CN106248855B - One assay method for growing tobacco middle biogenic amine - Google Patents
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Abstract
Grow tobacco the assay method of middle biogenic amine the invention belongs to one, and the present invention connects SPE as pre-treatment means using liquid-liquid extraction, using high performance liquid chromatography tandem mass spectrum（HPLC‑MS/MS）Seven kinds of biogenic amines in method measure tobacco（Putrescine, cadaverine, histamine, tyrasamine, spermine, spermidine and tryptamines）.The present invention compared with the literature, establishes a kind of method for being suitable for determining biogenic amine in tobacco, the method for foundation is simple and reliable, can apply to the detection of biogenic amine in tobacco；This method is simple and convenient to sample analysis, and detection limit is low, high sensitivity, repeatability and the rate of recovery are good.
Description
Technical field
The invention belongs to determination of biogenic amines technical field in tobacco, and in particular to a measure side for growing tobacco middle biogenic amine
Method.
Background technology
Biogenic amine is the general name of a kind of nitrogenous low molecule amount alkaline organic compound with bioactivity, and they are raw
Object itself synthetic hormones, nucleotides, the precursor of protein, can be regarded as in amino molecule 1-3 hydrogen atom by alkyl or
The low molecule amount alkaloid formed after aryl substitution.Biogenic amine can be divided into three classes according to its structure：Aliphatic (putrescine, cadaverine,
Spermine, spermidine etc.), aromatic amine (tyrasamine, β-phenyl ethylamine etc.) and heterocyclic amine (histamine, tryptamines etc.).
Biogenic amine is mainly acted on by amino acid decarboxylase and formed, and is formed at least partially through the amination of aldehydes or ketones, various dynamic
All contain a small amount of biogenic amine in plant tissue cell, its caused condition mainly there are three：First, biogenic amine can be formed by having
Free amino acid, second, the microorganism of metabolizable generation amino acid decarboxylases be present, third, being adapted to the environment of microorganism growth.
Biogenic amine is universal pure in numerous food and alcoholic fermented beverage.Biogenic amine is not only the important sources of food fragrance,
And the precursor of N- nitroso compounds synthesis.When human body excess intake biogenic amine, easily cause nervous system and angiocarpy
System injury, China have put into effect relevant criterion in 2008 and have proposed limitation requirement to the biogenic amine in food.
The detection of biogenic amine at present is typically using high performance liquid chromatography (HPLC), Capillary Electrophoresis (CE), thin-layered chromatography
(TLC) and gas chromatography (GC), above-mentioned detection method are required for deriving sample, and operation is complex.At present, it is high
Effect liquid phase chromatogram-tandem mass spectrometry (HPLC-MS/MS) due to its sample need not be derived and with high sensitivity and
Accuracy is more and more applied to the detection of trace high boiling substance.
For tobacco as a kind of special food, it also contains substantial amounts of protein and amino acid, and is needed in its production process
Raw material is purified, easily produce biogenic amine.Therefore, it is also required to examine biogenic amine in tobacco leaf production process
Survey analysis.
The content of the invention
The purpose of the present invention is the shortcomings that overcoming in the prior art, there is provided an assay method for growing tobacco middle biogenic amine, should
Method be using Liquid Chromatography-Tandem Mass Spectrometry come and meanwhile determine 7 kinds of biogenic amines in tobacco, can fast and effectively detect cigarette
The content of biogenic amine in grass.
The purpose of the present invention is achieved through the following technical solutions：One assay method for growing tobacco middle biogenic amine, bag
Include following steps,
(1) prepare and mix serial standard working solution：Prepare with concentration gradient and contain interior target mixed stocker row standard
Working solution；(2) sample extraction：Tobacco presses solid-to-liquid ratio 1g after crushing:10~1g:40mL is added to aqueous formic acid-acetonitrile
In mixed liquor, 100 μ L500ng/mL internal standards 1 are added, 7- heptamethylene diamine solution, 10000~16000 turns/min is centrifuged after mixing
4min, supernatant is taken out, filter residue is pressed into solid-to-liquid ratio 1g:10mL~1g:40mL is added in aqueous formic acid-acetonitrile mixture,
10000~16000 turns/min centrifuges 4min after mixing, takes out supernatant, merges the supernatant obtained twice, as sample extraction
Liquid；
(3) SPE column purification：The sample extracting solution that step (2) obtains is crossed into mixed type cation exchange SPE
Post (DIKMA ProElut PXC 150mg/6mL), takes eluent to dry, is dissolved in acetonitrile solution after elution, crosses 0.22 μ
M miillpore filters obtain sample purification liquid；
(4) sample obtained containing interior target mixed stocker row standard working solution and step (3) obtained step (1) is net
Change liquid and carry out HPLC-MS/MS measure under the same conditions；
(5) result calculates：Quantified by the ratio between target analytes peak area and internal standard peak area using internal standard method.
The detailed process that the step (1) prepares the serial standard working solution of mixing is as follows：Compound concentration gradient is 0.5,
1,2,5,10,25ng/mL hybrid standard working solution, the internal standard 1 of the hybrid standard working solution of each concentration, 7- heptamethylene diamines
Concentration be 10ng/mL；In the hybrid standard working solution that concentration gradient is 0.5,1,2,5,10,25ng/mL, putrescine, cadaverine,
It is (such as mixed that histamine, tyrasamine, spermine, spermidine, the concentration of seven kinds of biogenic amines of tryptamines are 0.5,1,2,5,10,25ng/mL respectively
When standardization working solution gradient is 0.5ng/mL, putrescine, cadaverine, histamine, tyrasamine, spermine, Asia in hybrid standard working solution
Spermine, the concentration of seven kinds of biogenic amines of tryptamines are 0.5ng/mL respectively).
The condition of HPLC-MS/MS measure is as follows：
Chromatographic condition：
From chromatographic column with hydrophilic function, flow velocity is 0.2~0.5mL/min, and sample size is 5~10 μ L；Analysis time is
14min；Column temperature is 40 DEG C；Mobile phase is A and B mixed system, and A is the mixed aqueous solution of ammonium formate and formic acid, wherein formic acid
Volume ratio with water is 0.1:100,15~25mmol/L of content of ammonium formate；B is formic acid acetonitrile solution, wherein formic acid and acetonitrile
Volume ratio be 0.1:100；Using gradient elution, wherein B is in the percent by volume of different time sections：0~1min,
95%；1~12min, 95%~45%；12~14min, 95%；
Mass Spectrometry Conditions：
Ion gun, electric spray ion source (ESI)；Scan pattern, cation scanning；Detection mode, multiple-reaction monitoring
(MRM)；Dry gas (N2) temperature and flow velocity：290 DEG C, 11L/min；Nebulizer pressure, 206.85kPa；Sheath gas (N2) temperature and stream
Speed, 400 DEG C, 12L/min；Capillary voltage (Capillary voltage), 3500V；Fragmentation voltage (Fragmentor
Voltage), 380V；Collision gas：N2。
The addition of tobacco is 0.05~0.3g after being crushed in the step (1).
Elution process is as follows in the step (3)：With 3~7mL after being eluted successively with 2mL aqueous formic acids and 2mL methanol
Ammoniacal liquor methanol solution elutes, and the volume fraction of formic acid is 1~2% wherein in aqueous formic acid, ammoniacal liquor in ammoniacal liquor methanol solution
The volumetric concentration of (25wt%) is 3%~7%.
Described chromatographic column with hydrophilic function is Agilent Hilic posts, and specification is：3.5μm；2.1mm×100mm.
The beneficial effect comprise that：The present invention uses using liquid-liquid extraction-series connection SPE as pre-treatment means
Seven kinds of biogenic amines (putrescine, cadaverine, histamine, junket in high performance liquid chromatography-tandem mass spectrum (HPLC-MS/MS) method measure tobacco
Amine, spermine, spermidine and tryptamines).The present invention compared with the literature, establishes a kind of side for being suitable for determining biogenic amine in tobacco
Method, the method for foundation is simple and reliable, can apply to the detection of biogenic amine in tobacco；This method is simple and convenient to sample analysis,
Detection limit is low, high sensitivity, repeatability and the rate of recovery are good.
Brief description of the drawings
Fig. 1 is the MRM figures of putrescine in standard specimen；
Fig. 2 is the MRM figures of cadaverine in standard specimen；
Fig. 3 is the MRM figures of histamine in standard specimen
Fig. 4 is the MRM figures of tyrasamine in standard specimen
Fig. 5 is the MRM figures of spermine in standard specimen
Fig. 6 is the MRM figures of spermidine in standard specimen；
Fig. 7 is the MRM figures of tryptamines in standard specimen；
Fig. 8 is the MRM figures of internal standard 1,7- heptamethylene diamines in standard specimen.
Embodiment
Under embodiment of the present invention will be described in detail in conjunction with the embodiments, but those skilled in the art will manage
Solution, the following example are merely to illustrate the present invention, and are not construed as limiting the scope of the present invention.Unreceipted specific bar in embodiment
Part person, the condition suggested according to normal condition or manufacturer are carried out.Agents useful for same or the unreceipted production firm person of instrument, being can
With the conventional products obtained by commercially available purchase.
Embodiment 1
One assay method for growing tobacco middle biogenic amine, comprises the following steps,
(1) prepare and mix serial standard working solution：Prepare with concentration gradient and contain interior target mixed stocker row standard
Working solution；
(2) sample extraction：Tobacco 0.1g presses solid-to-liquid ratio 1g after crushing:20mL be added to aqueous formic acid (2vol%)-
(volume ratio of aqueous formic acid and acetonitrile is 4 in acetonitrile mixture:1) 100 μ L 500ng/mL internal standards 1,7- heptamethylene diamines, are added
Solution, after mixing 13000 turns/min centrifuge 4min, take out supernatant, filter residue again with 2mL aqueous formic acids (2vol%)-acetonitrile
(volume ratio of aqueous formic acid and acetonitrile is 4 in mixed liquor:1) mix, 13000 turns/min centrifugation 4min, take supernatant, merge
The supernatant extracted twice, as sample extracting solution；
(3) SPE column purification：The sample extracting solution that step (2) obtains is crossed into PCX cation exchange solid-phase extraction columns
(DIKMA ProElut PXC 150mg/6mL), after being eluted successively with 2mL aqueous formic acids (volume fraction 2%) and 2mL methanol
Eluted with 5mL ammoniacal liquor methanol solution, eluent is dissolved in 5mL acetonitrile solutions after drying (volume ratio of acetonitrile and water is 95:5)
In, cross 0.22 μm of miillpore filter；
(4) sample obtained containing interior target mixed stocker row standard working solution and step (3) obtained step (1) is net
Change liquid and carry out HPLC-MS/MS measure under the same conditions；
(5) result calculates：Quantified by the ratio between target analytes peak area and internal standard peak area using internal standard method；Specifically
It is as follows：To be sat containing the ratio between target analytes peak area and internal standard peak area in interior target mixed stocker row standard working solution to be vertical
Mark, the concentration of target analytes is abscissa, drawing curve, obtains standard curve regression equation and the phase relation of object
Number；According to the ratio between target analytes peak area and internal standard peak area in sample extracting solution, working curve is substituted into, obtains mesh in sample
Mark the content of analyte.
The detailed process that the step (1) prepares the serial standard working solution of mixing is as follows：Compound concentration gradient is 0.5,
1,2,5,10,25ng/mL hybrid standard working solution, the internal standard 1 of the hybrid standard working solution of each concentration, 7- heptamethylene diamines
Concentration be 10ng/mL；In the hybrid standard working solution that concentration gradient is 0.5,1,2,5,10,25ng/mL, putrescine, cadaverine,
It is (such as mixed that histamine, tyrasamine, spermine, spermidine, the concentration of seven kinds of biogenic amines of tryptamines are 0.5,1,2,5,10,25ng/mL respectively
When standardization working solution gradient is 0.5ng/mL, putrescine, cadaverine, histamine, tyrasamine, spermine, Asia in hybrid standard working solution
Spermine, the concentration of seven kinds of biogenic amines of tryptamines are 0.5ng/mL respectively).It is measured with HPLC-MS/MS.
The condition of HPLC-MS/MS measure is as follows：
Chromatographic condition is：
From chromatographic column with hydrophilic function, (AgilentHilic posts, specification are：3.5μm；2.1mm × 100mm), flow velocity is
0.3mL/min, sample size are 10 μ L；Analysis time is 14min；Column temperature is 40 DEG C；Mobile phase is A and B mixed system, and A is
The volume ratio of the mixed aqueous solution of ammonium formate and formic acid, wherein formic acid and water is 0.1:100, the content 25mmol/L of ammonium formate；B
For formic acid acetonitrile solution, the wherein volume ratio of formic acid and acetonitrile is 0.1:100；Using gradient elution, wherein B is in different time sections
Percent by volume be：0~1min, 95%；1~12min, 95%~45% (linearly connects in 1~12min periods from 95%
It is continuous to change to 45%)；12~14min, 95%；
Mass Spectrometry Conditions：
Ion gun：Electric spray ion source (ESI)；Scan pattern, cation scanning；Detection mode, multiple-reaction monitoring
(MRM)；Dry gas (N2) temperature and flow velocity：290 DEG C, 11L/min；Nebulizer pressure, 206.85kPa (30psi)；Sheath gas (N2)
Temperature and flow velocity, 400 DEG C, 12L/min；Capillary voltage (Capillaryvoltage), 3500V；Fragmentation voltage
(Fragmentor voltage), 380V；Collision gas：N2。
7 kinds of biogenic amines (putrescine, cadaverine, histamine, tyrasamine, spermine, spermidine, tryptamines) and its internal standard 1,7- heptamethylene diamines
MRM parameters are shown in Table 1 (Fig. 1-8 is the MRM figures of 7 kinds of biogenic amines and internal standard 1,7- heptamethylene diamines)
The MRM parameters of 1 seven kinds of biogenic amines of table and internal standard 1,7- heptamethylene diamines①
Note：1. CE is collision energy；* it is quota ion.
Interior target mixed stocker row standard working solution is contained with least concentration and carries out 10 measure, 7 kinds of biologies are calculated
The standard deviation of amine (putrescine, cadaverine, histamine, tyrasamine, spermine, spermidine and tryptamines), detection limit is used as using three times standard deviation.
As a result show that (table 2) method good linearity, detection limit are low.
The equation of linear regression and linearly dependent coefficient and test limit of 2 seven kinds of biogenic amines of table
。
In order to investigate the reappearance of the inventive method, the standard liquid of seven kinds of biogenic amines is added into tobacco sample,
Prepare high (40ng/mL), in (10ng/mL), low (1ng/mL) three horizontal mark-on samples, then with assay method pair of the present invention
It is analyzed, and deducts the content of blank test organism amine in sample, calculates its measured quantity, and by adding scalar sum measured quantity to calculate recovery
Rate, each concentration level are done three parallel (the results are shown in Table 3).As a result show, three horizontal rate of recovery 88.3-106% it
Between.
The recovery of standard addition of 3 seven kinds of biogenic amines of table
。
To above-mentioned low concentration mark-on sample (1ng/mL) according to assay method of the present invention carry out 6 times in a few days with parallel survey in the daytime
It is fixed.As a result show, each compound determination in a few days and in the daytime relative standard deviation between 0.8-4.1%, illustrates this method
Reappearance and stability are very well (the results are shown in Table 4).
The in a few days day to day precision of 4 seven kinds of biogenic amines of table
。
Embodiment 3
Redrying alcoholization 1-2 5 tobacco samples are taken, sample analysis, sample point are carried out by according to assay method of the present invention
Analysis the results are shown in Table shown in 5.
The content of biogenic amine in the tobacco sample of table 5
Note："-" represents not detect in sample.
Although illustrate and describing the present invention with specific embodiment, but will be appreciated that without departing substantially from the present invention's
Many other change and modification can be made in the case of spirit and scope.It is, therefore, intended that in the following claims
Including belonging to all such changes and modifications in the scope of the invention.
Claims (4)
- A 1. assay method for growing tobacco middle biogenic amine, it is characterised in that comprise the following steps,（1）Prepare and mix serial standard working solution：Prepare with concentration gradient and worked containing interior target mixed stocker row standard The detailed process of solution is as follows：Compound concentration gradient is 0.5,1,2,5,10,25 ng/mL hybrid standard working solution, each The concentration of the internal standard 1,7- heptamethylene diamines of the hybrid standard working solution of concentration is 10 ng/mL；Concentration gradient is 0.5,1,2,5, In 10,25 ng/mL hybrid standard working solution, seven kinds of putrescine, cadaverine, histamine, tyrasamine, spermine, spermidine, tryptamines biologies The concentration of amine is 0.5,1,2,5,10,25 ng/mL respectively；（2）Sample extraction：Tobacco presses the g of solid-to-liquid ratio 1 after crushing:10mL ~1 g:40mL is added to aqueous formic acid-acetonitrile and mixed Closing in liquid, add the ng/mL internal standards 1 of 100 μ L 500,7- heptamethylene diamine solution, 10000 ~ 16000 turns/min centrifuges 4min after mixing, Supernatant is taken out, filter residue is pressed into the g of solid-to-liquid ratio 1:10mL ~1 g:40mL is added in aqueous formic acid-acetonitrile mixture, is mixed 10000 ~ 16000 turns/min centrifuges 4min afterwards, takes out supernatant, merges the supernatant obtained twice, as sample extracting solution；（3）SPE column purification：By step（2）Obtained sample extracting solution crosses mixed type cation exchange solid-phase extraction column, Take eluent to dry after elution, be dissolved in acetonitrile solution, cross 0.22 μm of miillpore filter and obtain sample purification liquid；（4）By step（1）What is obtained contains interior target mixed stocker row standard working solution and step（3）Obtained sample purification liquid HPLC-MS/MS measure is carried out under the same conditions；The condition of HPLC-MS/MS measure is as follows：Chromatographic condition：From chromatographic column with hydrophilic function, flow velocity is 0.2 ~ 0.5 mL/min, and sample size is 5 ~ 10 μ L；Analysis time is 14 min； Column temperature is 40 DEG C；Mobile phase is A and B mixed system, A is the mixed aqueous solution of ammonium formate and formic acid, wherein formic acid and water Volume ratio is 0.1:100, the mmol/L of content 15 ~ 25 of ammonium formate；B is the volume of formic acid acetonitrile solution, wherein formic acid and acetonitrile Than for 0.1:100；Using gradient elution, wherein B is in the percent by volume of different time sections：0 ~ 1min, 95%；1~12 Min, 95% ~ 45%；12 ~ 14min, 95%；Mass Spectrometry Conditions：Ion gun：Electric spray ion source；Scan pattern：Cation scans；Detection mode：Multiple-reaction monitoring；Dry temperature degree and Flow velocity：290 DEG C, 11 L/min；Nebulizer pressure：206.85 kPa；Sheath temperature degree and flow velocity：400 DEG C, 12 L/min；Capillary Tube voltage：3500 V；Fragmentation voltage：380 V；Collision gas：N2；（5）As a result calculate：Quantified by the ratio between target analytes peak area and internal standard peak area using internal standard method.
- 2. the assay method of biogenic amine in tobacco as claimed in claim 1, it is characterised in that chromatographic column with hydrophilic function used is Agilent Hilic posts, specification are：3.5μm；2.1mm×100mm.
- 3. the assay method of biogenic amine in tobacco as claimed in claim 1, it is characterised in that the step（1）Cigarette after middle crushing The addition of grass is 0.05 ~ 0.3g.
- 4. the assay method of biogenic amine in tobacco as claimed in claim 1, it is characterised in that the step（3）Middle elution process It is as follows：Eluted after being eluted successively with 2mL aqueous formic acids and 2mL methanol with 3 ~ 7 mL ammoniacal liquor methanol solutions, wherein formic acid is water-soluble The volume fraction of formic acid is 1 ~ 2% in liquid, and the volumetric concentration of ammoniacal liquor is 3% ~ 7% in ammoniacal liquor methanol solution.
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| CN108414643B (en) * | 2018-04-11 | 2021-07-09 | 江苏省家禽科学研究所 | Liquid chromatography-triple quadrupole mass spectrometry detection method for biogenic amine in chilled chicken |
| CN108333275A (en) * | 2018-04-24 | 2018-07-27 | 许昌学院 | A kind of method that LC-MS/MS measures the putrescine in soy sauce |
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| FR2928457A1 (en) * | 2008-03-05 | 2009-09-11 | Cnes Epic | METHOD FOR DETECTING AND QUANTIFYING A MOLECULE COMPRISING AT LEAST ONE AMINO FUNCTION ON A SOLID SUPPORT |
| CN101793881B (en) * | 2009-12-17 | 2012-10-24 | 东北农业大学 | Method for detecting biogenic amine in food |
| CN102788857B (en) * | 2012-08-03 | 2014-04-09 | 上海海洋大学 | Method for measuring biogenic amine in fresh chilled beef |
| KR101591362B1 (en) * | 2014-01-29 | 2016-02-04 | 재단법인 발효미생물산업진흥원 | Saccharomyces cerevisiae M-5 strain producing alcohol and gamma-aminobutyric acid and nonproducing biogenic amine isolated from fermented liquid of raspberry and uses thereof |
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