CN114306421A - Method for preparing isoflavone and saponin in soybean - Google Patents
Method for preparing isoflavone and saponin in soybean Download PDFInfo
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- CN114306421A CN114306421A CN202210128962.XA CN202210128962A CN114306421A CN 114306421 A CN114306421 A CN 114306421A CN 202210128962 A CN202210128962 A CN 202210128962A CN 114306421 A CN114306421 A CN 114306421A
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- soybean
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- saponin
- isoflavone
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- 235000010469 Glycine max Nutrition 0.000 title claims abstract description 66
- 244000068988 Glycine max Species 0.000 title claims abstract description 66
- 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 title claims abstract description 23
- 235000008696 isoflavones Nutrition 0.000 title claims abstract description 23
- 229930182490 saponin Natural products 0.000 title claims abstract description 23
- 150000007949 saponins Chemical class 0.000 title claims abstract description 23
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000001397 quillaja saponaria molina bark Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000243 solution Substances 0.000 claims abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000001035 drying Methods 0.000 claims abstract description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 238000010438 heat treatment Methods 0.000 claims abstract description 16
- 238000010992 reflux Methods 0.000 claims abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 3
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 239000006185 dispersion Substances 0.000 claims abstract description 3
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 7
- 229930187719 Soyasaponin Natural products 0.000 claims description 2
- 235000017709 saponins Nutrition 0.000 claims 3
- 150000002515 isoflavone derivatives Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 235000015895 biscuits Nutrition 0.000 abstract 2
- 239000007788 liquid Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 4
- 230000009471 action Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N Daidzein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 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 2
- 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 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 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 1
- 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 1
- 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 1
- YCUNGEJJOMKCGZ-UHFFFAOYSA-N Pallidiflorin Natural products C1=CC(OC)=CC=C1C1=COC2=CC=CC(O)=C2C1=O YCUNGEJJOMKCGZ-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 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 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000003687 soy isoflavones Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
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- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a preparation method of isoflavone and saponin in soybean, belonging to the technical field of medicine and comprising the following steps: heating and refluxing soybeans for 2 times by using a mixed solution of ethyl acetate and one of methanol, ethanol or acetone as an extraction solvent, combining the extracting solutions, concentrating to obtain a concentrated solution 1, standing the concentrated solution 1 overnight, adding water, heating for dispersion again, cooling overnight, performing centrifugal separation, drying biscuits to obtain high-content soybean isoflavone, drying extraction residues, adding high-concentration methanol or ethanol for extraction for 2 times, recovering the solvent from the extracting solution under reduced pressure, adding acid to adjust the pH value to 3-4, standing overnight, performing centrifugal separation, and drying the biscuits to obtain the soybean saponin. The technology improves the utilization rate of the soybeans by adopting a mode of extracting and separating a plurality of products step by step, thereby greatly improving the enterprise profits.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a preparation method of isoflavone and saponin in soybeans.
Background
The soybean contains rich functional components, especially special isoflavone and saponin as main effective components, and has anticancer and antiaging effects. The soybean isoflavone in the soybean is a general term of isoflavone, generally comprises 6 components of daidzin, glycitin, genistin and aglycone of the three components, and the daidzin is a more complex saponin mixture. In recent years, soybean has been increasingly emphasized. The soybean product also becomes one of the most advocated health-care foods by people in the world today. Soy isoflavones are also referred to as "botanical natural estrogens" because of their significant estrogen-like effects. The extraction and separation technology of active substances and the raw material resource problem of medicinal plants are key factors for restricting the industrialization of the active substances. On one hand, the soybean contains less active substances such as soybean isoflavone, soybean saponin and the like, the extraction and separation are difficult, the cost of the technology for extracting the effective components and the raw materials for extracting the single medicinal component by taking the soybean as the raw material is high at present, so that the enterprise engaged in the extraction of the natural active substances of the soybean has a tiny profit.
Disclosure of Invention
The invention aims to provide a preparation method of isoflavone and saponin in soybean aiming at the existing problems.
The invention is realized by the following technical scheme:
a method for preparing isoflavone and saponin in soybean comprises the following steps:
(1) heating and refluxing defatted soybean with mixed solvent for 2 times, mixing extractive solutions, and collecting soybean residue;
(2) concentrating the combined extract in the step (1) to obtain a concentrated solution 1, standing the concentrated solution 1 overnight, adding water, heating again for dispersion, cooling overnight, centrifuging, and drying to obtain high-content soybean isoflavone;
(3) heating the soybean residue collected in the step (1) to recover the solvent, drying, adding high-concentration alcohol, performing reflux extraction for 2 times, recovering the solvent from the obtained extracting solution under reduced pressure, adding acid to adjust the pH value to 3-4, standing overnight, performing centrifugal separation, drying the cake to obtain soyasaponin, and collecting the extracted soybean for later use;
(4) and (4) heating the extracted soybeans collected in the step (4) to recover the solvent, and drying to obtain the soybeans for the feed.
Further, the mixed solvent in the step (1) is a mixed solution of ethyl acetate and one of methanol, ethanol or acetone.
Further, the high-concentration alcohol in the step (3) is methanol or ethanol, and the concentration is more than or equal to 85%.
Compared with the prior art, the invention has the following advantages:
the technology improves the utilization rate of the soybeans by adopting a mode of extracting and separating a plurality of products step by step, thereby greatly improving the enterprise profits.
Drawings
Fig. 1 is a flow chart of a preparation method of isoflavone and saponin in soybean provided by the application.
Detailed Description
Implementation mode one
Adding methanol into 300kg of defatted soybean germs: boiling and refluxing for 2h with 2400L mixed solvent of ethyl acetate 1:1, repeating for 2 times, mixing extractive solutions to obtain a liquid A containing soybean isoflavone, heating the extracted soybean material to recover the solvent, adding 2400L 90% methanol for refluxing and extracting for 2 times, mixing the extractive solutions to obtain a liquid B containing soybean saponin, heating the extracted soybean material to recover the solvent, drying to obtain soybean for feed, separately concentrating the liquids A and B to recover the solvents to obtain aqueous solutions C and D, standing for 24h, adding water, centrifuging, drying to obtain 65% soybean isoflavone, adding hydrochloric acid to the solution D containing soybean saponin to adjust pH to 3, standing for 24h, centrifuging, and drying to obtain 72% soybean saponin.
Second embodiment
Adding methanol into 300kg of defatted soybean germs: boiling and refluxing for 2h with 2400L mixed solvent of 2:3 ethyl acetate, repeating for 2 times, mixing extractive solutions to obtain a liquid A containing soybean isoflavone, heating the extracted soybean material to recover the solvent, adding 2400L 90% methanol for refluxing and extracting for 2 times, mixing the extractive solutions to obtain a liquid B containing soybean saponin, heating the extracted soybean material to recover the solvent, drying to obtain soybean for feed, separately concentrating the liquids A and B to recover the solvents to obtain aqueous solutions C and D, standing for 24h, adding water, centrifuging, drying to obtain soybean isoflavone with the content of 75%, adding hydrochloric acid to the solution D containing soybean saponin to adjust the pH to 3, standing for 24h, centrifuging, and drying to obtain soybean saponin with the content of 78%.
Third embodiment
Adding 300kg of defatted soybean germ into ethanol: boiling and refluxing for 2h with 2400L mixed solvent of ethyl acetate 1:1, repeating for 2 times, mixing extractive solutions to obtain a liquid A containing soybean isoflavone, heating the extracted soybean material to recover the solvent, adding 2400L 90% ethanol, refluxing for 2 times, mixing the extractive solutions to obtain a liquid B containing soybean saponin, heating the extracted soybean material to recover the solvent, drying to obtain soybean for feed, separately concentrating the liquids A and B to recover the solvents to obtain aqueous solutions C and D, standing for 24h, adding water, centrifuging, drying to obtain soybean isoflavone with the content of 82%, adding hydrochloric acid to the solution D containing soybean saponin to adjust the pH to 3, standing for 24h, centrifuging, and drying to obtain soybean saponin with the content of 76%.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation. The use of the phrase "comprising one of the elements does not exclude the presence of other like elements in the process, method, article, or apparatus that comprises the element.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (3)
1. A method for preparing isoflavone and saponin in soybean is characterized by comprising the following steps:
(1) heating and refluxing defatted soybean with mixed solvent for 2 times, mixing extractive solutions, and collecting soybean residue;
(2) concentrating the combined extract in the step (1) to obtain a concentrated solution 1, standing the concentrated solution 1 overnight, adding water, heating again for dispersion, cooling overnight, centrifuging, and drying to obtain high-content soybean isoflavone;
(3) heating the soybean residue collected in the step (1) to recover the solvent, drying, adding high-concentration alcohol, performing reflux extraction for 2 times, recovering the solvent from the obtained extracting solution under reduced pressure, adding acid to adjust the pH value to 3-4, standing overnight, performing centrifugal separation, drying the cake to obtain soyasaponin, and collecting the extracted soybean for later use;
(4) and (4) heating the extracted soybeans collected in the step (4) to recover the solvent, and drying to obtain the soybeans for the feed.
2. The method for preparing isoflavones and saponins in soybeans according to claim 1, wherein the mixed solvent in step (1) is a mixed solution of ethyl acetate and one of methanol, ethanol and acetone.
3. The method for preparing isoflavone and saponin in soybean according to claim 1, wherein the high concentration alcohol in step (3) is methanol or ethanol, and the concentration is not less than 85%.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2021106793187 | 2021-06-18 | ||
| CN202110679318.7A CN113318144A (en) | 2021-06-18 | 2021-06-18 | Preparation method of isoflavone and saponin in soybean |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114306421A true CN114306421A (en) | 2022-04-12 |
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| CN202110679318.7A Withdrawn CN113318144A (en) | 2021-06-18 | 2021-06-18 | Preparation method of isoflavone and saponin in soybean |
| CN202210128962.XA Pending CN114306421A (en) | 2021-06-18 | 2022-02-11 | Method for preparing isoflavone and saponin in soybean |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202110679318.7A Withdrawn CN113318144A (en) | 2021-06-18 | 2021-06-18 | Preparation method of isoflavone and saponin in soybean |
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| CN113861152A (en) * | 2021-11-04 | 2021-12-31 | 山东东宇生态科技有限公司 | Preparation method of soybean isoflavone |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315323A (en) * | 2000-03-31 | 2001-10-03 | 姜浩奎 | Process for extracting glycitin and soybean saponin |
| CN1327983A (en) * | 2000-06-08 | 2001-12-26 | 姜浩奎 | Process for continuously extracting glycitin, olegose and saponin |
| CN1683362A (en) * | 2005-02-07 | 2005-10-19 | 黑龙江双河松嫩大豆生物工程有限责任公司 | Method for preparing soybean isoflavone, soybean spanin, oligosaccharide and soybean concentrated protein |
-
2021
- 2021-06-18 CN CN202110679318.7A patent/CN113318144A/en not_active Withdrawn
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2022
- 2022-02-11 CN CN202210128962.XA patent/CN114306421A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315323A (en) * | 2000-03-31 | 2001-10-03 | 姜浩奎 | Process for extracting glycitin and soybean saponin |
| CN1327983A (en) * | 2000-06-08 | 2001-12-26 | 姜浩奎 | Process for continuously extracting glycitin, olegose and saponin |
| CN1683362A (en) * | 2005-02-07 | 2005-10-19 | 黑龙江双河松嫩大豆生物工程有限责任公司 | Method for preparing soybean isoflavone, soybean spanin, oligosaccharide and soybean concentrated protein |
Non-Patent Citations (2)
| Title |
|---|
| 马杰等: "大豆皂苷分离纯化方法研究进展", 《化工时刊》 * |
| 黄进: "大豆活性成分的结构与功能评价——肿瘤细胞凋亡、降糖、抗氧化作用", 《中国优秀博硕士学位论文全文数据库 (博士)工程科技Ⅰ辑》 * |
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| CN113318144A (en) | 2021-08-31 |
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Application publication date: 20220412 |