CN110531007A - A kind of quasi-arachidonic acid substance detection method - Google Patents
A kind of quasi-arachidonic acid substance detection method Download PDFInfo
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- CN110531007A CN110531007A CN201910999577.0A CN201910999577A CN110531007A CN 110531007 A CN110531007 A CN 110531007A CN 201910999577 A CN201910999577 A CN 201910999577A CN 110531007 A CN110531007 A CN 110531007A
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- arachidonic acid
- acid substance
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- 238000001514 detection method Methods 0.000 title claims abstract description 44
- 239000000126 substance Substances 0.000 title claims abstract description 37
- 229940114079 arachidonic acid Drugs 0.000 title claims abstract description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012074 organic phase Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000012071 phase Substances 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000005119 centrifugation Methods 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical compound CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 12
- 238000003908 quality control method Methods 0.000 claims description 12
- ZTNANFDSJRRZRJ-UHFFFAOYSA-N 2,4-dimethylquinoline Chemical compound C1=CC=CC2=NC(C)=CC(C)=C21 ZTNANFDSJRRZRJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- CVZZNRXMDCOHBG-UHFFFAOYSA-N 2-azaniumyl-3-(2-chlorophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=CC=C1Cl CVZZNRXMDCOHBG-UHFFFAOYSA-N 0.000 claims description 6
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 claims description 6
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- PJSFRIWCGOHTNF-UHFFFAOYSA-N Sulphormetoxin Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC PJSFRIWCGOHTNF-UHFFFAOYSA-N 0.000 claims description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 6
- SRLROPAFMUDDRC-INIZCTEOSA-N ethyl N-benzoyl-L-tyrosinate Chemical compound C([C@@H](C(=O)OCC)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 SRLROPAFMUDDRC-INIZCTEOSA-N 0.000 claims description 6
- 229930003949 flavanone Natural products 0.000 claims description 6
- 150000002208 flavanones Chemical class 0.000 claims description 6
- 235000011981 flavanones Nutrition 0.000 claims description 6
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims description 6
- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical class COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 claims description 6
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 6
- 229960000282 metronidazole Drugs 0.000 claims description 6
- 229960004673 sulfadoxine Drugs 0.000 claims description 6
- 125000005425 toluyl group Chemical group 0.000 claims description 6
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims description 5
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 claims description 5
- 229960003720 enoxolone Drugs 0.000 claims description 5
- WNIFXKPDILJURQ-UHFFFAOYSA-N stearyl glycyrrhizinate Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=O)OCCCCCCCCCCCCCCCCCC)(C)CC5C4=CC(=O)C3C21C WNIFXKPDILJURQ-UHFFFAOYSA-N 0.000 claims description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 230000014759 maintenance of location Effects 0.000 claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 2
- 229960002449 glycine Drugs 0.000 claims description 2
- RDRCCJPEJDWSRJ-UHFFFAOYSA-N pyridine;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CC=NC=C1 RDRCCJPEJDWSRJ-UHFFFAOYSA-N 0.000 claims description 2
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 claims 1
- -1 4,4 '-methylene Chemical group 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 1
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- 150000002500 ions Chemical class 0.000 abstract description 6
- 238000000605 extraction Methods 0.000 abstract description 4
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- 239000012535 impurity Substances 0.000 abstract 1
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 4
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- 150000001875 compounds Chemical class 0.000 description 3
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 102000003820 Lipoxygenases Human genes 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 2
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 2
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- SWTYBBUBEPPYCX-VIIQGJSXSA-N (4Z,7Z,10Z,13Z,15E,19Z)-17-hydroxydocosahexaenoic acid Chemical compound CC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O SWTYBBUBEPPYCX-VIIQGJSXSA-N 0.000 description 1
- OZXAIGIRPOOJTI-XJAVJPOHSA-N (4Z,8E,10Z,13Z,16Z,19Z)-7-hydroxydocosahexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)C\C=C/CCC(O)=O OZXAIGIRPOOJTI-XJAVJPOHSA-N 0.000 description 1
- UVZBUUTTYHTDRR-WAQVJNLQSA-N (5S,6S)-dihydroxy-(7E,9E,11Z,14Z)-icosatetraenoic acid Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H](O)[C@@H](O)CCCC(O)=O UVZBUUTTYHTDRR-WAQVJNLQSA-N 0.000 description 1
- XEBKSQSGNGRGDW-CJWPDFJNSA-N (z,9s,10s)-9,10-dihydroxyoctadec-12-enoic acid Chemical compound CCCCC\C=C/C[C@H](O)[C@@H](O)CCCCCCCC(O)=O XEBKSQSGNGRGDW-CJWPDFJNSA-N 0.000 description 1
- KLLGGGQNRTVBSU-JDTPQGGVSA-N 13-HOTrE Chemical compound CC\C=C/CC(O)\C=C\C=C/CCCCCCCC(O)=O KLLGGGQNRTVBSU-JDTPQGGVSA-N 0.000 description 1
- JSFATNQSLKRBCI-VAEKSGALSA-N 15-HETE Natural products CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O JSFATNQSLKRBCI-VAEKSGALSA-N 0.000 description 1
- JSFATNQSLKRBCI-UHFFFAOYSA-N 15-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O JSFATNQSLKRBCI-UHFFFAOYSA-N 0.000 description 1
- JEKNPVYFNMZRJG-UFINWASNSA-N 16-HETE Chemical compound CCCCC(O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JEKNPVYFNMZRJG-UFINWASNSA-N 0.000 description 1
- JQTSFVHRPKVILF-UHFFFAOYSA-N 2,3-dihydroxyicosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCC=CC=CC=CC(O)=C(O)C(O)=O JQTSFVHRPKVILF-UHFFFAOYSA-N 0.000 description 1
- NNDIXBJHNLFJJP-UHFFFAOYSA-N 20-Hydroxyeicosatetraenoic acid Chemical compound OCCCCCC=CCC=CCC=CCC=CCCCC(O)=O NNDIXBJHNLFJJP-UHFFFAOYSA-N 0.000 description 1
- UXGXCGPWGSUMNI-BVHTXILBSA-N 5(S),15(S)-DiHETE Chemical compound CCCCC[C@H](O)\C=C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O UXGXCGPWGSUMNI-BVHTXILBSA-N 0.000 description 1
- GFNYAPAJUNPMGH-QNEBEIHSSA-N 5,6-DHET Chemical compound CCCCC\C=C/C\C=C/C\C=C/CC(O)C(O)CCCC(O)=O GFNYAPAJUNPMGH-QNEBEIHSSA-N 0.000 description 1
- FTAGQROYQYQRHF-FCWZHQICSA-N 5-HEPE Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C=C/C(O)CCCC(O)=O FTAGQROYQYQRHF-FCWZHQICSA-N 0.000 description 1
- FTAGQROYQYQRHF-OTZRFASISA-N 5-HEPE Natural products CCC=C/CC=C/CC=C/CC=C/C=C/C(O)CCCC(=O)O FTAGQROYQYQRHF-OTZRFASISA-N 0.000 description 1
- LSADDRSUZRRBAN-SRMUOKRHSA-N 5-HETrE Chemical compound CCCCCCCC\C=C/C\C=C/C=C/C(O)CCCC(O)=O LSADDRSUZRRBAN-SRMUOKRHSA-N 0.000 description 1
- MEASLHGILYBXFO-XTDASVJISA-N 5-oxo-ETE Chemical compound CCCCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCC(O)=O MEASLHGILYBXFO-XTDASVJISA-N 0.000 description 1
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- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 241001553178 Arachis glabrata Species 0.000 description 1
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- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 description 1
- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 description 1
- 101000579123 Homo sapiens Phosphoglycerate kinase 1 Proteins 0.000 description 1
- NMYRFHZXATXHDG-UHFFFAOYSA-N NC=1NC=CC1.N1=CC=CC=C1 Chemical compound NC=1NC=CC1.N1=CC=CC=C1 NMYRFHZXATXHDG-UHFFFAOYSA-N 0.000 description 1
- KJWZYMMLVHIVSU-IYCNHOCDSA-N PGK1 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](CCCCCCC(O)=O)C(=O)CC1=O KJWZYMMLVHIVSU-IYCNHOCDSA-N 0.000 description 1
- 102100028251 Phosphoglycerate kinase 1 Human genes 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- CBOMORHDRONZRN-QLOYDKTKSA-N prostaglandin E3 Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O CBOMORHDRONZRN-QLOYDKTKSA-N 0.000 description 1
- UQOQENZZLBSFKO-POPPZSFYSA-N prostaglandin J2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O UQOQENZZLBSFKO-POPPZSFYSA-N 0.000 description 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- OIWTWACQMDFHJG-CCFUIAGSSA-N resolvin D1 Chemical compound CC\C=C/C[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)C\C=C/CCC(O)=O OIWTWACQMDFHJG-CCFUIAGSSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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
-
- 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
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
- G01N30/7233—Mass spectrometers interfaced to liquid or supercritical fluid chromatograph
-
- 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
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
Landscapes
- 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)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention discloses a kind of quasi-arachidonic acid substance detection methods, including, with volume fraction, 300 parts of water containing 0.005%BHT are added in 100 parts of sample；500 parts of methyl tertiary butyl ether(MTBE) is added, upper organic phase is shifted in centrifugation, retains lower layer's water phase；500 parts of ethyl acetate is added into lower layer's water phase, centrifugation merges upper organic phase with the upper organic phase that previous step obtains；By combined upper organic phase with after being dried with nitrogen, acetonitrile-aqueous isopropanol is used to redissolve, upper machine testing.Internal standard that the present invention selects is stable, realize accurate detection under negative ions mode, interference will not be generated to the detection of quasi-arachidonic acid substance, detection is reproducible, impurity significantly reduces in detection method, and energy can substantially reduce the pollution to instrument, the method of the present invention is convenient and efficient, extraction time is short, detection signal-to-noise ratio is obviously improved, and sensitivity greatly improves.
Description
Technical field
The invention belongs to quasi-arachidonic acid substance detection technique fields, and in particular to a kind of quasi-arachidonic acid class object
Quality detection method.
Background technique
Cyclo-oxygenase (COX-2), the enzymatics such as lipoxygenase (LOX) and cytochrome P 450 enzymes are passed through by arachidonic acid
It is metabolized the hydroxyeicosatetraenoic acid (HETEs) generated, dihydroxy eicosatetraenoic acid (DiHETEs), epoxy Eicosatetraenoic
Sour (EETs), the metabolins such as prostaglandin (PGs) and thromboxane (TX) are the main composition eicosane of eicosane acid compounds
Acid, content of these endogenous arachic acid substances in biofluid and tissue are very low.
But it low to content in this substance there are pre-treatment preparation methods at high cost, very complicated, sample at present difficult examines
The problems such as survey.Therefore how to develop it is a kind of low cost, conveniently, can be improved detection sensitivity, lower detection noise method be
The prior art has technical problem to be solved.
Summary of the invention
The purpose of this section is to summarize some aspects of the embodiment of the present invention and briefly introduce some preferable implementations
Example.It may do a little simplified or be omitted to avoid our department is made in this section and the description of the application and the title of the invention
Point, the purpose of abstract of description and denomination of invention it is fuzzy, and this simplification or omit and cannot be used for limiting the scope of the invention.
In view of above-mentioned technological deficiency, the present invention is proposed.
Therefore, as one aspect of the present invention, the present invention overcomes the deficiencies in the prior art, provides a type
Arachidonic acid-type substance detecting method.
In order to solve the above technical problems, the present invention provides the following technical scheme that a kind of quasi-arachidonic acid substance is examined
Survey method comprising,
With volume fraction, 300 parts of water containing 0.005%BHT are added in 100 parts of sample；
500 parts of methyl tertiary butyl ether(MTBE) is added, upper organic phase is shifted in centrifugation, retains lower layer's water phase；
500 parts of ethyl acetate is added into lower layer's water phase, centrifugation obtains upper organic phase and previous step
Upper organic phase merges；
By combined upper organic phase with after being dried with nitrogen, acetonitrile-aqueous isopropanol is used to redissolve, upper machine testing.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: described to be added 500
The methyl tertiary butyl ether(MTBE) of part, centrifugation, 10000rpm is centrifuged 3min under the conditions of being included in 4 DEG C；500 are added into lower layer's water phase
The ethyl acetate of part, centrifugation, 10000rpm is centrifuged 3min under the conditions of being included in 4 DEG C.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: described to use second
Nitrile-aqueous isopropanol redissolves, wherein with volume basis, acetonitrile: isopropanol=1:1.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: the sample, packet
Include plasma sample.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: further including, by 2-
Chlorophenylalanine replaces solvent as internal standard, in the detection process, is reflected by 2- chlorophenylalanine peak area and retention time
The acquisition situation of actual sample.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: the 2- chlorobenzene third
Propylhomoserin concentration is 1 μ g/mL.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: further including, and uses
4,4 '-di-2-ethylhexylphosphine oxides (2- chloroaniline), P-anisidine, l-tyrosine methyl esters, 3- chloroaniline, 2,4- dimethyl quinoline, sulfanilamide (SN) pyrrole
Pyridine, Atrazine, sulfadoxine, DL-leucine, N- benzoyl-l-tyrosine ethyl ester, 6- phenyl -2- deracil, N-
(toluoyl) glycine, Metronidazole, enoxolone, flavanones, 6-caprolactone, 2-aminopyridine
Mixed sample as quality-control product, detection is at least into two needle quality-control products every time, according to spectrogram overlapping cases analysis and detecting instrument
State.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: by quality ratio,
Described 4,4 '-di-2-ethylhexylphosphine oxides (2- chloroaniline): P-anisidine: l-tyrosine methyl esters: 3- chloroaniline: 2,4- dimethyl quinolines: sulphur
Amine pyridine: Atrazine: sulfadoxine: DL-leucine: N- benzoyl-l-tyrosine ethyl ester: 6- phenyl -2- deracil:
N- (toluoyl) glycine: Metronidazole: enoxolone: flavanones: 6-caprolactone: 2- amino pyrrole
Pyridine=1:0.5:0.5:2:1:0.4:0.1:0.1:0.2:0.5:0.5:1:1:0.1:0.5:2:0.2.
A kind of preferred embodiment as quasi-arachidonic acid substance detection method of the present invention: described 4,4 '-is sub-
The concentration of methyl bis- (2- chloroanilines) is 1 μ g/mL, the concentration of P-anisidine is 0.5 μ g/mL, the concentration of l-tyrosine methyl esters is
0.5 μ g/mL, 3- chloroaniline concentration be 2 μ g/mL, 2,4- dimethyl quinoline concentration be 1 μ g/mL, the concentration of sulfapryidine is
0.4 μ g/mL, Atrazine concentration be 0.1 μ g/mL, the concentration of sulfadoxine is 0.1 μ g/mL, the concentration of DL-leucine is
0.2 μ g/mL, N- benzoyl-l-tyrosine ethyl ester concentration are 0.5 μ g/mL, the concentration of 6- phenyl -2- deracil is 0.5
μ g/mL, N- (toluoyl) glycine concentration be 1 μ g/mL, the concentration of Metronidazole is 1 μ g/
ML, enoxolone concentration be 0.1 μ g/mL, the concentration of flavanones is 0.5 μ g/mL, the concentration of 6-caprolactone is 2 μ g/mL, 2-
The concentration of aminopyridine is 0.2 μ g/mL.
Beneficial effects of the present invention: the present invention detects a variety of arachidonic acid-type compounds simultaneously, passes through ethyl acetate
The extraction of single solvent is compared with the combination of two kinds of solvents of MTBE, for arachidonic acid substance, not only recovery rate is higher, and
Signal-to-noise ratio when detection is obviously improved, and the method for the present invention significantly improves the detection sensitivity of the substance.
Detailed description of the invention
In order to illustrate the technical solution of the embodiments of the present invention more clearly, required use in being described below to embodiment
Attached drawing be briefly described, it should be apparent that, drawings in the following description are only some embodiments of the invention, for this
For the those of ordinary skill of field, without any creative labor, it can also be obtained according to these attached drawings other
Attached drawing.Wherein:
Fig. 1 is that 23 chromatographies for cultivating peanut tetraenoic acid detection go out peak figure.
Fig. 2 is overlap of peaks situation map of the present invention 17 mixed mark quality-control products on liquid chromatograph-mass spectrometer device.
Specific embodiment
In order to make the foregoing objectives, features and advantages of the present invention clearer and more comprehensible, right combined with specific embodiments below
A specific embodiment of the invention is described in detail.
In the following description, numerous specific details are set forth in order to facilitate a full understanding of the present invention, but the present invention can be with
Implemented using other than the one described here other way, those skilled in the art can be without prejudice to intension of the present invention
In the case of do similar popularization, therefore the present invention is not limited by the specific embodiments disclosed below.
Secondly, " one embodiment " or " embodiment " referred to herein, which refers to, may be included at least one realization side of the invention
A particular feature, structure, or characteristic in formula." in one embodiment " that different places occur in the present specification not refers both to
The same embodiment, nor the individual or selective embodiment mutually exclusive with other embodiments.
Embodiment 1:
Using the triple level four bars of ultra performance liquid chromatography -/linear ion hydrazine tandem mass spectrum (UPLC-QTRAP) technology, matter
Spectrometer is AB Sciex Q-TRAP 6500, and analysis software is Multi Quant.
It takes the human plasma sample of 100uL in EP pipe, adds the water of 300uL (containing 0.005%BHT)；
Into EP pipe be added 500uL MTBE (methyl tertiary butyl ether(MTBE)), be vortexed mix, under the conditions of 4 DEG C 10000rpm from
It after heart 3min, is transferred to upper layer is organic in new EP pipe, retains lower layer's water phase；
The ethyl acetate of 500uL is added into the water phase of lower layer, is vortexed after mixing, 10000rpm is centrifuged under the conditions of 4 DEG C
After 3min, upper organic phase is merged with the upper organic phase that previous step obtains；
By combined upper organic phase with after being dried with nitrogen, is redissolved, is packed into sample bottle using acetonitrile/isopropanol (1:1),
Upper machine testing.
Liquid chromatography mass spectrometric condition:
Mobile phase A is mutually acetonitrile/water/acetic acid=60/40/0.02 (v/v/v), and B phase is 50/50 (v/ of acetonitrile/isopropanol
V), flow velocity 0.4mL/min, 40 DEG C of column temperature, sample injector temperature: 4 DEG C, 10 μ L of sample volume, chromatographic column: ACQUITY UPLC HSS
T3 (i.d.2.1x100mm, 1.8 μm), MRM detection window are set as 60sec, Target Scan Time setting
It is -4500V for 1.000sec, IonSpray Voltage, Ion Mode is negative, and Temperature is 550 DEG C, Ion
Source Gas 1 is 50psi, and Ion Source Gas 2 is 60psi, and Entrance Potential is 10psi, Curtain
Gas is 35psi, and eluent gradient see the table below:
| Time(min) | A (%) | B (%) |
| 0 | 99.9 | 0.1 |
| 4.0 | 45 | 55 |
| 5.0 | 1 | 99 |
| 6.8 | 1 | 99 |
| 7.0 | 99.9 | 0.1 |
| 10.0 | Stop |
The ion pair information of upper machine:
Upper machine testing chromatogram is shown in Fig. 1, it will be seen from figure 1 that chromatographic peak separation is good using sample of the present invention extracting method
It is good, and repeatability is good.
In addition, the present invention uses 2- chlorophenylalanine as internal standard, the internal standard for using water to be configured to 1 μ g/mL as solvent is mentioned
Liquid is taken, replaces pure organic solvent to extract experiment sample with internal standard 2- chlorophenylalanine extracting solution, guarantees in each sample
Interior target concentration is consistent, acquires situation by interior target, reflects the acquisition situation of actual sample.For instrument during monitor and detection
Device operating status normally whether, metabolism group detection quality-control product of the present invention is made of the mixed mark of 17 by screening, and 17 are mixed
The methanol-water that target solvent is 70%, of the invention to be shown in Table 1 with 17 standard specimens of quality-control product and its using final concentration:
Table 1
Overlap of peaks situation map of 17 mixed mark quality-control products on liquid chromatograph-mass spectrometer device is shown in Fig. 2.It can be with from Fig. 2
Finding out, the peak area RSD of the repeating sample of 17 mixed mark quality-control products is within 10%, due under experiment condition of the present invention, 17
The retention time of a mixed mark quality-control product is dispersed in 0.5~6.5min, and the retention time of sample is dispersed in 0.5~6min, and
And the mixed mark quality-control product of the present invention 17 is reproducible, chromatographic peak is separated and be overlapped, the present invention 17 mixed mark quality-control products can
Accurately reflect in the stability run to quasi-arachidonic acid substance detection process Instrumental.
The detection limit for each quasi-arachidonic acid substance that the present invention can detect in the same reacting hole is as follows
Table:
| Substance title | Detection limit (nM) |
| 5-HETrE | 1.00 |
| RvD1 | 1.00 |
| LTB4 | 1.00 |
| (±)5-HEPE | 0.10 |
| (±)4-HDHA | 0.10 |
| 13-HOTrE | 0.10 |
| PGD2 | 0.10 |
| 5,6-DiHETrE | 0.10 |
| TxB3 | 0.10 |
| 9-HOTrE | 0.10 |
| (±)8-HETE | 0.10 |
| 9,10-DiHOME | 0.10 |
| (±)17-HDHA | 0.10 |
| PGE3 | 0.10 |
| (±)15-HETE | 0.10 |
| (±)16-HETE | 1.00 |
| PGJ2 | 1.00 |
| 5(S),6(S)-DiHETE | 1.00 |
| 5(S),15(S)-DiHETE | 1.00 |
| (±)7-HDHA | 1.00 |
| PGK1 | 1.00 |
| PDX | 1.00 |
| 5-oxoETE | 1.00 |
Embodiment 2 (reference examples):
It takes the plasma sample of 100uL in EP pipe, adds the water of 300uL (containing 0.005%BHT)；
Into EP pipe be added 500uL MTBE (methyl tertiary butyl ether(MTBE)), be vortexed mix, under the conditions of 4 DEG C 10000rpm from
It after heart 3min, is transferred to upper layer is organic in new EP pipe, retains lower layer's water phase；
The MTBE (methyl tertiary butyl ether(MTBE)) of 500uL is added into the water phase of lower layer, is vortexed after mixing, under the conditions of 4 DEG C
After 10000rpm is centrifuged 3min, upper organic phase is merged with the upper organic phase that previous step obtains；
By combined upper organic phase with after being dried with nitrogen, is redissolved, is packed into sample bottle using acetonitrile/isopropanol (1:1),
To upper machine testing.
Embodiment 3 (reference examples):
It takes the plasma sample of 100uL in EP pipe, adds the water of 300uL (containing 0.005%BHT)；
The ethyl acetate of 500uL is added into EP pipe, is vortexed and mixes, it, will after 10000rpm is centrifuged 3min under the conditions of 4 DEG C
Upper layer is organic to be transferred in new EP pipe, and lower layer's water phase is retained；
The ethyl acetate of 500uL is added into the water phase of lower layer, is vortexed after mixing, 10000rpm is centrifuged under the conditions of 4 DEG C
After 3min, upper organic phase is merged with the upper organic phase that previous step obtains；
By combined upper organic phase with after being dried with nitrogen, is redissolved, is packed into sample bottle using acetonitrile/isopropanol (1:1),
To upper machine testing.
Examples 1 to 3 extracting method extracts the comparison of quasi-arachidonic acid substance signal-to-noise ratio and is shown in Table 1.Examples 1 to 3 mentions
The recovery rate for taking method to extract quasi-arachidonic acid substance is shown in Table 2.The calculating of recovery rate uses the calculating side of recovery of standard addition
The standard items of 20mM are added in method that is, in sample to be tested, are detected after extracting sample, calculation formula are as follows: (added standard items
Sample peak area-plus the sample peak face of standard items)/independent examination criteria product peak area.
1 Examples 1 to 3 extracting method of table extracts the comparison of quasi-arachidonic acid substance signal-to-noise ratio
The recovery rate of 2 Examples 1 to 3 extracting method of table extraction quasi-arachidonic acid substance
The present invention detects a variety of arachidonic acid-type compounds simultaneously, passes through the knot of two kinds of solvents of ethyl acetate and MTBE
The extraction for comparing single solvent is closed, not only recovery rate is higher for arachidonic acid substance, and signal-to-noise ratio when detecting obtains
It is obviously improved, the method for the present invention significantly improves the detection sensitivity of the substance.
It should be noted that the above examples are only used to illustrate the technical scheme of the present invention and are not limiting, although referring to preferable
Embodiment describes the invention in detail, those skilled in the art should understand that, it can be to technology of the invention
Scheme is modified or replaced equivalently, and without departing from the spirit and scope of the technical solution of the present invention, should all be covered in this hair
In bright scope of the claims.
Claims (9)
1. a kind of quasi-arachidonic acid substance detection method, it is characterised in that: including,
With volume fraction, 300 parts of water containing 0.005%BHT are added in 100 parts of sample；
500 parts of methyl tertiary butyl ether(MTBE) is added, upper organic phase is shifted in centrifugation, retains lower layer's water phase；
500 parts of ethyl acetate, centrifugation, the upper layer that upper organic phase and previous step are obtained are added into lower layer's water phase
Organic phase merges；
By combined upper organic phase with after being dried with nitrogen, acetonitrile-aqueous isopropanol is used to redissolve, upper machine testing.
2. quasi-arachidonic acid substance detection method as described in claim 1, it is characterised in that: 500 parts of the addition
Methyl tertiary butyl ether(MTBE), centrifugation, 10000rpm is centrifuged 3min under the conditions of being included in 4 DEG C；500 parts are added into lower layer's water phase
Ethyl acetate, centrifugation, 10000rpm is centrifuged 3min under the conditions of being included in 4 DEG C.
3. quasi-arachidonic acid substance detection method as claimed in claim 1 or 2, it is characterised in that: described to use acetonitrile-
Aqueous isopropanol redissolves, wherein with volume basis, acetonitrile: isopropanol=1:1.
4. quasi-arachidonic acid substance detection method as claimed in claim 1 or 2, it is characterised in that: the sample, including
Plasma sample.
5. quasi-arachidonic acid substance detection method as claimed in claim 1 or 2, it is characterised in that: further include, by 2- chlorine
Phenylalanine replaces solvent as internal standard, in the detection process, is reflected by 2- chlorophenylalanine peak area and retention time real
The acquisition situation of border sample.
6. quasi-arachidonic acid substance detection method as claimed in claim 5, it is characterised in that: the 2- chlorophenylalanine
Concentration is 1 μ g/mL.
7. the quasi-arachidonic acid substance detection method as described in any in claim 1,2,6, it is characterised in that: also wrap
Include, using 4,4 '-di-2-ethylhexylphosphine oxides (2- chloroaniline), P-anisidine, l-tyrosine methyl esters, 3- chloroaniline, 2,4- dimethyl quinoline,
Sulfapryidine, Atrazine, sulfadoxine, DL-leucine, N- benzoyl-l-tyrosine ethyl ester, 6- phenyl -2- thiocarbamide are phonetic
Pyridine, N- (toluoyl) glycine, Metronidazole, enoxolone, flavanones, 6-caprolactone, 2- ammonia
The mixed sample of yl pyridines is as quality-control product, and detection is at least into two needle quality-control products every time, according to spectrogram overlapping cases analysis detection
The state of instrument.
8. quasi-arachidonic acid substance detection method as claimed in claim 7, it is characterised in that: by quality ratio, described
4,4 '-di-2-ethylhexylphosphine oxides (2- chloroaniline): P-anisidine: l-tyrosine methyl esters: 3- chloroaniline: 2,4- dimethyl quinolines: sulfanilamide (SN) pyrrole
Pyridine: Atrazine: sulfadoxine: DL-leucine: N- benzoyl-l-tyrosine ethyl ester: 6- phenyl -2- deracil: N-
(toluoyl) glycine: Metronidazole: enoxolone: flavanones: 6-caprolactone: 2-aminopyridine
=1:0.5:0.5:2:1:0.4:0.1:0.1:0.2:0.5:0.5:1:1:0.1:0.5:2:0.2.
9. quasi-arachidonic acid substance detection method as claimed in claim 8, it is characterised in that: described 4,4 '-methylene
The concentration of bis- (2- chloroanilines) is 1 μ g/mL, the concentration of P-anisidine is 0.5 μ g/mL, the concentration of l-tyrosine methyl esters is 0.5 μ
The concentration of g/mL, 3- chloroaniline is 2 μ g/mL, the concentration of 2,4- dimethyl quinoline is 1 μ g/mL, the concentration of sulfapryidine is 0.4 μ
G/mL, Atrazine concentration be 0.1 μ g/mL, the concentration of sulfadoxine is 0.1 μ g/mL, the concentration of DL-leucine is 0.2 μ
G/mL, N- benzoyl-l-tyrosine ethyl ester concentration are 0.5 μ g/mL, the concentration of 6- phenyl -2- deracil is 0.5 μ g/
The concentration of mL, N- (toluoyl) glycine is 1 μ g/mL, the concentration of Metronidazole is 1 μ g/mL, sweet
The concentration of careless hypo acid is 0.1 μ g/mL, the concentration of flavanones is 0.5 μ g/mL, the concentration of 6-caprolactone is 2 μ g/mL, 2- amino pyrrole
The concentration of pyridine is 0.2 μ g/mL.
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