JPH0421670B2 - - Google Patents
Info
- Publication number
- JPH0421670B2 JPH0421670B2 JP60266125A JP26612585A JPH0421670B2 JP H0421670 B2 JPH0421670 B2 JP H0421670B2 JP 60266125 A JP60266125 A JP 60266125A JP 26612585 A JP26612585 A JP 26612585A JP H0421670 B2 JPH0421670 B2 JP H0421670B2
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- organic solvent
- isoflavone
- water
- resin
- 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
- 229930012930 isoflavone derivative Natural products 0.000 claims description 20
- 150000002515 isoflavone derivatives Chemical class 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- 238000001179 sorption measurement Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 235000020712 soy bean extract Nutrition 0.000 claims description 5
- 229920003002 synthetic resin Polymers 0.000 claims description 5
- 239000000057 synthetic resin Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 235000010469 Glycine max Nutrition 0.000 description 10
- 244000068988 Glycine max Species 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000007240 daidzein Nutrition 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 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 6
- 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 6
- 239000007788 liquid Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 4
- 235000006539 genistein Nutrition 0.000 description 4
- 229940045109 genistein Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000015429 Mirabilis expansa Nutrition 0.000 description 3
- 244000294411 Mirabilis expansa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000013536 miso Nutrition 0.000 description 3
- 239000002952 polymeric resin Substances 0.000 description 3
- 238000000746 purification Methods 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 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YCUNGEJJOMKCGZ-UHFFFAOYSA-N Pallidiflorin Natural products C1=CC(OC)=CC=C1C1=COC2=CC=CC(O)=C2C1=O YCUNGEJJOMKCGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002535 acidifier Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012156 elution solvent Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- RXUWDKBZZLIASQ-UHFFFAOYSA-N Puerarin Natural products OCC1OC(Oc2c(O)cc(O)c3C(=O)C(=COc23)c4ccc(O)cc4)C(O)C(O)C1O RXUWDKBZZLIASQ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- HKEAFJYKMMKDOR-VPRICQMDSA-N puerarin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=CC(C2=O)=C1OC=C2C1=CC=C(O)C=C1 HKEAFJYKMMKDOR-VPRICQMDSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26612585A JPS62126186A (ja) | 1985-11-28 | 1985-11-28 | イソフラボン誘導体含有溶液の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26612585A JPS62126186A (ja) | 1985-11-28 | 1985-11-28 | イソフラボン誘導体含有溶液の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62126186A JPS62126186A (ja) | 1987-06-08 |
| JPH0421670B2 true JPH0421670B2 (de) | 1992-04-13 |
Family
ID=17426672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26612585A Granted JPS62126186A (ja) | 1985-11-28 | 1985-11-28 | イソフラボン誘導体含有溶液の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62126186A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107096514A (zh) * | 2017-06-16 | 2017-08-29 | 江苏科技大学 | 一种中空结构的硼酸基氧化锡印迹复合纳米微球、其制备方法及其应用 |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH679584A5 (de) * | 1989-11-10 | 1992-03-13 | Nestle Sa | |
| NZ252051A (en) | 1992-05-19 | 1996-10-28 | Graham Edmund Kelly | Health supplement comprising a phyto-oestrogen selected from genistein, daidzein, biochanin and/or formononetin |
| US5821361A (en) | 1996-06-11 | 1998-10-13 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| AUPO203996A0 (en) | 1996-08-30 | 1996-09-26 | Novogen Research Pty Ltd | Therapeutic uses |
| US6146668A (en) * | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
| CA2287965C (en) | 1997-05-01 | 2009-10-20 | Graham Edmund Kelly | Treatment or prevention of menopausal symptoms and osteoporosis |
| US6004558A (en) * | 1998-02-25 | 1999-12-21 | Novogen, Inc. | Methods for treating cancer with legume plant extracts |
| 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 |
| AUPP260798A0 (en) | 1998-03-26 | 1998-04-23 | Novogen Research Pty Ltd | Treatment of medical related conditions with isoflavone containing extracts of clover |
| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| JP2000095792A (ja) | 1998-09-21 | 2000-04-04 | Showa Sangyo Co Ltd | ゲニスチンから成るイソフラボン組成物の取得方法 |
| US6703051B1 (en) | 1998-10-13 | 2004-03-09 | Solae, Llc | Process for separating and recovering protein and isoflavones from a plant material |
| US7285297B1 (en) | 1999-04-23 | 2007-10-23 | Archer-Daniels-Midland Company | Method of reducing low density liproprotein cholesterol concentration |
| US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
| AUPQ266199A0 (en) | 1999-09-06 | 1999-09-30 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| JP2001204486A (ja) | 2000-01-28 | 2001-07-31 | Kikkoman Corp | イソフラボンアグリコン含有組成物の製造方法 |
| KR100347668B1 (ko) * | 2000-03-24 | 2002-08-07 | 주식회사 유젠바이오 | 개선된 이소플라본 추출 방법 |
| AUPR363301A0 (en) | 2001-03-08 | 2001-04-05 | Novogen Research Pty Ltd | Dimeric isoflavones |
| JP2002308868A (ja) * | 2001-04-12 | 2002-10-23 | Morita Kk | オルトジヒドロキシ構造を有するイソフラボン化合物の製造方法 |
| JP4403800B2 (ja) * | 2001-06-21 | 2010-01-27 | 不二製油株式会社 | 可溶性イソフラボン含有組成物の製造方法 |
| ATE541569T1 (de) | 2001-07-24 | 2012-02-15 | Cargill Inc | Verfahren zur isolation von phenolischen verbindungen |
| CN100591225C (zh) | 2002-12-24 | 2010-02-24 | 不二制油株式会社 | 含有高浓度的异黄酮并具有高溶解度的组合物及其制备方法 |
| US7713940B2 (en) | 2003-05-20 | 2010-05-11 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Water-soluble isoflavone composition, process for producing the same, and use thereof |
| US20070231411A2 (en) | 2003-09-19 | 2007-10-04 | Sunstar Inc. | Method of inhibiting alveolar bone resorption and periodontal membrane loss and composition for internal use to be used therein |
| CN102206209B (zh) * | 2011-04-12 | 2013-10-30 | 聊城大学 | 从大豆中提取分离大豆异黄酮单体化合物的方法 |
| CN103788156B (zh) * | 2014-02-24 | 2015-07-01 | 聊城大学 | 一种分离纯化大豆异黄酮单体化合物的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5133167A (de) * | 1974-06-05 | 1976-03-22 | Sarubadooru Montagyuto Gy Hose | |
| JPS59187746A (ja) * | 1983-04-11 | 1984-10-24 | Hayashibara Biochem Lab Inc | 飲食物とその製造方法 |
-
1985
- 1985-11-28 JP JP26612585A patent/JPS62126186A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5133167A (de) * | 1974-06-05 | 1976-03-22 | Sarubadooru Montagyuto Gy Hose | |
| JPS59187746A (ja) * | 1983-04-11 | 1984-10-24 | Hayashibara Biochem Lab Inc | 飲食物とその製造方法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107096514A (zh) * | 2017-06-16 | 2017-08-29 | 江苏科技大学 | 一种中空结构的硼酸基氧化锡印迹复合纳米微球、其制备方法及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62126186A (ja) | 1987-06-08 |
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