CN115201348A - Method for identifying sialic acid sources in cubilose and cubilose products - Google Patents
Method for identifying sialic acid sources in cubilose and cubilose products Download PDFInfo
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- CN115201348A CN115201348A CN202110394503.1A CN202110394503A CN115201348A CN 115201348 A CN115201348 A CN 115201348A CN 202110394503 A CN202110394503 A CN 202110394503A CN 115201348 A CN115201348 A CN 115201348A
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Abstract
The invention provides a method for identifying sialic acid sources in cubilose and cubilose products, belonging to the technical field of food adulteration detection. The method comprises the following steps: 1) Separating and extracting sialic acid in the cubilose product sample to be detected; 2) Measuring nitrogen stable isotope ratio (delta) of sialic acid in cubilose product sample to be tested 15 N); 3) Determination of the nitrogen stable isotope ratio (delta) of native sialic acid 15 N) distribution range; 4) Comparing the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2) with the distribution range obtained in the step 3), and if the sum of the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2) and 0.6 per thousand is smaller than the minimum value of the distribution range, determining that the sialic acid in the sample is a non-cubilose source; adding 0.6 per mill to the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2)When the latter is greater than or equal to the minimum value of the distribution range, the sialic acid in the sample is considered to be of non-cubilose origin. The method is simple, rapid in analysis and low in cost.
Description
Technical Field
The invention belongs to the technical field of food adulteration detection, and particularly relates to a method for identifying sialic acid sources in cubilose and cubilose products.
Background
Sialic acid (sialic acid) is an acidic amino sugar containing 9 carbon atoms and having a pyranose structure, and is systematically named 5-amino-3,5-dideoxy-D-glycerol-D-galactononulose. Since the different linkers at carbon position 5 constitute different types of sialic acid, the two most predominant sialic acids are 5-acetylphthaleino-3,5-dideoxy-D-glycerol-D-galactononulose, namely N-acetylphthaleine (Neu 5Ac, neuAc) and 3-deoxy-D-glycerol-D-galactononulose (KDN).
It has been shown that sialic acid plays a very important role in cell interaction, viral infection and glycoprotein stability, for example, sialic acid plays an important physiological role in the body in the form of complexes formed by the connection of sialic acid with proteins and lipids, sialic acid cholesterol can inhibit the occurrence of senile dementia to a certain extent, sialic acid is greatly associated with cerebral ischemia, parkinson's disease and nerve wound healing, and sialic acid derivative Sialyl Lewis X can be used as an important anti-adhesion drug to effectively prevent excessive leukocyte aggregation and treat diseases such as rheumatoid arthritis and septic shock. In addition, sialic acid has been shown to play an important role in the evolutionary processes of organisms, and the structural form and content of sialic acid present in organisms are generally related to the degree of evolution of the organisms. In lower organisms of lower evolution, such as protists and arthropods, the content of sialic acid is lower, but in vertebrates of higher evolution, the degree of polymerization and the content of sialic acid are higher, and the sialic acid content is generally highest in the vertebral fluid and cerebrospinal fluid. Due to the important application value of sialic acid and derivatives thereof in the treatment of influenza, neurological diseases, inflammation, tumors and the like, the market has strong demand for sialic acid, and sialic acid products produced by a synthesis method or a microbial fermentation method also appear.
In fact, sialic acid is naturally present in a variety of biological tissues and metabolites in mammals, with sialic acid compounds being the highest in the nidus Collocaliae. Because the cubilose is a traditional tonic and is popular with consumers because of having the effects of resisting aging and viruses, improving the bone strength, enhancing the dermis thickness and improving the immunity, the value and the price of the cubilose and products thereof are always high, the cubilose and the products thereof are used as special components of the cubilose, sialic acid is used as an important index for grading in GH/T1092-2014 cubilose quality grade, the industry standard of cubilose products is being researched, and products of each grade respectively correspond to different (combined) sialic acid contents. It is known that the value of food is not only reflected in the sensory flavor and nutritional function, but also in the production raw materials, the production process and the production place. Because natural sialic acid is extremely rare, the carrier of the sialic acid and the products thereof are more precious.
Currently, some analysis methods for sialic acid exist in the food field, for example, a chinese patent with publication number CN101806788B provides an invention for determining sialic acid content by using high performance liquid triple tandem quadrupole mass spectrometry (HPLC-qq), and the national standard "liquid chromatography for determining sialic acid in edible bird's nest and products thereof" stipulates a liquid chromatography-ultraviolet detector for determining sialic acid content, and in addition, there are spectrophotometry and gas chromatography. However, the above method only analyzes the sialic acid content in the food product, and cannot confirm whether the sialic acid in the food product is from an exogenous additive or naturally exists, and particularly, many bird's nest products such as instant bird's nest products exist in the current market, and the analysis of the sialic acid source is increasingly becoming an important factor influencing the product value.
Disclosure of Invention
The invention develops a method capable of identifying sialic acid sources in cubilose and products thereof so as to prevent commercial sialic acid products from imitating natural sialic acid of the cubilose.
The invention provides a method for identifying sialic acid sources in cubilose products, which comprises the following steps:
1) Separating and extracting sialic acid in a cubilose product sample to be detected;
2) Determination of nitrogen stable isotope ratio (delta) of sialic acid in test bird's nest product sample 15 N)；
3) Determination of the nitrogen stable isotope ratio (. Delta.) of native sialic acid 15 N) distribution range;
4) Comparing the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2) with the distribution range obtained in the step 3),
if the sum of the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2) and 0.6 per mill is less than the minimum value of the distribution range, determining that the sialic acid in the sample is a non-cubilose source;
and if the sum of the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2) and 0.6 per mill is greater than or equal to the minimum value of the distribution range, determining that the sialic acid in the sample is the source of the cubilose.
Specifically, the natural sialic acid in the cubilose has different isotope characteristics from the exogenously added commercial sialic acid, but because the standard deviation of the nitrogen isotope ratio determined by a stable isotope ratio mass spectrometer is required to be better than 0.3 per thousand, the 95% confidence interval of the nitrogen isotope ratio in the sample is a determined value +/-0.6, and when the 'determined value +0.6 per thousand' is smaller than the distribution range of the natural sialic acid in the cubilose, the exogenous sialic acid is considered to be contained in the sample to be detected, namely the sialic acid in the sample is a non-cubilose source.
Further, in the step 1), the separation and extraction is to extract sialic acid in the cubilose product by adopting a preparation liquid phase technology after pretreating a sample according to a GB/T30636-2014 method.
Further, in the step 1), the preparation liquid phase technology is specifically to inject 2mL of pretreated solution into a preparation liquid chromatograph, collect an effluent liquid containing sialic acid, remove an organic solvent, freeze-dry to obtain solid powder, and store the solid powder for testing. For example, 2mL of the pretreated solution may be injected into a preparative liquid chromatograph, an effluent containing sialic acid may be collected, the organic solvent may be removed, and the resulting solution may be freeze-dried to obtain a solid powder, which may be stored for testing.
Specifically, in the step 1), the liquid phase preparation technology specifically comprises the steps of separating a sample to be separated, collecting an effluent liquid containing sialic acid, removing an organic solvent, freeze-drying to obtain solid powder, and storing the solid powder to be detected.
Further, in the step 1), the bird's nest products include various products containing bird's nests, wherein the bird's nests are also included. The nidus Collocaliae product comprises dried nidus Collocaliae and crystal sugar nidus Collocaliae.
Further, in the step 2), a stable isotope ratio mass spectrometer is adopted to determine the nitrogen stable isotope ratio.
Further, in step 3), the natural sialic acid is derived from real edible bird's nest or a real edible bird's nest product. The real edible bird's nest or the real edible bird's nest product refers to the real edible bird's nest without exogenous sialic acid added. The real cubilose samples are classified according to cubilose quality grades, and the real cubilose without additives collected from cubilose product manufacturers conforms to the specification of 3.1 in GH/T1092-2014.
The invention has the following advantages:
the method for identifying the sialic acid sources in the cubilose and cubilose products provided by the invention is characterized in that a stable isotope ratio mass spectrometer is used for measuring the nitrogen stable isotope ratio of sialic acid, the distribution range of the commercial sialic acid and natural sialic acid nitrogen stable isotope ratio is respectively determined, and the sialic acid nitrogen stable isotope ratio of a sample to be detected is compared with the distribution range to obtain the sialic acid product.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to 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. The embodiments and features of the embodiments of the present invention may be combined with each other without conflict.
Example 1 validation of stable isotope ratio Mass Spectrometry method for determining sialic acid Nitrogen stable isotope ratio in bird's nest preparation
1. Preparation of samples to be tested (mock samples)
1) Taking one of sialic acid, dry cubilose and rock candy cubilose products (No. 1#, no. 2# and No. 3) which are not from cubilose sources as research objects.
2) The sialic acid content of the dry bird's nest and rock candy bird's nest products was determined according to the method in GB/T30636-2014, and the results were 119.51g/kg and 1.83g/kg, respectively.
3) Soaking dry nidus Collocaliae with 10 times of water, and adding non-nidus Collocaliae-derived sialic acid according to 20%, 40%, 60% and 80% of sialic acid content in dry nidus Collocaliae and crystal sugar nidus Collocaliae respectively to obtain simulated samples, wherein the serial numbers of the dry nidus Collocaliae simulated samples are No. 2-1, no. 2-2, no. 2-3 and No. 2-4 respectively; the serial numbers of the rock candy cubilose simulation samples are 3-1#, 3-2#, 3-3# and 3-4#, respectively.
4) Taking 0.1g of sialic acid sample from non-bird's nest source, diluting with 5mL of purified water, taking 10g of each of the dried bird's nest foaming sample and the dried bird's nest simulation sample (2-1 #, 2-2#, 2-3# and 2-4 #), and respectively pre-treating 60g of each of the rock candy bird's nest sample and the rock candy bird's nest simulation sample (3-1 #, 3-2#, 3-3# and 3-4 #). The pretreatment comprises the steps of pretreating a sample according to a GB/T30636-2014 method to obtain a sample solution, injecting 2mL of the sample solution after pretreatment into a prepared liquid phase to separate and purify sialic acid, collecting an effluent liquid containing sialic acid, removing an organic solvent, freeze-drying to obtain solid powder, and storing the solid powder to be tested.
2. Testing of
5) Direct determination of nitrogen stable isotope ratio (delta) of non-bird's nest derived sialic acid without pretreatment using stable isotope ratio mass spectrometry system 15 N), the results of 5 measurements are shown in table 1.
TABLE 1 sialic acid delta from non-bird's nest 15 Direct measurement of N (‰)
| Number of measurements | 1 | 2 | 3 | 4 | 5 | Mean value of | SD |
| δ 15 N(‰) | -6.78 | -6.92 | -6.89 | -6.82 | -6.94 | -6.88 | 0.05 |
Table 1 shows sialic acid delta 15 The stability of the N value determination accords with the analysis requirement of stable isotope characteristics in the food field (SD is less than 0.3 per mill), and the stable analysis of the stable isotope characteristics of sialic acid nitrogen can be realized.
6) Sialic acid samples which are not from bird's nest sources, dry bird's nest foam samples and rock candy bird's nest samples and are collected after pretreatment steps are measured by using a stable isotope standard mass spectrum system, the sialic acid samples are separated and collected for 3 times respectively, and the measurement results are shown in table 2.
TABLE 2 Delta of pre-treated commercial sialic acid 15 N measured value (‰)
The results in Table 2 show that the non-bird's nest derived sialic acid was treated and then re-measured with an average of-6.88%, which differed only by 0.03% from the average of-6.91% directly measured in Table 1, with a negligible difference, indicating that the pretreatment step did not alter the nitrogen isotope characteristics of the sialic acid, and that the sialic acid delta was re-measured after pretreatment of the three samples 15 The standard deviation of the N value is 0.15 per thousand, 0.15 per thousand and 0.21 per thousand respectively, and the standard deviation meets the requirement that the SD is better than 0.3 per thousand.
7) Measurement using stable isotope standard mass spectrometry systemSialic acid delta of pretreated dry cubilose simulation samples (2-1 #, 2-2#, 2-3# and 2-4 #), and rock candy cubilose simulation samples (3-1 #, 3-2#, 3-3# and 3-4 #) 15 The N values and the results are shown in Table 3.
TABLE 3 simulation of sialic acid delta in samples 15 N determination (‰)
| Sample series | δ 15 N(‰) | Sample series | δ 15 N(‰) |
| 2-1# | 0.66 | 3-1# | 1.63 |
| 2-2# | -1.71 | 3-2# | -1.24 |
| 2-3# | -3.75 | 3-3# | -2.99 |
| 2-4# | -5.72 | 3-4# | -5.57 |
The data in Table 3 show that dried and rock candy bird's nests exhibit a negative trend upon addition of non-bird's nest source sialic acid, and statistical analysis shows that delta in the simulated samples 15 The N value is in a significant negative correlation with the addition of the commercial sialic acid, and the correlation coefficient R 2 All are above 0.99, which shows that the method can accurately determine the delta of sialic acid in the cubilose and cubilose products 15 The N value further indicates the source of sialic acid in the bird's nest.
Example 2Dry bird's nestThe method for detecting the source of the sialic acid comprises the following steps:
1) Bird's nest tracing code with ' Chinese bird's nest tracing management service platform ' is collected from bird's nest product manufacturing enterprises "Of Bird's nest samples 24: (The sialic acid is natural sialic acid);
2) Purchasing 3 non-cubilose-derived sialic acid samples as samples to be detected;
3) Purchasing 2 commercially available dry cubilose samples as samples to be detected;
4) Sialic acid delta was determined for each sample according to the method of example 1 15 The value of N;
5) The statistic result shows that the delta of sialic acid in 24 dry cubilose 15 The distribution range of the N value is 1.75-4.36 per mill, and the delta of 3 commercial sialic acid samples 15 The N values are respectively-6.91, -6.37 and-5.23 per mill;
6) Comparison of delta for Dry and non-bird's nest derived sialic acid 15 The distribution range of N-value, in combination with the correlation obtained in example I, indicates that when 9% of sialic acid derived from non-bird's nest was added to the dry bird's nest, δ was calculated from the maximum value (-5.23 ‰) of sialic acid derived from non-bird's nest and the minimum value (1.75 ‰) of sialic acid derived from dry bird's nest 15 The value of N is 1.122 per mill, even if the determination error is 0.6 per mill, the acceptable delta is acceptable 15 The N value of 1.712 per mill does not meet the distribution range of the natural sialic acid in the dry cubilose, and the sialic acid in the dry cubilose is judged not to be all the natural sialic acid but to be added externally.
7) Delta of 2 commercially available samples of dried bird's nest 15 The measured values of N are 1.91 per mill and 2.83 per mill respectively; delta. For the preparation of a coating 15 The results of the measured value N plus 0.3 per mill are all larger than the minimum value of the distribution range of the dry edible bird's nest by 1.75 per mill, so that the sialic acid of 2 dry edible bird's nest samples are all natural sources, and no exogenous addition is detected.
Example 3Bird's nest productThe method for detecting the source of the sialic acid comprises the following steps:
1) Collecting crystal sugar bird's nest from bird's nest product manufacturing enterprise17 products(the sialic acid is natural sialic acid);
2) Purchase of commercial productsCrystal sugar bird's nest products 5As a sample to be tested;
3) Sialic acid delta was determined for each sample according to the method of example 1 15 The value of N;
4) According to statistics, the delta of sialic acid in 17 rock candy cubilose products 15 The distribution range of the N value is 2.39-3.81 per mill;
5) In example 2, the distribution range of 24 dry bird's nests is 1.75-4.36%, because the dry bird's nests are the raw materials of crystal sugar bird's nests, and the delta of the crystal sugar bird's nests in example 3 15 The distribution range of the N value is within the range of dry cubilose, so 1.75-4.36 per mill is taken as the distribution range of the rock candy cubilose in the example;
6) Sialic acid delta in commercial rock candy bird's nest products 15 The results of the N value measurement are shown in Table 4.
TABLE 4 Delta sialic acid in commercially available Crystal sugar bird's nest 15 N measured value (‰)
| Sample numbering | ss-1 | ss-2 | ss-3 | ss-4 | ss-5 |
| δ 15 N(‰) | 1.91 | 2.69 | 1.65 | 3.11 | 3.02 |
As can be seen from Table 4, sialic acid. Delta. Was found in 4 samples other than ss-3 sample 15 The N values are all larger than 1.75 per mill, so that the product can be judged to contain no exogenous sialic acid; sialic acid delta in ss-3 samples 15 N measures 1.65%, but considering that the SD measured by the method is 0.3%, 1.65 +0.6 = 2.25%, greater than the minimum value (1.75%) of the distribution range of dry/rock candy bird's nest, it is judged that no exogenous sialic acid is added to the product either.
The present invention is not limited to the above preferred embodiments, and any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A method for identifying sialic acid sources in a bird's nest product comprises the following steps:
1) Separating and extracting sialic acid in the cubilose product sample to be detected;
2) Determining the nitrogen stable isotope ratio of sialic acid in the cubilose product sample to be detected;
3) Determining the distribution range of the nitrogen stable isotope ratio of the natural sialic acid;
4) Comparing the nitrogen stable isotope ratio of sialic acid in the sample to be detected obtained in the step 2) with the distribution range obtained in the step 3):
if the sum of the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2) and 0.6 per mill is less than the minimum value of the distribution range, determining that the sialic acid in the sample is a non-cubilose source;
and if the sum of the nitrogen stable isotope ratio of the sialic acid in the sample to be detected obtained in the step 2) and 0.6 per mill is greater than or equal to the minimum value of the distribution range, determining that the sialic acid in the sample is the source of the cubilose.
2. The method of claim 1,
in the step 1), the separation and extraction is to extract sialic acid in the cubilose product by adopting a preparation liquid phase technology after pretreatment is carried out according to a GB/T30636-2014 method.
3. The method of claim 2,
in the step 1), the preparation liquid phase technology is specifically to inject the pretreated solution into a preparation liquid chromatograph, collect the sialic acid-containing effluent liquid, remove the organic solvent, freeze-dry the sialic acid-containing effluent liquid to obtain solid powder, and store the solid powder for testing.
4. The method of claim 1,
in the step 1), the cubilose product comprises dry cubilose and rock candy cubilose.
5. The method of claim 1,
in the step 2), a stable isotope ratio mass spectrometer is adopted to measure the nitrogen stable isotope ratio.
6. The method of claim 1,
in the step 3), the natural sialic acid is derived from real cubilose or a real cubilose product.
7. The method of claim 6,
the real cubilose or the real cubilose product is classified according to cubilose quality grades, and the real cubilose without additives collected from cubilose product manufacturers meets the regulation of 3.1 in GH/T1092-2014.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102213714A (en) * | 2011-03-25 | 2011-10-12 | 广西壮族自治区分析测试研究中心 | Detection method for identifying natural taurine and synthesized taurine |
| CN109541115A (en) * | 2018-11-28 | 2019-03-29 | 西北大学 | The high-resolution sequence separation of sialylated sugar chain isomer and accurate quantitative analysis method |
| CN111879846A (en) * | 2020-07-30 | 2020-11-03 | 华南农业大学 | Method for identifying authenticity of bird's nest by using elemental analysis-stable isotope mass spectrometry and application |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102213714A (en) * | 2011-03-25 | 2011-10-12 | 广西壮族自治区分析测试研究中心 | Detection method for identifying natural taurine and synthesized taurine |
| CN109541115A (en) * | 2018-11-28 | 2019-03-29 | 西北大学 | The high-resolution sequence separation of sialylated sugar chain isomer and accurate quantitative analysis method |
| CN111879846A (en) * | 2020-07-30 | 2020-11-03 | 华南农业大学 | Method for identifying authenticity of bird's nest by using elemental analysis-stable isotope mass spectrometry and application |
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