CN109839455A - Survey the Fermented Soybean isoflavone content detections for commenting method based on one more - Google Patents
Survey the Fermented Soybean isoflavone content detections for commenting method based on one more Download PDFInfo
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Abstract
The invention discloses the Fermented Soybean isoflavone content detections based on " one surveys comment more " method, comprising the following steps: (1) foundation of genistein standard curve；(2) in sample to be tested genistein assay；(3) daidzein and Glycitein content in sample to be tested are calculated using relative correction factor." one surveys comment more " method of the invention is mutually authenticated with external standard method, no significant difference, as a result reliably.The method of the present invention is in the case where lacking daidzein and Glycitein reference substance, pass through genistein content in measurement Fermented Soybean, in conjunction with the content of relative correction factor f and chromatographic peak location Calculation daidzein and Glycitein, new method is provided for the quality control of Fermented Soybean.
Description
Technical field
The present invention relates to survey the Fermented Soybean isoflavone content detections for commenting method based on one more.
Background technique
Fermented Soybean is the fermentation processing product of legume soybean mature seed, and main active substances are isoflavones.
At present it is known that the soybean isoflavone compound in soybean has 12 kinds, including 3 kinds of daidzein, Glycitein, genistein glycosides
The monoglycosides of member and this 3 kinds of aglycons, acetyl group glucoside and malonyl glucoside.
Since ancient times, the complicated multiplicity of the zymotechnique of Fermented Soybean has gradually formed in very long fermentation evolution with " hair
It is thoroughly " the peculiar process and quality standard of essential requirement.During the fermentation, glycoside is converted to aglycon, the sheet of " hair is saturating "
Matter is that the maximization degradation of macromolecular substances and the maximization of glycoside substance convert.Isoflavone genin relative to its glycoside,
Anti-oxidant, antitumor, estrogen-like action etc. shows higher bioactivity.Therefore, soybean is different in Fermented Soybean
The content of flavone aglycone can evaluate its attenuation degree and quality.
The country of the related Fermented Soybean of present and provincial standard do not carry out objective quantitative to its isoflavone
Evaluation；General flavone content in ultraviolet spectrophotometry and high effective liquid chromatography for measuring Fermented Soybean is mainly used in document report,
The quality of Fermented Soybean is not can accurately reflect.Therefore, it is necessary to pass through while measuring multiple isoflavone index ingredients, realize
To the assay of isoflavone in Fermented Soybean.
Summary of the invention
To solve the above problems, the present invention provides the Fermented Soybean isoflavone content detection based on " one surveys comment more " method,
The following steps are included:
(1) foundation of genistein standard curve:
A, the preparation of reference substance solution:
Genistein reference substance is taken, 80% methanol is added to be made into reference substance solution；
B, the measurement of reference substance solution:
The reference substance solution for preparing series of concentrations, is injected separately into high performance liquid chromatograph, measures each chromatographic peak peak area, contaminated
Expect the standard curve of the wooden color；
Chromatographic condition is as follows:
Detection wavelength: 260nm；
Chromatographic column: C18Chromatographic column；
Mobile phase: 0.1% acetic acid water (A): acetonitrile (B)=(0~25min, 20%B~45%B)
(2) in sample to be tested genistein assay:
C, the preparation of test solution:
Sample to be tested is taken, adds 80% methanol to extract, filters to obtain test solution；
D, the measurement of test solution:
Test solution is taken, high performance liquid chromatograph is injected, with the identical chromatographic condition detection of step b, according to step (1)
Standard curve obtains the content of genistein in sample to be tested；
(3) daidzein and Glycitein content in sample to be tested are calculated using relative correction factor.
Further, the C18Chromatographic column is Agilent Eclipse Plus C18Chromatographic column, Inertsil
WondaSil C18Chromatographic column or Purospher STAR C18Chromatographic column.
Further, the specification of the chromatographic column be 250mm × 4.6mm, 5 μm.
Further, the high performance liquid chromatograph is Waters e2695,1200 Agilent or Shimadzu LC-20A.
Further, in step c, the extraction is ultrasonic extraction.
Further, the time of the ultrasonic extraction is 60 minutes.
Further, in step c, the volume mass ratio of 80% methanol and sample to be tested is 50mL:1g.
Further, the column temperature of the chromatographic condition is 20~30 DEG C, preferably 30 DEG C.
Further, the flow velocity of the chromatographic condition is 0.6~1.0mLmin-1, preferably 1.0mLmin-1。
Further, the relative correction factor of the step (3) is obtained by following step:
Daidzein, Glycitein and genistein reference substance are taken, 80% methanol is added to be configured to mixed reference substance solution；Take mixing
Reference substance solution injects high performance liquid chromatograph, with the identical chromatographic condition detection of step b, obtains daidzein, Glycitein
With the standard curve of genistein；
Using genistein as internal reference object, according to the calculation formula of relative response factor f: calculating daidzein, Glycitein and dye
Expect the Relative Factor between lignin, is averaged；
Wherein, relative response factor f calculation formula is as follows:
The mass concentration that A is chromatographic peak area in formula, W is ingredient, subscript n represent ingredient to be measured, subscript behalf internal reference object.
The experiment proved that chromatographic condition of the present invention can efficiently separate daidzein, Glycitein and genistein, thus
Their content of Accurate Determining.Also, " one surveys comment more " method of the invention is mutually authenticated with external standard method, no significant difference, as a result
Reliably.
In addition, genistein, as common reference substance, separation prepares relatively simple.The method of the present invention is lacking daidzin
In the case where member and Glycitein reference substance, by genistein content in measurement Fermented Soybean, in conjunction with relative correction factor f and color
The content of spectral peak location Calculation daidzein and Glycitein.Therefore, method of the invention can be used for the detection of Fermented Soybean.
Obviously, above content according to the present invention is not being departed from according to the ordinary technical knowledge and customary means of this field
Under the premise of the above-mentioned basic fundamental thought of the present invention, the modification, replacement or change of other diversified forms can also be made.
The specific embodiment of form by the following examples does further specifically above content of the invention again
It is bright.But the range that this should not be interpreted as to the above-mentioned theme of the present invention is only limitted to example below.It is all to be based on above content of the present invention
The technology realized all belongs to the scope of the present invention.
Detailed description of the invention
Fig. 1 is mixed reference substance solution HPLC chromatogram (1-daidzein；2-Glyciteins；3-genisteins).
Fig. 2 is the HPLC chromatogram (1-daidzein of test solution；2-Glyciteins；3-genisteins).
Specific embodiment
1 instrument
Waters e2695 high performance liquid chromatograph, quaternary pump, 2998PDA detector；Agilent Technologies
1200Series high performance liquid chromatograph, G1311C quaternary pump, G1329B autosampler, G1316A column oven, G1362A bis-
Pole pipe array detector (Agilent company, the U.S.)；Shimadzu Shimadzu LC-20A, SIL-20A autosampler, SPD-20A
Detector, CTO-20A column oven, LC solution chromatographic work station software (Japanese Shimadzu Corporation)；BP211D electronic analysis
Balance (German Sartouris limited liability company).
2 materials and reagent
Fermented Soybean: commercially available Fermented Soybean.
Isoflavone genin class reference substance: daidzein (Chinese food drug assay research institute, purity 99.0%)；
Glycitein (sigma, purity 98%)；Genistein (Chinese food drug assay research institute, purity 99.1%).
Methanol: chromatographic grade, Fisher company, the U.S..Acetonitrile: chromatographic grade, Fisher company, the U.S..
3 HPLC chromatogram conditions
Chromatographic column Agilent Eclipse Plus C18Chromatographic column (250mm × 4.6mm, 5 μm)；With 0.1% acetic acid water (A):
Acetonitrile (B) is mobile phase, (0~25min, 20%B~45%B) gradient elution, column flow 1.0min/mL, Detection wavelength
260nm, 30 DEG C of column temperature, 20 μ L of sample volume.
4 one survey the foundation for commenting method more
The determination of 4.1 relative correction factors
4.1.1 the preparation of mixed reference substance solution
Accurately weighed daidzein, Glycitein, genistein reference substance are placed in right amount in 100mL volumetric flask respectively, add 80%
Methanol constant volume is made into the reference substance solution that mass concentration is respectively 0.98mg/mL, 0.96mg/mL, 0.98 mg/mL to scale,
As reference substance stock solution.The above-mentioned reference substance stock solution of precision absorption is appropriate, and being matched with 80% methanol is 0.1,0.5,1,2,5,
The serial mixed reference substance solution of 10,20 μ g/mL.Above-mentioned serial mixed reference substance solution is stored in 4 DEG C of refrigerators, it is spare.
4.1.2 prepared by test solution
Precision weighs Fermented soybean (crossing 40 meshes) about 0.5g and is accurate to (0.0001g), sets in stuffed conical flask, is added
25mL80% methanol solution filters after ultrasonic vibration 60min, takes subsequent filtrate to obtain the final product.It is accurate respectively to draw above-mentioned reference substance solution
With each 20 μ L of test solution, high performance liquid chromatograph, measurement, the result is shown in Figure 1, Fig. 2 are injected
4.1.3 linear, quantitative limit and detection limit
Sample introduction is analyzed by 4.1.1 20 μ L of lower serial mixed reference substance solution of accurate absorption respectively, using peak area as ordinate, mixing
Reference substance solution concentration is abscissa, draws standard curve；It is diluted step by step with the reference substance solution of minimum concentration, respectively with noise
Than the concentration for 3 and 10 as detection limit and quantitative limit, it is shown in Table 1.
1 linear relationship of table and quantitative limit, detection limit
| Reference substance | Standard curve | R2 | The range of linearity (μ g/mL) | LOQ(ng/mL) | LOD(ng/mL) |
| Daidzein | Y=111504x-1259.2 | 1 | 0.098~19.6 | 0.02 | 0.01 |
| Glycitein | Y=96999x-1242.8 | 1 | 0.096~19.2 | 0.2 | 0.1 |
| Genistein | Y=157815x-1946.7 | 1 | 0.098~19.6 | 0.05 | 0.02 |
4.1.4 the calculating of relative correction factor
Under " 2 " item under the conditions of determining HPLC chromatogram analysis, it is molten that precision draws the series mixing reference substance under " 4.1.1 " item
Liquid, difference 20 μ L of sample introduction.Using genistein as internal reference object, according to relative response factor (f) calculation formula (1), daidzin is calculated
Member, Glycitein, the corresponding factor between genistein, take its average value.
A in formula, W are respectively the mass concentration of chromatographic peak area, ingredient, subscript n, and s is respectively represented
Ingredient and internal reference object to be measured.It the results are shown in Table 2, calculated result relative correction factor value under this condition is fDaidzein/genistein=
0.7087, RSD 0.68%；fGlycitein/genistein=0.6179, RSD 1.20%.Show different mixed reference substance solution concentration
Under relative correction factor it is relatively stable.
Relative correction factor under the different sampling volumes of table 2
| Mixed reference substance solution concentration (μ g/mL) | F daidzein/genistein | F Glycitein/genistein |
| 0.1 | 0.7156 | 0.6330 |
| 0.5 | 0.7155 | 0.6225 |
| 1 | 0.7039 | 0.6139 |
| 2 | 0.7067 | 0.6130 |
| 5 | 0.7054 | 0.6134 |
| 10 | 0.7076 | 0.6149 |
| 20 | 0.7064 | 0.6146 |
| Average value | 0.7087 | 0.6179 |
| RSD (%) | 0.68 | 1.20 |
4.1.5 precision test
Precision pipettes mixed reference substance solution under " 4.1.1 " item, and continuous sample introduction 6 times, 20 μ L, records each at swarming respectively every time
Area simultaneously calculates its RSD, as a result daidzein, Glycitein, and the RSD value of genistein is respectively 0.47%, 0.52%,
0.78%, show that instrument precision is good.
4.1.6 repetitive test
Precision is weighed with a collection of Fermented soybean about 0.5g, according to 3.1.2 lower operations, is prepared 6 parts of test solutions in parallel, is surveyed
Daidzein is obtained, Glycitein, the content RSD of genistein is respectively 0.66%, 1.03%, 0.45%, shows that sample repeats
Property is good.
4.1.7 stability test
Precision draws same 20 μ L of mixed reference substance solution and measures soybean respectively respectively at 0,2,4,6,8,12,24,36h sample introduction
Aglycon, Glycitein, the peak area of genistein, the RSD of peak area are respectively 0.32%, 1.26%, 0.14%.Show
The mixed reference substance solution is good in 36h internal stability.
4.1.8 it is loaded recovery test
The Fermented soybean 0.25g with a collection of known content is taken, accurately weighed, parallel 6 parts, daidzein is added in precision respectively,
Glycitein, genistein reference substance stock solution calculates daidzein by test solution measurement is prepared under 4.1.2, yellow
Beans flavine, the sample recovery rate of genistein, the results are shown in Table 3.
Daidzein in 3 Fermented Soybean of table, Glycitein, the sample recovery rate test result of genistein
4.2 1 surveys comments method system robustness and system suitability
4.2.1 the durability and system suitability of relative correction factor
Waters 2695 is selected in this experiment respectively, Agilent 1200 and Shimadzu LC-20A highly effective liquid phase chromatographic system with
Agilent Eclipse Plus C18(4.6mm × 250mm, 5 μm), Inertsil WondaSil C18(4.6mm ×
250mm, 5 μm) or Purospher STAR C18(4.6mm × 250mm, 5 μm) 3 kinds of chromatographic columns investigate chromatographic system to opposite school
The influence of positive divisor.Different chromatographic systems influence smaller (RSD < 5.0%) on it as the result is shown, and reproducibility is good, is shown in Table 4.
Influence of the different chromatographic systems of table 4 to relative correction factor
4.2.2 the positioning of component chromatographic peak to be determined
4.2.2.1 different instruments and chromatographic column are to relative retention time
According to the retention time of B, relative retention time r using A relative to B is shown in formula (2), can position to peak.
R=rx/rs (2)
Wherein rx, rsRespectively indicate the retention time of determinand and internal reference object.
Experiment has investigated relative retention time value in different brands chromatograph, the reproducibility of different brands chromatographic column respectively,
It the results are shown in Table 5.The result shows that different chromatographic columns are more apparent to the retention time variation of each ingredient, but opposite reservation between each ingredient
Less, RSD < 5.0%, the retention time with model chromatographic column each ingredient on different instruments changes less for value variation.Therefore, originally
Experiment selects relative retention value more appropriate as the positioning index of target chromatographic peak.
Table 5 one surveys the positioning for commenting method ingredient chromatographic peak to be measured more
4.2.2.2 different in flow rate and column temperature is to relative retention time
Under the same conditions, using Shimadzu LC-20A highly effective liquid phase chromatographic system and Agilent Eclipse Plus C18Chromatography
Column investigates (0.6,0.8,1.0mLmin different in flow rate respectively-1) and different column temperatures (20,25,30 DEG C) to daidzein, soya bean
Flavine, the influence of the relative retention time of genistein, influence of the different in flow rate as the result is shown, column temperature to relative retention time compared with
Few (RSD < 3.0%).
4.3 " one surveys comment more " method external standard methods compare
First using external standard method to daidzein in Fermented Soybean, Glycitein, genistein is measured, and is resettled a survey and is commented more
Method is calculated, and the result that two methods calculate is compared, and is surveyed with verifying one and is commented method to for measuring in Fermented Soybean more
The accuracy of isoflavone constituents Content evaluation.The result shows that the isoflavone content that two methods measure is without significant
Sex differernce prompts the method established to have preferable confidence level.It the results are shown in Table 6.
Daidzein in method measurement Fermented Soybean, the comparison of Glycitein content are commented in 6 external standard method of table and a survey more
5 discuss
5.1 Detection wavelength
Efficient liquid phase DAD detector is selected in this experiment, to daidzein, Glycitein, genistein pair at 190~400nm
Full wavelength scanner has been carried out according to product.Daidzein as the result is shown, Glycitein, the maximum absorption wavelength point of genistein reference substance
Not at 257nm, 249nm, 260nm.In view of internal reference object used is genistein, and the maximum absorption wave appearance of three kinds of aglycons
Closely, therefore select the absorption maximum 260nm of genistein as Detection wavelength.
The selection of 5.2 internal reference objects
It is internal reference object that genistein is selected in this experiment, and because the preparation of its reference substance is easy to get, physicochemical property is relatively stable, can protect for a long time
Deposit use.
The selection of 5.3 chromatographic conditions
Daidzein, Glycitein, genistein are isoflavone genin constituents, and property is similar.The author attempts to use
The flow phase systems such as methanol-water, acetonitrile-water, methanol-water-acetic acid, acetonitrile-water-acetic acid are under conditions of gradient elution to soybean
The separation of aglycon, Glycitein, genistein is investigated, and is carried out gradient using acetonitrile-acetic acid water system as the result is shown and is washed
De-, analysis time is shorter, and 3 ingredients can reach desired separated, and peak shape is good.Therefore finally use 0.1% acetic acid water (A):
Acetonitrile (B)=(0~25min, 20%B~45%B) carries out gradient elution.
5.4 interpretation of result
The present invention measures isoflavone constituents daidzein, Glycitein, genistein in 13 batches of Fermented Soybean samples and contains
Amount.The survey that the present invention uses comments method to be mutually authenticated with external standard method, no significant difference, as a result reliably.The method of the present invention is lacking
It, can be by genistein content in measurement Fermented Soybean, in conjunction with opposite school in the case where weary daidzein and Glycitein reference substance
The content of positive divisor f and chromatographic peak location Calculation daidzein and Glycitein.The survey that the present invention establishes comments method for light beans
The quality control of fermented soya beans, salted or other wise provides new method.
Claims (11)
1. the Fermented Soybean isoflavone content detection based on " one surveys comment more " method, comprising the following steps:
(1) foundation of genistein standard curve:
A, the preparation of reference substance solution:
Genistein reference substance is taken, 80% methanol is added to be configured to reference substance solution；
B, the measurement of reference substance solution:
The reference substance solution for preparing series of concentrations, is injected separately into high performance liquid chromatograph, measures each chromatographic peak peak area, obtain
The standard curve of dyewood color；
Chromatographic condition is as follows:
Detection wavelength: 260nm；
Chromatographic column: C18 chromatographic column；
Mobile phase: 0.1% acetic acid water (A): acetonitrile (B)=(0~25min, 20%B~45%B)
(2) in sample to be tested genistein assay:
C, the preparation of test solution:
Sample to be tested is taken, adds 80% methanol to extract, filters to obtain test solution；
D, the measurement of test solution:
Test solution is taken, high performance liquid chromatograph is injected, with the identical chromatographic condition detection of step b, according to the mark of step (1)
Directrix curve obtains the content of genistein in sample to be tested；
(3) daidzein and Glycitein content in sample to be tested are calculated using relative correction factor.
2. content detection according to claim 1, it is characterised in that: the chromatographic column is Agilent Eclipse Plus
C18 chromatographic column, Inertsil WondaSil C18 chromatographic column or Purospher STAR C18 chromatographic column.
3. content detection according to claim 1, it is characterised in that: the specification of the chromatographic column be 250mm × 4.6mm, 5
μm。
4. content detection according to claim 1-3, it is characterised in that: the high performance liquid chromatograph is
Waters e2695,1200 Agilent or Shimadzu LC-20A.
5. content detection according to claim 1, it is characterised in that: in step c, the extraction is ultrasonic extraction.
6. content detection according to claim 5, it is characterised in that: the extraction time is 60 minutes.
7. the content detection belonging to according to claim 1, it is characterised in that: in step c, 80% methanol and sample to be tested
Volume mass ratio is 50mL:1g.
8. content detection according to claim 1-7, it is characterised in that: the column temperature of the chromatographic condition be 20~
30 DEG C, preferably 30 DEG C.
9. content detection according to claim 1-8, it is characterised in that: the flow velocity of the chromatographic condition is 0.6
~1.0mLmin-1, preferably 1.0mLmin-1。
10. -9 described in any item content detections according to claim 1, it is characterised in that: the relative correction of the step (3) because
Son is obtained by following step:
Daidzein, Glycitein and genistein reference substance are taken, 80% methanol is added to be configured to mixed reference substance solution；
Mixed reference substance solution is taken, high performance liquid chromatograph is injected, with the identical chromatographic condition detection of step b, obtains daidzin
The standard curve of member, Glycitein and genistein；
Using genistein as internal reference object, according to the calculation formula of relative response factor f: calculating daidzein, Glycitein and dye
Expect the Relative Factor between lignin, is averaged；
Wherein, relative response factor f calculation formula is as follows:
The mass concentration that A is chromatographic peak area in formula, W is ingredient, subscript n represent ingredient to be measured, subscript behalf internal reference object.
11. the content inspection that content detection described in claim 1-10 any one is used to detect isoflavone in Fermented Soybean
It surveys.
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| CN112505216A (en) * | 2020-09-04 | 2021-03-16 | 广西壮族自治区药用植物园 | One-test-multiple-evaluation method for three non-alkaloid components in subprostrate sophora and application thereof |
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Application publication date: 20190604 |