CN111413332A - Saccharide distinguishing method based on natural pigment anthocyanin - Google Patents
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Abstract
The invention discloses a saccharide distinguishing method based on natural extract anthocyanin, belongs to the technical field of detection, constructs a colorimetric array sensor detection system based on anthocyanin color change, and provides a new method for distinguishing different saccharides. Intermolecular interactions between different analytes and different active centers lead to colorimetric changes, producing unique complex responses. The detection target object forms a unique fingerprint, and the whole reaction process is quantified by a visual digital imaging method to realize the process of differential analysis of the sample. According to the colorimetric array sensor constructed based on anthocyanin, safe and harmless anthocyanin is used for replacing a chemical response dye to complete the distinguishing and identifying work of natural saccharides for the first time, and on the basis of successfully dividing saccharides and sugar alcohols in natural saccharides, each saccharide can be clustered independently without any overlapping and misjudgment phenomena.
Description
Technical Field
The invention belongs to the technical field of detection, and particularly relates to a saccharide distinguishing method based on natural extract anthocyanin.
Background
Saccharides, a major biological material, are the largest class of compounds, vary in molecular weight from monosaccharides to polysaccharides, and play a fundamental role in various biological phenomena. In recent years, global soft drink consumption has increased dramatically. High sugar content in soft drinks is associated with certain cardiovascular diseases, obesity, dental caries and diabetes. In view of food safety and health care which people are pursuing increasingly, it is very effective to determine the kind and content of the added saccharides in soft drinks as important indexes for identifying the excellent quality of soft drinks. In addition, in other fields of food engineering, such as food fermentation, quality control is also closely related to carbohydrate analysis. Therefore, there is an increasing interest in analytical detection studies of carbohydrates. Since most sugars have only one functional group, the "hydroxyl", and many isomeric compounds, branched structures, and chromophore-lacking structures are present in the sugar molecule. We can only start with the analysis of both spatial conformation of a certain hydroxyl group and the number of different hydroxyl groups, and the analytical classification identification of carbohydrates is a challenging task. To date, most carbohydrate sensors are based on enzymatic reactions. The interaction of specific enzyme and sugar is usually required to form a traditional substrate-enzyme 'lock-key model', the selectivity is good, but the use of enzyme has important defects such as low durability and reproducibility, and the detection process is expensive and time-consuming, thereby increasing the difficulty of distinguishing each specific sensing unit in a complex mixture. Therefore, there is an urgent need for a practical method to detect and differentiate saccharides to assist in daily, real-time food quality control in the field.
Colorimetric sensor arrays effectively overcome the limitations of conventional enzyme reaction-based array sensors. Consisting of a multi-element sensor, where the sensing material making up the array is typically a chemically responsive dye (porphyrin derivative, pH indicator dye, etc.), structurally similar target analytes can be distinguished by overall cross-response of the corresponding color changes in the sensor elements of the array. However, the conventional chemical dyes have the problems of toxic, teratogenic, carcinogenic and the like, and are not suitable for application in the food industry. The anthocyanin is used as a natural colorant, has wide source and abundant resources, is convenient to extract, and is an effective substitute for a synthetic colorant which has toxic action on human bodies.
Disclosure of Invention
In order to solve the defects of the array sensor in the identification of the carbohydrate, the invention provides a novel method for distinguishing and identifying the carbohydrate, which is low in cost, safe and harmless. A colorimetric array sensor detection system taking natural extract anthocyanin as a sensing element is constructed. The colorimetric array sensor technology is a multidimensional sensing technology, and the molecular interaction between different analytes and different active centers causes the colorimetric change to generate unique composite response. The detection target object forms a unique fingerprint, and the whole reaction process is quantified by a visual digital imaging method to realize the process of differential analysis of the sample.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a saccharide distinguishing method based on natural extract anthocyanin comprises the following specific steps:
(1) and preparing an array sensor: mixing anthocyanins extracted from five different anthocyanidin extraction sources in different proportions to serve as each sensing unit of the colorimetric array sensor, and preparing the colorimetric sensor array with multiple sensing units;
(2) respectively adding prepared 3-nitrophenylboronic acid solution into 11 sugar solutions, wherein the response time is 1-5 minutes, respectively adding the prepared 3-nitrophenylboronic acid solution into the colorimetric sensor array with multiple sensing units in the step (1), placing the reaction solution into 1 ml centrifuge tubes, placing the centrifuge tubes in the same group of experiments on the same plane of a camera box, placing a smart phone in front of a dark box, collecting an array image, obtaining image information (blank analyte solution) before reaction as initial image information, reading the change condition of red, green and blue (RGB) values in the image by using Photoshop CC as characteristic signals representing the chemical property change before and after reaction, introducing the obtained data into SPSS software for linear discriminant analysis, and obtaining a scoring graph of 11 sugars by using characteristic vectors of the first two linear discriminant functions obtained by analysis as a first factor and a second factor respectively, using the first factor as a horizontal coordinate and using the second factor as a vertical coordinate;
distinguishing and detecting sugar substances in an actual sample, namely selecting commercially available beverages with different sugar contents and sugar types, adding 3-nitrophenylboronic acid/phosphate buffer solution with the pH value of 7.4 into the commercially available beverages respectively, reacting for 1-5 minutes, adding the commercially available beverages into the colorimetric sensor array with multiple sensing units in the step (1), fully mixing the commercially available beverages, placing the reaction solution into a 1 ml centrifugal tube, placing the centrifugal tubes for experiments in the same group on the same plane of a camera box, placing a smart phone in front of a dark box, collecting an array image, obtaining image information (blank analyte solution) before reaction as initial image information, reading the change conditions of red, green and blue (RGB) values in the image by using Photoshop CC as characteristic signals representing the chemical property change before and after the reaction, introducing the obtained data into SPSS software for linear discriminant analysis, and obtaining characteristic vectors of the first two linear discriminant functions which are obtained by analysis as a first factor and a second factor as a horizontal coordinate, and obtaining score maps of six commercially available beverages by distinguishing different sugar types well in L and DA 11 graphs;
further, the anthocyanin extracting solution in the step (1) is extracted from dried lycium ruthenicum, dried carnation flower tea, dried myosotis sylvatica flower tea, dried mulberry fruit or dried Chinese rose flower tea; the extraction method specifically comprises the steps of respectively crushing the raw materials, placing the obtained dry powder raw materials in a brown bottle to be stored in a dark place, selecting anhydrous ethanol with the mass fraction of 70% as an extracting agent, and mixing the extracting agent with the raw materials according to the material-liquid ratio of 1-2: mixing 20-30g/ml, leaching in a water bath at 50 ℃ for 3-5h, taking out, performing suction filtration by using a vacuum suction filtration device to obtain a pigment leaching solution, performing rotary evaporation and concentration at 50 ℃, and mixing the pigment leaching solution and the pigment leaching solution according to a material-liquid ratio of 2: 5 (wt%) and storing at low temperature in dark place.
Further, the anthocyanidin extracted from different anthocyanidin extraction sources in the step (1) is lycium ruthenicum anthocyanin, carnation anthocyanin, myosotis anthocyanin, mulberry anthocyanin and Chinese rose anthocyanin.
Further, the anthocyanin leaching liquor is added into a reaction system in an amount of 1.5% -2% (V/V) of lycium ruthenicum anthocyanin, 1.5% -2% (V/V) of carnation anthocyanin, 3% -4% (V/V) of myosotis anthocyanin, 1.5% -2% (V/V) of mulberry anthocyanin and 1.5% -2% (V/V) of China rose anthocyanin; the reaction system is a system formed by sugar solution and 3-nitrophenylboronic acid/phosphoric acid buffer solution.
Further, the anthocyanins in the step (1) are mixed according to different proportions, which are specifically as follows:
further, the eleven sugars in the step (2) are fructose, xylose, D-arabinose, mannitol, D-sorbitol, xylitol, galactose, D-ribose, sucrose, maltitol and D-anhydrous glucose; wherein fructose, xylose, D-arabinose, galactose, D-ribose, sucrose, maltitol and D-anhydrous glucose are saccharides, and mannitol, D-sorbitol, xylitol and maltitol are sugar alcohols.
Further, the sugar solution concentration in the step (2) is 25-100mM, the prepared 3-nitrophenylboronic acid solution is 50-200mM, the 3-nitrophenylboronic acid is dissolved in 1-10mM phosphate buffer, and the pH of the solution is adjusted to 7.4 by using 0.5M NaOH;
the 3-nitrophenylboronic acid/phosphate buffer solution with pH 7.4 of 150 mM and the 3-nitrophenylboronic acid with 200mM are dissolved in a phosphate buffer solution with 1-10mM, and the pH of the solution is adjusted to 7.4 with 0.5-1M NaOH.
The principle of the invention is as follows:
under physiological pH, boric acid is tightly combined with a diol-containing high-affinity compound through the formation of boric acid ester, so that the pH of the solution is changed, anthocyanins are different in color under different pH, the molecules of different anthocyanins are subjected to a co-color reaction, and the two color changes are synergistic and interacted, so that sugar can be distinguished only by visual observation.
Compared with the prior art, the invention has the following advantages:
the colorimetric array sensor is widely applied to a distinguishing and identifying method, but no report is found for constructing a sensor by using natural extract anthocyanin as a sensing element. The adoption of healthy and safe natural pigments to replace chemical dyes and the successful application of the natural pigments to the distinguishing and identifying of carbohydrate substances shows that the natural pigments can replace the chemical pigments to be applied to a simple array sensor to distinguish closely related analytes. The differential analysis work of the anthocyanin on the saccharides provides a new idea for the application of the anthocyanin in the field of food analysis and detection.
Drawings
FIG. 1 is a linear discriminant analysis (IDA) spectrum of the response of the colorimetric array sensor to the same concentration of sugar and different concentrations, with 5 parallel experiments;
FIG. 2 is a linear discriminant analysis spectrum of responses of a commercially available beverage and a colorimetric array sensor according to the present invention, wherein experiments are performed in parallel for 5 times.
Detailed Description
In order that the objects and advantages of the invention will be more clearly understood, the invention is further described in detail below with reference to examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
A saccharide distinguishing method based on natural extract anthocyanin comprises the following specific steps:
(1) and preparing an array sensor: dissolving 50-200mM of 3-nitrophenylboronic acid in 1-10mM of phosphate buffer, and adjusting the pH to 7.4 with 0.5-1M of NaOH; mixing the extracted anthocyanin leaching liquor in 16 modes and different proportions.
The anthocyanidin is mixed according to different proportions, and is specifically shown in the following table:
TABLE 1 anthocyanins in various proportions
(2) And differential detection of different saccharides: respectively adding 11 sugar solutions into the 3-nitrophenylboronic acid/phosphate buffer solution in the step (1), wherein the response time is 1-5 minutes, reading the change of red, green or blue values of the colorimetric array sensor, namely delta R, delta G and delta B, converting the color change degree into a numerical value and performing linear discriminant analysis, wherein the linear discriminant analysis is that a data set obtained by using the colorimetric array sensor for different sugars is a given training set, and the training set is projected onto a straight line through a dimension reduction thought of the linear discriminant analysis, so that the projection points of the same kind of sugar data set are as close as possible, and the projection points of the different kind of sugar data sets are as far as possible. And (4) deriving a linear discriminant function, arranging the eigenvalues from large to small, and taking the eigenvectors corresponding to the two former eigenvalues, namely the linear discriminant function. Reducing the data of the training set to a two-dimensional space by using the two linear discriminant functions, namely an obtained score map, and realizing the identification and distinguishing work of eleven saccharides through the score map;
(3) and distinguishing and detecting the carbohydrate substances in the actual sample: adding six commercially available drinks with different sugar contents and sugar types into the 3-nitrophenylboronic acid/phosphate buffer solution in the step (1) respectively, wherein the reaction time is 1-5 minutes. Reading the change of the red, green or blue value of the colorimetric array sensor, namely delta R, delta G and delta B, converting the color change degree into a numerical value and performing linear discriminant analysis, wherein the linear discriminant analysis is that different saccharides use a data set obtained by the colorimetric array sensor as a given training set, and the training set is projected onto a straight line through the dimension reduction thought of the linear discriminant analysis, so that the projection points of the same kind of saccharide data sets are as close as possible, and the projection points of the different kind of saccharide data sets are as far away as possible. And (4) deriving a linear discriminant function, arranging the eigenvalues from large to small, and taking the eigenvectors corresponding to the two former eigenvalues, namely the linear discriminant function. And reducing the data of the training set to a two-dimensional space by using the two linear discriminant functions, namely obtaining a score map, and realizing the identification and distinguishing work of six kinds of commercially available beverages with different sugar types and contents through the score map.
Example 1 identification and differentiation of eleven saccharides
The method comprises the steps of adding 100mM fructose, xylose, D-arabinose, mannitol, D-sorbitol, xylitol, galactose, D-ribose, sucrose, maltitol and D-anhydrous glucose solution into the 3-nitrophenylboronic acid/phosphate buffer solution for 1-5 minutes, adding the sensing units (anthocyanin extract) of the colorimetric array sensor respectively for mixing reaction, and carrying out reaction in a 1m L centrifugal tube, wherein the sensing units of the colorimetric array sensor for detecting the saccharides react with different saccharides to generate different color changes respectively, the centrifugal tube of an experiment in the same group is placed on the same plane of a camera box, a smart phone is placed in the front of a dark box to collect an array image, image information (analyte solution) before reaction is obtained as blank image information, Photoshop CC is used for reading red, green and blue (RGB) values in the image as characteristic signals of chemical property changes before and after reaction, Photoshop CC is used for reading RGB values of the RGB values of each mixed reaction system, the experiment is carried out for 635 times in parallel, the red, green and blue (RGB) values in the image are read as characteristic signals of chemical property changes before reaction, the sugar, the second color of sugar, the sugar is further processed as a linear characteristic change of sugar, the second component of sugar, the sugar alcohol is further processed by a linear glucose sensor component, the second component, the sugar component is analyzed by a linear glucose sensor, the second component of sugar component is separated by a linear glucose sensor, and the second component is further analyzed by a linear sugar component identification factor, the second component identification software is carried out, the second component identification software, the second component identification factor is carried out, the second component identification software is carried out, the second component identification is carried out.
Example 2 achieving differentiation of carbohydrates in actual samples
Adding the 3-nitrophenylboronic acid/phosphate buffer solution in the step (1) into six commercially available beverages respectively, wherein the reaction time is 1-5 minutes. Then anthocyanin as described above was added and mixed well. The reaction solution was placed in 1 ml centrifuge tubes, and the centrifuge tubes in the same set of experiments were placed on the same plane of the camera box. The smart phone is placed in front of a dark box, and an array image is collected. Pre-reaction image information (blank analyte solution) was obtained as initial image information. Photoshop CC is used for reading red, green and blue (RGB) values in the image as characteristic signals for representing the change of chemical properties before and after reaction. Reading RGB values of each mixed reaction system through Photoshop CC, paralleling experiments for 5 times, carrying out digital processing on anthocyanin color change caused after reaction, introducing obtained data into SPSS software for linear discriminant analysis, obtaining score maps of different drinks by taking characteristic vectors of the first two linear discriminant functions obtained by analysis as a first factor and a second factor, taking the first factor as a horizontal coordinate and the second factor as a vertical coordinate, and as shown in figure 2, according to different contents and types of added carbohydrate, commercially available drinks with various carbohydrates mixed can also be successfully distinguished by using the constructed colorimetric array sensor, and can be successfully applied to a food system.
Claims (7)
1. A saccharide distinguishing method based on natural extract anthocyanin is characterized in that natural molecules construct an array sensor, and saccharide can be distinguished, and the method comprises the following specific steps:
(1) and preparing an array sensor: mixing anthocyanins extracted from five different anthocyanidin extraction sources in different proportions to serve as each sensing unit of the colorimetric array sensor, and preparing the colorimetric sensor array with multiple sensing units;
(2) and differential detection of different saccharides: respectively adding the prepared 3-nitrophenylboronic acid solution into 11 sugar solutions, wherein the response time is 1-5 minutes, respectively adding the sugar solutions into the colorimetric sensor array with multiple sensing units in the step (1), placing the reaction solution into 1 ml of centrifuge tubes, and placing the centrifuge tubes of experiments in the same group on the same plane of a photographic box; placing the smart phone in front of a dark box, and collecting an array image; acquiring image information before reaction as initial image information; reading change conditions of red, green and blue (RGB) values in an image by using Photoshop CC as characteristic signals representing chemical property changes before and after reaction, introducing the obtained data into SPSS software for linear discriminant analysis, obtaining a score map of 11 kinds of sugar by using characteristic vectors of the first two linear discriminant functions obtained by analysis as a first factor and a second factor respectively, and taking the first factor as a horizontal coordinate and the second factor as a vertical coordinate, wherein 11 kinds of sugar solutions in different kinds can be distinguished through the score map;
differential detection of carbohydrates in real samples: selecting commercially available beverages with different sugar contents and sugar types, respectively adding 3-nitrophenylboronic acid/phosphate buffer solution with the pH of 7.4, reacting for 1-5 minutes, then adding into the colorimetric sensor array with multiple sensing units in the step (1), and fully mixing; placing the reaction solution into a 1 ml centrifuge tube, and placing the centrifuge tubes in the same group of experiments on the same plane of a photographic box; placing the smart phone in front of a dark box, and collecting an array image; acquiring image information before reaction as initial image information; reading the change condition of red, green and blue (RGB) values in the image by using Photoshop CC as a characteristic signal for representing the change of chemical properties before and after reaction; and importing the obtained data into SPSS software for linear discriminant analysis, respectively taking the feature vectors of the first two linear discriminant functions obtained by analysis as a first factor and a second factor, taking the first factor as an abscissa and the second factor as an ordinate to obtain score maps of six commercially available sugar-containing beverages, and distinguishing different types of commercially available beverages through the score maps.
2. The method for distinguishing saccharides according to claim 1, wherein the anthocyanin extract in the step (1) is extracted from dried lycium ruthenicum, dried carnation flower tea, dried myosotis flower tea, dried mulberry fruit or dried rose tea; the extraction method specifically comprises the steps of respectively crushing the raw materials, placing the obtained dry powder raw materials in a brown bottle to be stored in a dark place, selecting anhydrous ethanol with the mass fraction of 70% as an extracting agent, and mixing the extracting agent with the raw materials according to the material-liquid ratio of 1-2: mixing 20-30g/ml, leaching in a water bath at 50 ℃ for 3-5h, taking out, performing suction filtration by using a vacuum suction filtration device to obtain a pigment leaching solution, performing rotary evaporation and concentration at 50 ℃, and mixing the pigment leaching solution and the pigment leaching solution according to a material-liquid ratio of 2: 5 (wt%) and storing at low temperature in dark place.
3. The method for distinguishing saccharides according to claim 1, wherein the anthocyanins extracted from different anthocyanins extraction sources in step (1) are lycium ruthenicum anthocyanins, carnation anthocyanins, myosotis anthocyanins, mulberry anthocyanins and rose anthocyanins.
4. The sugar distinguishing method based on natural extract anthocyanin according to claim 1, wherein the anthocyanin leaching liquor is added into a reaction system in an amount of 1.5% -2% (V/V) of lycium ruthenicum anthocyanin, 1.5% -2% (V/V) of carnation anthocyanin, 3% -4% (V/V) of myosotis sylvatica anthocyanin, 1.5% -2% (V/V) of mulberry anthocyanin and 1.5% -2% (V/V) of China rose anthocyanin; the reaction system is a system formed by sugar solution and 3-nitrophenylboronic acid/phosphoric acid buffer solution.
5. The method for distinguishing saccharides according to claim 1, wherein the anthocyanins in step (1) are mixed in different ratios as follows:
6. the method for distinguishing between sugars as claimed in claim 1, wherein said eleven sugars of step (2) are fructose, xylose, D-arabinose, mannitol, D-sorbitol, xylitol, galactose, D-ribose, sucrose, maltitol and D-anhydroglucose; wherein fructose, xylose, D-arabinose, galactose, D-ribose, sucrose, maltitol and D-anhydrous glucose are saccharides, and mannitol, D-sorbitol, xylitol and maltitol are sugar alcohols.
7. The method for differentiating saccharides based on anthocyanins of a natural extract according to claim 1, wherein the concentration of the sugar solution in the step (2) is 25 to 100mM, the 3-nitrophenylboronic acid solution is prepared by dissolving 3-nitrophenylboronic acid in a solution of 50 to 200mM in a phosphate buffer of 1 to 10mM, and the pH of the solution is adjusted to 7.4 with 0.5M NaOH;
the 3-nitrophenylboronic acid/phosphate buffer solution with pH 7.4 of 150 mM and the 3-nitrophenylboronic acid with 200mM are dissolved in a phosphate buffer solution with 1-10mM, and the pH of the solution is adjusted to 7.4 with 0.5-1M NaOH.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112268899A (en) * | 2020-10-15 | 2021-01-26 | 成都中医药大学 | Method for rapidly identifying fritillaria medicinal materials |
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