9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: MFZRTUAMBHHFIO-QRQQZPNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  77.76
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 soybean 15-lipoxygenase E_.C_. 1.13.11.12, Type 1-B 、 sodium tetrahydroborate 作用下， 以 aq. buffer 为溶剂， 生成 9(R),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid 、 9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid 、 9(S),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid 、 9(R),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid
  参考文献：
  名称：

  Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA

  摘要：

  We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E,Z,E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from alpha-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10E,12 Z,14E-octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX.

  DOI：

  10.1194/jlr.m035139

文献信息

• Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA
  作者：Miao Liu、Ping Chen、Evelyne Véricel、Moreno Lelli、Laetitia Béguin、Michel Lagarde、Michel Guichardant

  DOI：10.1194/jlr.m035139

  日期：2013.8

  We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E,Z,E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from alpha-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12E,14E-octadecatrienoic acid, 9(S),16(S)-dihydroxy-10E,12Z,14E-octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10E,12 Z,14E-octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX.