JP2640066B2 - Isolation and purification method of soybean savonin and soybean saponin - Google Patents
Isolation and purification method of soybean savonin and soybean saponinInfo
- Publication number
- JP2640066B2 JP2640066B2 JP4277828A JP27782892A JP2640066B2 JP 2640066 B2 JP2640066 B2 JP 2640066B2 JP 4277828 A JP4277828 A JP 4277828A JP 27782892 A JP27782892 A JP 27782892A JP 2640066 B2 JP2640066 B2 JP 2640066B2
- Authority
- JP
- Japan
- Prior art keywords
- soybean
- saponin
- isolation
- savonin
- soybean saponin
- 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
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、大豆を出発原料として
用い、アルカリ処理を行なわずに真正サポニンとして単
離した大豆サポニンに関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a soybean saponin isolated as a true saponin without using an alkali treatment, using soybean as a starting material.
【０００２】[0002]
【従来の技術】従来、大豆サポニンとして、ソヤサポゲ
ノールＡをアグリコンとするソヤサポニンＡ１およびＡ
２、ソヤサポゲノールＢをアグリコンとするソヤサポニ
ンＩ、ＩＩおよびＩＩＩの５種類が報告されている。こ
れら大豆サポニンは、抗酸化、抗トロンビン、抗菌、降
コレステロール等の生理作用が報告され食品中の機能性
成分としても注目されている。Conventionally, as a soybean saponin, soyasaponin A 1 and A to aglycone soyasapogenol A
2. Five types of soyasaponins I, II and III using soyasapogenol B as aglycone have been reported. These soybean saponins have been reported to have physiological effects such as antioxidant, antithrombin, antibacterial, and cholesterol-lowering, and are also attracting attention as functional components in foods.
【０００３】大豆サポニンの単離とその構造は、北川ら
により上述の５種類が報告され、特許出願がなされてい
る。The above five types of soybean saponins have been isolated and their structures have been reported by Kitagawa et al., And a patent application has been filed.
【０００４】[0004]
【発明が解決しようとする課題】従来の単離、精製され
た大豆サポニンは、それの単離・精製の過程においてア
ルカリ処理していることから、必ずしも大豆種子中の真
正サポニンであるとは言えず、さらに、単離・精製手段
が極めて煩雑であることから時間的、経済的コストが高
い問題がある。The conventional isolated and purified soybean saponin has been treated with alkali in the process of isolation and purification, so it can be said that it is not necessarily genuine saponin in soybean seeds. Moreover, since the isolation / purification means is extremely complicated, there is a problem that time and economic costs are high.
【０００５】この問題を解決するための手段として、本
発明の出願人は、大豆胚軸を出発原料として用い、この
大豆胚軸から５０％含水メタノールにより大豆配糖体成
分を抽出し、その抽出液を直接ＯＤＳ（オクタデシルシ
リル）カラムに吸着し、しかるのちこれを８０％含水メ
タノールで溶出することにより、新規な大豆サポニンを
得る手段を開発し、特願平３−３５９４５７号（特開平
５−１７８８７９号）として出願した。As a means for solving this problem, the applicant of the present invention used soybean hypocotyl as a starting material, extracted soybean glycoside components from this soybean hypocotyl with 50% aqueous methanol, and extracted the soybean glycoside component. The solution was directly adsorbed to an ODS (octadecylsilyl) column, and then eluted with 80% aqueous methanol to develop a means for obtaining a novel soybean saponin. No. 178879).
【０００６】本発明は、この手段をさらに発展させて、
大豆真正サポニンとして単離した新たな大豆サポニンを
提供することを目的とする。The present invention further develops this means,
An object of the present invention is to provide a new soybean saponin isolated as soybean authentic saponin.
【０００７】[0007]
【課題を解決するための手段】本発明は、上述の目的の
ために、種々の研究と実験を重ねて得られた知見に基い
て完成したものである。SUMMARY OF THE INVENTION The present invention has been accomplished based on the knowledge obtained through various studies and experiments for the above-mentioned objects.
【０００８】即ち、大豆を出発原料として用い、この大
豆から５０％含水メタノールにより大豆配糖体成分を抽
出し、その抽出液を直接ＯＤＳ（オクタデシルシリル）
カラムに吸着させ、しかるのち、８０％含水メタノール
で溶出することにより、新規な大豆サポニン物質を得る
手段について、さらに研究を重ね、この手段における８
０％含水メタノールで溶出した溶出成分を、薄層クロマ
トグラフィーおよび、液体クロマトグラフィーにより分
析し、そこから選択した大豆サポニン溶出画分を各別に
集めて濃縮・乾固し、それぞれを大豆サポニン成分とし
て単離し、これら単離した大豆サポニン成分について、
核磁気共鳴スペクトル等の機器分析で検討した結果、That is, using soybean as a starting material, a soybean glycoside component is extracted from the soybean with 50% aqueous methanol, and the extract is directly subjected to ODS (octadecylsilyl).
Further studies were conducted on a means for obtaining a novel soybean saponin substance by adsorbing on a column and then eluting with 80% aqueous methanol.
The eluted components eluted with 0% aqueous methanol are analyzed by thin layer chromatography and liquid chromatography, and the soybean saponin eluted fractions selected therefrom are individually collected, concentrated and dried to obtain a soybean saponin component. Isolated, for these isolated soybean saponin components,
As a result of examination by instrumental analysis such as nuclear magnetic resonance spectrum,
【化１】およびAnd
【化２】ならびにEmbedded image and
【化３】に示す構造を持つ新規な大豆サポニン物質であ
ることの確認ができたことによるものである。This is because it was confirmed that it was a novel soybean saponin substance having the structure shown in the following formula.
【０００９】そして、このことから、本発明において
は、大豆真正サポニンとして、[0009] From the above, in the present invention, as a soybean authentic saponin,
【化１】に示す化学構造を持つ大豆サポニン、およびSoybean saponin having the chemical structure shown below, and
【化２】に示す化学構造を持つ大豆サポニン、ならびにSoybean saponin having the chemical structure shown below, and
【化３】に示す化学構造を持つ大豆サポニンを提起する
ものである。The present invention proposes a soybean saponin having the chemical structure shown below.
【００１０】[0010]
【実施例】以下、実施例により詳細に説明する。大豆を
粉砕後、５倍量の５０％含水メタノールで抽出し、この
抽出液をオクタデシルシランを詰めたカラム（５×７４
ｃｍ）に供し、８０％メタノールで溶出した。溶出成分
を薄層クロマトグラフィーおよび、液体クロマトグラフ
ィーで分析し、そこから選択したそれぞれの大豆サポニ
ン溶出画分を各別に集めて濃縮・乾固し、新たな大豆サ
ポニン物質を単離した。The present invention will be described below in detail with reference to examples. After pulverizing the soybeans, the soybeans were extracted with 5 times the volume of 50% aqueous methanol, and the extract was subjected to a column packed with octadecylsilane (5 × 74).
cm) and eluted with 80% methanol. The eluted components were analyzed by thin-layer chromatography and liquid chromatography, and the respective soybean saponin-eluting fractions selected therefrom were separately collected, concentrated and dried to isolate a new soybean saponin substance.
【００１１】単離した大豆サポニン成分のスペクトルデ
ータは、次の通りであった。 （１）ＦＡＢ−ＭＳ The spectrum data of the isolated soybean saponin component was as follows. (1) FAB-MS
【００１２】（２）核磁気共鳴スペクトル 表１ これらの結果から、新規大豆サポニンを３−０−［α−
Ｌ−ラムノピラノシル（１→２）−α−Ｌ−アラビノピ
ラノシル（１→２）−β−Ｄ−グルクロノピラノシル］
２２−０−（２，３−ジヒドロ−２，５−ジハイドロオ
キシ−６−メチル−４Ｈ−ピラン−４−オニル）ソヤサ
ポゲノールＢ、及び、３−０−［β−Ｄ−ガラクトピラ
ノシル（１→２）−β−Ｄ−グルクロノピラノシル］２
２−０−（２，３−ジヒドロ−２，５−ジハイドロオキ
シ−６−メチル−４Ｈ−ピラン−４−オニル（ソヤサポ
ゲノールＢ、ならびに３−０−［α−Ｌ−アラビノピラ
ノシル（１→２）−β−Ｄ−グルクロノピラノシル］２
２−０−（２，３−ジヒドロ−２，５−ジハイドロオキ
シ−６−メチル−４Ｈ−ピラン−４−オニル）ソヤサポ
ゲノールＢ、であると決定した。(2) Nuclear magnetic resonance spectrum Table 1 From these results, a novel soybean saponin was identified as 3-0- [α-
L-rhamnopyranosyl (1 → 2) -α-L-arabinopyranosyl (1 → 2) -β-D-glucuronopyranosyl]
22-0- (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-onyl) soyasapogenol B and 3-0- [β-D-galactopyranosyl ( 1 → 2) -β-D-glucuronopyranosyl] 2
2-0- (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-onyl (soyasapogenol B, and 3-0- [α-L-arabinopyranosyl ( 1 → 2) -β-D-glucuronopyranosyl] 2
2-0- (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-onyl) soyasapogenol B.
【００１３】[0013]
【発明の効果】以上説明したように、従来報告されてい
る大豆サポニンは、その精製過程においてアルカリ処理
していることから真正サポニンではないが、本発明によ
る大豆サポニンは真正サポニンであり、本発明において
はじめて得られたものである。As described above, the soybean saponins reported so far are not genuine saponins because they have been treated with alkali in the purification process, but the soybean saponins according to the present invention are genuine saponins. Is obtained for the first time.
【００１４】また、従来のサポニンの精製は、大豆か
ら、抽出・有機溶媒による分配・カラムクロマトグラフ
イなど数々の精製段階を必要とし、さらに、各段階にお
いて濃縮操作を必要とするため、時間的・経済的コスト
が高い。これに対して本発明は、抽出・クロマトグラフ
イの２段階で真正サポニンを精製できることから、その
コストも大幅に下げられるので、安価に真正サポニンが
得られる。In addition, conventional purification of saponin requires a number of purification steps from soybeans, such as extraction, partitioning with an organic solvent, and column chromatography, and further requires a concentration operation in each step. -High economic cost. On the other hand, according to the present invention, since genuine saponin can be purified in two stages of extraction and chromatography, the cost can be greatly reduced, and genuine saponin can be obtained at low cost.
【００１５】[0015]
【化１】３−０−［α−Ｌ−Ｒｈａｍｎｏｐｙｒａｎｏ
ｓｙｌ（１→２）−α−Ｌ−ａｒａｂｉｎｏｐｙｒａｎ
ｏｓｙｌ（１→２）−β−Ｄ−ｇｌｕｃｕｒｏｎｏｐｙ
ｒａｎｏｓｙｌ］２２−０−（２，３−ｄｉｈｙｄｒｏ
−２，５−ｄｉｈｙｄｒｏｘｙ−６−ｍｅｔｈｙｌ−４
Ｈ−ｐｙｒａｎ−４−ｏｎｙｌ）ｓｏｙａｓａｐｏｇｅ
ｎｏｌ ＢEmbedded image 3-0- [α-L-Rhamnopyrano
syl (1 → 2) -α-L-arabinopyran
osyl (1 → 2) -β-D-glucuronomy
ranosyl] 22-0- (2,3-dihydro
-2,5-dihydroxy-6-methyl-4
H-pyran-4-onyl) soyasapage
nol B
【化２】３−０−［β−Ｄ−ｇａｌａｃｔｏｐｙｒａｎ
ｏｓｙｌ（１→２）−β−Ｄ−ｇｌｕｃｕｒｏｎｏｐｙ
ｒａｎｏｓｙｌ］２２−０−（２，３−ｄｉｈｙｄｒｏ
−２，５−ｄｉｈｙｄｒｏｘｙ−６−ｍｅｔｈｙｌ−４
Ｈ−ｐｙｒａｎ−４−ｏｎｙｌ）ｓｏｙａｓａｐｏｇｅ
ｎｏｌ ＢEmbedded image 3-0- [β-D-galactopyran
osyl (1 → 2) -β-D-glucuronomy
ranosyl] 22-0- (2,3-dihydro
-2,5-dihydroxy-6-methyl-4
H-pyran-4-onyl) soyasapage
nol B
【化３】３−０−［α−Ｌ−ａｒａｂｉｎｏｐｙｒａｎ
ｏｓｙｌ（１→２）−β−Ｄ−ｇｌｕｃｒｏｎｏｐｙｒ
ａｎｏｓｙｌ］２２−０−（２，３−ｄｉｈｙｄｒｏ−
２，５−ｄｉｈｙｄｒｏｘｙ−６−ｍｅｔｈｙｌ−４Ｈ
−ｐｙｒａｎ−４−ｏｎｙｌ）ｓｏｙａｓａｐｏｇｅｎ
ｏｌ ＢEmbedded image 3-0- [α-L-arabinopyran
osyl (1 → 2) -β-D-glucronopyr
anosyl] 22-0- (2,3-dihydro-
2,5-dihydroxy-6-methyl-4H
-Pyran-4-onyl) soyasapogen
ol B
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｂ０１Ｄ 15/08 Ｂ０１Ｄ 15/08 Ｃ０７Ｈ 1/08 Ｃ０７Ｈ 1/08 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code Agency reference number FI Technical display location B01D 15/08 B01D 15/08 C07H 1/08 C07H 1/08
Claims (3)
（１→２）−α−Ｌ−アラビノピラノシル（１→２）−
β−Ｄ−グルクロノピラノシル］２２−０−（２，３−
ジヒドロ−２，５−ジハイドロオキシ−６−メチル−４
Ｈ−ピラン−４−オニル）ソヤサポゲノールＢからなる
大豆サポニン。(1) 3-0- [α-L-rhamnopyranosyl (1 → 2) -α-L-arabinopyranosyl (1 → 2)-
β-D-glucuronopyranosyl] 22-0- (2,3-
Dihydro-2,5-dihydroxy-6-methyl-4
(H-pyran-4-onyl) soybean saponin consisting of soyasapogenol B.
（１→２）−β−Ｄ−グルクロノピラノシル］２２−０
−（２，３−ジヒドロ−２，５−ジハイドロオキシ−６
−メチル−４Ｈ−ピラン−４−オニル）ソヤサポゲノー
ルＢからなる大豆サポニン。2. 2-0- [β-D-galactopyranosyl (1 → 2) -β-D-glucuronopyranosyl] 22-0
-(2,3-dihydro-2,5-dihydroxy-6
-Methyl-4H-pyran-4-onyl) soybean saponin consisting of soyasapogenol B.
（１→２）−β−Ｄ−グルクロノピラノシル］２２−０
−（２，３−ジヒドロ−２，５−ジハイドロオキシ−６
−メチル−４Ｈ−ピラン−４−オニル）ソヤサポゲノー
ルＢからなる大豆サポニン。3. 3-0- [α-L-arabinopyranosyl (1 → 2) -β-D-glucuronopyranosyl] 22-0
-(2,3-dihydro-2,5-dihydroxy-6
-Methyl-4H-pyran-4-onyl) soybean saponin consisting of soyasapogenol B.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4277828A JP2640066B2 (en) | 1992-09-22 | 1992-09-22 | Isolation and purification method of soybean savonin and soybean saponin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4277828A JP2640066B2 (en) | 1992-09-22 | 1992-09-22 | Isolation and purification method of soybean savonin and soybean saponin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06100583A JPH06100583A (en) | 1994-04-12 |
| JP2640066B2 true JP2640066B2 (en) | 1997-08-13 |
Family
ID=17588838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4277828A Expired - Fee Related JP2640066B2 (en) | 1992-09-22 | 1992-09-22 | Isolation and purification method of soybean savonin and soybean saponin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2640066B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL115110A (en) * | 1995-08-30 | 1997-08-14 | Chajuss Daniel | Soy molasses |
| JP2002500088A (en) * | 1998-01-12 | 2002-01-08 | ハー マジェスティ イン ライト オブ カナダ アズ リプレゼンティッド バイ ザ ミニスター オブ アグリカルチャー アンド アグリ−フード カナダ | Methods for isolation, recovery and purification of non-polar extracts |
| JP2010018552A (en) * | 2008-07-10 | 2010-01-28 | Akita Prefecture | Renin inhibitor containing soyasaponin i |
| JP2011195541A (en) * | 2010-03-23 | 2011-10-06 | Fuji Oil Co Ltd | Method for producing group b saponin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01246296A (en) * | 1988-03-25 | 1989-10-02 | Marusan I Kk | Method for separating and collecting components of different kinds in raw material containing glycoside |
| JPH0798831A (en) * | 1993-09-30 | 1995-04-11 | Kao Corp | Magnetic recording medium, its production and producing device |
-
1992
- 1992-09-22 JP JP4277828A patent/JP2640066B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01246296A (en) * | 1988-03-25 | 1989-10-02 | Marusan I Kk | Method for separating and collecting components of different kinds in raw material containing glycoside |
| JPH0798831A (en) * | 1993-09-30 | 1995-04-11 | Kao Corp | Magnetic recording medium, its production and producing device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06100583A (en) | 1994-04-12 |
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