CN108226326A - Purposes and method of the tetrahydroquinoxaline derivative of o-phenylenediamine in terms of the adjacent dicarbonyl compound content of detection - Google Patents
Purposes and method of the tetrahydroquinoxaline derivative of o-phenylenediamine in terms of the adjacent dicarbonyl compound content of detection Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000001514 detection method Methods 0.000 title claims abstract description 14
- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical class C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 title claims abstract description 12
- -1 dicarbonyl compound Chemical group 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 32
- 238000001212 derivatisation Methods 0.000 claims abstract description 32
- 235000013305 food Nutrition 0.000 claims abstract description 31
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 12
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 claims description 11
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 11
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 11
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 9
- 239000013067 intermediate product Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 6
- 229940015043 glyoxal Drugs 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000010189 synthetic method Methods 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 3
- 238000005374 membrane filtration Methods 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims 1
- 238000009795 derivation Methods 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 abstract 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
- 150000002500 ions Chemical class 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 8
- 244000269722 Thea sinensis Species 0.000 description 7
- 238000011160 research Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 235000006468 Thea sinensis Nutrition 0.000 description 5
- 235000020279 black tea Nutrition 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000013580 millipore water Substances 0.000 description 4
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000006701 autoxidation reaction Methods 0.000 description 2
- 235000013405 beer Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 235000016213 coffee Nutrition 0.000 description 2
- 235000013353 coffee beverage Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- CIISBNCSMVCNIP-UHFFFAOYSA-N cyclopentane-1,2-dione Chemical class O=C1CCCC1=O CIISBNCSMVCNIP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000013616 tea Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 235000014101 wine Nutrition 0.000 description 2
- NMDWGEGFJUBKLB-YFKPBYRVSA-N (2S)-2-hydroxy-2-methyl-3-oxobutanoic acid Chemical compound CC(=O)[C@](C)(O)C(O)=O NMDWGEGFJUBKLB-YFKPBYRVSA-N 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000021245 dietary protein Nutrition 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 235000021393 food security Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 230000036252 glycation Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical class CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical group 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000013441 quality evaluation Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 235000020023 weizenbier Nutrition 0.000 description 1
- 235000015041 whisky Nutrition 0.000 description 1
- 235000020097 white wine Nutrition 0.000 description 1
- 235000020019 witbier Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
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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
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N30/14—Preparation by elimination of some components
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/067—Preparation by reaction, e.g. derivatising the sample
-
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N30/14—Preparation by elimination of some components
- G01N2030/146—Preparation by elimination of some components using membranes
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- 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)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention proposes purposes and method of the tetrahydroquinoxaline derivative of o-phenylenediamine in terms of the adjacent dicarbonyl compound content of detection, specifically with the tetrahydroquinoxaline derivative of o-phenylenediamine 4 (1,2,3,4 tetrahydrochysene, 6 quinoxalinyl) 1,2 o-phenylenediamines (I), 4 (1,2,3,4 tetrahydrochysenes 2,3 dimethyl, 6 quinoxalinyl) as derivatization reagent, the content of adjacent dicarbonyl compound (α DCs) in different foodstuff samples is detected using column front derivation HPLC methods 1,2 o-phenylenediamines (II) and the like III and IV etc..Compound I IV are used as the foundation that derivatization reagent measures the column front derivation HPLC methods of a variety of α DCs contents in different foodstuff samples for the first time.It is measured in food compared with the method for α DCs with existing column front derivation HPLC, there is the present invention derivative reaction mild condition to stablize, advantage simple and efficient to handle.
Description
Technical field
The present invention relates to a kind of reagents and its detection method for detecting adjacent dicarbonyl compound (α-DCs) content.
Background technology
Adjacent dicarbonyl compound (α-DCs), such as glyoxal (Gly), methyl-glyoxal (MGly), phenyl glyoxal
(PGly), diacetyl (DA), 2,3- pentanediones (PD), D-Glucose aldehyde ketone (2-KG), 1- deoxy-D-glucose aldehyde ketones (1-
DG), 3- deoxy-D-glucoses aldehyde ketone (3-DG), is the common catabolite that food is formed in process, chemical formula
It is specific as follows respectively：
In general, the sugar in food preparation process in food, as glucose and the free amine group in protein pass through first
Maillard reaction forms early stage glycation product, and then switchs to the α-DCs of high reaction activity；Meanwhile in the fermentation of some foods
In process and some biological processes, α-DCs can also be generated by lipid oxidation approach.Early period research shows that, these change
Close object be present in the food of numerous species, as fruit juice, tea, coffee, beer, soy sauce, milk, honey, some baby foods and
Grape wine etc..In general, the food containing relatively large carbohydrate, lipid or protein is more prone to α-DCs.On the one hand,
These α-DCs play a significant role in the organoleptic feature of food, such as their contents in various food can influence food
Flavor, taste, color etc., so as to determine the quality of food；And some α-DCs play the role of improving flavour of food products and color and luster,
Thus they can be used as food additives extensive use in food processing process.On the other hand, the presence of these compounds
The cross-linking reaction of food protein may be mediated, is damaged so as to cause nutritive value of food.Therefore, the α-DCs in food
Content, the content of particularly Gly and MGly, in western countries as the Toxicological Characterization parameter of glucose toxin and
As a kind of index of food security quality evaluation.Existing research is also it has been proved that there are some effective mechanism in human body
To be metabolized these carbonyls, but when taking in such excessive compound from exogenous diet, human body just can not be by it
Thoroughly remove, remaining α-DCs will be accumulated in each tissue of human body, by with protein-interactings various in tissue
And albumen is caused to lose activity, so as to generate pathological effect to body, lead to the generation of various disease.In fact pharmacology
Research is learned it has been shown that α-DCs are related with many chronic diseases and age-related disease, as chronic complicating diseases of diabetes,
Angiocardiopathy, A Cihaimo diseases, Parkinson's disease and aging etc..Therefore, the quality control based on food and protection people
Class health establishes effectively practical detection means and is of great significance come the α-DCs quantified in various food.
The existing method for measuring α-DCs is mostly column front derivation-high performance liquid chromatography (HPLC), this mainly due to
α-DCs are compounds that is a kind of highly water soluble and lacking chromophore, are directly detected not only pretreatment process complexity and method
Sensitivity it is also satisfactory not to the utmost, and introduce some bases with UV absorption or fluorescence by being derived to them
Group, it is possible to improve their detectability, and increase the sensitivity of detection.In existing column front derivation-HPLC methods usually
The derivatization reagent used is o-phenylenediamine, its derivative and the like, and the major defect of these derivatization reagents is to spread out
Raw reaction needs to carry out under conditions of more harsh, and such as nearly all existing derivatization process is required for heating to promote
Reaction process, and the autoxidation that may enhance α-DCs precursor substances in sample is heated, α-DCs concentration is caused to increase, so as to
Influence the accuracy measured.In addition, research also shows in derivatization reagent, and in the presence of o-phenylenediamine, long-time heating sample
The autoxidation approach of glucose can be changed, and then influence α-DCs actual contents in sample, so that measurement result is completely not
Reliably.Although reaction can also carry out at room temperature when also some researches show that using o-phenylenediamine as derivatization reagent, shortcoming is anti-
It could be completed in requisition for a few hours, this can not only so that continuous mode is tediously long, but also can cause to certain α-DCs, especially DA
Measure it is inaccurate because in prolonged reaction process, the precursor compound acetolactic acid of DA can be because of non-enzymatic oxidation mistake
Journey and be converted into DA.Therefore it needs to develop new α-DCs derivatization reagents, to realize (the short time at room temperature in a mild condition
Interior completion derivative reaction) α-DCs in the various food samples of Accurate Determining.
In the research of early period, applicant is utilized respectively 3,3 '-diaminobenzidine (DAB) and its derivative 4- (2,3-
Dimethyl -6- quinoxalinyls) -1,2- o-phenylenediamines (DQB) are pre-column derivatization reagent, it establishes and measures in white wine and beer
HPLC method (the articles of DA：Wang Xinjie etc., chromatography, 2017,35,837；Ji-Yu Wang etc., J.Agric.Food Chem.,
2017,65,2635；Patent application：Gao Wenyun etc., application for a patent for invention number：201610497512.2).These methods it is main
Advantage is that column front derivation process condition is mild, be can be completed in 10 minutes at room temperature.But both compounds are as derivatization
Reagent it is each have by oneself oneself the shortcomings that：Compound DAB since its structure includes two groups of ortho-diaminobenzene structural units, so
Product is more complicated when it is reacted with the mixture of a variety of α-DCs, therefore is only capable of surveying single α-DC compounds respectively
It is fixed, and a variety of α-DCs ingredients can not measure simultaneously.Although compound DQB and the like overcomes compound DAB
Disadvantages mentioned above, but due to wherein contain quinoxaline structural unit so that its it is stronger acid or alkaline condition (pH<2 or>
10) it is unstable under；Meanwhile DQB and the like sensitivity when being detected to certain α-DCs is relatively low, such as 2-KG, 1-DG
And 3-DG etc., these shortcomings limit them as derivatization reagent and measure at the same time in terms of a variety of α-DCs should
With.
Invention content
Present invention research is used to detect the suitable pre-column derivatization of a variety of adjacent dicarbonyl compound (α-DCs) contents simultaneously
Reagent measures sensitive quick, the reliable and stable method of α-DCs contents in various food with HPLC methods.
Present invention determine that scheme it is as follows：
Using the tetrahydroquinoxaline derivative of o-phenylenediamine as derivatization reagent, using the detection of column front derivation-HPLC methods not
With the content of α-DCs a variety of in food.Reaction principle is following (by taking compound I/II as an example)：
The tetrahydroquinoxaline derivative of above-mentioned o-phenylenediamine is preferred：4- (1,2,3,4- tetrahydrochysene -6- quinoxalinyls) -1,2- is adjacent
Phenylenediamine (I), 4- (1,2,3,4- tetrahydrochysene -2,3- dimethyl -6- quinoxalinyls) -1,2- o-phenylenediamines (II) and their class
Like object III, IV, structure is as follows：
Above-mentioned 4- (1,2,3,4- tetrahydrochysene -6- quinoxalinyls) -1,2- o-phenylenediamines (I), 4- (1,2,3,4- tetrahydrochysenes -2,3-
Dimethyl -6- quinoxalinyls) -1,2- o-phenylenediamines (II) synthetic method：The 3,3'-diaminobenzidine of 1.0mmol
(DAB) intermediate production can be obtained by being reacted at room temperature in water with the adjacent dione compounds glyoxal or diacetyl of 0.3mmol
Object, the intermediate product obtain target product with lithium aluminium hydride (LiAlH4) reduction；Reaction equation is as follows：
The synthetic method of above-mentioned analog III, IV：The 3,3'-diaminobenzidine (DAB) and 0.3mmol of 1.0mmol
Ring neighbour dione compounds 1, reaction obtains intermediate product at room temperature in methyl alcohol for 2- cyclopentanediones or 1,2- cyclohexanedione,
The intermediate product is with lithium aluminium hydride (LiAlH4) reduction obtains target product, reaction equation is as follows：
The tetrahydroquinoxaline derivative of above-mentioned o-phenylenediamine detects the side of the content of α-DCs in food as derivatization reagent
Method includes the following steps：
20%~50% methanol solution 0.5mL of the tetrahydroquinoxaline derivative of the o-phenylenediamine of (1) 0.1~1mM is added in
It was 7.0-10.0 that pH is adjusted in 1.5 mL samples to be tested, after mixing, in room temperature reaction 30~60 minutes；
(2) with 0.22 μm of membrane filtration, filtrate is detected the sample that reaction is completed with HPLC.
Wherein, the HPLC best configurations that step (2) carries out are as follows：
Chromatographic column：Shim-Pack VP-ODS C18 columns；Mobile phase：Methanol-water gradient elution, 0min, 60% (volume
Score) methanol；10min：100% methanol；15min：60% (volume fraction) methanol；17min：60% (volume fraction) methanol；
Column temperature：Room temperature；Sample size：20~100 μ L；0.7~1.5mL/min of flow velocity；Detection wavelength：254nm.
The present invention has following technique effect：
New derivatization reagent, i.e. 4- (1,2,3,4- tetrahydrochysene -6- quinoxalinyls) -1,2- o-phenylenediamines (I), 4- (1,2,
3,4- tetrahydrochysene -2,3- dimethyl -6- quinoxalinyls) -1,2- o-phenylenediamines (II) and the like III-IV, using they as
Derivatization reagent is applied to measure while a variety of α-DCs in various food, and derivative reaction mildly (is reacted in pH7.0-9.0
And carry out 30 min at room temperature and can carry out completely), operation facility, HPLC measurement results are accurately and reliably.
Description of the drawings
Fig. 1 is compound 4- (1,2,3,4- tetrahydrochysene -6- quinoxalinyls) -1,2- o-phenylenediamines (I) as derivatization reagent
HPLC chromatogram when being measured.
Wherein：A. the HPLC chromatogram of compound I；B. the HPLC chromatic graphs spectrum of not derivative black tea extract；C. compound I
Measure α-DCs HPLC chromatogram (α-DCs include 2-KG (a), 3-DG (b), 1-Gly (c), 2-MGly (d), 3-DA (e) and
4-PD(f))；D. compound I measures α-DCs contents (non-mark-on) in black tea；E. compound I measures α-DCs contents in black tea
(after mark-on).
Fig. 2 measures α-DCs working curves for compound I and II.
Wherein：Dotted line：I is the working curve of each compound when derivatization reagent measures；Solid line：II is surveyed for derivatization reagent
The periodically working curve of each compound.
Fig. 3 makees for compound 4- (1,2,3,4- tetrahydrochysene -2,3- dimethyl -6- quinoxalinyls) -1,2- o-phenylenediamines (II)
HPLC chromatogram when being measured for derivatization reagent.
Wherein：A. the HPLC chromatogram of compound II；B. compound II measures the HPLC chromatogram (α-DCs packets of α-DCs
Include 2-KG (a), 3-DG (b), 1-Gly (c), 2-MGly (d), 3-DA (e) and 4-PD (f))；C. do not derive black tea extract
HPLC chromatic graphs are composed；D. (chromatography 1 is the black tea sample of non-mark-on to α-DCs contents, and chromatography 2 is mark-on in compound II measure black tea
Black tea sample afterwards).
Specific embodiment
First, the preparation of derivatization reagent：
1st, the synthesis of compound I and II：
3,3'-diaminobenzidine (DAB) (1.0mmol) and adjacent dione compounds glyoxal or diacetyl (0.3mmol)
Reaction can obtain intermediate product at room temperature in water, and the product is with lithium aluminium hydride (LiAlH4) or reduction can obtain mesh
Mark molecule I and II.Reaction equation is as follows：
Detailed process is：
1) preparation of I-a/II-a：Weigh 3,3'- diaminobenzidines, four hydrochloride (DAB-4HCl) (108mg,
0.3mmol), it is added in 25mL round-bottomed flasks, adds in 10mL distilled water, gentle agitation makes DAB fully dissolve at room temperature.Greatly
After about 10-20 minutes, glyoxal (24mg, 0.4mmol) or diacetyl (35mg, 0.4mmol) are added in, continues to stir at room temperature
After half an hour, reaction solution is filtered, insoluble matter three times (5mL × 3), is obtained cleaning solution and closed with filtrate before with distillation washing
And chloroform extraction (20mL × 5), merge the 3rd time to the 5th extract liquor, anhydrous MgSO4After 2 hours dry, cross and filter out
Drier is removed, filtrate is target compound (I-a through being concentrated under reduced pressure to give dark red powder：63.5mg 86.1%； II-a：
65.2mg, 82.3%).
I-a：1H-NMR(CD3OD, 400MHz)：8.41 (2H, d, J=6), 8.11 (1H, s), 7.99 (2H, m), 7.26
(1H, s), 7.18 (1H, d, J=6), 6.95 (1H, d, J=6).HRESI-MS (positive ion mode) m/z：Calculated value
237.1140, measured value：237.1151[M+H]+。
II-a：1H-NMR(CD3OD, 400MHz)：8.04 (1H, s), 7.94 (2H, m), 7.19 (1H, brs), 7.08 (1H,
D, J=6), 6.81 (1H, d, J=6), 2.78 (3H, s, Me), 2.73 (3H, s, Me).ESI-MS (positive ion mode) m/z：Meter
Calculation value 265.1453, measured value：265.1439[M+H]+。
2) preparation of I/II：LiAlH is added in drying and being full of in the 10mL round-bottomed flasks of nitrogen4(38mg,
1.0mmol), 5mL dries acetonitrile and compound I-a (24mg, 0.1mmol) or II-a (27mg, 0.1mmol), under nitrogen protection
After room temperature reaction 1 hour, bubble-free generation is slowly added dropwise in methanol to system again, and reaction mixture is transferred in centrifuge tube simultaneously
It in 4 DEG C, is centrifuged 10 minutes under 6000rpm, supernatant is transferred in round-bottomed flask, and solid content is cleaned with the methanol of 5mL × 2, after centrifugation
Merge supernatant, it is target compound (I that vacuum distillation, which removes solvent and obtains dark red powder,：21.3mg 88.1%；II：
22.5mg, 83.9%).
I：1H-NMR(CD3OD, 400MHz)：7.13 (2H, d, J=6), 6.94 (2H, brs), 6.69 (2H, d, J=6),
3.31 (4H, t, J=7).HRESI-MS (positive ion mode) m/z：Calculated value 241.1453, measured value： 241.1451[M+H
]+。
II：1H-NMR(CD3OD, 400MHz)：6.93 (2H, d, J=6), 6.84 (2H, brs), 6.59 (2H, d, J=6),
3.08 (2H, m), 1.43 (6H, d, J=8).ESI-MS (positive ion mode) m/z：Calculated value 269.1766, measured value：
269.1759[M+H]+。
2nd, the synthesis of compound III and IV：3,3'-diaminobenzidine (DAB) (1.0mmol) and ring neighbour's diketone chemical combination
Reaction can obtain intermediate product at room temperature in methyl alcohol for object 1,2- cyclopentanediones or 1,2- cyclohexanedione (0.3mmol), should
Product is with lithium aluminium hydride (LiAlH4) reduction can obtain target molecule III and IV.Reaction equation is as follows：
Detailed process is：
1) preparation of III-a/IV-a：Weigh 3,3'- diaminobenzidines, four hydrochloride (DAB-4HCl) (108mg,
0.3mmol), it is added in 25mL round-bottomed flasks, addition 8mL distilled water, 2mL methanol, gentle agitation makes DAB abundant at room temperature
Dissolving.After about 10-20 minutes, add in 1,2- cyclopentanediones (40mg, 0.4mmol) or 1,2- cyclohexanedione (45mg,
0.4mmol), continue at room temperature after stirring half an hour, reaction solution is filtered, insoluble matter three times (5mL × 3), is obtained with distillation washing
Merge to cleaning solution with filtrate before, chloroform extraction (20mL × 5), merge the 3rd time to the 5th extract liquor, it is anhydrous
MgSO4After 2 hours dry, drier is filtered to remove, filtrate is target compound through being concentrated under reduced pressure to give dark red powder
(III-a：53.9mg 65.1%；IV-a：65.4mg, 75.2%).
III-a：1H-NMR(CD3OD, 400MHz)：8.01 (1H, s), 7.80 (2H, m), 7.30 (1H, s), 7.14 (1H,
D, J=6), 6.91 (1H, d, J=6), 2.15 (4H, t, J=8), 1.49 (2H, m).HRESI-MS (positive ion mode) m/z：
Calculated value 277.1453, measured value：277.1441[M+H]+。
IV-a：1H-NMR(CD3OD, 400MHz)：8.02 (1H, s), 7.91 (2H, m), 7.11 (1H, brs), 7.03 (1H,
D, J=6), 6.73 (1H, d, J=6), 2.31 (4H, t, J=8), 1.61 (4H, m).ESI-MS (positive ion mode) m/z：Meter
Calculation value 291.1610, measured value：291.1629[M+H]+。
2) preparation of III/IV：LiAlH is added in drying and being full of in the 10mL round-bottomed flasks of nitrogen4(38mg,
1.0mmol), 5mL dries acetonitrile and compound III-a (28mg, 0.1mmol) or IV-a (29mg, 0.1mmol), nitrogen protection
Under after room temperature reaction 1 hour, bubble-free generation is slowly added dropwise in methanol to system again, reaction mixture is transferred in centrifuge tube
And in 4 DEG C, centrifuged 10 minutes under 6000rpm, supernatant is transferred in round-bottomed flask, and solid content is cleaned with the methanol of 5mL × 2, centrifugation
After merge supernatant, it is target compound (III that vacuum distillation, which removes solvent and obtains dark red powder,：23.3mg 84.1%；
IV：24.1mg, 83.1%).
III：1H-NMR(CD3OD, 400MHz)：8.07 (1H, s), 7.89 (2H, m), 7.32 (1H, s), 7.21 (1H, d, J
=6), 6.99 (1H, d, J=6), 2.65 (2H, m) 1.65 (4H, m), 1.49 (2H, m).HRESI-MS (positive ion mode) m/
z：Calculated value 281.1766, measured value：281.1751[M+H]+。
IV：1H-NMR(CD3OD, 400MHz)：8.02 (1H, s), 7.91 (2H, m), 7.11 (1H, brs), 7.03 (1H, d,
J=6), 6.73 (1H, d, J=6), 2.71 (2H, m), 1.61 (4H, m), 1.41 (4H, m).ESI-MS (positive ion mode) m/
z：Calculated value 295.1923, measured value：295.1919[M+H]+。
2nd, compound I-IV measures α-DCs (standards in different food products as derivatization reagent with column front derivation-HPLC methods
Addition method)
In view of compound III, IV is the analog of compound I and II, property and application effect are expectable with compound I
And II is similar, therefore, below mainly using compound I and II as derivatization reagent for：
1st, different food products sample pre-treatments：Soda and beer sample (respectively taking 10.0mL), at room temperature ultrasound degassing
10min is preserved before analysis at 4 DEG C；Coffee (1.0g) adds in 8.0mL boiling water and is placed in 20min at 85 DEG C, it is made fully to dissolve,
10.0mL is diluted to Millipore water after its cooling, is preserved at 4 DEG C before analysis；Tea (1.0g) adds in 8.0 mL boiling water simultaneously
25min at 80 DEG C is placed in, is fully dissolved out ingredient in tealeaves, 10.0mL is diluted to Millipore water after its cooling, it will
Supernatant is preserved at 4 DEG C before the analysis；After yoghurt example shakes up, 10.0mL is taken to add in the abundant mixing of 2mL methanol, by mixture
To centrifuge 30min at 8000rpm, 4 DEG C, supernatant (about 1.5mL) is diluted to 2.0mL with Millipore water, before analysis at 4 DEG C
It preserves.Remaining foodstuff samples such as whiskey, fruit beverage and grape wine, without specially treated.
2nd, compound I detects α-DCs contents in food samples as derivatization reagent：By the foodstuff samples of pretreatment
(0.67 mL) is added in the methanol solution (5mM) of the II of 0.05mL, adds 0.08mL Millipore water and 0.20mL first
Alcohol, after abundant mixing, the pH for adjusting mixture is 8.0, is reacted at room temperature 30 minutes.In mark-on experiment, by each foodstuff samples point
It Jia Ru not four standard solution：Gly (0.5,1.0 and 5.0 μM), MGly (0.5,1.0 and 5.0 μM), DA (0.5,1.0 and 5.0 μ
M) and PD (0.5,1.0 and 5.0 μM), after the abundant mixing of vortex mixer, it is 8.0 to adjust pH of mixed, room temperature reaction 30
Minute.Reaction solution (non-mark-on is accurate and adds standard) is respectively with 0.22 μm of membrane filtration, and filtrate is detected with HPLC, with derivative
Peak area carry out quantitative analysis.Chromatographic condition is：Chromatographic column, Shim-Pack VP-ODS C18 columns (250 × 4.6mm, 5 μ
m)；Mobile phase, methanol-water gradient elution, 0min, 60% methanol；10min：100% methanol；15min：60% methanol；
17min：60% methanol；Column temperature, room temperature；Sample size, 20 μ L；0.7 mL/min of flow velocity；Detection wavelength, 254nm.HPLC chromatogram
And each compound working curve is shown in Fig. 1 and Fig. 2 respectively；LC-MS measurement results are shown in Table one.
3rd, compound II detects α-DCs contents in food samples as derivatization reagent：Continuous mode with compound I with being made
It is consistent that α-DCs content processes in food samples are detected for derivatization reagent.HPLC chromatogram and each compound working curve difference
See Fig. 2 and Fig. 3；LC-MS measurement results are shown in Table two.
Various α-DCs content detection results are specifically shown in Table three in different food products.
Table one, when being measured using compound I as derivatization reagent gained derivative LC-MS identifications
aThe ESI-MS data of each derivative are acquired from positive ion mode；bThe structure of each derivative is shown in aforementioned " background technology ".
Table two, when being measured using compound II as derivatization reagent gained derivative LC-MS identificationsa
aThe ESI-MS data of each derivative are acquired from positive ion mode；bThe structure of each derivative is shown in aforementioned " background technology ".
Various α-DCs content detection results in table three, different food products
* it is measured using compound I as derivatization reagent；* is measured using compound II as derivatization reagent；
aDuring fluid sample testing concentration unit for μM, be μ g/g during solid sample；bOpposite mark during six parallel determinations
Quasi- deviation；cIt is not detected；dTesting concentration is higher than detection limit but less than quantitative limit.
Claims (6)
1. the tetrahydroquinoxaline derivative of o-phenylenediamine is detected in column front derivation-HPLC methods in food as derivatization reagent
Adjacent dicarbonyl compound (α-DCs) content purposes.
2. purposes according to claim 1, it is characterised in that：The tetrahydroquinoxaline derivative of the o-phenylenediamine includes：
4- (1,2,3,4- tetrahydrochysene -6- quinoxalinyls) -1,2- o-phenylenediamines (I), 4- (1,2,3,4- tetrahydrochysene -2,3- dimethyl -6- quinolines
Quinoline base) -1,2- o-phenylenediamines (II) and their analog III, IV, structure it is as follows：
4- described in claim 2 3. (1,2,3,4- tetrahydrochysene -6- quinoxalinyls) -1,2- o-phenylenediamines (I), 4- (1,2,3,4-
Tetrahydrochysene -2,3- dimethyl -6- quinoxalinyls) -1,2- o-phenylenediamines (II) synthetic method, it is characterised in that：
The 3,3'-diaminobenzidine (DAB) of 1.0mmol is with the adjacent dione compounds glyoxal of 0.3mmol or diacetyl in water
In at room temperature reaction can obtain intermediate product, the intermediate product with lithium aluminium hydride (LiAlH4) reduction i.e. obtain target produce
Object；Reaction equation is as follows：
4. the synthetic method of analog III, IV described in claim 2, it is characterised in that：
The 3,3'-diaminobenzidine (DAB) of 1.0mmol and the ring neighbour dione compounds 1,2- cyclopentanediones or 1 of 0.3mmol,
Reaction obtains intermediate product to 2- cyclohexanediones at room temperature in methyl alcohol, and the intermediate product is with lithium aluminium hydride (LiAlH4) reduction
Target product is obtained, reaction equation is as follows：
5. using o-phenylenediamine described in claim 2 tetrahydroquinoxaline derivative as α in derivatization reagent detection food-
The method of the content of DCs, includes the following steps：
20%~50% methanol solution 0.5mL of the tetrahydroquinoxaline derivative of the o-phenylenediamine of (1) 0.1~1mM is added in
It was 7.0-10.0 that pH is adjusted in 1.5mL samples to be tested, after mixing, in room temperature reaction 30~60 minutes；
(2) with 0.22 μm of membrane filtration, filtrate is detected the sample that reaction is completed with HPLC.
6. according to the method described in claim 5, it is characterized in that：The HPLC that step (2) carries out is as follows：
Chromatographic column：Shim-Pack VP-ODS C18 columns；Mobile phase：Methanol-water gradient elution, 0min, 60% (volume fraction)
Methanol；10min：100% methanol；15min：60% (volume fraction) methanol；17min：60% (volume fraction) methanol；Column temperature：
Room temperature；Sample size：20~100 μ L；0.7~1.5mL/min of flow velocity；Detection wavelength：254nm.
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