CN112730656A - Detection method of anthocyanin - Google Patents
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Abstract
The invention provides a method for detecting anthocyanin, which comprises the following steps: preparing a test solution: preparing a solution of anthocyanin to be tested with the total concentration of 500 mug/mL as a solution to be tested; and (3) determination: eluting the tested solution by adopting a reverse phase chromatography, and detecting by combining a high-resolution mass spectrum, wherein the conditions of the ultra-high performance liquid chromatography are as follows: the chromatographic column is an octadecyl bonded silica gel column, the column temperature is 25 ℃, the injection amount is 2 mu l, and the mass spectrum scanning range is m/z: 100 to 1000; the conditions of the mobile phase were: the organic phase was methanol containing 1% formic acid, the aqueous phase was 1% formic acid in water, and the elution was carried out in a gradient at a flow rate of 0.3 mL/min. The detection method provided by the invention can separate all base lines of 12 anthocyanidins, and achieves the purpose of full detection of all anthocyanidins. The invention adopts the combination of ultra-high performance liquid phase and high-resolution mass spectrum, the dual-channel detection ensures the detection accuracy, the high resolution and the good separation degree improve the detection precision, and the detection limit is greatly reduced.
Description
Technical Field
The invention belongs to the technical field of chemical analysis, and particularly relates to a method for detecting anthocyanin.
Background
Anthocyanidin (anthocyanidin) belongs to flavonoid compounds, is a water-soluble natural pigment widely existing in plants, and has high nutritional value. The anthocyanin has rich resources, safety and no toxicity, and simultaneously has certain nutritional and medicinal values, so the anthocyanin has a larger development market in the aspects of foods, medicines, cosmetics and the like. At present, the domestic research on anthocyanin mainly focuses on searching plant raw materials with rich anthocyanin content, extracting the anthocyanin from the plant raw materials, putting the anthocyanin into commercial production and developing the application market of the anthocyanin. Grape skin pigments, berry pigments (strawberry, waxberry, medlar, blueberry), purple sweet potato pigments and the like are put into commercial production.
At present, no mandatory standard file is formed in the aspect of anthocyanin detection in China, however, anthocyanin components are complex and changeable, and the existing research method has large interference and few detection components, so that the quality control of anthocyanin is difficult to a certain extent. The existing detection methods mainly comprise an ultraviolet spectrophotometry method, a high performance liquid chromatography method and a high performance liquid chromatography/mass spectrometry combined method. Ultraviolet spectrophotometry is commonly used for detecting the total amount of anthocyanin, and is based on the principle that anthocyanin can change color under different pH conditions: at pH 1.0, the oxonium ion form predominates, turning red; when pH was 4.5, the hemiketal form was mainly present, the color disappeared, and the absorbance at 520nm was proportional to the anthocyanin concentration in the sample to determine the anthocyanin content. The ultraviolet spectrophotometry is the most economic analysis means with simple operation, but the method for detecting anthocyanin is often influenced by external conditions such as pH value of solvent, environmental temperature and the like, and is interfered by substances such as procyanidine, anthocyanin and the like in a sample, so that the analysis result is often high, and the sensitivity is low. The anthocyanin can be hydrolyzed under the acidic condition to generate pelargonium, cyanidin, delphinidin, paeoniflorin, petunia pigment and malvidin, and the domestic recommended detection method mainly detects the 6 anthocyanins by using a high performance liquid chromatography to quantify the anthocyanin content in the sample; however, the detection is affected by substances such as proanthocyanidins due to strongly acidic pretreatment conditions, and the result is high. Cyanidin in nature exists in the form of anthocyanin, and mainly comprises delphinidin (delphinidin) -3-O-glucoside (Dp-3-O-Glu), cyanidin-3-O-glucoside (Cy-3-O-Glu), petunidin-3-O-glucoside (Pt-3-O-Glu), pelargonium-3-O-glucoside (Pg-3-O-Glu), paeoniflorin-3-O-glucoside (Pn-3-O-Glu) and malvidin-3-O-glucoside (Ma-3-O-Glu). The content of anthocyanin in the sample can be reflected more specifically by analyzing 6 anthocyanin and 6 anthocyanin in the sample. Although high performance liquid chromatography is a simple and economical method for analyzing anthocyanin and anthocyanidin, various anthocyanidins and anthocyanidin can not realize baseline separation on a chromatogram map under the influence of a chromatographic column, a mobile phase and a detector, and the existing reversed-phase liquid chromatography ultraviolet detector method can only analyze 8 anthocyanidins and anthocyanidin simultaneously. There is a gap from the objective of simultaneously detecting 12 anthocyanins.
With the increasing scale and refinement of the application of anthocyanins, it is necessary to find a more accurate method for detecting and separating various anthocyanins.
Disclosure of Invention
The invention aims to provide a method for detecting anthocyanin, which aims to solve the technical problem that the existing method for detecting anthocyanin cannot realize the detection of all kinds of anthocyanin.
In order to solve the technical problem, the invention provides a method for detecting anthocyanin, which comprises the following steps:
preparing a test solution: preparing a solution of anthocyanin to be tested with the total concentration of 500 mug/mL as a solution to be tested;
and (3) determination: eluting the tested solution by adopting a reverse phase chromatography, and detecting by combining a high-resolution mass spectrum, wherein the conditions of the ultra-high performance liquid chromatography are as follows: the chromatographic column is an octadecyl bonded silica gel column, the column temperature is 25 ℃, the injection amount is 2 mu l, and the mass spectrum scanning range is m/z: 100 to 1000;
the conditions of the mobile phase were: the organic phase was methanol containing 1% formic acid, the aqueous phase was 1% formic acid in water, and the elution was carried out in a gradient at a flow rate of 0.3 mL/min.
Preferably, the volume ratio of the anthocyanin in the solution to be detected is 95:5 methanol-formic acid solution.
Preferably, the reverse phase chromatography is performed using a Hypersil GOLD C18 column.
Further preferably, the reverse phase chromatography has a model of 100mm × 2.1mm and a packed particle size of 1.9 μm.
Preferably, the high resolution mass spectrum is a linear ion trap high resolution mass spectrum.
Further preferably, the flow rate of the sheath gas (N2) of the linear ion trap high resolution mass spectrometer is: 12L/min, auxiliary gas flow (N2): 1.8L/min, evaporation temperature: 400 ℃, ion transfer tube temperature: 400 ℃; capillary voltage: 3000V; secondary mass spectrum fragmentation mode: high energy Collision (CID); energy: 35 percent.
The detection limit of the anthocyanin is 1.73-8.18 ng/mL, which is determined by the signal-to-noise ratio of 3.
The method for detecting the anthocyanin has the quantitative limit of 5.77-27.3 ng/mL determined by the signal-to-noise ratio of 10.
The quantitative detection concentration range of the detection method is 0.0424 mu g/mL-19.8 mu g/mL.
The detection method has a mass error of less than or equal to 2.14ppm for 12 anthocyanin.
Compared with the prior art, the detection method has the advantages that the ultrahigh performance liquid chromatography column with small filling particle size is adopted, so that the separation effect is good, all base lines of 12 kinds of anthocyanin can be separated, and the purpose of full detection of all anthocyanin is achieved. The invention adopts the combination of ultra-high performance liquid phase and high-resolution mass spectrum, the dual-channel detection ensures the detection accuracy, the high resolution and the good separation degree improve the detection precision, and the detection limit is greatly reduced.
Drawings
FIG. 1 is a graph showing the elution effect of anthocyanins of comparative examples of the present invention;
FIG. 2 is a graph showing the elution effect of anthocyanins according to an embodiment of the present invention;
FIG. 3 is a chromatogram of extracted ions of various anthocyanidin standards.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely with reference to the accompanying drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making an invasive task, are within the scope of the present invention.
It should be noted that all the directional indicators (such as upper, lower, left, right, front and rear … …) in the embodiment of the present invention are only used to explain the relative position relationship between the components, the movement situation, etc. in a specific posture (as shown in the drawing), and if the specific posture is changed, the directional indicator is changed accordingly.
It will also be understood that when an element is referred to as being "secured to" or "disposed on" another element, it can be directly on the other element or intervening elements may also be present. When an element is referred to as being "connected" to another element, it can be directly connected to the other element or intervening elements may also be present.
In addition, the descriptions related to "first", "second", etc. in the present invention are for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include at least one of the feature. In addition, technical solutions between various embodiments may be combined with each other, but must be realized by a person skilled in the art, and when the technical solutions are contradictory or cannot be realized, such a combination should not be considered to exist, and is not within the protection scope of the present invention.
The embodiment of the invention provides a method for detecting anthocyanin, which comprises the following steps:
s01, preparing test solution: preparing a solution of anthocyanin to be tested with the total concentration of 500 mug/mL as a solution to be tested;
s02, measurement: eluting the tested solution by adopting a reverse phase chromatography, and detecting by combining a high-resolution mass spectrum, wherein the conditions of the ultra-high performance liquid chromatography are as follows: the chromatographic column is an octadecyl bonded silica gel column, the column temperature is 25 ℃, the injection amount is 2 mu l, and the mass spectrum scanning range is m/z: 100 to 1000;
the conditions of the mobile phase were: the organic phase was methanol containing 1% formic acid, the aqueous phase was 1% formic acid in water, and the elution was carried out in a gradient at a flow rate of 0.3 mL/min.
Specifically, in step S01, the volume ratio of the anthocyanins in the solution to be detected is 95:5 methanol-formic acid solution. Because anthocyanins are greatly affected by the pH of the solvent and are stable under acidic conditions, acidic methanol or ethanol solvents are most commonly used, with the best extraction of acidic methanol. In order to prevent hydrolysis of anthocyanin, attention needs to be paid to the concentration of acid in the extractant, and weak acid such as formic acid or acetic acid is more suitable for extraction of anthocyanin in the sample than hydrochloric acid. Experiments found that 95:5(v: v) methanol-formic acid was the best extractant.
In the specific step S02, the chromatographic column used in the reverse phase chromatography is a Hypersil GOLD C18 chromatographic column.
In a further preferred embodiment, the reverse phase chromatography is of type 100mm × 2.1mm and the packing particle size is 1.9 μm.
Specifically, in the step S02, the high-resolution mass spectrum is a linear ion trap high-resolution mass spectrum.
In a further preferred embodiment, the flow rate of the sheath gas (N2) of the linear ion trap high resolution mass spectrometer is: 12L/min, auxiliary gas flow (N2): 1.8L/min, evaporation temperature: 400 ℃, ion transfer tube temperature: 400 ℃; capillary voltage: 3000V; secondary mass spectrum fragmentation mode: high energy Collision (CID); energy: 35 percent. The ion abundance and stability of the condition obtained by optimizing the primitive conditions are in a proper range. Facilitating the next tests.
The specific operation is to measure a series of mixed standard solutions with 11 mass concentration levels, and a standard curve is drawn by taking the extracted ion peak area (y) of each component as the ordinate and the corresponding mass concentration (x, mu g/mL) as the abscissa. As a result, the 12 kinds of anthocyanidins have good linear relations in a certain mass concentration range, the linear range is wide, and the correlation coefficient (r) is 0.9951-0.9983. Diluting the concentration of the sample step by step, and finally defining a detection limit and a quantification limit standard to obtain the anthocyanin, wherein the detection limit of the anthocyanin detection method is 1.73-8.18 ng/mL, and is determined by the signal-to-noise ratio of 3. The method for detecting the anthocyanin has the quantitative limit of 5.77-27.3 ng/mL determined by the signal-to-noise ratio of 10.
The quantitative detection concentration range of the detection method is 0.0424 mu g/mL-19.8 mu g/mL. The linear correlation coefficients within the range are all equal to or more than 0.9951. Has high correlation, so that the specific content can be accurately obtained according to the test data.
The detection method has a mass error of less than or equal to 2.14ppm for 12 anthocyanin. The error obtained by calculation is very small, and the accuracy is very high.
The anthocyanin detection method provided by the invention adopts the reverse phase column with better separation effect, so that the baseline of the anthocyanin in the detected 12 is separated. Specifically, the optimal extraction solvent is obtained through repeated experiments, so that the extraction efficiency is improved, the extraction error is reduced, the data are counted and sorted to obtain the application range and the calibration curve, and finally the peak attribution of various anthocyanidins is determined by combining high-resolution mass spectrum signals, so that the quantitative detection of the anthocyanidins is realized. Also, the quantitative separation of the anthocyanins can be achieved with the same elution conditions.
Comparative examples
Detection method
Sample pretreatment: the anthocyanin in the sample is extracted by adopting 95:5(v: v) methanol-formic acid as an extracting agent.
Preparing a sample: the extracted sample was prepared as a solution of the anthocyanin to be tested at a total concentration of 500. mu.g/mL.
And (3) testing: eluting the tested solution by adopting a Hypersil GOLD C18 chromatographic column (100mm multiplied by 2.1mm i.d, 1.9 mu m), and detecting by combining a linear ion trap high-resolution mass spectrum, wherein the conditions of the ultra-high performance liquid chromatography are as follows: the chromatographic column is an octadecyl bonded silica gel column, the column temperature is 25 ℃, the injection amount is 2 mu l, and the mass spectrum scanning range is m/z: 100 to 1000; sheath gas (N2) flow rate of the linear ion trap high resolution mass spectrum: 12L/min, auxiliary gas flow (N2): 1.8L/min, evaporation temperature: 400 ℃, ion transfer tube temperature: 400 ℃; capillary voltage: 3000V; secondary mass spectrum fragmentation mode: high energy Collision (CID); energy: 35 percent.
The conditions of the mobile phase were: the organic phase is methanol containing 0.1% formic acid, the aqueous phase is 0.1% formic acid aqueous solution, gradient elution is carried out, the flow rate is 0.3mL/min, and the elution results are shown in figure 1, and the comparison example can not realize the baseline separation of various anthocyanidins;
example 1 detection method
Sample pretreatment: the anthocyanin in the sample is extracted by adopting 95:5(v: v) methanol-formic acid as an extracting agent.
Preparing a sample: the extracted sample was prepared as a solution of the anthocyanin to be tested at a total concentration of 500. mu.g/mL.
And (3) testing: eluting the tested solution by adopting a Hypersil GOLD C18 chromatographic column (100mm multiplied by 2.1mm i.d, 1.9 mu m), and detecting by combining a linear ion trap high-resolution mass spectrum, wherein the conditions of the ultra-high performance liquid chromatography are as follows: the chromatographic column is an octadecyl bonded silica gel column, the column temperature is 25 ℃, the injection amount is 2 mu l, and the mass spectrum scanning range is m/z: 100 to 1000; sheath gas (N2) flow rate of the linear ion trap high resolution mass spectrum: 12L/min, auxiliary gas flow (N2): 1.8L/min, evaporation temperature: 400 ℃, ion transfer tube temperature: 400 ℃; capillary voltage: 3000V; secondary mass spectrum fragmentation mode: high energy Collision (CID); energy: 35 percent.
The conditions of the mobile phase were: the organic phase is methanol containing 1% formic acid, the aqueous phase is 1% formic acid aqueous solution, gradient elution is carried out, the flow rate is 0.3mL/min, the elution result is shown in figure 2, and the comparison of figure 1 shows that the embodiment of the invention realizes the baseline separation of various anthocyanidins, and the various anthocyanidins are respectively tested to obtain the chromatogram of the extracted ions of the standard sample, which is shown in figure 3;
example 2 Linear Range, detection Limit and quantitation Limit
The series of mixed standard solutions of 11 mass concentration levels were measured, and a standard curve was plotted with the extracted ion peak area (y) of each component as the ordinate and the corresponding mass concentration (x, μ g/mL) as the abscissa. The result shows that 12 kinds of anthocyanidins have good linear relation in a certain mass concentration range, the linear range is wide, and the correlation coefficient (r) is 0.9951-0.9983. And diluting the concentration of the sample step by step, determining the detection limit of the substance to be detected by using a signal-to-noise ratio (S/N) ═ 3, determining the quantification limit of the substance to be detected by using an S/N ═ 10, and obtaining 12 kinds of anthocyanin with the LOD of 1.73-8.18 ng/mL and the LOQ of 5.77-27.3 ng/mL.
Example 3 recovery and relative standard deviation
Respectively taking blueberries, chrysanthemum, tea beverages, fruit juice, wine and purple sweet potatoes, adding a standard curve middle concentration point (1.00 mu g/mL), carrying out parallel determination for 3 times after treatment according to an optimized method, and calculating the average recovery rate and the relative standard deviation of each matrix. The result shows that the recovery rate of the method is between 61.9 and 113 percent, and the relative standard deviation is less than or equal to 8.23 percent. The recovery rate of anthocyanidin is lower than that of anthocyanin, and probably causes the stability of anthocyanidin to be inferior to that of anthocyanin. The method has good accuracy and precision on anthocyanin, and can meet the requirement of detecting anthocyanin substances in fruits, vegetables and beverages.
Example 4 Process stability
After the standard substance with the same concentration is placed for 0 hour, 2 hours, 4 hours, 8 hours, 12 hours, 24 hours, 48 hours and 72 hours, the stability of 12 kinds of anthocyanidins is inspected by taking the peak area as a parameter, the peak areas of anthocyanin and anthocyanidin decrease with the longer time of placement, and the descending trend of anthocyanidin is more obvious than that of anthocyanin. And the relative standard deviation of the peak area in 72h is less than or equal to 7.77 percent, which shows that the stability of the 12 kinds of anthocyanin in 72h is good under the method.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. The method for detecting the anthocyanin is characterized by comprising the following steps of:
preparing a test solution: preparing a solution of anthocyanin to be tested with the total concentration of 500 mug/mL as a solution to be tested;
and (3) determination: eluting the tested solution by adopting a reverse phase chromatography, and detecting by combining a high-resolution mass spectrum, wherein the conditions of the ultra-high performance liquid chromatography are as follows: the chromatographic column is an octadecyl bonded silica gel column, the column temperature is 25 ℃, the injection amount is 2 mu l, and the mass spectrum scanning range is m/z: 100 to 1000;
the conditions of the mobile phase were: the organic phase was methanol containing 1% formic acid, the aqueous phase was 1% formic acid in water, and the elution was carried out in a gradient at a flow rate of 0.3 mL/min.
2. The method for detecting anthocyanidin according to claim 1, wherein: the volume ratio of the anthocyanin in the tested solution is 95:5 methanol-formic acid solution.
3. The method for detecting anthocyanidin according to claim 1, wherein: the chromatographic column adopted by the reverse phase chromatography is a Hypersil GOLD C18 chromatographic column.
4. The method for detecting anthocyanidin according to claim 3, wherein: the reverse phase chromatography model is 100mm × 2.1mm, and the packing particle size is 1.9 μm.
5. The method for detecting anthocyanidin according to claim 1, wherein: the high-resolution mass spectrum is a linear ion trap high-resolution mass spectrum.
6. The method for detecting anthocyanidin according to claim 5, wherein: sheath gas (N2) flow rate of the linear ion trap high resolution mass spectrum: 12L/min, auxiliary gas flow (N2): 1.8L/min, evaporation temperature: 400 ℃, ion transfer tube temperature: 400 ℃; capillary voltage: 3000V; secondary mass spectrum fragmentation mode: high energy Collision (CID); energy: 35 percent.
7. The method for detecting anthocyanidin according to claim 1, wherein: the detection limit of the detection method is 1.73-8.18 ng/mL, which is determined by the signal-to-noise ratio of 3.
8. The method for detecting anthocyanidin according to claim 1, wherein: the detection method is characterized in that the quantitative limit determined by the signal-to-noise ratio of 10 is 5.77-27.3 ng/mL.
9. The method for detecting anthocyanidin according to claim 1, wherein: the quantitative detection concentration range of the detection method is 0.0424 mu g/mL-19.8 mu g/mL.
10. The method for detecting anthocyanidin according to claim 1, wherein: the detection method has a mass error of less than or equal to 2.14ppm for 12 anthocyanin.
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Application publication date: 20210430 |