CN108645947A - The detection method of tyramine content in a kind of soy sauce - Google Patents
The detection method of tyramine content in a kind of soy sauce Download PDFInfo
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Abstract
The present invention provides a kind of detection methods of tyramine content in soy sauce, belong to food analysis technical field.It uses method for column front derivation ultra-performance liquid chromatography, uses I class Ultra Performance Liquid Chromatography instruments of Waters Acquity, C18 columns.The method of the present invention amount of samples is few, and the time is short, and method is linearly good, easy to operate, favorable reproducibility, and accuracy is high.
Description
Technical field：
The present invention relates to a kind of food detection methods, and in particular to the ultra performance liquid chromatography of tyramine content in a kind of soy sauce
Detection method.
Background technology：
Tyrasamine (Tyramine) also known as Uteramin are a kind of nitrogenous low molecular biogenic amines.Biogenic amine is as one
Class physiological activator participates in the metabolic activity in organism.Biogenic amine is widely present in varieties of food items, rich in protein
With relatively more in the food of amino acid, especially fish and its product, cheese, meat products and fermentation based food.In food
Tyrasamine is mainly that the decarboxylation enzymatic that is generated by related microorganisms is sloughed the carboxyl of tyrosine and generated or aldehyde and ketone pass through
Amination and transamination generate.Therefore there are two sources for the biogenic amine in food, first, being brought by raw material, second is that microorganism
Decarboxylic reaction generate.Because traditional fermentation process is difficult to control, mechanism is not apparent, the biogenic amine in natural fermented food
Problem is more paid close attention to by people.Excess free enthalpy biogenic amine may cause headache, dizziness, nausea, respiratory distress, palpitaition etc.
Various poisoning symptoms.In all biogenic amines, maximum to Human health effects is histamine and tyrasamine.Tyrasamine, which has, increases blood pressure
Effect, the excessive tyrasamine that absorbs can consume monoamine oxidase inhibitors in vivo, and so as to cause serious side effect, here it is tyrasamines
Also known as tyrotoxin the reason of.Tyrasamine, which is also manifested by the harm of human body, promotes peripheral vessel to shrink, and irritates heart rate, increases
Blood sugar concentration eliminates the norepinephrine in nervous system, to cause migraines.Human oral's tyrasamine is more than 100mg can
Cause migraine, Poisoning swelling can be caused more than 1080mg, tyramine content must not exceed 100- in European Union's regulation food
800mg/kg。
Soy sauce is a kind of food with a long history, for going with rice or bread and seasoning, because of its unique flavor, delicious flavour, nutrition
It enriches and is made and eaten extensively.But the method that the making of soy sauce generally uses spontaneous fermentation, fermenting microbe is complicated, therefore deposits
In the security risk of higher microbial origin biogenic amine.For food-safe consideration, people should reduce biology as far as possible
The intake of amine, and the content for detecting and monitoring biogenic amine in food just becomes the task of top priority.Since tyrosine is in fermentation process
Middle generation tyrasamine, therefore can not only ensure food safety to the analysis of tyrasamine in soy sauce, can also obtain with food production and
The relevant useful information of fermentation technology process.
The detection method of biogenic amine has gas chromatography tandem mass spectrometry method, the chromatography of ions, high performance liquid chromatography, thin layer
Chromatography, high performance liquid chromatography-tandem mass method etc., these methods have processing step relatively complicated, and analysis time is long, no
The shortcomings of easy to operate.The present invention passes through ultra-performance liquid chromatography (Ultra Performance Liquid
Chromatography, UPLC) measure tyrasamine detection method can be obtained more by using the chromatographic column of small particle size filler
Good separating effect and shorter analysis time, while simplifying processing step.Therefore the method for the present invention has amount of samples few, when
Between short, the advantages that method is linearly good, easy to operate, favorable reproducibility, accuracy is high.
Invention content：
Present invention aims at sample pretreatment step is simplified, shorten sample detection time, research and design is examined using UPLC
Survey method rapidly and accurately measures tyramine content in soy sauce.
The technical problem to be solved by the present invention is to what is be achieved through the following technical solutions：
(1) preparation of standard solution：Precision weighs tyrasamine and is made into a concentration of 1mgmL with 0.1M hydrochloric acid-1Solution, micropore
0.22 μm of 4 DEG C of filtering of filter membrane saves backup.The gradient standard working solution 0.1M hydrochloric acids used are to required concentration.It is accurate
It weighs internal standard and is configured to a concentration of 50 μ gmL with deionized water-1Solution, 0.22 μm of miillpore filter, 4 DEG C of filtering saves backup.
(2) preparation of sample solution：Soy sample deionized water dilutes 5-20 times, 0.22 μm of filtering of miillpore filter；Add
50μg·mL-1100 μ L of inner mark solution, perform the derivatization reaction.
(3) derivative reaction：100 μ L of standard solution or sample are taken, add saturated sodium bicarbonate 100 the μ L and 5- of pH10 respectively
10mg·mL-1200 μ L of dansyl Cl (solvent is acetone), 10-20min is protected from light at 50-60 DEG C.After plus ammonium hydroxide
100 μ L terminate reaction 20-30min.Add acetonitrile constant volume to 1mL.0.22 μm of filtering of miillpore filter.Post detection on filtrate.
(4) it detects：Using I-Class Ultra Performance Liquid Chromatography instruments of Waters Acquity, C18,2.1 × 50mm, 1.7 μm
Chromatographic column, mobile phase are deionized water and acetonitrile, flow velocity 0.3mLmin-1, ultraviolet detection wavelength 254nm, 10 μ L of sample size, column
55 DEG C of temperature, mobile phase A is acetonitrile, and Mobile phase B is deionized water, detector：PDA detectors.Use internal standard method with target analysis
The ratio of object peak area and internal standard peak area carries out the quantitative content for calculating tyrasamine in sample.
The detailed process that the step (1) prepares mixing gradient standard working solution is as follows:By a concentration of 1mgmL-1's
Tyrasamine standard solution 0.1M hydrochloric acid compound concentration gradients are 50,100,200,300,400,500 μ gmL-1Standard work it is molten
Liquid, a concentration of 50 μ gmL of the internal standard benzene methanamine of the hybrid standard working solution of each concentration-1。
The elution program of UPLC is：Mobile phase A is acetonitrile, and Mobile phase B is deionized water, using gradient elution, in 0-
20min, A 50-85%, B 50-15%, 20-21min, A 85-50%, B 15-50%, 21-25min, A 50%, B
50%.
Compared with the literature, separation method processing procedure is simple, and analysis time is short by the present invention, and the method for foundation is simple and reliable,
It can be applied to the detection of tyramine content in soy sauce；This method is simple and convenient to sample analysis, and detection limit is low, high sensitivity, weight
Renaturation and the rate of recovery are good.
Description of the drawings
Fig. 1 is the UPLC chromatography peak figures added with interior target standard solution；
Fig. 2 is the UPLC chromatography peak figures added with interior target soy sample；
Fig. 3 is the UPLC chromatography peak figures added with internal standard and the soy sample of standard solution；
Fig. 4 is the standard curve of tyrasamine.
Specific implementation mode
Under embodiment of the present invention will be described in detail in conjunction with the embodiments, but those skilled in the art will manage
Solution, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the invention.Specific item is not specified in embodiment
Part person carries out according to conventional conditions or manufacturer's recommended conditions.
The present invention is described in further detail below by specific embodiment.
Embodiment 1
(a) pretreatment of sample solution：Soy sample 5mL to be detected is taken to dilute 10 times with deionized water, miillpore filter
0.22 μm of filtering, 4 DEG C of filtrate save backup.
(b) derivative reaction of sample：100 μ L samples are taken from filtrate, and 50 μ gmL are added-1100 μ L of inner mark solution, then
Sequentially add the 100 μ L of saturated sodium bicarbonate, the 8mgmL prepared with acetone that are 10 with sodium hydroxide adjustment pH value-1Red sulphonyl
200 μ L of chlorine are carried out in the dark derivative reaction at 55 DEG C, react 15min.After plus 100 μ L of ammonium hydroxide terminate reaction 25min.
Add acetonitrile constant volume to 1mL.0.22 μm of miillpore filter filters, post detection on filtrate.
(c) testing conditions of UPLC：Using I-Class Ultra Performance Liquid Chromatography instruments of Waters Acquity, C18,2.1 ×
50mm, 1.7 μm of chromatographic columns, mobile phase are deionized water and acetonitrile, flow velocity 0.3mLmin-1, ultraviolet detection wavelength 254nm, into
10 μ L of sample amount, 55 DEG C of column temperature, mobile phase A are acetonitrile, and Mobile phase B is deionized water, detector：PDA detectors.The elution of UPLC
Program is：Mobile phase A is acetonitrile, and Mobile phase B is deionized water, using gradient elution, in 0-20min, A 50-85%, B 50-
15%, 20-21min, A 85-50%, B15-50%, 21-25min, A 50%, B 50%.
(d) step (c) is measured in numerical value substitution tyrasamine standard items equation of linear regression and is calculated, obtain junket in soy sample
The content of amine.
Tyrasamine standard items equation of linear regression:Precision weighs tyrasamine 100mg and is put in 100mL brown volumetric flasks, uses 0.1M
Hydrochloric acid is settled to scale to get a concentration of 1mgmL-1Tyrasamine standard solution, the filtering of 0.22 μm of miillpore filter, 4 DEG C of preservations are standby
With；The quality 100mg that precision weighs internal standard benzene methanamine is put in 100mL volumetric flasks, and a concentration of 1mg is configured to deionized water
mL-1Solution, be further continued for being diluted to a concentration of 50 μ gmL with deionized water-1Solution, the filtering of 0.22 μm of miillpore filter, 4 DEG C
It saves backup.
By a concentration of 1mgmL-1Tyrasamine standard solution with 0.1M hydrochloric acid compound concentration gradients be 50,100,200,300,
400、500μg·mL-1Standard working solution, a concentration of 50 μ g of the internal standard benzene methanamine of the standard working solution of each concentration
mL-1.Reaction is performed the derivatization by step (b) respectively, after 0.22 μm of membrane filtration, takes and is detected in right amount using UPLC,
UPLC methods conditional synchronization is rapid (c)；Using one concentration of ratio of peak area as linear regression, the linear regression of tyrasamine standard items is obtained
Equation.
Embodiment 2
(a) pretreatment of sample solution：Soy sample 2mL to be detected is taken to dilute 20 times with deionized water, miillpore filter
0.22 μm of filtering, 4 DEG C of filtrate save backup.
(b) derivative reaction of sample：100 μ L samples are taken from filtrate, and 50 μ gmL are added-1100 μ L of inner mark solution, then
Sequentially add the 100 μ L of saturated sodium bicarbonate, the 5mgmL prepared with acetone that are 10 with sodium hydroxide adjustment pH value-1Red sulphonyl
200 μ L of chlorine are carried out in the dark derivative reaction at 50 DEG C, react 20min.After plus 100 μ L of ammonium hydroxide terminate reaction 30min.
Add acetonitrile constant volume to 1mL.0.22 μm of miillpore filter filters, post detection on filtrate.
(c) testing conditions of UPLC：Using I-Class Ultra Performance Liquid Chromatography instruments of Waters Acquity, C18,2.1 ×
50mm, 1.7 μm of chromatographic columns, mobile phase are deionized water and acetonitrile, flow velocity 0.3mLmin-1, ultraviolet detection wavelength 254nm, into
10 μ L of sample amount, 55 DEG C of column temperature, mobile phase A are acetonitrile, and Mobile phase B is deionized water, detector：PDA detectors.The elution of UPLC
Program is：Mobile phase A is acetonitrile, and Mobile phase B is deionized water, using gradient elution, in 0-20min, A 50-85%, B 50-
15%, 20-21min, A 85-50%, B15-50%, 21-25min, A 50%, B 50%.
(d) step (c) is measured in numerical value substitution tyrasamine standard items equation of linear regression and is calculated, obtain junket in soy sample
The content of amine.
Tyrasamine standard items equation of linear regression:Precision weighs tyrasamine 100mg and is put in 100mL brown volumetric flasks, uses 0.1M
Hydrochloric acid is settled to scale to get a concentration of 1mgmL-1Tyrasamine standard solution, the filtering of 0.22 μm of miillpore filter, 4 DEG C of preservations are standby
With；The quality 100mg that precision weighs internal standard benzene methanamine is put in 100mL volumetric flasks, and a concentration of 1mg is configured to deionized water
mL-1Solution, be further continued for being diluted to a concentration of 50 μ gmL with deionized water-1Solution, the filtering of 0.22 μm of miillpore filter, 4 DEG C
It saves backup.
By a concentration of 1mgmL-1Tyrasamine standard solution with 0.1M hydrochloric acid compound concentration gradients be 50,100,200,300,
400、500μg·mL-1Standard working solution, a concentration of 50 μ g of the internal standard benzene methanamine of the standard working solution of each concentration
mL-1.Reaction is performed the derivatization by step (b) respectively, after 0.45 μm of membrane filtration, takes and is detected in right amount using UPLC,
UPLC methods conditional synchronization is rapid (c)；Using one concentration of ratio of peak area as linear regression, the linear regression of tyrasamine standard items is obtained
Equation.
Embodiment 3
(a) pretreatment of sample solution：Soy sample 10mL to be detected is taken to dilute 5 times with deionized water, miillpore filter
0.22 μm of filtering, 4 DEG C of filtrate save backup.
(b) derivative reaction of sample：100 μ L samples are taken from filtrate, and 50 μ gmL are added-1100 μ L of inner mark solution, then
Sequentially add the 100 μ L of saturated sodium bicarbonate, the 10mgmL prepared with acetone that are 10 with sodium hydroxide adjustment pH value-1Red sulphonyl
200 μ L of chlorine are carried out in the dark derivative reaction at 60 DEG C, react 10min.After plus 100 μ L of ammonium hydroxide terminate reaction 20min.
Add acetonitrile constant volume to 1mL.0.22 μm of miillpore filter filters, post detection on filtrate.
(c) UPLC testing conditions：Using I-Class Ultra Performance Liquid Chromatography instruments of Waters Acquity, C18,2.1 ×
50mm, 1.7 μm of chromatographic columns, mobile phase are deionized water and acetonitrile, flow velocity 0.3mLmin-1, ultraviolet detection wavelength 254nm, into
10 μ L of sample amount, 55 DEG C of column temperature, mobile phase A are acetonitrile, and Mobile phase B is deionized water, detector：PDA detectors.The elution of UPLC
Program is：Mobile phase A is acetonitrile, and Mobile phase B is deionized water, using gradient elution, in 0-20min, A 50-85%, B 50-
15%, 20-21min, A 85-50%, B15-50%, 21-25min, A 50%, B 50%.
(d) step (c) is measured in numerical value substitution tyrasamine standard items equation of linear regression and is calculated, obtain junket in soy sample
The content of amine.
Tyrasamine standard items equation of linear regression:Precision weighs tyrasamine 100mg and is put in 100mL brown volumetric flasks, uses 0.1M
Hydrochloric acid is settled to scale, up to a concentration of 1mgmL-1Tyrasamine standard solution, the filtering of 0.22 μm of miillpore filter, 4 DEG C of preservations are standby
With；The quality 100mg that precision weighs internal standard benzene methanamine is put in 100mL volumetric flasks, and a concentration of 1mg is configured to deionized water
mL-1Solution, be further continued for being diluted to a concentration of 50 μ gmL with deionized water-1Solution, 0.22 μm of miillpore filter filters 4 DEG C
It saves backup.
By a concentration of 1mgmL-1Tyrasamine standard solution with 0.1M hydrochloric acid compound concentration gradients be 50,100,200,300,
400、500μg·mL-1Standard working solution, a concentration of 50 μ g of the internal standard benzene methanamine of the standard working solution of each concentration
mL-1.Reaction is performed the derivatization by step (b) respectively, after 0.22 μm of membrane filtration, takes and is detected in right amount using UPLC,
UPLC methods conditional synchronization is rapid (c)；Each concentration does 3 parallel, difference sample detections.By taking wherein single injected sampling as an example, obtained color
Spectral peak figure is as shown in Figure 3.Using the average value of the ratio of peak area as abscissa, with corresponding a concentration of ordinate, carry out linear
It returns, obtains regression curve and see Fig. 4.
The analysis parameter of UPLC detection methods is shown in Table 1-3.
The equation of linear regression and relevant parameter of 1 tyrasamine standard items of table
Note:x：Tyrasamine concentration (μ gmL-1)；y：Peak area ratio；* detection limit：Signal-to-noise ratio (S/N) is 3；* quantitative limits：
Signal-to-noise ratio (S/N) is 10.
The R for the equation of linear regression that table 1 and Fig. 4 can be seen that2It is 0.9997, linear stable, error is small.From table 1
Understand that concentration limit is 250ngmL-1, detect and be limited to 50ngmL-1, illustrate that the detection limit of this method is low, meet trace
The requirement of measurement.8 measurement results of same sample continuous sample introduction are carried out calculating its relative standard deviation being 0.06%, illustrate instrument
The precision of device is good.It is 0.20% to measure its relative standard deviation respectively within for three days on end to same sample, illustration method
Stability is good.
2 repeatability of table and reproducibility experiment
To standard solution and soy sample in interior METHOD FOR CONTINUOUS DETERMINATION 6 times on the same day, relative standard deviation is respectively 2.12 Hes
3.62%；Standard solution and soy sample are measured 1 time daily interior for three days on end, relative standard deviation is 3.13 and 3.09%.
As a result illustrate that this method has good repeatability and reproducibility.
3 recovery of standard addition of table is tested
It can be seen that from table 3, the average recovery rate of the detection method is 87.3%, relative standard deviation 6.63%.
The 5 kinds of soy samples bought from market are detected according to the method for the present invention, tyrasamine is calculated by equation of linear regression
Content, the results are shown in Table 4.
The content (Mean ± SD) (n=3) of tyrasamine in 45 kinds of soy samples of table
From table 4, it can be seen that purchase five kinds of soy sauce in tyrasamine content within the scope of 166-792mg/L, without departing from
Standard requirement as defined in European Union.
The method that UPLC provided by the invention measures tyramine content in soy sauce, amount of samples is few, measurement result quick and precisely,
Analysis time is fast, and solvent carrying capacity is few, the experimental results showed that, measurement result is stablized, and has good specificity, precision and recycling
Rate.Have the characteristics that micro, easy, quick, sensitive, the requirement of determination of trace can be met.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, any made by repair
Change, equivalent replacement, improvement etc. should all be included in the protection scope of the present invention.
Claims (3)
1. the detection method of tyramine content in a kind of soy sauce, it is characterised in that this method includes the following steps：
(1) preparation of standard solution：Precision weighs tyrasamine and is made into a concentration of 1mgmL with 0.1M hydrochloric acid-1Solution, miillpore filter
0.45 μm of 4 DEG C of filtering saves backup.The gradient standard working solution 0.1M hydrochloric acids used are to required concentration.Precision weighs
Internal standard is configured to a concentration of 100 μ gmL with deionized water-1Solution, 0.45 μm of miillpore filter, 4 DEG C of filtering saves backup
(2) preparation of sample solution：Soy sauce deionized water dilutes 5-20 times, 0.45 μm of filtering of miillpore filter；Add 50 μ gmL-1
100 μ l of inner mark solution, perform the derivatization reaction.
(3) derivative reaction：100 μ l of standard solution or sample are taken, the saturated carbon for being respectively plus with sodium hydroxide adjustment pH value 10
100 μ l of sour hydrogen sodium, the 5-10mgmL prepared with acetone-1200 μ l of dansyl Cl, 10-15min is protected from light at 50-60 DEG C.
After plus 100 μ l of ammonium hydroxide terminate reaction 20-30min.Add acetonitrile constant volume to 1ml.0.45 μm of filtering of miillpore filter.Filtrate upper prop
Detection.
(4) it detects：Using I class Ultra Performance Liquid Chromatography instruments of Waters Acquity, C18,2.1 × 50mm, 1.7 μm of chromatographies
Column, mobile phase are deionized water and acetonitrile, flow velocity 0.3mLmin-1, ultraviolet detection wavelength 254nm, 10 μ L of sample size, column temperature 55
DEG C, mobile phase A is acetonitrile, and Mobile phase B is water, detector：PDA detectors.Use internal standard method with target analytes peak area and
The ratio of internal standard peak area carries out the quantitative content for calculating tyrasamine in sample.
2. the detection method of tyramine content in soy sauce as described in claim 1, which is characterized in that the step (1) prepares mixing
The detailed process of gradient standard working solution is as follows:By a concentration of 1mgmL-1Tyrasamine standard solution with 0.1M hydrochloric acid prepare it is dense
Degree gradient is 50,100,200,300,400,500 μ gmL-1Standard working solution, each concentration hybrid standard work it is molten
A concentration of 50 μ gmL of the internal standard benzylamine of liquid-1。
3. the detection method of tyramine content in soy sauce as described in claim 1, which is characterized in that the elution program of UPLC is：Stream
Dynamic phase A is acetonitrile, and Mobile phase B is water, in 0-20min, A 50-85%, B 50-15%, 20-21min, A 85-50%, B
15-50%, 21-25min, A 50%, B 50%.
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| CN108645947B (en) | 2021-01-05 |
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Effective date of registration: 20220810 Address after: 521000 Wen CI Zhen Zhong she Cun Tian tou Zi Ling, Chao'an District, Chaozhou City, Guangdong Province Patentee after: Good taste food Co.,Ltd. Address before: 541004 the Guangxi Zhuang Autonomous Region Guilin City Seven Star District Building Road No. 12 Patentee before: GUILIN University OF TECHNOLOGY |