CN1869660A - Method for deciding hydrolyzation or not or hydrolyzation degree of soybean isoflavone glucoside - Google Patents
Method for deciding hydrolyzation or not or hydrolyzation degree of soybean isoflavone glucoside Download PDFInfo
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Abstract
The invention relates to a method for judging whether soy bean isoflavone indicant has been hydrolyzed and the hydrolysis degree, making alcoholic extraction on market bean pulp, pumping extractive and filtering out impurities, vacuum-distilling and concentrating to fully eliminate alcohol and obtaining water phase, using water phase as substrate for hydrolyzing, extracting soy bean isoflavone glucoside from hydrolyzate by ethyl acetate, vacuum-concentrating extractive, making thin layer chromatography on concentrated phase, and observing chromatography result under UV lamp and judging whether soy bean isoflavone indicant is hydrolyzed and the hydrolysis degree. And it is quick and accurate.
Description
One, technical field
The present invention relates to a kind of whether method of hydrolysis or hydrolysis degree of soybean isoflavone glucoside of judging, especially be substrate when carrying out acid hydrolysis or microbial conversion with soybean soya-bean cake, dregs of beans or with their crude extract, can judge the whether method of hydrolysis or hydrolysis degree of soybean isoflavone glucoside fast, accurately, easily.And related to a kind of method that screening can enzymatic hydrolysis of soybean isoflavone glucoside bacterial classification quickly and efficiently.
Two, background technology
Isoflavones is a class secondary metabolite that forms in the legume growth courses such as soybean, has different physiological roles, and it not only participates in regulating the vegetative activity of plant, can also bring into play useful physiological regulatory action to human body.For isoflavones, the molecular structure of natural nucleoside is not the optimum condition of active performance, generally believes that aglycon is only the optimum condition of active performance.Yet in soybean, isoflavones mainly exists with genistein, daidzin and daidzin glucosides form, and the content of aglycon genistein, daidzein and the Daidzein of their correspondences seldom.In order to obtain the high isoflavone genin of biologically active, industrial be substrate with soybean soya-bean cake or dregs of beans mostly, adopt the method for acid hydrolysis or microbial conversion that glucosides is converted into aglycon.Judge soybean isoflavone glucoside whether hydrolysis or hydrolysis degree, normally judge by the variation of aglycon content before and after the hydrolysis.Yet the method process is relatively loaded down with trivial details.
Three, summary of the invention
The object of the invention provides a kind of whether method of hydrolysis or hydrolysis degree of soybean isoflavone glucoside of judging, this method is quick, easy, accurate, be that the sample that will obtain after the hydrolysis is through thin-layer chromatography, by observe having or not or strong and weakly judging the whether degree of hydrolysis or hydrolysis of soybean isoflavone glucoside of the 3rd fluorescent spot fluorescence on the silica gel plate under uviol lamp.
The present invention judge soybean isoflavone glucoside whether the method for hydrolysis or hydrolysis degree comprise the commodity dregs of beans through alcohol extract, the removal of impurity of extract suction filtration, decompression distillation be concentrated into no ethanol get water, with the water be substrate be hydrolyzed, with ethyl acetate from hydrolyzate extracting soybean isoflavone aglycon, extract concentrating under reduced pressure, concentrate and carry out thin-layer chromatography mutually, under uviol lamp, observe tomographic results and judge the whether degree of hydrolysis or hydrolysis of soybean isoflavone glucoside, it is characterized in that:
Commodity dregs of beans of the present invention is through 30～80% alcohol extract, and wherein ethanol volume (mL) is 2: 1 to 10: 1 with the ratio of dregs of beans weight (g), extracts 20～40 ℃ of temperature, ultrasonic Extraction 30～120 minutes.
The present invention removes solid matter in the ethanol extract with the vacuum pump suction filtration, the ethanol phase.
Concentrating under reduced pressure of the present invention is to concentrate with distillation under vacuum, and temperature is 50～70 ℃, is concentrated into no ethanol, obtains water.
The present invention is that substrate is hydrolyzed with the water, be (as hydrolysis 0.5～2.0h) or (containing in the nutrient culture media of 5～10% defatted soybean meals, pH=4.0～8.0 in 30～100 ℃ of water-baths such as the hydrochloric acid of 1～2moL/L or the sulfuric acid of 0.5～1.0moL/L with acid hydrolysis with the microbial conversion that can produce beta-glycosidase, temperature is under 28～30 ℃ of conditions, 150～300r/min, shake-flask culture).
The present invention is earlier hydrolyzate to be transferred pH to 4～5 with ethyl acetate extracting soybean isoflavone aglycon from hydrolyzate, uses the long-pending ethyl acetate extraction of hydrolyzate monoploid three times, the combined ethyl acetate phase, and decompression distillation concentrates.
The present invention carries out thin-layer chromatography mutually to concentrating, and is at GF
254On the silica gel plate, with volume ratio toluene: chloroform: acetone=4: 1.8: 1.8 is that developping agent carries out chromatography mutually to concentrating.
The present invention observes under uviol lamp and concentrates with the GF behind the above-mentioned developping agent chromatography
254Silica gel plate, find that blank sample, enzymolysis sample and sour water desampling are all having two fluorescent spots to occur with standard items genistein and standard items daidzein development distance same position place, the 3rd fluorescent spot also appearred in the sour water desampling except above-mentioned two fluorescent spots, and the appearance that the enzymolysis sample has behind thin-layer chromatography not occurring of having of the 3rd fluorescent spot.
The present invention carries out qualitative analysis to the 3rd fluorescent spot, at first sweeps on the silica gel plate silica gel of observed the 3rd fluorescent spot position under uviol lamp, with analytically pure methanol-eluted fractions silica gel, centrifugal and concentrated methyl alcohol mutually sample.The sample that takes a morsel is used for HPLC-PDA to be analyzed, by it three dimensional chromatogram as can be known, it has at the ultraviolet region end and absorbs and be that 205nm place has absorption maximum at wavelength, this conforms to the smart pure chromatogram feature of the soybean of having reported, soybean essence alcohol is steroidal class material.The sample that takes a morsel carries out the Liebermann-Burchard reaction, is reacted into the positive, and proving has the steroidal mother nucleus structure to exist in the sample.The sample that takes a morsel carries out HPLC-MS to be analyzed, and the base peak of ESI/MS (+) is 496.9 (M+Na), 480.9 (M+Na), and corresponding molecular weight is 473.9,457.9 corresponding with the molecular weight of smart pure A of soybean and the smart pure B of soybean respectively.Can determine that by above analysis the 3rd fluorescent spot is the smart alcohol of soybean.
The present invention measured respectively blank sample, sour water desampling (in the different time with the acid hydrolysis soybean isoflavone glucoside of concentration or in the identical time with the acid hydrolysis soybean isoflavone glucoside of variable concentrations), the content of genistein and daidzein in the enzymolysis sample (can produce the microbial conversion of beta-glycosidase), be with blank sample, sour water desampling and enzymolysis sample behind the said method chromatography, at GF
254Scrape the silica gel of getting with standard items genistein and standard items daidzein development distance same position place on the silica gel plate respectively, use methanol-eluted fractions silica gel, centrifugal and concentrated methyl alcohol obtains genistein sample and daidzein sample, use ultraviolet-visible spectrophotometer to measure genistein and determine the content of genistein then, at λ=254nm place mensuration daidzein and determine the content of daidzein according to its typical curve according to its typical curve at λ=263nm place.The 3rd fluorescent spot do not appear in blank sample behind thin-layer chromatography, the sour water desampling has the 3rd fluorescent spot to occur behind thin-layer chromatography, and the appearance that the enzymolysis sample has behind thin-layer chromatography not occurring of having of the 3rd fluorescent spot, and the content (being recorded by said method) of daidzein and genistein is also high more in strong more its pairing sample of fluorescence of the 3rd fluorescent spot occurring after thin layer of sample.From the above, by sample the having or not or strong and weak can judge the whether degree of hydrolysis or hydrolysis of soybean isoflavone glucoside of the 3rd fluorescent spot fluorescence on silica gel plate behind the thin-layer chromatography.
The present invention has the following advantages:
1,, avoided measuring the complicated processes of isoflavone genin content before and after the hydrolysis by under uviol lamp, observing having or not or strong and weakly can judging the whether degree of hydrolysis or hydrolysis of soybean isoflavone glucoside quickly and accurately of the 3rd fluorescent spot fluorescence on the silica gel plate.
2, this invention for screening can the enzymatic hydrolysis of soybean isoflavone glucoside bacterial classification method fast and accurately is provided.
3, can detect with soybean soya-bean cake or dregs of beans with this inventive method is whether the soybean function food of feedstock production or the pre-treatment process of health products make the content of bioactivator-isoflavone genin increase.
Four, embodiment
Embodiment 1:
(1) with 1
#Black-koji mould (Aspegillus niger) SFII (Sichuan Food IndustryInstitute) 3.357,2
#Black-koji mould (Aspegillus niger) SFII 3.360,3
#Black-koji mould (Aspegillus niger) SFII 3.313,4
#Black-koji mould (Aspegillus niger) SFII M227, bacillus subtilis (Bacillus subtilis) SFII 10210, Java rhizopus (Rhizopus) SFII 03125 are respectively in the nutrient culture media that contains 8% defatted soybean meal, natural pH, temperature is under 28～30 ℃ of conditions, 200r/min, shake-flask culture 6 days.
(2) with 70% ethanol (ethanol volume (mL): dregs of beans weight (g)=6: 1), under 40 ℃ above-mentioned nutrient culture media after microbial fermentation is cultivated is being distinguished ultrasonic Extraction 40 minutes, suction filtration gets ethanol extract, it is evaporated to concentrate under 65 ℃ and does not contain ethanol and obtain water.
(3) use and the ethyl acetate extraction of water equal volume three times, combined ethyl acetate phase concentrating under reduced pressure obtains ethyl acetate and concentrates phase.
(4) at GF
254On the silica gel plate, with volume ratio toluene: chloroform: acetone=4: 1.8: 1.8 is that developping agent concentrates ethyl acetate and carries out thin-layer chromatography mutually.Under uviol lamp, observe to remove having or not or power of the 3rd fluorescent spot fluorescence the fluorescent spot with standard items genistein (Rf=6.3) and standard items daidzein (Rf=5.0) development distance same position place, and the method by mensuration genistein described in the summary of the invention and daidzein content records after microbial fermentation is cultivated the content of genistein and daidzein in each nutrient culture media, result such as table 1.
Table 1 content of genistein and daidzein in each nutrient culture media after microbial fermentation is cultivated
| Blank sample | Head mold | Bacillus subtilis | 4 #Black-koji mould | 3 #Black-koji mould | 2 #Black-koji mould | 1 #Black-koji mould | |
| Article three, fluorescent spot have or not or strong and weak every gram dregs of beans in the content (mg) of genistein | Do not have 0.206 | Do not have 0.276 | Do not have 0.280 | 4 0.385 | 3 0.423 | 2 0.598 | 1 1.700 |
| The content (mg) of daidzein in every gram dregs of beans | 0.134 | 0.208 | 0.226 | 0.302 | 0.378 | 0.497 | 0.560 |
Annotate: in the table fluorescence of the 3rd fluorescent spot of 1,2,3,4 expressions by by force to a little less than
By above result as can be known, along with the fluorescence of the 3rd fluorescent spot of increase of genistein and daidzein content also by not having to having, grow from weak to strong.Therefore, the hydrolysis sample through behind the thin-layer chromatography can by under uviol lamp, observe the 3rd fluorescent spot fluorescence on the silica gel plate have or not or strong and weak, judge the whether degree of hydrolysis or hydrolysis of soybean isoflavone glucoside quickly and accurately
Embodiment 2:
(1) take by weighing the 2.5g defatted soybean meal, (ethanol volume (mL): dregs of beans weight (g)=6: 1), 40 ℃ of following ultrasonic Extraction 40 minutes, suction filtration got ethanol extract to the ethanol with 70%.
(2) use 0.5,1.0 respectively, the hydrochloric acid of 2.0moL/L, the above-mentioned ethanol extract of hydrolysis obtains 1 in 80 ℃ of water-baths
#Hydrolysis sample, 2
#Hydrolysis sample and 3
#The hydrolysis sample.
(3) transfer pH to 4～5 of hydrolyzate with NaOH, use and the ethyl acetate extraction of each hydrolysis sample equal volume three times, combined ethyl acetate phase concentrating under reduced pressure, ethyl acetate concentrates phase.
(4) at GF
254On the chromatoplate, with volume ratio toluene: chloroform: acetone=4: 1.8: 1.8 is that developping agent concentrates ethyl acetate and carries out thin-layer chromatography mutually.Under uviol lamp, observe to remove having or not or power of the 3rd fluorescent spot fluorescence the fluorescent spot with standard items genistein (Rf=6.3) and standard items daidzein (Rf=5.0) development distance same position place, and the method by mensuration genistein described in the summary of the invention and daidzein content records the content of genistein and daidzein in each sour water desampling, result such as table 2.
Table 2 dregs of beans content of genistein and daidzein in each hydrolysis sample behind the hydrochloric acid hydrolysis of variable concentrations
| 1 #The hydrolysis sample | 2 #The hydrolysis sample | 3 #The hydrolysis sample | |
| Article three, fluorescent spot have or not or strong and weak every gram dregs of beans in the content of genistein, (mg) content of daidzein in every gram dregs of beans, (mg) | 3 1.362 0.198 | 2 2.988 0.266 | 1 3.027 0.634 |
Annotate: in the table fluorescence of the 3rd fluorescent spot of 1,2,3 expressions by by force to a little less than
By above result as can be known, along with the content of genistein and daidzein in the increase hydrolysis sample of concentration of hydrochloric acid is also increasing, and the fluorescence of pairing the 3rd fluorescent spot is also strong more.
Embodiment 3:
(1) take by weighing the 2.5g defatted soybean meal, with embodiment 2 (1) methods handle ethanol extract.
(2) with the hydrochloric acid of 2.0moL/L, the above-mentioned ethanol extract 0.5h of hydrolysis, 1.0h, 1.5h obtain 1 respectively in 80 ℃ of water-baths
#Hydrolysis sample, 2
#Hydrolysis sample and 3
#The hydrolysis sample.
(3) handle the hydrolysis sample with embodiment 2 (3) methods, get ethyl acetate and concentrate phase.
(4) obtain following result such as table 3 with embodiment 2 (4) methods.
Table 3 dregs of beans dyestuff in each hydrolysis sample through after with the hydrochloric acid hydrolysis different time of concentration
The content of lignin and daidzein
| 1 #The hydrolysis sample | 2 #The hydrolysis sample | 3 #The hydrolysis sample | |
| Article three, fluorescent spot have or not or strong and weak every gram dregs of beans in the content of genistein, (mg) content of daidzein in every gram dregs of beans, (mg) | 3 2.758 0.514 | 2 3.027 0.634 | 1 3.266 0.674 |
Annotate: in the table fluorescence of the 3rd fluorescent spot of 1,2,3 expressions by by force to a little less than
By above result as can be known, dregs of beans is through with the hydrochloric acid hydrolysis of concentration the time, and along with the content of genistein and daidzein in the increase hydrolysis sample of hydrolysis time is also increasing, and the fluorescence of pairing the 3rd fluorescent spot is also strong more.
Embodiment 4:
(1) take by weighing the 2.5g defatted soybean meal, with embodiment 2 (1) methods handle ethanol extract.
(2) use 0.25,0.5 respectively, the sulfuric acid of 1.0moL/L handles ethanol extract with embodiment 2 (2) methods and obtains 1
#Hydrolysis sample, 2
#Hydrolysis sample and 3
#The hydrolysis sample.
(3) handle the hydrolysis sample with embodiment 2 (3) methods, get ethyl acetate and concentrate phase.
(4) obtain following result such as table 4 with embodiment 2 (4) methods.
Table 4 dregs of beans behind the sulphuric acid hydrolysis of variable concentrations in each hydrolysis sample genistein and
The content of daidzein
| 1 #The hydrolysis sample | 2 #The hydrolysis sample | 3 #The hydrolysis sample | |
| Article three, fluorescent spot have or not or strong and weak every gram dregs of beans in the content (mg) of daidzein in the every gram dregs of beans of content (mg) of genistein | 3 1.370 0.210 | 2 2.976 0.264 | 1 3.121 0.641 |
Annotate: in the table fluorescence of the 3rd fluorescent spot of 1,2,3 expressions by by force to a little less than
By above result as can be known, along with the content of genistein and daidzein in the increase hydrolysis sample of sulfuric acid concentration is also increasing, and the fluorescence of pairing the 3rd fluorescent spot is also strong more.
Embodiment 5:
(1) take by weighing the 2.5g defatted soybean meal, with embodiment 2 (1) methods handle ethanol extract.
(2) with the sulfuric acid of 1.0moL/L with embodiment 3 (2) methods handle ethanol extract 0.5h, 1.0h respectively, 1.5h obtains 1
#Hydrolysis sample, 2
#Hydrolysis sample and 3
#The hydrolysis sample.
(3) handle the hydrolysis sample with embodiment 2 (3) methods, get ethyl acetate and concentrate phase.
(4) obtain following result such as table 5 with embodiment 2 (4) methods.
Table 5 dregs of beans dyewood in each hydrolysis sample through after with the sulphuric acid hydrolysis different time of concentration
The content of element and daidzein
| 1 #The hydrolysis sample | 2 #The hydrolysis sample | 3 #The hydrolysis sample | |
| Article three, fluorescent spot have or not or strong and weak every gram dregs of beans in the content of genistein, (mg) content of daidzein in every gram dregs of beans, (mg) | 3 2.768 0.512 | 2 3.014 0.629 | 1 3.216 0.675 |
Annotate: in the table fluorescence of the 3rd fluorescent spot of 1,2,3 expressions by by force to a little less than
By above result as can be known, dregs of beans is through with the sulphuric acid hydrolysis of concentration the time, and along with the content of genistein and daidzein in the increase hydrolysis sample of hydrolysis time is also increasing, and the fluorescence of pairing the 3rd fluorescent spot is also strong more.
Embodiment 6:
(1), will be raw material with the soya bean according to the Salt black bean of traditional handicraft preparation, 40～70 ℃ of oven dry down, be crushed into powder.
(2), get an amount of Salt black bean powder, with embodiment 1 (2) method handle water.
(3), handle water with embodiment 1 (3) method and obtain the concentrated phase of ethyl acetate.
(4), at GF
254On the silica gel plate, with volume ratio toluene: chloroform: acetone=4: 1.8: 1.8 is that developping agent concentrates ethyl acetate and carries out thin-layer chromatography mutually.Under uviol lamp, observe the 3rd fluorescent spot, and the content that records daidzein in the Salt black bean (0.525mg/g) and genistein (1.717mg/g) of the method by mensuration genistein described in the summary of the invention and daidzein content has increased than the content of daidzein in the soya bean (0.134mg/g) and genistein (0.206mg/g).
Embodiment 7:
1, gets the female element in a slice sky (isoflavones sheet), two female elements in sky, be crushed into powder respectively.
2, use 1～5mL ethyl acetate ultrasonic Extraction, 5～20min respectively, the centrifugal ethyl acetate phase that gets.
3, at GF
254On the silica gel plate, with volume ratio toluene: chloroform: acetone=4: 1.8: 1.8 is that developping agent carries out thin-layer chromatography mutually to ethyl acetate.The sample of observing under uviol lamp by the female element in a slice sky or two female plain preparations in sky all has the 3rd the fluorescent spot appearance and the latter's fluorescence stronger behind chromatography.
Claims (4)
1, a kind ofly judge the whether method of hydrolysis or hydrolysis degree of soybean isoflavone glucoside, it is characterized in that: the commodity dregs of beans through alcohol extract, the removal of impurity of extract suction filtration, decompression distillation be concentrated into no ethanol get water, with the water be substrate be hydrolyzed, with ethyl acetate from hydrolyzate extracting soybean isoflavone aglycon, extract concentrating under reduced pressure, concentrate and carry out thin-layer chromatography mutually, under uviol lamp, observe tomographic results and judge the whether degree of hydrolysis or hydrolysis of soybean isoflavone glucoside.
2, claim 1 is described judges the whether method of hydrolysis or hydrolysis degree of soybean isoflavone glucoside, and it is characterized in that: extracting with concentration of alcohol number percent is 30～80%, 20～40 ℃ of extraction temperature; Concentrating under reduced pressure is to concentrate with distillation under vacuum, and temperature is 50～70 ℃; Hydrolysis is with acid hydrolysis or with the microbial conversion that can produce beta-glycosidase; With ethyl acetate extracting soybean isoflavone aglycon from hydrolyzate, be earlier hydrolyzate to be transferred pH to 4～5, use the long-pending ethyl acetate extraction of hydrolyzate monoploid three times, the combined ethyl acetate phase.
3, claim 1 or 2 is describedly judged the whether method of hydrolysis or hydrolysis degree of soybean isoflavone glucoside, it is characterized in that: judge soybean isoflavone glucoside whether the degree of hydrolysis or hydrolysis be according to the 3rd fluorescent spot fluorescence having or not or strong and weak.
4, claim 1 or 2 is describedly judged the whether method of hydrolysis or hydrolysis degree of soybean isoflavone glucoside, and it is characterized in that: thin-layer chromatography adopts GF
254Silica gel plate, with volume ratio toluene: chloroform: acetone=4: 1.8: 1.8 is that developping agent is to concentrating phase.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103323557A (en) * | 2013-06-16 | 2013-09-25 | 中国科学院成都生物研究所 | Method for analyzing isoflavone in soybeans and products thereof |
| CN104725339A (en) * | 2015-03-30 | 2015-06-24 | 吉林化工学院 | Method for preparing soybean isoflavone aglucone by using acetic acid to catalyze hydrolysis of soybean isoflavone glycoside |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102783524A (en) * | 2012-08-08 | 2012-11-21 | 鲜活果汁工业（昆山）有限公司 | Preparation method and purpose of chalcone flavonol derivatives of black bean extracts |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE69921778T2 (en) * | 1998-01-12 | 2006-02-02 | Nichimo K.K. | PROCESS FOR PRODUCING ISOFLAVONE COMPOUNDS |
| CN1069903C (en) * | 1998-09-22 | 2001-08-22 | 北京市农林科学院畜牧兽医研究所 | Method for extracting isoflavone from soybean |
| CN1448394A (en) * | 2002-04-01 | 2003-10-15 | 阎子鹏 | Method for extracting soybean isoflavone from soya bean watse |
| WO2004043945A1 (en) * | 2002-11-12 | 2004-05-27 | Wiley Organics, Inc. | Method for purifying and separating soy isoflavones |
| CN1261586C (en) * | 2003-08-01 | 2006-06-28 | 金凤燮 | Method for preparing aglycon of soybean isoflavone glycoside base by enzymatic method hydrolyzing soybean |
| CN1584038A (en) * | 2003-08-22 | 2005-02-23 | 中国农业大学 | Biological conversion and extraction and purification of soy bean isoflavone |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103323557A (en) * | 2013-06-16 | 2013-09-25 | 中国科学院成都生物研究所 | Method for analyzing isoflavone in soybeans and products thereof |
| CN104725339A (en) * | 2015-03-30 | 2015-06-24 | 吉林化工学院 | Method for preparing soybean isoflavone aglucone by using acetic acid to catalyze hydrolysis of soybean isoflavone glycoside |
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