CN111855829B - Method for detecting lactulose in dairy product - Google Patents
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Abstract
The invention provides a method for detecting lactulose in dairy products, which comprises the following steps: adding beta-D-galactosidase into a dairy product sample, carrying out enzymolysis reaction on lactose and lactulose to generate galactose, fructose and glucose, carrying out oximation reaction on the galactose, the glucose and the fructose with methoxyamine respectively, carrying out derivatization reaction on the generated reactant and N-methyl-N-trimethylsilane trifluoroacetamide, and finally obtaining the test solution. And analyzing the test sample liquid by adopting an ultra-high performance liquid chromatography tandem mass spectrometer to obtain the content of lactulose. The method can accurately and sensitively determine the lactulose content in pasteurized milk.
Description
Technical Field
The invention belongs to the field of lactulose detection, and particularly relates to a method for detecting lactulose in a dairy product.
Background
Liquid milk is usually sterilized during the production process by various heat treatments, which also destroy the nutrients. Many countries and international organizations select some indexes related to heat treatment intensity to estimate the heat damage degree of the liquid milk so as to evaluate the processing quality of the liquid milk, and lactulose is an important heat sensitive index generated in the processing process.
The existing analytical methods for lactulose mainly comprise an enzyme method, an ion chromatography and the like, and because pasteurized milk contains a lot of lactose, and the lactose and the lactulose are isomers, the difficulty of separation, qualification and quantification is increased in the measuring process of the lactulose. With the popularization of liquid chromatography tandem mass spectrometers and the continuous research and development of detection technologies in recent years, the use of liquid chromatography tandem mass spectrometers to measure lactulose has become a reality. However, the liquid chromatography tandem mass spectrometer has low sensitivity and high detection limit, and is easily interfered by lactose, and the lactulose has various optical isomers, so that the content of the lactulose cannot be accurately quantified by direct measurement.
Disclosure of Invention
The invention aims to solve the technical problem of researching and providing a method for detecting lactulose in dairy products, and the method can accurately and sensitively detect the lactulose content in the dairy products.
The invention provides the following technical scheme:
a method for detecting lactulose in dairy products comprises the following steps
(1) Taking a dairy product sample, diluting with water, adding a potassium ferrocyanide solution, a zinc sulfate solution and a phosphate buffer solution to form a sample diluent, diluting, adding beta-D-galactosidase for constant-temperature culture to obtain an enzymolysis solution, adding methanol for constant volume, adding an internal standard substance, and drying with nitrogen; adding methoxyamine solution for reaction, adding N-methyl-N-trimethylsilane trifluoroacetamide, cooling, diluting to constant volume, and removing precipitate to obtain solution to be detected;
(2) And (3) detecting and analyzing the liquid to be detected obtained in the step (1) of the detection method by using an ultra-high performance liquid chromatography tandem mass spectrometer, and calculating to obtain the lactulose content.
According to the invention, the dairy product in step (1) is pasteurized milk, UHT milk, raw milk or other dairy products; for example the milk product is pasteurized milk in liquid form.
According to the invention, in step (1), the reaction temperature after the addition of beta-D-galactosidase is 45 ℃ to 55 ℃, for example 50 ℃; the culture time is 0.5-2h, such as 1h and 1.5 h.
According to the invention, in step (1), the reaction temperature after the methoxyamine is added is 30 ℃ to 40 ℃, for example 35 ℃, 37 ℃ and the reaction time is 1 to 1.5 h.
According to the invention, in step (1), the reaction temperature after the addition of N-methyl-N-trimethylsilane trifluoroacetamide is from 30 ℃ to 40 ℃, for example 35 ℃ at 37 ℃; the reaction time is 0.5-1.5h, such as 0.5h, 1h, 1.2 h.
According to the invention, the concentration of the potassium ferrocyanide solution in the step (1) is 100-150g/L, such as 110 g/L, 120 g/L and 130 g/L, the volume ratio of the potassium ferrocyanide solution to the dairy product sample is 2 (1-5), the concentration of the zinc sulfate solution is 168 g/L, and the volume ratio of the zinc sulfate solution to the dairy product sample is 2 (1-5).
According to the invention, the volume ratio of the beta-D-galactosidase to the sample diluent in the step (1) is 1 (1-5).
According to the invention, after the methanol diluent is dried by nitrogen in the step (1), the concentration of the added methoxyamine is 10-20 mg/mL, and the volume ratio of the methoxyamine solution to the dairy product sample is (1-3): 100. in the present invention, the amount of methoxyamine added is excessive relative to lactulose in the liquid sample to be tested to ensure that the sugars in the sample are fully reacted.
According to the invention, the volume ratio of the derivatization reagent N-methyl-N-trimethyl silane trifluoroacetamide added in the step (1) to the dairy product sample is 1: 50-100.
According to the invention, the internal standard substance added in the step (1) is similar to lactulose, but does not contain substances in the sample; for example, the internal standard is xylose. In one embodiment, the amount of the internal standard is not particularly limited, and can be determined reasonably with reference to the fact that the response intensity of the internal standard on a liquid chromatography tandem mass spectrometry instrument can reach the detection limit, for example, the concentration of the internal standard in the solution to be detected is 1 to 5 μ g/mL.
According to the invention, the precipitate is removed in step (1) by filtration using a 0.22 μm organic phase filter.
In one embodiment of the present invention, the analysis conditions of the hplc-tandem mass spectrometer in step (2) are:
mobile phase: a-0.1 aqueous formic acid solution; b-acetonitrile. A: B =5: 95;
flow rate: 0.5 mL/min;
a chromatographic column: c 18 A chromatographic column;
sample introduction volume: 2 mu L of the solution;
target analyte ion pair information: 570.4 > 319.3, 570.4 > 103.1;
an ion source: electrospray (ESI +);
the scanning mode is as follows: multiple Reaction Monitoring (MRM);
spraying voltage: 4500V;
ionization temperature: 500 ℃;
de-clustering voltage: 56V.
The specification of the chromatographic column is as follows: length 75 mm x inner diameter 2.0 mm.
According to the invention, the content of lactulose in step (2) is quantified by an internal standard method.
The invention uses a high performance liquid chromatography tandem mass spectrometer to determine the content of lactulose in pasteurized milk based on the basic principle that: after proteins and fat in pasteurized milk are precipitated by inorganic salt reaction, lactose and lactulose are respectively enzymolyzed by beta-D-galactosidase to generate glucose and galactose, galactose and fructose, inorganic salt and part of glucose and galactose are separated out by methanol, internal standard is added, oximation reaction is carried out on the internal standard and methoxyamine at 37 ℃, N-methyl-N-trimethylsilane trifluoroacetamide is added for derivatization reaction, and qualitative and quantitative analysis is carried out on derivatives after the oximation reaction of fructose, so that the content of lactulose in the original pasteurized milk is obtained. Because the monosaccharide is derived Structural interconversion occurs biochemically, and to minimize or reduce this, the spatial structural distortion of the monosaccharide is reduced by an oximation reaction prior to derivatization, resulting in a relatively stable derivatized product. The derivative products of xylose, glucose, galactose and fructose in the solution to be tested are processed by C 18 After the chromatographic column is separated, the ion source and the mass analyzer are sequentially fed into the ion source and the mass analyzer, so that each substance has specific retention time and corresponding characteristic ion abundance ratio, and the purposes of separating and determining the nature of each substance are achieved. And (3) carrying out quantitative analysis by an internal standard method through scanning and integrating chromatographic peaks of the fructose derivative and the xylose derivative to obtain the concentration of the fructose derivative in the liquid to be detected, so as to obtain the content of lactulose in the pasteurized milk sample.
The invention has the beneficial effects that:
the method uses potassium ferrocyanide and zinc sulfate solution with certain concentration as a precipitating agent of protein and fat in pasteurized milk, effectively separates the protein and fat, and does not change the water phase property of the original sample.
The invention uses beta-D-galactosidase to carry out enzymolysis on the disaccharide into monosaccharide, and avoids the reality that the lactose content in pasteurized milk is too high and the lactose and lactulose can not be completely separated. By utilizing the difference of the solubility of the glucose, the galactose and the fructose in the organic reagent, partial glucose and galactose are removed, and the interference of the glucose and the galactose on the fructose in the instrumental analysis is reduced.
According to the invention, N-methyl-N-trimethylsilane trifluoroacetamide is adopted to carry out derivatization reaction on a target compound, the molecular weight of a target object to be detected is increased, a liquid to be detected is scanned by using a liquid chromatography tandem mass spectrometer, the derivative provides a larger mass-to-charge ratio, the sensitivity of parent ions is increased, the selection range of daughter ions is expanded, and qualitative and quantitative analysis on the compound is facilitated.
The oximation reaction is carried out on the methoxylamine solution dissolved in the pyridine and glucose, galactose and fructose generated after enzymolysis. The method inhibits the spatial isomerization phenomenon of monosaccharide by increasing the using amount of methoxyamine, increasing the reaction time and strictly controlling the reaction conditions, so that the products of subsequent derivatization reaction are more concentrated, and the inconvenience in detection caused by excessive derivative types is avoided.
The invention adopts xylose as an internal standard to carry out quantitative analysis on the substance to be detected. Free xylose is not found in nature, so that the pasteurized milk sample does not contain xylose background, and xylose is introduced as an internal standard substance in the detection process, so that the lactulose can be quantified more accurately.
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FIG. 1 is a chromatogram of a derivative of a glucose standard.
FIG. 2 is a chromatogram of a galactose standard substance derivative.
FIG. 3 is a chromatogram of a fructose standard derivative.
FIG. 4 is a chromatogram of a xylose standard derivative.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The materials are commercially available from the open literature unless otherwise specified.
Example 1: and adding the lactulose standard solution into the weighed fresh milk sample, and uniformly mixing to obtain the lactulose standard sample of the embodiment.
(1) Sample pretreatment
5.00 mL of lactulose spiked sample was pipetted into a 50 mL centrifuge tube, followed by addition of 5.0 mL of water, 2.0 mL of 130 g/L potassium ferrocyanide solution, 2.0 mL of 168 g/L zinc sulfate solution, and 6.0 mL of phosphate buffer (48 g/L disodium hydrogen phosphate, 8.6 g/L sodium dihydrogen phosphate, 1 g/L magnesium sulfate, pH adjusted to 7.5) in that order, and each reagent was added and mixed thoroughly by vortexing. After mixing well, centrifuging at 8000 r/min for 5min at 4 deg.C, collecting 1.0 mL supernatant, adding 4.0 mL phosphate buffer (48 g/L disodium hydrogen phosphate, 8.6 g/L sodium dihydrogen phosphate, 1 g/L magnesium sulfate, adjusting pH to 7.5), and mixing well to obtain diluted solution. Sucking 1.00 mL of diluent, adding 200 μ L of beta-D-galactosidase suspension (enzyme concentration is 40 mg/mL), slightly shaking, and performing enzymolysis reaction at 50 ℃ for 1 h to obtain an enzymolysis solution.
Taking 0.60 mL of enzymolysis liquid, diluting methanol to 5 mL, performing ultrasonic treatment for 5 min, and centrifuging at 4 deg.C at 8000 r/min for 5 min. 2.0 mL of the supernatant was added with 3.0 mL of methanol, and centrifuged at 8000 r/min at 4 ℃ for 5 min. 1.0 mL of the supernatant was taken, 50. mu.L of xylose internal standard (final xylose concentration 1. mu.g/mL) was added, and nitrogen was purged to dryness at 35 ℃. 150 μ L of a 20 mg/mL methoxyamine solution was added to the centrifuge tube and reacted at 37 ℃ for 1.5 h. After the oximation reaction, 50. mu. L N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA) was added and reacted at 37 ℃ for 0.5 h. After derivatization reaction, 0.8 mL of acetonitrile is added, the mixture is filtered through a 0.22-micron organic filter membrane, and the filtrate is collected to be detected.
(2) The analysis conditions of the ultra-high performance liquid chromatography tandem mass spectrometer are as follows:
chromatographic conditions are as follows:
mobile phase: a-0.1 aqueous formic acid; b-acetonitrile. A: B = 5: 95;
flow rate: 0.5 mL/min; a chromatographic column: c 18 A chromatographic column; sample introduction volume: 2 mu L of the solution;
mass spectrum conditions:
target analyte ion pair information: 570.4 > 319.3, 570.4 > 103.1;
an ion source: electrospray (ESI +); the scanning mode is as follows: multiple Reaction Monitoring (MRM);
spraying voltage: 4500V; ionization temperature: 500 ℃; de-clustering voltage: 56V.
The sample is subjected to a labeling recovery test by the analysis method, accurate maps and corresponding information can be obtained in each analysis, the lactulose content and related recovery information in the sample are calculated according to a standard curve obtained by analysis of a standard strain column gradient instrument (determination of the standard curve: preparation of lactulose standard solution with the concentration of 0.2, 0.4, 1.0, 2.0 and 10.0 mug/mL, the processing method is the same as that of the sample, finally, the concentration measured in the on-machine process is 8, 16, 40, 80 and 400 ng/mL through reaction and derivation, and the table 1 shows.
TABLE 1 standard recovery test results of lactulose in fresh milk
Example 2:
a pasteurized milk sample was prepared.
(1) Sample pretreatment
5.00 mL of pasteurized milk sample was taken out of a 50 mL centrifuge tube, and 5.0 mL of water, 2.0 mL of 130 g/L potassium ferrocyanide solution, 2.0 mL of 168 g/L zinc sulfate solution, and 6.0 mL of phosphate buffer (48 g/L disodium hydrogen phosphate, 8.6 g/L sodium dihydrogen phosphate, 1 g/L magnesium sulfate, pH adjusted to 7.5) were added in this order, and each reagent was added and mixed thoroughly by vortexing. After mixing, the mixture was centrifuged at 8000 r/min for 5 min at 4 ℃ to obtain 1.0 mL of supernatant, and 4.0 mL of phosphate buffer (48 g/L disodium hydrogenphosphate, 8.6 g/L sodium dihydrogenphosphate, 1 g/L magnesium sulfate, pH adjusted to 7.5) was added thereto and mixed well. 1.0 mL of the diluted solution was aspirated, 0.2 mL of a beta-D-galactosidase suspension (enzyme concentration: 40 mg/mL) was added thereto, and the mixture was gently shaken and subjected to an enzymatic reaction at 50 ℃ for 1 hour.
Taking 0.60 mL of enzymolysis liquid, diluting methanol to 5 mL, performing ultrasonic treatment for 5 min, and centrifuging at 4 deg.C at 8000 r/min for 5 min. 2.0 mL of the supernatant was added with 3.0 mL of methanol, and centrifuged at 8000 r/min at 4 ℃ for 5 min. 1.0 mL of the supernatant was taken, 50. mu.L of xylose internal standard (final xylose concentration 1. mu.g/mL) was added, and nitrogen was purged to dryness at 35 ℃. 150 mu.L of methoxyamine solution with the concentration of 20 mg/mL is added into a centrifuge tube, and oximation reaction is carried out for 1.5 h at 37 ℃. After the oximation reaction, 50. mu. L N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA) was added and reacted at 37 ℃ for 0.5 h. After derivatization reaction, 0.8 mL of acetonitrile is added, the mixture is filtered through a 0.22-micron organic filter membrane, and the filtrate is collected to be detected.
(2) The analysis conditions of the ultra-high performance liquid chromatography tandem mass spectrometer are as follows:
chromatographic conditions are as follows:
mobile phase: a-0.1 aqueous formic acid solution; b-acetonitrile. A: B = 5: 95;
flow rate: 0.5 mL/min; a chromatographic column: c 18 ChromatographyA column; sample introduction volume: 2 mu L of the solution;
mass spectrum conditions:
target analyte ion pair information: 570.4>319.3, 570.4> 103.1;
an ion source: electrospray (ESI +); the scanning mode is as follows: multiple Reaction Monitoring (MRM);
spraying voltage: 4500V; ionization temperature: 500 ℃; de-clustering voltage: 56V.
The data of the sample is analyzed by the analysis method, and the content of lactulose in the sample is calculated according to a standard curve obtained by the analysis of a standard substance series gradient instrument, and is shown in table 2.
TABLE 2 lactulose content test results in fresh milk
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (13)
1. A method for detecting lactulose in dairy products comprises the following steps:
(1) taking a dairy product sample, diluting the dairy product sample with water, adding a potassium ferrocyanide solution, a zinc sulfate solution and a phosphate buffer solution to form a sample diluent, diluting the sample diluent, adding beta-D-galactosidase to culture at constant temperature, adding methanol, centrifugally separating, taking supernatant, adding an internal standard substance, and drying by nitrogen; adding methoxyamine solution for reaction, adding N-methyl-N-trimethylsilane trifluoroacetamide, cooling, diluting to constant volume, and removing precipitate to obtain solution to be detected;
(2) detecting and analyzing the liquid to be detected obtained in the step (1) of the detection method by using an ultra-high performance liquid chromatography tandem mass spectrometer to obtain the content of lactulose;
The analysis conditions of the ultra-high performance liquid chromatography tandem mass spectrometer in the step (2) are as follows:
mobile phase: a-0.1 aqueous formic acid solution; b-acetonitrile; a: B =5: 95;
flow rate: 0.5 mL/min;
a chromatographic column: c 18 A chromatographic column;
sample introduction volume: 2 mu L of the solution;
target analyte ion pair information: 570.4 > 319.3, 570.4 > 103.1;
an ion source: electrospray (ESI +);
the scanning mode is as follows: multiple Reaction Monitoring (MRM);
spraying voltage: 4500V;
ionization temperature: 500 ℃;
de-clustering voltage: 56V;
the specification of the chromatographic column is as follows: length 75 mm x inner diameter 2.0 mm.
2. The method for detecting lactulose in dairy product according to claim 1, wherein the dairy product in step (1) is pasteurized milk, UHT milk, fresh milk or other dairy products.
3. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein in step (1), the volume ratio of beta-D-galactosidase to sample diluent is 1: 1-5.
4. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein the reaction temperature is 45-55 ℃ after the beta-D-galactosidase is added in the step (1); the culture time is 0.5-2 h.
5. The method for detecting lactulose in dairy product as claimed in claim 1 or 2, wherein the concentration of the potassium ferrocyanide solution in the step (1) is 100-150g/L, and the volume ratio of the potassium ferrocyanide solution to the dairy product sample is 2: 1-5.
6. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein the concentration of the zinc sulfate solution is 168 g/L, and the volume ratio of the zinc sulfate solution to the dairy product sample is 2: 1-5.
7. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein the concentration of the added methoxyamine after the methanol diluent is dried by nitrogen in step (1) is 10-20 mg/mL, and the amount of methoxyamine solution is excessive relative to the amount of lactulose in the solution.
8. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein in the step (1), the reaction temperature is 30-40 ℃ after the methoxylamine is added, and the reaction time is 1-1.5 h.
9. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein in the step (1), the volume ratio of the derivatization reagent N-methyl-N-trimethylsilane trifluoroacetamide added in the step (1) to the dairy product sample is 1: 50-100.
10. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein the reaction temperature is 30-40 ℃ after the N-methyl-N-trimethylsilane trifluoroacetamide is added, and the reaction time is 0.5-1.5 h.
11. The method for detecting lactulose in dairy product according to claim 1, wherein the internal standard substance added in the step (1) is xylose.
12. The method for detecting lactulose in dairy product according to claim 1, wherein the step (1) is performed by filtering to remove precipitate, and the filtering is performed by using a 0.22 μm organic phase filter membrane.
13. The method for detecting lactulose in dairy product according to claim 1 or 2, wherein the content of lactulose in step (2) is quantified by an internal standard method.
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