CN1120163C - Soybean isoflavone and its prepn process with macroporous adsorption resin - Google Patents
Soybean isoflavone and its prepn process with macroporous adsorption resin Download PDFInfo
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Abstract
The present invention relates to a product of soybean isoflavone and a method for separating and preparing the product of soybean isoflavone from soybeans or soybean products; the product of soybean isoflavone is basically prepared from daidzin, isoshy, genistein and 4', 5, 7-trihydroisoflavon. The purity of each one of the four main components is over 50%. The preparing method comprises: raw materials are extracted with methanol solution to prepare extracting solution; the method has the advantages of low production cost, simple technology, high content of effective component and stable quality, and provides possibility for industrialization production.
Description
Technical field
The present invention relates to soybean isoflavones and preparation method thereof, relate in particular to the high-purity soybean isoflavone product and the industrialized preparing process thereof that adopt through the specificity macroporous adsorbent resin preparation of screening.
Background technology
Soybean isoflavones is a kind of plant estrogen, it has estrogenic physiological function, studies show that, soybean isoflavones can effectively suppress common multiple illnesss such as human breast cancer, prostate cancer and colorectal carcinoma, control middle aged and aged women osteoporosis is had important effect, but do not have the side effect of general hormone.In view of the nourishing function of soybean isoflavones excellence, research and extraction soybean isoflavones have become a focus of this area.
Soybean isoflavones is the osajin biologically active substance that is contained in soybean and the soya products, comprise 12 kinds of isomer compositions, their total contents in soybean are very low, on average have only about 0.2～0.3%, and the solubleness in water are lower, mainly be dissolved in the pure soluble solvent, in addition, complicated component in the soybean has many compositions such as soybean oligosaccharide, pigment etc. close with the character of soybean isoflavones, difficult the separation, make the highly purified isoflavones of production preparation become the bigger problem of technical difficulty.
Before the present invention, the relevant research report that extracts the preparation soybean isoflavones has a lot, record according to these prior aries, the extraction preparation method of soybean isoflavones generally comprise soy material degreasing, extract, handle processes such as extracting solution (deserving to be called post), alcoholic solution wash-out with adsorption column with water-soluble alcoholic solution, elutriant promptly obtains the soybean isoflavones product through concentrate drying.In the aforesaid method, influencing the yield of product and the factor of purity mainly is determining of upper prop and elution requirement, the polymeric adsorbent of generally selecting for use is ethyl-vinyl benzene-Vinylstyrene, vinylbenzene-Vinylstyrene, or poly styrene polymer, can be Ionized or nonionicization, but test-results shows, such resin is not strong to the specificity of absorption soybean isoflavones, through primary sorption, total purity of the isoflavones components for preparing behind the wash-out has only 20～30% at most (can be referring to day disclosure special permission communique, clear 62-126186), for obtaining highly purified soybean isoflavones, must further take other refining means such as recrystallization, for example application number is in 98119864.3 the Chinese patent disclosed method, two one-step hydrolysis have been adopted, hydrolysis is for the first time carried out before column chromatography, hydrolysis is for the second time carried out behind column chromatography, and product also need be made with extra care, and just can obtain highly purified isoflavones product; For another example U.S. Pat P.5,679,806, extracting product need be through comprising repeatedly purified process such as activated carbon decolorizing, methanol crystallization, and the purity of product has improved like this, but multi-pass operations causes loss big, the product yield is reduced, and production cost improves greatly, thereby can't suitability for industrialized production.
According to textual criticism, have only indivedual producers of the U.S. and Japan that this launch is arranged at present, the domestic unit that is engaged in this research is a lot, but only rest on laboratory stage, the major cause that hinders progress is the specificity resin that does not screen special adsorption function as yet, and product purity and yield are low, complex production process, cause the production cost height, product lacks the market competitiveness.
Summary of the invention
One of purpose of the present invention provides a kind of highly purified soybean isoflavones product, and it, can be used as foodstuff additive or be used for the manufacturing of protective foods more than 50% in the purity of the total amount of four kinds of main isomer compositions.
Another main purpose of the present invention is to provide a kind of processing method of extracting the preparation high-purity soybean isoflavone, by having filtered out specific macroporous adsorbent resin, cooperate the manipulation that adapts, adopt single stage method absorption to free purifying process, prepare purity up to the soybean isoflavones product more than 50%, reduce production cost, thereby realized suitability for industrialized production.
In 12 kinds of isomer compositions that soybean isoflavones comprises, the main component of generally acknowledging has 4 kinds, they are daidzin (Daidzin, abbreviation D), daidzein (Daidzein, abbreviation De), Genistoside (Genistin, be called for short G) and genistein (Genistein is called for short Ge), its structural formula is as follows:
The daidzin Genistoside
Daidzin(D) Genistin(G)
The daidzein genistein
Daidzein(De) Genistein(Ge)
It is former that the isoflavone aglycone decomposition obtains corresponding glycosides, a large amount of in vitro testss confirms, the composition that soybean isoflavones has physiologically active is that glycosides is former, and show that through in vivo test the isoflavones that contains glucosides has above-mentioned functions equally, this is because the intestinal bacteria enzyme has the ability of excision glucosides in the organism, iso-flavone glucoside can be former by becoming glycosides after the intestinal bacteria effect, and the form with free isoflavones after small intestine absorbs works.Someone is with the animal model test soybean isoflavones during to the influencing of rat fat and peroxidation state, make feeding study with isoflavone aglycone is former with iso-flavone glucoside respectively, the result shows both effect characteristics and effect basically identicals, the former glucosides that slightly is better than of the glycosides of equivalent weight can conclude it is the different caused differences of molecular weight.Therefore when the inventor thought soybean isoflavones as foodstuff additive or protective foods, it was former to there is no need that isoflavone aglycone is resolved into glycosides in advance.
According to a first aspect of the invention, a kind of soybean isoflavones product is provided, and it is made up of above-mentioned four kinds of isomer basically, and its purity is more than 50%, be meant that other isomer ignores, and based on the purity of four kinds of main isoflavones isomer D, De, G, the total amount meter of Ge.
According to a second aspect of the invention, a kind of preparation method of this soybean isoflavones is provided, degreasing product with soybean is a raw material, and this preparation method comprises that extracting raw material with methanol solution makes extracting solution, uses flocculation agent that this extracting solution is carried out flocculate and clarify and with the extracting solution after this clarification of polar macroporous adsorption resin separation and purification.
Method of the present invention is to extract isoflavones from soybean, and described raw material can comprise soybean, beans embryo or dregs of beans.If use soybean, beans embryo to make raw material, need carry out skimming treatment earlier.Can be raw material also, directly extract with the defatted soybean meal.
The optimized technical scheme according to the present invention, the preparation method of soybean isoflavones comprises following process:
(1) be that 65～78% methanol solution extracts raw material and makes extracting solution with concentration, extract 70～78 ℃ of temperature, extraction time 2-5 hour, concentrated extracting solution and reclaim methyl alcohol then;
(2) add flocculation agent, flocculate and clarify after said extracted liquid being diluted to the solution of total solids content≤20%;
(3) clear liquor is added in the adsorption column that is filled with polar macroporous adsorption resin;
(4) with 60～80% ethanolic soln desorbs.
The contriver finds in actually operating, traditional staticly settling separates the upper prop fractionation by adsorption that is unfavorable for concentrated solution, so the present invention requires to add flocculation agent before upper prop concentrated solution is carried out flocculate and clarify, flocculation agent can use this area flocculation agent commonly used, the wherein effective preferred gelatin of flocculation agent, chitin, amination chitin (or claiming JA finings), the purpose that adds flocculation agent mainly is in order to remove the impurity such as protein in the solution, guarantee that the effective constituent in the extracting solution is fully adsorbed by resin by adsorption column the time.Flocculation agent can use according to a conventional method, but preferably before use it is made into 1～2% solution, and above-mentioned extraction concentrated solution is suitably diluted (using deionized water usually) back add flocculation agent, to impose during interpolation at a slow speed and stir, leave standstill after interpolation finishes and to reach clarifying requirement in 2-4 hour, the addition of flocculation agent can determine that preferably making the concentration of this flocculation agent in extracting solution is 200～400ppm according to ordinary method or by test.
Supernatant liquor behind the flocculate and clarify is upper prop directly, also can be to wherein adding ethanol, and make the concentration of ethanol in clear liquor be not more than 10%, promptly with the clear liquor upper prop that contains 0-10% ethanol (industrial alcohol).
The screening of polar macroporous adsorption resin is the key point that realizes the object of the invention, the present invention's process is to low-pole, polar is multiple to be applicable to that test that the resinoid absorption of separating and purifying flavone frees characteristic relatively, finally be defined as polar macroporous adsorption resin, especially filter out the special efficacy polar macroporous adsorption resin of a class with the crosslinked more upward function of polystyrene polarization group, increased avidity to soybean isoflavones, the particularly described four kinds of main ingredients of isoflavones component in the material can fully be adsorbed, can only the flush away oligosaccharides in water washing process, impurity such as pigment, and when desorb, can escape to greatest extent, thereby guaranteed the purity of the finished product.According to contriver's The selection result, the polymeric adsorbent that polystyrene and amide group are cross-linked to form has extraordinary effect, and specific examples comprises that the label that Nankai University produces is the products such as macroporous adsorbent resin of ADS-5, ADS-17, ADS-7.
Be used for the solution that carries out desorb behind the upper prop, generally use ethanol, preferred 60～80% ethanol.The optimized technical scheme according to the present invention, clear liquor upper prop and during with the ethanolic soln desorb, speed control 1-3 times of column volume/hour.With before the alcohol desorption, wash with water earlier, to remove impurity such as wherein oligosaccharides, pigment, use alcohol desorption then, ethanol and part moisture are removed in the stripping liquid evaporation of collecting, then through concentrate drying, the preferred vacuum concentration drying that adopts can obtain final isoflavones product.
Remove the above, other related operation in the process of implementing the inventive method, the for example separation of filter residue in extracting solution or the clear liquor, can adopt centrifugation, also can direct filtration (vacuum filtration etc.), the concrete operations of upper prop and desorption process belong to the basic skills of this area, and the organic solvent that relates to reclaims and material concentrated etc., all can adopt conventional normal pressure or decompression operation or other feasible operation, these do not belong to category of the present invention, and the present invention also is not particularly limited.
The contriver adopts also that isoflavone content has carried out the qualitative and quantitative analysis detection in the product that the HPLC method obtains the inventive method, from the peak figure that obtains as can be seen, the assorted peak of each sample of the present invention all seldom, peak figure contrast with standard specimen, wherein mainly be the peak (seeing Fig. 2,4,5) of D, De, G, four isomer of Ge as can be known, other isomer is ignored, and only with the cubage of these four kinds of isomer, surpasses 50%.As a comparison, Fig. 6 be with the extracting solution of dregs of beans through concentrate, the HPLC spectrogram of the isoflavones product of general method preparation such as precipitation, because though instrument and adsorption column different make appearance time difference in the test, but visible assorted peak is numerous from collection of illustrative plates, and as can be known the purity of its finished product (four kinds of main components) less than 30%.
Can confirm from detected result, because the present invention has used narrow spectrum polymeric adsorbent, phenolic hydroxyl group in Polarization of Helper T Lymphocytes group in the resin such as amide group and the isoflavones molecule forms hydrogen bond (and the absorption that is different from prior art relies on intermolecular Van der Waals force), reach the purpose of specific adsorption, thereby can be when cleaning many impurity flush awaies, make the foreign matter content in the stripping liquid be reduced to minimum, improved the stripping liquid purity of isoflavones in the product after drying greatly, be embodied in the detected result is exactly to mix the peak seldom, mainly be D, De, G, the peak of four isomer of Ge, and can draw from spectrum analysis, other isomer is ignored, only four kinds of main isomer D, De, G, the total amount of Ge surpasses 50%.
In sum, the present invention successfully screens and has used special efficacy polar macroporous adsorption resin separation and purification isoflavones from soybean and soybean prod, simultaneously by extracting, separate, concentrate, clarify determining of top condition in each process procedure, success realizes a step adsorption-desorption purifying of soybean isoflavones, prepare the purity calculated with main component up to 50% soybean isoflavones product, usually the yield of product greater than 0.4% (because of what of isoflavone content in the raw material different), promptly 1 kilogram of soy material can be produced more than 4 grams, purity is greater than 50% soybean isoflavones product, accomplished the raising raw material availability, reduce production costs, and technology is simple, be easy to control, constant product quality, the active constituent content height, for suitability for industrialized production provides possibility, so enforcement of the present invention is to utilizing soybean isoflavones, develop the development of serial anti-cancer agent and protective foods and will play huge pushing effect, to promoting soybean action programme, promote the soybean comprehensive utilization to play active effect, for new field has been opened up in the deep processing of soybean.
Description of drawings
Fig. 1 is a preparation method's of the present invention process flow diagram.
Fig. 2 is that embodiment 1 separates the HPLC peak figure for preparing the isoflavones product from dregs of beans.
Fig. 3 is the HPLC peak figure of D, De, G, four kinds of isomer standard models of Ge.
Fig. 4 is the HPLC peak figure of the isoflavones product sample prepared of embodiment 1 and standard specimen stack test.
Fig. 5 is that embodiment 3 separates the HPLC peak figure for preparing the isoflavones product from the beans embryo.
Fig. 6 adopts the HPLC peak figure that makes without the isolating product of adsorption column of the present invention.
Embodiment
Further describe the present invention below by embodiment, but should not constitute any restriction practical range of the present invention.
Embodiment 1
Get the 1kg defatted soybean meal, add 12kg 70% methyl alcohol, reflux extraction is 2 hours in 78 ℃ of water-baths, centrifugation (3800rpm * 10min), get supernatant liquor and evaporate recovery methyl alcohol in Rotary Evaporators, make solution concentration become approximate paste, be diluted to the wherein about 15-20% of solid content with deionized water, stirring adds 1% gelatin solution simultaneously as flocculation agent, and the ultimate density that makes flocculation agent is 400ppm, left standstill then 2～3 hours, and made its clarification.Get supernatant liquor and add industrial alcohol and be made into and contain the 10% alcoholic acid aqueous solution, upper prop, the upper prop speed control is 2 times of column volumes per hour, the macroporous adsorbent resin ADS-5 that the filling polystyrene is cross-linked in the used adsorption column (polar resin, Nankai University's production).Use earlier the washed with de-ionized water post then, use 60% ethanolic soln desorb again, desorption rate be 2.5 times of column volumes/hour, collect stripping liquid and on Rotary Evaporators, evaporate ethanol and part moisture, adopt vacuum concentration to carry out drying at last, pulverize, get the former powder 4.23g of soybean isoflavones, it is 51% that quantitative assay goes out its purity.
For to the said products composition and purity make definite, at first make HPLC peak figure respectively with standard specimen and the said products sample of these four kinds of isomer, see Fig. 2 and Fig. 3, wherein De and Ge adopt the SILVER REAGENT standard specimen that U.S. Sigma company provides, the SILVER REAGENT standard specimen that D and G adopt Japan internationality farming research center to provide.And then with the product sample of this standard specimen and present embodiment preparation sample introduction simultaneously, the test that promptly superposes the results are shown in Figure 4 peak figure.
Measuring method:
Successively with the methanol extraction liquid of sample behind 0.45 μ m micro-filtration, respectively get a certain amount of solution and inject anti-phase chemical bond zygostyle, through and standard specimen relatively, qualitative according to the retention time of standard specimen, according to the peak area quantification of standard specimen.This quantitative detecting method can referring to contriver's research report (be published in " food and fermentation industries ", the fifth phase in 2000, P7).
Key instrument:
High pressure liquid chromatograph (day island proper Tianjin LC-6A)
UV-detector: SPD-6AV
Central control unit: SLC-6A
Chromatograph box: CTO-6A
Data processing equipment: C-R3A
Superpure water machine: Milli-Q50
Chromatographic condition:
Chromatographic column: Shim-pack clc-ods carbon 18 posts 0.15m * 6.0mm Φ
Moving phase: methyl alcohol: 5% acetate=30: 70
Flow velocity: 1.0ml/min (before 8.5 minutes); (1.5ml/min after 8.5 minutes)
Wavelength: 254nm
Detection sensitivity: 0.08AUFS
Column temperature: 50 ℃
Sample size: 10 μ l
Chart speed: 0.2cm/min
Relatively each peak figure can see that four essentially identical peaks of appearance time are respectively arranged among Fig. 3 and Fig. 2, and see from Fig. 4, these four main peaks are superimposed fully, prove that thus the isoflavones in the product of the present invention should be made up of these four kinds of main components, and its content is 51% as calculated.
Embodiment 2
Get the whole soybean of 1kg, pulverize, cross behind 40 mesh sieves with normal hexane degreasing (can use apparatus,Soxhlet's).With the reflux extraction 3 hours in 75 ℃ water-bath of 11kg 75% methanol solution, filter with the decompress filter method then, remove filter residue, filtrate is concentrated into paste in Rotary Evaporators, and reclaims methyl alcohol simultaneously.Concentrated solution is diluted to the wherein about 15-20% of solid content, adding 2% gelatin solution to the concentration of gelatin then while stirring is 400ppm, leave standstill and made its flocculate and clarify in 2 hours, getting supernatant liquor adds industrial alcohol and is made into 5% alcoholic solution, upper prop, the upper prop speed control is 1 times of column volume per hour, dress ADS-17 macroporous adsorbent resin (polar resin, Nankai University produces) in the post.After washed with de-ionized water, with 75% ethanolic soln desorb, desorption rate be 2 times of column volumes/hour, the stripping liquid of collecting is condensed into the underflow shape, reclaim ethanol simultaneously,, pulverize then with the concentrated solution drying, obtain the former powder of 3.81g isoflavones, detection method is with embodiment 1, and product purity is 52%.
Get 1kg beans embryo, pulverize, cross 40 mesh sieves, use the normal hexane degreasing, the reflux extraction 4 hours in 75 ℃ water-bath of the methanol solution of using 12kg 78% then, with the extracting solution centrifugation, get supernatant liquor concentrating under reduced pressure in Rotary Evaporators, reclaim methyl alcohol, get concentrated solution and be diluted to solid content about 20% with deionized water, add 1% chitin solution, add-on reaches 300ppm for its concentration in concentrated solution, and the limit edged stirs, and makes impurity flocculation sediments such as protein wherein, leave standstill after 3 hours and get the supernatant liquor upper prop, the upper prop speed control is 2 times of column volumes per hour, dress polar macroporous adsorption resin ADS-7 (Nankai University's productions) in the post, impurity such as usefulness deionized water flush away sugar, use 80% ethanolic soln desorb then, desorption rate be 1 times of column volume/hour, obtain former powder 20.01 grams of isoflavones after collecting the stripping workshop concentrate drying, the product color atlas is seen Fig. 5, detection method is with embodiment 1, D, De, G, the total purity of Ge is 50.5%.
Embodiment 4
Get the 1kg defatted soybean meal, with the reflux extraction 5 hours in 75 ℃ of water-baths of the methanol solution of 14kg 65%, the extraction liquid suction filtration separates removes residue, get supernatant liquor concentrating under reduced pressure in Rotary Evaporators, reclaim methyl alcohol, after getting the concentrated solution dilution, in solution, add the 2%JA finings, stir gently, leave standstill 2 hours after, get the supernatant liquor upper prop, dress macroporous adsorbent resin ADS-7 (polar resin in the post, Nankai University produces), the upper prop speed control is 2 times of column volumes per hour, uses impurity such as pure water flush away carbohydrate then, use 70% alcohol desorption, desorption rate is 1.5 times of column volumes per hour, collect stripping liquid, obtain behind the concentrate drying 4.01g after testing purity be 48.5% the former powder of soybean isoflavones (detection method with
Embodiment 1).
Embodiment 5
Get the 1kg defatted soybean meal, with the reflux extraction 3 hours in 75 ℃ water-bath of the methanol solution of 12kg 75%, the extraction liquid centrifugation (3800r.p.m * 10min), get supernatant liquor Rotary Evaporators concentrating under reduced pressure, thin up becomes solid content 20% then, add 2% chitin solution as flocculation agent, finish the back process by the narration of embodiment 4,4.0g purity is 49.95% the former powder of soybean isoflavones (detection method is with embodiment 1).
Embodiment 6
Get the 1kg soybean, pulverize, cross 40 mesh sieves, after the normal hexane degreasing, with the reflux extraction 4 hours in 75 ℃ of water-baths of the methanol solution of 13kg 65%, centrifugation (3800r.p.m * 10min), get supernatant liquor and be evaporated to paste, reclaim methyl alcohol simultaneously with Rotary Evaporators.After the concentrated solution thin up becomes solid content 20%, JA finings flocculate and clarify with 2%, get supernatant adding ethanol and be made into 10% ethanolic soln upper prop, upper prop speed is 3 times of column volumes per hour, macroporous adsorbent resin ADS-5 (polar resin, Nankai University produces) is housed, in the post after washed with de-ionized water, add 65% ethanolic soln desorb, collect behind the stripping liquid concentrate drying to such an extent that 3.5g purity is 50.5% the former powder of soybean isoflavones (detection method is with example 1).
Claims (10)
1, soybean isoflavones goods, it is made up of daidzin, daidzein, Genistoside and genistein basically from the extract of soybean or soybean degreasing raw material, is more than 50% in the purity of these four kinds of isomer composition total amounts.
2, the preparation method of soybean isoflavones, degreasing product with soybean is a raw material, and this preparation method comprises that extracting raw material with methanol solution makes extracting solution, uses flocculation agent that this extracting solution is carried out flocculate and clarify and with the extracting solution after this clarification of polar macroporous adsorption resin separation and purification.
3, the described preparation method of claim 2, it comprises following process:
(1) be that 65～78% methanol solution extracts raw material and makes extracting solution with concentration, extract 70～78 ℃ of temperature, extraction time 2-5 hour, concentrated extracting solution and reclaim methyl alcohol then;
(2) said extracted liquid adds flocculation agent, flocculate and clarify after being diluted to the solution of total solids content≤20%;
(3) clear liquor is added in the adsorption column that is filled with polar macroporous adsorption resin;
(4) with 60～80% ethanolic soln desorbs.
4, the described preparation method of claim 3, wherein, used flocculation agent comprises gelatin, chitin, amination chitin.
5, claim 3 or 4 described preparation methods, during flocculate and clarify, flocculation agent is made into 1～2% solution adding, and making the concentration of this flocculation agent in extracting solution is 200～400ppm.
6, claim 2 or 3 described preparation methods, wherein, described polar macroporous adsorption resin is polystyrene and the crosslinked resin of function polarization group.
7, the described preparation method of claim 6, wherein, this polar macroporous adsorption resin is the crosslinked resin of polystyrene and amide group.
8, the described preparation method of claim 3, wherein, the speed of upper prop and desorb be 1-3 times of column volume/hour.
9, claim 2 or 3 described preparation methods, wherein, raw materials used is defatted soybean meal.
10, claim 2 or 3 described preparation methods, wherein, raw materials used is the degreasing product of soybean or beans embryo.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100554226C (en) * | 2006-04-20 | 2009-10-28 | 山东省医学科学院药物研究所 | The preparation method of the Herba Trifolii Pratentis extract of tool estrogen activity |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100409851C (en) * | 2003-04-24 | 2008-08-13 | 沈阳药科大学 | Soy daidzin composition and preparation process and use thereof |
| CN100371341C (en) * | 2006-07-17 | 2008-02-27 | 北京宝泰宁堂生物技术有限公司 | Use of dextrose-delta-lactone as flocculant for obtaining isoflavone precipitation |
| CN102397317A (en) * | 2010-09-16 | 2012-04-04 | 长春大学 | Method for producing soybean Genistin and application of soybean Genistin in preparation of estrogenic drugs or female health food |
| CN106964324B (en) * | 2017-04-05 | 2019-10-15 | 牡丹江医学院 | A kind of isoflavones isolates and purifies the preparation method with macroporous absorbent resin |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100554226C (en) * | 2006-04-20 | 2009-10-28 | 山东省医学科学院药物研究所 | The preparation method of the Herba Trifolii Pratentis extract of tool estrogen activity |
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