CN111257448A - Method for analyzing stable hydrogen isotope ratio of non-exchangeable hydrogen in sugar - Google Patents
Method for analyzing stable hydrogen isotope ratio of non-exchangeable hydrogen in sugar Download PDFInfo
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Abstract
The invention provides a method for analyzing stable hydrogen isotope ratio of non-exchangeable hydrogen in sugar, belonging to the technical research field of stable isotopes. The method comprises the following steps: 1) selecting sugar compounds with known stable hydrogen isotope ratio of non-exchangeable hydrogen as working standard, fermenting, converting into ethanol, and measuring the hydrogen isotope ratio of ethanol in the fermentation liquor; 2) establishment of delta2HSugar irreplaceable hydrogen＝a*δ2HEthanol+ b; 3) preparing water solution of sugar to be tested, fermenting to convert sugar into ethanol, and measuring hydrogen of ethanol in sugar fermentation liquid to be testedIsotope ratio; 4) and substituting the hydrogen isotope ratio of the ethanol in the sugar fermentation liquor to be detected into the relation model, and calculating to obtain the stable hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar to be detected. The method is mainly used for analyzing the stable hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar, has the advantages of simple operation, low experiment cost, high analysis speed and efficiency, safety and no risk, and is suitable for analysis and test of mass samples.
Description
Technical Field
The invention belongs to the technical field of stable isotope research, and particularly relates to a method for analyzing stable hydrogen isotope ratio of non-exchangeable hydrogen in sugar.
Background
The hydrogen atoms forming living bodiesThe important elements (C) can be classified into hydrogen/protium (H), deuterium (H)2H) And tritium (f)3H) Wherein H and2h is stable isotope, and hydrogen-containing compounds of different sources have different hydrogen isotope ratios (based on natural fractionation effect of the stable isotope2H/H, denoted as delta2H) And thus of the living matter delta against the background of natural abundance2The H value has important research and application in the fields of climate ecology, hydrology science, court science, food authenticity research and the like.
There are four types of bonding of hydrogen atoms in molecules of living substances (e.g., cellulose, sugar, protein, fat, etc.): the first is directly combined on carbon atoms, the second is directly combined on nitrogen atoms to form amino, the third is directly combined on sulfur atoms to form sulfydryl, and the fourth is directly combined on oxygen atoms to form hydroxyl. Due to the difference in electron clouds of groups formed when different atoms are bonded to hydrogen, from the viewpoint of stable isotope analysis, hydrogen directly bonded to a carbon atom is most closely bonded and does not exchange with hydrogen on other molecules in the surrounding environment, and is called "non-exchangeable hydrogen". However, hydrogen bonds on amine groups, mercapto groups, and hydroxyl groups are relatively unstable and easily undergo hydrogen atom exchange with hydroxyl groups and mercapto groups on other molecules, and thus belong to "exchangeable hydrogen". Since the living body contains a large amount of water, the delta of the living matter is measured2Not only does the H eliminate water interference, but also takes into account the effect of water on the exchangeable hydrogen moieties in the biomass. Therefore, the field of stable isotope analysis generally investigates the δ of the non-exchangeable hydrogen moiety of a living substance2H value to replace delta of the biomass as a whole2And H value.
At present, the delta of the non-exchangeable hydrogen moiety is determined2The H value is corrected by substances with similar chemical structures, or is removed by replacing exchangeable hydrogen atoms of living substances, such as: jeffrey F.Kelly et al determine the overall delta of standards and samples (including feathers, blood, soil organic matter, etc.)2H value, delta due to the non-exchangeable hydrogen part of the known standard substance2H value, calculated to give delta of the non-exchangeable hydrogen part of the sample2H value; l.i. wassenaar et al developed an off-line equilibrium-two-way sampling system analysis method, reacting a feather sample in steam for a certain time to balance exchangeable hydrogen in the sample with hydrogen in the steam, then converting the sample into water and analyzing; john s.roden et al and Marc s.filot et al investigated δ of the non-exchangeable hydrogen moiety of cellulose using the method of l.i.wassenaar2H value; sharp et al studied the delta of the non-exchangeable hydrogen fraction of hair using the above method2H values and for forensic science; peter e. As a result of analysis, organic substances such as feathers, cellulose, and hair, which are the subjects of the study, do not absorb water or hardly absorb water, and therefore hydrogen isotope exchange can be performed by water vapor, and water molecules for equilibrium reaction can be removed by drying and nitrogen blowing.
However, sugar is a substance which is very hygroscopic, and the above method cannot avoid the influence of exchangeable hydrogen in sugar, and also influences the measurement result by hydrogen atoms introduced into non-sugar molecules due to water absorption. In the non-exchangeable hydrogen part of the sugar delta2The research of the analysis method of H mainly comprises two types: john Dunbar [ Dunbar, J., Schmidt, H. -. Measurement of the 2H/1Hratios of the carbon bound hydrogen atoms in sugars, anal. chem.317, 853-857 (1981) doi:10.1007/BF00466937 ] nitrifies the sugar, substitutes the exchangeable hydrogen in the sugar with nitro, and then burns into water, and further obtains the hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar by analyzing the hydrogen isotope ratio of water, and because of the addition of reagents such as concentrated nitric acid, acetic anhydride, and the like, there is a safety risk, and the pretreatment process is complicated; the method is characterized in that Simon Kelly separates and collects fructose molecules in sugar by liquid chromatography, then carries out derivatization treatment, converts the fructose molecules into hexamethylenetetramine, and then carries out gas chromatography-cracking-stable isotope ratio mass spectrometry analysis.
Disclosure of Invention
The invention develops a stable hydrogen isotope ratio delta for analyzing non-exchangeable hydrogen in sugar based on metabonomics and stable isotope analysis technology2The method for H value is simple to operate, rapid in analysis, high in efficiency, safe and risk-free.
The invention provides a method for analyzing stable hydrogen isotope ratio of non-exchangeable hydrogen in sugar, which comprises the following steps:
1) selecting sugar compounds with known stable hydrogen isotope ratio of non-exchangeable hydrogen as working standard, preparing water solution of the sugar compounds, fermenting, converting into ethanol, and measuring hydrogen isotope ratio of ethanol in fermentation liquor;
2) establishing the hydrogen isotope ratio delta of ethanol2HEthanolStable hydrogen isotope ratio delta to non-exchangeable hydrogen in sugar compounds as a working standard2HSugar irreplaceable hydrogenGet δ from the relationship model of2HSugar irreplaceable hydrogen＝a*δ2HEthanol+b；
3) Preparing an aqueous solution of sugar to be detected, fermenting to convert the sugar into ethanol, and determining the hydrogen isotope ratio of the ethanol in the sugar fermentation liquor to be detected;
4) and substituting the hydrogen isotope ratio of the ethanol in the sugar fermentation liquor to be detected into the relation model, and calculating to obtain the stable hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar to be detected.
Further, in step 1), the number of the saccharide compounds as the working standard is at least 3, and the stable hydrogen isotope ratios of the non-exchangeable hydrogens are different from each other.
Further, when preparing the aqueous solution of the sugar compound in the step 1) and the aqueous solution of the sugar to be measured in the step 3), the water sources used are the same, and the hydrogen isotope ratios in the water are the same.
Further, the sugar concentration in the aqueous solution of the sugar compound in the step 1) and the sugar concentration in the aqueous solution of the sugar to be measured in the step 3) are the same; the sugar concentration is 170 g/L-280 g/L.
Further, in the step 1) and the step 3), the fermentation conditions are the same; the method specifically comprises the following steps: adding active dry yeast into water solution of sugar compound or water solution of sugar to be measured, and performing anaerobic fermentation at 30 +/-0.5 ℃ until the fermentation is finished.
Further, the addition amount of the active dry yeast is 0.5 wt%.
Further, in the step 3), a freeze drying mode is adopted for removing the water in the sugar to be detected.
Further, in step 2), step 4), the hydrogen isotope ratio of ethanol was measured by a gas chromatography-fragmentation-stable isotope ratio mass spectrometer (GC-P-IRMS).
Optionally, confirming that the working environment, the air tightness and the vacuum degree of an ion chamber of the gas chromatography-cracking-stable isotope ratio mass spectrum system meet the requirements, and measuring delta by using an inspection instrument2Precision and stability of H, adjusting ion source parameter values as necessary.
Further, the sugar includes glucose, fructose, sucrose, maltose, lactose. Can be used for detecting 5 kinds of sugar specified in the national standard GB 5009.8-2016.
The invention has the following advantages:
based on an isotope fractionation mechanism in a metabolic process, selecting a sugar compound with a known hydrogen isotope ratio of non-exchangeable hydrogen as a working standard, converting the sugar compound into ethanol, determining the hydrogen isotope ratio characteristics in the ethanol, and establishing a relation model between the sugar compound and the ethanol (the known stable hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar compound and the converted hydrogen isotope ratio in the ethanol); and (3) fermenting the aqueous solution of the sugar to be detected to convert the sugar into ethanol, determining the hydrogen isotope ratio of the ethanol, substituting the result into the relation model, and calculating to obtain the stable hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar to be detected.
The method is simple to operate, low in experiment cost, rapid in analysis, high in efficiency, safe and risk-free, and suitable for analysis and test of large-batch samples.
Detailed Description
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
Example 1Establishment of Delta of ethanol in sugar Compound fermentation broth as working Standard2HEthanolWith irreexchangeable hydrogen delta in sugars2HSugar irreplaceable hydrogenIs a relational model
1) Selecting three sugar compound working standard substances which can not exchange delta of hydrogen2HSugar irreplaceable hydrogenThe values are-125.35 ‰, -101.25 ‰, and-80.63 ‰, respectively; among them, the sugar compound of the working standard is preferably glucose, which is not exchangeable for hydrogen delta2HSugar irreplaceable hydrogenValues were determined by the method proposed by John Dunbar et al.
2) Three sugar compounds as working standards are respectively prepared into 200g/L sugar water solution, 0.5g active dry yeast is added, and alcohol fermentation is carried out at 30 +/-0.5 ℃.
3) Centrifuging the fermentation liquid, collecting the clarified liquid, and measuring delta of ethanol in the fermentation liquid by gas chromatography-cracking-stable isotope ratio mass spectrometer2HEthanolThe values, results are shown in Table 1.
TABLE 1. delta. of sugars with ethanol2H comparison results
From the data in Table 1, the delta of ethanol in the fermentation broth can be obtained2HEthanolDelta from non-exchangeable hydrogen in sugars2HSugar irreplaceable hydrogenThe relationship model of (1): delta2HSugar irreplaceable hydrogenValue 0.9848 δ2HEthanol+241.88. Wherein R is2＝0.9854。
Example 2Analysis of hydrogen isotope ratio of non-exchangeable hydrogen in sugar to be tested
Taking 2 sucrose samples and 1 glucose sample as research objects, preparing each sample into 200g/L sugar water solution, adding 0.5g active dry yeast for alcohol fermentation, and measuring delta of ethanol in fermentation liquor2HEthanol assayThe values and results are shown in Table 2.
TABLE 2 Delta of sucrose and glucose fermentation ethanol2HEthanol assayMeasured value
| Index (I) | Sucrose 1# | Sucrose 2# | Glucose |
| δ2HEthanol assay(‰) | -365.69 | -330.18 | -317.03 |
The data in Table 2 were introduced into the relational model in example 1, and the hydrogen irreplaceable δ of the saccharide was calculated2HSugar irreplaceable hydrogen calculationThe values, results are shown in Table 3.
TABLE 3 non-exchangeable hydrogen delta of sugars2HSugar irreplaceable hydrogen calculationCalculated value
| Index (I) | Sucrose 1# | Sucrose 2# | Glucose |
| δ2HSugar irreplaceable hydrogen calculation(‰) | -118.26 | -83.29 | -70.34 |
Example 3Verifying the accuracy of the method of the invention
Selection of delta of non-exchangeable hydrogen2Glucose with known H value (. delta.)2HSugar irreplaceable hydrogen= 132.59) as a test sample, 3 parts of aqueous glucose solution 100g was prepared, 0.5g of active dry yeast was added for fermentation, and δ of ethanol in the fermentation broth was measured respectively2H values, results are shown in Table 4.
TABLE 4 results of ethanol reproducibility measurement in glucose fermentation broth
| Index (I) | Repetition of 1 | Repetition 2 | Repetition of 3 |
| δ2HEthanol assay(‰) | -381.84 | -375.99 | -378.68 |
As can be seen from Table 4, the hydrogen isotope ratio (delta) of ethanol in the three fermentation broths2HEthanol assay) The standard deviation of the standard is 2.93 per thousand, and the method accords with the stable isotope ratio mass spectrometry determination delta2Precision of H value is required. The average measurement result of the three fermentation liquors is-378.84 ‰, and delta is calculated according to the relation model in example 12HSugar irreplaceable hydrogen calculationThe difference value between-131.20 per mill and the given value is only 1.39 per mill, and is within the measuring error range of an instrument, so that the method can accurately measure the hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar.
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 (8)
1. A method for analyzing the stable hydrogen isotope ratio of non-exchangeable hydrogen in a saccharide, comprising the steps of:
1) selecting sugar compounds with known stable hydrogen isotope ratio of non-exchangeable hydrogen as working standard, preparing water solution of the sugar compounds, fermenting, converting into ethanol, and measuring hydrogen isotope ratio of ethanol in fermentation liquor;
2) establishing the hydrogen isotope ratio delta of ethanol2HEthanolStable hydrogen isotope ratio delta to non-exchangeable hydrogen in sugar compounds as a working standard2HSugar irreplaceable hydrogenGet δ from the relationship model of2HSugar irreplaceable hydrogen＝a*δ2HEthanol+b；
3) Preparing an aqueous solution of sugar to be detected, fermenting to convert the sugar into ethanol, and determining the hydrogen isotope ratio of the ethanol in the sugar fermentation liquor to be detected;
4) and substituting the hydrogen isotope ratio of the ethanol in the sugar fermentation liquor to be detected into the relation model, and calculating to obtain the stable hydrogen isotope ratio of the non-exchangeable hydrogen in the sugar to be detected.
2. The method of claim 1,
in step 1), the number of the saccharide compounds as the working standard is at least 3, and the stable hydrogen isotope ratios of the non-exchangeable hydrogen are different from each other.
3. The method of claim 1,
when the aqueous solution of the sugar compound in the step 1) and the aqueous solution of the sugar to be detected in the step 3) are prepared, the used water sources are the same, and the hydrogen isotope ratios in the water are the same.
4. The method of claim 1,
the sugar concentration in the aqueous solution of the sugar compound in the step 1) is the same as the sugar concentration in the aqueous solution of the sugar to be measured in the step 3); the sugar concentration is 170 g/L-280 g/L.
5. The method of claim 1,
in the step 1) and the step 3), the fermentation conditions are the same; the method specifically comprises the following steps: adding active dry yeast into water solution of sugar compound or water solution of sugar to be measured, and performing anaerobic fermentation at 30 +/-0.5 ℃ until the fermentation is finished.
6. The method of claim 1,
in the step 3), the moisture in the sugar to be detected is removed by adopting a freeze drying mode.
7. The method of claim 1,
in the step 2) and the step 4), the hydrogen isotope ratio of the ethanol is determined by a gas chromatography-cracking-stable isotope ratio mass spectrometer.
8. The method of claim 1,
the sugar comprises glucose, fructose, sucrose, maltose and lactose.
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Citations (4)
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|---|---|---|---|---|
| US20110136097A1 (en) * | 2008-05-15 | 2011-06-09 | Ivan Smajlovic | Method for determining origin of alcohol or sugar containing products |
| CN102967661A (en) * | 2012-10-28 | 2013-03-13 | 中国食品发酵工业研究院 | Rapid determination method for oxygen stable isotope of ethanol in alcoholic beverage |
| CN105866312A (en) * | 2016-05-25 | 2016-08-17 | 中国食品发酵工业研究院 | Method for measuring hydrogen isotope ratio of ethanol in grape wine |
| US20160312250A1 (en) * | 2013-11-04 | 2016-10-27 | Bgn Tech Llc | Methods of making vanillin via the microbial fermentation of ferulic acid from eugenol using a plant dehydrogenase |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110136097A1 (en) * | 2008-05-15 | 2011-06-09 | Ivan Smajlovic | Method for determining origin of alcohol or sugar containing products |
| CN102967661A (en) * | 2012-10-28 | 2013-03-13 | 中国食品发酵工业研究院 | Rapid determination method for oxygen stable isotope of ethanol in alcoholic beverage |
| US20160312250A1 (en) * | 2013-11-04 | 2016-10-27 | Bgn Tech Llc | Methods of making vanillin via the microbial fermentation of ferulic acid from eugenol using a plant dehydrogenase |
| CN105866312A (en) * | 2016-05-25 | 2016-08-17 | 中国食品发酵工业研究院 | Method for measuring hydrogen isotope ratio of ethanol in grape wine |
Non-Patent Citations (3)
| Title |
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| PINHAS LINDNER 等: "Characterization of Citrus Honey by Deuterium NMR", 《J. AGRIC. FOOD CHEM》 * |
| 刘昌景等: "头发氢稳定同位素比值检测的标准品选择研究", 《质谱学报》 * |
| 蔡莽劝等: "IRMS和SNIF-NMR技术在食品检测中的应用及展望", 《质量管理》 * |
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