JPH0645634B2 - Soy isoflavone glycoside - Google Patents
Soy isoflavone glycosideInfo
- Publication number
- JPH0645634B2 JPH0645634B2 JP4897891A JP4897891A JPH0645634B2 JP H0645634 B2 JPH0645634 B2 JP H0645634B2 JP 4897891 A JP4897891 A JP 4897891A JP 4897891 A JP4897891 A JP 4897891A JP H0645634 B2 JPH0645634 B2 JP H0645634B2
- Authority
- JP
- Japan
- Prior art keywords
- isoflavone
- soybean
- component
- isolated
- hypocotyl
- 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
- ZWSNUPOSLDAWJS-QNDFHXLGSA-N 6,7-dihydroxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one Chemical compound OC[C@H]1O[C@@H](Oc2ccc(cc2)-c2coc3cc(O)c(O)cc3c2=O)[C@H](O)[C@@H](O)[C@@H]1O ZWSNUPOSLDAWJS-QNDFHXLGSA-N 0.000 title claims description 6
- 235000003687 soy isoflavones Nutrition 0.000 title claims description 3
- 235000010469 Glycine max Nutrition 0.000 description 31
- 244000068988 Glycine max Species 0.000 description 31
- 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 description 28
- 235000008696 isoflavones Nutrition 0.000 description 28
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 25
- OZBAVEKZGSOMOJ-MIUGBVLSSA-N glycitin Chemical compound COC1=CC(C(C(C=2C=CC(O)=CC=2)=CO2)=O)=C2C=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OZBAVEKZGSOMOJ-MIUGBVLSSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XJTZHGNBKZYODI-UHFFFAOYSA-N Glycitin Natural products OCC1OC(Oc2ccc3OC=C(C(=O)c3c2CO)c4ccc(O)cc4)C(O)C(O)C1O XJTZHGNBKZYODI-UHFFFAOYSA-N 0.000 description 7
- 238000002955 isolation Methods 0.000 description 7
- 229930182470 glycoside Natural products 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000002338 glycosides Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N Daidzein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 3
- GMTUGPYJRUMVTC-UHFFFAOYSA-N Daidzin Natural products OC(COc1ccc2C(=O)C(=COc2c1)c3ccc(O)cc3)C(O)C(O)C(O)C=O GMTUGPYJRUMVTC-UHFFFAOYSA-N 0.000 description 3
- KYQZWONCHDNPDP-UHFFFAOYSA-N Daidzoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-UHFFFAOYSA-N 0.000 description 3
- ZCOLJUOHXJRHDI-FZHKGVQDSA-N Genistein 7-O-glucoside Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)c1cc(O)c2C(=O)C(c3ccc(O)cc3)=COc2c1 ZCOLJUOHXJRHDI-FZHKGVQDSA-N 0.000 description 3
- CJPNHKPXZYYCME-UHFFFAOYSA-N Genistin Natural products OCC1OC(Oc2ccc(O)c3OC(=CC(=O)c23)c4ccc(O)cc4)C(O)C(O)C1O CJPNHKPXZYYCME-UHFFFAOYSA-N 0.000 description 3
- YCUNGEJJOMKCGZ-UHFFFAOYSA-N Pallidiflorin Natural products C1=CC(OC)=CC=C1C1=COC2=CC=CC(O)=C2C1=O YCUNGEJJOMKCGZ-UHFFFAOYSA-N 0.000 description 3
- KYQZWONCHDNPDP-QNDFHXLGSA-N daidzein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-QNDFHXLGSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- DXWGBJJLEDQBKS-UHFFFAOYSA-N acetylgenistin Natural products OC1C(O)C(O)C(COC(=O)C)OC1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 DXWGBJJLEDQBKS-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- -1 isoflavone glycosides Chemical class 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DXWGBJJLEDQBKS-LDBVRRDLSA-N [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl acetate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)C)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 DXWGBJJLEDQBKS-LDBVRRDLSA-N 0.000 description 1
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 150000002515 isoflavone derivatives Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000020985 whole grains Nutrition 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、大豆から単離した大豆
イソフラボン配糖体に関する。TECHNICAL FIELD The present invention relates to a soybean isoflavone glycoside isolated from soybean.
【０００２】[0002]
【従来の技術】従来、大豆イソフラボン配糖体として、
ダイジン、グリシチン、ゲニスチン、６”−Ｏ−アセチ
ルダイジンおよび６”−Ｏ−アセチルゲニスチンの５種
類が報告されている。Conventionally, as a soybean isoflavone glycoside,
Five types of daidzin, glycitin, genistin, 6 ″ -O-acetyldaididine and 6 ″ -O-acetylgenistin have been reported.
【０００３】大豆イソフラボン配糖体の単離の例として
は、ナイム(Naim)らは、全粒大豆粉から、ダイジン、グ
リシチンおよびゲニスチンを単離した例(Phytochemistr
y 1973年 169〜170 頁参照) がある。As an example of the isolation of soybean isoflavone glycosides, Naim et al. (Phytochemistr) have isolated daidzin, glycitin and genistin from whole soybean flour.
y 1973, pp. 169-170).
【０００４】これに対し、太田らは、脱脂大豆から、ダ
イジン、ゲニスチン、6"-0- アセチルダイジンおよび6"
-0- アセチルゲニスチンを単離したが、グリシチンの存
在を確認することができなかったと報告している(Agri
c.Biol.Chem. 1980年 469〜470 頁およびAgric.Biol. C
hem. 1979年1415〜1419頁参照) 。On the other hand, Ota et al., From defatted soybean, daidzin, genistin, 6 "-0-acetyldaidzine and 6"
-0- Acetylgenistin was isolated, but reported that the presence of glycitin could not be confirmed (Agri
c. Biol. Chem. 1980 pp. 469-470 and Agric. Biol. C.
hem. 1979, pp. 1415-1419).
【０００５】また、ファーマカリデス(Farmakidis)も焙
煎した脱脂大豆フレークから、イソフラボン成分を単離
し、太田らと同じくグリシチンを確認できなかったと報
告している(J.Agric.Food Chem,1985 年385 〜389 頁参
照) 。[0005] Farmakidis also reported that isoflavone components were isolated from roasted defatted soybean flakes and that glycitin could not be confirmed as in Ota et al. (J. Agric. Food Chem, 1985). (See pages 385-389).
【０００６】[0006]
【発明が解決しようとする課題】大豆から単離した大豆
イソフラボン成分は、抗酸化、エストロゲン、抗菌、抗
癌等の生理作用が報告されていることで、食品中の機能
性成分としても注目されてきているが、従来の大豆から
単離したイソフラボン成分は、コストを無視して単離し
ているもので、工業的に得るのにはコスト的に問題があ
る。The soybean isoflavone component isolated from soybean has been reported to have physiological effects such as antioxidant, estrogen, antibacterial, and anticancer, and thus has attracted attention as a functional component in foods. However, conventional isoflavone components isolated from soybeans are isolated by ignoring the cost, and there is a cost problem in obtaining them industrially.
【０００７】本発明は、この問題を解決するためになさ
れたものであって、この食品中の機能性成分として注目
されている大豆イソフラボン成分を、工業的に採算のあ
うものとして、単離することが、可能となる新たな手段
を提供することを目的とする。The present invention has been made in order to solve this problem, and isolates the soybean isoflavone component, which is attracting attention as a functional component in this food, as an industrially profitable product. The purpose is to provide a new means that is possible.
【０００８】[0008]
【課題を解決するための手段】本発明は、上述の目的の
ために種々の研究を重ねて得られた知見に基いて完成し
たものである。The present invention has been completed based on the findings obtained through various studies for the above purpose.
【０００９】従来の大豆イソフラボン成分の単離が、５
種類あるとされている大豆イソフラボン配糖体のうち
で、グリシチンについてはなされていないことから、ま
ず、このグリシチン成分についての研究を行なった。The conventional isolation of soy isoflavone components is 5
Of the soybean isoflavone glycosides that are considered to be varieties, glycitin has not been studied, so we first studied this glycitin component.
【００１０】大豆を種皮、子葉および胚軸に分け、部位
別のイソフラボン成分含量を測定した結果Soybean was divided into seed coat, cotyledon and hypocotyl, and the isoflavone component content was measured for each site.
【表１】 にあるように、グリシチンは、胚軸にのみ高濃度で存在
することを明らかにすることができた。さらに、数品種
のイソフラボン成分含量を測定した結果、胚軸の総イソ
フラボン成分濃度は、子葉の20〜60倍高濃度であり、大
豆のイソフラボン成分の30〜50% が全粒大豆重量の2 〜
3%にすぎない胚軸に極在していることも分かった。ま
た、胚軸からは、既知イソフラボン成分とは、明らかに
異なる成分が検出され、この成分は、その特性から推測
して文献末記載の新規なイソフラボン物質であると判断
された。[Table 1] As shown in, it was possible to reveal that glycitin is only present in the hypocotyl at high concentration. Furthermore, as a result of measuring the isoflavone component content of several cultivars, the total isoflavone component concentration of hypocotyl was 20 to 60 times higher than that of cotyledon, and 30 to 50% of the isoflavone component of soybean was 2 to 60% of the total soybean weight.
It was also found to be localized in the hypocotyl, which accounts for only 3%. In addition, a component that was clearly different from the known isoflavone component was detected in the hypocotyl, and this component was judged to be a novel isoflavone substance described in the end of the literature by inferring from its characteristics.
【００１１】そして、この新規なイソフラボン成分の単
離、精製を研究したところ、大豆胚軸を出発原料として
用い、次のような方法で単離、精製をすることができ
た。Studies on the isolation and purification of this novel isoflavone component have revealed that the soybean hypocotyl can be used as a starting material and isolated and purified by the following method.
【００１２】即ち、大豆胚軸から含水エタノールにより
大豆配糖体成分を抽出し、抽出液を濃縮・乾固した抽出
エキスを得た。That is, a soybean glycoside component was extracted from soybean hypocotyl with hydrous ethanol, and the extract was concentrated and dried to obtain an extract.
【００１３】このエキスを水に分散後、ブタノールを添
加し、ブタノール層にイソフラボン成分を抽出すること
により大豆オリゴ糖を除去した。This extract was dispersed in water, butanol was added, and the isoflavone component was extracted into the butanol layer to remove the soybean oligosaccharide.
【００１４】このブタノール層を濃縮・乾固後、メタノ
ールに溶解し、セファデックスＬＨ−２０によるゲル瀘
過で粗イソラボン画分を得た。This butanol layer was concentrated and dried to dryness, then dissolved in methanol, and subjected to gel filtration with Sephadex LH-20 to obtain a crude isolavone fraction.
【００１５】この粗イソラボン画分を高速液体クロマト
グラフィー（ＨＰＬＣ）で処理することにより、２種類
の新規なイソフラボン物質を単離することができた。た
だし、上記の単離法は一例であって、類似の性質を示す
溶媒ないし溶媒系の使用や、その他の条件の変更も可能
である。By treating this crude isolavone fraction with high performance liquid chromatography (HPLC), two novel isoflavone substances could be isolated. However, the above isolation method is an example, and it is possible to use a solvent or a solvent system having similar properties and change other conditions.
【００１６】単離したイソフラボン物質を、核磁気共鳴
スペクトル等の機器分析で検討した結果、新規なイソフ
ラボン物質であることを確認し、その構造を決定するこ
とができた。即ち、この単離したイソフラボン物質は、As a result of examining the isolated isoflavone substance by instrumental analysis such as nuclear magnetic resonance spectrum, it was confirmed that it was a novel isoflavone substance, and its structure could be determined. That is, the isolated isoflavone material is
【化１】 に示している如く、グリシテイン−７−Ｏ−β−（６”
−Ｏ−アセチル）−Ｄ−グルコピラノサイドおよびグリ
シチイン−７−Ｏ−β−（６”−Ｏ−マロニル）−Ｄ−
グルコピラノサイドと記すことのできる化学構造を持つ
新規なイソフラボン物質である。[Chemical 1] As shown in, glycitein-7-O-β- (6 "
-O-acetyl) -D-glucopyranoside and glyciciin-7-O-β- (6 "-O-malonyl) -D-
It is a novel isoflavone substance with a chemical structure that can be described as glucopyranoside.
【００１７】そして、この新規なイソフラボン物質は、
大豆の総イソフラボン成分の３０〜５０％が極在してい
て、全粒大豆重量の２〜３％にすぎない胚軸を出発原料
として、単離し精製して得られるものであるから、従来
手段で得られる大豆イソフラボン成分に比して遥かに単
離精製のコストが低減できて単離・精製の工業化を可能
とするものである。This novel isoflavone substance is
30 to 50% of the total isoflavone component of soybean is extremely present, and is obtained by isolation and purification using hypocotyl as a starting material, which is only 2 to 3% of the weight of whole soybean. Compared with the soybean isoflavone component obtained in 1., the cost of isolation and purification can be reduced significantly, and the isolation and purification can be industrialized.
【００１８】それ故、本発明においては、前述の目的を
達成するための手段として、この大豆胚軸から抽出され
る上記化学構造を持つ新規な大豆イソフラボン配糖体を
提起するものである。Therefore, the present invention proposes a novel soybean isoflavone glycoside having the above-mentioned chemical structure extracted from this soybean hypocotyl as a means for achieving the above-mentioned object.
【００１９】[0019]
【実施例】次に実施例を詳述する。大豆胚軸を粉砕後、
５倍量の７０％含水エタノールで３回抽出し、この抽出
液をロータリーエバポレーターで減圧乾固した。EXAMPLES Next, examples will be described in detail. After crushing the soybean hypocotyl,
It was extracted 3 times with 5 volumes of 70% hydrous ethanol, and this extract was dried under reduced pressure with a rotary evaporator.
【００２０】この減圧乾固物にブタノールと水を各１リ
ットル添加し、充分に溶解後、分液ロートに入れ、激し
く撹拌することにより大豆配糖体成分を抽出した。To this dried product under reduced pressure, 1 liter of butanol and 1 liter of water were added, and after sufficiently dissolving, the mixture was placed in a separating funnel and vigorously stirred to extract the soybean glycoside component.
【００２１】一晩静置後、ブタノール層をロータリーエ
バポレーターで、濃縮・乾固し、粗大豆配糖体画分を得
た。After allowing to stand overnight, the butanol layer was concentrated and dried by a rotary evaporator to obtain a crude soybean glycoside fraction.
【００２２】この粗大豆配糖体画分をメタノールに溶か
してセファデックスＬＨ−２０カラム(5×74cm) に供
し、100%メタノールで溶出した。溶出画分を薄層クロマ
トグラフィーおよび高速液体クロマトグラフィーで分析
し、各溶出成分の同定を行なった。新規イソフラボンの
溶出画分を集めて濃縮・乾固し、逆相系カラムを用いた
液体クロマトグラフィーで処理することになって、新規
イソフラボン物質I とIIをそれぞれ単離した。This crude soybean glycoside fraction was dissolved in methanol and applied to a Sephadex LH-20 column (5 × 74 cm) and eluted with 100% methanol. The eluted fractions were analyzed by thin layer chromatography and high performance liquid chromatography to identify each eluted component. The elution fractions of the novel isoflavones were collected, concentrated and dried, and then subjected to liquid chromatography using a reversed-phase column to isolate novel isoflavone substances I and II, respectively.
【００２３】単離したイソフラボン成分 IとIIのスペク
トルデータは、The spectral data of the isolated isoflavone components I and II are
【表２】 ・[Table 2] ・
【表３】 ・[Table 3] ・
【表４】 の通りであった。[Table 4] It was the street.
【００２４】これらの結果から、イソフラボン物質 Iを
グリシテイン−７−Ｏ−β−（６”−Ｏ−マロニル）−
Ｄ−グルコピラノサイド、イソフラボン物質IIをグリシ
テイン−７−Ｏ−β−（６”−Ｏ−アセチル）−Ｄ−グ
ルコピラノサイドであると決定した。From these results, isoflavone substance I was identified as glycitein-7-O-β- (6 "-O-malonyl)-
D-glucopyranoside, isoflavone substance II was determined to be glycitein-7-O-β- (6 "-O-acetyl) -D-glucopyranoside.
【００２５】[0025]
【発明の効果】以上説明したように、本発明による大豆
イソフラボン配糖体は、大豆の総イソフラボン成分の３
０〜５０％が極在していて、全粒大豆重量の２〜３％に
すぎない胚軸を、出発原料として、単離し精製して得ら
れるものであるから、単離・精製の工業化が、コストに
おいて充分に可能なものとなる。As described above, the soybean isoflavone glycoside according to the present invention comprises 3 of the total isoflavone components of soybean.
It is obtained by isolating and purifying the hypocotyl, which has 0 to 50% as a starting material and is only 2 to 3% of the weight of the whole grain soybean. That is, it is possible in terms of cost.
Claims (1)
−アセチル）−Ｄ−グルコピラノサイドおよびグリシテ
イン−７−Ｏ−β−（６”−Ｏ−マロニル）−Ｄ−グル
コピラノサイドからなる大豆イソフラボン配糖体。1. Glycitein-7-O-β- (6 "-O
A soy isoflavone glycoside consisting of -acetyl) -D-glucopyranoside and glycitein-7-O-β- (6 "-O-malonyl) -D-glucopyranoside.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4897891A JPH0645634B2 (en) | 1991-02-21 | 1991-02-21 | Soy isoflavone glycoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4897891A JPH0645634B2 (en) | 1991-02-21 | 1991-02-21 | Soy isoflavone glycoside |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04266898A JPH04266898A (en) | 1992-09-22 |
| JPH0645634B2 true JPH0645634B2 (en) | 1994-06-15 |
Family
ID=12818345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4897891A Expired - Fee Related JPH0645634B2 (en) | 1991-02-21 | 1991-02-21 | Soy isoflavone glycoside |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0645634B2 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5821361A (en) | 1996-06-11 | 1998-10-13 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6521282B1 (en) | 1996-08-09 | 2003-02-18 | Protein Technologies International, Inc. | Aglucone isoflavone enriched vegetable flour and grit |
| US6579561B2 (en) | 1996-08-09 | 2003-06-17 | Protein Technologies International, Inc. | Aglucone isoflavone enriched vegetable flour and vegetable grit and process for making the same from a vegetable material containing isoflavone |
| US6132795A (en) * | 1998-03-15 | 2000-10-17 | Protein Technologies International, Inc. | Vegetable protein composition containing an isoflavone depleted vegetable protein material with an isoflavone containing material |
| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6703051B1 (en) | 1998-10-13 | 2004-03-09 | Solae, Llc | Process for separating and recovering protein and isoflavones from a plant material |
| US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
| US7285297B1 (en) | 1999-04-23 | 2007-10-23 | Archer-Daniels-Midland Company | Method of reducing low density liproprotein cholesterol concentration |
| JP4475947B2 (en) | 2001-07-24 | 2010-06-09 | カーギル インコーポレイテッド | Method for isolating phenolic compounds |
| EP1576893A4 (en) * | 2002-12-24 | 2006-01-04 | Fuji Oil Co Ltd | Composition containing isoflavone of high purity at high concentration and process for producing the same |
| JP2006069898A (en) * | 2004-08-31 | 2006-03-16 | Fuji Oil Co Ltd | Composition for ameliorating renal function |
-
1991
- 1991-02-21 JP JP4897891A patent/JPH0645634B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04266898A (en) | 1992-09-22 |
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