CN1107065C - Methof of extracting isoflavone, saponin, oligosaccharide and protein simultaneously from defatted soybean dregs - Google Patents
Methof of extracting isoflavone, saponin, oligosaccharide and protein simultaneously from defatted soybean dregs Download PDFInfo
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- CN1107065C CN1107065C CN00122917A CN00122917A CN1107065C CN 1107065 C CN1107065 C CN 1107065C CN 00122917 A CN00122917 A CN 00122917A CN 00122917 A CN00122917 A CN 00122917A CN 1107065 C CN1107065 C CN 1107065C
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- saponin
- isoflavones
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- 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 41
- 235000008696 isoflavones Nutrition 0.000 title claims abstract description 41
- 239000001397 quillaja saponaria molina bark Substances 0.000 title claims abstract description 35
- 229930182490 saponin Natural products 0.000 title claims abstract description 35
- 150000007949 saponins Chemical class 0.000 title claims abstract description 34
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 8
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 8
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- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 title abstract description 6
- 229920001542 oligosaccharide Polymers 0.000 title abstract description 5
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 150000002515 isoflavone derivatives Chemical class 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
- 238000004587 chromatography analysis Methods 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 10
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 10
- 239000003463 adsorbent Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000010612 desalination reaction Methods 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
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- 239000002253 acid Substances 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003957 anion exchange resin Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 1
- 229920002521 macromolecule Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 12
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- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The present invention relates to a method for extracting isoflavone, saponin, oligosaccharide and protein from defatted soybean meal at the same time. Defatted soybean meal is extracted with a solvent so as to separate soybean protein and other active substances; oligosaccharide with a high content is prepared by a technology of column chromatography and membrane ultrafiltration; isoflavone and saponin are separated and purified by a technology of gradient elution and recrystallization. Because an integrative preparation technology is used, the method can achieve the complete separation and extraction of active substances in soybean meal, avoid resource wasting and environmental pollution caused by the preparation of single product or two products, reduce product cost and increase benefits; meanwhile, the method is suitable for industrialization production.
Description
Affiliated technical field
The present invention relates to a kind of isoflavones, saponin, oligose and proteic method from defatted soybean meal, extracted simultaneously, belong to the comprehensive production technology that on same production line, separates four kinds of activess of soybean.
Background technology
Contain multiple micro-biologically active substance in soybean or the defatted soybean meal, can prevent and treat multiple disease, make soybean become global heath food geared to the 21st century.Studies show that soybean isoflavones has faint female hormone and anti-oxidant activity, can suppress the generation of leukemia, colorectal carcinoma, lung cancer effectively, also can prevent osteoporosis.But the Soyasaponin reducing blood-fat, anti-oxidant, prevent arteriosclerosis, regulate immunologic function also have the inhibition growth of tumour cell, suppress thrombopenia and anti thrombotic action.Soybean oligosaccharide is the selectivity picked-up sugar of bifidus bacillus in the human body intestines, can promote the propagation of bifidus bacillus, improves intestinal flora and distributes, and suppresses the breeding of intestinal toxic bacterium and the generation of corrupt substance.
About single preparation and production of planting active substance, research and report are all arranged both at home and abroad, the production technology of soybean protein is mature on the whole, the research of soybean oligosaccharide, Soyasaponin, soybean isoflavones then is the thing of nearly more than ten years, so their production and product development become the current focus that grinds, studies carefully both at home and abroad.At present, the mode of production both domestic and external mainly is the production of single kind or two kinds of activess, these modes of production; when obtaining desired product, other activess are many to be run off or is discharged because of ignorance, causes the wasting of resources and environmental pollution; make product cost higher again, influence large-scale production.
Summary of the invention
The purpose of this invention is to provide a kind of isoflavones, saponin, oligose and proteic method from de-fatted soybean dregs, extracted simultaneously; four kinds of active substances that adopt this method to produce simultaneously; the yield height; quality is good; cost is low; pollute for a short time, realized making full use of of soybean resource, be suitable for large-scale production.
For achieving the above object, the present invention has adopted following method:
(1) dregs of beans extracts: water or food grade organic solvent extraction, and the extraction yield height, product is volatility not, and filtration or centrifugal gets insolubles (I) and filtrate (II).
(2) produce albumen: insolubles (I) but convection drying pulverize and produce content greater than 55% protein concentrate, also insolubles (I) can be pulverized, add 10-15 times of water, 30-60 ℃ is stirred extraction 30-60min, separates rear filtrate (IV), adding acid accent pH is 4.2-4.5, protein precipitation separates, washes, and transferring pH is 7.0, spraying drying under 12-15% concentration, the protein isolate of content about 90%.
(3) chromatography column separates: filtrate (II) is evaporated to original volume 1/3 under 70-75 ℃, and concentrated solution is passed through the polymeric adsorbent chromatography column.
(4) oligose extracts: the effluent liquid of chromatography column (III), through decolouring, ultrafiltration, the desalination of yin, yang ion exchange resin, vacuum-drying, content greater than 90% oligose.
(5) chromatography column wash-out: can adopt gradient elution, reach and separate isoflavones and saponin, also the disposable wash-out of useable solvents through concentrate drying, gets the mixing crude product of isoflavones and saponin.
(6) purifying of isoflavones, saponin: can adopt recrystallization method, getting content is the isoflavones of 30-80% and the saponin of 20-80%, also can adopt fractional precipitation, dissolution with solvents with easy solubilize isoflavones and saponin, agitation and dropping is in the solvent of insoluble saponin, the saponin of purifying generates with precipitation, and the supernatant drying gets the purifying isoflavones.
(7) detect: the present invention adopts high performance liquid chromatography (HPLC), and UV-detector is used in the detection of isoflavones, saponin; Differential refraction detector is used in the detection of oligose; The soybean protein Kjeldahl determination.
Used dregs of beans extractive technique among the present invention, can be immersion, diacolation or both combinations, also can pulverize dregs of beans, solubilizing agent stirs extraction, extraction agent can be a water, also can be methyl alcohol, ethanol, Virahol, acetone, methylethylketone, dimethyl formamide or their aqueous solution, and the concentration of solution is 20-60%, extract 30-50 ℃ of temperature, extraction agent and raw material dregs of beans are than 10-15: 1.
The used polymeric adsorbent of chromatography column among the present invention, it can be domestic macroporous polystyrene polymeric adsorbent, also can be that Japanese Diaion HP is that class or U.S. are class macropore styrene resin with Amberite XAD, the most handy homemade polymeric adsorbent, adsorption temp be 20-50 ℃.
The used membrane ultrafiltration device of the present invention can be tubular fibre or plate ultra-fine filter, and 6000-10000 dalton is preferably selected for cutting component 2000-30000 dalton in the aperture of film, and membrane separation apparatus is operated with the ultrafiltration pattern.
The chromatography column elution technique that the present invention is used can be a gradient elution, also can be one-step elution.Eluent can be methyl alcohol, ethanol, Virahol, acetone, methylethylketone, methyl-sulphoxide, dimethyl formamide, can be their aqueous solution also, during gradient elution, the change in concentration scope of two kinds of eluents be 10-90%, the concentration of one-step elution agent is 70-90%, preferably 80%.
The recrystallization technology that the present invention is used, solvent can be methyl alcohol, ethanol, Virahol, and the aqueous solution of alcohols such as propyl carbinol can be the aqueous solution of ketones such as acetone, methylethylketone also, and concentration of aqueous solution is 20-95%.
Fractional precipitation among the present invention, used easy the to be molten isoflavones and the solvent of saponin are methyl alcohol, ethanol; The solvent that is difficult for molten saponin can be ether, ethyl acetate, also can be chloroform.
The discoloring agent that contains the oligose elutriant that the present invention is used can be a gac, also can be macroreticular weakly base styrene series anion exchange resin D301R, D370, D371 or MN200.The desalination resin can be storng-acid cation exchange resin 732,001, Japanese Diaion K or U.S. Amberite IR-120, also can be strongly basic anion exchange resin 717, D-201T D296 or Diaion PA, and desalination, bleaching temperature are 20-50 ℃.
Embodiment
Describe the present invention in detail below in conjunction with embodiment.
Embodiment one:
1. the extraction of raw material dregs of beans
Get the 200g defatted soybean meal, methanol solution with 60%, 50 ℃ reflux to stir were extracted 4 hours, and methanol solution is heavy 10 times of raw material, concentrated extracting solution, reclaim methyl alcohol, cross Japanese HP-20 adsorption resin column, adsorptive is with 80% ethanolic soln wash-out on the post, and concentrate drying gets the isoflavones crude product, surveying isoflavone content with HPLC is 22.0%, and the yield of product is 1.45%.
2. the gradient elution after chromatography column adsorbs
Get raw material 200g, use 60% methanol extraction, concentrated extracting solution reclaims methyl alcohol, crosses Japanese HP-20 macroporous adsorptive resins, and with 0%-95% ethanol/water gradient elution, eluting temperature is a room temperature, the eluate composition such as the following table of each concentration section
The distribution of table 1 gradient elution thing
| Alcohol concn | Eluate distributes |
| 0-20％ 20-40％ 40-95％ | Phenolic acid and carbohydrate (no isoflavones and saponin) isoflavones glucoside (content 20-50%) saponin (content 20-60%), a small amount of isoflavone aglycones |
3. recrystallization purifying isoflavones
Get the isoflavones crude product 3g of content about 20%, with the methyl alcohol or the aqueous ethanolic solution of different concns, postcooling is filtered in the reflux dissolving, and refrigerator is placed and spent the night, and separates out crystallization, removes the supernatant after drying, result such as table 2
The relation of table 2 recrystallization solvent concentration and isoflavones extraction effect
| Determining alcohol (%) | 50 80 85 90 93 95 |
| Yield (%) isoflavone content (%) | 70.0 45.0 27.0 17.0 14.0 9.4 25.7 32.1 37.4 41.6 43.4 47.7 |
4. the decolouring of oligose, desalination.
Extracting degreasing dregs of beans 500g, with 4500g 60% methanol solution, room temperature diacolation 20 hours, 200 order filtering separation, extracting solution is concentrated into 1.5L, cross the HP-20 chromatography column, effluent liquid behind Zeo-karb 732, anionite-exchange resin 717 and polymeric adsorbent MN 200 desalination bleachings, ultrafiltration, concentrate, dry solid oligose, the decolouring of different resins, decolorizing effect such as the table 3 of getting
Table 3 different resins desalination bleaching is to the influence of oligose
| Numbering | Processing sequence yield (%) content (%) color |
| 1 2 3 | 732 → MN200 → ultrafiltration 8.4 95.0 little yellow 732 → MN200 → 732 → 717 → ultrafiltration, 8.3 96.5 whites, 732 → MN200 → 717 → 732 → ultrafiltration 8.0., 97.5 whites |
Embodiment two: comprehensive production whole process test extracting degreasing dregs of beans 1Kg, and with diacolation under the 60% methanol aqueous solution room temperature of 10 times (W/W) amount 20 hours, 200 order filtering separation, insolubles is proposed acid through water and is sunk, and spraying drying must be separated albumen.50 ℃ of simmer down to 2-3L of extracting solution cross the HP-20 chromatography column.Effluent liquid decolours through polymeric adsorbent, ultrafiltration, zwitterion exchange tree refers to desalination, concentrate drying gets oligose, chromatography column 80% ethanol elution, elutriant be through concentrate drying, content is 20% isoflavones crude product, extraction using alcohol with 90%, content is higher than 40% isoflavones and 20% saponin.Result such as table 4
Table 4 whole process test-results
*91.4% is the albumen convection drying, and 93.4% is protein liquid ultrafiltration after drying
*77.5% is recrystallization product once more
| Isoflavones saponin oligose protein isolate | |
| Yield (%) content (%) extraction yield (%) | 1.06 0.39 0.61 6.0 30.0 20.0 40.0 20.3 **77.5 95.0 *91.4/93.4 84.8 62.5 40.0 46.1 73.1 |
By above-mentioned example, the present invention and existing production technology relatively have following advantage:
1, on a production line, produce four kinds of products simultaneously, realized that the comprehensive of defatted soybean meal effectively utilizes, and reduced the environmental pollution that Litter causes.
2, the yield height of product, quality is good, has reduced product cost, has improved benefit.
3, technical process is simple and easy to do.
4, do not introduce Harmful chemicals in the process, be not attended by chemical side reactions and take place, kept the peculiar property of soybean green food.
Claims (7)
1. one kind is extracted isoflavones, saponin, oligose and proteic method simultaneously from de-fatted soybean dregs:
(1) dregs of beans extracts: water or food grade organic solvent extraction, and filtration or centrifugal gets insolubles (I) and filtrate (II);
(2) produce albumen: insolubles (I) but convection drying pulverize and produce protein concentrate, also insolubles (I) can be pulverized, add 10-15 times of water, 30-60 ℃ is stirred extraction 30-60min, gets filtrate (IV) after the separation, adding acid accent PH is 4.2-4.5, protein precipitation separates, washes, and transferring PH is 7.0, spraying drying under 12-15% concentration must be separated albumen;
(3) chromatography column separates: filtrate (II) is evaporated to original volume 1/3 under 70-75 ℃, and concentrated solution is passed through the polymeric adsorbent chromatography column;
(4) oligose extracts: the effluent liquid of chromatography column (III) is through decolouring, ultrafiltration, the desalination of yin, yang ion exchange resin, and vacuum-drying gets oligose;
(5) chromatography column wash-out: can adopt gradient elution, reach and separate isoflavones and saponin, also the disposable wash-out of useable solvents through concentrate drying, gets the mixing crude product of isoflavones and saponin; Described eluent can be methyl alcohol, ethanol, Virahol, acetone, methylethylketone, methyl-sulphoxide, dimethyl formamide or their aqueous solution, and the eluant strength variation range is 10-90% in the gradient elution, and the concentration of one-step elution agent is 70-90%;
(6) purifying of isoflavones, saponin: can adopt recrystallization method, getting content is the isoflavones of 30-80% and the saponin of 20-80%, also can adopt fractional precipitation, dissolution with solvents with easy solubilize isoflavones and saponin, agitation and dropping is in the solvent of insoluble saponin, the saponin of purifying generates with precipitation, and the supernatant drying gets the purifying isoflavones.
2. isoflavones, saponin, oligose and the proteic method from de-fatted soybean dregs, extracted simultaneously according to claim 1, described extraction agent handle the dregs of beans mode can be immersion, diacolation or dregs of beans after crushed, solubilizing agent stirs and extracts; Used extraction agent is water, methyl alcohol, ethanol, Virahol, propyl alcohol, methylethylketone, dimethyl formamide or their aqueous solution, if use the aqueous solution, its concentration is 20-60%, and extracting temperature is 30-50 ℃.
3. isoflavones, saponin, oligose and the proteic method from de-fatted soybean dregs, extracted simultaneously according to claim 1 and 2, the used polymeric adsorbent of described chromatography column is a domestic macroporous vinylbenzene polymeric adsorbent, Japan Diaion HP system or Amberite XAD are macropore vinylbenzene polymeric adsorbent, and adsorption temp is 20-50 ℃.
4. isoflavones, saponin, oligose and the proteic method from de-fatted soybean dregs, extracted simultaneously according to claim 1, described chromatography column effluent liquid (III) is after decolouring, by tubular fibre or the ultrafiltration of flat sheet membrane separator, remove macromolecule protein, the cutting component of film is 2000-3000 dalton, and membrane separation apparatus is operated with the ultrafiltration pattern.
5. isoflavones, saponin, oligose and the proteic method from de-fatted soybean dregs, extracted simultaneously according to claim 1, the decolouring of described chromatography column effluent liquid (III), available domestic macroporous vinylbenzene weak base anion-exchange resin or use activated carbon decolorizing, or both use simultaneously.
6. according to claim 1,4 or 5 described a kind of isoflavones, saponin, oligose and proteic methods from de-fatted soybean dregs, extracted simultaneously, the desalination of described membrane ultrafiltration device filtrate, use storng-acid cation exchange resin, strongly basic anion exchange resin, or both dual-purposes.
7. isoflavones, saponin, oligose and the proteic method from de-fatted soybean dregs, extracted simultaneously according to claim 1, described recrystallization solvent is methyl alcohol, ethanol, Virahol, propyl carbinol, acetone, methylethylketone, in the described fractional precipitation, insoluble saponin solvent is ether, chloroform or ethyl acetate.
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| CN100345837C (en) * | 2005-01-31 | 2007-10-31 | 重庆工学院 | Extraction of soya isoflavone, concentrated soya protein and soya oligose |
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| CN101558814B (en) * | 2009-05-15 | 2011-10-12 | 山东省高唐蓝山集团总公司 | Production technology of dual-crop compound protein isolates |
| CN102010460B (en) * | 2010-09-27 | 2012-08-22 | 厦门盛洲植物油有限公司 | Tea seed polypeptide and preparation method thereof |
| CN103493968B (en) * | 2013-09-23 | 2014-09-03 | 河南科技大学 | Preparation method of high-purity peony seed protein powder for oil |
| CN104543802A (en) * | 2014-12-17 | 2015-04-29 | 方萌 | Method for extracting soybean oligosaccharides from soybeans |
| CN113234120A (en) * | 2021-05-28 | 2021-08-10 | 吉林省农业科学院 | Method for efficiently extracting low-abundance protein from soybean seeds |
| CN115286603A (en) * | 2022-08-30 | 2022-11-04 | 三原利华生物技术有限公司 | Method for preparing soybean isoflavone and soyasaponin based on defatted soybean germ |
| CN116675665A (en) * | 2023-04-21 | 2023-09-01 | 长春大学 | Extraction method of soybean isoflavone, soyasaponin, soyastachyose and raffinose without participation of organic chemical solvent |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1211573A (en) * | 1998-09-22 | 1999-03-24 | 北京市农林科学院畜牧兽医研究所 | Method for extracting isoflavone from soybean |
| CN1216685A (en) * | 1997-10-31 | 1999-05-19 | 蛋白质技术国际公司 | Aglucone isoflavone enriched vegetable protein extract and isolate and process for producing |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1216685A (en) * | 1997-10-31 | 1999-05-19 | 蛋白质技术国际公司 | Aglucone isoflavone enriched vegetable protein extract and isolate and process for producing |
| CN1211573A (en) * | 1998-09-22 | 1999-03-24 | 北京市农林科学院畜牧兽医研究所 | Method for extracting isoflavone from soybean |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100345837C (en) * | 2005-01-31 | 2007-10-31 | 重庆工学院 | Extraction of soya isoflavone, concentrated soya protein and soya oligose |
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