CN1923845A - Preparation method of high-content soybean saponin - Google Patents
Preparation method of high-content soybean saponin Download PDFInfo
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- CN1923845A CN1923845A CN 200610053603 CN200610053603A CN1923845A CN 1923845 A CN1923845 A CN 1923845A CN 200610053603 CN200610053603 CN 200610053603 CN 200610053603 A CN200610053603 A CN 200610053603A CN 1923845 A CN1923845 A CN 1923845A
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- 244000068988 Glycine max Species 0.000 title claims abstract description 92
- 235000010469 Glycine max Nutrition 0.000 title claims abstract description 92
- 239000001397 quillaja saponaria molina bark Substances 0.000 title claims abstract description 84
- 229930182490 saponin Natural products 0.000 title claims abstract description 84
- 150000007949 saponins Chemical class 0.000 title claims abstract description 84
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000007670 refining Methods 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000012043 crude product Substances 0.000 claims description 26
- 238000001179 sorption measurement Methods 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 238000005406 washing Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003463 adsorbent Substances 0.000 claims description 9
- 238000005119 centrifugation Methods 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000002594 sorbent Substances 0.000 claims description 7
- 238000005194 fractionation Methods 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 235000019764 Soybean Meal Nutrition 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000011010 flushing procedure Methods 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000004455 soybean meal Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 22
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000000284 extract Substances 0.000 abstract description 3
- 239000002893 slag Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 238000010828 elution Methods 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 229920001542 oligosaccharide Polymers 0.000 description 6
- 150000002482 oligosaccharides Chemical class 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 101100366060 Caenorhabditis elegans snap-29 gene Proteins 0.000 description 4
- 238000002203 pretreatment Methods 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 229930187719 Soyasaponin Natural products 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229940094952 green tea extract Drugs 0.000 description 1
- 235000020688 green tea extract Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000020712 soy bean extract Nutrition 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
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- Steroid Compounds (AREA)
Abstract
The invention discloses a preparing method of high-content soybean saponin, which is characterized by the following: adopting the extract of soybean plantule or soybean slag as raw material with total soybean saponin at 1.0-10.0%; adorbing and separating in the adsorbing column to obtain rough product; recrystallizing; refining to obtain the product.
Description
Technical field
The present invention relates to belong to technical field of chemical engineering, a kind of method of extracting high-content soybean saponin from the raw material of low soybean saponin content relates in particular to the technology with adsorption method of separation and crystal refining method purifying soybean saponin(e.
Background technology
Soybean saponin (soyasaponins) claims Soyasaponin again, by extracting in soybean and other bean seed, and a compounds that forms by oligose and the condensation of oleanene triterpene.The content of soybean saponin is generally between 0.62-6.16% in the bean seed.Domestic and international research is verified, and soybean saponin has that the oxidation of lipotropism matter, Green Tea Extract, enhancing immunity are regulated, different physiological roles such as antitumor, antiviral.Be applied to fields such as food, medicine, makeup at present, had vast market prospect.
Soybean saponin preparation technology commonly used at present, generally be with non-polar solvents such as normal hexanes raw material to be carried out skimming treatment earlier, use organic solvent extraction again, extracting solution after filtration, concentrate the water dissolution of back with certain volume, the n-butanol extraction that adds equal volume then promptly gets the soybean saponin crude product after the propyl carbinol phase evaporated under reduced pressure.But this process solvent consumption is big, and the product content that obtains is not high.Macroporous adsorbent resin has been applied to the preparation of soybean saponin in recent years, and it is few that this method has a solvent load, and the characteristics that the rate of recovery is high become the focus of current research.Document about this method is a lot, as Chinese patent CN1245811A, CN1315323A, CN1327983A, CN1422856A, CN1590385A, CN1683362A, Japanese Patent JP2003-171393A etc.Protein content is higher in the soybean, during as extraction agent, though partial protein generation sex change causes that its solubleness significantly reduces, still has a certain amount of protein with ethanol in extracting solution.The protein that exists in the extracting solution influences bigger to concentrated, lock out operation, amounts of protein is easily bubbled and overflowed when concentrating.When directly carrying out the post separation and purification, proteinic flocculation causes upper prop speed slow, and causes that easily the absorption property of sorbent material reduces and the bed latch up phenomenon.Therefore general technology is that extracting solution is carried out the deproteinated pre-treatment.Other patent technology is not carried out deproteinated and is handled, but soybean saponin is extracted, and preparation crude product soybean saponin carries out follow-up purifying again.
(1) extraction process combines with adsorption method of separation: with the soybean saponin extracting solution, extract with the aqueous solution of finite concentration propyl carbinol, solvent is reclaimed in evaporation, thick saponin(e, after macroporous adsorptive resins, use the lower alcohol wash-out, the elutriant spraying drying gets soybean saponin.The solubleness of sugar in propyl carbinol is very low in the soybean extract, and polarity has solubleness preferably than the little saponin(e of sugar in propyl carbinol, and n-butanol/water (about 1: 1) extraction process has utilized this character to separate just.With saponin(e be extracted into propyl carbinol mutually in, oligose is retained in aqueous phase.Problem is that saponin(e still has bigger solubleness at water, and propyl carbinol removes sugar and remove albumen not thorough, and this may be the extraction yield and all unfavorable reason of content of the finished product.When doing the n-butanol/water extraction, the solubleness of propyl carbinol in water is 14%, and this part propyl carbinol is difficult for reclaiming, and in this way divides defection to cause unthinkable solvent consumption, the production cost height.That adopts this type of technology has Chinese patent CN1245811A, a Japanese Patent JP2003-171393A etc.
(2) raw materials pretreatment combines with adsorption method of separation:
The pre-treatment of stock liquid mainly is that ethanol extract is carried out deproteinated, degreasing and desalination etc., and then uses the polymeric adsorbent separation and purification.Present Deproteinated method mainly contains: salt precipitation method, organic solvent precipitation method, isoelectric point method, heavy metal precipitation method, ultrafiltration process etc.Desalting method has electrodialysis etc.This is that great majority extract the step that soybean saponin technology is taked at present, and as Chinese patent CN1315323A, CN1327983A, CN1422856A, CN1590385A, CN1683362A etc., its concrete treatment process is slightly different.The method advantage is a technical maturity, and problem is to need complicated pretreatment equipment, and the operational cycle is long, and cost is higher, and the final soybean saponin content of gained is 70～85%.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of high-content soybean saponin by preferred adsorbent, does not need raw material is carried out any pre-treatment, directly carries out fractionation by adsorption, refining.
The technical solution adopted for the present invention to solve the technical problems is:
Extracting solution with the low soybean saponin content of soybean germ or soybean meal is the high-load soybean saponin of feedstock production, wherein total soybean saponin content is 1.0～10.0% in the extracting solution, feeding is filled with in the adsorption column of sorbent material after the fractionation by adsorption, get the soybean saponin crude product, recrystallize is refining, obtains the high-content soybean saponin of content 〉=96.0%.
Concrete steps are as follows:
1) the soybean saponin extracting solution is fed be filled with in the adsorption column of sorbent material, temperature is 20～80 ℃, flow rate control 0.5～5 times of bed volume/hour;
2) with the water of 1～6 times of bed volume, in 20～80 ℃ of temperature ranges, with 0.5～5 times of bed volume/hour flow velocity wash-out impurity;
3) with 5～35% low-alcohol solutions of 1～6 times of bed volume, in 20～80 ℃ of temperature ranges, with 0.5～5 times of bed volume/hour flow velocity wash-out impurity;
4) with 40～90% low-alcohol solutions of 1～6 times of bed volume, in 20～80 ℃ of temperature ranges, with 0.5～5 times of bed volume/hour flow velocity flushing adsorption column, with elutriant rotary evaporation or the spraying drying that obtains, the soybean saponin crude product;
5) above-mentioned soybean saponin crude product reflux is dissolved in 5～45% the recrystallisation solvent, liquid-solid ratio is 4～20: 1, and solution is cooled to 0～35 ℃ of crystallization, through centrifugation, washing, dry high-content soybean saponin.
Described lower alcohol is methyl alcohol or ethanol; Described sorbent material is polymeric amide and/or macroporous adsorbent resin, and macroporous adsorbent resin can be used the nonpolar or low-pole macroporous adsorbent resin of aromatic series, and its aperture is 10～30nm; Be HPD-100, HPD-300, HPD-600, ADS-8, ADS-7, XAD-2, XAD-4 or XAD-16 resin.
Described recrystallisation solvent is two or more a mixed solvent of water and methyl alcohol, ethanol or Virahol.
The useful effect that the present invention has is:
The present invention includes steps such as fractionation by adsorption, crystal refining, provide a brand-new technical process.Outstanding advantage is not need raw material is carried out any pre-treatment, directly carry out the initial gross separation purifying with adsorption separating method, first in conjunction with crystal refining method purifying soybean saponin, products obtained therefrom content height (soybean saponin content 〉=96.0%), the yield height, lighter color, and this method technical process is simple, production cost is low, is easy to industrialization.
Embodiment
Embodiment 1:
Adsorption column size Φ 28 * 750mm.The interior dress about 90g of ADS-7 resin (, as follows) with dry weight basis.Last sample soybean saponin material concentration is 6.5mg/ml, and soybean saponin content is 1.5% in the dry-matter, and last sample volume is 1000ml, and last sample and eluting temperature are 80 ℃.With the 460ml washing, last sample effluent liquid and water lotion merge the dry soybean oligosaccharide crude product that gets earlier; Wash adsorption column with 1400ml35% ethanol again; Use the 1200ml60% ethanol elution at last, flow velocity 8.0ml/min collects the soybean saponin elutriant, and elution volume is 1150ml.Vacuum rotation evaporate to dryness gets soybean saponin crude product 13.13g, is pale brown look, content 45.5%.Yield is 91.9%.Above-mentioned soybean saponin crude product is put into the 250ml round-bottomed flask, add 50ml40% ethanol, reflux, temperature is 85 ℃, pours centrifuge tube then into, and 30 ℃ are cooled off 24h down, centrifugation mother liquor and crystallization, washing back recentrifuge gets crystalline product, the dry product 3.32g that gets.The HPLC analytical results shows that the soybean saponin total content is 99.0% in the product, yield 55.0%.
Embodiment 2:
Adsorption column size Φ 28 * 750mm.The about 90g of interior dress HPD-100.Last sample soybean saponin material concentration is 6.5mg/ml, and soybean saponin content is 9.5% in the dry-matter, and last sample volume is 320ml, and last sample and eluting temperature are 25 ℃.With the 2500ml washing, last sample effluent liquid and water lotion merge the dry soybean oligosaccharide crude product that gets earlier; Wash adsorption column with 460ml20% ethanol again; Use the 250ml70% ethanol elution at last, flow velocity 10ml/min collects the soybean saponin elutriant, and elution volume is 240ml.Vacuum rotation evaporate to dryness gets soybean saponin crude product 3.20g, is pale brown look, content 30.0%.Yield is 46.1%.Above-mentioned soybean saponin crude product is put into the 250ml round-bottomed flask, add 60ml40% methyl alcohol, reflux, temperature is 85 ℃, pours centrifuge tube then into, and 0 ℃ is cooled off 12h down, centrifugation mother liquor and crystallization, washing back recentrifuge gets crystalline product, the dry product 1.02g that gets.The HPLC analytical results shows that the soybean saponin total content is 70.0% in the product, yield 48.4%.
Embodiment 3:
Chromatography column size Φ 20 * 480mm.Interior dress ADS-8 resin 30g.Last sample soybean saponin material concentration is 3.25mg/ml, and soybean saponin content is 6.0% in the dry-matter, and last sample volume is 460ml, and last sample and eluting temperature are 50 ℃.With the 450ml washing, last sample effluent liquid and water lotion merge the dry soybean oligosaccharide crude product that gets earlier; Wash adsorption column with 900ml5% ethanol again; Use 90% ethanol elution at last, flow velocity 10ml/min collects the soybean saponin elutriant, and elution volume is 375ml.Vacuum rotation evaporate to dryness gets soybean saponin crude product 2.45g, is pale brown look, content 55.0%.Yield is 90.0%.Above-mentioned soybean saponin crude product is put into the 50ml round-bottomed flask, add 10ml30% ethanol, reflux, temperature is 85 ℃, pours centrifuge tube then into, 25 ℃ of cooling 24h, centrifugation mother liquor and crystallization, washing back recentrifuge gets crystalline product, the dry product 1.48g that gets.The HPLC analytical results shows that the soybean saponin total content is 99.1% in the product, yield 60.0%.
Embodiment 4:
Adsorption column size Φ 30 * 800mm.The about 115g of interior dress XAD-2 resin.Last sample soybean saponin material concentration is 6.5mg/ml, and soybean saponin content is 2.7% in the dry-matter, and last sample volume is 1100ml, and last sample and eluting temperature are 60 ℃.With the 1100ml washing, last sample effluent liquid and water lotion merge the dry soybean oligosaccharide crude product that gets earlier; Wash adsorption column with 1950ml25% methyl alcohol again; Use the 1200ml80% methanol-eluted fractions at last, flow velocity 10.0ml/min collects the soybean saponin elutriant, and elution volume is 1100ml.Vacuum rotation evaporate to dryness gets soybean saponin crude product 14.1g, is pale brown look, content 46.0%.Yield is 90.7%.Above-mentioned soybean saponin crude product is put into the 250ml round-bottomed flask, add 170ml40% methyl alcohol, reflux, temperature is 88 ℃, pours centrifuge tube then into, and 20 ℃ are cooled off 24h down, centrifugation mother liquor and crystallization, washing back recentrifuge gets crystalline product, the dry product 3.07g that gets.The HPLC analytical results shows that the soybean saponin total content is 88.0% in the product, yield 57.0%.
Embodiment 5:
Adsorption column size Φ 28 * 800mm.The about 100g of interior dress HPD-600 resin.Last sample soybean saponin material concentration 5.5mg/ml, soybean saponin content is 10.0% in the dry-matter, and last sample volume is 1000ml, and last sample and eluting temperature are 60 ℃.With the 1200ml washing, last sample effluent liquid and water lotion merge the dry soybean oligosaccharide crude product that gets earlier; Wash adsorption column with 1000ml30% ethanol again; Use the 1200ml60% ethanol elution at last, flow velocity 8.0ml/min collects the soybean saponin elutriant.Vacuum rotation evaporate to dryness gets soybean saponin crude product 9.87g, is pale brown look, content 50.6%.Yield is 90.8%.Above-mentioned soybean saponin crude product is put into the 250ml round-bottomed flask, add 40ml40% ethanol, reflux, temperature is 85 ℃, pours centrifuge tube then into, and 25 ℃ are cooled off 24h down, centrifugation mother liquor and crystallization, washing back recentrifuge gets crystalline product, the dry product 3.07g that gets.The HPLC analytical results shows that the soybean saponin total content is 98.0% in the product, yield 50.0%.
Embodiment 6:
Adsorption column size Φ 28 * 750mm.The about 90g of interior dress polyamide resin.Last sample soybean saponin material concentration 6.5mg/ml, soybean saponin content is 3.0% in the dry-matter, and last sample volume is 1000ml, and last sample and eluting temperature are 60 ℃.With the 1100ml washing, last sample effluent liquid and water lotion merge the dry soybean oligosaccharide crude product that gets earlier; Wash adsorption column with 900ml20% ethanol again; Use the 1100ml70% ethanol elution at last, flow velocity 8.0ml/min collects the soybean saponin elutriant.Vacuum rotation evaporate to dryness gets soybean saponin crude product 15.1g, is pale brown look, content 39.0%.Yield is 90.8%.Above-mentioned soybean saponin crude product is put into the 250ml round-bottomed flask, add the 60ml40% Virahol, reflux, temperature is 80 ℃, pours centrifuge tube then into, 20 ℃ of cooling 24h, centrifugation mother liquor and crystallization, washing back recentrifuge gets crystalline product, the dry product 3.38g that gets.The HPLC analytical results shows that the soybean saponin total content is 90.0% in the product, yield 51.7%.
Claims (4)
1. the preparation method of a high-content soybean saponin, it is characterized in that: the extracting solution with the low soybean saponin content of soybean germ or soybean meal is the high-load soybean saponin of feedstock production, wherein total soybean saponin content is 1.0～10.0% in the extracting solution, feeding is filled with in the adsorption column of sorbent material after the fractionation by adsorption, get the soybean saponin crude product, recrystallize is refining, obtains the high-content soybean saponin of content 〉=96.0%.
2. the preparation method of a kind of high-content soybean saponin according to claim 1 is characterized in that concrete steps are as follows:
1) the soybean saponin extracting solution is fed be filled with in the adsorption column of sorbent material, temperature is 20～80 ℃, flow rate control 0.5～5 times of bed volume/hour;
2) with the water of 1～6 times of bed volume, in 20～80 ℃ of temperature ranges, with 0.5～5 times of bed volume/hour flow velocity wash-out impurity;
3) with 5～35% low-alcohol solutions of 1～6 times of bed volume, in 20～80 ℃ of temperature ranges, with 0.5～5 times of bed volume/hour flow velocity wash-out impurity;
4) with 40～90% low-alcohol solutions of 1～6 times of bed volume, in 20～80 ℃ of temperature ranges, with 0.5～5 times of bed volume/hour flow velocity flushing adsorption column, with elutriant rotary evaporation or the spraying drying that obtains, the soybean saponin crude product;
5) above-mentioned soybean saponin crude product reflux is dissolved in 5～45% the recrystallisation solvent, liquid-solid ratio is 4～20: 1, and solution is cooled to 0～35 ℃ of crystallization, through centrifugation, washing, dry high-content soybean saponin.
3. the preparation method of a kind of high-content soybean saponin according to claim 2, it is characterized in that: described lower alcohol is methyl alcohol or ethanol; Described sorbent material is polymeric amide and/or macroporous adsorbent resin, and macroporous adsorbent resin can be used the nonpolar or low-pole macroporous adsorbent resin of aromatic series, and its aperture is 10～30nm; Be HPD-100, HPD-300, HPD-600, ADS-8, ADS-7, XAD-2, XAD-4 or XAD-16 resin.
4. the preparation method of a kind of high-content soybean saponin according to claim 1 is characterized in that: said recrystallisation solvent is two or more a mixed solvent of water and methyl alcohol, ethanol or Virahol.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2006100536033A CN100402547C (en) | 2006-09-26 | 2006-09-26 | Preparation method of high-content soybean saponin |
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| CNB2006100536033A CN100402547C (en) | 2006-09-26 | 2006-09-26 | Preparation method of high-content soybean saponin |
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| CN100402547C CN100402547C (en) | 2008-07-16 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101392016A (en) * | 2008-10-07 | 2009-03-25 | 上海同田生物技术有限公司 | Method for preparing high-purity soybean saponin A and B |
| CN102516349A (en) * | 2011-11-03 | 2012-06-27 | 北京化工大学 | Preparation method of soyasaponin B |
| CN103319563A (en) * | 2012-03-22 | 2013-09-25 | 东北农业大学 | Extraction and purification method of soyasaponins |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1111539C (en) * | 1999-08-05 | 2003-06-18 | 哈尔滨医科大学公共卫生学院 | From the skimmed soy beans dregs of beans, extract the method for Soyasaponin |
| CN1109682C (en) * | 2000-03-31 | 2003-05-28 | 姜浩奎 | Process for extracting glycitin and soybean saponin |
| JP2003171393A (en) * | 2001-12-04 | 2003-06-20 | Osaka Yakuhin Kenkyusho:Kk | Method for producing high-purity soybean saponin |
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2006
- 2006-09-26 CN CNB2006100536033A patent/CN100402547C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101392016A (en) * | 2008-10-07 | 2009-03-25 | 上海同田生物技术有限公司 | Method for preparing high-purity soybean saponin A and B |
| CN101392016B (en) * | 2008-10-07 | 2013-01-02 | 上海同田生物技术股份有限公司 | Method for preparing high-purity soybean saponin A and B |
| CN102516349A (en) * | 2011-11-03 | 2012-06-27 | 北京化工大学 | Preparation method of soyasaponin B |
| CN102516349B (en) * | 2011-11-03 | 2013-11-13 | 北京化工大学 | Preparation method of soyasaponin B |
| CN103319563A (en) * | 2012-03-22 | 2013-09-25 | 东北农业大学 | Extraction and purification method of soyasaponins |
| CN103319563B (en) * | 2012-03-22 | 2015-06-17 | 东北农业大学 | Extraction and purification method of soyasaponins |
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| Publication number | Publication date |
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| CN100402547C (en) | 2008-07-16 |
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