JPS61129134A - Purification of saponin obtained from soybean - Google Patents
Purification of saponin obtained from soybeanInfo
- Publication number
- JPS61129134A JPS61129134A JP59251413A JP25141384A JPS61129134A JP S61129134 A JPS61129134 A JP S61129134A JP 59251413 A JP59251413 A JP 59251413A JP 25141384 A JP25141384 A JP 25141384A JP S61129134 A JPS61129134 A JP S61129134A
- Authority
- JP
- Japan
- Prior art keywords
- soybean
- methanol
- ethanol
- saponin
- acetone
- 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.)
- Pending
Links
- 235000010469 Glycine max Nutrition 0.000 title claims abstract description 17
- 244000068988 Glycine max Species 0.000 title claims abstract description 17
- 229930182490 saponin Natural products 0.000 title claims abstract description 17
- 150000007949 saponins Chemical class 0.000 title claims abstract description 17
- 239000001397 quillaja saponaria molina bark Substances 0.000 title claims abstract description 15
- 238000000746 purification Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011347 resin Substances 0.000 claims abstract description 7
- 229920005989 resin Polymers 0.000 claims abstract description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000284 extract Substances 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 4
- 238000001179 sorption measurement Methods 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- 239000002808 molecular sieve Substances 0.000 abstract description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003463 adsorbent Substances 0.000 abstract 4
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 abstract 3
- 235000008696 isoflavones Nutrition 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 abstract 2
- 238000005406 washing Methods 0.000 abstract 2
- 238000002523 gelfiltration Methods 0.000 abstract 1
- 150000002515 isoflavone derivatives Chemical class 0.000 abstract 1
- 210000001161 mammalian embryo Anatomy 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 235000017709 saponins Nutrition 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000007240 daidzein Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は低級アルコール、例えばメタノール、エタノー
ル、含水ｎ−１タノール等又は、その酸性含水物にて大
豆胚芽よシ抽出し、濃縮后水を加えＨｐ−２０又はＸＡ
Ｄ −２等の吸着樹脂に吸着せしめ、１０〜４０％メタ
ノール或はエタノール又はアセトン等で洗浄し、７０〜
８０チメタノール、或はエタノール、又はアセトン等で
溶出することに関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention involves extracting soybean germ with a lower alcohol, such as methanol, ethanol, hydrous n-1 tanol, etc., or an acidic hydrous thereof, and then adding water after concentration to extract Hp-20 or XA.
Adsorb onto adsorption resin such as D-2, wash with 10-40% methanol, ethanol, acetone, etc.
This relates to elution with 80 timethanol, ethanol, acetone, or the like.
０産業上の利用分野
大豆よシのインフラボン類を殆んど含まない収率のよい
サポニン精製。更に又分子篩例えばＬＨ−２０ＬＨ−６
０、）ヨノ々−ル等力うムクロマトニカけることによシ
、インク２ゲンを含まないサポニン分画を容易に得るこ
とができる。0 Industrial field of use Purification of saponin from soybean with high yield and almost no infravones. Furthermore, molecular sieves such as LH-20LH-6
0.) A saponin fraction that does not contain ink 2 can be easily obtained by filtering it using a chromatonic filter.
０従来の技術
従来、公知の方法によればサポニン類は、その精製単離
にあたシ、アルコール抽出ののち、シリカゲルカラムク
ロマトグラフィー、もしくは、カウンターカレントディ
ストリビュータ−などが用いられており、サポニンの大
量単離には、困難な点が多かった。0 Prior Art Conventionally, according to known methods, saponins are purified and isolated using silica gel column chromatography or counter current distributor after alcohol extraction. There were many difficulties in mass isolation.
大豆成分の中で、サポニンの精製に於て、最も問題とな
るのは、ダイゼイン、ダニスティン等ノインフラデンで
ある。これらは、溶媒転溶による抽出工程で、サポニン
と分離することが困難であり、さらに、これらイソフ：
）Ｍン類は、女性ホルモン様作用を有し、哺乳類に不妊
症をはじめとする副作用を惹起せしめることが知られて
いる。Among the soybean components, the most problematic in the purification of saponins are noinfladenes such as daidzein and danistine. These are difficult to separate from saponin in the extraction process by solvent transfer, and furthermore, these isophores:
) Mants have female hormone-like effects and are known to cause side effects such as infertility in mammals.
０発明が解決しようとする問題点
そこです４二ンを長期間、より安全に服用するためには
、インフラボン類との分離が必須であると考えられる。This is the problem that the invention aims to solve.In order to take 42-ion more safely for a long period of time, it is considered essential to separate it from infravones.
０問題を解決するための手段
今回、発明者は、Ｈｐ −２０等、吸着樹脂によるステ
、グワイズエリュウジ冒ン（５ｔｅｐ ｖｌｓｅ・１ｕ
ｔｌｏｎ ）及び、ＬＨ−２０カラムクロマトを組み合
わせることにより、インフラ？ンと、サポニンを殆んど
完全に分離することに成功し、しかも、拳法は、大量処
理が可能で、工業的に精製サポニンを採取し得るもので
ある。Means to Solve the 0 Problem This time, the inventor has developed a step using an adsorption resin such as Hp-20,
tlon) and LH-20 column chromatography. The method succeeded in almost completely separating saponin from saponin, and furthermore, it is possible to process large quantities of saponin, and industrially, purified saponin can be obtained.
又、原料として、大豆稽皮、もしくは、大豆胚芽を用い
ることによシ、大豆粉に比べ４．３倍サポニンを多く採
取することができた。Furthermore, by using soybean peel or soybean germ as a raw material, it was possible to collect 4.3 times more saponin than soybean flour.
０作 用
本発明方法に依ればインフ：１７ケン類を殆んど除去し
たす／ニンを精製し得る作用がある００実施例
大豆胚芽１ゆを０．０ＯＩＮ−ＨＣＪ？・９０％メタノ
ール３１で抽出し、ｎ−へ中サン１１を加え３回脱脂し
た。抽出液の溶媒を減圧下で留去した後、水で２１とし
吸着樹脂Ｈｐ−２０に付した。２０チ及び７０チアセト
ンで溶出し、後者を減圧濃縮して２４．３８ｇの結晶を
得た。そのうち５．５０．Ｆを９９チメタノール２０Ｗ
ｔに溶解し、５ｅｐｈａｄｅｘ ＬＨ−２０ｒル濾過ク
ロマトグラフイーだ付した。溶出液を薄層クロマトグラ
フィー〔担体＝シリカグル６０Ｆ２５４、展開溶媒＝ブ
タノール・酢酸・水（３；１：１）、発色剤＝１％硫酸
第２セリウム１０％硫酸溶液噴霧〕で倹し、Ｒｆ約０．
４に出現するサポニンのフラクションを分取した。各フ
ラクションを減圧濃縮して３．１０ｇの結晶を得た。収
率１．３８％。0 Effect: According to the method of the present invention, 0.0 OIN-HCJ? - Extracted with 90% methanol 31, added Nakasan 11 to n- and defatted three times. After distilling off the solvent of the extract under reduced pressure, the extract was diluted with water and applied to adsorption resin Hp-20. Elution was carried out with 20 thiacetone and 70 thiacetone, and the latter was concentrated under reduced pressure to obtain 24.38 g of crystals. 5.50 of them. F 99 timeethanol 20W
The solution was dissolved in water and subjected to 5ephadex LH-20ml filtration chromatography. The eluate was purified by thin layer chromatography [carrier = silica glu 60F254, developing solvent = butanol/acetic acid/water (3:1:1), color former = 1% ceric sulfate, 10% sulfuric acid solution spray], and the Rf was approx. 0.
The fraction of saponin appearing in 4 was collected. Each fraction was concentrated under reduced pressure to obtain 3.10 g of crystals. Yield 1.38%.
手続補正書（自発） 昭和６０年１２月２７日Procedural amendment (voluntary) December 27, 1985
Claims (1)
含水ｎ−ブタノール等又は、その酸性含水物にて大豆よ
り抽出し、濃縮后水を加え Ｈｐ−２０又はＸＡＤ−２等の吸着樹脂に吸着せしめ、
１０〜４０％メタノール或はエタノール又はアセトン等
で洗浄し、７０〜８０％メタノール、或はエタノール、
又はアセトン等で溶出することを特徴とする大豆よりの
サポニンの精製法。 ２、抽出原料を大豆胚芽とする事を特徴とする特許請求
の範囲第１項記載の大豆よりのサポニンの精製法。 ３、抽出原料を大豆種皮とする事を特徴とする特許請求
の範囲第１項記載の大豆よりのサポニンの精製法。[Claims] 1. Lower alcohols, such as methanol, ethanol,
Extract from soybeans with hydrated n-butanol or its acidic hydrate, add water after concentration, and adsorb onto adsorption resin such as Hp-20 or XAD-2.
Wash with 10-40% methanol, ethanol, acetone, etc., and wash with 70-80% methanol or ethanol,
Or a method for purifying saponin from soybean, which is characterized by elution with acetone or the like. 2. The method for purifying saponin from soybeans according to claim 1, characterized in that the raw material for extraction is soybean germ. 3. The method for purifying saponin from soybeans according to claim 1, characterized in that the raw material for extraction is soybean seed coat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59251413A JPS61129134A (en) | 1984-11-28 | 1984-11-28 | Purification of saponin obtained from soybean |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59251413A JPS61129134A (en) | 1984-11-28 | 1984-11-28 | Purification of saponin obtained from soybean |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61129134A true JPS61129134A (en) | 1986-06-17 |
Family
ID=17222470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59251413A Pending JPS61129134A (en) | 1984-11-28 | 1984-11-28 | Purification of saponin obtained from soybean |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61129134A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7560131B2 (en) * | 2002-12-24 | 2009-07-14 | Fuji Oil Company, Limited | High solubility composition with high isoflavone concentration and process of producing same |
| US7638643B2 (en) * | 2002-03-14 | 2009-12-29 | Fuji Oil Company, Limited | Process for producing soybean saponin-containing material |
| JP2011195541A (en) * | 2010-03-23 | 2011-10-06 | Fuji Oil Co Ltd | Method for producing group b saponin |
| CN107260777A (en) * | 2017-06-28 | 2017-10-20 | 南京中医药大学 | A kind of fiveleaf akebia fruit with antitumor activity refines total saposins and its application |
-
1984
- 1984-11-28 JP JP59251413A patent/JPS61129134A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7638643B2 (en) * | 2002-03-14 | 2009-12-29 | Fuji Oil Company, Limited | Process for producing soybean saponin-containing material |
| US7560131B2 (en) * | 2002-12-24 | 2009-07-14 | Fuji Oil Company, Limited | High solubility composition with high isoflavone concentration and process of producing same |
| JP2011195541A (en) * | 2010-03-23 | 2011-10-06 | Fuji Oil Co Ltd | Method for producing group b saponin |
| CN107260777A (en) * | 2017-06-28 | 2017-10-20 | 南京中医药大学 | A kind of fiveleaf akebia fruit with antitumor activity refines total saposins and its application |
| CN107260777B (en) * | 2017-06-28 | 2020-12-08 | 南京中医药大学 | A kind of refined total saponin from Augusta with antitumor activity and its application |
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