JP3069652B2 - Soy Saponin Solubilization - Google Patents
Soy Saponin SolubilizationInfo
- Publication number
- JP3069652B2 JP3069652B2 JP3359573A JP35957391A JP3069652B2 JP 3069652 B2 JP3069652 B2 JP 3069652B2 JP 3359573 A JP3359573 A JP 3359573A JP 35957391 A JP35957391 A JP 35957391A JP 3069652 B2 JP3069652 B2 JP 3069652B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclodextrin
- soybean saponin
- soybean
- saponin
- soyasaponin
- 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 - Lifetime
Links
Landscapes
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、生理活性を保有する大
豆サポニンを、溶液の透明度が求められる飲料等に高い
溶解性ならびに溶解安定性をもたせたまま使用できる方
法を提供することを目的とし、シクロデキストリンを利
用して大豆サポニンの溶解性ならびに溶解安定性を向上
させる方法に関する。BACKGROUND OF THE INVENTION An object of the present invention is to provide a method for using soybean saponin having a physiological activity in a beverage or the like in which the transparency of a solution is required, while maintaining high solubility and dissolution stability. And a method for improving the solubility and dissolution stability of soybean saponins using cyclodextrin.
【０００２】[0002]
【従来の技術】サポニンは、植物の成分として広く分布
する配糖体で、利尿効果などにより古くから漢方薬とし
て使用されている。また、その中の大豆サポニンは、血
清コレステロール濃度を低下させるなどの効果が知られ
ている。2. Description of the Related Art Saponin is a glycoside widely distributed as a component of a plant, and has been used as a Chinese medicine for a long time due to its diuretic effect. In addition, soybean saponin therein is known to have effects such as lowering serum cholesterol concentration.
【０００３】大豆サポニンはSoyasaponin の混合物で、
成分としてSoyasaponin A1〜A6とSoyasaponin Ｉ〜III
およびＶが知られている。また、それらは糖鎖のトリテ
ルペン骨格への結合様式の違いによりSoyasaponin A 系
列（前者）とSoyasaponin B系列（後者）に区別され
る。[0003] Soy saponin is a mixture of Soyasaponin,
Soyasaponin A 1 ~A 6 as components with Soyasaponin I to III
And V are known. They are also classified into Soyasaponin A series (the former) and Soyasaponin B series (the latter) based on the difference in the manner of binding of the sugar chain to the triterpene skeleton.
【０００４】これまで大豆サポニンの生理活性を活かし
て、各種飲料等に大豆サポニンを添加する試みがなされ
ている。本来、大豆サポニンの水に対する溶解度はSoya
saponin A 系列で高く、Soyasaponin B 系列で低い傾向
がみられるが、両者とも溶液のpHやイオン強度により溶
解度が著しく低下したり、場合によってはゲル化する。
さらに完全に溶解した場合についても、加熱や冷凍によ
り不溶性画分が析出し、再溶解しなくなる。[0004] Attempts have been made to add soybean saponin to various beverages and the like by utilizing the physiological activity of soybean saponin. Originally, the solubility of soybean saponin in water is Soya
The tendency is high in the saponin A series and low in the Soyasaponin B series, but both significantly decrease the solubility or gelate depending on the pH and ionic strength of the solution.
Further, even when completely dissolved, an insoluble fraction precipitates due to heating or freezing and does not redissolve.
【０００５】[0005]
【発明が解決しようとする課題】そこで、本発明は大豆
サポニンを効率よく水に溶解させることと同時に、加
熱、冷凍、pHやイオン強度の変化といった苛酷な条件下
における大豆サポニン水溶液の濁りの発生やゲル化を防
ぐ方法を提供することを目的としている。SUMMARY OF THE INVENTION Accordingly, the present invention provides a method for efficiently dissolving soybean saponin in water and, at the same time, generating turbidity of an aqueous soybean saponin solution under severe conditions such as heating, freezing, and changes in pH and ionic strength. And a method for preventing gelation.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、上記課題
を解決するため種々研究を行った結果、大豆サポニンを
溶解させるに際し、ある条件を満たしてシクロデキスト
リンを共存させることにより、大豆サポニンの溶解性を
向上させることができると共に、溶液の安定性を著しく
上昇させることができることを見出して本発明を完成し
た。Means for Solving the Problems The present inventors have conducted various studies to solve the above-mentioned problems, and as a result, when soybean saponin is dissolved, soybean saponin is dissolved by satisfying certain conditions and coexisting with cyclodextrin. It has been found that the solubility of the compound can be improved and the stability of the solution can be remarkably increased.
【０００７】具体的には、大豆サポニンに対しモル比が
0.5〜５となるようにシクロデキストリンを添加し、攪
拌等により大豆サポニンにシクロデキストリンを作用さ
せて可溶化する。シクロデキストリンの添加は、大豆サ
ポニンを水に加える前でも後でも、さらには同時に行っ
てもよい。大豆サポニンに対するシクロデキストリンの
作用については不明であるが、大豆サポニンがシクロデ
キストリンに適度に包接されるものと推定される。[0007] Specifically, the molar ratio to soybean saponin is
Cyclodextrin is added so as to have a concentration of 0.5 to 5, and the soybean saponin is allowed to act on the soybean saponin by stirring or the like to solubilize. The cyclodextrin may be added before or after adding soybean saponin to the water, or even at the same time. Although the action of cyclodextrin on soybean saponin is unknown, it is presumed that soybean saponin is appropriately included in cyclodextrin.
【０００８】大豆サポニンの可溶化のために用いられる
シクロデキストリンとしては、α−，β−，γ−シクロ
デキストリン、あるいは修飾された各種のシクロデキス
トリン例えば、グルコシルシクロデキストリン、マルト
シルシクロデキストリン、ヒドロキシアルキルシクロデ
キストリンなどが挙げられるが、特に、γ−シクロデキ
ストリンを用いるとより効果的である。As the cyclodextrin used for solubilizing soybean saponin, α-, β-, γ-cyclodextrin or various modified cyclodextrins such as glucosylcyclodextrin, maltosylcyclodextrin, hydroxyalkyl Cyclodextrin and the like can be mentioned. Particularly, use of γ-cyclodextrin is more effective.
【０００９】本発明において最も重要なことは、大豆サ
ポニンを可溶化させるために使用するシクロデキストリ
ンの量を限定した点である。大豆サポニンを可溶化する
ために必要なシクロデキストリンの量は、大豆サポニン
の種類やシクロデキストリンの種類によって異なるが、
総じて、大豆サポニンに対するシクロデキストリンのモ
ル比が 0.5〜５の範囲内、好ましくは１〜５の範囲内で
あることが望ましい。大豆サポニンに対するシクロデキ
ストリンのモル比が 0.5以下ではシクロデキストリンの
充分な可溶化機能が発揮されず、大豆サポニンの溶解性
は上がらない。一方、モル比が５以上では経済的に不利
なばかりか、包接化合物が析出する現象がみられ、大豆
サポニンの溶解安定性に問題が生じ、透明安定な水溶液
は得られなくなる。つまり大豆サポニンに対するシクロ
デキストリンのモル比を考慮することなく、シクロデキ
ストリンを添加するだけでは期待する効果が得られな
い。多くの実験を行った結果、大豆サポニンに対するシ
クロデキストリンの量は、シクロデキストリンの種類に
よって異なるが、好ましくはモル比で１以上である。Most importantly in the present invention is that the amount of cyclodextrin used to solubilize soybean saponins is limited. The amount of cyclodextrin required to solubilize soybean saponins depends on the type of soybean saponin and the type of cyclodextrin,
In general, it is desirable that the molar ratio of cyclodextrin to soybean saponin be in the range of 0.5-5, preferably in the range of 1-5. If the molar ratio of cyclodextrin to soybean saponin is 0.5 or less, a sufficient solubilizing function of cyclodextrin will not be exhibited, and the solubility of soybean saponin will not increase. On the other hand, when the molar ratio is 5 or more, not only is it economically disadvantageous, but also a phenomenon that an inclusion compound is precipitated is observed, and there is a problem in dissolution stability of soybean saponin, and a transparent and stable aqueous solution cannot be obtained. That is, the expected effect cannot be obtained only by adding cyclodextrin without considering the molar ratio of cyclodextrin to soybean saponin. As a result of many experiments, the amount of cyclodextrin to soybean saponin varies depending on the type of cyclodextrin, but is preferably 1 or more in molar ratio.
【００１０】これらの手段により得られた大豆サポニン
の溶液は、溶液のまま使用するか、あるいは凍結乾燥等
の乾燥手段により粉末化してから各種食品材料等への添
加物として利用することができる。The soybean saponin solution obtained by these means can be used as it is, or can be used as an additive to various food materials after being powdered by drying means such as freeze-drying.
【００１１】[0011]
【発明の効果】本発明によれば、大豆サポニンを溶解さ
せるのに際し、溶解状態を維持できるような量のシクロ
デキストリンを存在させることにより、大豆サポニンの
溶解性を向上せしめ得ると共に、その溶液の安定性を著
しく上昇させることができる。また、pHやイオン強度の
違いにより起こる大豆サポニン溶液のゲル化を完全に抑
えることができる。本発明の可溶化法は、大豆サポニン
のうち、Soyasaponin Ａ系列を主体とする大豆サポニ
ン、すなわちSoyasaponin A1、A2、A3、A4、A5、A6また
はそれらのアセチル化体、もしくはそれらの混合物を主
体とする大豆サポニンに適用できる。According to the present invention, the solubility of soybean saponin can be improved by dissolving soybean saponin in the presence of an amount of cyclodextrin that can maintain the solubilized state. Stability can be significantly increased. In addition, gelation of the soybean saponin solution caused by differences in pH and ionic strength can be completely suppressed. The solubilization method of the present invention uses soybean saponin.
Among them, soy saponi mainly composed of Soyasaponin A series
Down, i.e. Soyasaponin A 1, A 2, A 3, A 4, A 5, A 6 also
Waso these acetyl embodying or main mixtures thereof,
It can be applied to soybean saponins to be made.
【００１２】[0012]
【実施例】次に、実施例を挙げて本発明を説明するが、
本発明はこれらに限られるものではない。Next, the present invention will be described with reference to examples.
The present invention is not limited to these.
【００１３】実施例１ 大豆をヘキサンで脱脂後、アルコールで抽出し、その抽
出液を弱塩基性イオン交換樹脂で処理した。こうして得
られたSoyasaponin を多く含む画分を、さらに合成吸着
剤で分画してSoyasaponin A 系列を多く含む画分（Soya
saponin 含量85％）を得た。これらを濃縮、乾燥させた
もの 0.3ｇを水 100mlに添加し、室温で攪拌して溶解さ
せた後、pHをクエン酸で３に調節した。しかる後にγ−
シクロデキストリン（塩水港精糖製 純度98.5％）をそ
れぞれ 0.1、0.2 、0.3 、0.4 、0.6 、0.8 、1.0 、
2.0、5.0 ｇ添加して攪拌した後、80℃で60分加熱し、
加熱後５℃で一晩冷却した。再び80℃で60分加熱し、冷
却する操作を合計で３回行い、溶液の状態を観察した。
その後溶液を５℃で10日間保存し、−20℃の冷凍庫で凍
結させてから常温で融解させる操作を２回行い溶液の状
態を観察した。対照には、γ−シクロデキストリンを添
加しない大豆サポニン溶液を用いた。表１に示した様
に、大豆サポニンに対するγ−シクロデキストリンの添
加モル比が１〜1.5 （添加量で 0.4ｇ〜 0.6ｇ）の時
に、溶解性ならびに安定性が極めて増大した。Example 1 Soybeans were defatted with hexane, extracted with alcohol, and the extract was treated with a weakly basic ion exchange resin. The soyasaponin-rich fraction thus obtained was further fractionated with a synthetic adsorbent and fractionated with a soyasaponin A-series fraction (Soyasaponin A).
saponin content of 85%). After concentrating and drying these, 0.3 g was added to 100 ml of water, and dissolved by stirring at room temperature, and the pH was adjusted to 3 with citric acid. Then γ-
0.1%, 0.2, 0.3, 0.4, 0.6, 0.8, 1.0,
After adding 2.0 and 5.0 g and stirring, heat at 80 ° C for 60 minutes,
After heating, the mixture was cooled at 5 ° C. overnight. The operation of heating again at 80 ° C. for 60 minutes and cooling was performed three times in total, and the state of the solution was observed.
Thereafter, the solution was stored at 5 ° C. for 10 days, frozen twice in a freezer at −20 ° C., and then thawed at room temperature twice to observe the state of the solution. As a control, a soybean saponin solution to which γ-cyclodextrin was not added was used. As shown in Table 1, when the molar ratio of γ-cyclodextrin to soybean saponin was 1 to 1.5 (0.4 g to 0.6 g in the amount added), the solubility and the stability were extremely increased.
【００１４】 表中の記号は溶液の状態を表す ○：濁りおよび沈澱なし、 △：若干の濁りあるいは沈
澱あるが実用上問題なし、 ×：濁りあるいは沈澱あり 大豆サポニンの分子量は、Soyasaponin の組成比より求
めた。[0014] The symbols in the table represent the state of the solution. ：: No turbidity or precipitation, Δ: Slightly turbid or precipitated, but no problem in practical use, ×: Turbidity or precipitated. .
【００１５】実施例２ 大豆をヘキサンで脱脂後、アルコールで抽出し、その抽
出液を弱塩基性イオン交換樹脂で処理した。こうして得
られたSoyasaponin Ａを多く含む画分（Soyasaponin 含
量 85％）の乾燥物 0.4ｇを、あらかじめγ−シクロデ
キストリン 0.5ｇを溶解させておいた水 100mlに添加
し、室温で攪拌して溶解させた。得られた溶液に80℃で
60分加熱後放冷する操作を２回行い、可視光におけるス
ペクトルをとって濁りの評価をした。次にその試料を、
−20℃で凍結させた後室温で溶解させる操作を２回行
い、可視光におけるスペクトルをとって濁りの評価をし
た。対照には、γ−シクロデキストリンを共存させない
大豆サポニン溶液を用いた。図１に示した様に、γ−シ
クロデキストリンを共存させることにより大豆サポニン
溶液の溶解安定性は著しく高くなり、加熱や冷凍によっ
ても濁りを生じなかった。Example 2 Soybeans were defatted with hexane, extracted with alcohol, and the extract was treated with a weakly basic ion exchange resin. 0.4 g of the dried fraction containing a large amount of Soyasaponin A (Soyasaponin content: 85%) thus obtained was added to 100 ml of water in which 0.5 g of γ-cyclodextrin had been dissolved in advance, and stirred at room temperature to dissolve. Was. At 80 ° C to the resulting solution
The operation of cooling after heating for 60 minutes was performed twice, and the turbidity was evaluated by taking a spectrum in visible light. Next, the sample is
The operation of freezing at −20 ° C. and then melting at room temperature was performed twice, and the turbidity was evaluated by taking a spectrum in visible light. As a control, a soybean saponin solution without γ-cyclodextrin was used. As shown in FIG. 1, the coexistence of γ-cyclodextrin significantly improved the solubility stability of the soybean saponin solution, and did not cause turbidity even by heating or freezing.
【図１】シクロデキストリン（ＣＤ）の添加による大豆
サポニン溶液の溶解安定性を示すグラフである。FIG. 1 is a graph showing the dissolution stability of a soybean saponin solution by addition of cyclodextrin (CD).
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) A61K 35/78 A61K 47/40 C07H 15/256 ＢＩＯＳＩＳ（ＤＩＡＬＯＧ) ＣＡ（ＳＴＮ) ＭＥＤＬＩＮＥ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 7 , DB name) A61K 35/78 A61K 47/40 C07H 15/256 BIOSIS (DIALOG) CA (STN) MEDLINE (STN)
Claims (3)
り、Soyasaponin Ａ系列を主体とする大豆サポニンと該
大豆サポニンに対してモル比が 0.5〜５になる量のγ−
シクロデキストリンを共存させ、水以外の溶媒を併用し
ないことを特徴とする大豆サポニンの可溶化法。1. A soybean saponin having a Soyasaponin A series as a main component and a soybean saponin dissolved in water.
The amount of γ- in a molar ratio of 0.5 to 5 with respect to soybean saponin
Coexist with cyclodextrin and use a solvent other than water
A method for solubilizing soybean saponins, characterized in that there is no soybean saponin.
キストリンである請求項第１項記載の方法。2. The method according to claim 1, wherein the cyclodextrin is a branched γ-cyclodextrin.
A3、A4、A5、A6またはそれらのアセチル化体、もしくは
それらの混合物である請求項第１項記載の方法。3. The method according to claim 1, wherein the soybean saponins are Soyasaponin A 1 , A 2 ,
A 3, A 4, A 5 , A 6 , or their acetyl embodying or method as in claim 1 wherein a mixture thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3359573A JP3069652B2 (en) | 1991-12-31 | 1991-12-31 | Soy Saponin Solubilization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3359573A JP3069652B2 (en) | 1991-12-31 | 1991-12-31 | Soy Saponin Solubilization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05186359A JPH05186359A (en) | 1993-07-27 |
| JP3069652B2 true JP3069652B2 (en) | 2000-07-24 |
Family
ID=18465195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3359573A Expired - Lifetime JP3069652B2 (en) | 1991-12-31 | 1991-12-31 | Soy Saponin Solubilization |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3069652B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2815255A1 (en) * | 2001-01-23 | 2002-04-19 | Oreal | Composition for use in cosmetics, comprises at least one derivative of sapogenin and at least one solubilizing agent such as non-emulsifying esters of fatty acids and-or alcohols, or vegetable oils, and branched fatty alcohols |
| FR2815256A1 (en) * | 2001-01-23 | 2002-04-19 | Oreal | Composition for cosmetic use comprises at least one derivative of sapogenin, preferably of hecogenin, and at least one solubilizing agent such as organic lipophilic UV filters |
| JP4978209B2 (en) * | 2007-01-22 | 2012-07-18 | 株式会社イヅツみそ | Method for producing freeze-dried miso |
| JP2010018552A (en) * | 2008-07-10 | 2010-01-28 | Akita Prefecture | Renin inhibitor containing soyasaponin i |
| JP5500821B2 (en) * | 2008-12-25 | 2014-05-21 | ハウス食品グループ本社株式会社 | Saponin with reduced bitterness |
-
1991
- 1991-12-31 JP JP3359573A patent/JP3069652B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05186359A (en) | 1993-07-27 |
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