PC(P-16:0/20:4(5Z,8Z,11Z,14Z)) | 84460-45-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: PC(P-16:0/20:4(5Z,8Z,11Z,14Z))
• 英文别名: [(2R)-3-[(Z)-hexadec-1-enoxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 84460-45-7
• 化学式: C44H80NO7P
• 分子量: 766.1
• InChiKey: IOYKZPNDXIIXLN-LOQSCQKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  53
• 可旋转键数：
  39
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  PC(P-16:0/20:4(5Z,8Z,11Z,14Z)) 、 水 生成 Arachidonate 、 (R)-(-)-1-O-(1'-(Z)-hexadecenyl)glycero-3-phosphocholine 、 氢(+1)阳离子
  参考文献：
  名称：

  The Highly Selective Production of 2-Arachidonoyl Lysophosphatidylcholine Catalyzed by Purified Calcium-independent Phospholipase A2γ

  摘要：

  Herein, we report the heterologous expression of the human peroxisomal 63-kDa calcium-independent phospholipase A(2)gamma (iPLA(2)gamma) isoform in Sf9 cells, purification of the N-terminal His-tagged enzyme by affinity chromatography, and the identification of its remarkable substrate selectivity that results in the highly selective generation of 2-arachidonoyl lysophosphatidylcholine. Mass spectrometric analyses demonstrated that purified iPLA(2)gamma hydrolyzed saturated or monounsaturated aliphatic groups readily from either the sn-1 or sn-2 positions of phospholipids. In addition, purified iPLA(2)gamma effectively liberated arachidonic acid from the sn-2 position of plasmenylcholine substrates. In contrast, incubation of iPLA(2)gamma with 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine resulted in the rapid release of palmitic acid and the selective accumulation of 2-arachidonoyl lysophosphatidylcholine (LPC), which was not metabolized further by iPLA(2)gamma. The putative regiospecificity of the 2-arachidonoyl LPC product was authenticated by its diagnostic fragmentation pattern during tandem mass spectrometric analysis. To identify the physiological relevance of iPLA(2)gamma-mediated 2-arachidonoyl LPC production utilizing naturally occurring membranes, we incubated purified rat hepatic peroxisomes with iPLA(2)gamma and similarly identified the selective accumulation of 2-arachidonoyl LPC. Furthermore, tandem mass spectrometric analysis demonstrated that 2-arachidonoyl LPC is a natural product in human myocardium, a tissue in which iPLA(2)gamma expression is robust. Because 2-arachidonoyl LPC represents a key branch point intermediate that can potentially lead to a variety of bioactive molecules in eicosanoid signaling (e.g. arachidonic acid, 2-arachidonoylglycerol), these results have uncovered a novel eicosanoid selective pathway through iPLA(2)gamma-mediated 2-arachidonoyl LPC production to amplify and diversify the repertoire of biologic lipid second messengers in response to cellular stimulation.

  DOI：

  10.1074/jbc.m502358200

文献信息

• Oxidized lipids and uses thereof in the treatment of inflammatory diseases and disorders
  申请人：Harats Dror

  公开号：US20100048515A1

  公开（公告）日：2010-02-25

  Novel synthetic oxidized lipids and methods utilizing oxidized lipids for treating and preventing an inflammation associated with an endogenous oxidized lipid are provided.

  提供了一种新型合成的氧化脂质以及利用氧化脂质用于治疗和预防与内源性氧化脂质相关的炎症的方法。
• NANOPARTICLE-BASED DELIVERY SYSTEM WITH OXIDIZED PHOSPHOLIPIDS AS TARGETING LIGANDS FOR THE PREVENTION, DIAGNOSIS AND TREATMENT OF ATHEROSCLEROSIS
  申请人：WANG Shu

  公开号：US20140287024A1

  公开（公告）日：2014-09-25

  Disclosed are nanoparticle-based medicine/nutrient delivery system that are coated or incorporated with oxidized phospholipids as targeting ligands. Such delivery systems can specifically target macrophages, which are determinant cells in the aortic wall for atherosclerotic lesion development, to significantly increase bioavailability and specificity for the prevention, diagnosis and treatment of atherosclerosis.

  揭示了一种基于纳米颗粒的医药/营养素传递系统，其涂有或包含氧化磷脂作为靶向配体。这样的传递系统可以特异性地靶向巨噬细胞，它们是动脉壁上动脉粥样硬化病变发展的决定性细胞，从而显着增加生物利用度和特异性，用于预防、诊断和治疗动脉粥样硬化。
• Method for the diagnosis of non-alcoholic steatohepatitis based on a metabolomic profile
  申请人：One Way Liver Genomics, S.L.

  公开号：EP2309276A1

  公开（公告）日：2011-04-13

  The invention relates to methods for the diagnosis of non-alcoholic steatosis (NASH). The method relies on the determination of certain metabolic markers in a biological sample of the patient which are up- or down-regulated in the NASH patients vs. patients with a simple fatty liver (steatosis).

  本发明涉及诊断非酒精性脂肪肝（NASH）的方法。该方法依赖于测定患者生物样本中的某些代谢标记物，这些标记物在非酒精性脂肪肝患者与单纯脂肪肝（脂肪变性）患者中上调或下调。
• METHOD FOR THE DIAGNOSIS OF NON-ALCOHOLIC STEATOHEPATITIS BASED ON A METABOLOMIC PROFILE
  申请人：Barr Jonathan

  公开号：US20120187289A1

  公开（公告）日：2012-07-26

  The invention relates to methods for the diagnosis of non-alcoholic steatosis (NASH). The method relies on the determination of certain metabolic markers in a biological sample of the patient which are up- or down-regulated in the NASH patients vs. patients with a simple fatty liver (steatosis).
• US7973023B2
  申请人：——

  公开号：US7973023B2

  公开（公告）日：2011-07-05