1,2-dieicosapentanoylglycero-3-phophocholine | 98819-78-4

• 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: 1,2-dieicosapentanoylglycero-3-phophocholine
• 英文别名: 1,2-dieicosapentaenoyl-sn-glycero-3-phosphocholine；dieicosapentaenoyl phosphatidylcholine；2,3-bis[[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl]oxy]propyl 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 98819-78-4
• 化学式: C₄₈H₇₆NO₈P
• 分子量: 826.107
• InChiKey: WAIHGVAZVKEQGR-IYICPNJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  58
• 可旋转键数：
  38
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-dieicosapentanoylglycero-3-phophocholine 在 4-二甲氨基吡啶 、 phospholipase C from Clostridium perfringens (Clostridium welchii) Type I 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 [2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl]oxy-3-tetradecanoyloxypropyl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
  参考文献：
  名称：

  Temperature dependence of production of structured triacylglycerols in the alga Trachydiscus minutus

  摘要：

  This study describes the identification of regioisomers and enantiomers of triacylglycerols of C20 polyunsaturated fatty acids (PUFAs) in the alga Trachydiscus minutus cultivated at different temperatures using reversed- and chiral-phase liquid chromatography-mass spectrometry. The use of the two different phases contributes to ready identification, both qualitative and semiquantitative, of regioisomers and enantiomers of triacylglycerols containing eicosapentaenoic and arachidonic in the molecule. The ratio of regioisomers and enantiomers of triacylglycerols (TAG) depends on the temperature of cultivation; with lowering temperature the proportion of the achiral TAG increases and the enantiomer ratio diverges from 1:1. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.12.013
• 作为产物：
  描述：

  全顺式二十碳五烯酸 、 2,3-二羟丙基(2-(三甲基铵)乙基)磷酸酯 在 N,N'-羰基二咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 24.0h， 以18.2%的产率得到1,2-dieicosapentanoylglycero-3-phophocholine
  参考文献：
  名称：

  Synthesis of Eicosapentaenoic Acid-enriched Phosphatidylcholine and its Effect on Pro-inflammatory Cytokine Expression

  摘要：

  目的和目标： 我们合成了富含二十碳五烯酸磷脂酰胆碱(EPA-PC)，并研究了其对小鼠脾细胞内脂多糖(LPS)诱导的细胞因子产生的影响。 材料和方法： 将暴露于EPA-PC和LPS的脾细胞的培养上清液收集，以确定细胞因子[白细胞介素(IL)-4、IL-5、IL-6、干扰素(IFN)-γ、IL-2和IL-12/IL-23(p40)]的产生。细胞因子使用酶联免疫吸附法(ELISA)进行测量。 结果： EPA-PC与LPS联合给药导致IFN-γ表达显著降低，比单独使用LPS观察到的效果更好(p <0.01)。此外，EPA-PC和LPS的治疗显著降低了IL-2、IL-6和IL-12/IL-23(p40)的表达(p <0.01)。与单独使用LPS相比，EPA-PC浓度为0.3 μg/mL与LPS联合治疗24小时后，IL-5表达更高(p <0.05)。 结论： 这些结果表明，在炎症诱导时，EPA-PC在降低促炎细胞因子(IL-2、IFN-γ、IL-6和IL-12/IL-23(p40))的表达方面更为有效。

  DOI：

  10.2174/1386207324666210118100049

文献信息

• Temperature dependence of production of structured triacylglycerols in the alga Trachydiscus minutus
  作者：Tomáš Řezanka、Jaromír Lukavský、Karel Sigler、Linda Nedbalová、Milada Vítová

  DOI：10.1016/j.phytochem.2014.12.013

  日期：2015.2

  This study describes the identification of regioisomers and enantiomers of triacylglycerols of C20 polyunsaturated fatty acids (PUFAs) in the alga Trachydiscus minutus cultivated at different temperatures using reversed- and chiral-phase liquid chromatography-mass spectrometry. The use of the two different phases contributes to ready identification, both qualitative and semiquantitative, of regioisomers and enantiomers of triacylglycerols containing eicosapentaenoic and arachidonic in the molecule. The ratio of regioisomers and enantiomers of triacylglycerols (TAG) depends on the temperature of cultivation; with lowering temperature the proportion of the achiral TAG increases and the enantiomer ratio diverges from 1:1. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Eicosapentaenoic Acid-enriched Phosphatidylcholine and its Effect on Pro-inflammatory Cytokine Expression
  作者：Jae Yeul Baek、Eun Na、Sun Young Lim

  DOI：10.2174/1386207324666210118100049

  日期：2021.1

  We synthesized eicosapentaenoic acid-enriched phosphatidylcholine (EPA-PC) and investigated its effect on the production of lipopolysaccharide (LPS)- induced cytokines in murine splenocytes.

  The culture supernatants of splenocytes, which was exposed to EPA-PC along with LPS, was harvested to determine the production of cytokines [interleukin (IL)-4 , IL-5, IL-6, interferon (IFN)-γ, IL-2 and IL-12/IL-23(p40)]. Cytokines were measured using enzymelinked immunosorbent assay (ELISA).

  The co-administration of EPA-PC with LPS resulted in a significantly lower IFN-γ expression than that observed with LPS alone (p < 0.01). Moreover, treatment with EPA-PC and LPS significantly decreased IL-2, IL-6 and IL-12/IL-23(p40) expression (p < 0.01). Coadministration of EPA-PC at a concentration of 0.3 μg/mL with LPS resulted in a higher IL-5 expression after 24 hr of treatment when compared to LPS alone (p < 0.05).

  These results suggest that EPA-PC is more effective in decreasing the expression of pro-inflammatory cytokines [IL-2, IFN-γ, IL-6 and IL-12/IL-23(p40)] upon induction of inflammation.

  目的和目标： 我们合成了富含二十碳五烯酸磷脂酰胆碱(EPA-PC)，并研究了其对小鼠脾细胞内脂多糖(LPS)诱导的细胞因子产生的影响。 材料和方法： 将暴露于EPA-PC和LPS的脾细胞的培养上清液收集，以确定细胞因子[白细胞介素(IL)-4、IL-5、IL-6、干扰素(IFN)-γ、IL-2和IL-12/IL-23(p40)]的产生。细胞因子使用酶联免疫吸附法(ELISA)进行测量。 结果： EPA-PC与LPS联合给药导致IFN-γ表达显著降低，比单独使用LPS观察到的效果更好(p <0.01)。此外，EPA-PC和LPS的治疗显著降低了IL-2、IL-6和IL-12/IL-23(p40)的表达(p <0.01)。与单独使用LPS相比，EPA-PC浓度为0.3 μg/mL与LPS联合治疗24小时后，IL-5表达更高(p <0.05)。 结论： 这些结果表明，在炎症诱导时，EPA-PC在降低促炎细胞因子(IL-2、IFN-γ、IL-6和IL-12/IL-23(p40))的表达方面更为有效。