CN104897836B - The method of quinic acid, test kit and application thereof in detection sample - Google Patents
The method of quinic acid, test kit and application thereof in detection sample Download PDFInfo
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Abstract
The invention belongs to analysis technical field, is related to the method for quinic acid in detection sample, including the step of with ammonium acetate solution infiltration sample.The test kit of quinic acid in detection sample is further related to, including ammonium acetate solution and water phase filter membrane.The test kit is used for detecting Nicotiana tabacum L. or the quinic acid content in tobacco product, or for Nicotiana tabacum L. or the quality control of tobacco product.
Description
Technical field
The invention belongs to analysis technical field, is related to the method for quinic acid, test kit and application thereof in a kind of detection sample.
Background technology
Quinic acid (quinic acid, QA) is during plant carries out aerobic respiration, through one kind that shikimic acid pathway is formed
Ring-type, polyhydroxy and there is optically active natural phenolic acid class compound, also known as 1,3,4,5- tetrahydroxy hexamethylene -1- carboxylic acids.Kui
The molecular formula of Buddhist nun's acid is C6H7(OH)4COOH, structural formula is as shown in formula I.
Quinic acid is widely present in all kinds of plants, for example Nicotiana tabacum L., ledger bark, Folium Dauci Sativae, Fructus Mali pumilae, pears and coffee
Deng, and, quinic acid is there is also in minority funguses and antibacterial.Quinic acid and its derivant are often made as food antioxidant
With；The caffeoyl analog derivative of quinic acid obtains more concern and application at aspects such as antiviral, treatment cardiovascular disease.Cause
This, quinic acid is to extract to be worth high fine chemical product and medicine intermediate.
Additionally, content of the quinic acid in Nicotiana tabacum L. is higher, between 0.05%-1%.Quinic acid has to human body to stimulate
Property, and be harmful components phenolic compound precursor, therefore quinic acid can produce harmful effect, and meeting to Nicotiana tabacum L. organoleptic quality
The health of infringement smoker, needs control content of the quinic acid in Nicotiana tabacum L. badly.
Generally using the content of liquid chromatography analysis quinic acid, the method adopts diode array detector.But the method
Detection time longer, be unfavorable for quick detection.
There is no at present quick detection sample especially in Nicotiana tabacum L. and tobacco product quinic acid method.
Content of the invention
The method that the present inventor has obtained quinic acid in a kind of quick detection sample, is particularly suited for carrying out tobacco product
Detection.The method is quick and precisely, sensitivity is high, selectivity is good, favorable reproducibility.And, it is surprisingly found by the inventors that with ammonium acetate
Quinic acid in extraction with aqueous solution sample, pre-treatment step are simple, quick.Additionally, inventor also adopts liquid phase chromatogram-mass spectrometry combination
Usage carries out quick analysis detection to quinic acid.
The method that first aspect present invention is related to quinic acid in a kind of detection sample, comprises the steps：Use ammonium acetate water
Solution impregnation sample, obtains extracting solution.
When the infiltration refers to that ammonium acetate solution is come in contact with sample, liquid is attached to sample surfaces or penetrates into sample
Internal phenomenon.Specifically, during infiltration, ammonium acetate solution liquid level is at least the 1/3 of height of specimen or at least height of specimen
1/2, it is preferable that ammonium acetate solution is totally submerged sample.
In the method for any one of first aspect present invention, the sample is Nicotiana tabacum L. or tobacco product.
Inventor has found that the selection of Extraction solvent is had a significant impact to quinic acid analysis, and ammonium acetate solution can be by sample
In quinic acid rapid extraction out, extraction ratio is high and method is simple.And using other buffer solution of sodium phosphate (NaH2PO4-
Na2HPO4), buffer solution of potassium phosphate (K2HPO4-KH2PO4) etc. cannot to sample in quinic acid carry out effective extraction and analysis.
Method according to a first aspect of the present invention, described is detected as detection by quantitative.
In the method for any one of first aspect present invention, the concentration of the ammonium acetate solution is 0.09-0.15mol/L,
Specially 0.1-0.15mol/L or 0.12-0.15mol/L, preferably 0.1mol/L.
The concentration of ammonium acetate solution is 0.09-0.15mol/L, can substantially completely extract the quinic acid in sample.
In the method for any one of first aspect present invention, the amount for adding ammonium acetate solution in every gram of sample is 250-
1000mL, specially 250-500mL, more specifically 250mL, 300mL, 500mL, 750mL or 1000mL, preferably 500mL.
Inventor has found that, when ammonium acetate solution addition is excessive, weak output signal is easily affected by baseline noise；Add
When dosage is too small, for the high sample of quinic acid content, easily there is signal value supersaturation, determine inaccurate problem.By second
Sour aqueous ammonium addition is controlled in 250-1000mL/g, especially 500mL/g, can possess normal signal value, makes measurement accurate
Really, while suitable ammonium acetate solution addition can be such that quinic acid is uniformly extracted.
In the method for any one of first aspect present invention, the infiltration is carried out under ultrasound；Specifically, ultrasonic power is for most
Powerful 40%；More specifically, infiltrating time >=10min, further specifically, infiltrating time >=30min, >=40min or
>=50min, preferably 30min.
In the method for any one of first aspect present invention, infiltration temperature be 30-60 DEG C, specially 30 DEG C, 40 DEG C, 50 DEG C or
60 DEG C, preferably 40 DEG C.
In the method for any one of first aspect present invention, also include the step of extracting solution is filtered；Specifically, with water
Phase membrane filtration extracting solution；More specifically, the aperture of the water phase filter membrane is 0.22 μm.
In the method for any one of first aspect present invention, the step of also including with LC-MS analysis extracting solution.
According to the arbitrary method of the present invention, liquid phase chromatogram condition is any one or multinomial in following (1)-(6)：
(1) chromatographic column is Féraud door C18Liquid-phase chromatographic column；
(2) sample size is 5 μ L；
(3) mobile phase is 0.1% aqueous acetic acid；
(4) flow velocity is 0.8mL/min；
(5) column temperature is 40 DEG C；
(6) isocratic elution program, elution time 5min are adopted.
Inventor has found to adopt Féraud door C18Liquid-phase chromatographic column analyzes extracting solution, and the chromatograph peak type for obtaining is preferable, response value
Higher；Chromatographic peak response value with sample size increase and increase, but inventor discovery sample size too high when, quinic acid chromatographic peak goes out
Existing crack, have impact on the accuracy of detection；Mobile phase is made with 0.1% aqueous acetic acid, chromatographic peak is preferable, response value is higher.
According to the arbitrary method of the present invention, Mass Spectrometry Conditions are any one or multinomial in following (1)-(7)：
(1) scan mode is scanned for anion；
(2) quota ion pair 191/93, qualitative ion pair 191/85；
(3) impact energy is -20V；
(4) ion source is electron spray ionisation source；
(5) detection mode is many reaction detection；
(6) electron spray voltage is -4500V；
(7) ion source temperature is 550 DEG C.
Scanned with negative-ion mode, impact energy is -20V, select quota ion pair 191/93, qualitative ion pair 191/85 to enter
Row detection, accuracy is high, sensitivity is high, the response rate is high, reproducible.Select other impact energies and quota ion pair accurate when detecting
Exactness is relatively low.
Second aspect present invention is related to a kind of test kit of quinic acid in detection sample, including ammonium acetate solution and water phase
Filter membrane.
The test kit of any one of second aspect present invention, including any one or multinomial in following (1)-(5)：
(1) concentration of the ammonium acetate solution is 0.09-0.15mol/L, specially 0.1-0.15mol/L or 0.12-
0.15mol/L, preferably 0.1mol/L；
(2) amount of ammonium acetate solution is at least 250mL, preferably specially 250-500mL, 500mL；
(3) aperture of the water phase filter membrane is 0.22 μm；
(4) test kit is quantification assay kit；
(5) sample is Nicotiana tabacum L. or tobacco product.
Third aspect present invention is related to test kit quinic acid in detection sample, or in control sample quality
Purposes；Specifically, the sample is Nicotiana tabacum L. or tobacco product.
The beneficial effect of the invention
(1) present invention infiltrates sample with ammonium acetate solution, can extract from sample particularly Nicotiana tabacum L. or tobacco product
Quinic acid, method are simple, without using virose organic solvent.
(2) present invention analyzes the quinic acid in sample using Liquid Chromatography-Mass Spectrometry, quick and precisely, sensitivity high,
Simple to operate.
(3) response rate for analyzing quinic acid in sample using the inventive method is high, reproducible.In Nicotiana tabacum L. or tobacco product
Sample analysis in there's almost no miscellaneous peak, standard solution preferably, is diluted certain multiple, with noise by object linear dependence
The detection that quinic acid is calculated than S/N=3 is limited to 0.11mg/g, calculates quantitatively being limited to for quinic acid with signal to noise ratio S/N=10
0.35mg/g, average recovery rate are 93.8%～94.8%, relative standard deviation RSD<5% (n=6).
Description of the drawings
Fig. 1：The flow chart of analysis method in the embodiment of the present invention 1.
Fig. 2：The chromatogram of 1 Plays solution of the embodiment of the present invention.
Fig. 3：The chromatogram of extracting solution in the embodiment of the present invention 1.
Fig. 4：The mass spectrum of quinic acid in the embodiment of the present invention 1.
Fig. 5：The canonical plotting of quinic acid in the embodiment of the present invention 1.
Fig. 6：The graph of a relation of different solvents and chromatographic peak area in the embodiment of the present invention 2.
Fig. 7：Chromatogram when addition is 25mL ammonium acetate solutions in the embodiment of the present invention 3；
Fig. 8：Chromatogram when addition is 100mL ammonium acetate solutions in the embodiment of the present invention 3；
Fig. 9：The graph of a relation of different extraction times and the quinic acid content for measuring in the embodiment of the present invention 4.
Figure 10：In the embodiment of the present invention 7, pure water makees the chromatogram of mobile phase.
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and should not be taken as limiting the scope of the invention.Unreceipted concrete in embodiment
Condition person, the condition that advises according to normal condition or manufacturer are carried out.Agents useful for same or the unreceipted production firm person of instrument, are
Can pass through city available from conventional products.
Embodiment 1：Analysis to quinic acid content in tobacco product
Analysis method is as shown in Figure 1：
(1) preparing standard solution：0.1g quinic acids are weighed, 0.0001g is accurate to, molten with 0.1mol/L ammonium acetate solutions
Constant volume in 100mL brown volumetric flasks is transferred to after solution, is configured to 1mg/mL standard reserving solutions；Pipette respectively 0.1mL, 0.5mL,
The standard reserving solution of 1mL, 2mL, 3mL and 5mL with 0.1mol/L ammonium acetate solution constant volumes, obtains Kui into 100mL volumetric flasks
Buddhist nun's acid concentration is respectively the standard solution of 1 μ g/mL, 5 μ g/mL, 10 μ g/mL, 20 μ g/mL, 30 μ g/mL and 50 μ g/mL, lucifuge 4
DEG C preserve, be positioned under room temperature in advance when taking, can be used after reaching room temperature.A graticule is done weekly.
(2) extracting solution of sample is prepared：0.1g or so tobacco shreds are weighed, is placed in 150mL ground triangular flasks, accurately added
The ammonium acetate solution of 50mL, 0.1mol/L, supersound extraction 30min, ultrasonic power are 40%, through 0.22 μm of water phase membrane filtration
After obtain extracting solution.
(3) respectively extracting solution, standard solution are analyzed using LC-MS/MS methods.
Chromatographiccondition：Using Féraud door C18Liquid-phase chromatographic column, column temperature are 40 DEG C；5 μ L of sample size；Mobile phase is
0.1% aqueous acetic acid, flow velocity are 0.8ml/min；Using isocratic elution program, elution time 5min altogether.
The chromatography result of standard solution is as shown in Fig. 2 the chromatography result of extracting solution is as shown in Figure 3.
Mass spectral analyses condition：Ion source：Electron spray ionisation source (ESI)；Scan mode：Anion is scanned；Detection mode：Many
Reaction monitoring (MRM)；Electron spray voltage：-4500V；Ion source temperature：550℃；Auxiliary gas Gas1 pressure：60psi；Auxiliary gas
Gas2 pressure：50psi；Remove cluster voltage (DP)：-40V；Impact energy (CE)：-20V；Ion pair is selected：Quota ion pair 191/93,
Qualitative ion pair 191/85.The mass spectrum of extracting solution is as shown in Figure 4.
(4) result of calculation：
Regression analyses are carried out to its respective concentration with the chromatographic peak area of quinic acid in standard solution, standard curve is obtained such as
Shown in Fig. 5, concrete data are shown in Table 1.
Table 1
By the chromatographic peak area of quinic acid in extracting solution chromatogram, above standard curve is substituted into, the Kui in extracting solution is obtained
Buddhist nun's acid content, calculates the quinic acid content in tobacco shred according to the following formula.
M=1000 × (A × S)/n
In formula：
Quinic acid content (mg/g) in m tobacco shreds；
Quinic acid content (μ g/mL) in A extracting solution；
S extracting liquid volumes (mL)；
N weighs the quality (g) of tobacco shred.
The quinic acid content of the present embodiment tobacco shred is 5.2mg/g.
From table 1 and Fig. 4, the chromatographic condition for being adopted there's almost no miscellaneous in the analysis of tobacco product actual sample
Peak, object have preferable linear dependence, and mixed standard solution is diluted certain multiple, are calculated with signal to noise ratio S/N=3
The detection of quinic acid is limited to 0.11mg/g.
Embodiment 2：Different solvents and the comparison of variable concentrations
The present embodiment uses pure water, buffer solution of sodium phosphate (NaH respectively2PO4-Na2HPO4), buffer solution of potassium phosphate
(K2HPO4-KH2PO4) and 0.03mol/L, 0.09mol/L, 0.12mol/L, 0.15mol/L ammonium acetate solution to Nicotiana tabacum L.
Product is extracted, other conditions reference implementation example 1.
Buffer solution of sodium phosphate, buffer solution of potassium phosphate extract tobacco product as Extraction solvent and are not detected by chromatograph
Peak.The peak area of other Extraction solvent chromatography is as shown in Figure 6.
It will be appreciated from fig. 6 that compared with ammonium acetate solution, the quinic acid extraction ratio of Aqua pure extract tobacco product is low.Work as acetic acid
During aqueous ammonium concentration >=0.1mol/L, the extraction ratio of quinic acid is basically reached to be stablized, and 0.1mol/L ammonium acetate solutions are described
Substantially the quinic acid of tobacco product can be extracted completely.
Embodiment 3：The comparison of ammonium acetate solution Different adding amount
The present embodiment adds the 0.1mol/L ammonium acetates of 25ml, 50ml, 75ml and 100ml water-soluble respectively in tobacco product
Liquid, other reference implementation examples 1, the results are shown in Table 2.
Table 2
As shown in Table 2, for different ammonium acetate solution additions, as a result no significant difference.As Figure 7-8, when
When addition is larger, the 100mL additions of such as Fig. 8, signal value are less, are easily affected by baseline noise, and addition less when, such as
, easily there is signal value supersaturation in the 25mL additions of Fig. 7, affect measurement result.In order to take into account the completeness of extraction with detection
Accuracy, while ensureing the uniformity of sampling and reducing reagent dosage, experimental selection addition is 50mL.
Embodiment 4：The comparison of different extraction times
The present embodiment is respectively using 10min, 20min, 30min, 40min and 50min as extraction time, the Kui for each measuring
Buddhist nun's acid content is as shown in Figure 9.When ultrasonic time >=30min, the quinic acid content for measuring are basicly stable, the extraction ratio of quinic acid is most
High.For avoiding long-time ultrasound from causing the temperature of sample significantly to raise, while in order that the quinic acid in different samples can
It is fully extracted out, extraction time adopts 30min.
Embodiment 5：The comparison of different Mass Spectrometry Conditions
MS/MS collision energy (CE) is set as -15V by the present embodiment, and quota ion pair is 191/127, other reference implementation examples
1.The extracting solution chromatographic peak area for obtaining is only the 81% of 1 extracting solution chromatographic peak area of embodiment.
Embodiment 6：The comparison of different chromatographic columns
The present embodiment respectively with Agilent companies production chromatographic column ZORBAX Eclipse C18 (100mm × 2.1mm,
1.8 μm), ZORBAX Eclipse XDB-C8 (150mm × 4.6mm, 5m), ZORBAX SB-C3 (150mm × 2.1mm, 5 μm),
ZORBAX SB-C3 (100mm × 3.0mm, 1.8 μm), ZORBAX XDB-Phenyl (150mm × 4.6mm, 3.5 μm), ZORBAX
300-SCX (150mm × 2.1mm, 5 μm), chromatographic column APS-2Hypersil (100mm × 2.1mm, 5 μ of power ＆ light company's production
M) measure is analyzed with Féraud door Luna 5u C18 chromatographic columns (150.0mm × 3.9mm, 5 μm), other reference implementation examples 1,
As a result show, preferably, response value is most for the chromatograph peak type of Féraud door Luna 5u C18 chromatographic columns (150.0mm × 3.9mm, 5 μm)
High.
Embodiment 7：The comparison of different mobile phases
The present embodiment is analyzed using pure water as mobile phase, other reference implementation examples 1, obtains chromatogram such as Figure 10 institutes
Show.
Figure 10 is compared with Fig. 2-3 and is understood, when making mobile phase with pure water, the peak intensity of quinic acid is relatively low, and adopts 0.1%
When acetic acid is as mobile phase, preferably, response value is higher for chromatograph peak type.
Embodiment 8：The comparison of different sample sizes
The present embodiment is respectively with 1 μ L, 2 μ L, 5 μ L and 10 μ L sample introductions, other reference implementation examples 1.
As a result show, chromatographic peak response value can increase with the increase of sample size, when the sample size of 10 μ L is reached, Kui
The acid color spectral peak of Buddhist nun occurs splitting peak.Therefore 5 μ L sample introductions are selected.
Embodiment 9：Repeatability and the investigation of recovery of standard addition
Add the standard solution of tri- kinds of variable concentrations of 1mg/g, 5mg/g and 10mg/g respectively in sample, carry out mark-on and return
Yield is tested, and each sample is determined 6 times respectively, analysis method reference implementation example 1.According to Kui in Analysis result calculation tobacco product
The recovery of standard addition of Buddhist nun's acid, as a result as shown in table 3.
The response rate of quinic acid and repeated (n=6) in 3 tobacco product of table
As can be seen from Table 3, in 3 mark-on levels, using the method analyze detection tobacco product in quinic acid return
Yield between 93.8%-94.8%, the relative standard deviation of sample tests less than 5%, illustrate the response rate of this law compared with
Height, repeatability is preferably.
Embodiment 10：The measure of different tobacco product quinic acid contents
The quinic acid content in different sources, dissimilar Nicotiana tabacum L. is determined using the analysis method of embodiment 1, be the results are shown in Table
4.
4 different sources of table, the quinic acid content of dissimilar Nicotiana tabacum L.
| Sample | Quinic acid content (mg/g) |
| Domestic flue-cured tobacco 1 | 5.20 |
| Domestic flue-cured tobacco 2 | 6.68 |
| Domestic flue-cured tobacco 3 | 1.08 |
| Domestic flue-cured tobacco 4 | 1.07 |
| Domestic flue-cured tobacco 5 | 3.79 |
| Domestic flue-cured tobacco 6 | 1.87 |
| External Nicotiana tabacum L. 1 | 8.31 |
| External Nicotiana tabacum L. 2 | 4.97 |
| External Nicotiana tabacum L. 3 | 3.68 |
| Burley tobaccos 1 | 0.74 |
| Burley tobaccos 2 | 1.05 |
| Burley tobaccos 3 | 1.32 |
| Turkish tobaccos 1 | 4.77 |
| Turkish tobaccos 2 | 5.31 |
Although the specific embodiment of the present invention has obtained detailed description, it will be understood to those of skill in the art that.Root
According to disclosed all teachings, various modifications and replacement can be carried out to those details, these changes are in the guarantor of the present invention
Within the scope of shield.The four corner of the present invention is given by claims and its any equivalent.
Claims (18)
1. in a kind of detection sample quinic acid method, comprise the steps：
Sample is infiltrated with ammonium acetate solution, obtain extracting solution；Wherein, the ammonium acetate solution concentration is 0.09-
0.15mol/L, in every gram of sample add ammonium acetate solution amount be 250-1000mL, infiltrating time >=10min, the sample
Product are Nicotiana tabacum L. or tobacco product；
The step of methods described is also included with LC-MS analysis extracting solution；In liquid phase chromatogram condition, chromatographic column is Féraud
Door C18Liquid-phase chromatographic column, mobile phase are 0.1% aqueous acetic acid；In Mass Spectrometry Conditions, quota ion pair 191/93, qualitative ion pair
191/85, impact energy is -20V.
2. method according to claim 1, it is characterised in that any one or multinomial in following (1)-(6)：
(1) described in, detection by quantitative is detected as；
(2) the ammonium acetate solution concentration is 0.1-0.15mol/L；
(3) amount for adding ammonium acetate solution in every gram of sample is 250-500mL；
(4) infiltration is carried out under ultrasound；
(5) infiltrating time >=30min；
(6) infiltration temperature is 30-60 DEG C.
3. method according to claim 2, wherein, the ammonium acetate solution concentration is 0.12-0.15mol/L.
4. method according to claim 2, wherein, the ammonium acetate solution concentration is 0.1mol/L.
5. method according to claim 2, wherein, the amount for adding ammonium acetate solution in every gram of sample is 500mL.
6. method according to claim 2, wherein, infiltrating time is 30min.
7. method according to claim 2, wherein, infiltration temperature is 40 DEG C.
8. method according to claim 1, wherein, also includes the step of filtering the extracting solution that infiltration is obtained.
9. method according to claim 8, wherein, with water phase membrane filtration extracting solution.
10. method according to claim 9, wherein, the aperture of the water phase filter membrane is 0.22 μm.
11. methods according to claim 1, wherein, liquid phase chromatogram condition for any one in following (1)-(4) or
Multinomial：
(1) sample size is 5 μ L；
(2) flow velocity is 0.8mL/min；
(3) column temperature is 40 DEG C；
(4) isocratic elution program, elution time 5min are adopted.
12. methods according to claim 1, wherein, Mass Spectrometry Conditions are any one or many in following (1)-(5)
?：
(1) scan mode is scanned for anion；
(2) ion source is electron spray ionisation source；
(3) detection mode is many reaction detection；
(4) electron spray voltage is -4500V；
(5) ion source temperature is 550 DEG C.
Purposes in quinic acid of the 13. following test kits in detection sample；The test kit includes ammonium acetate solution and water
Phase filter membrane；Wherein, the concentration of the ammonium acetate solution is 0.09-0.15mol/L, and the sample is Nicotiana tabacum L. or tobacco product.
14. purposes according to claim 13, it is characterised in that any one or multinomial in following (1)-(4)：
(1) concentration of the ammonium acetate solution is 0.1-0.15mol/L；
(2) amount of ammonium acetate solution is at least 250mL；
(3) aperture of the water phase filter membrane is 0.22 μm；
(4) test kit is quantification assay kit.
15. purposes according to claim 14, wherein, the concentration of the ammonium acetate solution is 0.12-0.15mol/L.
16. purposes according to claim 14, wherein, the concentration of the ammonium acetate solution is 0.1mol/L.
17. purposes according to claim 14, wherein, the amount of ammonium acetate solution is 250-500mL.
18. purposes according to claim 14, wherein, the amount of ammonium acetate solution is 500mL.
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