(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid | 143288-65-7

• 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: (7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid
• 英文别名: (7S,8S)-dihydroxylinoleic acid；(9Z,12Z)-(7S,8S)-Dihydroxyoctadeca-9,12-dienoic acid；(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoic acid
• CAS: 143288-65-7
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: NMONGVDUESEHOK-MPOZZNMKSA-N

物化性质

• 沸点：
  476.2±45.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 mycelia of Megaporthe oryzae Guy 11 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 10-hydroxy-(8E,12Z)-octadecanoic acid 、 (5,8)-dihydroxy-(9Z,12Z)-octadecadienoic acid 、 (8R)-hydroxy-(9Z,12Z)-octadecanoic acid 、 (8R)-hydroperoxy-(9Z,12Z)-octadecanoic acid 、 (8R,11S)-8,11-dihydroxy-(9Z,12Z)-octadeca-9,12-dienoic acid 、 (7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid 、 (6S,8R)-dihydroxy-(9Z,12Z)-octadecadienoic acid
  参考文献：
  名称：

  Gene Deletion of 7,8-Linoleate Diol Synthase of the Rice Blast Fungus

  摘要：

  Linoleate diol synthases (LDS) are heme enzymes, which oxygenate 18:2n-6 sequentially to (8R)-hydroperoxylinoleic acid ((8R)-HPODE) and to(5S,8R)-dihydroxy-, (7S,8S)-dihydroxy-, or (8R,11S)-dihydroxylinoleic acids (DiHODE). The genome of the rice blast fungus, Magnaporthe oryzae, contains two genes with homology to LDS. M. oryzae oxidized 18:2n-6 to (8R)-HPODE and to (7S,8S)-DiHODE, (6S,8R)-DiHODE, and (8R,11S)-HODE. Small amounts of 10-hydroxy-(8E,12Z)-octadecadienoic acid and traces of 5,8-DiHODE were also detected by liquid chromatography-mass spectrometry. The contribution of the 7,8-LDS gene to M. oryzae pathogenicity was evaluated by replacement of the catalytic domain with hygromycin and green fluorescent protein variant (SGFP) cassettes. This genetically modified strain Delta 7,8-LDS infected rice leaves and roots and formed appressoria and conidia as the native fungus. The Delta 7,8-LDS mutant had lost the capacity to biosynthesize all the metabolites except small amounts of 8-hydroxylinoleic acid. Studies with stereospecifically deuterated linoleic acids showed that (8R)-HPODE was formed by abstraction of the pro-S hydrogen at C-8 and antarafacial oxygenation, whereas (7S,8S)-DiHODE and (8R,11S)-DiHODE were formed from (8R)-HPODE by suprafacial hydrogen abstraction and oxygenation at C-7 and C-11, respectively. A mac1 suppressor mutant (Delta mac1 sum1-99) of M. oryzae, which shows cAMP-independent protein kinase A activity, oxygenated 18:2n-6 to increased amounts of (10R)-HPODE and (5S,8R)-DiHODE. Expression of the 7,8-LDS gene but not of the second homologue was detected in the suppressor mutant. This suggests that PKA-mediated signaling pathway regulates the dioxygenase and hydroperoxide isomerase activities of M. oryzae.

  DOI：

  10.1074/jbc.m109.062810

文献信息

• Gene Deletion of 7,8-Linoleate Diol Synthase of the Rice Blast Fungus
  作者：Fredrik Jernerén、Ane Sesma、Marina Francheschetti、Mats Hamberg、Ernst H. Oliw

  DOI：10.1074/jbc.m109.062810

  日期：2010.2

  Linoleate diol synthases (LDS) are heme enzymes, which oxygenate 18:2n-6 sequentially to (8R)-hydroperoxylinoleic acid ((8R)-HPODE) and to(5S,8R)-dihydroxy-, (7S,8S)-dihydroxy-, or (8R,11S)-dihydroxylinoleic acids (DiHODE). The genome of the rice blast fungus, Magnaporthe oryzae, contains two genes with homology to LDS. M. oryzae oxidized 18:2n-6 to (8R)-HPODE and to (7S,8S)-DiHODE, (6S,8R)-DiHODE, and (8R,11S)-HODE. Small amounts of 10-hydroxy-(8E,12Z)-octadecadienoic acid and traces of 5,8-DiHODE were also detected by liquid chromatography-mass spectrometry. The contribution of the 7,8-LDS gene to M. oryzae pathogenicity was evaluated by replacement of the catalytic domain with hygromycin and green fluorescent protein variant (SGFP) cassettes. This genetically modified strain Delta 7,8-LDS infected rice leaves and roots and formed appressoria and conidia as the native fungus. The Delta 7,8-LDS mutant had lost the capacity to biosynthesize all the metabolites except small amounts of 8-hydroxylinoleic acid. Studies with stereospecifically deuterated linoleic acids showed that (8R)-HPODE was formed by abstraction of the pro-S hydrogen at C-8 and antarafacial oxygenation, whereas (7S,8S)-DiHODE and (8R,11S)-DiHODE were formed from (8R)-HPODE by suprafacial hydrogen abstraction and oxygenation at C-7 and C-11, respectively. A mac1 suppressor mutant (Delta mac1 sum1-99) of M. oryzae, which shows cAMP-independent protein kinase A activity, oxygenated 18:2n-6 to increased amounts of (10R)-HPODE and (5S,8R)-DiHODE. Expression of the 7,8-LDS gene but not of the second homologue was detected in the suppressor mutant. This suggests that PKA-mediated signaling pathway regulates the dioxygenase and hydroperoxide isomerase activities of M. oryzae.