CN106950322B - The positive liquid chromatography-tandem mass of nicotine optical isomer in a kind of tobacco and tobacco product - Google Patents

The positive liquid chromatography-tandem mass of nicotine optical isomer in a kind of tobacco and tobacco product Download PDF

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CN106950322B
CN106950322B CN201710338953.2A CN201710338953A CN106950322B CN 106950322 B CN106950322 B CN 106950322B CN 201710338953 A CN201710338953 A CN 201710338953A CN 106950322 B CN106950322 B CN 106950322B
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nicotine
tobacco
column
isopropanol
tandem mass
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CN106950322A (en
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余晶晶
蔡君兰
王冰
秦亚琼
刘克建
赵晓东
薛聪
刘绍锋
张晓兵
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Zhengzhou Tobacco Research Institute of CNTC
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Zhengzhou Tobacco Research Institute of CNTC
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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
    • G01N30/02—Column 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
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N30/06—Preparation
    • G01N2030/062—Preparation extracting sample from raw material

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Abstract

The positive liquid chromatography-tandem mass of nicotine optical isomer in a kind of tobacco and tobacco product, it is the nicotine extracted with NaOH solution-n-hexane in tobacco leaf, the separation of nicotine optical isomer is realized using chiral chromatographic column, high pressure pump introduces isopropanol and is shunted after column, in conjunction with Tandem Mass Spectrometry Analysis, S- (-)-nicotine and the separation of R- (+)-nicotine and Sensitive Detection in tobacco and tobacco product are realized.It the features of the present invention and has the beneficial effect that: isopropanol being introduced using high pressure pump after column and is shunted, reduce the amount into mass spectrographic nonpolar solvent, the amount of polar solvent isopropanol is compensated for simultaneously, improve Ionization Efficiency, to meet the requirement of Liquid Chromatography-Tandem Mass Spectrometry analysis, and improve the sensitivity of analysis；Compared with the conventional method, the chromatographic isolation degree of two kinds of nicotine optical isomers of the present invention is high (retention time differs 1min)；Analysis time is short (only needing 17min)。

Description

Positive liquid chromatogram-string of nicotine optical isomer in a kind of tobacco and tobacco product Join Mass Spectrometry detection method
Technical field
The invention belongs to chiral isomers in complex sample to separate, analyze detection technique research, and in particular to a kind of positive Liquid Chromatography-Tandem Mass Spectrometry analyzes nicotine optical isomer in tobacco and tobacco product, mainly uses NaOH solution-n-hexane The nicotine in tobacco leaf is extracted, the separation of nicotine optical isomer is realized using chiral chromatographic column, high pressure pump introduces different after column Propyl alcohol is simultaneously shunted, and in conjunction with Tandem Mass Spectrometry Analysis, realizes S- (-)-nicotine and R- (+)-nicotine in tobacco and tobacco product Separation and Sensitive Detection.
Background technique
Nicotine is the most abundant alkaloid of content in tobacco and flue gas, is the major impetus of mankind's smoking.There are two nicotine Optical isomer, i.e. S- (-)-nicotine and R- (+)-nicotine.The two has entirely different metabolic mechanism and physiological property, S- Physiological activity and toxicity ratio R- (+)-nicotine of (-)-nicotine are stronger.Therefore, the separation of nicotine optical isomer is analyzed in pharmacy It is of great significance with smoking and healthy aspect.
The separation analysis main method of current nicotine optical isomer reported in the literature has chiral chromatographic column-two dimension gas phase color Spectrometry, chiral chromatographic column-liquid chromatography etc..The case study time existing for chiral chromatographic column-two-dimensional gas chromatography is long；And Chiral chromatographic column-liquid chromatography is the problem is that sensitivity is lower.Since the nicotine in natural baccy is mainly S- (-)- Nicotine, and R- (+)-nicotine only accounts for the 0.2 ~ 0.3% of nicotine total amount.Existing method R- (+)-nicotine lower to content is difficult to reality Existing accurate quantitative analysis.
Summary of the invention
The purpose of the present invention is in view of the above problems, proposing a kind of positive Liquid Chromatography-Tandem Mass Spectrometry analysis tobacco And nicotine optical isomer in tobacco product, isopropanol is mainly introduced using high pressure pump after column and is shunted, To realize Mass Spectrometer Method and improvement method sensitivity.
The purpose of the present invention is achieved through the following technical solutions:
The positive liquid chromatography-tandem mass of nicotine optical isomer in a kind of tobacco and tobacco product is The nicotine in tobacco leaf is extracted with NaOH solution-n-hexane, realizes the separation of nicotine optical isomer using chiral chromatographic column, after column High pressure pump introduces isopropanol and is shunted, and in conjunction with Tandem Mass Spectrometry Analysis, realizes S- (-)-cigarette in tobacco and tobacco product Alkali and the separation of R- (+)-nicotine and Sensitive Detection, specific step is as follows:
A, tobacco sample pre-treatment:
0.1 ~ 0.3 g pipe tobacco is accurately weighed, is placed in 50 mL triangular flask, 1 ~ 5 mL 5.0%NaOH solution is added, 5 ~ 30 min are stood, 10 ~ 50 mL of hexane solution containging interior traget are accurately added, 5 ~ 30 min of ultrasonic extraction takes supernatant liquor Cross organic phase filter membrane, added with 1 ~ 3.0 g anhydrous sodium sulfate in organic phase filter membrane, purified sample solution is into positive liquid phase color Spectrum-Tandem Mass Spectrometry Analysis.
B, sample analysis:
Liquid phase chromatogram condition: being analyzed using positive liquid chromatography-tandem mass spectrometry, and chromatographic column used is chiral chromatographic column；Column Temperature: 30oC；Mobile phase A: the n-hexane containing alkalinity additive, Mobile phase B: isopropanol；Isocratic elution；Flow velocity 0.5 ~ 1.0 mL/min；10 μ L of sampling volume, analysis time are 17 min；
Isopropanol and shunting are added after column: for the sensitivity for improving positive Liquid Chromatography-Tandem Mass Spectrometry, realizing nicotine rotation The requirement of photoisomer quantitative analysis is connected after column by triple valve, introduces isopropanol, control using Agilent high pressure pump Preparing isopropanol flow velocity.Meanwhile to adapt to the requirement of mass spectral analysis, shunt after carrying out column to reduce into mass spectrographic quantity of solvent.It adopts It is shunted after carrying out column with the triple valve configured in ion source, by controlling the length of PEEK pipe, controls split ratio.
Ion source: electrospray ionisation source (ESI)；Scanning mode: cation scanning；Detection mode: multiple-reaction monitoring MRM； Electron spray voltage: 5000 V；Gas curtain atmospheric pressure: 30 psi；Assist 1 pressure of gas: 70 psi；Assist 2 pressure of gas: 70 psi；From Source temperature: 550oC.Each compound and interior target retention time, parent ion, daughter ion, collision energy (CE) and remove cluster voltage (DP) referring to table 1.
In the present invention, internal standard described in step a are as follows: use racemic d3Nicotine is internal standard, d3- S- (-)-nicotine and d3- R- (+)-nicotine joint account, concentration range are 1 ~ 10 mg/mL.
Chiral chromatographic column described in step b is Daicel chiral chromatographic column CHIRALPAK®IC, specification be 4.6 mm × 5 μm of 250 mm, i.d.；Alkaline Mobile Phase Additives are diethylamine, and additive amount is the 0.02% ~ 0.2% of n-hexane quality；It is described Isocratic condition be A:B=95:5；It is 0.1 ~ 1.0 mL/min that isopropanol flow velocity is added after column；Shunt ratio is after column 1:3~1:5；
The present invention prepares nicotine optical isomer mixing mother liquor using n-hexane and is used to prepare standard working solution, deuterated interior Mark solution and standard working solution equally use n-hexane to prepare.Positive liquid chromatogram-string is carried out to standard working solution respectively Join analytical reagent composition, and linear regression carried out to concentration ratio with S- (-)-nicotine and R- (+)-nicotine and internal standard compound peak area ratio, Obtain the standard working curve of each target compound.Minimum concentration standard working solution is taken, 10 parallel determinations calculate standard deviation Difference, 3 times of standard deviations are detection limit, and 10 times of standard deviations are quantitative limit, the results are shown in Table 2.
Beneficial effects of the present invention are as follows:
(1) nicotine optical isomer in tobacco and tobacco product is analyzed using positive Liquid Chromatography-Tandem Mass Spectrometry for the first time, Realize the separation detection of nicotine optical isomer in tobacco leaf；(2) since positive liquid chromatogram mobile phase is mainly that nonpolarity is molten Agent (n-hexane), Ionization Efficiency is low, is not suitable for Mass Spectrometer Method.Therefore, isopropanol is introduced using high pressure pump after column, improved The ratio of polar solvent, to improve the sensitivity of mass ions efficiency and analysis.Meanwhile in order to further increase mass spectrographic mist Change and Ionization Efficiency, shunt after carrying out column again after isopropanol is added, and reduce and enter mass spectrographic quantity of solvent, meet liquid chromatogram The requirement of Tandem Mass Spectrometry Analysis improves the sensitivity of analysis；(3) compared with literature procedure, two kinds of nicotine optically-actives of the invention The chromatographic isolation degree of isomers is high (retention time differs 1min)；Analysis time is short (only needing 17min)；Method high sensitivity, it is full The quantitative requirement of sufficient lower R- (+)-nicotine of content.
Detailed description of the invention
Fig. 1 is multiple-reaction monitoring mass spectrum (MRM) figure of nicotine optical isomer
Wherein: a is S- (-)-nicotine, and b is R- (+)-nicotine.
Specific embodiment
The present invention is described further below with reference to embodiment:
Embodiment 1
(1) tobacco sample pre-treatment: accurately weighing 0.30 g pipe tobacco, is added in 50 mL triangular flask, and 2 mL are added 5.0%NaOH solution, stands 10 min, and accurate be added contains d3Hexane solution 20 mL of nicotine racemic modification, it is racemic d3Nicotinic density is 5mg/mL, 15 min of ultrasonic extraction, and supernatant liquor is taken to cross having added with 2.0 g anhydrous sodium sulfates in syringe Machine phase filter membrane, filter liquor are analyzed into positive liquid chromatography-tandem mass spectrometry.
(2) instrumental conditions: being analyzed using positive Liquid Chromatography-Tandem Mass Spectrometry, and chromatographic column used is Daicel hand Property chromatographic column CHIRALPAK®IC, specification are 5 μm of 4.6 mm × 250 mm, i.d.；Column temperature: 30oC；Mobile phase A: contain The n-hexane of 0.1% diethylamine, Mobile phase B: isopropanol；95%A+5%B isocratic elution；1.0 mL/min of flow velocity；Sampling volume 10 μ L, analysis time are 17 min.Isopropanol is added after carrying out column using Agilent high pressure pump, control isopropanol flow velocity is 1 mL/min；And using shunting after the triple valve progress column configured in ion source, control split ratio is 1:5.Using ESI ion source, Cation scan pattern；Multiple-reaction monitoring MRM；Electron spray voltage: 5000 V；Gas curtain atmospheric pressure: 30 psi；Assist 1 pressure of gas: 70 psi；Assist 2 pressure of gas: 70 psi；Ion source temperature: 550oC。
Embodiment 2
5 kinds of tobacco samples are chosen, according to analysis method described in embodiment 1, measure nicotine optical isomer in sample Content, the results are shown in Table 3.
The content (mg/g) of nicotine optical isomer in 3 tobacco sample of table
Sample number into spectrum S- (-)-nicotine R- (+)-nicotine
1# 14.30 0.036
2# 16.32 0.049
3# 19.60 0.045
4# 18.30 0.049
5# 18.42 0.052

Claims (2)

1. the positive liquid chromatography-tandem mass of nicotine optical isomer in a kind of tobacco and tobacco product, special Sign is: being the nicotine extracted in tobacco leaf with NaOH solution-n-hexane, realizes nicotine optical isomer using chiral chromatographic column It separates, high pressure pump introduces isopropanol and shunted after column, in conjunction with Tandem Mass Spectrometry Analysis, realizes in tobacco and tobacco product S- (-)-nicotine and the separation of R- (+)-nicotine and Sensitive Detection, specific step is as follows:
A, sample pre-treatments:
0.1 ~ 0.3 g pipe tobacco is accurately weighed, is placed in 50 mL triangular flask, 1 ~ 5 mL 5.0%NaOH solution is added, stands 5 ~ 30 min, are accurately added 10 ~ 50 mL of hexane solution containging interior traget, and 5 ~ 30 min of ultrasonic extraction takes supernatant liquor to cross Machine phase filter membrane, added with 1 ~ 3.0 g anhydrous sodium sulfate in organic phase filter membrane, purified sample solution is into positive liquid chromatogram-string Join mass spectral analysis；
B, sample analysis:
Liquid phase chromatogram condition: being analyzed using positive liquid chromatography-tandem mass spectrometry, and chromatographic column used is Daicel chiral chromatographic column CHIRALPAK®IC, specification are 5 μm of 4.6 mm × 250 mm, i.d.；Column temperature: 30oC；Mobile phase A: contain alkalinity addition The n-hexane of agent, Mobile phase B: isopropanol；Isocratic elution, condition are A:B=95:5；1.0 mL/min of flow velocity；Sampling volume 10 μ L, analysis time are 17 min；The alkalinity Mobile Phase Additives are diethylamine, and additive amount is the 0.02% of n-hexane quality ~0.2%；
Isopropanol and shunting are added after column: being connected after column by triple valve, isopropanol is introduced using Agilent high pressure pump, Control isopropanol flow velocity is 0.1 ~ 1.0 mL/min；Meanwhile it shunting after carrying out column to reduce into mass spectrographic quantity of solvent；Using from The triple valve configured on component shunts after carrying out column, and by controlling the length of PEEK pipe, control split ratio is 1:3 ~ 1:5；
Ion source: electrospray ionisation source ESI；Scanning mode: cation scanning；Detection mode: multiple-reaction monitoring MRM；Electron spray Voltage: 5000 V；Gas curtain atmospheric pressure: 30 psi；Assist 1 pressure of gas: 70 psi；Assist 2 pressure of gas: 70 psi；Ion source temperature Degree: 550oC；Each compound and interior target retention time, parent ion, daughter ion, collision energy CE and go cluster voltage DP referring to table 1:
Table 1: nicotine and interior target retention time, parent ion, daughter ion, collision energy and cluster voltage is removed
Analyte Retention time-min Q1 -amu Q3 -amu CE -eV DP-V S- (-)-nicotine 14.39 163.0 132.0 25 80 R- (+)-nicotine 15.52 163.0 132.0 25 80 d3Nicotine racemic modification 14.39/15.52 166.0 132.0 26 80
2. detection method according to claim 1, it is characterised in that: in step a, using racemic d3Nicotine is interior Mark, d3- S- (-)-nicotine and d3- R- (+)-nicotine joint account, concentration range are 1 ~ 10 mg/mL.
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CN111398494B (en) * 2020-03-19 2022-07-12 云南中烟工业有限责任公司 Nicotine optical isomer separation and determination method based on reversed-phase two-dimensional liquid chromatography
CN112684033A (en) * 2020-12-10 2021-04-20 中国烟草总公司郑州烟草研究院 High performance liquid chromatography-quadrupole time-of-flight mass spectrometry detection method for buccal tobacco non-targeted analysis

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