CN106353434A - Analysis method for realizing quantitative determination of Amadori compounds in tobacco - Google Patents
Analysis method for realizing quantitative determination of Amadori compounds in tobacco Download PDFInfo
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Abstract
The invention belongs to the technical field of tobacco component detection, and particularly relates to an analysis method for realizing quantitative determination of Amadori compounds in tobacco. The analysis method comprises the following steps: 1) sample preparation: pulverizing a tobacco leaf or tobacco shred sample, and passing through a 40-mesh screen; 2) extraction: weighing the tobacco powder sample, adding a methanol/water solution, performing ultrasonic extraction, performing high-speed centrifugation on the extraction liquid, taking the supernate, and filtering; 3) dilution: diluting methanol with the filtrate to obtain a sample solution; and 4) determination: determining the sample solution in an HPLC-MS/MS (high performance liquid chromatography-mass spectrometer/mass spectrometer) MRM (multiple reaction monitoring) mode. According to the invention, the pulverized tobacco leaf/tobacco shred sample is directly extracted by the extraction solvent, centrifugated, filtered and diluted, and the determination is directly performed by means of HPLC-MS/MS, so that 10 Amadori compounds in tobacco can be simultaneously detected; and the analysis method has the advantages of simple, quick and mild operation process, favorable method reproducibility and recovery rate, high accuracy and sensitivity and multiple Amadori compound determination varieties.
Description
Technical field
The invention belongs to tobacco component detection technique field, it is related to amadori compound in a kind of quantitative determination Nicotiana tabacum L.
Analysis method, specifically adopts solvent direct extracted tobacco powder, and extract, after centrifugation, filtration, dilution, directly adopts
Hplc-ms/ms simultaneous quantitative detects the content of 10 kinds of amadori compounds.
Background technology
Amadori compound be by reducing sugar and aminoacid (or other amido-containing group compound) through condensation, dehydration,
The intermediate product of a class Maillard reaction, i.e. 1- amino -1- deoxidation -2- ketose obtained from amadori rearrangement.It is reported that [1],
In cured tobacco leaf, amadori total amount of compound, more than 2%, is important tobacco flavor component precursor thing, the sense organ to Medicated cigarette
Quality has important function.
With regard to the mensure of amadori compound, abroad it is measured using amino-acid analyzer, gc earliest, but all exists
Some problems.As, amino-acid analyzer has that separating degree is not enough, qualitative inaccurate, serious interference;And gc method derives
Change and be introduced into multiple isomers it is difficult to carry out quantitation.After 2010, two document reports hplc-ms/ms is had to analyze Nicotiana tabacum L.
In amadori compound correlational study [2,3], but measure amadori compound numbers be respectively 2 and 6, survey
Determine index negligible amounts, and be all not covered by the higher fru-asn(glucose of content in Nicotiana tabacum L. and agedoite reaction generates
Amadori compound), possible cause is affected by the restriction of the separating degree deficiency of chromatographic process.Investigated according to system, existing at present
Literature method detects that target is also all not covered with 1 pair of isomeric compound of structure proximate, i.e. fru-ile and fru-leu(Fructus Vitis viniferae
The amadori compound that sugar and isoleucine, leucine are formed respectively), its main cause is fru-ile in current literature method
All can not separate with the chromatographic peak of fru-leu, lead to not quantitation.Patent of invention cn201310487876 discloses one and grows tobacco
In measure the method for amadori compound simultaneously, the sample pre-treatments step of the method include extraction, filter, purify, hplc-
Ms/ms determination step.Wherein purifying step needs to add normal hexane to carry out extraction repeatedly in filtrate, then will be mutually dense for methanol-water
It is reduced to dry, with methanol aqueous solution constant volume again, excessively organic filter membrane.Locate before the sample that patent of invention cn201310487876.9 is adopted
Reason step is relatively complicated, needs introducing normal hexane repeatedly to be extracted.In addition, the adopted sample of cn201310487876.9
Need in pre-treatment step to carry out concentration to methanol-water solution to be evaporated, and it is to draw that the concentration of methanol-water solution is evaporated process
Enter to be heated.But, amadori compound is by sugar and the aminoacid centre that (or other contain amino-compound), reaction generated
Product, under conditions of heating, can lead to amadori compound to decompose further and generate the materials such as the aldehyde of small molecule, ketone, acid,
So the sample pre-treatments step of the analysis method of amadori compound should avoid heating to prevent side reaction from occurring as far as possible.
Therefore, develop that a kind of simple, quick, pre-treating method is gentle, accuracy and precision high and can be in Simultaneous Determination Nicotiana tabacum L.
The analysis method of multiple amadori compounds is a problem in the urgent need to address, and cigarette quality evaluation, cigarette composition are opened
Send out and there is great importance, to industries such as food, there is important reference value.
Content of the invention
The purpose of the present invention is based on above-mentioned current condition and provides one kind to quantitative determine Nicotiana tabacum L. using hplc-ms/ms
The analysis method of middle amadori compound, the method is simple to operate, quick, gentle, and accuracy and sensitivity are high, repeatability and
The response rate is good, can realize the mensure of 10 kinds of amadori compounds simultaneously, and 10 kinds of compounds cover abundance highest in Nicotiana tabacum L.
Fru-asn, and a pair of isomer fru-leu and fru-lle.
The purpose of the present invention is achieved through the following technical solutions: amadori compound in a kind of mensure Nicotiana tabacum L.
Analysis method it is characterised in that: comprise the following steps:
1) Nicotiana tabacum L. or tobacco sample are pulverized, cross 40 mesh sieves;
2) weigh offal sample 50~200 mg, add 20~40 ml methanol/water (3:7, v:v), ultrasonic extraction 20~40
Min, after centrifugation 3~10min under 5000~10000rpm rotating speed, takes supernatant to adopt 0.22 supernatant membrane filtration;
3), after filtrate being diluted 5~20 times with retarder thinner, obtain sample solution;
4) sample solution is directly used in hplc-ms/ms analysis, measures 10 kinds of amdoriization as shown in table 1 using quantified by external standard method
Compound content.
Hplc-ms/ms analysis condition is as follows:
It is 250 mm × 2.1 mm i.d. using specification, 5.0 μm of atlantis hilic silica chromatographic column;Post
Temperature: 25oc;Sample size: 5 μ l;Flow velocity: 600 μ l/min;Mobile phase: a. 0.2% formic acid solution, b. acetonitrile;Gradient:
0-0.1min, 10.5%b to 22%b gradient elution, 0.1-10 min, 22%b;Ion source: electric spray ion source (esi);Scanning
Pattern: cation scanning;Detection mode: multiple-reaction monitoring (mrm);Gas curtain atmospheric pressure: 15psi;Collision atmospheric pressure: 7 psi;
Spray voltage (capillary voltage): 5500 v;Atomization temperature: 550oc ;Atomization gas pressure: 60psi;Auxiliary gas
Pressure: 75 psi.
In step 4), retarder thinner is methanol, acetonitrile or methanol/acetonitrile mixed solvent (any mixed proportion).
The title of 10 kinds of amadori analytes and mrm parameter are shown in Table 1.
The mrm parameter of 1 10 kinds of amadori compounds of table
The amadori compound of note: 1-10 is glucose and ammonia, alanine, agedoite, glutamic acid, proline, figured silk fabrics respectively
The amadori compound that propylhomoserin, isoleucine, leucine, Phenylalanine, tryptophan reaction are formed.
Present invention is characterized in that with extractant direct extracted tobacco sample, extract through centrifugation, filter, adopt after dilution
Hplc-ms/ms is analyzed, and can carry out detection by quantitative to 10 kinds of amadori compounds in Nicotiana tabacum L., tobacco shred simultaneously, and can be first
To fru-leu, fru-ile both isomers are realized separating, are measured, and have simple to operate, quick, property and the response rate again
Good, sensitivity and the high advantage of accuracy.
Brief description
Fig. 1 is the mrm figure of 10 kinds of amadori compounds in standard specimen (left figure) and a kind of cured tobacco leaf sample (right figure).
Specific embodiment
With reference to specific embodiment, the present invention is further illustrated.
Embodiment 1
By fru-leu, fru-asn, fru-trp, fru-pro, fru-phe, fru-val, fru-lle, fru-ala,
Fru-glu, the glucosamine serial standard working solution of mixing that totally 10 kinds of amadori compounds are configured to variable concentrations,
The Concentraton gradient of wherein fru-pro, fru-asn is 0.05,0.2,0.5,2.0,5.0,10.0 g/ml, and other 8 kinds
Amadori compound concentration gradient is 0.005,0.02,0.05,0.2,0.5,1.0 g/ml.
With hplc-ms/ms, series standard working solution is analyzed, with the chromatographic peak area of object, concentration is carried out
Linear regression analyses, linear equation and correlation coefficient are as shown in table 2.Mark solution is mixed with least concentration and carries out 10 mensure, calculate
The standard deviation of 10 kinds of object chromatographic peak areas, with 3 times of standard deviations as detection limit, 10 kinds of standard deviations are quantitative limit, knot
Fruit lists table 2 in.Result shows, method good linearity, and detection limit is low.
Table 2 method linear equation, correlation coefficient, the range of linearity, detection limit and quantitative limit
Compound | Linear equation | Correlation coefficient r | Range of linearity g/ml | Detection limit ng/ml | Quantitative limit ng/ml |
glucosamine | y=5.97×103 x+1.85×104 | 0.9994 | 0.005 –1.00 | 1.92 | 6.40 |
fru-ala | y=6.08×103 x+1.79×104 | 0.9998 | 0.005 –1.00 | 1.52 | 5.07 |
fru-asn | y=2.26×103 x-2.99×103 | 0.9998 | 0.050–10.0 | 2.53 | 8.33 |
fru-glu | y=5.61×103 x-1.31×103 | 0.9996 | 0.005 –1.00 | 1.83 | 6.09 |
fru-pro | y=3.37×103 x+4.88×103 | 0.9999 | 0.050–10.0 | 1.59 | 5.31 |
fru-val | y=1.14×104 x+5.32×103 | 0.9998 | 0.005 –1.00 | 1.76 | 5.87 |
fru-lle | y=9.18×103 x-543 | 0.9997 | 0.005 –1.00 | 2.11 | 7.04 |
fru-leu | y=7.47×103 x+8.3×103 | 0.9990 | 0.005–1.00 | 1.57 | 5.22 |
fru-phe | y=8.87×103 x+4.82×103 | 0.9999 | 0.005 –1.00 | 1.35 | 4.51 |
fru-trp | y=1.21×104 x-5.27×104 | 0.9977 | 0.005–1.00 | 1.64 | 5.48 |
Embodiment 2
Weigh 100mg same tobacco powder sample, add 20 ml methanol/water (3:7, v:v), ultrasonic extraction 30 min;In 5000rpm
After centrifugation 3min under rotating speed, take supernatant 5ml to filter, take 1ml filtrate with, after 10 times of methanol dilution, surveying using hplc-ms/ms
Fixed, hplc-ms/ms method is with reference to Summary.According to aforesaid operations carry out in a few days 6 times parallel with the daytime 6 parallel examinations
Test, calculate withinday precision and the day to day precision of measurement result, as shown in table 3, withinday precision is less than 4.1%, accurate in the daytime
Degree is less than 5.4% it was demonstrated that the repeatability of method is preferable.
Table 3 method withinday precision and day to day precision
Embodiment 3
Weigh tobacco sample 100mg used by embodiment 2, add the amadori standard that concentration is high, medium and low contents level respectively
Product mixed solution, wherein each adds and carries out 3 times under concentration level repeating experiment, other operating procedures and the complete phase of embodiment 2
Same, it is measured using hplc-ms/ms and calculate the response rate.As shown in table 4, to 10 kinds of target amadori compounds, three
Under pitch-based sphere, 86.1%~120.3%, result is more satisfied for the response rate.
The table 4 method response rate
Embodiment 4
Weigh 200mg sample a(cured tobacco leaf powder), sample b(burley tobaccos Nicotiana tabacum L. powder), sample c(Turkish tobaccos tobacco leaf powder
End), it is separately added into 30 ml methanol/water (3:7, v:v), ultrasonic extraction 40 min;After centrifugation 3min under 8000rpm rotating speed,
Take supernatant 5ml to filter, take 1ml filtrate with methanol dilution (sample a, c dilute 10 times, and sample b dilutes 3 times), using hplc-
Ms/ms measures, and hplc-ms/ms method is with reference to Summary.Measurement result as shown in table 5, shows flue-cured tobacco, burley tobaccos, perfume (or spice)
In material cigarette tobacco sample, the content of amadori compound has larger difference.
List of references:
[1] dickerson. use of additives to enhance formation of amadori compounds
during aging[j]. chemical research. 1972;1101-1150.
[2]zhou w, wang j, wu d. determination of important flavour precursor
compounds (amadori compounds) in cigarettes by lc-ms/ms[j]. journal of
analytical chemistry, 2014, 69(7): 691-695.
[3] Jia Chunxiao, repaiies dragon and flies, Mouding is flourish, Mao Duobin, and liquid chromatograph one tandem mass spectrometry measures 6 kinds in Nicotiana tabacum L. simultaneously
Amadori compound, mass spectrum journal, 36(1): 45-51.
Claims (4)
1. a kind of quantitative determination Nicotiana tabacum L. in amadori compound analysis method it is characterised in that: comprise the following steps:
1) Nicotiana tabacum L. or tobacco sample are pulverized, cross 40 mesh sieves;
2) weigh offal sample 50~200 mg, add 20~40 ml methanol/water solution, ultrasonic extraction 20~40 min;?
After centrifugation 3~10min under 5000~10000rpm rotating speed, take supernatant liquid filtering, obtain filtrate;
3), after supernatant being diluted 5~20 times with retarder thinner, obtain sample solution;
4) sample solution is directly used in hplc-ms/ms analysis, measures following 10 kinds of amdori compounds using quantified by external standard method
Content, 10 kinds of amdori compounds are particularly as follows: glucosamine, fru-ala, fru-asa, fru-glu, fru-prp, fru-
val、fru-lle、fru-leu、fru-phe、fru-trp.
2. a kind of analysis method quantitative determining amadori compound in Nicotiana tabacum L. according to claim 1, its feature exists
In: hplc-ms/ms analysis condition is as follows:
It is 250 mm × 2.1 mm i.d. using specification, 5.0 μm of atlantis hilic silica chromatographic column;Post
Temperature: 25oc;Sample size: 5 μ l;Flow velocity: 600 μ l/min;Mobile phase: a. 0.2% formic acid solution, b. acetonitrile;Gradient:
0-0.1min, 10.5%b to 22%b gradient elution, 0.1-10 min, 22%b;Ion source: electric spray ion source (esi);Scanning
Pattern: cation scanning;Detection mode: multiple-reaction monitoring (mrm);Gas curtain atmospheric pressure: 15psi;Collision atmospheric pressure: 7 psi;
Spray voltage (capillary voltage): 5500 v;Atomization temperature: 550oc ;Atomization gas pressure: 60psi;Auxiliary gas
Pressure: 75 psi.
3. according to claim 1 a kind of measure Nicotiana tabacum L. in amadori compound analysis method it is characterised in that: step
In rapid 4), retarder thinner is methanol, acetonitrile or methanol/acetonitrile any mixed proportion solvent.
4. according to claim 1 a kind of measure Nicotiana tabacum L. in amadori compound analysis method it is characterised in that: institute
State v: v=3: the 7 of methanol/water solution.
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Cited By (5)
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CN107356689A (en) * | 2017-07-07 | 2017-11-17 | 中国烟草总公司郑州烟草研究院 | One grow tobacco in 12 kinds of Amadori compounds assay method |
CN113219111A (en) * | 2021-04-14 | 2021-08-06 | 上海烟草集团有限责任公司 | Method for simultaneously determining 10 Amadori compounds in tobacco |
CN114609302A (en) * | 2022-04-12 | 2022-06-10 | 河南中烟工业有限责任公司 | Method for monitoring internal quality of fenugreek extract based on HPLC-MS and application |
CN115932121A (en) * | 2023-02-06 | 2023-04-07 | 上海烟草集团有限责任公司 | Analysis method for simultaneously determining amino acids, amadori compounds and Heyns compounds in tobacco |
CN117929614A (en) * | 2024-03-22 | 2024-04-26 | 湖北省烟草科学研究院 | Method for quantitatively analyzing Amadori and Heyns rearrangement products by utilizing ion ratio |
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CN107356689B (en) * | 2017-07-07 | 2019-12-27 | 中国烟草总公司郑州烟草研究院 | Method for determining 12 Amadori compounds in tobacco |
CN113219111A (en) * | 2021-04-14 | 2021-08-06 | 上海烟草集团有限责任公司 | Method for simultaneously determining 10 Amadori compounds in tobacco |
CN114609302A (en) * | 2022-04-12 | 2022-06-10 | 河南中烟工业有限责任公司 | Method for monitoring internal quality of fenugreek extract based on HPLC-MS and application |
CN115932121A (en) * | 2023-02-06 | 2023-04-07 | 上海烟草集团有限责任公司 | Analysis method for simultaneously determining amino acids, amadori compounds and Heyns compounds in tobacco |
CN117929614A (en) * | 2024-03-22 | 2024-04-26 | 湖北省烟草科学研究院 | Method for quantitatively analyzing Amadori and Heyns rearrangement products by utilizing ion ratio |
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