CN114397390A - Qualitative method for catechins and alkaloids in Liupu tea - Google Patents

Qualitative method for catechins and alkaloids in Liupu tea Download PDF

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CN114397390A
CN114397390A CN202210054767.7A CN202210054767A CN114397390A CN 114397390 A CN114397390 A CN 114397390A CN 202210054767 A CN202210054767 A CN 202210054767A CN 114397390 A CN114397390 A CN 114397390A
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catechins
measured
alkaloids
tea
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罗达龙
王�华
覃蓝
文俊萍
杨梓莹
黄琳
李夷君
刘虹虹
蒋德莉
柯立坚
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Wuzhou Institutes for Food and Drug Control
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    • 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
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    • G01—MEASURING; TESTING
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    • 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
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Abstract

The invention discloses a qualitative method for catechins and alkaloids in Liupu tea, which belongs to the technical field of tea component determination, and the determination method can be used for accurately determining whether the Liupu tea contains the catechins and the alkaloids, and has the advantages of good anti-interference performance and strong specificity; the method comprises the following steps: (1) dissolving and diluting catechin and alkaloid reference substance to obtain reference substance diluent; (2) measuring the reference substance diluent by using a liquid phase mass spectrometer, and establishing a comparison mass spectrogram database; (3) taking a Liupao tea sample to be measured, soaking and filtering, centrifuging, taking an extracting solution, diluting and filtering to obtain a sample diluent to be measured; (4) and (3) measuring the diluent of the sample to be measured by using a liquid-phase mass spectrometer to obtain a sample map to be measured, and matching the sample to be measured with the data in the comparison mass spectrum map database to obtain a measurement result.

Description

Qualitative method for catechins and alkaloids in Liupu tea
Technical Field
The invention relates to the technical field of tea component determination, in particular to a qualitative method for catechins and alkaloids in Liupu tea.
Background
The Liupao tea is one of black tea, and has certain effects on delaying senescence, resisting bacteria and resisting oxidation. The tea soup brewed from Liupu tea is rich in catechins, the catechins are derivatives of flavanols, the compounds are colorless crystalline solids, the catechins can be dissolved in water, and the aqueous solution of the catechins is easily polymerized to form amorphous tannin by heating or in the presence of inorganic acid. Catechins and alkaloids belong to two major functional components in tea. Catechins include gallic acid, epigallocatechin, catechin, epicatechin, epigallocatechin gallate and epicatechin gallate.
Catechin is natural oil antioxidant, has higher antioxidant activity than vitamin E, and can scavenge free radicals generated by human body to protect cell membrane, so as to delay aging, and its bioactivity is also widely concerned. Liupu tea is used as a functional component of black tea, and catechins and alkaloids play a vital role in the effects. The substances are generally determined qualitatively by a liquid phase method, the retention time of a chromatographic peak needs to be determined qualitatively by a standard substance, and the difficulty of separating a target peak and an impurity peak in a complex matrix of tea is high. If the retention of gallic acid in liquid phase measurement is poor, the measurement is easily interfered by substances co-flowed with gallic acid, and the separation of the co-flowed substances and target substances takes a long time. The operation process is complex and the anti-interference performance is poor. Therefore, it is highly desirable to invent a method for effectively characterizing catechins and alkaloids in Liupu tea to determine whether Liupu tea contains catechins and alkaloids.
Disclosure of Invention
The invention aims to provide a qualitative method for catechins and alkaloids in Liupu tea, whether the Liupu tea contains the catechins and the alkaloids can be accurately determined by using the determination method, and the determination method has good anti-interference performance and strong specificity.
The technical scheme of the invention is as follows:
the qualitative method of catechins and alkaloids in Liupu tea comprises the following steps:
(1) dissolving and diluting catechin and alkaloid reference substance to obtain reference substance diluent;
(2) measuring the reference substance diluent obtained in the step (1) by using a liquid phase mass spectrometer, and establishing a comparison mass spectrometry database;
(3) taking a Liupao tea sample to be measured, soaking and filtering, centrifuging, taking an extracting solution, diluting and filtering to obtain a sample diluent to be measured;
(4) and (4) measuring the sample diluent to be measured obtained in the step (3) by using a liquid phase mass spectrometer to obtain a sample map to be measured, and matching the sample to be measured with data in a comparison mass spectrum database to obtain a measurement result. Furthermore, in the step (1), the catechin and the alkaloid reference substance are dissolved and diluted by methanol to prepare a reference substance diluent of 10 mu g/mL.
Further, the determination of the step (2) and the step (4) comprises liquid chromatography determination and mass spectrometry determination:
the liquid chromatography determination conditions are as follows:
a chromatographic column: c18Chromatographic column, 3.0mm × 150 mm, 2.7 μm; sample introduction amount: 3 mu L of the solution; column temperature: 30 ℃; flow rate: 0.4 mL/min; mobile phase: a is 0.1% formic acid aqueous solution, B: acetonitrile; gradient of mobile phase: 0-1 min: 2% of B; 1-5 min: 2% B → 10% B; 5-15 min: 10% B → 30% B; 15-20 min: 30% B → 40% B; 20-23 min: 40% B → 50% B; 23-25 min: 50% B → 60% B; 25-27 min: 60% B → 95% B; 27-30 min: 95% of B; 30.01-35 min: 2% of B;
the mass spectrometry conditions are as follows:
temperature of the drying gas: 290 ℃; flow rate of the dryer: 11L/min; atomizer pressure: 45 psi; temperature of sheath gas: 325 ℃; flow rate of sheath gas: 8L/min; capillary voltage: 3500V; nozzle voltage: 250V; the cracking voltage is 380V; the scanning mode is an automatic two-stage acquisition mode and a positive mode, the scanning range is 1-stage 100-1000 m/z, the scanning range is 2-stage 50-500 m/z, and the collision energy is 5-40V.
Further, in the step (3), the Liupu tea sample to be measured is placed into boiling water to be soaked for 10min, the ratio of the mass of the Liupu tea to the volume of the boiling water is 1:10g/mL, the soaked liquid is placed to the room temperature and then centrifuged for 15min at the temperature of 4 ℃, and the centrifugation speed is 9000 r/min.
Further, in the step (4), the determination result includes whether catechins including gallic acid, epigallocatechin, catechin, epicatechin, epigallocatechin gallate and epicatechin gallate and alkaloids including caffeine, theobromine and theophylline are contained.
Compared with the prior art, the invention has the beneficial effects that:
according to the qualitative method for catechins and alkaloids in Liupu tea, a reference substance diluent is obtained through Liupu tea reference substance soaking and centrifugation, the reference substance diluent is measured through a liquid mass spectrometer, a comparison mass spectrogram database is established, a Liupu tea sample to be measured is soaked and centrifuged to obtain a sample diluent to be measured, the sample diluent to be measured is measured through the liquid mass spectrometer to obtain a sample map to be measured, and the sample to be measured is matched with data in the comparison mass spectrogram database to obtain a measurement result. According to the qualitative method, the catechin substances and the alkaloid in the Liupu tea are subjected to high-resolution mass spectrometry; the database is matched with all substances, the first-level mass spectrum qualitative rate reaches more than 90 points, and the second-level mass spectrum qualitative rate meets 4 qualitative identification points to determine whether the substances exist.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this application, illustrate embodiment(s) of the invention and together with the description serve to explain the invention without limiting the invention. In the drawings:
FIG. 1 is a graph comparing secondary mass spectra of gallic acid in a mass spectra database;
FIG. 2 is a comparative mass spectrogram database for secondary mass spectra of epigallocatechin gallate;
FIG. 3 is a graph comparing caffeine secondary mass spectra in a mass spectra database;
FIG. 4 is a comparison of catechin secondary mass spectra from a mass spectra database;
FIG. 5 is a comparative mass spectrogram database for epicatechin;
FIG. 6 is a graph of the comparative mass spectrogram database for epigallocatechin gallate secondary mass spectrum;
FIG. 7 is a comparative mass spectrogram database for epicatechin gallate secondary mass spectra;
FIG. 8 is a graph of theobromine secondary mass spectra compared to a mass spectra database;
FIG. 9 is a comparative theophylline secondary mass spectrum from a mass spectral database.
Detailed Description
The technical solution of the present invention will be described in further detail with reference to the following embodiments, but the present invention is not limited thereto.
The qualitative method of catechins and alkaloids in Liupu tea comprises the following steps:
(1) dissolving catechin and alkaloid reference substance in methanol, and diluting to obtain reference substance dilution of 10 μ g/mL. Wherein, the Liupu tea sample to be measured is put into boiling water, covered and soaked for 10min, the ratio of the mass of the Liupu tea to the volume of the boiling water is 1:10g/mL, the soaking is repeated for 5 times, the extracting solutions are combined and put to the room temperature. And (3) placing the soaked liquid to room temperature, and centrifuging at 4 ℃ for 15min at 9000 r/min. Sucking 2mL of the extracting solution into a 25mL volumetric flask, diluting with water, fixing the volume to a scale, shaking up, and filtering by using a 0.2 mu m water-phase filter membrane to obtain the solution to be detected.
(2) And (2) measuring the reference substance diluent and the sample solution to be measured obtained in the step (1) by using a liquid mass spectrometer, and establishing a comparison mass spectrogram database by using the reference substance diluent to match the chromatogram obtained from the sample solution so as to perform qualitative detection.
The method comprises the following steps of (1) carrying out measurement by using an Agilent LC1290-6550-QTOF liquid chromatograph-mass spectrometer, wherein the measurement comprises the following steps:
the liquid chromatography determination conditions were:
a chromatographic column: c18Chromatographic column, 3.0mm × 150 mm, 2.7 μm; sample introduction amount: 3 mu L of the solution; column temperature: 30 ℃; flow rate: 0.4 mL/min; mobile phase: a is 0.1% formic acid aqueous solution, B: acetonitrile; gradient of mobile phase: 0-1 min: 2% of B; 1-5 min: 2% B → 10% B; 5-15 min: 10% B → 30% B; 15-20 min: 30% B → 40% B; 20-23 min: 40% B → 50% B; 23-25 min: 50% B → 60% B; 25-27 min: 60% B → 95% B; 27-30 min: 95% of B; 30.01-35 min: 2% of B;
the mass spectrometry conditions are as follows:
temperature of the drying gas: 290 ℃; flow rate of the dryer: 11L/min; atomizer pressure: 45 psi; temperature of sheath gas: 325 ℃; flow rate of sheath gas: 8L/min; capillary voltage: 3500V; nozzle voltage: 250V; the cracking voltage is 380V; the scanning mode is an automatic two-stage acquisition mode and a positive mode, the scanning range is 1-stage 100-1000 m/z, the scanning range is 2-stage 50-500 m/z, and the collision energy is 5-40V.
A database of comparative mass spectra established using gallic acid, epigallocatechin, catechin, epicatechin, epigallocatechin gallate, epicatechin gallate, caffeine, theobromine, and theophylline controls, the database containing the names, molecular formulas, CAS numbers, retention times, precise molecular weights, secondary mass spectra of each of the substances, as shown in table 1.
TABLE 1 comparison of Mass Spectrometry databases contained
Figure BDA0003475996730000061
The comparison mass spectrum database also comprises a primary mass spectrum and a secondary mass spectrum of each substance, wherein the secondary mass spectrum of each substance is as follows:
(2.1) Gallic acid secondary mass spectrogram. When the reference dilution was subjected to mass spectrometry, secondary mass spectrograms of gallic acid generated at 5V, 10V, 20V, 30V, and 40V collision energies were respectively shown in fig. 1.
(2.2) epigallocatechin gallate secondary mass spectrum. When the reference dilution was subjected to mass spectrometry, the secondary mass spectra of epigallocatechin produced at 5V, 10V, 20V, 30V, and 40V, respectively, were obtained as shown in fig. 2.
And (2.3) a caffeine secondary mass spectrum. When the reference dilution was subjected to mass spectrometry, secondary mass spectra of caffeine were generated at 5V, 10V, 20V, 30V, and 40V, respectively, as shown in fig. 3.
(2.4) Secondary mass spectrum of catechin. The secondary mass spectra of catechin produced at 5V, 10V, 20V, 30V and 40V collision energy when the reference dilution was subjected to mass spectrometry are shown in fig. 4.
(2.5) epicatechin second-order mass spectrum. The secondary mass spectra of epicatechin produced at 5V, 10V, 20V, 30V, and 40V collision energies when the control dilutions were subjected to mass spectrometry are shown in fig. 5.
(2.6) secondary mass spectrum of epigallocatechin gallate. When the reference dilution was subjected to mass spectrometry, the secondary mass spectra of epigallocatechin gallate were generated at 5V, 10V, 20V, 30V, and 40V, respectively, as shown in fig. 6.
(2.7) epicatechin gallate secondary mass spectrum. When the reference dilution was subjected to mass spectrometry, the secondary mass spectra of epicatechin gallate generated at 5V, 10V, 20V, 30V, and 40V of collision energy were shown in fig. 7.
(2.8) theobromine secondary mass spectrum. When the reference dilution was subjected to mass spectrometry, secondary mass spectra of theobromine were obtained at 5V, 10V, 20V, 30V, and 40V, respectively, as shown in fig. 8.
(2.9) theophylline secondary mass spectrum. When the reference dilution was subjected to mass spectrometry, secondary mass spectrograms of theophylline were generated at collision energies of 5V, 10V, 20V, 30V, and 40V, respectively, as shown in fig. 9.
(3) And (3) taking a Liupao tea sample to be measured, soaking and filtering, centrifuging, taking an extracting solution, diluting and filtering to obtain a sample diluent to be measured.
The Liupu tea sample to be measured is placed in boiling water to be soaked for 10min, the ratio of the mass of the Liupu tea sample to be measured to the volume of the boiling water is 1:10g/mL, the soaked liquid is placed to the room temperature and then centrifuged for 15min at the temperature of 4 ℃, and the centrifugation speed is 9000 r/min.
(4) And (4) measuring the sample diluent to be measured obtained in the step (3) by using a liquid phase mass spectrometer to obtain a sample map to be measured, and matching the sample to be measured with data in a comparison mass spectrum database to obtain a measurement result.
Wherein the determination result comprises whether catechin compounds and alkaloids are contained, the catechin compounds comprise gallic acid, epigallocatechin, catechin, epicatechin, epigallocatechin gallate and epicatechin gallate, and the alkaloids comprise caffeine, theobromine and theophylline.
The method comprises the following steps of (1) carrying out measurement by using an Agilent LC1290-6550-QTOF liquid chromatograph-mass spectrometer, wherein the measurement comprises the following steps:
the liquid chromatography determination conditions are as follows:
a chromatographic column: c18Chromatographic column, 3.0mm × 150 mm, 2.7Mu m; sample introduction amount: 3 mu L of the solution; column temperature: 30 ℃; flow rate: 0.4 mL/min; mobile phase: a is 0.1% formic acid aqueous solution, B: acetonitrile; gradient of mobile phase: 0-1 min: 2% of B; 1-5 min: 2% B → 10% B; 5-15 min: 10% B → 30% B; 15-20 min: 30% B → 40% B; 20-23 min: 40% B → 50% B; 23-25 min: 50% B → 60% B; 25-27 min: 60% B → 95% B; 27-30 min: 95% of B; 30.01-35 min: 2% of B;
the mass spectrometry conditions are as follows:
temperature of the drying gas: 290 ℃; flow rate of the dryer: 11L/min; atomizer pressure: 45 psi; temperature of sheath gas: 325 ℃; flow rate of sheath gas: 8L/min; capillary voltage: 3500V; nozzle voltage: 250V; the cracking voltage is 380V; the scanning mode is an automatic two-stage acquisition mode and a positive mode, the scanning range is 1-stage 100-1000 m/z, the scanning range is 2-stage 50-500 m/z, and the collision energy is 5-40V.
Measuring to obtain a chromatogram and a primary mass spectrogram of the catechin substances and the alkaloids in the sample to be measured, matching the measurement result with the comparison mass spectrogram database by the instrument workstation, and performing secondary mass spectrometry when the accurate molecular weight matching degree of the substances calculated by the instrument workstation reaches more than 90 minutes (primary mass spectrometry matching). And (3) calculating the identification point number of the secondary mass spectrum fragment according to the table 5 in the European Union non-mandatory execution Act 2002-657-EC to reach the identification point number of more than or equal to 4, and confirming that the sample to be measured contains the substance. The identification point number calculation mode is that the identification point number of the parent ion is 2, the identification point number of each product ion (daughter ion) obtained by parent ion conversion is 2.5, and the high-resolution mass spectrum at least comprises one parent ion and one product ion (daughter ion) converted by the parent ion according to the qualitative requirement.
The qualitative method of the invention uses the high-resolution mass spectrum to qualitatively detect the catechins and the alkaloids in the Liupu tea, and has the advantage that the high-resolution mass spectrum has better anti-interference effect on the qualitative detection of the target components in the complex matrix. The traditional liquid phase method for determining the nature of the substances needs to use standard substances to determine the retention time of chromatographic peaks, and the difficulty in separating target peaks and impurity peaks from complex matrixes of tea leaves is high. If the retention of gallic acid in liquid phase measurement is poor, the measurement is easily interfered by substances co-flowed with gallic acid, and the separation of the co-flowed substances and target substances takes a long time. The high-resolution mass spectrum is used for monitoring the mass-to-charge ratio of a measured substance and can also be characterized through the mass-to-charge ratio under the condition that a target substance and an impurity peak in a sample are not separated. The qualitative method is used for determining the catechins and the alkaloids in the Liupu tea, the database is matched with all the substances, the first-level mass spectrometry qualitative rate reaches more than 90 minutes, and the second-level mass spectrometry qualitative rate meets 4 qualitative identification points to determine whether the substances exist, and the qualitative method is strong in specificity.
The above description is only exemplary of the invention, and any modification, equivalent replacement, and improvement made within the spirit and scope of the present invention should be considered within the scope of the present invention.

Claims (5)

1. A qualitative method for catechins and alkaloids in Liupu tea is characterized by comprising the following steps:
(1) dissolving and diluting catechin and alkaloid reference substance to obtain reference substance diluent;
(2) measuring the reference substance diluent obtained in the step (1) by using a liquid phase mass spectrometer, and establishing a comparison mass spectrometry database;
(3) taking a Liupao tea sample to be measured, soaking and filtering, centrifuging, taking an extracting solution, diluting and filtering to obtain a sample diluent to be measured;
(4) and (4) measuring the sample diluent to be measured obtained in the step (3) by using a liquid phase mass spectrometer to obtain a sample map to be measured, and matching the sample to be measured with data in a comparison mass spectrum database to obtain a measurement result.
2. The qualitative method of catechins and alkaloids in Liupu tea as claimed in claim 1, wherein in step (1), a control dilution of 10 μ g/mL is prepared after catechins and alkaloids are dissolved and diluted in methanol.
3. The qualitative method of catechins and alkaloids in Liupu tea as claimed in claim 3, wherein the determination of step (2) and step (4) comprises liquid chromatography determination and mass spectrometry determination:
the liquid chromatography determination conditions are as follows:
a chromatographic column: c18Chromatographic column, 3.0mm × 150 mm, 2.7 μm; sample introduction amount: 3 mu L of the solution; column temperature: 30 ℃; flow rate: 0.4 mL/min; mobile phase: a is 0.1% formic acid aqueous solution, B: acetonitrile; gradient of mobile phase: 0-1 min: 2% of B; 1-5 min: 2% B → 10% B; 5-15 min: 10% B → 30% B; 15-20 min: 30% B → 40% B; 20-23 min: 40% B → 50% B; 23-25 min: 50% B → 60% B; 25-27 min: 60% B → 95% B; 27-30 min: 95% of B; 30.01-35 min: 2% of B;
the mass spectrometry conditions are as follows:
temperature of the drying gas: 290 ℃; flow rate of the dryer: 11L/min; atomizer pressure: 45 psi; temperature of sheath gas: 325 ℃; flow rate of sheath gas: 8L/min; capillary voltage: 3500V; nozzle voltage: 250V; the cracking voltage is 380V; the scanning mode is an automatic two-stage acquisition mode and a positive mode, the scanning range is 1-stage 100-1000 m/z, the scanning range is 2-stage 50-500 m/z, and the collision energy is 5-40V.
4. The qualitative method of catechins and alkaloids in Liupu tea as claimed in claim 1, wherein in the step (3), the Liupu tea sample to be measured is soaked in boiling water for 10min, the soaked liquid with the ratio of the mass of Liupu tea to the volume of the boiling water being 1:10g/mL is added to be placed to room temperature, and then the Liupu tea sample is centrifuged at 4 ℃ for 15min, wherein the centrifugation speed is 9000 r/min.
5. The method for qualifying catechins and alkaloids in Liupu tea as claimed in claim 1, wherein in step (4), the determination result includes the presence or absence of catechins and alkaloids, wherein the catechins include gallic acid, epigallocatechin, catechin, epicatechin, epigallocatechin gallate and epicatechin gallate, and the alkaloids include caffeine, theobromine and theophylline.
CN202210054767.7A 2022-01-18 2022-01-18 Qualitative method for catechins and alkaloids in Liupu tea Pending CN114397390A (en)

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