CN114062583B - Method for detecting trichothecene toxins and analogues thereof and kit thereof - Google Patents
Method for detecting trichothecene toxins and analogues thereof and kit thereof Download PDFInfo
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- 229930013292 trichothecene Natural products 0.000 title claims abstract description 92
- LZAJKCZTKKKZNT-PMNGPLLRSA-N trichothecene Chemical compound C12([C@@]3(CC[C@H]2OC2C=C(CCC23C)C)C)CO1 LZAJKCZTKKKZNT-PMNGPLLRSA-N 0.000 title claims abstract description 89
- 239000003053 toxin Substances 0.000 title claims abstract description 88
- 231100000765 toxin Toxicity 0.000 title claims abstract description 88
- 108700012359 toxins Proteins 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000012634 fragment Substances 0.000 claims abstract description 48
- 238000001514 detection method Methods 0.000 claims abstract description 29
- 238000001819 mass spectrum Methods 0.000 claims abstract description 28
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 238000004896 high resolution mass spectrometry Methods 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 32
- 150000002500 ions Chemical class 0.000 claims description 27
- IDGRYIRJIFKTAN-UHFFFAOYSA-N 3-acetyldeoxynivalenol Natural products CC(=O)OCC12C(O)C(=O)C(C)=CC1OC1C(O)CC2(C)C11CO1 IDGRYIRJIFKTAN-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000010828 elution Methods 0.000 claims description 12
- LINOMUASTDIRTM-QGRHZQQGSA-N deoxynivalenol Chemical compound C([C@@]12[C@@]3(C[C@@H](O)[C@H]1O[C@@H]1C=C(C([C@@H](O)[C@@]13CO)=O)C)C)O2 LINOMUASTDIRTM-QGRHZQQGSA-N 0.000 claims description 11
- 229930002954 deoxynivalenol Natural products 0.000 claims description 11
- LINOMUASTDIRTM-UHFFFAOYSA-N vomitoxin hydrate Natural products OCC12C(O)C(=O)C(C)=CC1OC1C(O)CC2(C)C11CO1 LINOMUASTDIRTM-UHFFFAOYSA-N 0.000 claims description 11
- PNKLMTPXERFKEN-ZIOSACBISA-N mycotoxin ht 2 Chemical compound C([C@]12[C@]3(C)[C@H](O)[C@@H](O)[C@H]1O[C@H]1[C@]3(COC(C)=O)C[C@@H](C(=C1)C)OC(=O)CC(C)C)O2 PNKLMTPXERFKEN-ZIOSACBISA-N 0.000 claims description 9
- IDGRYIRJIFKTAN-HTJQZXIKSA-N 15-acetyldeoxynivalenol Chemical compound C([C@@]12[C@]3(C)C[C@@H](O)[C@H]1O[C@@H]1C=C(C)C(=O)[C@@H](O)[C@@]13COC(=O)C)O2 IDGRYIRJIFKTAN-HTJQZXIKSA-N 0.000 claims description 8
- ADFIQZBYNGPCGY-HTJQZXIKSA-N 3-acetyldeoxynivalenol Chemical compound C([C@]12[C@]3(C)C[C@H]([C@H]2O[C@H]2[C@@]3([C@H](O)C(=O)C(C)=C2)CO)OC(=O)C)O1 ADFIQZBYNGPCGY-HTJQZXIKSA-N 0.000 claims description 8
- ADFIQZBYNGPCGY-UHFFFAOYSA-N Acetyldeoxynivalenol Natural products C1=C(C)C(=O)C(O)C2(CO)C1OC1C(OC(=O)C)CC2(C)C21CO2 ADFIQZBYNGPCGY-UHFFFAOYSA-N 0.000 claims description 8
- BXFOFFBJRFZBQZ-QYWOHJEZSA-N T-2 toxin Chemical compound C([C@@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@H]1[C@]3(COC(C)=O)C[C@@H](C(=C1)C)OC(=O)CC(C)C)O2 BXFOFFBJRFZBQZ-QYWOHJEZSA-N 0.000 claims description 8
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 5
- 239000005695 Ammonium acetate Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 235000019257 ammonium acetate Nutrition 0.000 claims description 5
- 229940043376 ammonium acetate Drugs 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229930191623 Fusarenone Natural products 0.000 claims description 2
- XGCUCFKWVIWWNW-UHFFFAOYSA-N fusarenone Chemical compound CC(=O)OC1C(O)C2OC3C=C(C)C(=O)C(O)C3(CO)C1(C)C21CO1 XGCUCFKWVIWWNW-UHFFFAOYSA-N 0.000 claims description 2
- 235000013305 food Nutrition 0.000 abstract description 12
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 235000013339 cereals Nutrition 0.000 description 25
- 239000004464 cereal grain Substances 0.000 description 15
- 239000012071 phase Substances 0.000 description 13
- 231100000678 Mycotoxin Toxicity 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000002636 mycotoxin Substances 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 241000223218 Fusarium Species 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- 235000021307 Triticum Nutrition 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- UGJAEDFOKNAMQD-DVQDXYAYSA-N (-)-Falcarinol Natural products CCCCCCC\C=C\CC#CC#C[C@@H](O)C=C UGJAEDFOKNAMQD-DVQDXYAYSA-N 0.000 description 4
- UGJAEDFOKNAMQD-MQNTZWLQSA-N (3S,9Z)-1,9-Heptadecadiene-4,6-diyn-3-ol Chemical compound CCCCCCC\C=C/CC#CC#C[C@@H](O)C=C UGJAEDFOKNAMQD-MQNTZWLQSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UGJAEDFOKNAMQD-UHFFFAOYSA-N Falcarinol Natural products CCCCCCCC=CCC#CC#CC(O)C=C UGJAEDFOKNAMQD-UHFFFAOYSA-N 0.000 description 4
- UQEBOJRXTNLPKZ-KHPPLWFESA-N Falcarinone Chemical compound CCCCCCC\C=C/CC#CC#CC(=O)C=C UQEBOJRXTNLPKZ-KHPPLWFESA-N 0.000 description 4
- UQEBOJRXTNLPKZ-UHFFFAOYSA-N Falcarinone Natural products CCCCCCCC=CCC#CC#CC(=O)C=C UQEBOJRXTNLPKZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- JRLHSTVTOOELAF-KRWDZBQOSA-N dehydrofalcarinol Natural products O[C@@H](C=C)C#CC#CCC=CCCCCCC=C JRLHSTVTOOELAF-KRWDZBQOSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 150000003327 trichothecene derivatives Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 3
- XBJFCYDKBDVADW-UHFFFAOYSA-N acetonitrile;formic acid Chemical compound CC#N.OC=O XBJFCYDKBDVADW-UHFFFAOYSA-N 0.000 description 3
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- 239000000203 mixture Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000209149 Zea Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
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- -1 fusarium enol Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- MUACSCLQRGEGOE-OXMYJKDCSA-N 93860-23-2 Chemical compound O1C(=O)\C=C/C=C\C(C(O)C)(C2O)OCC\C2=C\C(=O)OCC23CCC(C)=CC2OC2CC1C3(C)C21CO1 MUACSCLQRGEGOE-OXMYJKDCSA-N 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
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- 230000019771 cognition Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 150000004478 deoxynivalenol derivatives Chemical class 0.000 description 1
- 235000019262 disodium citrate Nutrition 0.000 description 1
- 239000002526 disodium citrate Substances 0.000 description 1
- CEYULKASIQJZGP-UHFFFAOYSA-L disodium;2-(carboxymethyl)-2-hydroxybutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O CEYULKASIQJZGP-UHFFFAOYSA-L 0.000 description 1
- XNZQCYSOYHAYII-UHFFFAOYSA-L disodium;3-carboxy-3-hydroxypentanedioate;hydrate Chemical compound [OH-].[Na+].[Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O XNZQCYSOYHAYII-UHFFFAOYSA-L 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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 analogues thereof comprises the following steps: extracting a sample to be detected so as to obtain a liquid to be detected; performing 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 analogues thereof based on mass spectrum multi-feature structure fragment data in the detection result. The method can detect the known trichothecene toxins, screen potential trichothecene toxins and analogues thereof, has high detection accuracy, is particularly suitable for detecting the trichothecene toxins and analogues thereof in grains, and is beneficial to ensuring the safety of grain foods.
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 the trichothecene toxins and analogues thereof.
Background
Mycotoxins seriously jeopardize human and animal safety, and people lack cognition and supervision of unknown novel mycotoxins and derivatives thereof. Mycotoxins are commonly found in cereal grains and products thereof, particularly unknown novel mycotoxins and derivatives thereof, which are difficult to detect and detect by prior art means due to their low levels. For mycotoxin detection, 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 analysis of primary and secondary NMR spectra. 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 requirement is difficult to meet. ELISA utilizes antigen-antibody specific immune reaction to find unknown compounds, and the literature reports that the dideoxy fusarium alcohol-3-glucoside and the acylated derivative of deoxynivalenol can cross react with the deoxynivalenol ELISA kit to enable the detection response value to be higher than the actual concentration of the deoxynivalenol, so that the existence of the derivative is found. However, this method does not provide the information necessary to infer the molecular weight of the compound and its structure, and therefore cannot infer the structure of an unknown compound. The existing traditional method can not accurately obtain structural information of the compound, so that unknown risk substances can not be found, and the current detection technical requirements for unknown mycotoxins and derivatives thereof can not be met.
It is therefore of great importance to establish a method which is capable of detecting and identifying trace amounts of unknown mycotoxins in various cereal grains, in particular trichothecene toxins.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems existing in the prior art. Therefore, an object of the present invention is to provide a method for detecting trichothecene toxins and analogues thereof, which not only can detect the known trichothecene toxins, but also can screen potential trichothecene toxins and analogues thereof, has high detection accuracy, is particularly suitable for detecting the trichothecene toxins and analogues thereof in grains, and is favorable for guaranteeing the safety of grain foods.
The present invention has been completed based on the following work of the inventors:
The inventors found that 8 trichothecene toxins (diacetyl ribine (DAS), neosolane disease fusarium alcohol (NEO), T-2 toxin (T-2), HT-2 toxin (HT-2), fusarenone (F-X), deoxynivalenol (DEO), 3-acetyl deoxynivalenol (3 ADON), 15-acetyl deoxynivalenol (15 ADON)) were analyzed by the inventors and were trichothecene toxins. According to analysis of mass spectrum cracking rules, the cracking behaviors of the A-type trichothecene type toxin compound and the B-type trichothecene type toxin compound are similar, but the cracking behaviors of the same class of compounds are the same, and the characteristic fragments generated by the two classes of compounds are slightly different due to different numbers of substituents (see figure 1). Therefore, the multiple characteristic fragments of the trichothecene toxins are divided into 4 groups (see table 1), and the abundance is more than 80%, the quality precision is less than 5ppm, and the fragments can be used as the multiple characteristic structural fragments of the trichothecene toxins.
TABLE 1
Thus, according to one aspect of the present 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; performing 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 analogues thereof based on mass spectrum multi-feature structure fragment data in the detection result.
According to the method for detecting the trichothecene toxins and the analogues thereof, disclosed by the embodiment of the invention, not only can the known trichothecene toxins be detected, but also the potential trichothecene toxins can be screened, and the analogues of the trichothecene toxins containing the A-type and B-type trichothecene toxin parent nucleus structures can be detected, so that the detection accuracy is high, the method is particularly suitable for detecting the trichothecene toxins and the analogues thereof in grains, and the grain food safety is guaranteed.
In addition, the method for detecting trichothecene toxins and analogues thereof according to the above embodiments of the present invention may further have the following additional technical features:
According to the embodiment of the invention, the sample to be tested is grain.
According to an embodiment of the invention, the mass spectral multi-feature fragment data includes mass-to-charge ratios and abundance ratios of multi-feature fragment ions.
According to an embodiment of the invention, the mass to charge ratio of the multi-feature fragment ion 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 invention, the abundance ratio of the multi-feature fragment ions is not less than 80%.
According to an embodiment of the invention, the mass spectrum multi-feature fragments are a trichothecene type a toxin compound of formula I and a trichothecene type B toxin compound of formula II.
Wherein R 1、R2、R3 and R 4 are each independently H, halogen, 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 sulfamoyl.
According to an embodiment of the present invention, the chromatographic conditions of the high performance liquid chromatography high resolution mass spectrum: chromatographic column: ZORBAX Eclipse Plus C 18 chromatographic columns; flow rate: 0.3mL/min.
According to an embodiment of the present invention, the chromatographic mobile phase of the high performance liquid chromatography high resolution mass spectrum is: mobile phase a was 0.1% acetic acid and 2mM aqueous ammonium acetate and mobile phase B was methanol.
According to the embodiment of the invention, the chromatographic elution of the high-resolution mass spectrum of the high-performance liquid chromatography is gradient elution.
According to an embodiment of the invention, the elution conditions of the gradient elution are 0～2.0min,10％B;2.0～3.0min,10～20％B;3.0～7.0min,20～24％B;7.0～10.5min,24～30％B;10.5～13.5min,30～60％B;13.5～15.0min,60～70％B;15.0～18.0min,70～75％B;18.0～18.1min,75～100％B;18.1～21.0min,100％B;21.0～22.0min,100～10％B.
According to an embodiment of the present invention, the mass spectrometry conditions of the high performance liquid chromatography high resolution mass spectrometry: ion source: electrospray ion source esi+; scanning mode: full MS/dd-MS 2 scan mode; capillary voltage: 3.2kV; ion source temperature: 320 ℃.
According to an embodiment of the present invention, the trichothecene type toxin and the analogues thereof are at least one selected from the group consisting of trichothecene type toxin, i.e., diacetyl-falcarinol, neosolane falcarinol, T-2 toxin, HT-2 toxin, falcarinone, deoxynivalenol, 3-acetyldeoxynivalenol and 15-acetyldeoxynivalenol.
According to another aspect of the invention, there is provided a kit for detecting trichothecene toxins and analogues thereof. According to an embodiment of the invention, the kit comprises reagents, standards, auxiliary materials or combinations of at least one of the foregoing methods for detecting trichothecene toxins and analogues thereof.
According to an embodiment of the present invention, the trichothecene type toxin and the analogues thereof are at least one selected from the group consisting of trichothecene type toxin, i.e., diacetyl-falcarinol, neosolane falcarinol, T-2 toxin, HT-2 toxin, falcarinone, deoxynivalenol, 3-acetyldeoxynivalenol and 15-acetyldeoxynivalenol.
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 foregoing and/or additional aspects and advantages of the invention will become apparent and may be better understood from the following description of embodiments taken in conjunction with the accompanying drawings in which:
FIG. 1 shows a schematic diagram of mass spectrometry fragmentation of a single-ended-sporulation type A and B toxins according to one embodiment of the present invention;
FIG. 2 shows a schematic diagram of mass spectrometry cleavage rules of a trichothecene type toxin according to one embodiment of the present invention, wherein A is the trichothecene type A toxin and B is the trichothecene type B toxin;
FIG. 3 shows a schematic representation of multiple feature fragment screening results according to one embodiment of the invention;
FIG. 4 shows a schematic representation of mass spectral fragments of 1 single-ended trichothecene toxin found in accordance with one embodiment of the present invention;
figure 5 shows a schematic representation of the structural speculation of the 4 trichothecenes found in accordance with one embodiment of the present invention.
Detailed Description
Embodiments of the present invention are described in detail below, examples of which are illustrated in the accompanying drawings, wherein like or similar reference numerals refer to like or similar elements or elements having like or similar functions throughout. The embodiments described below by referring to the drawings are illustrative only and are not to be construed as limiting the invention.
It should be noted that the terms "first," "second," and "second" are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implying a number of technical features being indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include one or more such feature. Further, in the description of the present invention, unless otherwise indicated,
According to one aspect of the invention, a method for detecting trichothecene toxins and analogues thereof is provided.
According to the method for detecting the trichothecene toxins and analogues thereof, disclosed by the embodiment of the invention, not only can the known trichothecene toxins be detected, but also the potential trichothecene toxins can be screened, and the structural analogues containing the A-type and B-type trichothecene toxin parent nucleus structures can be detected with high detection accuracy, so that the problem of various trichothecene toxin types is solved, the technical problem of detecting risk substances containing the A-type and B-type trichothecene toxin parent nucleus structures is solved, the method is particularly suitable for detecting the trichothecene toxins and analogues thereof in grains, and the method is favorable for guaranteeing the safety of grain foods.
According to the embodiment of the invention, the high-performance liquid chromatography high-resolution mass spectrum is adopted to detect the sample to be detected to obtain mass spectrum data, wherein the high-performance liquid chromatography high-resolution mass spectrum can accurately measure the molecular ion mass number and/or the fragment ion mass number of the compound contained in the grain, and further, the analysis is carried out according to the accurate fragment ion mass number and the retention time, so that the accuracy of a detection result is better.
Referring to FIGS. 1-5, a method of detecting trichothecene toxins and analogs thereof, according to an embodiment of the invention, is illustrated and comprises:
S100 extraction process
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 over 200 ℃ to be destroyed, and are relatively stable to acids and bases, so that their activity is difficult to destroy by ordinary cooking. The food which is easy to be polluted mainly pollutes corn, wheat, rye and other grains, and corn pollution is the most common. According to the statistics of the united nations grain and agricultural organization (FAO), 25% of agricultural products are contaminated with mycotoxins every year worldwide. Therefore, the method has important practical significance for trichothecene compounds in grains, and furthermore, according to the embodiment of the invention, the sample to be detected is grains. The grains herein include grains and other raw materials, semi-finished products and finished products, namely grains and other raw materials, and processed products based on the grains and other raw materials, including grains, wheat flour, noodles, bread and the like.
S200 high performance liquid chromatography high resolution mass spectrometry detection
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 an embodiment of the present invention, the chromatographic conditions of the high performance liquid chromatography high resolution mass spectrum: chromatographic column: ZORBAX Eclipse Plus C 18 chromatographic columns; flow rate: 0.3mL/min.
According to an embodiment of the present invention, the chromatographic mobile phase of the high performance liquid chromatography high resolution mass spectrum is: mobile phase a was 0.1% acetic acid and 2mM aqueous ammonium acetate and mobile phase B was methanol.
According to the embodiment of the invention, the chromatographic elution of the high-resolution mass spectrum of the high-performance liquid chromatography is gradient elution. According to the embodiment of the invention, the elution condition of gradient elution is 0～2.0min,10％B;2.0～3.0min,10～20％B;3.0～7.0min,20～24％B;7.0～10.5min,24～30％B;10.5～13.5min,30～60％B;13.5～15.0min,60～70％B;15.0～18.0min,70～75％B;18.0～18.1min,75～100％B;18.1～21.0min,100％B;21.0～22.0min,100～10％B., so that the chromatographic separation effect is good, the subsequent mass spectrum detection is facilitated, and the detection accuracy and precision are high.
According to an embodiment of the present invention, the mass spectrometry conditions of the high performance liquid chromatography high resolution mass spectrometry: ion source: electrospray ion source esi+; scanning mode: full MS/dd-MS 2 scan mode; capillary voltage: 3.2kV; ion source temperature: 320 ℃. Therefore, under the conditions of the chromatograph and the mass spectrum, the peak shape obtained by detection is better, the separation of the compounds contained in the cereal grains is facilitated, the sensitivity and the stability of the detection are higher, and the retention time and the abundance ratio of the compounds are more accurate.
S300 analysis and processing
And judging whether the sample to be detected contains the trichothecene toxins and analogues thereof based on mass spectrum multi-feature structure fragment data in the detection result. Based on the multiple feature fragment scan, it is possible to accurately determine whether compounds in the cereal grain contain related parent structures that may lead to a risk of cereal grain food safety. Based on the scanning technology, not only the known trichothecene toxins but also the trichothecene toxins can be detected, and novel trichothecene toxin structural analogues can be detected, so that the detection accuracy is high, and the method can be effectively used for early warning of cereal food safety.
The term "analog" as used herein refers to compounds having a similarity in chemical structure, and in particular, in this document, "analog" refers to structural analogs of trichothecene toxins, including compounds having but not limited to a type a, type B trichothecene toxin parent structure, and in some embodiments, the use of these analogs can accurately determine whether a compound in a cereal contains a type a, type B trichothecene toxin parent structure that can result in a cereal food safety risk, thereby detecting a risk substance that is identical to the trichothecene toxin structure. According to an embodiment of the present invention, the trichothecene type toxin and the analogues thereof are at least one selected from the group consisting of trichothecene type toxin, i.e., diacetyl-falcarinol, neosolane falcarinol, T-2 toxin, HT-2 toxin, falcarinone, deoxynivalenol, 3-acetyldeoxynivalenol and 15-acetyldeoxynivalenol.
According to an embodiment of the present invention, it is determined whether a trichothecene toxin structural analog is present in a cereal grain based on the abundance ratio of multiple feature chips and multiple feature chips. That is, whether the compound in the cereal grain contains fragments with multiple characteristic structures is judged, if the compound in the cereal grain contains fragments with multiple characteristic structures, the abundance ratio of the mass spectrum marking fragment ions is judged, and if the abundance of the mass spectrum marking fragment ions is the same as that of the known compound and the mass accuracy is within 5ppm, the cereal grain contains trichothecene toxins.
According to an embodiment of the invention, whether a trichothecene structural analog is present in the cereal grain is determined based on multiple feature fragment ions in mass spectrometry data. Based on the multiple feature fragment scan, it is possible to accurately determine whether compounds in the cereal grain contain related parent structures that may lead to a risk of cereal grain food safety. The inventors speculate that the fragmentation structure of the same parent nucleus by analyzing the structure of various trichothecene toxins, according to embodiments of the present invention, fragments of the mass spectrum multiple signature structure are a type a trichothecene toxin compound of formula I and a type B trichothecene toxin compound of formula II,
Wherein R 1、R2、R3 and R 4 are each independently H, halogen, 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 sulfamoyl.
According to an embodiment of the invention, the mass spectral multi-feature fragment data includes mass-to-charge ratios and abundance ratios of multi-feature fragment ions. According to an embodiment of the invention, the mass to charge ratio of the multi-feature fragment ion 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 multi-feature fragment ions is not lower than 80%, and the mass precision is within 5ppm, so that the multi-feature fragment ion can be used as the multi-feature fragment of the structural compound. By detecting the fragment ions with at least one multi-characteristic structure, the parent nucleus structure of the trichothecene toxin compound is deduced, and whether the trichothecene toxin and the structural analogues thereof are contained or not is judged. By detecting the fragment ions of the two to three multi-characteristic structures, the parent nucleus structure of the A-type or B-type trichothecene type toxin compound is deduced. Mass-to-charge ratio
According to an embodiment of the present invention, the extraction process includes: mixing the sample to be tested with water, and adding 0.1% acetonitrile formate solution to obtain a mixture; subjecting the mixture to ultrasonic treatment; and standing the mixture subjected to 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 of the sample from wheat flour will be described herein as an example. According to one embodiment of the invention, 2g (to the nearest 0.01 g) of wheat flour sample is weighed into a 50mL centrifuge tube, 5mL of ultra-pure water is added, vortexed and allowed to stand. 10mL of 0.1% acetonitrile formate solution is added, vortex is carried out for 2min, ultrasonic extraction is carried out for 10min, then standing is carried out, 7mL of supernatant is taken and placed in a QuEChERS selective dispersion solid phase extraction kit. After vortexing for 5min at 4℃and centrifuging, 5mL of supernatant nitrogen was blown to dryness, 1mL of the reconstituted solution (mobile phase A/mobile phase B: 2/8) was reconstituted, and 2. Mu.L was taken for analysis by the UHPLC-Q-Orbitrap system, passing through a 0.22 μm organic film.
According to another aspect of the invention, there is provided a kit for detecting trichothecene toxins and analogues thereof. According to an embodiment of the invention, the kit comprises reagents, standards, auxiliary materials or combinations of at least one of the foregoing methods for detecting trichothecene toxins and analogues thereof.
According to an embodiment of the present invention, the trichothecene type toxin and the analogues thereof are at least one selected from the group consisting of trichothecene type toxin, i.e., diacetyl-falcarinol, neosolane falcarinol, T-2 toxin, HT-2 toxin, falcarinone, deoxynivalenol, 3-acetyldeoxynivalenol and 15-acetyldeoxynivalenol.
The invention will now be described 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 present invention will be explained below with reference to examples. It will be appreciated by those skilled in the art that the following examples are illustrative of the present invention and should not be construed as limiting the scope of the invention. The examples are not to be construed as limiting the specific techniques or conditions described in the literature in this field or as per the specifications of the product. The reagents or apparatus used are not manufacturer specific and are conventional products commercially available, for example, from Sigma company.
Example 1
The method provided by the embodiment of the invention is used for detecting the potential trichothecene toxins and analogues thereof in grains, and specifically comprises the following steps:
1. Raw materials and instruments
1.1 Standards, reagents and samples
Diacetyl ribine, neoeggplant disease fusarium enol, T-2 toxin, HT-2 toxin, fusarium enone, deoxynivalenol, 3-acetyl deoxynivalenol and 15-acetyl deoxynivalenol are all purchased from Australian Romer, and the concentration error of a standard substance is within 2%. The cereal grain sample is from freshly harvested cereal grain in a wheat farm. Formic acid and acetic acid were purchased from Thermo FISHER SCIENTIFIC, usa; chromatographic grade methanol and acetonitrile were purchased from Thermo FISHER SCIENTIFIC company, usa; chromatographic grade ammonium acetate was purchased from Sigma, usa; quEChERS selective dispersion solid phase extraction kit (4 g magnesium sulfate, 1g sodium chloride, 1g disodium citrate, 0.5g disodium citrate hydrate) and dispersion SPE kit (149.9mg PSA,149.9mg C 18 EC,900.2mg magnesium sulfate) were all purchased from America Agilent Technologies.
1.2 Sample pretreatment
The cereal grain sample was ground and mixed well, 2g (to the nearest 0.01 g) of the sample was weighed into a 50mL centrifuge tube, 5mL of ultra-pure water was added, vortexed and allowed to stand. 10mL of 0.1% acetonitrile formate solution is added, vortex is carried out for 2min, ultrasonic extraction is carried out for 10min, then standing is carried out, 7mL of supernatant is taken and placed in a QuEChERS selective dispersion solid phase extraction kit. After vortexing for 5min at 4℃and centrifuging, 5mL of supernatant nitrogen was blown to dryness, 1mL of the reconstituted solution (mobile phase A/mobile phase B: 2/8) was reconstituted, and 2. Mu.L was taken for analysis by the UHPLC-Q-Orbitrap system, passing through a 0.22 μm organic film.
1.3 Instruments
Analysis was performed using Thermo UltiMate 3000,3000 ultra high performance liquid chromatography orbitrap high resolution mass spectrometer Q-exactive. Chromatographic column ZORBAX Eclipse Plus C 18 chromatographic column (2.1 mm. Times.100 mm,1.8 μm) was used in the experiment.
2. Experimental conditions
2.1 High Performance liquid chromatography high resolution Mass Spectrometry data analysis
2.1.1 Liquid chromatography conditions: the chromatographic column is ZORBAX Eclipse Plus C 18 chromatographic column; mobile phase A was 0.1% acetic acid and 2mM ammonium acetate in water, mobile phase B was methanol, flow rate was 0.3mL/min; mobile phase gradient of ：0～2.0min,10％B;2.0～3.0min,10～20％B;3.0～7.0min,20～24％B;7.0～10.5min,24～30％B;10.5～13.5min,30～60％B;13.5～15.0min,60～70％B;15.0～18.0min,70～75％B;18.0～18.1min,75～100％B;18.1～21.0min,100％B;21.0～22.0min,100～10％B.
2.1.2 Mass Spectrometry conditions: electrospray ion source esi+; full MS/dd-MS 2 scan mode: capillary voltage 3.2kV; the ion source temperature was 320 ℃. Mass spectral parameters of 8 trichothecenes are shown in table 2:
TABLE 2
Conclusion and discussion 3
3.1 Studying the known trichothecene toxins according to the mass spectrum cleavage rules and screening out fragments with multiple characteristic structures
The method adopts high-resolution Mass spectrum combined with Mass front to analyze the structures of 8 known trichothecene toxins (diacetyl ribine, neosolane disease fusarium enol, T-2 toxin, HT-2 toxin, fusarium ketene, deoxynivalenol, 3-acetyldeoxynivalenol and 15-acetyldeoxynivalenol), and finds similar parent nucleus structures, so that the method has the same Mass spectrum cracking reaction, can be divided into A-type trichothecene toxins and B-type trichothecene toxins, adopts Venn diagram analysis to screen out fragments with multiple characteristic structures, has the abundance of more than 80 percent, has the Mass accuracy of less than 5ppm, and can be used as fragments with multiple characteristic structures of the compounds with the structures (see figure 2).
3.2 Establishing a multiple feature fragment scanning technique for detection of novel structural analogs in actual samples
Screening to obtain 4 groups of multiple characteristic structure fragments, so as to establish a multiple characteristic structure fragment scanning technology (see figure 3), and finding that the trichothecene toxin structural analogue exists in an actual sample by examining the consistency and the abundance consistency of the multiple characteristic structure fragments (see figure 4). Based on the mass spectrometry parent ion and mass spectrometry fragment information (see table 3), structural analogs of the risk species can be used to infer, as shown in particular in fig. 5.
TABLE 3 Table 3
In conclusion, the multi-characteristic structure fragment scanning technology established by utilizing the multi-characteristic structure fragments of the embodiment of the invention can be used for detecting whether the trichothecene and the structural analogues thereof exist in grains, so that the safety risk of novel grains and foods is further solved. The problems can be found timely, effectively and scientifically, the rapid, accurate and active targeted identification of the potential chemical risks of grains can be realized, the food safety risks are effectively reduced, and the breakthrough of the detection and analysis technology of the potential risk substances in grains is realized.
In the description of the present specification, a description referring to terms "one embodiment," "some embodiments," "examples," "specific examples," or "some examples," etc., means 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 present invention. In this specification, schematic representations of the above terms do not necessarily refer to the same embodiments or examples. 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 present invention have been shown and described, it will be understood by those of ordinary skill in the art that: many changes, modifications, substitutions and variations may be made to the embodiments without departing from the spirit and principles of the invention, the scope of which is defined by the claims and their equivalents.
Claims (2)
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;
performing 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 analogues thereof based on mass spectrum multi-feature structure fragment data in the detection result, wherein the abundance ratio of the multi-feature structure fragment ions is not less than 80%; wherein the structure of the A-type trichothecene type toxin compound is shown in a formula I, the structure of the B-type trichothecene type toxin compound is shown in a formula II,
Wherein R 1、R2、R3 and R 4 are each independently H, halogen, 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 sulfamoyl,
When the characteristic fragment mass-to-charge ratio is at least two of 247.1331, 229.1226, 217.1228, 199.1122 and 105.0705, then the sample to be tested is the trichothecene type a toxin compound and contains 3 substituents; when the characteristic fragment mass-to-charge ratio is at least two of 245.1174,227.1068, 215.1070, 197.0964 and 105.0705, then the sample to be tested is the trichothecene type a toxin compound and contains 4 substituents;
When at least two of the characteristic fragment mass to charge ratios 249.1100, 231.1019, 203.1075 and 137.0597, then the sample to be tested is the trichothecene type B toxin compound and contains 3 substituents; when the characteristic fragment mass-to-charge ratio is at least two of 247.0973, 229.0863, 201.0913 and 137.0602, then the sample to be tested is the trichothecene type B toxin compound and contains 4 substituents;
wherein, the mass spectrum condition of the high-resolution mass spectrum of the high-performance liquid chromatography:
ion source: electrospray ion source esi+;
Scanning mode: fullMS/dd-MS 2 scan mode;
capillary voltage: 3.2kV;
Ion source temperature: 320 c,
Wherein the sample to be measured is grain,
Wherein, the chromatographic conditions of the high-resolution mass spectrum of the high-performance liquid chromatography are as follows:
Chromatographic column: ZORBAX Eclipse Plus C 18 chromatographic columns;
flow rate: the concentration of the solution is 0.3mL/min,
Wherein, 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, mobile phase B was methanol,
Wherein the chromatographic elution of the high-resolution mass spectrum of the high-performance liquid chromatography is gradient elution,
Wherein the elution condition of the gradient elution is that 0～2.0min,10％B;2.0～3.0min,10～20％B;3.0～7.0min,20～24％B;7.0～10.5min,24～30％B;10.5～13.5min,30～60％B;13.5～15.0min,60～70％B;15.0～18.0min,70～75％B;18.0～18.1min,75～100％B;18.1～21.0min,100％B;21.0～22.0min,100～10％B.
2. The method according to claim 1, wherein the trichothecene and analog thereof is diacetyl-ributene, neosolane, T-2 toxin, HT-2 toxin, fusarenone, deoxynivalenol, 3-acetyldeoxynivalenol or 15-acetyldeoxynivalenol.
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