CN114062583A - Method and kit for detecting trichothecene toxins and analogs thereof - Google Patents
Method and kit for detecting trichothecene toxins and analogs thereof Download PDFInfo
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- CN114062583A CN114062583A CN202111280950.0A CN202111280950A CN114062583A CN 114062583 A CN114062583 A CN 114062583A CN 202111280950 A CN202111280950 A CN 202111280950A CN 114062583 A CN114062583 A CN 114062583A
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- 229930013292 trichothecene Natural products 0.000 title claims abstract description 96
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- 239000003053 toxin Substances 0.000 title claims abstract description 74
- 231100000765 toxin Toxicity 0.000 title claims abstract description 74
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- 238000000034 method Methods 0.000 title claims abstract description 43
- 239000012634 fragment Substances 0.000 claims abstract description 50
- 238000001514 detection method Methods 0.000 claims abstract description 30
- 238000001819 mass spectrum Methods 0.000 claims abstract description 25
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 19
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- 150000001875 compounds Chemical class 0.000 claims description 30
- 150000002500 ions Chemical class 0.000 claims description 29
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention discloses a method for detecting trichothecene toxins and analogues thereof and a kit thereof, wherein the method for detecting the trichothecene toxins and the analogues thereof comprises the following steps: extracting a sample to be detected so as to obtain a liquid to be detected; carrying out high performance liquid chromatography high resolution mass spectrometry detection on the liquid to be detected so as to obtain a detection result; and judging whether the sample to be detected contains the trichothecene toxins and the analogs thereof based on the mass spectrum multiple characteristic structure fragment data in the detection result. The method can detect known trichothecene toxins and screen potential trichothecene toxins and analogues thereof, has high detection accuracy, is particularly suitable for detecting the trichothecene toxins and the analogues thereof in grains, and is favorable for ensuring the safety of the grains.
Description
Technical Field
The invention relates to the field of analytical chemistry, in particular to a method for detecting trichothecene toxins and analogues thereof and a kit for detecting trichothecene toxins and analogues thereof.
Background
Mycotoxins seriously harm human and animal safety, and people lack cognition and supervision on unknown novel mycotoxins and derivatives thereof. Mycotoxins are commonly found in cereals and their products, and in particular new mycotoxins and their derivatives are not known and are difficult to detect and detect by prior art means due to their low content. For the detection of mycotoxins, conventional analytical methods include ultraviolet spectroscopy, infrared spectroscopy, enzyme-linked immunosorbent assay (ELISA), nuclear magnetic resonance spectroscopy (NMR), and the like. Among them, nuclear magnetic resonance is the most commonly used method for identifying unknown mycotoxins, and structural information of unknown compounds can be obtained by analyzing a first-order NMR spectrum and a second-order NMR spectrum. However, the nuclear magnetic resonance method has high requirements on the sample size and purity of the detected object, and the unknown mycotoxin is often low in content and exists in a complex food matrix, so that the nuclear magnetic resonance detection requirements are difficult to meet. ELISA utilizes antigen-antibody specific immunoreaction to discover unknown compounds, and documents report that deoxynivalenol-3-glucoside and acylated derivatives of deoxynivalenol can generate cross reaction with a deoxynivalenol enzyme immunoassay kit, so that a detection response value is higher than the actual concentration of the deoxynivalenol, and the existence of the derivatives is discovered. However, this method does not provide the information needed to infer the molecular weight of a compound and its structure, and therefore does not infer the structure of an unknown compound. The existing traditional method can not accurately obtain the structural information of the compound, so that unknown risk substances can not be found, and the technical requirements of the detection of unknown mycotoxin and derivatives thereof can not be met.
Therefore, establishing a method capable of detecting and identifying trace unknown mycotoxins in various cereals and grains, particularly a method for detecting trichothecene toxins, is of great significance.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art. Therefore, one purpose of the invention is to provide a method for detecting trichothecene toxins and analogues thereof, which can detect known trichothecene toxins and screen potential trichothecene toxins and analogues thereof with high detection accuracy, is particularly suitable for detecting the trichothecene toxins and analogues thereof in grains, and is favorable for ensuring the safety of the grains.
It should be noted that the present invention is completed based on the following work of the inventors:
the inventor finds that 8 trichothecene toxins (diacetyl-cutting fusarenol (DAS), new solanum fusarenol (NEO), T-2 toxin (T-2), HT-2 toxin (HT-2), fusarenol (F-X), Deoxynivalenol (DEO), 3-acetyl deoxynivalenol (3ADON), 15-acetyl deoxynivalenol (15ADON)) are all trichothecene toxins. According to the analysis of the mass spectrum cracking law, the cracking behaviors of the A-type trichothecene toxin compound and the B-type trichothecene toxin compound are similar, but the cracking behaviors of the similar compounds are the same, and the characteristic fragments generated by the two compounds are slightly different due to the different numbers of the substituent groups (see figure 1). Therefore, the multiple characteristic fragments of trichothecene toxins are divided into 4 groups (see table 1), the abundance ratio is more than 80%, the mass precision is within 5ppm, and the fragments can be used as the multiple characteristic structure fragments of trichothecene toxin compounds.
TABLE 1
Thus, according to one aspect of the invention, there is provided a method of detecting trichothecene toxins and analogues thereof. According to an embodiment of the invention, the method comprises: extracting a sample to be detected so as to obtain a liquid to be detected; carrying out high performance liquid chromatography high resolution mass spectrometry detection on the liquid to be detected so as to obtain a detection result; and judging whether the sample to be detected contains the trichothecene toxins and the analogs thereof based on the mass spectrum multiple characteristic structure fragment data in the detection result.
According to the method for detecting the trichothecene toxins and the analogs thereof, disclosed by the embodiment of the invention, not only can known trichothecene toxins be detected, but also potential trichothecene toxins can be screened, and the trichothecene toxin structural analogs containing mother nucleus structures of the type A and type B trichothecene toxins can be detected, so that the detection accuracy is high, the method is particularly suitable for detecting the trichothecene toxins and the analogs thereof in grains, and the safety of the grains is favorably ensured.
In addition, the method for detecting trichothecene toxins and analogues thereof according to the above embodiment of the invention may further have the following additional technical features:
according to the embodiment of the invention, the sample to be detected is grain.
According to an embodiment of the invention, the mass spectrometry multiple feature fragment data comprises mass-to-charge ratios and abundance ratios of multiple feature fragment ions.
According to an embodiment of the invention, the mass to charge ratio of the multiple feature fragment ions is at least one of 384.2017, 400.1966, 442.2435, 484.2541, 355.1387, 297.1333, 339.1438 and 356.1704.
According to an embodiment of the present invention, the abundance ratio of the multiple feature structure fragment ions is not less than 80%.
According to the embodiment of the invention, the mass spectrum multiple characteristic structure fragments are a type A trichothecene toxin compound shown in a formula I and a type B trichothecene toxin compound shown in a formula II.
Wherein R is1、R2、R3And R4Each independently is H, halo, hydroxy, alkyl, heteroalkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, alkoxy, alkyl-OC (═ O) -, alkyl-C (═ O) -, carbamoyl, alkyl-OS (═ O) r-, alkyl-S (═ O) rO-, alkyl-S (═ O) r-, or aminosulfonyl.
According to the embodiment of the invention, the chromatographic conditions of the high-resolution mass spectrum of the high performance liquid chromatography are as follows: a chromatographic column: ZORBAX Eclipse Plus C18A chromatographic column; flow rate: 0.3 mL/min.
According to the embodiment of the invention, the chromatographic mobile phase of the high-resolution mass spectrum of the high performance liquid chromatography is as follows: mobile phase a was 0.1% acetic acid and 2mM aqueous ammonium acetate and mobile phase B was methanol.
According to an embodiment of the invention, the chromatographic elution of the high resolution mass spectrum of high performance liquid chromatography is a gradient elution.
According to the embodiment of the invention, the elution condition of the gradient elution is 0-2.0 min and 10% of B; 2.0-3.0 min, 10-20% of B; 3.0-7.0 min, 20-24% B; 7.0-10.5 min, 24-30% B; 10.5-13.5 min, 30-60% B; 13.5-15.0 min, 60-70% B; 15.0-18.0 min, 70-75% B; 75-100% B for 18.0-18.1 min; 18.1-21.0 min, 100% B; 21.0-22.0 min, 100-10% B.
According to the embodiment of the invention, the mass spectrum conditions of the high-resolution mass spectrum of the high performance liquid chromatography are as follows: an ion source: electrospray ion source ESI +; scanning mode: full MS/dd-MS2A scanning mode; capillary voltage: 3.2 kV; ion source temperature: at 320 ℃.
According to an embodiment of the present invention, the trichothecene toxins and analogues thereof are at least one selected from the group consisting of trichothecenes, i.e., ribeoxylnol, neosolanum seudolium enol, T-2 toxin, HT-2 toxin, fusarenol, deoxynivalenol, 3-acetyl deoxynivalenol and 15-acetyl deoxynivalenol.
According to another aspect of the invention, the invention provides a kit for detecting trichothecene toxins and analogs thereof. According to an embodiment of the present invention, the kit comprises a reagent, a standard, an auxiliary material or a combination of at least one of the reagents, the standard and the auxiliary material used in the method for detecting trichothecene toxins and analogs thereof.
According to an embodiment of the present invention, the trichothecene toxins and analogues thereof are at least one selected from the group consisting of trichothecenes, i.e., ribeoxylnol, neosolanum seudolium enol, T-2 toxin, HT-2 toxin, fusarenol, deoxynivalenol, 3-acetyl deoxynivalenol and 15-acetyl deoxynivalenol.
Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
Drawings
The above and/or additional aspects and advantages of the present invention will become apparent and readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings of which:
FIG. 1 shows a schematic mass spectrometric fragmentation diagram of trichothecenes type A and B according to one embodiment of the present invention;
FIG. 2 shows a schematic diagram of the mass spectrometric cleavage pattern of a trichothecene toxin according to one embodiment of the present invention, wherein A is a trichothecene toxin type A and B is a trichothecene toxin type B;
FIG. 3 shows a graph illustrating the results of a multiple feature debris screen according to one embodiment of the invention;
FIG. 4 shows a schematic mass spectrometric fragmentation pattern of 1 trichothecene toxin discovered in accordance with one embodiment of the present invention;
FIG. 5 shows a schematic representation of the structure speculation for the 4 trichothecenes found according to one embodiment of the present invention.
Detailed Description
Reference will now be made in detail to embodiments of the present invention, examples of which are illustrated in the accompanying drawings, wherein like or similar reference numerals refer to the same or similar elements or elements having the same or similar function throughout. The embodiments described below with reference to the accompanying drawings are illustrative only for the purpose of explaining the present invention, and are not to be construed as limiting the present invention.
It should be noted that the terms "first" and "second" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include one or more of that feature. Further, in the description of the present invention, unless otherwise specified,
according to one aspect of the invention, the invention provides a method for detecting trichothecene toxins and analogs thereof.
According to the method for detecting the trichothecene toxins and the analogs thereof provided by the embodiment of the invention, not only can known trichothecene toxins be detected, but also potential trichothecene toxins can be screened, and the detection accuracy of the structural analogs containing the mother nucleus structures of the a-type and B-type trichothecene toxins is high, so that the technical problem of detection of the risk substances containing the mother nucleus structures of the a-type and B-type trichothecene toxins is solved aiming at the problem of various trichothecene toxins, and the method is particularly suitable for detection of the trichothecene toxins and the analogs thereof in grains and is favorable for ensuring the safety of the grains.
According to the embodiment of the invention, the high performance liquid chromatography high resolution mass spectrometry is adopted to detect the sample to be detected to obtain mass spectrometry data, wherein the high performance liquid chromatography high resolution mass spectrometry can accurately determine the molecular ion mass number and/or fragment ion mass number of the compound contained in the cereal grains, and further, the analysis is carried out according to the accurate fragment ion mass number and the retention time, so that the accuracy of the detection result is better.
Referring to FIGS. 1-5, a method for detecting trichothecene toxins and analogs thereof is illustrated according to an embodiment of the present invention, comprising:
s100 extraction processing
According to an embodiment of the invention, the method comprises: and extracting the sample to be detected so as to obtain the liquid to be detected.
Trichothecenes are relatively heat resistant, require temperatures in excess of 200 ℃ to be destroyed, and are also relatively stable to acids and bases, so that their activity is difficult to destroy by ordinary cooking processes. The foods which are easy to be polluted mainly pollute corns, wheat, rye and other grains, and the corn pollution is the most common. According to the Food and Agricultural Organization (FAO) statistics of the United nations, 25% of agricultural products are contaminated by mycotoxins every year worldwide. Losses of agricultural and industrial materials due to mold contaminating mycotoxins worldwide can reach billions of dollars each year. China is one of the most serious countries in the world polluted by mycotoxins. According to the incomplete statistics of the national food service bureau, the annual grain and oil loss caused by mycotoxin pollution in China is accumulated to be about 3100 ten thousand tons, and the direct economic loss reaches 680-850 billion yuan. Meanwhile, the overproof mycotoxin becomes the biggest obstacle of the European Union of agricultural product export in China, and huge economic loss is caused to grain and oil processing and export enterprises in China. Therefore, the method has important practical significance on the single-ended sporotrichene compounds in the grain, and further, according to the embodiment of the invention, the sample to be detected is the grain. It should be noted that the grain herein includes raw materials such as grains, semi-finished products and finished products, that is, raw materials including grains, and processed products using the raw materials as raw materials, including grains, wheat flour, noodles, bread, and the like.
S200 high-resolution mass spectrometric detection by high performance liquid chromatography
According to the embodiment of the invention, the liquid to be detected is subjected to high performance liquid chromatography high resolution mass spectrometry detection so as to obtain a detection result.
According to the embodiment of the invention, the chromatographic conditions of the high-resolution mass spectrum of the high performance liquid chromatography are as follows: a chromatographic column: ZORBAX Eclipse Plus C18A chromatographic column; flow rate: 0.3 mL/min.
According to the embodiment of the invention, the chromatographic mobile phase of the high-resolution mass spectrum of the high performance liquid chromatography is as follows: mobile phase a was 0.1% acetic acid and 2mM aqueous ammonium acetate and mobile phase B was methanol.
According to an embodiment of the invention, the chromatographic elution of the high resolution mass spectrum of high performance liquid chromatography is a gradient elution. According to the embodiment of the invention, the elution condition of the gradient elution is 0-2.0 min and 10% of B; 2.0-3.0 min, 10-20% of B; 3.0-7.0 min, 20-24% B; 7.0-10.5 min, 24-30% B; 10.5-13.5 min, 30-60% B; 13.5-15.0 min, 60-70% B; 15.0-18.0 min, 70-75% B; 75-100% B for 18.0-18.1 min; 18.1-21.0 min, 100% B; 21.0-22.0 min, 100-10% B. Therefore, the chromatographic separation effect is good, the subsequent mass spectrum detection is facilitated, and the detection accuracy and precision are high.
According to the embodiment of the invention, the mass spectrum conditions of the high-resolution mass spectrum of the high performance liquid chromatography are as follows: an ion source: electrospray ion source ESI +; scanning mode: full MS/dd-MS2A scanning mode; capillary voltage: 3.2 kV; ion source temperature: at 320 ℃. Therefore, under the conditions of the chromatogram and the mass spectrum, the peak shape obtained by detection is better, the separation of the compounds contained in the grains is facilitated, the detection sensitivity and stability are higher, and the retention time and the abundance ratio of the compounds are more accurate.
S300 analysis processing
And judging whether the sample to be detected contains the trichothecene toxins and the analogs thereof based on the mass spectrum multiple characteristic structure fragment data in the detection result. Based on the multiple characteristic structure fragment scanning, whether the compound in the grain contains the related mother nucleus structure which can cause the safety risk of grain food can be accurately judged. Based on the scanning technology, the trichothecene toxins can be detected, the latent trichothecene toxins can be found, novel trichothecene toxin structural analogues can be detected, the detection accuracy is high, and the method can be effectively used for early warning of grain food safety.
The term "analogue" is used herein to refer to compounds having similarity in chemical structure, and specifically, in this document, "analogue" refers to structural analogues of trichothecenes, including compounds having, but not limited to, a-type and B-type trichothecene mother nucleus structures, and in some embodiments, these analogues can be used to accurately determine whether the compounds in cereal grains contain a-type and B-type trichothecene mother nucleus structures that may cause the safety risk of cereal grains, thereby detecting the risk substances having the same structure as the trichothecenes. According to an embodiment of the present invention, the trichothecene toxins and analogues thereof are at least one selected from the group consisting of trichothecenes, i.e., ribeoxylnol, neosolanum seudolium enol, T-2 toxin, HT-2 toxin, fusarenol, deoxynivalenol, 3-acetyl deoxynivalenol and 15-acetyl deoxynivalenol.
According to the embodiment of the invention, whether trichothecene toxin structural analogs exist in the cereal grains is judged based on the multiple characteristic structure fragments and the abundance ratio of the multiple characteristic structure fragments. That is to say, whether the compound in the grain contains multiple characteristic structure fragments or not is judged, if all the fragments contain the multiple characteristic structure fragments, the abundance ratio of mass spectrum marking fragment ions is judged, and if the abundance ratio of the mass spectrum characteristic fragment ions is the same as that of the known compound and the mass precision is within 5ppm, the grain is indicated to contain the trichothecene family toxin.
According to the embodiment of the invention, whether the trichothecene toxin structural analog exists in the cereal grain is judged based on the fragment ions with multiple characteristic structures in mass spectrum data. Based on the multiple characteristic structure fragment scanning, whether the compound in the grain contains the related mother nucleus structure which can cause the safety risk of grain food can be accurately judged. The inventor conjectures the fragment structure of the same mother nucleus by analyzing the structure of a plurality of trichothecene toxins, and according to the embodiment of the invention, the mass spectrum multiple characteristic structure fragments are the A type trichothecene toxin compound shown in the formula I and the B type trichothecene toxin compound shown in the formula II,
wherein R is1、R2、R3And R4Each independently is H, halo, hydroxy, alkyl, heteroalkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, alkoxy, alkyl-OC (═ O) -, alkyl-C (═ O) -, carbamoyl, alkyl-OS (═ O) r-, alkyl-S (═ O) rO-, alkyl-S (═ O) r-, or aminosulfonyl.
According to an embodiment of the invention, the mass spectrometry multiple feature fragment data comprises mass-to-charge ratios and abundance ratios of multiple feature fragment ions. According to an embodiment of the invention, the mass to charge ratio of the multiple feature fragment ions is at least one of 384.2017, 400.1966, 442.2435, 484.2541, 355.1387, 297.1333, 339.1438 and 356.1704. According to the embodiment of the invention, the abundance ratio of the fragment ions with multiple characteristic structures is not less than 80%, the mass precision is within 5ppm, and the fragment ions can be used as the fragment with multiple characteristic structures of the structural compound. Detecting at least one fragment ion with multiple characteristic structures to estimate the mother nucleus structure of the trichothecene toxin compound, and judging whether the trichothecene toxin and the structural analogue thereof are contained. The fragment ions with the two to three kinds of multiple characteristic structures are detected to estimate the mother nucleus structure of the A-type or B-type trichothecene toxin compound. Mass to charge ratio
According to an embodiment of the present invention, the extraction process includes: mixing the sample to be detected with water, and adding a 0.1% acetonitrile formate solution to obtain a mixture; subjecting the mixture to ultrasonication; and standing the mixture after the ultrasonic treatment, and taking supernatant to perform solid phase extraction treatment so as to obtain the liquid to be detected. For convenience of explanation, the extraction process from the sample will be described with wheat flour as an example. According to one embodiment of the present invention, 2g (to an accuracy of 0.01g) of a wheat flour sample is weighed into a 50mL centrifuge tube, 5mL of ultrapure water is added, and the mixture is vortexed and then allowed to stand. Adding 10mL of 0.1% formic acid acetonitrile solution, carrying out vortex for 2min, carrying out ultrasonic extraction for 10min, standing, and taking 7mL of supernatant to place in a QuEChERS selective dispersion solid phase extraction kit. Vortex for 1min, centrifuge for 5min at 4 deg.C, blow 5mL of supernatant liquid nitrogen to dry, redissolve 1mL of redissolution (mobile phase A/mobile phase B:2/8), filter through 0.22 μm organic membrane, and take 2 μ L for analysis by UHPLC-Q-Orbitrap system.
According to another aspect of the invention, the invention provides a kit for detecting trichothecene toxins and analogs thereof. According to an embodiment of the present invention, the kit comprises a reagent, a standard, an auxiliary material or a combination of at least one of the reagents, the standard and the auxiliary material used in the method for detecting trichothecene toxins and analogs thereof.
According to an embodiment of the present invention, the trichothecene toxins and analogues thereof are at least one selected from the group consisting of trichothecenes, i.e., ribeoxylnol, neosolanum seudolium enol, T-2 toxin, HT-2 toxin, fusarenol, deoxynivalenol, 3-acetyl deoxynivalenol and 15-acetyl deoxynivalenol.
The present invention is described below with reference to specific examples, which are intended to be illustrative only and are not to be construed as limiting the invention.
The scheme of the invention will be explained with reference to the examples. It will be appreciated by those skilled in the art that the following examples are illustrative of the invention only and should not be taken as limiting the scope of the invention. The examples, where specific techniques or conditions are not indicated, are to be construed according to the techniques or conditions described in the literature in the art or according to the product specifications. The reagents or apparatus used are conventional products which are commercially available, e.g. from Sigma, without reference to the manufacturer.
Example 1
The method provided by the embodiment of the invention is used for detecting potential trichothecene toxins and analogues thereof in grains, and comprises the following specific steps:
1. feedstock and apparatus
1.1 standards, reagents and samples
The oxiranol, the new solanum fusarenol, the T-2 toxin, the HT-2 toxin, the fusarenone, the deoxynivalenol, the 3-acetyl deoxynivalenol and the 15-acetyl deoxynivalenol are purchased from Romer corporation of Australia, and the concentration error of a standard product is within 2 percent. The cereal grain samples were from freshly harvested grains in the wheat field. Formic acid and acetic acid were purchased from Thermo Fisher Scientific, usa; chromatographic grade methanol and acetonitrile were purchased from Thermo Fisher Scientific, usa; chromatographic grade ammonium acetate was purchased from Sigma, usa; QuEChERS Selective Dispersion solid phase extraction kit (4g magnesium sulfate, 1g sodium chloride, 1g disodium citrate, 0.5g disodium citrate hydrate) and Dispersion SPE kit (149.9mg PSA,149.9mg C)18EC,900.2mg magnesium sulfate) were purchased from Agilent Technologies, usa.
1.2 sample pretreatment
Grinding and uniformly mixing the cereal grain samples, weighing 2g (accurate to 0.01g) of the samples into a 50mL centrifuge tube, adding 5mL of ultrapure water, swirling and standing. Adding 10mL of 0.1% formic acid acetonitrile solution, carrying out vortex for 2min, carrying out ultrasonic extraction for 10min, standing, and taking 7mL of supernatant to place in a QuEChERS selective dispersion solid phase extraction kit. Vortex for 1min, centrifuge for 5min at 4 deg.C, blow 5mL of supernatant liquid nitrogen to dry, redissolve 1mL of redissolution (mobile phase A/mobile phase B:2/8), filter through 0.22 μm organic membrane, and take 2 μ L for analysis by UHPLC-Q-Orbitrap system.
1.3 instruments
The analysis was performed using a Thermo UltiMate 3000 hplc orbitrap high resolution mass spectrometer Q-active. Column used in the experiment ZORBAX Eclipse Plus C18Column (2.1 mm. times.100 mm, 1.8 μm).
2. Conditions of the experiment
2.1 ultra high performance liquid chromatography high resolution mass spectrometry data analysis
2.1.1 liquid chromatography conditions: the chromatographic column is ZORBAX Eclipse Plus C18A chromatographic column; the mobile phase A is 0.1 percent of acetic acid and 2mM ammonium acetate water solution, the mobile phase B is methanol, and the flow rate is 0.3 mL/min; the mobile phase gradient was: 0-2.0 min, 10% B; 2.0-3.0 min, 10-20% of B; 3.0-7.0 min, 20-24% B; 7.0-10.5 min, 24-30% B; 10.5-13.5 min, 30-60% B; 13.5-15.0 min, 60-70% B; 15.0-18.0 min, 70-75% B; 75-100% B for 18.0-18.1 min; 18.1-21.0 min, 100% B; 21.0-22.0 min, 100-10% B.
2.1.2 Mass Spectrometry conditions: electrospray ion source ESI +; full MS/dd-MS2Scanning mode: capillary voltage 3.2 kV; the ion source temperature was 320 ℃. The mass spectral parameters of the 8 trichothecenes are shown in table 2:
TABLE 2
3 conclusion and discussion
3.1 study of known trichothecene toxins and screening of fragments with multiple characteristic structures according to the law of mass spectrometry
The method comprises the steps of analyzing the structures of 8 known trichothecenes (ribes diacetylenium fusarenol, solanum neoformans fusarenol, T-2 toxin, HT-2 toxin, fusarenone, deoxynivalenol, 3-acetyldeoxynivalenol and 15-acetyldeoxynivalenol) by combining high-resolution Mass spectrometry with Mass Frontier, finding that the trichothecenes have similar mother nucleus structures, and can be divided into type A trichothecenes and type B trichothecenes through the same Mass spectrometry cracking reaction, analyzing by using a Venn diagram to screen out multiple characteristic structure fragments, wherein the abundance is over 80 percent, the Mass precision is within 5ppm, and the trichothecenes can be used as the characteristic structure fragments of the structural compounds (see figure 2).
3.2 multiple feature structure fragment scanning technique for investigation of new structural analogues in actual samples
Screening to obtain 4 groups of fragments with multiple characteristic structures, establishing a fragment scanning technology (see figure 3) with multiple characteristic structures, and finding that structural analogs of trichothecene toxins exist in actual samples by examining the consistency and abundance consistency of the fragments with multiple characteristic structures (see figure 4). From the mass spectrum parent ion and mass spectrum fragment information (see table 3), it can be used to infer structural analogs of the risk species, as shown in fig. 5.
TABLE 3
In conclusion, the multiple characteristic structure fragment scanning technology established by utilizing the multiple characteristic structure fragments in the embodiment of the invention can be used for detecting whether trichothecene toxins and structural analogues thereof exist in grains, thereby solving the safety risk of novel grain food. The method can find problems timely, effectively and scientifically, can realize rapid, accurate and active target identification of potential chemical risks of grains, effectively reduces food safety risks, and realizes breakthrough of potential risk substance detection and analysis technology in grains.
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
While embodiments of the invention have been shown and described, it will be understood by those of ordinary skill in the art that: various changes, modifications, substitutions and alterations can be made to the embodiments without departing from the principles and spirit of the invention, the scope of which is defined by the claims and their equivalents.
Claims (10)
1. A method for detecting trichothecene toxins and analogs thereof, comprising:
extracting a sample to be detected so as to obtain a liquid to be detected;
carrying out high performance liquid chromatography high resolution mass spectrometry detection on the liquid to be detected so as to obtain a detection result; and
a method for judging whether the sample to be detected contains the trichothecene toxins and the analogs thereof based on the mass spectrum multiple characteristic structure fragment data in the detection result,
optionally, the sample to be tested is grain.
2. The method of claim 1, wherein the mass spectrometry multiplexed signature fragment data comprises mass-to-charge and abundance ratios of multiplexed signature fragment ions.
3. The method of claim 2, wherein the mass-to-charge ratio of the multiple feature fragment ions is at least one of 384.2017, 400.1966, 442.2435, 484.2541, 355.1387, 297.1333, 339.1438, and 356.1704,
optionally, the abundance ratio of the multiple feature fragment ions is not less than 80%.
4. The method of claim 2, wherein the mass spectrometry multiplexing signature fragments are a type A trichothecene toxoid compound of formula I and a type B trichothecene toxoid compound of formula II,
wherein R is1、R2、R3And R4Each independently is H, halo, hydroxy, alkyl, heteroalkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, alkoxy, alkyl-OC (═ O) -, alkyl-C (═ O) -, carbamoyl, alkyl-OS (═ O) r-, alkyl-S (═ O) rO-, alkyl-S (═ O) r-, or aminosulfonyl.
5. The method of claim 1, wherein the chromatographic conditions of high performance liquid chromatography high resolution mass spectrometry are:
a chromatographic column: ZORBAX Eclipse Plus C18A chromatographic column;
flow rate: 0.3 mL/min.
6. The method of claim 5, wherein the chromatographic mobile phase of the high performance liquid chromatography high resolution mass spectrometry is: mobile phase a was 0.1% acetic acid and 2mM ammonium acetate aqueous solution, mobile phase B was methanol,
optionally, the chromatographic elution of the high-resolution mass spectrum of the high performance liquid chromatography is gradient elution,
optionally, the elution condition of the gradient elution is 0-2.0 min and 10% of B; 2.0-3.0 min, 10-20% of B; 3.0-7.0 min, 20-24% B; 7.0-10.5 min, 24-30% B; 10.5-13.5 min, 30-60% B; 13.5-15.0 min, 60-70% B; 15.0-18.0 min, 70-75% B; 75-100% B for 18.0-18.1 min; 18.1-21.0 min, 100% B; 21.0-22.0 min, 100-10% B.
7. The method of claim 1, wherein the mass spectrometry conditions of high performance liquid chromatography high resolution mass spectrometry are:
an ion source: electrospray ion source ESI +;
scanning mode: FullMS/dd-MS2A scanning mode;
capillary voltage: 3.2 kV;
ion source temperature: at 320 ℃.
8. The method of claim 1, wherein the trichothecene toxins and analogs thereof are at least one member selected from the group consisting of trichothecenes, namely, ribes diacetylenium sickle enol, neosolanum sickle enol, T-2 toxin, HT-2 toxin, fusarium enone, deoxynivalenol, 3-acetyl deoxynivalenol, and 15-acetyl deoxynivalenol.
9. A kit for detecting trichothecenes and analogues thereof, comprising reagents, standards, auxiliary materials or a combination of at least one of them used in the method for detecting trichothecenes and analogues thereof according to claims 1-9.
10. The kit of claim 9, wherein the trichothecene toxins and analogs thereof are at least one member selected from the group consisting of trichothecenes, namely, ribes diacetylenium sickle enol, neosolanum sickle enol, T-2 toxin, HT-2 toxin, fusarium enone, deoxynivalenol, 3-acetyl deoxynivalenol, and 15-acetyl deoxynivalenol.
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