CN111398487A - Application method of retention index in gas chromatography-tandem mass spectrometry analysis of tobacco flavor components - Google Patents
Application method of retention index in gas chromatography-tandem mass spectrometry analysis of tobacco flavor components Download PDFInfo
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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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- G01N30/8624—Detection of slopes or peaks; baseline correction
- G01N30/8644—Data segmentation, e.g. time windows
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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
- G01N30/8665—Signal analysis for calibrating the measuring apparatus
- G01N30/8668—Signal analysis for calibrating the measuring apparatus using retention times
Abstract
The invention relates to an application method of retention index in gas chromatography-tandem mass spectrometry analysis of tobacco flavor components, which is a method for rapidly determining an acquisition time window in a gas chromatography-tandem mass spectrometry dynamic multi-reaction monitoring mode (dMRM) analysis method by utilizing the retention index, belongs to the technical field of tobacco component detection, and is characterized in that: firstly, establishing a retention index database of a target compound, and predicting the retention time of the target compound according to the actually measured retention time of the n-alkane series on the basis of obtaining the database, thereby accurately and quickly establishing a time window of each target compound in the dMRM method. The invention has the advantages of rapidness, convenience and accuracy, and greatly reduces the workload of correction of retention time.
Description
Technical Field
The invention belongs to the technical field of tobacco flavor component detection, and particularly relates to a method for rapidly determining an acquisition time window in a gas chromatography-tandem mass spectrometry (GC-MS/MS) dynamic multi-reaction monitoring mode (dMRM) analysis method by using a retention index.
Background
The tobacco flavor components comprise various volatile and semi-volatile components such as aldehyde, ketone, alcohol, phenol, acid, ether, ester, lactone, alkene, pyridine, pyrrole, pyrazine and the like. The content level and the mutual proportion of the components have key influence on the style and the quality of tobacco leaves and cigarettes, and are important chemical components influencing the aroma quality, the aroma quantity and the aroma type of the tobacco. With the advancement of analytical techniques, the influence of flavor components on the sensory quality of tobacco leaves is receiving more and more attention. However, the variability of flavour ingredient properties and the complexity of the tobacco matrix make analytical studies of its key flavour ingredients challenging. At present, gas chromatography-mass spectrometry (GC-MS) is combined with a general commercial spectrum library to analyze tobacco flavor components, the analysis method is limited by problems of sample matrix interference, insufficient GC-MS sensitivity and the like, the number of compounds capable of being accurately determined is extremely limited, and the tobacco flavor components covered by previous researches are less than one hundred. The gas chromatography-tandem mass spectrometry (GC-MS/MS) has the characteristics of high sensitivity, low detection limit, accurate qualitative determination and strong anti-interference capability, and can separate co-effluents with different parent ions, which cannot be completely separated in the chromatographic separation process, by setting a dynamic multi-reaction monitoring mode (dMRM). Compared with a GC-MS method, the method has wider compound analysis range and more compounds, and can reach more than six hundred species; corresponding quantitative ion pairs and qualitative ion pairs are selected and optimized for each compound, standard spectrum library retrieval is not needed, and the compounds are more accurate in qualitative sense; and the method has higher sensitivity and better precision and repeatability.
The qualitative basis of the dMRM mode is retention time and characteristic ion pair information of the target object, target object information is obtained by scanning the characteristic ion pair at the retention time of the target object, and the scanning range is a time window respectively established by taking the accurate retention time of each target object as the center, namely the instrument scans the characteristic ion pair of each target object only in a period of time before and after the retention time of each target object. In the multi-target analysis method, a large number of time windows are overlapped and stacked, so that the residence time of each pair of ion pairs is shortened, the data points of the acquired chromatographic peaks are reduced, and even the data cannot be acquired. Thus, to ensure that there are sufficient data points for the chromatographic peaks and sufficient residence time for each pair of ion pairs, the time window for each compound is typically minimized. In the routine laboratory test of the multi-target dMRM method, after the instrument is maintained regularly (such as replacing or cutting a chromatographic column) or when the method is transferred among different instruments, the retention time of a target object changes, the retention time of the target object deviates from a time window often, and data cannot be collected, and at the moment, the retention time of each target object needs to be determined again to create a new time window. Because many (hundreds) targets are obtained by the multi-target dMRM method and the retention time of the targets is overlapped, if the traditional method is adopted, namely a full scanning mode is adopted to determine the accurate retention time of each target, the targets need to be subjected to grouping sample injection detection (the grouping principle is that each compound in a group can be well separated, and generally one group of more than ten to twenty compounds is adopted), then the retention time of each compound is obtained finally through spectrum library retrieval and qualification, and the experimental process and data processing need to take a lot of time. The invention can quickly, conveniently and accurately obtain the accurate retention time of each target object by utilizing the retention index of each compound, thereby greatly reducing the workload of retention time correction.
The concept of Retention Index (RI) was proposed by KOVATS in 1958. The retention index represents the retention behavior of a substance on a stationary liquid, and when the stationary phase is determined, the retention index of the substance is linearly related to the column temperature and the smaller the polarity of the capillary chromatography column, the better the reproducibility of the retention index. That is, the retention index of a target is a constant related to its retention time when chromatographic conditions are determined. Because the retention index has good stability and the retention index and the retention time have a one-to-one correspondence relationship, in the multi-target GC-MS/MS method, the scanning time window of the target can be quickly adjusted by using the retention index. In the past, retention indexes are mostly applied to the auxiliary qualitative analysis of target components in a GC-MS analysis method, and the research of determining the acquisition time window of a multi-target GC-MS/MS method by utilizing the retention indexes is not reported. In view of the above problems, the invention determines the retention indexes of 241 tobacco flavor components by detecting the standard substance, and explores the application of the retention indexes in determining the GC-MS/MS method collection time window, thereby providing a reference for the rapid analysis of the tobacco flavor components.
Disclosure of Invention
The invention aims to predict the retention time of a target compound under different chromatographic conditions by using a retention index so as to quickly determine the acquisition time window of each compound in a dynamic multi-reaction monitoring mode (dMRM) of a GC-MS/MS method. The method is rapid, accurate and easy to operate, and can greatly reduce the workload of determining the retention time in the multi-target GC-MS/MS method.
The purpose of the invention is realized by the following technical scheme:
an application method of retention index in gas chromatography-tandem mass spectrometry analysis of tobacco flavor components comprises the steps of firstly establishing a retention index database of target compounds, on the basis of obtaining the database, firstly adopting the same programmed temperature rise condition to obtain actual measurement retention time of n-alkane series each time when the retention time of the target compounds is predicted, then calculating the predicted retention time of each target compound by using the retention index of each target compound and the actual measurement retention time of adjacent n-alkane, establishing a dMRM method by establishing a time window with the predicted retention time of +/-0.3 min, detecting a mixed working solution of the target compounds by using the dMRM method to obtain the actual measurement retention time of each target compound, and finally introducing the actual measurement retention time of each target compound into the dMRM method. The method comprises the following specific steps:
(1) and establishing a retention index database of the target compounds, namely acquiring the retention index of each target compound.
There are two ways to obtain the retention index, one is literature and NIST database retrieval; the other method adopts the same chromatographic column and temperature raising program in the target method, and uses n-alkane series for determination, the calculation of the target compound RI adopts the n-alkane series as reference, and the calculation formula is as follows:
in the formula: RI is the retention index of the target compound,
z is the number of carbon atoms of the adjacent normal paraffin before the target compound flows out,
t(x)is the measured retention time of the target compound,
t(z)the measured retention time of the adjacent normal paraffins before the efflux of the target compound,
t(z+1)is the measured retention time of the adjacent normal paraffin after the target compound flows out.
(2) Performing full-scan (FullScan) analysis on the normal paraffin mixed standard working solution under the same temperature programming condition to obtain the actual measurement retention time of the normal paraffin series;
(3) then, substituting the retention index of each target compound and the actually measured retention time of adjacent normal paraffin into the following formula, and calculating to obtain the predicted retention time of each tobacco flavor component;
in the formula: t is t(x)Predicted retention time for target compound
RI is retention index of target compound
z is the number of carbon atoms of the adjacent normal paraffin before the target compound flows out
t(z)Measured retention time for adjacent n-alkanes before efflux of target compound
t(z+1)Measured retention time for adjacent n-alkanes after efflux of target compound
(4) Establishing a dMRM method according to the time window established by the predicted retention time +/-0.3 min, and detecting the mixed working solution of the target compounds by using the dMRM method to obtain the actually measured retention time of each target compound;
(5) the measured retention time of each target compound may be introduced into the dMRM method.
In the invention, the target compound is a tobacco flavor component and comprises various volatile and semi-volatile flavor components such as aldehyde, ketone, alcohol, phenol, hydrocarbon, ether, ester, lactone, pyridine, pyrazine and the like.
In the invention, the normal alkane mixed standard working solution is C8～C28Or C7～C30Or C7～C40Preferably C8～C28The concentration is 5 mg/L, and the preparation solvent is n-hexane or dichloromethane.
In the invention, the GC-MS/MS analysis conditions during detection are as follows:
the gas chromatography conditions comprise that a chromatographic column is an elastic quartz capillary chromatographic column, the stationary phase is 50% phenyl-methyl polysiloxane, the specification is 60m × 0.25mm × 0.25.25 mu m, the injection port end is connected with a pre-column in series, the specification is 5m × 0.25mm, the injection port temperature is 290 ℃, the injection amount is 1 mu L, the injection mode is non-flow injection and non-flow injection time is 1min, carrier gas is helium, the constant flow mode is constant flow rate is 1.5m L/min, the temperature is programmed to rise to 75 ℃ at the initial temperature of 50 ℃ after 3min, then rise to 150 ℃ at 1 ℃ at the rate of 1 ℃ per min, then rise to 260 ℃ at the rate of 2 ℃ per min, and finally rise to 280 ℃ at the rate of 10 ℃ per min and keep for 10 min;
the mass spectrum conditions comprise an ionization mode of electron bombardment ionization with ionization energy of 70eV, a filament current of 35 muA, an ion source temperature of 280 ℃, a quadrupole rod temperature of 150 ℃, a transmission line temperature of 280 ℃, Q2 collision gas of nitrogen with purity of 99.999% and flow rate of 1.5m L/min, a quenching gas of helium with purity of 99.999% and flow rate of 2.25m L/min, and a scanning mode of a Multiple Reaction Monitoring (MRM) mode.
Compared with the prior art, the method has the following excellent effects:
because many (hundreds) targets are obtained by the multi-target dMRM method and the retention time of the targets is overlapped, if the traditional method is adopted, namely a full scanning mode is adopted to determine the accurate retention time of each target, the targets need to be subjected to grouping sample injection detection (the grouping principle is that each compound in a group can be well separated, and generally one group of more than ten to twenty compounds is adopted), then the retention time of each compound is obtained finally through spectrum library retrieval and qualification, and the experimental process and data processing need to take a lot of time. The invention can quickly, conveniently and accurately obtain the accurate retention time of each target object by utilizing the retention index of each compound, thereby greatly reducing the workload of retention time correction.
Drawings
FIG. 1: n-alkanes (C)8～C28) A total ion flow graph of the mixed standard solution;
FIG. 2: a total ion flow graph of 241 tobacco flavor components mixed with a standard solution.
Detailed Description
The invention is further described below with reference to examples, but without limiting the invention.
Example 1:
and (4) establishing a 241 tobacco flavor component retention index database.
The related tobacco flavor components comprise various volatile and semi-volatile flavor components such as aldehyde, ketone, alcohol, phenol, hydrocarbon, ether, ester, lactone, pyridine, pyrazine and the like. Under the condition of temperature programming, the target compound RI is calculated by taking the normal alkane series as reference, and the calculation formula is as follows:
in the formula: RI is the retention index of the target compound,
z is the number of carbon atoms of the adjacent normal paraffin before the target compound flows out,
t(x)is the measured retention time of the target compound,
t(z)the measured retention time of the adjacent normal paraffins before the efflux of the target compound,
t(z+1)is the measured retention time of the adjacent normal paraffin after the target compound flows out.
The GC-MS/MS analysis conditions were as follows:
the gas chromatography conditions comprise that a chromatographic column is an elastic quartz capillary chromatographic column, the stationary phase is 50% phenyl-methyl polysiloxane, the specification is 60m × 0.25mm × 0.25.25 mu m, the injection port end is connected with a pre-column (5m × 0.25mm) in series, the injection port temperature is 290 ℃, the injection amount is 1 mu L, the injection mode is that the injection is not divided and is not divided for 1min, the carrier gas is helium, the constant flow mode is that the flow rate is 1.5m L/min, the temperature is programmed to rise to the initial temperature of 50 ℃, the temperature is increased to 75 ℃ at the rate of 5 ℃/min after 3min, then the temperature is increased to 150 ℃ at the rate of 1 ℃/min, then the temperature is increased to 260 ℃ at the rate of 2 ℃/min, and finally the temperature is increased to 280 ℃.
The mass spectrum conditions comprise an ionization mode of electron bombardment ionization with ionization energy of 70eV, a filament current of 35 muA, an ion source temperature of 280 ℃, a quadrupole rod temperature of 150 ℃, a transmission line temperature of 280 ℃, Q2 collision gas of nitrogen (purity of 99.999%) with a flow rate of 1.5m L/min, a quenching gas of helium (purity of 99.999%) with a flow rate of 2.25m L/min, and a scanning mode of a Multiple Reaction Monitoring (MRM) mode.
The total ion flow graph of the normal alkane mixed standard is shown in figure 1, the measurement results of 241 tobacco flavor components RI are shown in table 1, RI and RI are respectively the temperature programming retention indexes measured in the database and the non-polar column in the NIST17 library, the difference value of the RI adopted in the database and the temperature programming RI on the non-polar column of the NIST17 library is less than 10, which shows that the target compound has good reproducibility on the non-polar column, in addition, the database is newly supplemented with 30 RI of components which are not included in the NIST17 library, wherein, some important flavor components are included, such as methyl- α -ionone, watermelon ketone, cinnamyl cinnamate, etc.
Table 1: retention index of 241 target components
Note: RI and RI are temperature programmed retention indexes measured in the database and on the nonpolar column in the NIST library respectively; "-" indicates that no listing is made in the NIST17 library
Example 2:
application of RI in GC-MS/MS analysis dynamic multiple reaction monitoring (dMRM) mode time window correction.
The dMRM mode obtains object information by scanning the characteristic ion pairs at object retention times, with the scan range being a time window created separately centered on the exact retention time of each object. In the multi-target analysis method, a large number of time windows are overlapped and stacked, so that the residence time of each pair of ion pairs is shortened, the collected chromatographic peak data points are reduced, and even the data cannot be collected. Therefore, to ensure that there are enough data points in the chromatographic peak and that each pair of ion pairs has enough residence time, the time window is generally reduced as much as possible, e.g., the time window for each target is only 0.6min in this method, i.e., the instrument scans its characteristic ion pairs only 0.3min before and after the retention time of each target. In the routine laboratory detection of the multi-target dMRM method, after the instrument is maintained regularly (such as replacing or cutting a chromatographic column) or when the instrument is transferred among different instruments in the method, the retention time of a target object can drift, and the condition that the chromatographic peak of the target object deviates from a time window and data cannot be acquired frequently occurs, so that the qualitative and quantitative results of the method are influenced. Due to the fact that the targets are numerous and the retention time is overlapped and interfered, if the accurate retention time of each target is determined by adopting a full scanning mode, grouped sample injection detection is needed, and the experimental process and data processing take long time. The invention can quickly, conveniently and accurately obtain the accurate retention time of each target object by utilizing the established RI library, thereby greatly reducing the workload of retention time correction.
The GC-MS/MS analysis conditions were as follows:
the gas chromatography conditions comprise that a chromatographic column is an elastic quartz capillary chromatographic column, the stationary phase is 50% phenyl-methyl polysiloxane, the specification is 60m × 0.25mm × 0.25.25 mu m, the injection port end is connected with a pre-column (5m × 0.25mm) in series, the injection port temperature is 290 ℃, the injection amount is 1 mu L, the injection mode is that the injection is not divided and is not divided for 1min, the carrier gas is helium, the constant flow mode is that the flow rate is 1.5m L/min, the temperature is programmed to rise to the initial temperature of 50 ℃, the temperature is increased to 75 ℃ at the rate of 5 ℃/min after 3min, then the temperature is increased to 150 ℃ at the rate of 1 ℃/min, then the temperature is increased to 260 ℃ at the rate of 2 ℃/min, and finally the temperature is increased to 280 ℃.
The mass spectrum conditions comprise an ionization mode of electron bombardment ionization with ionization energy of 70eV, a filament current of 35 muA, an ion source temperature of 280 ℃, a quadrupole rod temperature of 150 ℃, a transmission line temperature of 280 ℃, Q2 collision gas of nitrogen (purity of 99.999%) with a flow rate of 1.5m L/min, a quenching gas of helium (purity of 99.999%) with a flow rate of 2.25m L/min, and a scanning mode of a Multiple Reaction Monitoring (MRM) mode.
The specific correction method is as follows:
(1) performing full-scan (FullScan) analysis on the normal paraffin mixed standard working solution under the same temperature programming condition to obtain the actual measurement retention time of the normal paraffin series;
(2) then, substituting the retention index of each target object and the actually measured retention time of adjacent normal paraffin into the following formula, and calculating to obtain the predicted retention time of the tobacco flavor components;
in the formula: t is t(x)Predicted retention time for target compound
RI is retention index of target compound
z is the number of carbon atoms of the adjacent normal paraffin before the target compound flows out
t(z)Measured retention time for adjacent n-alkanes before efflux of target compound
t(z+1)Measured retention time for adjacent n-alkanes after efflux of target compound
(3) Establishing a dMRM method according to the time window established by the predicted retention time +/-0.3 min, and detecting the mixed working solution of the target object by using the dMRM method to obtain the actually measured retention time of each target object;
(4) the measured retention time of each target may be introduced into the dMRM method.
The exact retention time of the target that can be covered by the time window created from the predicted retention time is critical to determining whether the method is feasible. The predicted retention time and the measured retention time for each target are shown in table 2. The results show that the time difference between the predicted retention time and the actually measured retention time of 241 target objects is less than 0.3min (in this experiment, the time window is created by the predicted retention time plus or minus 0.3 min), wherein the time difference between 232 target objects is within 0.05min, and the time difference between 9 target objects is within 0.05-0.1 min. The accurate retention time for each target is within a time window created from the predicted retention time. The experimental results prove the feasibility of rapidly determining the retention time of the target by using the established RI library. The strategy can effectively shorten the working time of routine maintenance of a laboratory and solve the outstanding problems of large workload and long time consumption of correction of retention time; and by applying the strategy, a dMRM analysis method of the tobacco flavor components can be established under the condition of no standard substance.
TABLE 2241 predicted and measured Retention times for the target
Claims (5)
1. An application method of retention index in gas chromatography-tandem mass spectrometry analysis of tobacco flavor components is a method for rapidly determining an acquisition time window in a gas chromatography-tandem mass spectrometry dynamic multi-reaction monitoring mode (dMRM) analysis method by utilizing the retention index, and is characterized in that: firstly establishing a retention index database of a target compound, on the basis of obtaining the database, when predicting the retention time of the target compound each time, firstly adopting the same temperature programming condition to obtain the actual measurement retention time of a normal paraffin series, then calculating the predicted retention time of each target compound by using the retention index of each target compound and the actual measurement retention time of adjacent normal paraffin, establishing a dMRM method by establishing a time window with the predicted retention time of +/-0.3 min, detecting a mixed working solution of the target compounds by using the dMRM method to obtain the actual measurement retention time of each target compound, and finally introducing the actual measurement retention time of each target compound into the dMRM method.
2. The method of application according to claim 1, characterized in that: the method comprises the following specific steps:
(1) establishing a retention index database of the target compound;
(2) performing Full-Scan (Full Scan) analysis on the normal paraffin mixed standard working solution under the same temperature programming condition to obtain the actual measurement retention time of the normal paraffin series;
(3) then, substituting the retention index of each target compound and the actually measured retention time of adjacent normal paraffin into the following formula, and calculating to obtain the predicted retention time of each tobacco flavor component;
in the formula: t is t(x)For the predicted retention time of the target compound,
RI is the retention index of the target compound,
z is the number of carbon atoms of the adjacent normal paraffin before the target compound flows out,
t(z)the measured retention time of the adjacent normal paraffins before the efflux of the target compound,
t(z+1)the actual measurement retention time of adjacent normal paraffin after the target compound flows out;
(4) establishing a dMRM method according to the time window established by the predicted retention time +/-0.3 min, and detecting the mixed working solution of the target compounds by using the dMRM method to obtain the actually measured retention time of each target compound;
(5) the measured retention time of each target compound may be introduced into the dMRM method.
3. The method of claim 1, wherein: the target compound is a tobacco flavor component and comprises various volatile and semi-volatile flavor components such as aldehyde, ketone, alcohol, phenol, hydrocarbon, ether, ester, lactone, pyridine, pyrazine and the like.
4. The method of application according to claim 2, characterized in that: the normal alkane mixed standard working solution is C8～C28Or C7～C30Or C7～C40Preferably C8～C28The concentration is 5 mg/L, and the preparation solvent is n-hexane or dichloromethane.
5. The application method according to claim 1 or 2, characterized in that: the GC-MS/MS analysis conditions during detection are as follows:
the gas chromatography conditions comprise that a chromatographic column is an elastic quartz capillary chromatographic column, the stationary phase is 50% phenyl-methyl polysiloxane, the specification is 60m × 0.25mm × 0.25.25 mu m, the injection port end is connected with a pre-column in series, the specification is 5m × 0.25mm, the injection port temperature is 290 ℃, the injection amount is 1 mu L, the injection mode is non-flow injection and non-flow injection time is 1min, carrier gas is helium, the constant flow mode is constant flow rate is 1.5m L/min, the temperature is programmed to rise to 75 ℃ at the initial temperature of 50 ℃ after 3min, then rise to 150 ℃ at 1 ℃ at the rate of 1 ℃ per min, then rise to 260 ℃ at the rate of 2 ℃ per min, and finally rise to 280 ℃ at the rate of 10 ℃ per min and keep for 10 min;
the mass spectrum conditions comprise an ionization mode of electron bombardment ionization with ionization energy of 70eV, a filament current of 35 muA, an ion source temperature of 280 ℃, a quadrupole rod temperature of 150 ℃, a transmission line temperature of 280 ℃, Q2 collision gas of nitrogen with purity of 99.999% and flow rate of 1.5m L/min, a quenching gas of helium with purity of 99.999% and flow rate of 2.25m L/min, and a scanning mode of a Multiple Reaction Monitoring (MRM) mode.
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| RU2804172C1 (en) * | 2022-12-21 | 2023-09-26 | Общество с ограниченной ответственностью "Газпромнефть Научно-Технический Центр" (ООО "Газпромнефть НТЦ") | Method for processing chromatographic data to determine composition of hydrocarbon fluid, system and machine-readable medium for its implementation |
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