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 (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20200033360A1 (en) * | 2017-03-31 | 2020-01-30 | 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 |
| 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 |
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 |
| 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 |
| WO2008118457A2 (en) * | 2007-03-26 | 2008-10-02 | University Of Medicine And Dentistry Of Nj | Synthesis of resolvins and intermediates, compounds prepared thereby, and uses thereof |
| 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 |
| 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 ES ES15827995T patent/ES2978375T3/es active Active
- 2015-07-30 AU AU2015296304A patent/AU2015296304B2/en active Active
- 2015-07-30 JP JP2017505546A patent/JP6810023B2/ja 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 CN CN201580040519.5A patent/CN107075539B/zh active Active
- 2015-07-30 EP EP15827995.0A patent/EP3174991B1/en active Active
-
2016
- 2016-08-30 US US15/251,579 patent/US11181535B2/en active Active
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