CN108872289B - Manuka honey identification method based on nuclear magnetic resonance technology - Google Patents
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Abstract
The invention belongs to the field of food safety, particularly relates to the field of manuka honey identification, and more particularly relates to a manuka honey identification method based on a nuclear magnetic resonance technology. The Manuka honey identification method based on nuclear magnetic resonance disclosed by the invention can make up for the defects in the existing Manuka honey identification by specific characteristic markers. The method has the advantages of short analysis time, strong integrity, good specificity, strong controllability, high accuracy and the like. The minimum detection amount of the manuka characteristic marker component contained in the manuka honey by using the identification method disclosed by the invention is 10%.
Description
Technical Field
The invention belongs to the field of food safety, particularly relates to the field of manuka honey identification, and more particularly relates to a manuka honey identification method based on a nuclear magnetic resonance technology.
Background
Manuka (Manuka) honey is a precious species of honey peculiar to New Zealand, and is a shrub plant-Manuka (Manuka)Leptospermum scoparium) The nectar is brewed. Because the manuka honey has unique antibacterial activity, can be used for preventing wound infection and helping wound healing, and has higher medicinal value, the manuka honey is more and more favored by consumers in China.
At present, the export of Manuka honey from New Zealand is increased by about 10% every year in the last 10 years, and the value of honey exported from New Zealand is 1.28 hundred million New Zealand yuan in 2013 years. According to the statistics of the bee and farmers association of new zealand, new zealand produces only about 1700-2000 tons of manuka honey per year, while on a global scale up to more than 1 million tons of honey are sold per year on the manuka name. Similarly, the proportion of manuka honey imported to China also increases year by year.
On one hand, in order to obtain the violence, a few illegal traders blend relatively cheap syrup into the pure manuka honey, which causes great negative effects on import and export honey product markets and deceives a large number of consumers, besides syrup adulteration, other types of honey used for manuka honey adulteration are also frequently existed, and the latter is often more difficult to identify. On the other hand, the manuka honey is subjected to quality evaluation and classification according to the antibacterial activity, so that the manuka honey in different grades has huge price difference. Artificially synthesized Methylglyoxal (MGO) or Dihydroxyacetone (DHA) is illegally added into Manuka honey to improve activity and obtain fulling.
The method for identifying Manuka is mainly issued by related departments of Manuka Honey government of New Zealand, and the grade of Manuka honey is evaluated by the content of propionaldehyde ketone (MGO) or Dihydroxyacetone (DHA), but both can be adulterated. Leoptosperin and methyl syringate were found by the new zealand manuka association (UMFHA) to be characteristic compounds of manuka honey and their levels correlated with antibacterial activity. In order to establish a scientific, accurate and reliable manuka honey identification standard, the Ministry of the New Zealand Primary industry (MPI) publishes the identification standards of single-flower manuka honey, multi-flower manuka honey and non-manuka honey in 2017 and 4 months, and finally determines that four compounds, namely 2 '-methoxyacetophenone (2' -MAP), 2-methoxybenzoic acid (2-MBA), 3-phenyllactic acid (3-PA) and 4-hydroxyphenyllactic acid (4-HPA), can be used as indexes for judging the manuka honey. But the judging standard of Manuka honey is not unified, so that the market of honey, namely the Yulong, is mixed.
China has been in 2011 with the mandatory national standard GB 14963-2011 about honey, the quality of honey is judged mainly from three mandatory indexes of moisture, the total amount of fructose and glucose and the content of sucrose, and the standard can be used for judging the quality of Manuka honey. But because the detection parameters of the new national standard are relatively simple, the adulteration of the manuka honey is difficult to effectively identify. The method for adulteration aiming at the new national standard continuously appears, and all indexes of the doped Manuka honey can meet the requirements of the national standard. Meanwhile, the research on manuka honey in China is basically blank at present, which has great influence on supervision and supervision of imported manuka honey and guarantee of legal rights and interests of consumers in China. Therefore, the development of effective and sensitive honey adulteration detection methods is urgent, and domestic related research and standard making are urgently needed for supervision.
The nuclear magnetic resonance analysis technology is used for analyzing the structure and the property of a substance by measuring the characteristic parameters of a nuclear magnetic resonance spectrum line, can not damage the internal structure of a sample to be detected, and is a completely nondestructive detection method. Meanwhile, the nuclear magnetic resonance detection and analysis method has very high resolution and accuracy, and the sample pretreatment is simple, so the method is widely applied to the aspects of physics, chemistry, medical treatment, petrochemical industry, archaeology and the like.
Disclosure of Invention
The invention aims to provide a manuka honey identification method based on nuclear magnetic resonance.
In order to achieve the aim, the invention discloses a manuka honey identification method based on a nuclear magnetic resonance technology, which determines whether a sample to be detected is manuka honey or not by analyzing nuclear magnetic resonance spectrum spectrogram data of the sample to be detected, and is specifically described as follows:
A. when the nuclear magnetic resonance spectrum analysis spectrum simultaneously meets the following conditions, the sample to be detected is manuka honey:
(1) comprises1Two single peaks with chemical shifts delta of H of 2.30 +/-0.05 ppm and 2.38 +/-0.05 ppm;
(2) the height of the single peak at 2.30ppm is higher than that of the single peak at 2.38ppm, and the relative height ratio of the two single peaks is more than or equal to 2.0;
(3) the error range of the spectral peak height does not exceed 10 percent;
B. when the NMR spectrum does not satisfy any of the above conditions (1) to (3), the sample to be detected is not Manuka honey.
Wherein1Two single peaks with chemical shifts delta of 2.30 +/-0.05 ppm and 2.38 +/-0.05 ppm are characteristic markers established by the invention for identifying manuka honey. The characteristic marker is different from four monomer indexes of 2 '-methoxyacetophenone (2' -MAP), 2-methoxybenzoic acid (2-MBA), 3-phenyllactic acid (3-PA) and 4-hydroxyphenyllactic acid (4-HPA) commonly used in the prior art. The components represented by two unimodal as characteristic markers are not a certain monomer compound, but are a mixture with richer index parameters, the two unimodal are obtained by analyzing 114 comb honey samples (including 7 varieties of Manuka honey, Kunzuka honey, Rewa Ruiwa honey, Karmachi honey, Christmas flower honey, Ruta honey and Tawa Ruyi honey) and 50 commercial Manuka honey samples,is a characteristic marker capable of stably marking manuka honey. The peak-out retention time and the relative peak height of a single peak can accurately distinguish Manuka honey, and the single peak has high information content, so that compared with the existing monomer indexes, the single peak-out retention time and the relative peak height can effectively prevent artificial addition of monomer compounds for counterfeiting.
The invention further discloses that the analysis conditions of the nuclear magnetic resonance spectrum are as follows: adopting a BBI probe; measuring temperature: the room temperature is 20-35 ℃; ambient humidity: 20 to 35 percent; observation frequency 400 MHz; pressing water peak by adopting a pre-saturation method; the pulse program is as follows: noesygppr1d is either zg30 or zgpr; spectrum width: 6410 Hz; 90 ° pulse width: pl = 6.45 μ s; pulse delay time: dl = 15 s; the emission center: o1= 4.7; the accumulation times are as follows: 16 or 64.
Furthermore, the invention discloses a preparation method of the nuclear magnetic resonance spectrum analysis sample, which comprises the following steps: adding phosphate buffer solution with the concentration of 0.5-2.0 mol/L into the honey sample solution, wherein the volume ratio of the phosphate buffer solution to the honey sample solution is 800-1500: 100-300, vortex and shake until uniform mixing, adjust the pH value of the solution to 2.5-4.0, and take 600 μ l of the solution into a nuclear magnetic tube.
Preferably, the solution in which the pH of the solution is adjusted is hydrochloric acid or sodium hydroxide.
More preferably, the concentration of the hydrochloric acid or sodium hydroxide is 1.0 mol/L.
Wherein the phosphate buffer solution contains 0.05-0.3% volume fraction of 3-trimethylsilyl-1-propyl sodium sulfonate internal standard solution and 0.1-3.0 mM sodium azide.
More preferably, the invention further discloses a preparation method of the honey sample solution, which comprises the following steps: filtering the melted honey sample through a nylon filter cloth, removing solid impurities in the honey, accurately weighing 0.25 g of the sample in a centrifuge tube, adding 1mL of heavy water, and completely dissolving.
Preferably, the aperture of the nylon filter cloth is 0.10mm-0.14 mm.
In the invention, the melting treatment steps of the honey sample are further preferably as follows: stirring the sample in a laboratory without crystallization uniformly, placing the sample with crystallization in a water bath at the temperature of not more than 60 ℃ under a closed condition, heating, oscillating, stirring uniformly after the sample is completely melted, and cooling to room temperature quickly.
The Manuka honey identification method based on nuclear magnetic resonance disclosed by the invention can make up for the defects in the existing Manuka honey identification by specific characteristic markers. The method has the advantages of short analysis time, strong integrity, good specificity, strong controllability, high accuracy and the like. The minimum detection amount of the manuka characteristic marker component contained in the manuka honey by using the identification method disclosed by the invention is 10%.
The popularization and the implementation of the invention can better determine the speaking right of Chinese laboratories in the technical field of Manuka honey detection, and provide technical support for coping with or countering foreign technical barriers. Meanwhile, scientific basis and data basis are provided for relevant departments in China to further develop the authenticity supervision work of the quality and the source of the Manuka honey and the marked product name, the production place and the processing process. Plays an important role in protecting the interests of consumers.
Drawings
FIG. 1 is the hydrogen nuclear magnetic resonance fingerprint in example 1.
FIG. 2 is a hydrogen nuclear magnetic resonance spectrum of the sample 1 to be examined in example 2.
FIG. 3 is a hydrogen nuclear magnetic resonance spectrum of the sample 2 to be detected in example 2.
FIG. 4 is a hydrogen nuclear magnetic resonance spectrum of the sample 3 to be detected in example 2.
FIG. 5 is a hydrogen nuclear magnetic resonance spectrum of the sample 4 to be detected in example 2.
Detailed Description
In order that the invention may be better understood, we now provide further explanation of the invention with reference to specific examples.
Example 1 determination of characteristic markers
1. Apparatus and device
The experimental facility includes: an Advance 400 type nuclear magnetic resonance spectrometer (Switzerland Bruker), a 14.1T superconducting magnet, a 5mm dual-core z-gradient probe and Topspin 2.3 test control and data processing software; 5mm NMR sample tubes; high speed centrifuge (Sigma, germany); vortex mixer (model XW-80A, shanghai university of medical instrumentation); LP403 analytical balance (sydoris, germany);
the experimental solvents included: deuterated water (deuterium band 99.8%) was purchased from Cambride Isotrope Laboratories, Inc.; sodium 3-trimethylsilanyl-1-propylsulfonate (TSPSA) was purchased from Aldich-Sigma Co; dipotassium hydrogen phosphate and sodium dihydrogen phosphate (guaranteed purity) were purchased from Aldich-Sigma Co.
2. Honey sample collection
The total of 7 species of manuka honey, kunca honey, ruvarez honey, dammar honey, christmas honey, ruta honey, tavarez honey, etc. collected in different producing areas of new zealand were analyzed for a total of 114 comb honey samples, and 50 commercial manuka honey from the new zealand country.
3. Sample preparation
Uniformly stirring commercially available manuka honey, accurately weighing 0.25 g of sample in a centrifuge tube, adding 1mL of heavy water, and completely dissolving; mu.l of the above solution was taken, 100. mu.l of a phosphate buffer solution (pH = 2.0) having a concentration of 0.5 mol/L, containing 0.05% by volume of the internal standard solution of sodium 3-trimethylsilyl-1-propylsulfonate and 0.1 mM of sodium azide, vortexed and shaken until mixed uniformly, and then the pH of the final solution was adjusted to 2.5 with 1.0mol/L of hydrochloric acid and sodium hydroxide, 600. mu.l of which was taken out in a nuclear magnetic tube.
Uniformly stirring a comb honey sample, filtering the comb honey sample by using a nylon filter cloth with the aperture of 0.10mm-0.14mm, removing solid impurities in honey, accurately weighing 0.25 g of sample in a centrifuge tube, adding 1mL of heavy water, and completely dissolving; mu.l of the above solution was taken, 100. mu.l of a phosphate buffer solution (pH = 2.0) having a concentration of 0.5 mol/L, containing 0.05% by volume of the internal standard solution of sodium 3-trimethylsilyl-1-propylsulfonate and 0.1 mM of sodium azide, vortexed and shaken until mixed uniformly, and then the pH of the final solution was adjusted to 2.5 with 1.0mol/L of hydrochloric acid and sodium hydroxide, 600. mu.l of which was taken out in a nuclear magnetic tube.
4. Acquisition of hydrogen nuclear magnetic fingerprint
The instrument comprises the following steps: advanced 400 nuclear magnetic resonance apparatus (brueck, switzerland) equipped with a BBI probe; the measuring temperature (probe temperature) is 20-35 ℃ at room temperature; the environment humidity is 20-35%, and the pulse program is as follows: noesygppr1 d; the spectrum width is 6410 Hz; pulse width of 90 DEG pl = 6.45 μ s, pulse delay time dl = 15 s; emission center O1= 4.7; the number of accumulations is 16 or 64.
Adopting a BBI probe; measuring temperature: the room temperature is 20-35 ℃; ambient humidity: 20 to 35 percent; observation frequency 400 MHz; pressing water peak by adopting a pre-saturation method; the pulse program is as follows: noesygppr1d is either zg30 or zgpr; spectrum width: 6410 Hz; 90 ° pulse width: pl = 6.45 μ s; pulse delay time: dl = 15 s; the emission center: o1= 4.7; the accumulation times are as follows: 16 or 64.
The hydrogen nuclear magnetic resonance spectroscopy spectra of 114 comb honey samples from different origins and 50 commercial manuka honey from new zealand countries were determined separately and superimposed to form a fingerprint as shown in figure 1.
Determining characteristic markers of the manuka honey sample as follows: 1two single peaks with chemical shifts delta of H of 2.30 +/-0.05 ppm and 2.38 +/-0.05 ppm. And further determining that the judging standard of the Manuka honey sample is that the height of a single peak at 2.30ppm is higher than that of a single peak at 2.38ppm, the relative height ratio of the two single peaks is more than or equal to 2.0, and the error range of the spectrum peak intensity is not more than 10%.
Through measurement, the method has the minimum detection amount of 10% of the manuka characteristic marker component contained in the manuka honey.
Example 2
The samples to be tested are respectively marked as 1, 2, 3 and 4.
The samples are pretreated according to their properties, in particular:
uniformly stirring a commercially available honey sample, accurately weighing 0.25 g of the sample in a centrifuge tube, adding 1mL of heavy water, and completely dissolving; mu.l of the above solution was taken, 100. mu.l of a phosphate buffer solution (pH = 2.0) having a concentration of 0.5 mol/L, containing 0.05% by volume of the internal standard solution of sodium 3-trimethylsilyl-1-propylsulfonate and 0.1 mM of sodium azide, vortexed and shaken until mixed uniformly, and then the pH of the final solution was adjusted to 2.5 with 1.0mol/L of hydrochloric acid and sodium hydroxide, 600. mu.l of which was taken out in a nuclear magnetic tube.
Uniformly stirring a comb honey sample, filtering the comb honey sample by using a nylon filter cloth with the aperture of 0.10mm-0.14mm, removing solid impurities in honey, accurately weighing 0.25 g of the sample in a centrifuge tube, adding 1mL of heavy water, and completely dissolving the sample; mu.l of the above solution was taken, 100. mu.l of a phosphate buffer solution (pH = 2.0) having a concentration of 0.5 mol/L, containing 0.05% by volume of the internal standard solution of sodium 3-trimethylsilyl-1-propylsulfonate and 0.1 mM of sodium azide, vortexed and shaken until mixed uniformly, and then the pH of the final solution was adjusted to 2.5 with 1.0mol/L of hydrochloric acid and sodium hydroxide, 600. mu.l of which was taken out in a nuclear magnetic tube.
Collecting the hydrogen nuclear magnetic fingerprint of a sample to be detected according to the following conditions
The instrument comprises the following steps: advanced 400 nuclear magnetic resonance apparatus (brueck, switzerland) equipped with a BBI probe; the measuring temperature (probe temperature) is 20-35 ℃ at room temperature; the environment humidity is 20-35%, and the pulse program is as follows: noesygppr1 d; the spectrum width is 6410 Hz; pulse width of 90 DEG pl = 6.45 μ s, pulse delay time dl = 15 s; emission center O1= 4.7; the number of accumulations is 16 or 64.
Adopting a BBI probe; measuring temperature: the room temperature is 20-35 ℃; ambient humidity: 20 to 35 percent; observation frequency 400 MHz; pressing water peak by adopting a pre-saturation method; the pulse program is as follows: noesygppr1d is either zg30 or zgpr; spectrum width: 6410 Hz; 90 ° pulse width: pl = 6.45 μ s; pulse delay time: dl = 15 s; the emission center: o1= 4.7; the accumulation times are as follows: 16 or 64.
And (3) analysis results:
and respectively carrying out chemical shift calibration on the hydrogen nuclear magnetic resonance spectrum analysis spectrogram of the No. 1-4 sample. The spectra after calibration are shown in FIGS. 2-5. Sample 1 did not contain1H chemical shifts δ were 2.30ppm and 2.38ppm, so sample 1 was judged to be non-manuka; sample 2 is in1Chemical shifts delta of H at 2.30ppm and 2.38ppm, which clearly contain two single peaks,and the peak height of the single peak at 2.30ppm is higher than the peak height of the spectral peak at 2.38ppm, but the peak height ratio of the two peaks is lower than 2, so that sample 2 is judged to be non-manuka; the samples 3 and 4 clearly contain two single peaks with chemical shifts delta of 2.30ppm and 2.38ppm, the peak height ratio of the two peaks in the sample 3 is about 2.6, the peak height ratio of the two peaks in the sample 4 is 3.5, and the two samples both meet the requirement that the peak height ratio of the two peaks is greater than or equal to 2.0, so the samples 3 and 4 belong to manuka honey.
Claims (9)
1. The manuka honey identification method based on the nuclear magnetic resonance technology is characterized by comprising the following steps: the method comprises the following steps of analyzing nuclear magnetic resonance spectrum spectrogram data of a sample to be detected to determine whether the sample to be detected is manuka honey, wherein the specific description is as follows:
A. when the nuclear magnetic resonance spectrum analysis spectrum simultaneously meets the following conditions, the sample to be detected is manuka honey:
(1) comprises1Two single peaks with chemical shifts delta of H of 2.30 +/-0.05 ppm and 2.38 +/-0.05 ppm;
(2) the height of the single peak at 2.30ppm is higher than that of the single peak at 2.38ppm, and the relative height ratio of the two single peaks is more than or equal to 2.0;
(3) the error range of the spectral peak height does not exceed 10 percent;
B. when the NMR spectrum does not satisfy any of the above conditions (1) to (3), the sample to be detected is not Manuka honey.
2. The method for identifying manuka honey based on the nuclear magnetic resonance technology according to claim 1, wherein the analysis conditions of the nuclear magnetic resonance spectrum are as follows: adopting a BBI probe; measuring temperature: the room temperature is 20-35 ℃; ambient humidity: 20 to 35 percent; observation frequency 400 MHz; pressing water peak by adopting a pre-saturation method; the pulse program is as follows: noesygppr1d is either zg30 or zgpr; spectrum width: 6410 Hz; 90 ° pulse width: pl = 6.45 μ s; pulse delay time: dl = 15 s; the emission center: o1= 4.7; the accumulation times are as follows: 16 or 64.
3. The method for identifying manuka honey based on nuclear magnetic resonance technology according to claim 1, wherein the preparation method of the nuclear magnetic resonance spectroscopy sample comprises the following steps: adding phosphate buffer solution with the concentration of 0.5-2.0 mol/L into the honey sample solution, wherein the volume ratio of the phosphate buffer solution to the honey sample solution is 800-1500: 100-300, vortex and shake until uniform mixing, adjust the pH value of the solution to 2.5-4.0, and take 600 μ l of the solution into a nuclear magnetic tube.
4. The manuka honey identification method based on the nuclear magnetic resonance technology of claim 3, wherein the solution for adjusting the pH value of the solution is hydrochloric acid or sodium hydroxide.
5. The manuka honey identification method based on nuclear magnetic resonance technology of claim 4, wherein the concentration of hydrochloric acid or sodium hydroxide is 1.0 mol/L.
6. The method for identifying manuka honey based on nmr technique of claim 3, wherein the phosphate buffer solution contains 0.05-0.3% by volume of 3-trimethylsilyl-1-propylsodium sulfonate internal standard solution and 0.1-3.0 mM sodium azide.
7. The manuka honey identification method based on the nuclear magnetic resonance technology of claim 3, wherein the honey sample solution is prepared by the following steps: filtering the melted honey sample through a nylon filter cloth, removing solid impurities in the honey, accurately weighing 0.25 g of the sample in a centrifuge tube, adding 1mL of heavy water, and completely dissolving.
8. The method for identifying manuka honey based on the nuclear magnetic resonance technology as claimed in claim 7, wherein the nylon filter cloth has a pore size of 0.10mm to 0.14 mm.
9. The method for identifying manuka honey based on the nuclear magnetic resonance technology as claimed in claim 7, wherein the melting treatment step of the honey sample is as follows: stirring the sample in a laboratory without crystallization uniformly, placing the sample with crystallization in a water bath at the temperature of not more than 60 ℃ under a closed condition, heating, oscillating, stirring uniformly after the sample is completely melted, and cooling to room temperature quickly.
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