liquid chromatography (HPL).
C).
ＩＰＩＣ条件
カラム Ｌｉｃｒｏｓｏｒｂ−ＮＨ２
検出 ＲＩ
溶媒 ＣＨ３ＣＮ：Ｈ２０富７１：２９実施例１の如
く粗ＧＡに対して５ｆｆｉｆｉ倍の澱粉を加えたた場合
８６ｍｇのγ−ＣＤが生成しＧＡの苦味は低減され、実
施例２の如く粗ＧＡに対して１５重量倍の澱粉を加えた
た場合１３３ｍｇのγ−ＣＤが生成しＧＡの苦味はなく
なった。IPIC condition column Licrosorb-NH2 detection RI solvent CH3CN:H20 richness 71:29 When 5ffifi times more starch was added to crude GA as in Example 1, 86 mg of γ-CD was produced and the bitterness of GA was reduced. When starch was added in an amount 15 times the weight of crude GA as in Example 2, 133 mg of γ-CD was produced and the bitterness of GA disappeared.
実施例２の場合の粗ＧＡとγ−ＣＤのモル比は見掛は上
１：０．８となるが、粗ＧＡは不純物を若干含有してい
るので、ＧＡとγ−ＣＤの比は実質的にほぼ等モル比と
なっていると考えられる。The molar ratio of crude GA to γ-CD in Example 2 is apparently 1:0.8, but since the crude GA contains some impurities, the ratio of GA to γ-CD is actually It is thought that the molar ratio is almost equal.
即ちＧＳ抽出物精製品である粗ＧＡに５重量倍以上、好
ましくは１０重量倍以上の澱粉を加えてＣＧＴを作用さ
せることにより、まず粗ＧＡにグルコース転移を生じ、
次いで過剰の澱粉からγ−ＣＤが生成され粗ＧＡを包接
することにより苦味が低減されるものと考えられる。That is, by adding at least 5 times by weight, preferably at least 10 times by weight of starch to crude GA, which is a purified product of GS extract, and allowing CGT to act, glucose transfer is first caused in the crude GA,
It is thought that γ-CD is then generated from excess starch and includes crude GA, thereby reducing bitterness.
なお粗ＧＡに対する最適澱粉量は粗ＧＡ中のＧＡ含有量
により変化するので一概には定められないが、過剰に使
用しても澱粉はＧＳ抽出物に比べ安価であり、コストア
ップにつながらない。Note that the optimal amount of starch for crude GA varies depending on the GA content in crude GA and cannot be determined unconditionally, but even if used in excess, starch is cheaper than GS extract and will not lead to an increase in cost.
又過剰に使用した場合、多量の澱粉が未反応物として反
応物中に混在することになるが、ＧＡの効果は強いので
、その効果を弱めることなく増量剤として用いることが
出来る。If used in excess, a large amount of starch will be mixed in the reaction product as an unreacted substance, but since the effect of GA is strong, it can be used as a bulking agent without weakening its effect.
実際のＧＳ抽出物の苦味低減方法においては。In the actual method for reducing bitterness of GS extract.
実施例１及び２に示したようにＧＳの水又はアルコール
抽出物を更に精製した原料を使用する必要はなく、ＧＳ
抽出物の酸析物を原料としても充分苦味は弱められ、実
用に耐えるものとなる。As shown in Examples 1 and 2, it is not necessary to use a raw material that is a water or alcoholic extract of GS that is further purified;
Even if the acid precipitate of the extract is used as a raw material, the bitterness will be sufficiently weakened and it will be suitable for practical use.
［実施例３］
ＧＳ乾燥葉４ｇを３０％エタノール４０ｍＭで３ｒｉｌ
ｉ１抽出し、抽出液を／ｉ発乾固して抽出物ｉｇを得た
。抽出物１ｇを水１０ｍ文で溶解し塩酸にてｐＨ１，５
に調整した。生成した沈殿は遠心分離により分離し、乾
燥した。[Example 3] 4g of GS dried leaves was mixed with 3ril of 40mM of 30% ethanol.
i1 extraction, and the extract was evaporated to dryness to obtain extract ig. Dissolve 1g of extract in 10ml of water and adjust to pH 1.5 with hydrochloric acid.
Adjusted to. The generated precipitate was separated by centrifugation and dried.
乾燥粉末３００ｍｇと澱粉３０００ｍｇを３０ｍ文の２
０ｍモル酢酸バッファー（ｐＨ６，０）に溶解し、ＣＧ
Ｔ （コンチザイム ）２５０Ｕを加え５４℃で４８
時間反応させた。反応終了後沸騰水浴水で１０分間加熱
し、酵素を失活させた後反応液は遠心分離し上清を減圧
濃縮した後屹煙し。300mg of dry powder and 3000mg of starch in 2 30m sentences
Dissolved in 0mM acetate buffer (pH 6,0), CG
Add 250U of T (contizyme) and heat at 54°C.
Allowed time to react. After the reaction was completed, the enzyme was heated in a boiling water bath for 10 minutes to inactivate the enzyme, and the reaction solution was centrifuged, the supernatant was concentrated under reduced pressure, and then smoked.
乾燥物３０００ ｍ ｇを得た。3000 mg of dry product was obtained.
この乾燥物は苦味が完全にないものであった。This dried product was completely free of bitterness.
１」
ギムネマ番シルベスタ抽出物に、その３重量倍の澱粉を
加え、水相でサイクロデキストリン拳グルコシル・トラ
ンスフェラーゼを作用させても苦味の低減は殆ど認めら
れないが（比較例１）、５重量倍の澱粉を加えて同様に
処理すれば明らかに苦味が減少したことが認められ（実
施例１）、１５５重量の澱粉を加えた場合（実施例２）
及び１０重量倍の澱粉を加えた場合（実施例３）には苦
味が感じられなくなる。1" Adding 3 times the weight of starch to Gymnema Sylvester extract and allowing cyclodextrin glucosyl transferase to act on it in the aqueous phase, almost no reduction in bitterness was observed (Comparative Example 1), but 5 times the weight of starch When 155% of starch was added and treated in the same manner, it was observed that the bitterness was clearly reduced (Example 1), and when 155% of starch was added (Example 2)
And when 10 times the weight of starch was added (Example 3), bitterness was no longer felt.
これはギムネマ・シルベスタ抽出物中のギムネマ酸への
グルコース転移及び同時に生成するγ−サイクロデキス
トリンによる包接と対応する効果であることが認められ
た。This effect was found to correspond to glucose transfer to gymnemic acid in the Gymnema sylvestre extract and inclusion by γ-cyclodextrin simultaneously produced.
ハ０発明の効果
ＧＳ抽出物の各種用途への適用に際して問題となる苦味
の低減が、安価な澱粉と市販の汀及した酵素の作用によ
り実施可能となり、安価な苦味低減ＧＳ抽出物を提供出
来る。又、七の方法は簡単であり実用化に適合した方法
である。Effects of the Invention The reduction of bitterness, which is a problem when applying GS extracts to various uses, can be achieved through the action of inexpensive starch and commercially available stagnant enzymes, making it possible to provide inexpensive GS extracts with reduced bitterness. . Furthermore, method 7 is simple and suitable for practical use.
Claims (1)
澱粉を加え、水相でサイクロデキストリン・グルコシル
・トランスフェラーゼを作用させてギムネマ・シルベス
タ抽出物中のギムネマ酸にグルコースを転移させると共
に、同時に生成するγ−サイクロデキストリンによる包
接を行わせることを特徴とするギムネマ・シルベスタ抽
出物の苦味低減方法。At least 5 times the weight of starch is added to the Gymnema sylvestre extract, and cyclodextrin glucosyl transferase is activated in the aqueous phase to transfer glucose to gymnemic acid in the Gymnema sylvestre extract, and at the same time produce γ. - A method for reducing the bitterness of a Gymnema sylvestre extract, which comprises clathrating it with cyclodextrin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62155303A JPH0687760B2 (en) | 1987-06-24 | 1987-06-24 | Method for reducing bitterness of Gymnema sylvestre extract |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62155303A JPH0687760B2 (en) | 1987-06-24 | 1987-06-24 | Method for reducing bitterness of Gymnema sylvestre extract |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPS642552A JPS642552A (en) | 1989-01-06 |
| JPH012552A true JPH012552A (en) | 1989-01-06 |
| JPH0687760B2 JPH0687760B2 (en) | 1994-11-09 |
Family
ID=15602951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62155303A Expired - Lifetime JPH0687760B2 (en) | 1987-06-24 | 1987-06-24 | Method for reducing bitterness of Gymnema sylvestre extract |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0687760B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0688908B2 (en) * | 1987-10-15 | 1994-11-09 | 東洋精糖株式会社 | How to remove the bitterness and astringency of Gymnema sylvestre leaf extract |
| US5484593A (en) * | 1991-05-28 | 1996-01-16 | Iwasaki; Kazuo | Diet composition comprising gymnema inodrum and a method for suppressing the absorption of saccharides |
| JP4528903B2 (en) * | 2002-03-11 | 2010-08-25 | 石川県 | Method for producing cyclodextrin inclusion product of plant-containing active ingredient |
| JP4203578B2 (en) * | 2002-07-23 | 2009-01-07 | 石川県 | Method for producing cyclodextrin inclusions of active ingredients containing water and livestock products |
| WO2011097620A1 (en) * | 2010-02-08 | 2011-08-11 | The Coca-Cola Company | Solubility enhanced terpene glycoside(s) |
-
1987
- 1987-06-24 JP JP62155303A patent/JPH0687760B2/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3060227B2 (en) | α-Glycosyl hesperidin, its production method and use | |
| US4557927A (en) | Food products and process for producing same | |
| EP1295533B1 (en) | Sweetener and process for producing the same | |
| TW293036B (en) | ||
| US10676496B2 (en) | Method for producing flavonoid inclusion compound | |
| JPH05981B2 (en) | ||
| BR112016007069B1 (en) | Process for producing a glycosyl stevia composition, glycosyl stevia composition, food ingredient, food, beverage, cosmetic or pharmaceutical product. | |
| JP2002528063A (en) | sweetener | |
| JP3043888B2 (en) | Colorectal cancer prophylactic agent containing glucomannan partial hydrolyzate as active ingredient | |
| JPH012552A (en) | Method for reducing bitterness of Gymnema sylvestre extract | |
| JPH11346792A (en) | Alpha-glycosylhesperidin, and production and application thereof | |
| US7713940B2 (en) | Water-soluble isoflavone composition, process for producing the same, and use thereof | |
| JPH0687760B2 (en) | Method for reducing bitterness of Gymnema sylvestre extract | |
| JPH07184597A (en) | Method for removing bitter taste, puckery taste and astringent taste from leaf extract of gymnema inodorum | |
| JP4051482B2 (en) | Pharmaceutical composition comprising α-glycosyl hesperidin | |
| JPH04364130A (en) | Soya saponin-containing food and soya saponin pharmaceutical preparation | |
| JP2003171328A (en) | Method for extracting and method for purifying effective substance | |
| JP3576594B2 (en) | Method for removing bitterness and astringency of sweet tea leaf extract | |
| JPS6037950A (en) | Method for improving taste of stevia sweetener | |
| CN113507842A (en) | Compositions comprising transglycosylated stevioside and transglycosylated rebaudioside A | |
| JPH0694473B2 (en) | β-glucosyl rubusoside, method for producing the same, and sweetener using the same | |
| WO2019093737A1 (en) | Composition containing allulose for improving taste quality | |
| JPS5980699A (en) | Gynosaponins | |
| JPS6241216B2 (en) | ||
| JPH05982B2 (en) |