CN111208310B - GC-QTOF detection method for aldehyde ketone fragrance components in tobacco and tobacco products - Google Patents
GC-QTOF detection method for aldehyde ketone fragrance components in tobacco and tobacco products Download PDFInfo
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- CN111208310B CN111208310B CN202010017194.1A CN202010017194A CN111208310B CN 111208310 B CN111208310 B CN 111208310B CN 202010017194 A CN202010017194 A CN 202010017194A CN 111208310 B CN111208310 B CN 111208310B
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- G—PHYSICS
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- 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
A GC-QTOF detection method for aldehyde ketone fragrance components in tobacco and tobacco products comprises the steps of firstly establishing 127 aldehyde ketone fragrance component databases including a first-level full-scan mass spectrogram, retention time, fragment ion accurate mass, ion abundance ratio and retention index calculated by taking normal alkane series as reference of each aldehyde ketone fragrance component; secondly, carrying out primary full scanning on a tobacco sample to be detected to obtain primary full scanning data of the sample; and finally, accurately quantifying the sample measurement result by adopting a database, and accurately quantifying aldehyde-ketone fragrance components meeting qualitative conditions by using quantitative software. The method can be used for identifying aldehyde ketone fragrance components by matching an actual mass spectrogram with a high-resolution mass spectrogram, and can be used for accurately extracting quality by setting a target source as an established aldehyde ketone fragrance component database, and taking more than two characteristic ions as qualitative basis, wherein the abundance ratio and retention time/index of the characteristic ions are consistent with those in the database.
Description
Technical Field
The invention belongs to the technical field of tobacco analysis, and particularly relates to a GC-QTOF detection method for 127 aldehyde ketone fragrance components in tobacco and tobacco products.
Background
Aldehyde ketone compounds in tobacco are important flavor components, and are closely related to the sensory quality and flavor of tobacco. Gas chromatography-mass spectrometry (GC-MS) is the most commonly used method for analyzing volatile and semi-volatile components in tobacco samples, but due to the complexity of tobacco sample matrix, the qualitative and quantitative results may be inaccurate due to interference of characteristic ions or low content of target substances. In addition, with conventional GC-MS analysis, aldehyde ketone fragrance ingredient standards are required to be characterized in comparison, and once the column is replaced, the retention time of the compound can drift, and the standard needs to be reused to determine the retention time. In actual work, most laboratories are high in price, short in effective period and not easy to store because of the fragrance component standard substances, and high-flux, accurate, qualitative and quantitative analysis of aldehyde ketone fragrance components in samples cannot be realized by general laboratories. The GC-QTOF method is adopted in the method for screening and quantitatively determining the pesticide residues in tobacco by combining filter head type solid phase extraction with GC-QTOF/MS and the GC-Q-TOF/MS detection technology of 708 pesticide residues in solanaceous vegetables, so that the pesticide residues in complex samples can be screened and detected, the accurate qualitative determination of the pesticide residues without standard substance contrast is realized, but the GC-QTOF analysis method of aldehyde ketone fragrance components in tobacco has not been reported at present.
Disclosure of Invention
The invention aims to establish a rapid detection method for 127 aldehyde ketone fragrance components in tobacco and tobacco products. The method realizes the rapid detection of 127 aldehyde ketone fragrance components in the tobacco and tobacco products without standard substance comparison, and meets the requirement of high-flux rapid and accurate detection of the aldehyde ketone fragrance components in the current tobacco and tobacco products.
The aim of the invention is realized by the following technical scheme:
a GC-QTOF detection method for aldehyde ketone fragrance components in tobacco and tobacco products comprises the steps of firstly establishing 127 aldehyde ketone fragrance component databases including a first-level full-scan mass spectrogram, retention time, fragment ion accurate mass, ion abundance ratio and retention index calculated by taking normal alkane series as reference of each aldehyde ketone fragrance component; secondly, carrying out primary full scanning on tobacco and tobacco product samples to be detected to obtain primary full scanning data of the samples; and finally, accurately quantifying the sample measurement result by adopting a database, and accurately quantifying aldehyde-ketone fragrance components meeting qualitative conditions by using quantitative software. The method comprises the following specific steps:
(1) Preparing an aldehyde ketone fragrance ingredient standard substance into a standard solution of 1-5 mug/mL, carrying out GC-QTOF first-order full-scan analysis under set conditions to obtain a first-order full-scan mass spectrogram, retention time, fragment ion accurate mass and ion abundance ratio of each aldehyde ketone fragrance ingredient, and calculating a retention index of a target compound by taking normal alkane series as a reference;
(2) Leading the first-stage full-scan data, the retention index and the high-resolution first-stage full-scan mass spectrogram matched with NIST17 obtained in the step (1) into PCDL software, correlating the PCDL software with corresponding aldehyde ketone fragrance component information, and establishing an accurate quality database; optimizing a quality extraction window;
(3) Preparing 127 standard curves of aldehyde ketone fragrance components to d 8 Acetophenone is an internal standard to correct the instrument response;
(4) Carrying out primary full scanning on the tobacco and tobacco product samples under the same set conditions as in the step (1) to obtain primary full scanning data of the tobacco and tobacco product samples;
(5) And (3) accurately quantifying the sample measurement result by adopting a database, and accurately quantifying aldehyde-ketone fragrance components meeting qualitative conditions by using quantitative software.
In the invention, aldehyde ketone fragrance components meeting qualitative conditions are qualitatively determined by the following method; the database is set as a target source, the mass extraction window is 3-10 mDa, more than two characteristic ions are accurately detected, and the abundance ratio and retention time/index of the characteristic ions are consistent with those in the database to serve as qualitative basis.
The tobacco and the tobacco products comprise tobacco leaves, cut tobacco of cigarettes, cut tobacco of heating non-burning cigarettes and buccal cigarettes.
The sample pretreatment mode related in the step (4) is to weigh 1-5 g of tobacco and tobacco product samples, add 5-50 mL of phosphate buffer solution to adjust the pH value to 1-5, foam for 3-10 min, add 10-30 mL of acetonitrile and 20-100 mu L of 30.0mg/L d 8 -acetophenone internal standard working solution, then vortex, centrifuge and dry in sequence, and take supernatant fluid to pass through 0.22 μm organic phase filter membrane.
The mass spectrum chromatographic conditions in the GC-QTOF detection are: chromatographic column: DB-5MS UI elastic quartz capillary chromatographic column (60 m x 0.25mm x 0.25 μm), sample inlet end series pre-column (5 m x 0.25 mm); carrier gas: high purity He, purity 99.999%; constant flow mode, flow rate: 1.5mL/min; sample inlet temperature: 290 ℃; sample injection mode: sample introduction without diversion; sample injection amount: 0.8. Mu.L; heating program: the initial temperature is 50 ℃, the temperature is kept for 3min, then the temperature is increased to 75 ℃ at 5 ℃/min for 1min, then the temperature is increased to 150 ℃ at 1 ℃/min for 1min, then the temperature is increased to 260 ℃ at 2 ℃/min for 1min, and finally the temperature is increased to 290 ℃ at 10 ℃/min for 10min;
ion source: electron bombardment (EI); electron energy: 70eV; ion source temperature: 230 ℃; transmission line temperature: 280 ℃; mass analyzer: four-stage stick-time of flight; scanning mode: primary full scanning; mass scan range: 20 to 300amu.
The specific names of the 127 aldehyde ketone fragrance components are shown in table 1:
table 1 database of 127 aldehyde ketone fragrance composition information
Compared with the existing detection method, the method has the following advantages:
1. according to the invention, on one hand, the aldehyde ketone fragrance components can be identified through matching of an actual mass spectrogram and a high-resolution mass spectrogram, on the other hand, the target source is set to be an established aldehyde ketone fragrance component database, the mass extraction window is 3-10 mDa, accurate mass extraction is carried out, more than two characteristic ions are accurately detected, the abundance ratio and retention time/index of the characteristic ions are consistent with those in the database as qualitative basis, and compared with the traditional GC-MS, the invention can be used for more accurately determining and quantifying the aldehyde ketone fragrance components in tobacco and tobacco products.
2. The invention calculates the retention index of 127 aldehyde ketone fragrance components by taking normal alkane as a reference series, combines an aldehyde ketone fragrance component database, realizes the accurate qualitative determination of 127 aldehyde ketone fragrance components on the premise of not needing standard substance comparison, and can save the cost of purchasing standard substances.
3. The GC-QTOF detection method is simple and convenient in data acquisition in a primary full-scanning mode, is not limited by a scanning time period and the number of scanning ions, and can acquire all information of a sample for data archiving. During the later data processing, the corresponding qualitative and quantitative methods can be edited according to different requirements to analyze the sample.
Drawings
Fig. 1: mass spectrogram examples of phenylacetaldehyde (a) and salicylaldehyde (b) in the database.
Fig. 2: in cut tobacco sample a, 20.59 minutes of mass spectrum (a 20.59 minutes of complete mass spectrum, b partial mass spectrum with abundance lower than 1000).
Fig. 3: extracting an ion flow diagram from characteristic ions of phenylacetaldehyde in a tobacco shred sample A.
Fig. 4: and extracting an ion flow diagram from characteristic ions of salicylaldehyde in the tobacco shred sample A.
Fig. 5: and extracting an ion flow diagram of the 2-acetyl-5-methylfuran in a GC-QTOF full scanning mode when the mass window is 0.5 Da.
Fig. 6: and extracting an ion flow diagram when the mass window of the 2-acetyl-5-methylfuran is 3-10 mDa in a GC-QTOF full scanning mode.
Detailed Description
The invention is further described below with reference to the following examples of drawings:
the invention relates to a GC-QTOF detection method for aldehyde ketone fragrance components in tobacco and tobacco products, which comprises the following specific steps: (1) Preparing 127 aldehyde ketone fragrance ingredient standard substances into a standard solution with the concentration of 1-5 mug/mL, carrying out GC-QTOF first-order full-scan analysis under set conditions to obtain a first-order full-scan mass spectrogram, retention time, fragment ion accurate mass and ion abundance ratio of each aldehyde ketone fragrance ingredient, and calculating the retention index of a target compound by taking normal alkane series as a reference;
(2) Leading the first-stage full-scan data, the retention index and the high-resolution first-stage full-scan mass spectrogram matched with NIST17 obtained in the step (1) into PCDL software, correlating the PCDL software with corresponding aldehyde ketone fragrance component information, and establishing an accurate quality database; optimizing a quality extraction window;
(3) Preparing 127 standard curves of aldehyde ketone fragrance components to d 8 Acetophenone is an internal standard to correct the instrument response;
(4) Carrying out primary full scanning on the tobacco and tobacco product samples under the same set conditions as in the step (1) to obtain primary full scanning data of the tobacco and tobacco product samples;
(5) And (3) accurately quantifying the sample measurement result by adopting a database, and accurately quantifying aldehyde-ketone fragrance components meeting qualitative conditions by using quantitative software.
Example 1
(1) 1-5 g of tobacco sample A is weighed, 5-50 mL of phosphate buffer solution is added to adjust the pH value to 1-5, foaming is carried out for 3-10 min, 10-30 mL of acetonitrile and 20-100 mu L of 30.0mg/L d-acetophenone internal standard working solution are added, then vortex, centrifugation and drying are sequentially carried out, and the supernatant fluid is taken to pass through a 0.22 mu m organic phase filter membrane.
(2) The chromatographic conditions are as follows: chromatographic column: DB-5MS UI elastic quartz capillary chromatographic column (60 m x 0.25mm x 0.25 μm), sample inlet end series pre-column (5 m x 0.25 mm); carrier gas: high purity He, purity 99.999%; constant flow mode, flow rate: 1.5mL/min; sample inlet temperature: 290 ℃; sample injection mode: sample introduction without diversion; sample injection amount: 0.8. Mu.L. Heating program: the initial temperature is 50 ℃, the temperature is kept for 3min, then the temperature is raised to 75 ℃ at 5 ℃/min for 1min, then the temperature is raised to 150 ℃ at 1 ℃/min for 1min, then the temperature is raised to 260 ℃ at 2 ℃/min for 1min, and finally the temperature is raised to 290 ℃ at 10 ℃/min for 10min. The mass spectrum conditions are as follows: ion source: electron bombardment (EI); electron energy: 70eV; ion source temperature: 230 ℃; transmission line temperature: 280 ℃; mass analyzer: four-stage stick-time of flight; scanning mode: primary full scanning; mass scan range: 20 to 300amu.
(3) GC-QTOF qualitative analysis
The method comprises the steps of using Agilent MassHunter qualitative analysis software to perform qualitative analysis on a compound by searching according to molecular formulas, setting a target source as an established aldehyde ketone fragrance ingredient database, setting a mass extraction window as 3-10 mDa, performing accurate mass extraction, and taking more than two characteristic ions as qualitative basis, wherein the abundance ratio and retention time/index of the characteristic ions are consistent with those in the database. The tobacco shred sample A contains 62 kinds of aldehyde ketone fragrance components.
Taking phenylacetaldehyde and salicylaldehyde as examples, phenylacetaldehyde and salicylaldehyde can only be matched with phenylacetaldehyde when the peaks are respectively obtained at 20.55 minutes and 20.59 minutes by using NIST mass spectrum library matching. When the invention is used for searching, the phenylacetaldehyde and the salicylaldehyde can be accurately and qualitatively detected (see fig. 1, 2, 3 and 4).
Example 2
(1) The invention adopts matrix matching standard solution to draw standard curve, and the concentration of matrix adding standard solution is 10, 20, 50, 100, 200, 500 and 1000 ng/mL (equivalent to the content of 50-5 000 mug/kg in tobacco). The response of an acetophenone-d 8 internal standard correction instrument is adopted, the standard recovery rate and the daily precision of 3 levels of 0.1 mg/kg, 1mg/kg and 5mg/kg are inspected, the daily precision (n=6) is inspected at the addition level of 1mg/kg, and the signal to noise ratio of 10 times is used as the quantitative limit of the method. The result shows that 127 aldehyde ketone compounds have good linear relation (r 2 is more than 0.99), the recovery rate and the precision are good, and the analysis of semi-volatile aldehyde ketone fragrance components in actual cigarette tobacco shred samples can be satisfied. Linear range, standard recovery, relative Standard Deviation (RSD), LOQ and daytime precision the invention will not be described in detail.
(2) GC-QTOF quantitative analysis
The accurate mass extraction window can remove interference ions from the target compound during quantitative analysis, so that the quantitative result is more accurate. The quantitative results of 62 aldehyde ketone fragrance components in the tobacco shred sample A are shown in Table 2.
Taking 2-acetyl-5-methylfuran in the sample matrix as an example, as shown in FIG. 5, when the mass window is set to 0.5Da in the GC-QTOF full scan mode, an interference peak appears on the right side. When the mass extraction window is 3-10 mDa, the 2-acetyl-5-methyl furan has good peak shape and no interference peak and can be accurately quantified as shown in figure 6.
Table 2 quantitative results of 62 aldehyde and ketone fragrance components in tobacco sample A
Claims (6)
1. A GC-QTOF detection method for aldehyde ketone fragrance components in tobacco and tobacco products is characterized in that: firstly, establishing 127 aldehyde ketone fragrance component databases, including a first-level full-scan mass spectrogram, retention time, fragment ion accurate mass, ion abundance ratio and retention index calculated by taking normal alkane series as reference of each aldehyde ketone fragrance component; secondly, carrying out primary full scanning on tobacco and tobacco product samples to be detected to obtain primary full scanning data of the samples; and finally, accurately quantifying the sample measurement result by adopting a database, and accurately quantifying aldehyde-ketone fragrance components meeting qualitative conditions by using quantitative software, wherein the method comprises the following specific steps of:
(1) Preparing an aldehyde ketone fragrance ingredient standard substance into a standard solution of 1-5 mug/mL, carrying out GC-QTOF first-order full-scan analysis under set conditions to obtain a first-order full-scan mass spectrogram, retention time, fragment ion accurate mass and ion abundance ratio of each aldehyde ketone fragrance ingredient, and calculating a retention index of a target compound by taking normal alkane series as a reference;
(2) Leading the first-stage full-scan data, the retention index and the high-resolution first-stage full-scan mass spectrogram matched with NIST17 obtained in the step (1) into PCDL software, correlating the PCDL software with corresponding aldehyde ketone fragrance component information, and establishing an accurate quality database; optimizing a quality extraction window;
(3) Preparing 127 standard curves of aldehyde ketone fragrance components to d 8 Acetophenone is an internal standard to correct the instrument response;
(4) Carrying out primary full scanning on the tobacco and tobacco product samples under the same set conditions as in the step (1) to obtain primary full scanning data of the tobacco and tobacco product samples;
(5) And (3) accurately quantifying the sample measurement result by adopting a database, and accurately quantifying aldehyde-ketone fragrance components meeting qualitative conditions by using Agilent MassHunter quantitative analysis software.
2. The GC-QTOF detection method of aldehyde ketone aroma components in tobacco and tobacco products according to claim 1, wherein: the aldehyde ketone fragrance components meeting the qualitative conditions are qualitatively determined by the following method; the database is set as a target source, the mass extraction window is 3-10 mDa, more than two characteristic ions are accurately detected, and the abundance ratio and retention time/index of the characteristic ions are consistent with those in the database to serve as qualitative basis.
3. The GC-QTOF detection method of aldehyde ketone aroma components in tobacco and tobacco products according to claim 1, wherein: the tobacco and the tobacco products comprise tobacco leaves, cut tobacco of cigarettes, cut tobacco of heating non-burning cigarettes and buccal cigarettes.
4. The GC-QTOF detection method of aldehyde ketone aroma components in tobacco and tobacco products according to claim 1, wherein: the sample pretreatment method in the step (4) comprises the steps of weighing 1-5 g of tobacco and tobacco product samples, adding 5-50 mL of phosphate buffer solution to adjust the pH value to 1-5, foaming for 3-10 min, adding 10-30 mL of acetonitrile and 20-100 mu L of 30.0mg/L d 8 -acetophenone internal standard working solution, then vortex, centrifuge and dry in sequence, and take supernatant fluid to pass through 0.22 μm organic phase filter membrane.
5. The GC-QTOF detection method of aldehyde ketone aroma components in tobacco and tobacco products according to claim 1, wherein: the mass spectrum chromatographic conditions are as follows: chromatographic column: DB-5MS UI elastic quartz capillary chromatographic column (60 m X0.25 mm X0.25 μm), sample inlet end series pre-column (5 m X0.25 mm); carrier gas: high purity He, purity 99.999%; constant flow mode, flow rate: 1.5mL/min; sample inlet temperature: 290. the temperature is lower than the temperature; sample injection mode: sample introduction without diversion; sample injection amount: 0.8 Mu L; heating program: the initial temperature is 50 ℃, the temperature is kept for 3min, then the temperature is increased to 75 ℃ at 5 ℃/min for 1min, then the temperature is increased to 150 ℃ at 1 ℃/min for 1min, then the temperature is increased to 260 ℃ at 2 ℃/min for 1min, and finally the temperature is increased to 290 ℃ at 10 ℃/min for 10min;
ion source: electron bombardment (EI); electron energy: 70eV; ion source temperature: 230. the temperature is lower than the temperature; transmission line temperature: 280. the temperature is lower than the temperature; mass analyzer: four-stage stick-time of flight; scanning mode: primary full scanning; mass scan range: 20 to 300amu.
6. The GC-QTOF detection method of aldehyde ketone aroma components in tobacco and tobacco products according to claim 1, wherein: the specific names of 127 aldehyde ketone fragrance components are listed in table 1 of the specification.
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| WO2012075950A1 (en) * | 2010-12-08 | 2012-06-14 | 广东中烟工业有限责任公司 | Method for rapidly determining 16 species of inorganic anions and organic acids in tobacco simultaneously |
| WO2016071856A1 (en) * | 2014-11-06 | 2016-05-12 | Novartis Ag | Amatoxin derivatives and conjugates thereof as inhibitors of rna polymerase |
| CN109932413A (en) * | 2019-04-13 | 2019-06-25 | 中国烟草总公司郑州烟草研究院 | It volatilizees in a kind of cigarette side-stream smoke and the rapid detection method of half volatile flavor component |
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