CN116879441A - Detection method for organic acid in food based on liquid chromatography-mass spectrometry - Google Patents
Detection method for organic acid in food based on liquid chromatography-mass spectrometry Download PDFInfo
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- 150000007524 organic acids Chemical class 0.000 title claims abstract description 118
- 235000013305 food Nutrition 0.000 title claims abstract description 49
- 238000001514 detection method Methods 0.000 title claims abstract description 40
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 title claims abstract description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000007788 liquid Substances 0.000 claims abstract description 47
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 42
- 235000005985 organic acids Nutrition 0.000 claims abstract description 40
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims abstract description 30
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000243 solution Substances 0.000 claims abstract description 30
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 28
- 239000011550 stock solution Substances 0.000 claims abstract description 25
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 24
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
- 235000002906 tartaric acid Nutrition 0.000 claims abstract description 17
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- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims abstract description 16
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims abstract description 16
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 claims abstract description 16
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 claims abstract description 16
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000015165 citric acid Nutrition 0.000 claims abstract description 16
- 239000001630 malic acid Substances 0.000 claims abstract description 16
- 235000011090 malic acid Nutrition 0.000 claims abstract description 16
- 235000004515 gallic acid Nutrition 0.000 claims abstract description 15
- 229940074391 gallic acid Drugs 0.000 claims abstract description 15
- 239000004310 lactic acid Substances 0.000 claims abstract description 15
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 15
- 239000001530 fumaric acid Substances 0.000 claims abstract description 14
- 235000011087 fumaric acid Nutrition 0.000 claims abstract description 14
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 14
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 12
- 230000005686 electrostatic field Effects 0.000 claims abstract description 12
- 239000001384 succinic acid Substances 0.000 claims abstract description 10
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 239000007864 aqueous solution Substances 0.000 claims description 19
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
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- 238000002156 mixing Methods 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- 238000007865 diluting Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
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- 238000004949 mass spectrometry Methods 0.000 claims 1
- 238000001212 derivatisation Methods 0.000 abstract description 4
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- 238000013051 Liquid chromatography–high-resolution mass spectrometry Methods 0.000 abstract description 2
- 239000006228 supernatant Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
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- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- -1 enzyme biosensors Chemical class 0.000 description 1
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Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/86—Signal analysis
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/86—Signal analysis
- G01N30/8675—Evaluation, i.e. decoding of the signal into analytical information
- G01N30/8679—Target compound analysis, i.e. whereby a limited number of peaks is analysed
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
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Abstract
The invention discloses a detection method of organic acid in food based on liquid chromatography-mass spectrometry, which belongs to the technical field of food detection and comprises the following steps: preparing a single organic acid standard stock solution; preparing a mixed organic acid stock solution; preparing 9 mixed organic acid detection methods to develop standard curve linear solutions; preparing 9 mixed organic acid detection standard curve linear solutions in food; and measuring a standard curve linear solution and a food liquid to be measured by adopting a liquid chromatograph-four-level rod electrostatic field orbit trap mass spectrometer, and respectively calculating the contents of 9 organic acids in the food. According to the invention, 9 kinds of organic acids (oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, fumaric acid, succinic acid and gallic acid) in food are quantitatively detected by adopting a liquid chromatography-high resolution mass spectrometry method, derivatization of a sample is not needed, the sensitivity is high, the detection limit is low, the accuracy is high, the stability is good, and the quantitative detection of common organic acids in food can be realized.
Description
Technical Field
The invention belongs to the technical field of food detection, and particularly relates to a detection method of organic acid in food based on liquid chromatography-mass spectrometry.
Background
Organic acids are widely present in organisms and play a key role in biological metabolic activity, participating in important metabolic pathways such as tricarboxylic acid cycle, glycolysis and gluconeogenesis. Organic acid has unique sour taste and mouthfeel, and is an important taste-developing substance in food. Different organic acids have different flavor profiles. If malic acid has lasting taste, the taste is tasty but bitter; the citric acid has soft and refreshing sour taste and short aftertaste duration; gallic acid has sour taste, and gives bitter and astringent feel when the concentration is high. In fermented foods, the metabolic activity of microorganisms and the hydrolysis of enzymes produce large amounts of organic acids, imparting a characteristic fermentation flavor to the food. In addition to organoleptic properties, organic acids have a variety of physiological activities, such as antioxidant, antibacterial and anti-inflammatory properties, and the like. The organic acid composition in the food is an important index for evaluating the flavor and the nutrition quality of the food and is also an important marker in the production process of the fermented food. Therefore, the determination of organic acids is of great importance in food processing and production, and rapid and accurate organic acid analysis means are receiving increasing attention.
At present, various analysis methods are applied to detection of organic acids, including enzyme biosensors, infrared spectroscopy, capillary electrophoresis, gas chromatography-mass spectrometry, ion chromatography, high performance liquid chromatography and the like. However, these methods have certain drawbacks, such as the enzyme biosensor method can only measure one organic acid at a time, and it is difficult to achieve the goal of simultaneously detecting multiple organic acids. When the spectrometry is used for analysis, spectrum signal interference exists among organic acids, which can influence the separation and quantification of specific organic acids and limit the application of the method in the analysis of the organic acids in complex sample matrixes. Gas chromatography is mainly used for measuring low molecular weight, volatile organic acids, and derivatization treatment is usually needed for organic acids with higher boiling points, but the derivatization process can increase operation difficulty and pretreatment time, and can cause error exacerbation, thereby limiting the application of gas chromatography and gas chromatography-mass spectrometry. Ion chromatography and high performance liquid chromatography are the most common methods for organic acid analysis, but non-specific detectors are susceptible to interference from the sample matrix, so for samples with complex matrices, relatively complex pretreatment is often required to remove the interference to ensure the sensitivity and accuracy of the analysis. Therefore, there is an urgent need to develop a more efficient detection method to realize simultaneous quantitative analysis of various organic acids in food.
Disclosure of Invention
The invention aims to provide a method for detecting organic acid in food based on liquid chromatography-mass spectrometry, which aims to solve the following technical problems: the prior art is difficult to realize simultaneous accurate quantitative analysis of various organic acids and needs derivatization before determination.
The aim of the invention can be achieved by the following technical scheme:
a detection method of organic acid in food based on liquid chromatography-mass spectrometry comprises the following steps:
step one: preparing a single standard stock solution of organic acid: respectively adding 10% methanol aqueous solution of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, fumaric acid, succinic acid and gallic acid into the mixture to dissolve and fix the volume, thus obtaining 9 single organic acid standard stock solutions;
step two: preparing a mixed organic acid stock solution: adding 10% methanol aqueous solution of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, fumaric acid, succinic acid and gallic acid into the mixture to be dissolved and fixed in volume, thus obtaining 9 mixed organic acid standard stock solutions;
step three: preparing 9 mixed organic acid detection methods to develop standard curve linear solutions: sequentially and simultaneously diluting 9 organic acids in the mixed organic acid stock solution to 5000ng/mL, 1000ng/mL, 500ng/mL, 100ng/mL and 50ng/mL by using a methanol aqueous solution with the mass fraction of 10%;
step four: mixed organic acid detection standard curve linear solutions of 9 kinds in the prepared food: sequentially and simultaneously diluting 9 organic acids in the mixed organic acid stock solution to 0.1mg/mL, 0.05mg/mL, 0.01mg/mL, 0.005mg/mL and 0.001mg/mL by using a methanol aqueous solution with the mass fraction of 10%;
step five: and measuring a standard curve linear solution and a food liquid to be measured by adopting a liquid chromatograph-four-level rod electrostatic field orbit trap mass spectrometer to obtain 9 organic acid peak areas and a standard curve equation, substituting the 9 organic acid peak areas into the standard curve equation respectively, and calculating the content of the 9 organic acids in the food respectively.
As a further aspect of the invention, the concentration of each of the 9 individual organic acid standard stock solutions in step one is 0.1mg/mL.
As a further scheme of the invention, the concentrations of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, succinic acid, gallic acid and fumaric acid in the 9 mixed organic acid standard stock solutions in the step two are all 0.1mg/mL.
As a further scheme of the invention, the food to be detected liquid comprises pear to be detected liquid, black garlic vinegar to be detected liquid and fruit and vegetable crisp chip to be detected liquid;
the pear liquid to be detected comprises the following steps:
pulverizing edible part of fructus Pyri, stirring, weighing 5g (accurate to 0.01 g) into 50mL centrifuge tube, adding ultrapure water 20mL, homogenizing and extracting in homogenizer at 10000r/min for 5min, ultrasonically extracting at 100w power for 30min, adding 20mL anhydrous alcohol, standing for 10min, centrifuging at 10000r/min for 5min, collecting supernatant, adding water to constant volume to 50mL, and filtering with 0.22 μm water phase filter membrane to obtain fructus Pyri solution to be tested;
the black garlic vinegar to-be-detected liquid comprises the following steps:
weighing 5mL (accurate to 0.01 mL) of black garlic vinegar into a 50mL centrifuge tube, adding 20mL of ultrapure water, placing the centrifuge tube into a homogenizer, homogenizing and extracting at 10000r/min for 5min, performing ultrasonic extraction at 100w power for 30min, adding 20mL of absolute ethyl alcohol, standing for 10min, centrifuging at 10000r/min by a high-speed centrifuge for 5min, taking supernatant, adding water to constant volume to 50mL, and filtering by a water phase filter membrane of 0.22 mu m to obtain black garlic vinegar to-be-detected liquid;
the fruit and vegetable crisp chip to-be-detected liquid comprises the following steps:
step 1: crushing and uniformly stirring the fruit and vegetable crisp chips, weighing 5g (accurate to 0.01 g) into a 50mL centrifuge tube, adding 20mL of ultrapure water into the centrifuge tube, placing the centrifuge tube into a homogenizer, homogenizing and extracting at 10000r/min for 5min, and centrifuging at 10000r/min by a high-speed centrifuge for 5min to obtain supernatant I and residues;
step 2: repeating the operation of the step 1 on the residues to obtain a supernatant II, mixing the supernatant I and the supernatant II, adding absolute ethyl alcohol to fix the volume to 50mL, and shaking uniformly to obtain a supernatant solution;
step 3: adding 10mL of supernatant solution into a 100mL chicken heart bottle, adding 10mL of absolute ethyl alcohol, rotating and concentrating to near dryness at 80+/-2 ℃, adding 5mL of absolute ethyl alcohol, continuously concentrating to thoroughly dry, sequentially washing the chicken heart bottle twice with 1mL of ultrapure water, transferring to a pre-activated SAX solid-phase extraction column, removing effluent liquid, eluting the purification column with 5mL of ultrapure water, eluting with 5mL of methanolic formate solution, eluting with 1mL of methanolic formate at a flow rate of 1mL/min, collecting eluent in a 50mL centrifuge tube, blowing nitrogen at 45 ℃ to near dryness, shaking and dissolving residues with 5mL of formic acid aqueous solution with a volume fraction of 0.1%, and filtering with a 0.22 mu m aqueous phase filter membrane to obtain fruit and vegetable chip to-be-detected liquid;
the methanoic acid solution in the step 3 is formic acid aqueous solution with mass fraction of 0.1 and methanol according to volume ratio of 3:97, and mixing.
As a further scheme of the invention, the chromatographic conditions of the liquid chromatograph-four-level electrostatic field orbitrap mass spectrometer are as follows: the column used was Agilent Eclipse C, 5 μm4.6 x 250mm; mixing methanol and formic acid aqueous solution with the volume fraction of 0.1% according to the volume ratio of 3:97 to obtain a mobile phase; the elution flow rate is 0.8mL/min; the column temperature is 30 ℃; the sample volume was 10. Mu.L.
As a further scheme of the invention, the mass spectrum conditions of the liquid chromatograph-four-level electrostatic field orbitrap mass spectrometer are as follows: adopting an electrospray ionization ion source ESI; the spraying voltage is 3200V; the evaporation temperature is 400 ℃; the ion transmission temperature is 500 ℃; sheath gas is 50arb; the auxiliary gas is 20arb; the scanning mode is negative ions; the scanning range is 50-750m/z.
The invention has the beneficial effects that:
the invention adopts liquid chromatography-high resolution mass spectrometry to quantitatively detect 9 organic acids (oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, fumaric acid, succinic acid and gallic acid) in food, does not need to derivatize a sample, directly adopts liquid chromatography-tandem high resolution mass spectrometry to quantitatively analyze the organic acids in the sample, and utilizes molecular ion peaks [ M-H ]] - Accurately qualitative organic acid, and extracting each organic acid [ M-H ] from total ion flow diagram] - Is a essence of (2)Mass to charge ratio (deviation)<10 ppm) was quantitatively analyzed. The quantitative detection method of the organic acid has the advantages of high sensitivity, low detection limit, high accuracy and good stability, and can realize the quantitative detection of common organic acids in foods.
Drawings
The invention is further described below with reference to the accompanying drawings.
FIG. 1 is a total ion flow diagram of a mass spectrum of 9 organic acids in example 1 of the present invention;
FIG. 2 is a mass spectrum of 9 organic acids extracted from molecular ion peaks [ M-H ] in example 1 of the present invention] - A spectrogram;
FIG. 3 is a graph of the UV detector detecting 9 organic acids;
FIG. 4 is a graph of the electrospray detector detecting 9 organic acids;
FIG. 5 shows the detection of nine organic acid spectra by the liquid chromatograph-four-level rod electrostatic field orbit trap mass spectrometer of the invention.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The embodiment of the invention uses the instrument: liquid chromatograph-four-stage rod electrostatic field orbital trap mass spectrometer (model: vanq. Mu. ish Q Exactive Pl. Mu.s), ultraviolet detector (model: waters Acq. Mu.itiv), electrospray detector (model: thermo Fisher Charged Aerosol Dectector F).
The reagents used in the examples of the present invention are shown in Table 1:
TABLE 1
In the embodiment of the invention, the organic acid content of the food liquid to be detected is calculated according to the following formula:
wherein: x: the content (mg/g) of organic acid in the food liquid to be detected; c: obtaining the concentration (mg/mL) of certain organic acid in the food test liquid according to a standard curve; v: volume of food to be measured (mL); m: the quality (g) of the food represented by the final food test solution;
in the embodiment of the invention, the organic acid standard adding recovery rate is calculated according to the following formula:
wherein: p: recovery (%); c2: a measurement value (mg/mL) of a food test solution; c1: food test solution measurement (mg/mL); and C3: scalar (mg/mL) was added.
The embodiment of the invention adopts the concentration measurement recovery rate of the organic acid with the lower limit of the standard curve quantification, namely the concentration of the standard sample of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, fumaric acid, succinic acid and gallic acid is 0.001mg/mL.
Example 1
A detection method of organic acid in food based on liquid chromatography-mass spectrometry comprises the following steps:
step one: preparing a single standard stock solution of organic acid: respectively weighing 1mg of oxalic acid, 1mg of tartaric acid, 1mg of quinic acid, 1mg of malic acid, 1mg of lactic acid, 1mg of citric acid, 1mg of fumaric acid, 1mg of succinic acid and 1mg of gallic acid (accurate to 0.01 mg) in a 25mL beaker, adding 10% methanol aqueous solution by mass fraction for dissolution, and transferring to a 10mL volumetric flask for volume fixation to prepare 9 single organic acid standard stock solutions with the concentration of 0.1 mg/mL;
step two: preparing a mixed organic acid stock solution: weighing 1mg of oxalic acid, 1mg of tartaric acid, 1mg of quinic acid, 1mg of malic acid, 1mg of lactic acid, 1mg of citric acid, 1mg of fumaric acid, 1mg of succinic acid and 1mg of gallic acid (accurate to 0.01 mg), adding 10% by mass of methanol aqueous solution for dissolution, and transferring to a 10mL volumetric flask for volume fixation to prepare 9 mixed organic acid standard stock solutions (the concentrations of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, succinic acid, gallic acid and fumaric acid solution in the 9 mixed organic acid standard stock solutions are all 0.1 mg/mL);
step three: preparing 9 mixed organic acid detection methods to develop standard curve linear solutions: sequentially and simultaneously diluting 9 organic acids in the mixed organic acid stock solution to 5000ng/mL, 1000ng/mL, 500ng/mL, 100ng/mL and 50ng/mL by using a methanol aqueous solution with the mass fraction of 10%;
step four, measuring a standard curve linear solution by adopting a liquid chromatography-four-level rod electrostatic field orbit trap mass spectrometer, wherein the chromatographic conditions are as follows: the column used was Agilent Eclipse C, 5 μm4.6 x 250mm; mixing methanol and formic acid aqueous solution with the volume fraction of 0.1% according to the volume ratio of 3:97 to obtain a mobile phase; the elution flow rate is 0.8mL/min; the column temperature is 30 ℃; the sample injection volume is 10 mu L; the mass spectrum conditions are as follows: adopting an electrospray ionization ion source ESI; the spraying voltage is 3200V; the evaporation temperature is 400 ℃; the ion transmission temperature is 500 ℃; sheath gas is 50arb; the auxiliary gas is 20arb; the scanning mode is negative ions; the scanning range is 50-750m/z; all 9 organic acids can achieve better linearity (R 2 All are larger than 0.99), and the detection limit can reach ng/mL level; obtaining molecular formula of organic acid and molecular ion peak [ M-H ]] - Retention time, linear range, regression equation, correlation coefficient R 2 The detection limit and the lower limit of the amount are shown in Table 2; and the total ion flow diagram of the mass spectrum of the 9 organic acids is drawn according to the data in the table, and the molecular ion peak [ M-H ] is extracted by the mass spectrum of the 9 organic acids as shown in the figure 1] - The spectrogram is shown in figure 2; it can be known that the liquid chromatography-four-level rod electrostatic field orbit trap mass spectrometer can detect 9 organic acids simultaneously, and can extract molecular ion peaks [ M-H ] from a total ion flow diagram for tartaric acid and quinic acid with similar retention time] - (m/z deviation)<10 ppm) to achieve the purpose of quantification, and can be used for qualitative ion detection, quantitative curve, lower detection limit and the likeThe purpose of accurate qualitative and quantitative is achieved.
TABLE 2
Example 2
A detection method of organic acid in food based on liquid chromatography-mass spectrometry comprises the following steps:
step one: mixed organic acid detection standard curve linear solutions of 9 kinds in the prepared food: sequentially and simultaneously diluting 9 organic acids in the mixed organic acid stock solution to 0.1mg/mL, 0.05mg/mL, 0.01mg/mL, 0.005mg/mL and 0.001mg/mL by using a methanol aqueous solution with the mass fraction of 10%;
step two: applying the standard curve linear solution of the condition test step two of the step four of the example 1; obtaining the molecular ion peak [ M-H ] of the organic acid] - Retention time/min, linear range/(ng/mL), regression equation, correlation coefficient R 2 Detection limit/(mg/mL) as shown in Table 3;
TABLE 3 Table 3
| Target organic acid | Linear range/(mg/mL) | Standard curve equation | Correlation coefficient R 2 |
| Oxalic acid | 0.001-0.1 | Y＝3.52e 7 +2.89e 7 X-1.10X 2 | 0.9978 |
| Tartaric acid | 0.001-0.1 | Y＝5.24e 8 +1.78e 8 X-6.58X 2 | 0.9973 |
| Quinic acid | 0.001-0.1 | Y＝5.67e 8 +1.32e 8 X-4.94X 2 | 0.9973 |
| Malic acid | 0.001-0.1 | Y＝2.79e 8 +9.84e 7 X-2.58X 2 | 0.9977 |
| Lactic acid | 0.001-0.1 | Y＝3.48e 8 +1.61e 8 X-4.34X 2 | 0.9995 |
| Citric acid | 0.001-0.1 | Y＝3.43e 8 +1.53e 8 X-4.67X 2 | 0.9981 |
| Fumaric acid | 0.001-0.1 | Y＝3.33e 7 +4.65e 7 X-1.31X 2 | 0.9998 |
| Succinic acid | 0.001-0.1 | Y＝1.92e 8 +1.23e 8 X-3.71X 2 | 0.9993 |
| Gallic acid | 0.001-0.1 | Y＝5.38e 8 +3.29e 8 X-9.58X 2 | 0.9994 |
Step three: preparing a pear to-be-detected liquid: pulverizing edible part of fructus Pyri, stirring, weighing 5g (accurate to 0.01 g) into 50mL centrifuge tube, adding ultrapure water 20mL, homogenizing and extracting in homogenizer at 10000r/min for 5min, ultrasonically extracting at 100w power for 30min, adding 20mL anhydrous alcohol, standing for 10min, centrifuging at 10000r/min for 5min, collecting supernatant, adding water to constant volume to 50mL, and filtering with 0.22 μm water phase filter membrane to obtain fructus Pyri solution to be tested;
step four, adding 0.5mL of 9 mixed organic acid detection standard curve linear solutions (the concentration is 0.1 mg/mL) into 5g of pear to-be-detected liquid to prepare a pear to-be-detected liquid, and applying the condition of the step four of the example 1 to test the pear to-be-detected liquid to detect a molecular peak [ M-H ]] - And retention time and calculate organic acid content in pear liquid to be measured, and the standard recovery rate is shown in table 4;
TABLE 4 Table 4
Example 3
A detection method of organic acid in food based on liquid chromatography-mass spectrometry comprises the following steps:
step one: preparing a black garlic vinegar to-be-detected liquid: weighing 5mL (accurate to 0.01 mL) of black garlic vinegar into a 50mL centrifuge tube, adding 20mL of ultrapure water, placing the centrifuge tube into a homogenizer, homogenizing and extracting at 10000r/min for 5min, performing ultrasonic extraction at 100w power for 30min, adding 20mL of absolute ethyl alcohol, standing for 10min, centrifuging at 10000r/min by a high-speed centrifuge for 5min, taking supernatant, adding water to constant volume to 50mL, and filtering by a water phase filter membrane of 0.22 mu m to obtain black garlic vinegar to-be-detected liquid;
step two: adding 0.5mL of 9 mixed organic acid detection standard curve linear solutions (with concentration of 0.1 mg/mL) in the step I of the example 2 into 5g of black garlic vinegar to-be-detected liquid to prepare a standard black garlic vinegar to-be-detected liquid, and detecting a molecular peak [ M-H ] by applying the condition test of the step IV of the example 1 to the standard black garlic vinegar to-be-detected liquid] - And the retention time and calculate the organic acid content and the standard recovery rate in the black garlic vinegar to be measured are shown in the table 5;
TABLE 5
Example 4
A detection method of organic acid in food based on liquid chromatography-mass spectrometry comprises the following steps:
step one: preparing a fruit and vegetable crisp chip to be measured:
step 1: crushing and uniformly stirring the fruit and vegetable crisp chips, weighing 5g (accurate to 0.01 g) into a 50mL centrifuge tube, adding 20mL of ultrapure water into the centrifuge tube, placing the centrifuge tube into a homogenizer, homogenizing and extracting at 10000r/min for 5min, and centrifuging at 10000r/min by a high-speed centrifuge for 5min to obtain supernatant I and residues;
step 2: repeating the operation of the step 1 on the residues to obtain a supernatant II, mixing the supernatant I and the supernatant II, adding absolute ethyl alcohol to fix the volume to 50mL, and shaking uniformly to obtain a supernatant solution;
step 3: adding 10mL of supernatant solution into a 100mL chicken heart bottle, adding 10mL of absolute ethyl alcohol, concentrating in a rotating way at 80+/-2 ℃ until the solution is nearly dry, adding 5mL of absolute ethyl alcohol, continuing concentrating until the solution is nearly dry, washing the chicken heart bottle twice by 1mL of ultrapure water sequentially, transferring the chicken heart bottle into a preactivated SAX solid-phase extraction column at a flow rate of 1mL/min, discarding effluent liquid, eluting a purification column by 5mL of ultrapure water, eluting by 5mL of methanoic acid solution (prepared by mixing formic acid aqueous solution with a mass fraction of 0.1 and methanol according to a volume ratio of 3:97) at a flow rate of 1mL/min, collecting eluent in a 50mL centrifuge tube, blowing nitrogen at 45 ℃ until the solution is nearly dry, oscillating dissolution residues by 5mL of methanoic acid aqueous solution with a volume fraction of 0.1%, and filtering the solution with an aqueous phase of 0.22 mu m to obtain a fruit and vegetable chip to-be-detected solution;
step two: adding 0.5mL9 mixed organic acid detection standard curve linear solutions (with concentration of 0.1 mg/mL) in the step one of the example 2 to 5g fruit and vegetable chip to-be-detected liquid to prepare a labeled fruit and vegetable chip to-be-detected liquid, and detecting molecular ion peaks [ M-H ] by applying the condition test labeled fruit and vegetable chip to-be-detected liquid in the step four of the example 1] - And the retention time and the organic acid content in the fruit and vegetable crisp chip to be detected liquid are calculated, and the standard adding recovery rate is shown in table 6;
TABLE 6
From the results in tables 4-6, it can be seen that the detection method of the invention is used for detecting the content of organic acid in food, the standard deviation of the standard addition recovery rate is more than 96%, the standard deviation is less than 4.9%, the standard addition recovery rate and the accuracy are high, the matrix interference can be eliminated, and the stability and the precision are high.
Comparing the 9 mixed organic acid detection standard curve linear solutions in step one of example 2 with the same concentration (0.05 mg/mL) by using the same chromatographic column and chromatographic conditions in step four of example 1, wherein 'v' indicates detectable and 'v' indicates undetectable; as can be seen from the spectrogram, the ultraviolet detector can only detect 5 organic acids including rt=2.75 min tartaric acid and rt=2.75 min quinine for detecting the organic acid mixed-labeling solution with the same concentrationAcid, rt=3.6 min malic acid, rt=4.7 min citric acid rt=5.8 min lactic acid; the electrospray detector can detect 8 organic acids, including rt=2.77 min oxalic acid, rt=3.02 min tartaric acid, rt=3.02 min quinic acid, rt=3.51 min malic acid, rt=5.27 citric acid, minrt=5.84 min fumaric acid, rt=6.31 min succinic acid, rt=9.93 min gallic acid. Electrospray detectors are superior to ultraviolet detectors but do not have a signal for lactic acid and cannot detect. The four-level rod electrostatic field orbit trap mass spectrum detector can detect 9 organic acids simultaneously, and can extract molecular ion peaks [ M-H ] from a total ion flow diagram for tartaric acid and quinic acid with similar retention time] - (m/z deviation)<10 ppm) to achieve the purpose of quantification, and the purposes of accurate qualitative and quantitative detection can be achieved no matter qualitative ion detection, quantitative curve, lower detection limit and the like.
TABLE 7
It is noted that relational terms such as first and second, and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. The method for detecting the organic acid in the food based on the liquid chromatography-mass spectrometry is characterized by comprising the following steps of:
step one: preparing a single standard stock solution of organic acid: respectively adding 10% methanol aqueous solution of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, fumaric acid, succinic acid and gallic acid into the mixture to dissolve and fix the volume, thus obtaining 9 single organic acid standard stock solutions;
step two: preparing a mixed organic acid stock solution: adding 10% methanol aqueous solution of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, fumaric acid, succinic acid and gallic acid into the mixture to be dissolved and fixed in volume, thus obtaining 9 mixed organic acid standard stock solutions;
step three: preparing 9 mixed organic acid detection methods to develop standard curve linear solutions: sequentially and simultaneously diluting 9 organic acids in the mixed organic acid stock solution to 5000ng/mL, 1000ng/mL, 500ng/mL, 100ng/mL and 50ng/mL by using a methanol aqueous solution with the mass fraction of 10%;
step four: mixed organic acid detection standard curve linear solutions of 9 kinds in the prepared food: sequentially and simultaneously diluting 9 organic acids in the mixed organic acid stock solution to 0.1mg/mL, 0.05mg/mL, 0.01mg/mL, 0.005mg/mL and 0.001mg/mL by using a methanol aqueous solution with the mass fraction of 10%;
step five: and measuring a standard curve linear solution and a food liquid to be measured by adopting a liquid chromatograph-four-level rod electrostatic field orbit trap mass spectrometer to obtain 9 organic acid peak areas and a standard curve equation, substituting the 9 organic acid peak areas into the standard curve equation respectively, and calculating the content of the 9 organic acids in the food respectively.
2. The method for detecting organic acids in food based on liquid chromatography-mass spectrometry according to claim 1, wherein the concentration of each of the 9 single organic acid standard stock solutions in the step one is 0.1mg/mL.
3. The method for detecting organic acid in food based on liquid chromatography-mass spectrometry (LC-MS) according to claim 1, wherein the concentrations of oxalic acid, tartaric acid, quinic acid, malic acid, lactic acid, citric acid, succinic acid, gallic acid and fumaric acid in the 9 mixed organic acid standard stock solutions in the second step are all 0.1mg/mL.
4. The method for detecting organic acid in food based on liquid chromatography-mass spectrometry (LC-MS) according to claim 1, wherein the food liquid to be detected comprises pear liquid to be detected, black garlic vinegar liquid to be detected and fruit and vegetable crisp liquid to be detected.
5. The method for detecting organic acid in food based on liquid chromatography-mass spectrometry according to claim 1, wherein the chromatographic conditions of the liquid chromatography-four-level electrostatic field orbitrap mass spectrometer are as follows: the chromatographic column adopted is Agilenteclipse 185 μm4.6 mm; mixing methanol and formic acid aqueous solution with the volume fraction of 0.1% according to the volume ratio of 3:97 to obtain a mobile phase; the elution flow rate is 0.8mL/min; the column temperature is 30 ℃; the sample volume was 10. Mu.L.
6. The method for detecting organic acid in food based on liquid chromatography-mass spectrometry according to claim 1, wherein the mass spectrometry conditions of the liquid chromatography-four-level electrostatic field orbitrap mass spectrometer are as follows: adopting an electrospray ionization ion source ESI; the spraying voltage is 3200V; the evaporation temperature is 400 ℃; the ion transmission temperature is 500 ℃; sheath gas is 50arb; the auxiliary gas is 20arb; the scanning mode is negative ions; the scanning range is 50-750m/z.
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