JP2017524708A5 - - Google Patents
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- Publication number
- JP2017524708A5 JP2017524708A5 JP2017505546A JP2017505546A JP2017524708A5 JP 2017524708 A5 JP2017524708 A5 JP 2017524708A5 JP 2017505546 A JP2017505546 A JP 2017505546A JP 2017505546 A JP2017505546 A JP 2017505546A JP 2017524708 A5 JP2017524708 A5 JP 2017524708A5
- Authority
- JP
- Japan
- Prior art keywords
- mixture
- lipid
- phosphatidylcholine
- another
- fatty acids
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 claims 65
- 150000002632 lipids Chemical class 0.000 claims 50
- 235000014113 dietary fatty acids Nutrition 0.000 claims 44
- 229930195729 fatty acid Natural products 0.000 claims 44
- 239000000194 fatty acid Substances 0.000 claims 44
- 150000004665 fatty acids Chemical class 0.000 claims 44
- 125000003473 lipid group Chemical group 0.000 claims 23
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims 20
- 150000001982 diacylglycerols Chemical class 0.000 claims 18
- 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 18
- 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 18
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims 18
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims 16
- -1 cholesteryl ester Chemical class 0.000 claims 15
- 229940106189 ceramide Drugs 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 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 12
- 125000002252 acyl group Chemical group 0.000 claims 11
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims 10
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims 8
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims 8
- 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 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims 8
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims 8
- 239000000523 sample Substances 0.000 claims 8
- 238000005917 acylation reaction Methods 0.000 claims 7
- 241000894007 species Species 0.000 claims 7
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 claims 6
- 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 6
- 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 6
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims 6
- 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 6
- 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 6
- 229930183167 cerebroside Natural products 0.000 claims 6
- 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 6
- 150000002270 gangliosides Chemical class 0.000 claims 6
- 150000002305 glucosylceramides Chemical class 0.000 claims 6
- 150000003905 phosphatidylinositols Chemical class 0.000 claims 6
- 150000003904 phospholipids Chemical class 0.000 claims 6
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims 6
- 150000003727 wax diesters Chemical class 0.000 claims 6
- 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 4
- 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 4
- 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 4
- 239000004164 Wax ester Substances 0.000 claims 4
- 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 4
- 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 4
- 150000001784 cerebrosides Chemical class 0.000 claims 4
- 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 4
- 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 4
- 229940049964 oleate Drugs 0.000 claims 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 4
- 229930000756 phytoceramide Natural products 0.000 claims 4
- 235000019386 wax ester Nutrition 0.000 claims 4
- 230000002194 synthesizing effect Effects 0.000 claims 3
- 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 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 2
- 241001483078 Phyto Species 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 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 2
- 239000012472 biological sample Substances 0.000 claims 2
- 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 2
- 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 2
- 125000003374 diacylglycerol group Chemical group 0.000 claims 2
- 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 2
- 229940000640 docosahexaenoate Drugs 0.000 claims 2
- 125000004050 enoyl group Chemical group 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- 210000002751 lymph Anatomy 0.000 claims 1
- 210000002381 plasma Anatomy 0.000 claims 1
- 210000003296 saliva Anatomy 0.000 claims 1
- 210000002966 serum Anatomy 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 210000002700 urine Anatomy 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462031099P | 2014-07-30 | 2014-07-30 | |
| US62/031,099 | 2014-07-30 | ||
| PCT/US2015/042904 WO2016019140A1 (en) | 2014-07-30 | 2015-07-30 | Methods, compositions, and kits for analysis of structurally diverse complex lipids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017524708A JP2017524708A (ja) | 2017-08-31 |
| JP2017524708A5 true JP2017524708A5 (enExample) | 2018-09-06 |
| JP6810023B2 JP6810023B2 (ja) | 2021-01-06 |
Family
ID=55218314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017505546A Active JP6810023B2 (ja) | 2014-07-30 | 2015-07-30 | 構造的に多様な複合脂質を分析するための方法、組成物およびキット |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11181535B2 (enExample) |
| EP (1) | EP3174991B1 (enExample) |
| JP (1) | JP6810023B2 (enExample) |
| CN (1) | CN107075539B (enExample) |
| AU (1) | AU2015296304B2 (enExample) |
| CA (1) | CA2955204A1 (enExample) |
| ES (1) | ES2978375T3 (enExample) |
| WO (1) | WO2016019140A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3602605A4 (en) * | 2017-03-31 | 2020-12-30 | Metabolon, Inc. | COMPREHENSIVE AND QUANTITATIVE LIPID AND TOCOPHEROL ANALYSIS |
| 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 |
| CN116879415A (zh) * | 2023-05-25 | 2023-10-13 | 厦门市迈理奥科技有限公司 | 一种脂质组学分析内标及其用途和检测方法 |
| EP4741813A1 (en) * | 2023-07-03 | 2026-05-13 | Shimadzu Corporation | Analysis method using lysophosphatidylcholine compound containing stable isotope element in choline moiety |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4224031A (en) * | 1977-11-15 | 1980-09-23 | Mee John M L | CI Mass spectrometric analysis of physiologically active compounds |
| GB0128498D0 (en) | 2001-11-28 | 2002-01-23 | Inst Of Child Health | International standards for sphingolipids |
| US20040024065A1 (en) | 2002-03-11 | 2004-02-05 | Watkins Steven M. | Novel 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 |
| AU2004256368B2 (en) * | 2003-07-11 | 2010-08-05 | 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 |
| US20100159540A1 (en) * | 2007-03-26 | 2010-06-24 | Ana Rodriguez | Synthesis of resolvins and intermediates, compounds prepared thereby, and uses thereof |
| EP2286236B1 (en) * | 2008-05-28 | 2016-04-20 | Basf Se | Methods for assessing liver toxicity |
| 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 |
| SG10201405975VA (en) * | 2009-10-01 | 2014-11-27 | Phenomenome Discoveries Inc | Serum-based biomarkers of pancreatic cancer and uses thereof for diseasedetection and diagnosis |
| EP2345897A1 (en) * | 2010-01-18 | 2011-07-20 | Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO | Improved method for the detection of polyunsaturated fatty acids |
| CN101824064A (zh) * | 2010-01-29 | 2010-09-08 | 上海化工研究院 | 一种13c标记胆甾醇羧酸酯的合成方法 |
| GB201213127D0 (en) * | 2012-07-24 | 2012-09-05 | Univ Dundee | Novel isotopic labelling method |
| US10705100B1 (en) * | 2013-09-11 | 2020-07-07 | HB Biotech, LLC | Methods for analyzing lipids and membrane proteins in biological matter using stable isotopes and mass spectrometry |
| 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 |
-
2015
- 2015-07-30 JP JP2017505546A patent/JP6810023B2/ja active Active
- 2015-07-30 CN CN201580040519.5A patent/CN107075539B/zh active Active
- 2015-07-30 EP EP15827995.0A patent/EP3174991B1/en active Active
- 2015-07-30 AU AU2015296304A patent/AU2015296304B2/en active Active
- 2015-07-30 WO PCT/US2015/042904 patent/WO2016019140A1/en not_active Ceased
- 2015-07-30 CA CA2955204A patent/CA2955204A1/en not_active Abandoned
- 2015-07-30 ES ES15827995T patent/ES2978375T3/es active Active
-
2016
- 2016-08-30 US US15/251,579 patent/US11181535B2/en active Active
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