JPH04217629A - Production of saponin form hypocotyl of soybean - Google Patents
Production of saponin form hypocotyl of soybeanInfo
- Publication number
- JPH04217629A JPH04217629A JP2412328A JP41232890A JPH04217629A JP H04217629 A JPH04217629 A JP H04217629A JP 2412328 A JP2412328 A JP 2412328A JP 41232890 A JP41232890 A JP 41232890A JP H04217629 A JPH04217629 A JP H04217629A
- Authority
- JP
- Japan
- Prior art keywords
- saponin
- fraction
- water
- alcohol
- soybean
- 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
- 150000007949 saponins Chemical group 0.000 title claims abstract description 55
- 235000010469 Glycine max Nutrition 0.000 title claims abstract description 22
- 244000068988 Glycine max Species 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229930182490 saponin Natural products 0.000 claims abstract description 54
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims abstract description 52
- 239000012223 aqueous fraction Substances 0.000 claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000002632 lipids Chemical class 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 13
- 238000000605 extraction Methods 0.000 claims description 4
- 235000021374 legumes Nutrition 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 abstract description 2
- 150000001720 carbohydrates Chemical class 0.000 abstract 2
- 235000017709 saponins Nutrition 0.000 description 44
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000002034 butanolic fraction Substances 0.000 description 3
- 238000005238 degreasing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 and for example Natural products 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、大豆胚軸よりのサポニ
ンの製造法に関する。TECHNICAL FIELD The present invention relates to a method for producing saponin from soybean hypocotyl.
【０００２】0002
【従来の技術】マメ科植物の大豆に含有されているサポ
ニンは、乳化作用や薬理作用など様々な効果を有するこ
とが知られている。このような作用を有する大豆含有サ
ポニンは、従来より様々な方法で回収されてきた。例え
ば、まずサポニンを回収するための原料として大豆の種
子を用い、これを粉砕した後ｎ−ヘキサンなどの非極性
溶媒で脂質成分を除去する。次に脱脂された粉砕大豆種
子をメチルアルコールなどの含水低級アルコールで抽出
する。得られた抽出液は減圧下で濃縮し、ｎ−ブタノー
ルと水で分配する。この分配によって、糖成分は水画分
に残り、サポニンはｎ−ブタノール画分に移行するため
、このｎ−ブタノール画分を濃縮・固化して粗サポニン
を得る方法などがある。BACKGROUND OF THE INVENTION Saponin contained in soybean, a legume, is known to have various effects such as emulsifying and pharmacological effects. Soybean-containing saponins having such effects have been recovered by various methods. For example, first, soybean seeds are used as a raw material for recovering saponin, and after pulverizing the seeds, lipid components are removed using a nonpolar solvent such as n-hexane. Next, the defatted crushed soybean seeds are extracted with a hydrous lower alcohol such as methyl alcohol. The resulting extract is concentrated under reduced pressure and partitioned between n-butanol and water. Due to this distribution, the sugar component remains in the water fraction and the saponin moves to the n-butanol fraction, so there is a method of concentrating and solidifying this n-butanol fraction to obtain crude saponin.
【０００３】しかしながら、上記方法によると原料の大
豆種子を多量に使用するにも拘らず、収量が低いため生
産コストが高くなるという問題点がある。また、ｎ−ヘ
キサンで直接原料の大豆種子の脂質成分を除去している
ため、ｎ−ヘキサンが大豆種子に十分に行き渡らなけれ
ば完全に脂質成分が除去できない。そのため、大豆種子
を十分に粉砕したうえで操作を数回繰り返し行わなけれ
ばならず、操作の繁雑化を招いている。さらに、ｎ−ブ
タノ−ルと水で分配する脱糖工程において、水溶性であ
るサポニンは、分配後の水画分にかなりの量残存してし
まい、収量低下の原因の一つとなっている。However, the above method has the problem that although a large amount of soybean seeds are used as a raw material, the yield is low and the production cost is high. Furthermore, since the lipid components of the soybean seeds, which are raw materials, are directly removed using n-hexane, the lipid components cannot be completely removed unless n-hexane is sufficiently distributed in the soybean seeds. Therefore, the soybean seeds must be sufficiently crushed and the operation must be repeated several times, leading to complicated operations. Furthermore, in the desugarization process in which n-butanol and water are distributed, a considerable amount of water-soluble saponin remains in the water fraction after distribution, which is one of the causes of reduced yield.
【０００４】上記方法のように従来技術における大豆よ
りのサポニンの製造方法は、全般的に脂質成分除去効率
が悪いため、その操作が繁雑であり、生産性が低下して
いた。また、糖成分除去工程におけるサポニンの損失量
が多いため、サポニンの回収率が悪く、生産コストが上
昇していた。[0004] Conventional methods for producing saponin from soybeans, such as the above method, generally have low lipid component removal efficiency, resulting in complicated operations and reduced productivity. In addition, since a large amount of saponin is lost in the sugar component removal process, the recovery rate of saponin is poor and production costs are increased.
【０００５】[0005]
【発明が解決しようとする課題】本発明は上述の従来技
術の問題点を解決し、脂質成分除去操作を簡易化し、さ
らに糖成分除去工程におけるサポニンの損失量を減少さ
せることによって、サポニン回収率を増加させると共に
生産性を向上させることを目的としている。[Problems to be Solved by the Invention] The present invention solves the problems of the prior art described above, simplifies the lipid component removal operation, and further reduces the amount of saponin loss in the sugar component removal process, thereby increasing the saponin recovery rate. The purpose is to increase productivity and improve productivity.
【０００６】[0006]
【課題を解決するための手段】本発明者等は上述従来の
技術の問題点を解決するため鋭意研究したところ、大豆
胚軸を原料とし、これを抽出した抽出液をｉ−アミルア
ルコールと水で分配し、脂質成分をｉ−アミルアルコー
ル画分に移行させて除去し、残った水画分を酸性とした
後、この画分をｎ−ブタノールと水で分配し、糖成分以
外をｎ−ブタノール画分に移行させ、この画分からサポ
ニンを回収することにより高収率でサポニンが得られる
ことを見い出し本発明を提供することができた。[Means for Solving the Problems] In order to solve the problems of the above-mentioned conventional technology, the present inventors conducted intensive research and found that soybean hypocotyl was used as a raw material, and the extract obtained from the hypocotyl was mixed with i-amyl alcohol and water. After removing the lipid components by transferring them to the i-amyl alcohol fraction and making the remaining water fraction acidic, this fraction is distributed between n-butanol and water to remove the lipid components from the n-amyl alcohol fraction. It was discovered that saponin can be obtained in high yield by transferring saponin to a butanol fraction and recovering saponin from this fraction, thereby providing the present invention.
【０００７】すなわち本発明は、マメ科植物の大豆に含
有されているサポニンを抽出分離により回収する方法で
あって、サポニンを回収するための原料として大豆胚軸
を用い、これを６０〜８０％の含水低級アルコールで抽
出してサポニン成分を分離し、得られた抽出液を濃縮し
た後、水とサポニン不溶性の有機溶媒で分配し、抽出液
中の脂質成分を有機溶媒画分へ移行させて除去し、残っ
た水画分を酸性としてサポニンの水溶性を低下させた後
、適当なアルコールで該水画分をさらに分配し、糖成分
以外をアルコール画分へ移行させ、この画分からサポニ
ンを回収することを特徴とする大豆胚軸よりのサポニン
の製造法である。That is, the present invention is a method for recovering saponins contained in soybeans, which are leguminous plants, by extraction and separation. After extracting with water-containing lower alcohol to separate saponin components and concentrating the obtained extract, partitioning between water and an organic solvent in which saponin is insoluble, the lipid components in the extract are transferred to the organic solvent fraction. After removing the water fraction and acidifying the remaining water fraction to reduce the water solubility of saponin, the water fraction is further partitioned with an appropriate alcohol to transfer components other than sugar components to the alcohol fraction, and saponin is extracted from this fraction. This is a method for producing saponin from soybean hypocotyl, which is characterized in that it is recovered.
【０００８】なお、上記アルコール画分からのサポニン
の回収法は、該画分を減圧下で濃縮および乾固すること
によって粗サポニンを得ることができる。この粗サポニ
ンは、真空乾燥することにより黄白色のサポニン粉末を
得ることができ、脱色したサポニン粉末を得たい場合は
、粗サポニンをメタノールに溶かし、活性炭カラムに通
した後、濃縮および乾固することにより白色のサポニン
を得ることができる。[0008] In the method for recovering saponin from the alcohol fraction, crude saponin can be obtained by concentrating and drying the fraction under reduced pressure. This crude saponin can be vacuum-dried to obtain yellow-white saponin powder. If you want to obtain decolorized saponin powder, dissolve the crude saponin in methanol, pass it through an activated carbon column, and then concentrate and dry it. By doing this, white saponin can be obtained.
【０００９】本発明において脂質成分を除去する工程で
用いられる有機溶媒は、脂質成分が良好に移行され得る
ものであれば特に制限はないが、炭素数が５以上のアル
コールが良く、例えばｉ−アミルアルコールなどが好適
である。アルコールは、脂質成分を良好に移行し得るも
のであっても高価なものは生産コストの上昇を招き好ま
しくない。The organic solvent used in the step of removing lipid components in the present invention is not particularly limited as long as the lipid components can be transferred well, but alcohols having 5 or more carbon atoms are preferable, such as i- Amyl alcohol and the like are suitable. Even if the alcohol can transfer lipid components well, an expensive alcohol is not preferable because it increases the production cost.
【００１０】本発明において糖成分を除去する工程で用
いられるアルコールは、安価でありかつサポニンを良好
に移行し得るものであれば特に制限はなく、例えばｎ−
ブチルアルコールなどを用いると良い。[0010] The alcohol used in the step of removing sugar components in the present invention is not particularly limited as long as it is inexpensive and can transfer saponin well; for example, n-
It is best to use butyl alcohol, etc.
【００１１】本発明において、脂質成分除去後に得られ
る水画分は、サポニン分子中のカルボキシル基の解離を
抑制してサポニンの水溶性を低下させるために、酸また
は酸性塩を加えて酸性に調整している。また、溶液のｐ
Ｈは４から４．５に調整すると良い。なお、ｐＨを調整
するために用いる酸または酸性塩は、サポニンの性質が
損なわれるものでなければ特に制限はなく、例えば酢酸
などが好ましい。[0011] In the present invention, the water fraction obtained after the removal of lipid components is adjusted to be acidic by adding an acid or an acidic salt in order to suppress the dissociation of carboxyl groups in saponin molecules and reduce the water solubility of saponin. are doing. Also, p of the solution
It is best to adjust H from 4 to 4.5. The acid or acidic salt used to adjust the pH is not particularly limited as long as it does not impair the properties of saponin, and for example, acetic acid is preferred.
【００１２】0012
【作用】本発明の方法によると、原料に含まれている脂
質成分は、原料からサポニン成分を抽出した抽出液を脱
脂用溶媒を用いて分配することにより、脂質成分を移行
させて除去している。そのため、脱脂用溶媒が各種成分
に良く行き渡り効率良く脱脂することができ、原料に直
接ｎ−ヘキサンのような非極性溶媒を通して脱脂した場
合と比べて除去効率が著しく向上し操作が簡略になる。
また、脱糖工程においてサポニン成分が含まれる水画分
をアルコールで分配する際、事前に該水画分を酸性にし
てサポニンの水溶性を低下させているため、サポニンは
水画分に残存せずに完全にアルコール画分へ移行するよ
うになる。そのため、サポニンが糖成分と共に水画分に
残存して除去されるということがなくなり、しかもサポ
ニン含有率の高い大豆の胚軸を原料としているため、サ
ポニンの回収率が著しく向上する。[Operation] According to the method of the present invention, the lipid components contained in the raw materials are removed by transferring the lipid components by distributing the extract obtained by extracting the saponin components from the raw materials using a degreasing solvent. There is. Therefore, the degreasing solvent can spread well to various components and can be efficiently degreased, and the removal efficiency is significantly improved and the operation is simpler than when degreasing is carried out by passing a nonpolar solvent such as n-hexane directly over the raw material. In addition, when distributing the water fraction containing saponin components with alcohol in the desaccharification process, the water fraction is made acidic in advance to reduce the water solubility of saponin, so saponin does not remain in the water fraction. The alcohol fraction completely migrates to the alcohol fraction. Therefore, saponin does not remain in the water fraction with sugar components and is not removed, and since soybean hypocotyl, which has a high saponin content, is used as a raw material, the recovery rate of saponin is significantly improved.
【００１３】以下、実施例により本発明をさらに詳細に
説明する。しかし本発明の範囲は以下の実施例により制
限されるものではない。[0013] The present invention will now be explained in more detail with reference to Examples. However, the scope of the present invention is not limited by the following examples.
【００１４】[0014]
【実施例】本実施例では、まずマメ科植物の大豆の胚軸
９．２ｋｇを市販のミキサーで粉砕したものをステンレ
スタンクに入れ、そこに７０％エタノールを４５リット
ル加えて良く振り混ぜ、３０℃で２４時間抽出した。抽
出後、得られた抽出液をブフナー漏斗で濾過し、その濾
液をロータリーエバポレーターを用いて減圧下で濃縮し
て３４００ｇのエキスを得た。このエキスに５リットル
の水を加えて良く振り混ぜ、水懸濁液としたものを分液
漏斗に移し、そこに５リットルのｉ−アミルアルコール
を加え、良く振った後一晩静置して水画分とｉ−アミル
アルコール画分とに分配した。分配後、脂質成分が移行
したｉ−アミルアルコール画分を除去し、得られた水画
分をもう一度同様に分配し、ｉ−アミルアルコール画分
を除去して脱脂された水画分を得た。[Example] In this example, first, 9.2 kg of soybean hypocotyl, a legume, was crushed using a commercially available mixer, placed in a stainless steel tank, and 45 liters of 70% ethanol was added thereto, shaken well, and mixed for 30 minutes. Extraction was carried out for 24 hours at °C. After extraction, the resulting extract was filtered using a Buchner funnel, and the filtrate was concentrated under reduced pressure using a rotary evaporator to obtain 3400 g of extract. Add 5 liters of water to this extract, mix well, make a water suspension, transfer it to a separatory funnel, add 5 liters of i-amyl alcohol there, shake well, and let it stand overnight. It was partitioned into a water fraction and an i-amyl alcohol fraction. After distribution, the i-amyl alcohol fraction to which lipid components had been transferred was removed, and the resulting water fraction was distributed in the same manner once again, and the i-amyl alcohol fraction was removed to obtain a defatted water fraction. .
【００１５】次に、得られた水画分にリン酸二水素ナト
リウムを加え、その溶液のｐＨを約４．５に調整した。
ｐＨ調整した水画分は、分液漏斗に移してｎ−ブチルア
ルコールを加え、良く振った後一晩静置して水画分とｎ
−ブチルアルコール画分に分配した。分配後、糖分が残
存した水画分を除去し、サポニンが移行したｎ−ブチル
アルコール画分に、リン酸二水素ナトリウム水溶液を加
えてもう一度分配し、水画分を除去して脱糖されたｎ−
ブチルアルコール画分を得た。得られたｎ−ブチルアル
コール画分をロータリーエバポレーターを用いて減圧下
で濃縮し、その濃縮液をブフナー漏斗で濾過した後真空
乾燥および凍結乾燥を行い、約４６０ｇの粗サポニンを
得た。Next, sodium dihydrogen phosphate was added to the obtained water fraction to adjust the pH of the solution to about 4.5. The pH-adjusted water fraction was transferred to a separatory funnel, n-butyl alcohol was added, shaken well, and left overnight to separate the water fraction and n-butyl alcohol.
- butyl alcohol fraction. After distribution, the water fraction in which sugar remained was removed, and the n-butyl alcohol fraction to which saponin had been transferred was added with an aqueous sodium dihydrogen phosphate solution and distributed again to remove the water fraction and desugarized. n-
A butyl alcohol fraction was obtained. The obtained n-butyl alcohol fraction was concentrated under reduced pressure using a rotary evaporator, and the concentrated liquid was filtered using a Buchner funnel, and then vacuum-dried and freeze-dried to obtain about 460 g of crude saponin.
【００１６】[0016]
【発明の効果】本発明の開発により、原料に含まれる脂
質成分の除去効率が向上し、その操作が簡略化したため
生産性が向上した。また、サポニン含有率の高い大豆胚
軸を用い、かつ糖成分除去工程におけるサポニンの損失
が防止されたため、サポニンの回収率が上昇し、生産コ
ストが低下した。[Effects of the Invention] The development of the present invention has improved the efficiency of removing lipid components contained in raw materials and simplified the operation, resulting in improved productivity. Furthermore, because soybean hypocotyl with a high saponin content was used and loss of saponin in the sugar component removal process was prevented, the recovery rate of saponin increased and production costs decreased.
Claims (1)
ポニンを抽出分離により回収する方法であって、サポニ
ンを回収するための原料として大豆胚軸を用い、これを
６０〜８０％の含水低級アルコールで抽出してサポニン
成分を分離し、得られた抽出液を濃縮した後、水とサポ
ニン不溶性の有機溶媒で分配し、抽出液中の脂質成分を
有機溶媒画分へ移行させて除去し、残った水画分を酸性
としてサポニンの水溶性を低下させた後、適当なアルコ
ールで該水画分をさらに分配し、糖成分以外をアルコー
ル画分へ移行させ、この画分からサポニンを回収するこ
とを特徴とする大豆胚軸よりのサポニンの製造法。Claim 1: A method for recovering saponin contained in soybean, a legume, by extraction and separation, using soybean hypocotyl as a raw material for recovering saponin, After extracting with alcohol to separate saponin components and concentrating the obtained extract, partitioning between water and a saponin-insoluble organic solvent, the lipid components in the extract are transferred to the organic solvent fraction and removed. After reducing the water solubility of saponin by acidifying the remaining water fraction, the water fraction is further distributed with an appropriate alcohol, components other than sugar components are transferred to the alcohol fraction, and saponin is recovered from this fraction. A method for producing saponin from soybean hypocotyl, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2412328A JPH04217629A (en) | 1990-12-19 | 1990-12-19 | Production of saponin form hypocotyl of soybean |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2412328A JPH04217629A (en) | 1990-12-19 | 1990-12-19 | Production of saponin form hypocotyl of soybean |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04217629A true JPH04217629A (en) | 1992-08-07 |
Family
ID=18521180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2412328A Pending JPH04217629A (en) | 1990-12-19 | 1990-12-19 | Production of saponin form hypocotyl of soybean |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04217629A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2003027049A1 (en) * | 2001-09-20 | 2003-04-03 | Ezaki Glico Co., Ltd. | Method of extracting and method of purifying an effective substance |
| JP2011225586A (en) * | 2003-07-02 | 2011-11-10 | Fuji Oil Co Ltd | Flavonoid solubilizing agent and method of solubilizing flavonoid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5664000A (en) * | 1979-10-29 | 1981-05-30 | Osaka Chem Lab | Novel saponin substance |
| JPS5872523A (en) * | 1981-10-26 | 1983-04-30 | Osaka Chem Lab | Antitumor agent |
| 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 |
-
1990
- 1990-12-19 JP JP2412328A patent/JPH04217629A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5664000A (en) * | 1979-10-29 | 1981-05-30 | Osaka Chem Lab | Novel saponin substance |
| JPS5872523A (en) * | 1981-10-26 | 1983-04-30 | Osaka Chem Lab | Antitumor agent |
| 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 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2003027049A1 (en) * | 2001-09-20 | 2003-04-03 | Ezaki Glico Co., Ltd. | Method of extracting and method of purifying an effective substance |
| US7282150B2 (en) | 2001-09-20 | 2007-10-16 | Ezaki Glico Co., Ltd. | Method of extracting and method of purifying an effective substance |
| JP2011225586A (en) * | 2003-07-02 | 2011-11-10 | Fuji Oil Co Ltd | Flavonoid solubilizing agent and method of solubilizing flavonoid |
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