CN106483217A - A kind of method that GC MS detects nascent metabolite and secondary metabolitess in fresh tobacco leaves - Google Patents
A kind of method that GC MS detects nascent metabolite and secondary metabolitess in fresh tobacco leaves Download PDFInfo
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Abstract
The present invention provides a kind of method that GC MS detects nascent metabolite and secondary metabolitess in fresh tobacco leaves, and methods described step is as follows：Quick Acquisition fresh tobacco leaves simultaneously use liquid nitrogen in-situ quick-freezing, transfer to low temperature in dry ice and transport laboratory back, method using freeze dryer frozen drying removes moisture, and with pulverizer, Nicotiana tabacum L. is pulverized, cross 40 mesh sieves, extract nascent secondary metabolitess in the Nicotiana tabacum L. after pulverizing with solvent supersonic, nitrogen is carried out to the supernatant of extracting solution and dries up, then carry out oximation reaction, silane derivative reaction to blowing thyraden, finally adopt GC MS to analyze.Have an advantage in that：Nicotiana tabacum L. acquisition method can truly reflect growth promoter period, collection position, kind and the place of production that collection Nicotiana tabacum L. is located.Nicotiana tabacum L. extracts and detection method can cover nascent, secondary metabolitess in fresh tobacco leaves, as sugar, aminoacid, organic acid, sterol, alkaloid, polyphenol etc., there is high throughput testing characteristic, Salbutamol Selected Ion Monitoring method can accurately nascent metabolite and secondary metabolitess 199 in qualitative, quantitative fresh tobacco leaves simultaneously（Standard substance verify 135）.
Description
Technical field
The present invention relates in Nicotiana tabacum L. metabolism group fresh tobacco leaves metabolism analyte detection research, specifically a kind of gas chromatogram-
Nascent metabolite sugar, aminoacid, organic acid and secondary metabolitess sterol in tandem mass spectrometry detection fresh tobacco leaves, alkaloid, many
The detection method of phenol etc..
Background technology
As important mode crop, people are mainly limited to the research of Nicotiana tabacum L. after modulation to its chemical composition to Nicotiana tabacum L., right
In fresh tobacco leaves, the chemical composition understanding including different growth promoter periods, collection position, kind and the place of production is extremely limited.To the greatest extent
The research with regard to Nicotiana tabacum L. metabolism group carried out in recent years both at home and abroad by pipe, but is detected the metabolism with accurate qualitative, quantitative
Thing limited amount, and the close phase such as the resistance of nascent and secondary metabolitess and plant, signal transduction, tabacco fragrance in fresh tobacco leaves
Close.Therefore, set up a kind of GC-MS and detect that the method for nascent metabolite and secondary metabolitess in fresh tobacco leaves is very necessary.
For the detection of Nicotiana tabacum L. metabolite, general method includes target analysis method and non-target analysis method.Target
Analysis method is typically using selection ion scan pattern（SIM）Or multiple-reaction monitoring pattern（SRM /MRM）, its sensitivity height, it is subject to
Stream peak interference is few altogether, but the method is mainly used in the research of particular types compound, is unsatisfactory for metabolism group high flux and quickly divides
The requirement of analysis.Meanwhile, this target analysis method is analyzed according to the classification of compound, there is sample pretreatment complexity, needs
Set up different analysis methods, the shortcoming that qualitative and quantitative analysis can only be carried out to known compound.Rather than target analysis
Method typically adopts full scan pattern, and can produce the full scan information of non-deflection to detect metabolite as much as possible.But
Such method also has some limitation, and such as its detector is easily saturated, and the range of linearity is narrower so that concentration range is across several
The accurate quantitative analysis of the metabolite of the order of magnitude are restricted.In addition, the metabolite number that can match and peak match result is accurate
Degree is affected by peak match parameter, and the complexity due to the imperfection data of software algorithm can lead to some error results
Produce, and then have influence on the accuracy of data prediction result and the repeatability of batch analysis data.Therefore, set up one kind to have concurrently
The detection method of the accurate qualitative, quantitative of target method and the high-throughout fresh tobacco leaves metabolite of non-target method is very necessary.
Content of the invention
The purpose of the present invention exactly provides a kind of GC-MS detection for the weak point in the presence of above-mentioned prior art
The nascent method with secondary metabolitess in fresh tobacco leaves.Different times, different cultivars, different sources can be measured using the method
The content of sugar, aminoacid, organic acid, sterol, alkaloid, polyphenol etc. in Nicotiana tabacum L., is a kind of high throughput assay method.
The purpose of the present invention is realized by following technical measures：
The GC-MS of the present invention detects that the method for nascent metabolite and secondary metabolitess in fresh tobacco leaves adopts Extraction solvent low temperature to surpass
Sound extracts and derives, and is realized nascent metabolite sugar, aminoacid in fresh tobacco leaves, is had by gas chromatograph-mass spectrometer (GC-MS) GC-MS
Machine acid and secondary metabolitess sterol, alkaloid, the detection of polyphenol, comprise the following steps that：
1）The collection of Nicotiana tabacum L., drying and pulverizing：Pluck cigarette strain appointed part Nicotiana tabacum L., rapidly with liquid nitrogen quick freeze to ensure metabolism
Thing is not degraded；Wherein, freeze dryer is pre-chilled to -40 DEG C, and lyophilization 72h, to remove moisture in Nicotiana tabacum L., uses pulverizer afterwards
Pulverize, cross 40 mesh sieves, be put in -80 DEG C of Refrigerator stores；
2）Weigh the Nicotiana tabacum L. after 10-30mg pulverizes to be placed in centrifuge tube, add the inner mark solution of 100 μ L, with the isopropanol of 1mL-
Acetonitrile-water extractant supersound extraction, after ultrasonic extraction, 4000r/min centrifugation 10min, takes supernatant and is dried up with Nitrogen evaporator；
3）Add the pyridine solution of methoxamine hydrochloride in the extracting solution drying up, enter under the conditions of 35-40 DEG C after vortex oscillation
Row oximation reaction 90-120min；This reaction can carry out oximate protection to the aldehyde radical of the metabolite such as sugar, reduces its isomer, just
In Quantitative Comparison；
4）Add the N- methyl-N- trimethyl silane trifluoroacetamide MSTFA as derivatization reagent in above-mentioned solution, be vortexed
Carry out silane derivative reaction 30-60min at 35-40 DEG C after vibration；
5）Detected using GC-MS, chromatographic mass spectrometry condition is as follows：
GC part：Chromatographic column：DB-5ms(30m×0.25mm×0.25μm)；Carrier gas：He；Sample size：1μL；Split ratio：10:1；
Flow velocity：1.0mL/min；Temperature programming：70℃（4min）It is raised to 300 DEG C（5min）, with the speed of 5 DEG C/min, injector temperature
300℃；
MS part：Transmission line and ionogenic temperature are 300 DEG C and 230 DEG C, and EI ionizes, rate of scanning 5scan/s, solvent delay
5min, sweeps mass range 40-600m/z entirely, selects ion scan totally 50 groups.
Heretofore described inner mark solution is the deuterated tridecanoic acid solution prepared with extractant, and concentration is 10 μ g/
mL；Described extractant be by volume ratio be 3:3:2 isopropanol-acetonitrile-water composition；The pyrrole of described methoxamine hydrochloride
Pyridine solution concentration is 20-40mg/mL, and addition is 50-80 μ L, and reaction carries out temperature control using air heating, shaking table；Described derivative
The addition changing reagent MSTFA is 50-80 μ L, and reaction carries out temperature control using air heating, shaking table.
The collection of heretofore described tobacco sample needs rapid removal vein, and three plants are mixed into a sample, use stannum
Foil paper wraps up blade-section, puts into quick freeze in liquid nitrogen after labelling sample number into spectrum, and is transported with dry ice embedding.
Heretofore described Mass Spectrometry detection method is Salbutamol Selected Ion Monitoring method（SIM）, each metabolite have its correspondence
Retention time and characteristic ion, can accurately nascent metabolite and secondary metabolitess 199 in qualitative, quantitative fresh tobacco leaves, its
The metabolite 135 of Plays product checking.
Beneficial effects of the present invention are as follows：
The present invention has developed the sample collection method being applied to fresh tobacco leaves and extracting method, can gather Nicotiana tabacum L. institute with actual response
Growth promoter period, collection position, kind and the place of production.And nascent, secondary metabolitess in fresh tobacco leaves can be covered, such as
Sugar, aminoacid, organic acid, sterol, alkaloid, polyphenol etc., have high throughput testing characteristic.The Nicotiana tabacum L. generation being obtained based on the method
Thank to the basic data of correlation, for finding the important metabolite closely related with Nicotiana tabacum L. odor type and its metabolic pathway, and Nicotiana tabacum L. product
The research such as the formation mechenism of matter, metabolic regulation, molecular breeding provides scientific basic.
The nascent, retention time of secondary metabolitess and title in table 1 fresh tobacco leaves
Brief description
Fig. 1 is detecting step flow chart of the present invention.
Fig. 2 is the full scan chromatogram of Flos Carthami big gold dollar in Dali in the embodiment of the present invention 1.
Fig. 3 is the full scan chromatogram of He Nanxiang county Zhongyan-100 in the embodiment of the present invention 1.
Specific embodiment
The present invention is below with reference to embodiment（Fig. 1）It is further described：
Heretofore described inner mark solution is the deuterated tridecanoic acid solution prepared with extractant, and concentration is 10 μ g/mL；Institute
The extractant stated be by volume ratio be 3:3:2 isopropanol-acetonitrile-water composition；The pyridine of described methoxamine hydrochloride is molten
Liquid concentration is 20-40mg/mL, and addition is 50-80 μ L, and reaction carries out temperature control using air heating, shaking table；Described derivatization examination
The addition of agent MSTFA is 50-80 μ L, and reaction carries out temperature control using air heating, shaking table.Hereinafter repeat no more.
Embodiment 1：The fresh tobacco leaves of the 10th leaf position of the big gold dollar of Flos Carthami of 18 Dali plantations of collection, quick removal
Vein simultaneously wraps up 3 Nicotiana tabacum Lves, liquid nitrogen flash freezer with masking foil, takes out the sample of masking foil parcel, clap broken and use lyophilizing from liquid nitrogen
Machine vacuum lyophilization 72h removes moisture removal, is milled to 40-60 mesh.Nicotiana tabacum L. 20 ~ the 25mg weighing pulverizing in 2mL centrifuge tube, plus
Enter the deuterated tridecanoic acid inner mark solution of 100 μ L, the extractant of 1mL, supersound extraction 30min, under 4000r/min after ultrasonic extraction from
Heart 10min, takes 200 μ L of supernatant liquid to dry up in sharp bottom sample injection bottle and with Nitrogen evaporator.50 μ L concentration are added in the extracting solution drying up
The pyridine solution of the methoxamine hydrochloride for 20mg/mL, reacts 90min after vortex oscillation at 37 DEG C, then adds in sample injection bottle
Enter 50 μ L MSTFA, react 60min at 37 DEG C after vortex oscillation, detected with GC-MS.
Chromatographic condition is as follows：
GC part：Chromatographic column：DB-5ms(30m×0.25mm×0.25μm)；Carrier gas：He；Sample size：1μL；Split ratio：10:1；
Flow velocity：1.0mL/min；Temperature programming：70℃（4min）It is raised to 300 DEG C（5min）, with the speed of 5 DEG C/min, injector temperature
300℃.
MS part：Transmission line and ionogenic temperature are 300 DEG C and 230 DEG C, and EI ionizes, rate of scanning 5scan/s, solvent
Postpone 5min, entirely sweep mass range 40-600m/z, select ion scan totally 50 groups.
Full scan chromatogram is as shown in Figure 2.
At continuous 10 days, carry out daily repeating to test.Randomly select 10 sample peak, calculate chromatographic peak in 10 experiments
Area, and calculate 10 times and test each chromatographic peak " peak area/internal standard area " value（S/SInterior）Relative standard deviation（RSD%）And guarantor
Stay the relative standard deviation of time, be listed in table 2.Wherein, S/SInteriorRSD<10%, retention time RSD<0.08% it was demonstrated that the method
There is preferable repeatability.
Partly nascent, relative standard deviation RSD of secondary metabolitess of the big gold dollar of table 2 Dali Flos Carthami and the response rate
Embodiment 2：The fresh tobacco leaves of the 10th leaf position of Zhongyan-100 of 18 He Nanxiang county plantations of collection, quick removal is led
Dry doubling masking foil wraps up 3 Nicotiana tabacum Lves, liquid nitrogen flash freezer, takes out the sample of masking foil parcel from liquid nitrogen, claps broken and uses freeze dryer
Vacuum lyophilization 72h removes moisture removal, and is milled to 40-60 mesh.Nicotiana tabacum L. 20 ~ the 25mg weighing pulverizing in 2mL centrifuge tube, plus
Enter the deuterated tridecanoic acid inner mark solution of 100 μ L, 1mL extractant, supersound extraction 30min, be centrifuged under 4000r/min after ultrasonic extraction
10min, takes 200 μ L of supernatant liquid to dry up in sharp bottom sample injection bottle and with Nitrogen evaporator.The concentration of 50 μ L is added in the extracting solution drying up
The pyridine solution of the methoxamine hydrochloride for 20mg/mL, reacts 90min after vortex oscillation at 37 DEG C, then adds in sample injection bottle
Enter 50 μ L MSTFA, react 60min at 37 DEG C after vortex oscillation, detected with GC-MS.
Chromatographic mass spectrometry condition is with embodiment 1.
Full scan chromatogram is as shown in Figure 3.
At continuous 10 days, carry out daily repeating to test.Randomly select 10 sample peak, calculate chromatographic peak in 10 experiments
Area, and calculate 10 times and test each chromatographic peak " peak area/internal standard area " value（S/SInterior）Relative standard deviation（RSD%）And guarantor
Stay the relative standard deviation of time, be listed in table 3.Wherein, S/SInteriorRSD<10%, retention time RSD<0.08% it was demonstrated that the method
There is preferable repeatability.
Partly nascent, relative standard deviation RSD of secondary metabolitess of table 3 He Nanxiang county Zhongyan-100 and the response rate
Claims (6)
1. a kind of GC-MS detect nascent metabolite and secondary metabolitess in fresh tobacco leaves method it is characterised in that：Using extraction
Solvent low temperature ultrasonic extracts and derives, and realizes nascent metabolite in fresh tobacco leaves by gas chromatograph-mass spectrometer (GC-MS) GC-MS
Sugar, aminoacid, organic acid and secondary metabolitess sterol, alkaloid, the detection of polyphenol, comprise the following steps that：
1）The collection of Nicotiana tabacum L., drying and pulverizing：Pluck cigarette strain appointed part Nicotiana tabacum L., rapidly with liquid nitrogen quick freeze to ensure metabolism
Thing is not degraded；Wherein, freeze dryer is pre-chilled to -40 DEG C, and lyophilization 72h, to remove moisture in Nicotiana tabacum L., uses pulverizer afterwards
Pulverize, cross 40 mesh sieves, be put in -80 DEG C of Refrigerator stores；
2）Weigh the Nicotiana tabacum L. after 10-30mg pulverizes to be placed in centrifuge tube, add the inner mark solution of 100 μ L, with the isopropanol of 1mL-
Acetonitrile-water extractant supersound extraction, after ultrasonic extraction, 4000r/min centrifugation 10min, takes supernatant and is dried up with Nitrogen evaporator；
3）Add the pyridine solution of methoxamine hydrochloride in the extracting solution drying up, enter under the conditions of 35-40 DEG C after vortex oscillation
Row oximation reaction 90-120min；This reaction can carry out oximate protection to the aldehyde radical of the metabolite such as sugar, reduces its isomer, just
In Quantitative Comparison；
4）Add the N- methyl-N- trimethyl silane trifluoroacetamide MSTFA as derivatization reagent in above-mentioned solution, be vortexed
Carry out silane derivative reaction 30-60min at 35-40 DEG C after vibration；
5）Detected using GC-MS, chromatographic mass spectrometry condition is as follows：
GC part：Chromatographic column：DB-5ms(30m×0.25mm×0.25μm)；Carrier gas：He；Sample size：1μL；Split ratio：10:1；
Flow velocity：1.0mL/min；Temperature programming：70℃（4min）It is raised to 300 DEG C（5min）, with the speed of 5 DEG C/min, injector temperature
300℃；
MS part：Transmission line and ionogenic temperature are 300 DEG C and 230 DEG C, and EI ionizes, rate of scanning 5scan/s, solvent delay
5min, sweeps mass range 40-600m/z entirely, selects ion scan totally 50 groups.
2. the method that GC-MS according to claim 1 detects nascent metabolite and secondary metabolitess in fresh tobacco leaves, it is special
Levy and be：Described inner mark solution is the deuterated tridecanoic acid solution prepared with extractant, and concentration is 10 μ g/mL.
3. the method that GC-MS according to claim 1 and 2 detects nascent metabolite and secondary metabolitess in fresh tobacco leaves,
It is characterized in that：Described extractant be by volume ratio be 3:3:2 isopropanol-acetonitrile-water composition.
4. the method that GC-MS according to claim 1 detects nascent metabolite and secondary metabolitess in fresh tobacco leaves, it is special
Levy and be：The pyridine solution concentration of described methoxamine hydrochloride is 20-40mg/mL, and addition is 50-80 μ L, and reaction adopts
Air heating, shaking table carry out temperature control；The addition of described derivatization reagent MSTFA be 50-80 μ L, reaction using air heating,
Shaking table carries out temperature control.
5. the method that GC-MS according to claim 1 detects nascent metabolite and secondary metabolitess in fresh tobacco leaves, it is special
Levy and be：The collection of described tobacco sample needs rapid removal vein, and three plants are mixed into a sample, wrap up leaf with masking foil
Piece part, puts into quick freeze in liquid nitrogen after labelling sample number into spectrum, and is transported with dry ice embedding.
6. the method that GC-MS according to claim 1 detects nascent metabolite and secondary metabolitess in fresh tobacco leaves, it is special
Levy and be：Described Mass Spectrometry detection method is Salbutamol Selected Ion Monitoring method（SIM）, each metabolite has its corresponding retention time
And characteristic ion, can accurately nascent metabolite and secondary metabolitess 199 in qualitative, quantitative fresh tobacco leaves, wherein standard substance are tested
The metabolite 135 of card.
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Cited By (14)
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| CN107037160A (en) * | 2017-05-27 | 2017-08-11 | 四川中烟工业有限责任公司 | The assay method of amino acid in tobacco leaf |
| CN107860857A (en) * | 2017-10-27 | 2018-03-30 | 中国科学院青岛生物能源与过程研究所 | A kind of extraction and analytical method of yellow silk frustule intracellular metabolite thing |
| CN108593817A (en) * | 2018-04-28 | 2018-09-28 | 上海烟草集团有限责任公司 | A kind of method and its pre-treating method detecting flavor matter in papermaking-method reconstituted tobaccos fluid sample |
| CN109541075A (en) * | 2019-01-11 | 2019-03-29 | 黑龙江八农垦大学 | Potato metabolic components sample pre-treatments and its analysis method |
| CN109633014A (en) * | 2018-12-29 | 2019-04-16 | 中国烟草总公司郑州烟草研究院 | The method and its application of 21 kinds of terpenoid contents in a kind of measurement tobacco leaf |
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| CN114839285A (en) * | 2022-04-24 | 2022-08-02 | 江苏中烟工业有限责任公司 | Method for analyzing characteristic compounds of tobacco essence and application thereof |
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| CN107037160A (en) * | 2017-05-27 | 2017-08-11 | 四川中烟工业有限责任公司 | The assay method of amino acid in tobacco leaf |
| CN107860857A (en) * | 2017-10-27 | 2018-03-30 | 中国科学院青岛生物能源与过程研究所 | A kind of extraction and analytical method of yellow silk frustule intracellular metabolite thing |
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| CN115015450A (en) * | 2022-05-26 | 2022-09-06 | 贵州省烟草科学研究院 | Method for analyzing metabolites in soil through microwave derivatization-quasi-target gas chromatography-mass spectrometry |
| CN115015450B (en) * | 2022-05-26 | 2024-05-14 | 贵州省烟草科学研究院 | Method for analyzing metabolites in soil by microwave derivatization-quasi-target gas chromatography-mass spectrometry |
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