CN115044628B - Method for producing soybean isoflavone aglycone by whole cell transformation - Google Patents
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Abstract
The invention provides a method for producing soybean isoflavone aglycone by whole cell transformation, which comprises the following specific steps: inoculating the Aspergillus niger RAF106 conidium suspension into a transformation nutrient solution containing soybean isoflavone or one or more of daidzein, daidzein and genistin, and fermenting at 15-44 ℃ for 10-60 h. According to the invention, the Aspergillus niger RAF106 strain is used for producing the free soybean isoflavone aglycone by a whole cell transformation method, the high-efficiency transformation of the soybean isoflavone can be realized in 44 hours of fermentation, and the daidzin, the genistin and the daidzin can be completely transformed in 36 hours, so that the contents of the daidzein, the genistein and the glycitein are respectively improved by 17 times, 13.3 times and 10.5 times, and the product produced in 36 hours of transformation has the highest DPPH clearance capability.
Description
Technical Field
The invention belongs to the technical field of bioengineering and biochemistry, and particularly relates to a method for producing soybean isoflavone aglycone by whole cell transformation.
Background
Soy isoflavones are secondary metabolites of flavonoids produced by plants such as soybean or alfalfa, a typical phytoestrogen, with weak estrogenic activity. The soybean isoflavone can play a role in regulating estrogen-like or anti-hormone bi-directionally, has the activities of resisting oxidation, tumor, bacteria and the like, and is closely related to human health when being eaten deeply. However, the active components of soybean isoflavone mainly exist in the form of glycoside in a combined state, and the bioavailability is extremely low, which restricts the full utilization of the active components.
Research shows that intestinal flora can mediate biological transformation of combined soybean isoflavone glycoside to produce free soybean isoflavone aglycone, so as to obviously improve bioavailability and promote full play of the physiological activity of soybean isoflavone. In addition to bacteria, fungi can also transform the bound soy isoflavone glycoside to produce free soy isoflavone aglycone, such as the fermentation of soy foods by the rhizopus stolonifer increases the aglycone amount from 8.2mg/100g to 102.9mg/100g at 72 hours; penicillium citrinum is fermented in potato glucose broth rich in soybean isoflavone and soybean extract for 144 hr to produce genistein and daidzein with conversion rate up to 98.7%. Aspergillus niger is an important representative filamentous fungus, can produce numerous metabolites such as cellulase, amylase, pectase, tannase, citric acid, gluconic acid and the like, and is widely applied to industrial production, food fermentation and the like. Studies have reported that glycosidases produced by aspergillus niger are capable of converting bound soy isoflavone glycosides into free soy isoflavone aglycones. However, the cost of enzyme conversion is high, enzyme preparation is needed to be purchased or enzyme liquid is needed to be prepared, and the process is complex. In order to reduce the cost, the microbial whole cells can be directly adopted for biological transformation, for example, aspergillus niger is adopted for fermenting soybean powder, the genistein content can be improved by 4 times within 48 hours, but the generation of other free soybean isoflavone aglycones is not reported; aspergillus niger HG-35 assists Aspergillus oryzae HG-26 soy sauce mash to ferment greatly to improve the content of daidzein, glycitein and genistein, the time for complete conversion to generate free soybean isoflavone aglycone is 70-90 hours, the conversion time is long, and the conversion efficiency is low.
Therefore, searching other methods for producing free soybean isoflavone aglycone by whole-cell bioconversion of aspergillus niger with short transformation time and high transformation efficiency has quite a necessity for promoting the practical application of soybean isoflavone.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for producing soybean isoflavone aglycone by whole cell transformation, which improves the transformation efficiency of soybean isoflavone glycoside.
The invention aims at providing an application of Aspergillus niger RAF106 in preparing soybean isoflavone aglycone.
Another object of the present invention is to provide a method for producing soybean isoflavone aglycone by whole cell transformation.
The invention achieves the aim by the following technical means:
the invention provides an application of Aspergillus niger (Aspergillus niger) RAF106 in preparation of soybean isoflavone aglycone; the Aspergillus niger RAF106 is preserved in China general microbiological culture collection center (CGMCC) in 8 months and 27 days of 2014, the preservation number is CGMCC No.9608, and the preservation unit address is North Chen Xili No. 1 and 3 in the Korean region of Beijing city of China.
Specifically, the application is the application of Aspergillus niger RAF106 in the whole cell transformation of soybean isoflavone glycoside to produce soybean isoflavone aglycone.
The invention provides a method for producing soybean isoflavone aglycone by whole cell transformation, inoculating Aspergillus niger RAF106 conidium suspension into a transformation nutrient solution, and fermenting for 12-60 h at 15-42 ℃; the conversion nutrient solution contains one or more of soybean isoflavone or daidzein, daidzein and genistin.
Preferably, the conversion nutrient solution is potato dextrose liquid nutrient solution containing one or more of soybean isoflavone, daidzein and genistin.
More preferably, the conversion liquid is a potato dextrose liquid nutrient solution containing 0.1 to 20 mass percent of one or more of soybean isoflavone, daidzein, glycitin and genistin.
Preferably, the final concentration of Aspergillus niger RAF106 conidia in the post-inoculation transformed nutrient solution is 10 2 ～10 8 Individual spores/mL.
More preferably, the final concentration of the conidia is 10 6 Individual spores/mL.
Preferably, the fermentation temperature is 30 ℃.
Preferably, the fermentation time is 24 to 48 hours.
More preferably, the fermentation time is 36 hours.
Preferably, the fermentation is a shaking fermentation culture.
More preferably, the oscillation is achieved by a shaker.
More preferably, the rotation speed of the shaking table is 100-220 rpm/min.
Most preferably, the shaking table rotation speed is 200rpm/min.
The invention has the following beneficial effects:
according to the invention, the Aspergillus niger RAF106 strain is used for producing the free soybean isoflavone aglycone by a whole cell transformation method, the high-efficiency transformation of the soybean isoflavone can be realized in 24 hours of fermentation, and the daidzin, the genistin and the daidzin can be completely transformed in 36 hours, so that the contents of the daidzein, the genistein and the glycitein are respectively improved by 17 times, 13.3 times and 10.5 times, and the product produced in 36 hours of transformation has the highest DPPH clearance capability.
Drawings
FIG. 1 is a graph showing the change in daidzein content of example 1 by whole cell transformation of daidzein with A.niger RAF 106.
FIG. 2 is a graph showing the change in genistein production by whole cell transformation of genistin with A.niger RAF106 in example 1.
FIG. 3 is a graph showing the change in glycitein production by whole cell transformation of daidzein with A.niger RAF106 in example 1.
FIG. 4 is a graph showing the change in soybean isoflavone aglycone content obtained by whole cell transformation of soybean isoflavone with Aspergillus niger RAF106 in example 2; wherein, the graph A is the experimental result of the experimental group A; panel B shows the results of experiment B.
FIG. 5 is a graph showing the change in soybean isoflavone aglycone content obtained by whole cell transformation of soybean isoflavone with Aspergillus niger RAF106 in example 3; wherein, the graph A is the experimental result of the experimental group C; panel B shows the results of experiment set D.
FIG. 6 is a graph showing the change in the amount of daidzein produced by whole cell transformation of high concentration of conjugated daidzein by Aspergillus niger RAF106 in example 4
FIG. 7 is a graph showing the DPPH radical scavenging ability of Aspergillus niger RAF106 transformed into soybean isoflavone aglycone in example 5.
Detailed Description
The invention is further illustrated in the following drawings and specific examples, which are not intended to limit the invention in any way. Unless specifically stated otherwise, the reagents, methods and apparatus employed in the present invention are those conventional in the art.
Reagents and materials used in the following examples are commercially available unless otherwise specified.
The Aspergillus niger RAF106 strain used in the invention has a preservation date of 2014, 8 and 27 days, a preservation number of CGMCC NO.9608 and a preservation unit of China general microbiological culture Collection center (CGMCC); the preservation unit address is North Chen West Lu No. 1 and No. 3 in the Chaoyang area of Beijing city of China.
The preparation method of the whole cell transformed nutrient solution comprises the following steps: mixing potato 200g, sucrose 20g and distilled water 1L, sterilizing at 121deg.C for 20min at natural pH; cooling, and adding 10% soybean isoflavone.
The preparation method of the seed culture medium of the Aspergillus niger RAF106 strain comprises the following steps: mixing potato 200g, sucrose 20g, agar 20g and distilled water 1L, sterilizing at 121deg.C for 20 min.
Soy isoflavones (BR, 40%) were purchased from shanghai source leaf biotechnology limited.
Standard substances (more than or equal to 98%) such as daidzin, daidzein, genistin, daidzein, glycitein, genistein and the like are all purchased from Shanghai source leaf biotechnology limited company.
Methanol (chromatographic purity), acetonitrile (chromatographic purity) were all purchased from sammer feishier technologies.
EXAMPLE 1 Aspergillus niger whole cell transformation of bound soy isoflavone glycoside to its free aglycone
1. Method of
(1) Seed culture of A.niger RAF106 strain: the seed medium of the Aspergillus niger RAF106 strain prepared as described above was used for stationary culture in an eggplant flask at 30℃for 5d.
(2) Acquisition of spore suspension of A.niger RAF106 strain: washing the solid plate culture medium full of Aspergillus niger spores with sterile water containing 0.05% Tween-80, and scraping the surface of the culture medium with a pipette tip to obtain Aspergillus niger conidium suspension.
(3) Adding Aspergillus niger RAF106 conidium suspension into the whole cell transformation nutrient solution to make the final concentration of conidium after inoculation 10 6 The culture temperature of spores per mL is 30 ℃, the rotation speed of a shaking table is 200rpm/min, and fermentation is carried out for 60h.
(4) The conversion product of soybean isoflavone was taken out every 12 hours, and Aspergillus niger mycelia were removed and filtered using a 0.22 μm filter membrane. And then detecting the content of the converted soybean isoflavone glycoside and aglycone substance by using a high performance liquid chromatography. The detection conditions of the high performance liquid chromatography are as follows: mobile phase a:0.1% (V/V) acetic acid in water, B:100% pure methanol solution, C:100% pure acetonitrile solution; column temperature: 36 ℃; sample injection amount: 10. Mu.L; detection wavelength: 260nm; flow rate: 0.8mL/min. The gradient elution conditions are shown in Table 1.
TABLE 1 gradient elution conditions
2. Results
As shown in FIG. 1, the daidzein conversion test showed that daidzein was completely converted at 36 hours, and the daidzein content gradually increased with the conversion of daidzein, with the peak at 36 hours, and the daidzein content increased from the initial 0.001317mg/mL to 0.02239mg/mL by a factor of 17.
The results of the genistin conversion experiment are shown in fig. 2, the genistin is completely converted in 36h, the genistein content is gradually increased along with the conversion of the genistin, the peak is reached in 36h, the content is increased from the initial 0.0003040mg/mL to 0.004061mg/mL, and the content is increased by 13.3 times.
As shown in FIG. 3, the daidzein conversion test shows that daidzein is completely converted at 36h, the glycitein content gradually increases with the conversion of daidzein, the peak is reached at 36h, and the content increases from 0.002876mg/mL to 0.03023mg/mL by 10.5 times.
Example 2 Effect of different inoculum sizes on Aspergillus niger whole cell transformed conjugated soy isoflavone glycoside production of its free aglycone
Two experimental groups were set up:
experiment group a: final concentration of Aspergillus niger RAF106 conidium after inoculation is 10 2 Individual spores/mL;
experimental group B: final concentration of Aspergillus niger RAF106 conidium after inoculation is 10 8 Individual spores/mL;
the remaining conditions were the same: the culture temperature is 30 ℃, the rotation speed of a shaking table is 200rpm/min, and the fermentation is carried out for 60 hours.
The conversion products of soy isoflavones from both experimental groups were removed every 12h and Aspergillus niger hyphae were removed and filtered using a 0.22 μm filter. The content of the converted soybean isoflavone glycoside and aglycone substance was measured by high performance liquid chromatography under the same chromatographic conditions as in example 1.
The results are shown in FIG. 4, wherein A is the experimental result of experimental group A and B is the experimental result of experimental group B.
The results showed that when the final concentration of A.niger RAF106 conidia was 10 2 At the time of individual spores/mL, the soybean isoflavone glycoside is completely converted within 48 hours, and the content of free aglycone substance reaches the highest peak at 48 hours; when the final concentration of the Aspergillus niger RAF106 conidium is 10 8 At each spore/mL, the soybean isoflavone glycoside was completely converted within 36 hours, and the free aglycone material content reached the peak at 36 hours.
Example 3 Effect of different fermentation temperatures on Aspergillus niger Whole cell transformation of bound soy isoflavone glycoside to give its free aglycone
Two experimental groups were set up:
experiment group C: the culture temperatures are respectively 15 ℃;
experimental group D: the culture temperatures are 42 ℃ respectively;
other conditions were the same: black after inoculationFinal concentration of Aspergillus RAF106 conidium of 10 6 The rotation speed of the shaking table is 200rpm/min, and the fermentation is carried out for 60 hours.
The conversion products of soy isoflavones from both experimental groups were removed every 12h and Aspergillus niger hyphae were removed and filtered using a 0.22 μm filter. The content of the converted soybean isoflavone glycoside and aglycone substance was measured by high performance liquid chromatography under the same chromatographic conditions as in example 1.
The results are shown in FIG. 5, wherein FIG. A is the experimental result of experimental group C and FIG. B is the experimental result of experimental group D.
The results showed that the soybean isoflavone glycoside was completely converted in 48 hours at 15℃and the content of the free aglycone substance reached the maximum at 48 hours. At a culture temperature of 42 ℃, the soybean isoflavone glycoside is completely converted within 36 hours, and the content of the free aglycone substance reaches the highest peak at 36 hours.
EXAMPLE 4 Aspergillus niger whole cell transformation of high concentration of bound soy isoflavone glycoside to its free aglycone
Adding Aspergillus niger RAF106 conidium suspension into whole cell transformation nutrient solution containing 20% soybean isoflavone to make the concentration of conidium after inoculation 10 6 The culture temperature of spores per mL is 30 ℃, the rotation speed of a shaking table is 200rpm/min, and fermentation is carried out for 60h.
The conversion product of soybean isoflavone was taken out every 12 hours, and Aspergillus niger mycelia were removed and filtered using a 0.22 μm filter membrane. The content of the converted soybean isoflavone glycoside and aglycone substance was measured by high performance liquid chromatography under the same chromatographic conditions as in example 1.
As a result, as shown in FIG. 6, at a soybean isoflavone concentration of 20%, the soybean isoflavone glycoside was completely converted within 48 hours, and the content of the free aglycone substance reached the maximum at 48 hours.
EXAMPLE 5 DPPH radical scavenging ability test of soybean isoflavone conversion products
1. Experimental materials
(1) In the transformation experiment of example 1, the transformed fermentation broth was taken out every 12 hours and diluted 100-fold with sterile water for use.
(2) DPPH-ethanol solution: 20mg of DPPH reagent is weighed into a beaker, dissolved in absolute ethyl alcohol, and then stored in a 250mL volumetric flask for constant volume and light protection.
2. Experimental method
(1) Respectively sucking 2mL of diluted fermentation liquor into a test tube, adding 2mL of DPPH-ethanol solution, standing at room temperature and dark place for reaction for 30min, measuring absorbance at 517nm wavelength, and marking as A i 。
(2) Respectively sucking 2mL of absolute ethyl alcohol into a test tube, adding 2mL of DPPH-ethanol solution, standing at room temperature in the dark for 30min for reaction, measuring absorbance at 517nm wavelength, and recording as A 0 。
(3) Respectively sucking 2mL of diluted fermentation liquor into a test tube, adding 2mL of absolute ethyl alcohol, standing at room temperature in the dark for reaction for 30min, measuring absorbance at 517nm wavelength, and marking as A r (blank control).
Each experiment was repeated 3 times, the absorbance values were averaged 3 times, and DPPH radical scavenging rate (K) was calculated according to the following formula.
As shown in the experimental result in figure 7, when the conversion time is 36 hours, the DPPH free radical clearance of the fermentation broth after conversion reaches the highest (p is less than 0.05) and is 4.8 times of that of the non-converted soybean isoflavone, which indicates that DPPH free radical clearance is effectively improved after the soybean isoflavone is converted by the whole cells of the aspergillus niger, and the fermentation broth has good antioxidation effect.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (10)
1. The application of Aspergillus niger (Aspergillus niger) RAF106 in the preparation of soybean isoflavone aglycone is characterized in that the Aspergillus niger RAF106 is preserved in China general microbiological culture collection center (CGMCC) with the preservation number of CGMCC No.9608 in the 8 th month of 2014 and the 27 th day.
2. A method for producing soybean isoflavone aglycone by whole cell transformation, which is characterized in that the aspergillus niger RAF106 conidium suspension in claim 1 is inoculated into a transformation nutrient solution and fermented for 12 to 60 hours at 15 to 42 ℃; the conversion nutrient solution contains one or more of daidzin, daidzein or genistin.
3. The method according to claim 2, wherein the final concentration of the conidia of Aspergillus niger RAF106 in the post-inoculation transformed nutrient solution is 10 2 ～10 8 Individual spores/mL.
4. A method according to claim 3, wherein the final concentration of conidia is 10 6 Individual spores/mL.
5. The method of claim 2, wherein the conversion nutrient solution is a potato dextrose liquid nutrient solution containing one or more of daidzein, glycitin, or genistin.
6. The method according to claim 2 or 5, wherein the mass percentage of daidzein, glycitin or genistin is 0.1-20%.
7. The method of claim 2, wherein the fermentation temperature is 30 ℃.
8. The method according to claim 2, wherein the fermentation time is 24 to 48 hours.
9. The method according to any one of claims 2 or 5, wherein the fermentation time is 36h.
10. The method of claim 2, wherein the fermentation is a shaking fermentation culture.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1924000A (en) * | 2006-09-21 | 2007-03-07 | 江苏省农业科学院 | Apergillus niger strain and application thereof |
| CN101768613A (en) * | 2010-03-09 | 2010-07-07 | 中国农业大学 | Preparation method of flavone genin of seabuckthorn leaves |
| CN104673682A (en) * | 2015-02-15 | 2015-06-03 | 华南农业大学 | Aspergillus niger and application thereof in biological prevention and control of aflatoxin |
| CN108642102A (en) * | 2018-04-27 | 2018-10-12 | 佛山科学技术学院 | A kind of method of isoflavone genin using microwave abstracting extraction microorganism production and its obtained isoflavone genin |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1924000A (en) * | 2006-09-21 | 2007-03-07 | 江苏省农业科学院 | Apergillus niger strain and application thereof |
| CN101768613A (en) * | 2010-03-09 | 2010-07-07 | 中国农业大学 | Preparation method of flavone genin of seabuckthorn leaves |
| CN104673682A (en) * | 2015-02-15 | 2015-06-03 | 华南农业大学 | Aspergillus niger and application thereof in biological prevention and control of aflatoxin |
| CN108642102A (en) * | 2018-04-27 | 2018-10-12 | 佛山科学技术学院 | A kind of method of isoflavone genin using microwave abstracting extraction microorganism production and its obtained isoflavone genin |
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| 黑曲霉发酵豆粕转化大豆异黄酮苷元的研究;李彦军;马小燕;毛跟年;许牡丹;张俊涛;;陕西科技大学学报(自然科学版)(04);全文 * |
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