CN112505229A - Non-targeted analysis method for detecting tobacco flavors and fragrances based on HPLC-QTOF MS technology - Google Patents
Non-targeted analysis method for detecting tobacco flavors and fragrances based on HPLC-QTOF MS technology Download PDFInfo
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- 238000004458 analytical method Methods 0.000 title claims abstract description 42
- 241000208125 Nicotiana Species 0.000 title claims abstract description 39
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 39
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 34
- 235000019634 flavors Nutrition 0.000 title claims abstract description 34
- 239000003205 fragrance Substances 0.000 title claims abstract description 20
- 238000005516 engineering process Methods 0.000 title claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 239000012528 membrane Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000012074 organic phase Substances 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 229930010796 primary metabolite Natural products 0.000 claims abstract description 5
- 229930000044 secondary metabolite Natural products 0.000 claims abstract description 5
- 238000001269 time-of-flight mass spectrometry Methods 0.000 claims abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000002304 perfume Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 230000010355 oscillation Effects 0.000 claims description 7
- 238000001819 mass spectrum Methods 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005695 Ammonium acetate Substances 0.000 claims description 4
- 235000019257 ammonium acetate Nutrition 0.000 claims description 4
- 229940043376 ammonium acetate Drugs 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 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 3
- 230000005526 G1 to G0 transition Effects 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 2
- 230000010358 mechanical oscillation Effects 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 5
- 238000004811 liquid chromatography Methods 0.000 abstract description 3
- 229920002521 macromolecule Polymers 0.000 abstract description 2
- 238000001196 time-of-flight mass spectrum Methods 0.000 abstract description 2
- 150000002500 ions Chemical class 0.000 description 7
- 235000019504 cigarettes Nutrition 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 4
- 235000013599 spices Nutrition 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000004460 liquid liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
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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
- G01N30/89—Inverse chromatography
-
- 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
-
- 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
- G01N30/14—Preparation by elimination of some components
-
- 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
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
-
- 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
- G01N30/60—Construction of the column
-
- 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
-
- 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
- G01N2030/062—Preparation extracting sample from raw material
-
- 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
- G01N30/14—Preparation by elimination of some components
- G01N2030/146—Preparation by elimination of some components using membranes
Abstract
A non-target analysis method for detecting tobacco flavor based on a high performance liquid chromatography-quadrupole time of flight mass spectrometry (HPLC-QTOF MS) technology is characterized in that the tobacco flavor is extracted by a solvent and then centrifuged, and is filtered by an organic phase filter membrane, filtrate is taken for analysis, a sample is separated by a liquid chromatography column and then enters a quadrupole time of flight mass spectrometry for determination, and the full-component analysis of primary and secondary metabolites in the tobacco flavor is realized. The invention applies the HPLC-QTOF MS technology to the non-target analysis of the tobacco flavor and fragrance for the first time, is particularly suitable for analyzing macromolecules and difficult volatile substances in the tobacco flavor and fragrance, and solves the problem of chromatographic peak analysis by utilizing the characteristic of high resolution of time-of-flight mass spectrum. Compared with the prior art, the invention has the advantages that: the method can conveniently, accurately and comprehensively analyze the chemical components of the complex sample of the tobacco flavor and fragrance, and provides a reliable, stable and brand-new method for analyzing the tobacco flavor and fragrance.
Description
Technical Field
The invention belongs to the technical field of measurement of tobacco flavors and fragrances, and particularly relates to a non-targeted analysis method for detecting tobacco flavors and fragrances based on an HPLC-QTOF MS technology.
Background
The tobacco essence perfume has important significance for keeping the style and characteristics of cigarette products, and is one of important core technologies in the tobacco industry. The essence and spice for the cigarette are mostly obtained from natural spices, the quality of the essence and spice is influenced by factors such as raw materials, production process and the like, and the components of the essence and spice are difficult to accurately reflect by simply using conventional indexes such as acidity, refractive index, solubility, total volatile matter and the like and sense. Because the influence of the tobacco essence flavor on the cigarette style is usually from the synergistic effect among multiple components, the acquisition of comprehensive and systematic chemical component data of the tobacco essence flavor is very important for the design of imitation flavor, creation flavor and even cigarettes.
At present, the components of the tobacco essence perfume are mainly detected by a gas chromatography-mass spectrometry (GC-MS) or a Gas Chromatography (GC), and the detection methods based on gas chromatography separation are difficult to effectively detect semi-volatile components, particularly nonvolatile components, in the tobacco essence perfume. The liquid chromatography-mass spectrometry (LC-MS) or Liquid Chromatography (LC) based on liquid chromatography separation is suitable for detecting the nonvolatile and semi-volatile components in the tobacco essence perfume, wherein a mass spectrometry detector has a better qualitative function, but the components of the tobacco essence perfume are very complex, and the problems of large component interference and inaccurate qualitative performance exist in the first-level mass spectrometry caused by incomplete separation of multiple components. Compared with a first-level mass spectrum, the characteristic of high resolution of a quadrupole time-of-flight mass spectrum (QTOF MS) solves the difficulty of chromatographic peak analysis, thereby effectively avoiding the problems. Therefore, a non-targeted analysis method based on an HPLC-QTOF MS technology is urgently needed to be established for the full-ingredient analysis of the tobacco flavor and fragrance.
Disclosure of Invention
The invention aims to provide a non-targeted analysis method for detecting tobacco flavors and fragrances based on an HPLC-QTOF MS technology, aiming at the existing problems.
The purpose of the invention is realized by the following technical scheme:
a non-target analysis method for detecting tobacco flavor based on HPLC-QTOF MS technology is characterized in that the tobacco flavor is extracted by a solvent and then centrifuged, the filtrate is filtered by an organic phase filter membrane and analyzed, a sample is separated by a liquid chromatographic column and then enters a four-level rod flight time mass spectrometry to realize the full-component analysis of primary and secondary metabolites in the tobacco flavor, and the method comprises the following specific steps:
(1) sample pretreatment:
accurately weighing 10-200 mg of tobacco essence perfume in a 50mL centrifuge tube with a cover, accurately adding 1-40 mL of solvent for extraction, oscillating for 2-20 min, centrifuging, filtering with an organic phase filter membrane, and taking the filtrate for analysis.
(2) And (3) sample analysis:
chromatographic conditions are as follows: the chromatographic column is a reversed phase chromatographic column; column temperature: 40 ℃; mobile phase A: ammonium acetate (5mmol/L) solution containing 0.1% formic acid, mobile phase B: acetonitrile; gradient elution; flow rate: 0.3 mL/min; sample introduction volume: 10 μ L.
Mass spectrum conditions: an ESI source; respectively scanning in positive/negative ion mode; ion source temperature: 500 ℃; cluster cleavage voltage: 40V; collision energy: 10V; spraying voltage: + 5500V/-4500V; atomizing gas pressure: 55 psi; air curtain pressure: 35 psi; auxiliary gas pressure: 50 psi; scanning range: m/z is 100 to 1000.
In the present invention, the extraction solvent in the sample pretreatment may be methanol, water, or a mixed solvent of the two. The sample is sufficiently oscillated before centrifugation, and the optional oscillation mode is vortex oscillation, ultrasonic oscillation or mechanical oscillation.
The reverse phase chromatography column described in the chromatographic conditions was an Atlantis @ T3 column (column length 150mm, internal diameter 2.1mm, stationary phase particle 3 μm). The gradient elution condition is 0-1 min, and 97% of A; 1-1.5 min, 97-85% A; 1.5-18 min, 85% -2% A; 18-25 min, 2% A; 25-25.1 min, 2% -97% A; 25.1-35 min, 97% A.
In general, compared to existing detection methods, the present invention has the following technical advantages:
1. the invention applies the HPLC-QTOF MS technology to the non-targeted analysis of the tobacco flavor and fragrance for the first time, is particularly suitable for the analysis of macromolecules and difficult volatile substances in the tobacco flavor and fragrance, solves the problem of chromatographic peak analysis by utilizing the characteristic of high flight time mass spectrum resolution, can conveniently, accurately and comprehensively analyze the chemical components of a complex sample of the tobacco flavor and fragrance, and provides a reliable, stable and brand-new method for analyzing the tobacco flavor and fragrance.
2. A more important feature of the present invention is to have no compound selectivity during the extraction process, which is also a great difference from the current targeted analysis methods; at present, most of the analysis of the flavors and fragrances is a targeted analysis method, the detected compounds are extremely limited, the operation is complicated, and the time consumption is long, so that the analysis of the flavors and fragrances for cigarettes is severely limited.
3. The method has simple pretreatment, high sample determination and analysis efficiency, and is suitable for high-throughput analysis of large-batch samples.
Drawings
FIG. 1: extracted ion flow diagram of flavor and fragrance positive ion mode in the examples.
FIG. 2: the extracted ion flow diagram of the flavor and fragrance anion mode in the examples.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
A non-target analysis method for detecting tobacco flavor based on HPLC-QTOF MS technology is characterized in that the tobacco flavor is extracted by a solvent and then centrifuged, the filtrate is filtered by an organic phase filter membrane and analyzed, a sample is separated by a liquid chromatographic column and then enters a four-level rod flight time mass spectrometry to realize the full-component analysis of primary and secondary metabolites in the tobacco flavor, and the method comprises the following specific steps:
(1) sample pretreatment:
accurately weighing 20mg of tobacco essence perfume in a 50mL centrifuge tube with a cover, accurately adding 20mL of 50% methanol + water solution for extraction (namely methanol and water account for 50% respectively), performing vortex oscillation for 10min, centrifuging, filtering with an organic phase filter membrane, and taking the filtrate for analysis.
(2) And (3) sample analysis:
chromatographic conditions are as follows: the chromatographic column is an Atlantis @ T3 column (the column is 150mm long, the inner diameter is 2.1mm, and the stationary phase particle size is 3 mu m); column temperature: 40 ℃; mobile phase A: ammonium acetate (5mmol/L) solution containing 0.1% formic acid, mobile phase B: acetonitrile; the gradient elution condition is 0-1 min, 97% A; 1-1.5 min, 97-85% A; 1.5-18 min, 85% -2% A; 18-25 min, 2% A; 25-25.1 min, 2% -97% A; 25.1-35 min, 97% A; flow rate: 0.3 mL/min; sample introduction volume: 10 μ L.
Mass spectrum conditions: an ESI source; respectively scanning in positive/negative ion mode; ion source temperature: 500 ℃; cluster cleavage voltage: 40V; collision energy: 10V; spraying voltage: + 5500V/-4500V; atomizing gas pressure: 55 psi; air curtain pressure: 35 psi; auxiliary gas pressure: 50 psi; scanning range: m/z is 100 to 1000.
Example 2
A tobacco flavor sample is selected, primary metabolites and secondary metabolites in the sample are subjected to non-targeted analysis according to the analysis method described in example 1, and the results are shown in Table 1.
Table 1 shows the results of non-targeted analysis of flavors and fragrances for tobacco
Claims (6)
1. A non-target analysis method for detecting tobacco flavor and fragrance based on a high performance liquid chromatography-quadrupole time of flight mass spectrometry (HPLC-QTOF MS) technology is characterized by comprising the following steps: the method comprises the steps of extracting tobacco essence perfume by using a solvent, centrifuging, filtering by using an organic phase filter membrane, taking filtrate for analysis, separating a sample by using a liquid chromatographic column, and then determining by using a four-stage rod flight time mass spectrum to realize the full-ingredient analysis of primary and secondary metabolites in the tobacco essence perfume, and comprises the following specific steps:
(1) sample pretreatment:
accurately weighing 10-200 mg of tobacco essence perfume into a 50mL centrifuge tube with a cover, accurately adding 1-40 mL of solvent for extraction, oscillating for 2-20 min, centrifuging, filtering by an organic phase filter membrane, and taking filtrate for analysis;
(2) and (3) sample analysis:
chromatographic conditions are as follows: the chromatographic column is a reversed phase chromatographic column; column temperature: 40oC; mobile phase A: ammonium acetate solution containing 0.1% formic acid, mobile phase B: acetonitrile; gradient elution; flow rate: 0.3 mL/min; sample introduction volume: 10 mu L of the solution;
mass spectrum conditions: an ESI source; respectively scanning in positive/negative ion mode; ion source temperature: 500oC; cluster cleavage voltage: 40V; collision energy: 10V; spraying voltage: + 5500V/-4500V; atomizing gas pressure: 55 psi; air curtain pressure: 35 psi; auxiliary gas pressure: 50 psi; scanning range: m/z is 100 to 1000.
2. The analytical method of claim 1, wherein: the solvent is methanol, water or a mixed solvent of the methanol and the water.
3. The analytical method of claim 1, wherein: the oscillation mode is vortex oscillation, ultrasonic oscillation or mechanical oscillation.
4. The analytical method of claim 1, wherein: the reverse phase chromatographic column is an Atlantis @ T3 column, the length of the column is 150mm, the inner diameter of the column is 2.1mm, and the particle size of a stationary phase is 3 mu m.
5. The analytical method of claim 1, wherein: the gradient elution condition is 0-1 min, and 97% of A; 1-1.5 min, 97-85% A; 1.5-18 min, 85% -2% A; 2 percent of A for 18-25 min, 25-25.1 min and 2-97 percent of A; 25.1-35 min, 97% A.
6. The analytical method of claim 1, wherein: the concentration of the ammonium acetate solution was 5 mmol/L.
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| CN113009054A (en) * | 2021-03-31 | 2021-06-22 | 华南农业大学 | Method for non-directionally screening flavors and fragrances and derivatives thereof in food based on gas phase mass spectrum characteristic fragments |
| CN113109483A (en) * | 2021-05-07 | 2021-07-13 | 上海烟草集团有限责任公司 | Analysis method for pyrolysis aroma components of potentially-fragrant raw material for cigarettes |
| CN114509519A (en) * | 2022-03-14 | 2022-05-17 | 浙江中烟工业有限责任公司 | Method for tracing and analyzing natural monomer fragrance raw materials in flavoring essence |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113009054A (en) * | 2021-03-31 | 2021-06-22 | 华南农业大学 | Method for non-directionally screening flavors and fragrances and derivatives thereof in food based on gas phase mass spectrum characteristic fragments |
| CN113109483A (en) * | 2021-05-07 | 2021-07-13 | 上海烟草集团有限责任公司 | Analysis method for pyrolysis aroma components of potentially-fragrant raw material for cigarettes |
| CN113109483B (en) * | 2021-05-07 | 2023-05-16 | 上海烟草集团有限责任公司 | Analysis method of pyrolysis aroma components of latent aroma type aroma raw materials for cigarettes |
| CN114509519A (en) * | 2022-03-14 | 2022-05-17 | 浙江中烟工业有限责任公司 | Method for tracing and analyzing natural monomer fragrance raw materials in flavoring essence |
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