CA2955204A1 - Methods, compositions, and kits for analysis of structurally diverse complex lipids - Google Patents
Methods, compositions, and kits for analysis of structurally diverse complex lipids Download PDFInfo
- Publication number
- CA2955204A1 CA2955204A1 CA2955204A CA2955204A CA2955204A1 CA 2955204 A1 CA2955204 A1 CA 2955204A1 CA 2955204 A CA2955204 A CA 2955204A CA 2955204 A CA2955204 A CA 2955204A CA 2955204 A1 CA2955204 A1 CA 2955204A1
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- CA
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- Prior art keywords
- lipid
- sample
- fatty acids
- mixture
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000002632 lipids Chemical class 0.000 title claims abstract description 752
- 239000000203 mixture Substances 0.000 title claims abstract description 743
- 238000000034 method Methods 0.000 title claims abstract description 176
- 238000004458 analytical method Methods 0.000 title claims description 22
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 567
- 229930195729 fatty acid Natural products 0.000 claims description 567
- 239000000194 fatty acid Substances 0.000 claims description 567
- 150000004665 fatty acids Chemical class 0.000 claims description 565
- 239000000523 sample Substances 0.000 claims description 325
- 241000894007 species Species 0.000 claims description 134
- -1 6-hydroxyceramide Chemical compound 0.000 claims description 103
- 239000012472 biological sample Substances 0.000 claims description 88
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 82
- 229910052805 deuterium Inorganic materials 0.000 claims description 82
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 68
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 67
- 125000002252 acyl group Chemical group 0.000 claims description 64
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 54
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 53
- 150000001982 diacylglycerols Chemical class 0.000 claims description 47
- YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 0.000 claims description 46
- 150000003904 phospholipids Chemical class 0.000 claims description 39
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 34
- 210000002966 serum Anatomy 0.000 claims description 32
- 150000003626 triacylglycerols Chemical class 0.000 claims description 32
- 210000002381 plasma Anatomy 0.000 claims description 30
- 235000021588 free fatty acids Nutrition 0.000 claims description 29
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims description 24
- 229940049964 oleate Drugs 0.000 claims description 23
- 229940106189 ceramide Drugs 0.000 claims description 22
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 22
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 21
- 238000005917 acylation reaction Methods 0.000 claims description 21
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims description 21
- 230000000155 isotopic effect Effects 0.000 claims description 21
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims description 21
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 21
- 229940067605 phosphatidylethanolamines Drugs 0.000 claims description 21
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 20
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims description 20
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 20
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 claims description 20
- ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 claims description 20
- 150000003905 phosphatidylinositols Chemical class 0.000 claims description 20
- 210000002700 urine Anatomy 0.000 claims description 20
- JSPNNZKWADNWHI-PNANGNLXSA-N (2r)-2-hydroxy-n-[(2s,3r,4e,8e)-3-hydroxy-9-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]heptadecanamide Chemical compound CCCCCCCCCCCCCCC[C@@H](O)C(=O)N[C@H]([C@H](O)\C=C\CC\C=C(/C)CCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JSPNNZKWADNWHI-PNANGNLXSA-N 0.000 claims description 19
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims description 19
- CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 claims description 19
- WPIHMWBQRSAMDE-YCZTVTEBSA-N beta-D-galactosyl-(1->4)-beta-D-galactosyl-N-(pentacosanoyl)sphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)[C@H](O)\C=C\CCCCCCCCCCCCC WPIHMWBQRSAMDE-YCZTVTEBSA-N 0.000 claims description 19
- 229930183167 cerebroside Natural products 0.000 claims description 19
- RIZIAUKTHDLMQX-UHFFFAOYSA-N cerebroside D Natural products CCCCCCCCCCCCCCCCC(O)C(=O)NC(C(O)C=CCCC=C(C)CCCCCCCCC)COC1OC(CO)C(O)C(O)C1O RIZIAUKTHDLMQX-UHFFFAOYSA-N 0.000 claims description 19
- 150000002270 gangliosides Chemical class 0.000 claims description 19
- 150000002305 glucosylceramides Chemical class 0.000 claims description 19
- 229930000756 phytoceramide Natural products 0.000 claims description 19
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 18
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 150000003727 wax diesters Chemical class 0.000 claims description 17
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 claims description 16
- 125000005313 fatty acid group Chemical group 0.000 claims description 16
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims description 16
- WRGQSWVCFNIUNZ-GDCKJWNLSA-N 1-oleoyl-sn-glycerol 3-phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O WRGQSWVCFNIUNZ-GDCKJWNLSA-N 0.000 claims description 15
- ZPDQFUYPBVXUKS-YADHBBJMSA-N 1-stearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC[C@H](N)C(O)=O ZPDQFUYPBVXUKS-YADHBBJMSA-N 0.000 claims description 15
- 210000004369 blood Anatomy 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 15
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims description 15
- UOXRPRZMAROFPH-IESLQMLBSA-N lysophosphatidylinositol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC1[C@H](O)[C@@H](O)C(O)[C@@H](O)[C@H]1O UOXRPRZMAROFPH-IESLQMLBSA-N 0.000 claims description 15
- 238000004949 mass spectrometry Methods 0.000 claims description 15
- 102000004895 Lipoproteins Human genes 0.000 claims description 14
- 108090001030 Lipoproteins Proteins 0.000 claims description 14
- 239000004164 Wax ester Substances 0.000 claims description 14
- 238000004587 chromatography analysis Methods 0.000 claims description 14
- 235000019386 wax ester Nutrition 0.000 claims description 14
- 230000001413 cellular effect Effects 0.000 claims description 13
- 210000004880 lymph fluid Anatomy 0.000 claims description 13
- 210000003296 saliva Anatomy 0.000 claims description 13
- 210000001519 tissue Anatomy 0.000 claims description 13
- 238000004817 gas chromatography Methods 0.000 claims description 12
- 150000008105 phosphatidylcholines Chemical class 0.000 claims description 12
- 238000004809 thin layer chromatography Methods 0.000 claims description 11
- LRYZPFWEZHSTHD-HEFFAWAOSA-O 2-[[(e,2s,3r)-2-formamido-3-hydroxyoctadec-4-enoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical class CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](NC=O)COP(O)(=O)OCC[N+](C)(C)C LRYZPFWEZHSTHD-HEFFAWAOSA-O 0.000 claims description 10
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 10
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 10
- 239000012805 animal sample Substances 0.000 claims description 10
- 125000000403 lignoceroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 238000005251 capillar electrophoresis Methods 0.000 claims description 8
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 claims description 8
- 229940000640 docosahexaenoate Drugs 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 238000004255 ion exchange chromatography Methods 0.000 claims description 5
- 238000004007 reversed phase HPLC Methods 0.000 claims description 5
- 238000001542 size-exclusion chromatography Methods 0.000 claims description 5
- 239000013068 control sample Substances 0.000 claims description 3
- 125000003473 lipid group Chemical group 0.000 claims 98
- 125000000016 octadecenoyl group Chemical group O=C([*])C([H])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 1
- 238000011002 quantification Methods 0.000 abstract description 8
- 238000001514 detection method Methods 0.000 abstract description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 18
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000003556 assay Methods 0.000 description 13
- 241000124008 Mammalia Species 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 10
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 10
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000003018 immunoassay Methods 0.000 description 7
- 230000009897 systematic effect Effects 0.000 description 7
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 6
- 238000002965 ELISA Methods 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 5
- 238000002372 labelling Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000252212 Danio rerio Species 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 125000004431 deuterium atom Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- SUHOQUVVVLNYQR-MRVPVSSYSA-O glycerylphosphorylcholine Chemical compound C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-O 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 101100321670 Fagopyrum esculentum FA18 gene Proteins 0.000 description 3
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 125000003374 diacylglycerol group Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229940049918 linoleate Drugs 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007430 reference method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 241001432959 Chernes Species 0.000 description 2
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- 101100223822 Dictyostelium discoideum zfaA gene Proteins 0.000 description 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 2
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- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
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- 235000005911 diet Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
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- 238000001962 electrophoresis Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- BPMFZUMJYQTVII-UHFFFAOYSA-N guanidinoacetic acid Chemical compound NC(=N)NCC(O)=O BPMFZUMJYQTVII-UHFFFAOYSA-N 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
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- 238000004806 packaging method and process Methods 0.000 description 2
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- 229940076279 serotonin Drugs 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 150000004666 short chain fatty acids Chemical class 0.000 description 2
- 150000003408 sphingolipids Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003203 triacylglycerol group Chemical group 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 238000010200 validation analysis Methods 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 description 1
- ALFPYCWNTIZXMT-MHYRICRISA-N (E,2R,3R)-2-aminooctadec-4-ene-1,1,3-triol Chemical compound OC(O)[C@H](N)[C@H](O)\C=C\CCCCCCCCCCCCC ALFPYCWNTIZXMT-MHYRICRISA-N 0.000 description 1
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- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
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- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
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| PCT/US2015/042904 WO2016019140A1 (en) | 2014-07-30 | 2015-07-30 | Methods, compositions, and kits for analysis of structurally diverse complex lipids |
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| JP7306676B2 (ja) * | 2019-02-26 | 2023-07-11 | 国立大学法人九州大学 | 脂質プロファイリングシステム、脂質プロファイリング方法、及び脂質プロファイリングプログラム |
| CN114144679A (zh) * | 2019-06-04 | 2022-03-04 | 阿凡提极性脂质有限责任公司 | 用于脂质组学中的通用脂质定量标准 |
| CN110609097A (zh) * | 2019-09-12 | 2019-12-24 | 谱尼测试集团股份有限公司 | 一种磷脂酰丝氨酸类化合物的筛查方法 |
| CN116106283B (zh) * | 2023-02-16 | 2025-07-29 | 清华大学 | 缩醛磷脂的荧光分析方法与应用 |
| WO2025009258A1 (ja) * | 2023-07-03 | 2025-01-09 | 株式会社島津製作所 | コリン部分に安定同位体元素を含むリゾホスファチジルコリン化合物を用いた分析方法 |
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| EP1490076A4 (en) | 2002-03-11 | 2010-01-06 | Lipomics Technologies Inc | NEW METABOLIC TARGETS AND MARKERS |
| US7306952B2 (en) * | 2002-06-26 | 2007-12-11 | Washington University In St. Louis | Molecular fingerprinting of triglycerides in biological samples by electrospray ionization tandem mass spectrometry |
| CA2532038C (en) * | 2003-07-11 | 2013-11-26 | Tatiana A. Egorova-Zachernyuk | Compositions and methods for stable isotope labelling of biological compounds |
| CN100567967C (zh) * | 2006-08-31 | 2009-12-09 | 华南理工大学 | 一种定量测定纸浆树脂中甘油三酯含量的方法 |
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| CN102105792A (zh) * | 2008-05-28 | 2011-06-22 | 巴斯夫欧洲公司 | 评估肝毒性的工具和方法 |
| US8263413B1 (en) * | 2008-10-17 | 2012-09-11 | Andrew S Hansen | Methods for analyzing lipids and membrane proteins in biological matter using stable isotopes and mass spectrometry |
| US10024857B2 (en) | 2009-10-01 | 2018-07-17 | Med-Life Discoveries Lp | Serum-based biomarkers of pancreatic cancer and uses thereof for disease detection and diagnosis |
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| CN103743851B (zh) * | 2014-02-14 | 2015-06-17 | 中国农业科学院油料作物研究所 | 一种食用油中甘油三酯的单柱二维液相色谱-质谱分析方法及其应用 |
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| AU2015296304A1 (en) | 2017-02-02 |
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| CN107075539B (zh) | 2021-11-12 |
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