CN112903842A - Method for detecting monosaccharide - Google Patents
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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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
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Abstract
The invention discloses a method for detecting monosaccharide. The method comprises the following steps: extracting a sample to be detected to obtain an extracting solution; and carrying out high performance liquid chromatography-tandem mass spectrometry detection on the extracting solution so as to obtain the content of the monosaccharide, wherein a chromatographic column of the high performance liquid chromatography is an Acquity BEH Amide chromatographic column, and the standard is 150mm multiplied by 2.1mm and 1.7 mu m. The method utilizes high performance liquid chromatography-tandem mass spectrometry for detection, and the application of the acquisition BEH Amide chromatographic column to separate saccharide isomerate well, and has the advantages of high detection sensitivity, simple operation, high analysis speed and high result accuracy.
Description
Technical Field
The present invention relates to the field of analytical chemistry, in particular to a method for detecting monosaccharides.
Background
Polysaccharides have a wide range of physiological activities, such as: regulating immunity, resisting tumor, reducing blood lipid, and resisting aging. The composition of active polysaccharide is complex, and monosaccharide composition analysis of the active polysaccharide is of great significance for further determining the structure and the polysaccharide quality. There are many methods for measuring monosaccharide composition of polysaccharide, such as thin layer chromatography, gas chromatography, high performance capillary electrophoresis, pre-column derivatization-high performance liquid chromatography, etc., but the above methods detect a small number of monosaccharide types and have relatively low accuracy and sensitivity.
Thus, methods for detecting monosaccharides are in need of improvement.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art. Therefore, an object of the present invention is to provide a method for detecting monosaccharides, which is fast, simple and highly sensitive.
According to one aspect of the invention, there is provided a method for detecting a monosaccharide. According to an embodiment of the invention, the method comprises: extracting a sample to be detected to obtain an extracting solution; and carrying out high performance liquid chromatography-tandem mass spectrometry detection on the extracting solution so as to obtain the content of the monosaccharide, wherein a chromatographic column of the high performance liquid chromatography is an Acquity BEH Amide chromatographic column, and the standard is 150mm multiplied by 2.1mm and 1.7 mu m.
According to the method for detecting the monosaccharide, disclosed by the embodiment of the invention, the monosaccharide is detected by utilizing high performance liquid chromatography-tandem mass spectrometry, and the acquisition BEH Amide chromatographic column is applied to better separate the saccharide isomerides, so that the detection sensitivity is high, the operation is simple, the analysis speed is high, and the result accuracy is high.
In addition, the method for detecting monosaccharides according to the above embodiment of the present invention may further have the following additional technical features:
according to an embodiment of the invention, the high performance liquid chromatography is Acquity ultra performance liquid chromatography.
According to an embodiment of the invention, the mass spectrum is a triple quadrupole mass spectrum.
According to an embodiment of the present invention, the mobile phase of the high performance liquid chromatography is: a: 10mM ammonium formate solution, B: containing 10mM ammonium formate-acetonitrile solution.
According to an embodiment of the invention, the gradient elution procedure: 10-20% A (0-7.5 min); 20-40% A (7.5-9.5 min); 40-10% A (9.5-9.51 min); 10% A (9.51-13 min).
According to an embodiment of the present invention, the chromatographic conditions of the high performance liquid chromatography are: the flow rate is 0.2 mL/min; the sample injection amount is 5 mu L; the column temperature was 30 ℃.
According to an embodiment of the invention, the mass spectral conditions of the mass spectrum are: an electrospray ion (ESI) source; the ion source temperature is 500 ℃; the scanning mode is as follows: a negative ion mode; atomizing gas GS1 pressure 55 ℃; the pressure of auxiliary gas GS2 is 60 ℃; ion source spray voltage: -5.5 kV; inlet voltage: -10V; outlet voltage: 13V.
According to an embodiment of the present invention, the monosaccharides include mannitol, fucose, rhamnose, arabinose, galactose, glucose, xylose, mannose, ribose, fructose, galacturonic acid, glucuronic acid and sucrose.
Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
Drawings
The above and/or additional aspects and advantages of the present invention will become apparent and readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings of which:
FIG. 1 shows a schematic chromatographic diagram of a set of isomers of galactose, mannose, glucose and fructose in different stationary phases according to one embodiment of the invention, wherein A is an XBridge Amide chromatographic column; b is an Acquity BEH HILIC chromatographic column; c is Inertsutain NH2A chromatographic column; d is an Acquity BEH chromatographic column;
FIG.2 shows a schematic diagram of the chromatography of a set of isomers of galactose, mannose, glucose and fructose in different mobile phases, wherein a is 10mM ammonium formate-acetonitrile containing 10mM ammonium formate, according to an embodiment of the present invention; b is 0.1% ammonia water-acetonitrile solution containing 0.1% ammonia water; c is 10mM ammonium acetate-acetonitrile solution containing 10mM ammonium acetate;
FIG. 3 shows a schematic of the total ion flux of 13 saccharide compounds according to one embodiment of the present invention, wherein 1. ribose; 2. xylose; 3. arabinose; 4. fucose; 5. rhamnose; 6. mannitol; 7. mannose; 8. fructose; 9. glucose; 10. galactose; 11. sucrose; 12. galacturonic acid; 13. glucuronic acid.
Detailed Description
Reference will now be made in detail to embodiments of the present invention, examples of which are illustrated in the accompanying drawings, wherein like or similar reference numerals refer to the same or similar elements or elements having the same or similar function throughout. The embodiments described below with reference to the accompanying drawings are illustrative only for the purpose of explaining the present invention, and are not to be construed as limiting the present invention.
In the description of the present invention, the terms "longitudinal", "lateral", "upper", "lower", "front", "rear", "left", "right", "vertical", "horizontal", "top", "bottom", and the like indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, which are for convenience of description of the present invention only and do not require that the present invention must be constructed and operated in a specific orientation, and thus, should not be construed as limiting the present invention.
It should be noted that the terms "first" and "second" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include one or more of that feature. Further, in the description of the present invention, "a plurality" means two or more unless otherwise specified.
According to one aspect of the invention, there is provided a method for detecting a monosaccharide. According to an embodiment of the invention, the method comprises: extracting a sample to be detected to obtain an extracting solution; and carrying out high performance liquid chromatography-tandem mass spectrometry detection on the extracting solution so as to obtain the content of the monosaccharide, wherein a chromatographic column of the high performance liquid chromatography is an Acquity BEH Amide chromatographic column, and the standard is 150mm multiplied by 2.1mm and 1.7 mu m.
According to the method for detecting the monosaccharide, disclosed by the embodiment of the invention, the monosaccharide is detected by utilizing high performance liquid chromatography-tandem mass spectrometry, and the acquisition BEH Amide chromatographic column is applied to better separate the saccharide isomerides, so that the detection sensitivity is high, the operation is simple, the analysis speed is high, and the result accuracy is high.
According to an embodiment of the invention, the high performance liquid chromatography is Acquity ultra performance liquid chromatography. Thus, the sensitivity and accuracy of detection are high.
According to an embodiment of the invention, the mass spectrum is a triple quadrupole mass spectrum. Thus, the sensitivity and accuracy of detection are high.
According to an embodiment of the present invention, the mobile phase of the high performance liquid chromatography is: a: 10mM ammonium formate solution, B: containing 10mM ammonium formate-acetonitrile solution. Therefore, the separation effect of the monosaccharide is good, and peaks are easy to appear.
According to an embodiment of the invention, the gradient elution procedure: 10-20% A (0-7.5 min); 20-40% A (7.5-9.5 min); 40-10% A (9.5-9.51 min); 10% A (9.51-13 min). Therefore, the monosaccharide separation effect is good, the peak time is appropriate, and the peak shape is good. Thus, the sensitivity and accuracy of detection are high.
According to an embodiment of the present invention, the chromatographic conditions of the high performance liquid chromatography are: the flow rate is 0.2 mL/min; the sample injection amount is 5 mu L; the column temperature was 30 ℃. Thus, the sensitivity and accuracy of detection are high.
According to an embodiment of the invention, the mass spectral conditions of the mass spectrum are: an electrospray ion (ESI) source; the ion source temperature is 500 ℃; the scanning mode is as follows: a negative ion mode; atomizing gas GS1 pressure 55 ℃; the pressure of auxiliary gas GS2 is 60 ℃; ion source spray voltage: -5.5 kV; inlet voltage: -10V; outlet voltage: 13V. Thus, the sensitivity and accuracy of detection are high.
The detection method of the embodiment of the invention can detect various polysaccharides, and according to the embodiment of the invention, the monosaccharide comprises mannitol, fucose, rhamnose, arabinose, galactose, glucose, xylose, mannose, ribose, fructose, galacturonic acid, glucuronic acid and sucrose.
The present invention is described below with reference to specific examples, which are intended to be illustrative only and are not to be construed as limiting the invention.
The scheme of the invention will be explained with reference to the examples. It will be appreciated by those skilled in the art that the following examples are illustrative of the invention only and should not be taken as limiting the scope of the invention. The examples, where specific techniques or conditions are not indicated, are to be construed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or apparatus used are conventional products which are commercially available, e.g. from Sigma, without reference to the manufacturer.
Example 1
The monosaccharide detection method provided by the embodiment of the invention is used for detecting and verifying the monosaccharide 13, and comprises the following specific steps:
1. solution preparation
1.1 preparation of Standard solution
Rhamnose, xylose, fucose, mannose, galactose, ribose, arabinose, fructose, glucose, mannitol, sucrose, glucuronic acid, galacturonic acid standard stock (1000 mg/L): accurately weighing 10.0mg of standard substance, respectively dissolving with ultrapure water, diluting to 10mL, and storing at low temperature. Standard stock solutions were reconstituted once a month. And the standard working solution of rhamnose, xylose, fucose, mannose, galactose, ribose, arabinose, fructose, glucose, mannitol, sucrose, glucuronic acid and galacturonic acid is diluted by water and acetonitrile solution with volume fraction of 50% into a series of standard working solutions with mass concentration and is stored at low temperature.
1.2 preparation of leacheate
0.1mol/L NaOH solution: 5.2mL of 50% NaOH solution was added to a plastic reagent bottle containing 989.6mL of ultrapure water, and the mixture was shaken well after being purged with nitrogen.
0.4mol/L NaAc solution: 16.4g of sodium acetate solid was weighed, dissolved in water and diluted to 0.5L, and filtered through a 0.22 μm filter for use.
1.3 preparation of the Mobile phase
10mmol/L ammonium formate solution: accurately weighing 0.63g of ammonium formate solid, diluting with deionized water and metering to 1L as a mobile phase.
10mmol/L ammonium formate-acetonitrile solution: accurately weighing 0.63g of ammonium formate solid, adding 1mL of deionized water for dissolving, and using acetonitrile to fix the volume to 1L to be used as a mobile phase.
10mmol/L ammonium acetate solution: 0.77g of ammonium acetate solid was weighed out accurately, diluted with deionized water and made up to 1L as mobile phase.
10mmol/L ammonium acetate-acetonitrile solution: 0.77g of ammonium acetate solid is accurately weighed, 1mL of deionized water is added for dissolution, and acetonitrile is used for constant volume till 1L is used as a mobile phase.
0.1% aqueous ammonia solution: exactly 1mL of aqueous ammonia was removed and added to 999mL of deionized water as the mobile phase.
0.1% ammonia-acetonitrile solution: 1mL of aqueous ammonia solution was accurately removed and added to 999mL of acetonitrile solution as a mobile phase.
2. Conditions of the experiment
2.1 UPLC-MS/MS experiment conditions
Chromatographic conditions are as follows: a chromatographic column: acquisty BEHAmide (150 mm. times.2.1 mm, 1.7 μm); mobile phase: 10mM ammonium formate solution (mobile phase A) and a solution containing 10mM ammonium formate-acetonitrile (mobile phase B); gradient elution procedure: 10-20% A (0-7.5 min); 20-40% A (7.5-9.5 min); 40-10% A (9.5-9.51 min); 10% A (9.51-13 min); the flow rate is 0.2 mL/min; the sample injection amount is 5 mu L; the column temperature is 30 ℃; run time 13 min.
Mass spectrum conditions: an electrospray ion (ESI) source; the ion source temperature is 500 ℃; the scanning mode is as follows: a negative ion mode; atomizing gas GS1 pressure 55 ℃; the pressure of auxiliary gas GS2 is 60 ℃; ion source spray voltage: -5.5 kV; inlet voltage: -10V; outlet voltage: 13V. The mass spectrometric parameters of the 13 sugars are shown in table 1.
TABLE 113 sugar UPLC-MS/MS methods for monitoring ion-pair, declustering voltage and collisional gas energy
Is a quantitative ion
2.2 methodological investigation
2.2.1 Linear relationship, detection Limit (LOD) and quantitation Limit (LOQ)
Linear relation, LOD and LOQ of the PLC-MS/MS method are diluted by a 50% acetonitrile ammonium formate solution by adopting a stepwise dilution method to prepare a mixed standard solution of 13 kinds of carbohydrate compounds with mass concentrations of 0.01, 0.05, 0.1, 0.5, 1, 2, 5 and 10 mg/L. And repeatedly injecting mixed standard solutions with different concentrations for 6 times to obtain a standard curve. The detection limit and the quantification limit of the method are obtained by gradually diluting the standard solution.
2.2.2 in-day and in-day precision tests
The precision in the day is measured by taking three parts of the same sample solution, adding reference substances according to the monosaccharide content of about 50%, 100% and 150%, and using the reference substances as low, medium and high concentration adding marks. Since the actual sample of spirulina does not contain three kinds of saccharide compounds of mannitol, mannose and sucrose, the addition of the compound is carried out at concentrations of 1, 2 and 4 times of the highest limit of quantitation of each compound when the standard is added, the content of each monosaccharide is measured within one day according to the UPLC-MS/MS method, and RSD (%) is calculated.
The precision in the daytime is measured by taking three parts of the same test solution, adding reference substances according to the content of each monosaccharide of about 50%, 100% and 150%, and using the reference substances as low, medium and high concentration adding marks. Since the actual sample of spirulina does not contain three kinds of sugar compounds of mannitol, mannose and sucrose, the addition of the standard is carried out at concentrations of 1, 2 and 4 times the maximum limit of the amount of each compound in the three methods, and the content of each monosaccharide is measured in five days according to the above UPLC-MS/MS method to calculate RSD (%).
2.2.3 method repeatability examination
And taking 5 parts of the same sample powder, performing ultrasonic extraction, purification and standard addition, and determining according to the analysis conditions.
2.2.4 test of stability of test solution
Hydrolyzing the same polysaccharide, adding standard solution, and measuring at 0, 2, 4, 6, 8, and 10 hr according to the above analysis conditions.
2.2.5 spiking recovery Studies
Taking 3 parts of spirulina powder with known sugar content, adding reference substances according to the content of 50%, 100% and 150% of various sugars, and marking as low, medium and high concentrations. Because the actual sample of the spirulina does not contain three kinds of carbohydrate compounds, namely mannitol, mannose and sucrose, the three kinds of carbohydrate compounds are added according to the concentrations which are 1, 2 and 4 times of the highest quantitative limit of each compound in the three methods when the standard is added. And then, according to the three methods of HPAEC-PAD, HPAEC-MS and UPLC-MS/MS, measuring the monosaccharide content and calculating the sample loading recovery (%).
3. Results and discussion
3.1 selection of chromatography columns
Since most carbohydrate compounds are highly hydrophilic and there are many isomers, the study contains 4 sets of isomers, one set of mannose, galactose, glucose and fructose, one set of fucose and rhamnose, one set of arabinose, xylose and ribose, one set of glucuronic acid and galacturonic acid, and the effects of 4 chromatographic columns on the separation of 13 carbohydrate compounds, including XBridge Amide (150mm x 4.6mm, 3.5 μm) (fig.2-6A), Acquity BEH HILIC (50mm x 2.1mm, 1.7 μm) (fig.2-6B), inertnstatin NH, are compared, limited by their structures2(100 mm. times.2.1 mm, 3 μm) (FIG.2-6C) and Acquity BEH Amide (100 mm. times.2.1 mm, 1.7 μm) (FIG.2-6D), which are separation modes based on HILIC. The results are shown in FIG. 1. The group of isomers of galactose, mannose, glucose and fructose is taken as an example. Inertsutain NH2The four column components are not completely separated, which may be due to the Schiff base reaction of the carbonyl groups contained in the sugars with the ammonia bound to the column, resulting in a decrease in the separation capacity of the column. Acquity BEH HILIC can promote the retention of polar compounds under appropriate mobile phase, flow rate, column temperature and pH, and in this experiment, four isomers are not separated even under optimal conditions. Compared with the Acquity BEH Amide, the XBridge Amide chromatographic column has the advantages that four isomers are separated, but the XBridge Amide chromatographic column has the problems of poor peak shape and poor repeatability, and even if fructose and glucose do not achieve baseline separation on the Acquity BEH Amide chromatographic column, the Acquity BEH Amide chromatographic column has better separation on saccharide isomers compared with other three chromatographic columns, so that the Acquity BEH Amide is selected as a stationary phase for chromatographic separation in the embodiment of the invention.
3.2 selection of buffer salts in the mobile phase
The addition of some additives in the mobile phase can improve the peak shape of the chromatographic peak and avoid ion inhibition. Three additives, namely ammonium formate, ammonia water and ammonium acetate, are selected in the experiment, and the influence of the additives on separation is inspected. The results are shown in FIG.2, which exemplifies a group of isomers of galactose, mannose, glucose, and fructose. The three additives have great influence on the separation effect of the four sugars, and when the additive is ammonia water, mannose and fructose are not well separated and peak appearance is slow. When the additive is ammonium acetate, only three peaks appear, and the peaks are wide. When the additive is ammonium formate, the four sugars are separated. Therefore, ammonium formate was chosen as the buffering salt in the mobile phase for this experiment.
3.3 optimization of Mass Spectrometry conditions
The optimal mass spectrum parameters of each sugar obtained by optimizing the mass spectrum conditions through needle pump sample injection are shown in tables 2-6. In the process of scanning parent ions by needle pump sample injection, 1mg/L of sugar standard solution is injected, and the parent ions cannot be found by changing mass spectrum parameters. Parent ions are found when 10mg/L of sugar standard substance is injected by a needle pump, which shows that the ionization effect of sugar is not good, and the detection sensitivity can be reduced.
After mass spectrum conditions and chromatographic conditions are optimized, a total ion flow diagram of 13 kinds of carbohydrate compounds is obtained, and is shown in figure 3.
4 methodological investigation
4.1 UPLC-MS/MS method Linear relationship, LOD and LOQ
Taking a mixed standard solution of 13 kinds of carbohydrate, diluting the mixed standard solution to 0.01, 0.05, 0.1, 0.5, 1, 2, 5 and 10mg/L step by step, and measuring by adopting an HPAEC-MS method, wherein the result shows that the R of the 13 kinds of carbohydrate is in the range of 0.2-15 mg/L2The linear relation is good if the linear relation is more than 0.999, the detection limit of the method is between 0.02 and 1.50 mu g/L, the quantification limit is between 0.20 and 5.50 mu g/L, and the method has good sensitivity. The results are shown in Table 2.
TABLE 2 UPLC-MS/MS method Linear relationship, LOD and LOO for 13 saccharides
4.2 Intra-day precision and inter-day precision
Daytime precision and intra-day precision are expressed as Relative Standard Deviation (RSD) of the method. The results of the measurement according to the above method showed that the RSD was less than 5% and the precision was good in both daytime and intraday (Table 3).
TABLE 3 results of precision test
4.3 method repeatability test
After 5 parts of the same sample powder is taken, subjected to ultrasonic extraction, purification and standard addition, and determined according to analysis conditions of three methods, namely HPAEC-PAD, HPAEC-MS and UPLC-MS/MS, and calculated according to the content of 10 carbohydrate compounds, the RSD of the three analysis methods is respectively 3.5-4.9%, 2.5-5.0% and 2.8-4.7%, which shows that the method has good repeatability (Table 4).
Table 4 results of repetitive tests (n ═ 5)
4.4 spiking recovery Studies
The result of the standard addition recovery rate experiment shows that (table 5), under the condition of adding the standard at three concentration levels, the monosaccharide recovery rate is 80.21-121.67%, 83.20-119.34% and 80.21-125.51%, and the method is good in accuracy and can be used for measuring the content of the carbohydrate.
Table 5 recovery test results (n ═ 3)
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
While embodiments of the invention have been shown and described, it will be understood by those of ordinary skill in the art that: various changes, modifications, substitutions and alterations can be made to the embodiments without departing from the principles and spirit of the invention, the scope of which is defined by the claims and their equivalents.
Claims (8)
1. A method for detecting a monosaccharide, comprising:
extracting a sample to be detected to obtain an extracting solution;
and (3) carrying out high performance liquid chromatography-tandem mass spectrometry detection on the extracting solution so as to obtain the content of the monosaccharide, wherein a chromatographic column of the high performance liquid chromatography is an Acquity BEHAmide chromatographic column, and the specification is 150mm multiplied by 2.1mm and 1.7 mu m.
2. The method of claim 1, wherein the high performance liquid chromatography is Acquity ultra high performance liquid chromatography.
3. The method of claim 1, wherein the mass spectrometry is triple quadrupole mass spectrometry.
4. The method of claim 2, wherein the mobile phase of the high performance liquid chromatography is: a: 10mM ammonium formate solution, B: containing 10mM ammonium formate-acetonitrile solution.
5. The method of claim 4, wherein the gradient elution procedure: 10-20% A (0-7.5 min); 20-40% A (7.5-9.5 min); 40-10% A (9.5-9.51 min); 10% A (9.51-13 min).
6. The method of claim 2, wherein the chromatographic conditions of the high performance liquid chromatography are:
the flow rate is 0.2 mL/min;
the sample injection amount is 5 mu L;
the column temperature was 30 ℃.
7. The method of claim 3, wherein the mass spectrometry conditions of the mass spectrometer are:
an electrospray ion (ESI) source;
the ion source temperature is 500 ℃;
the scanning mode is as follows: a negative ion mode;
atomizing gas GS1 pressure 55 ℃;
the pressure of auxiliary gas GS2 is 60 ℃;
ion source spray voltage: -5.5 kV;
inlet voltage: -10V;
outlet voltage: 13V.
8. The method of claim 1, wherein the monosaccharides include mannitol, fucose, rhamnose, arabinose, galactose, glucose, xylose, mannose, ribose, fructose, galacturonic acid, glucuronic acid and sucrose.
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