6R,8R-dihydroxy-9,12(Z,Z)-octadecadienoic 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: 6R,8R-dihydroxy-9,12(Z,Z)-octadecadienoic acid
• 英文别名: (6R,8R)-dihydroxy-9Z,12Z-octadecadienoic acid；6R,8R-dihydroxy-9Z,12Z-octadecadienoic acid；(6R,8R,9Z,12Z)-6,8-dihydroxyoctadeca-9,12-dienoic acid
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: JEJFTAIQLBEZLI-PIEIVNQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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

• 作为反应物：
  描述：

  6R,8R-dihydroxy-9,12(Z,Z)-octadecadienoic acid 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以4.2 mg的产率得到((4R,6R)-6-((1Z,4Z)-deca-1,4-dien-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)pentanoic acid
  参考文献：
  名称：

  来自红树林根际土壤真菌真菌Penicillium javanicum HK1-22的两种新的不饱和脂肪酸。

  摘要：

  两种新的不饱和脂肪酸，6 R，8 R-二羟基-9 Z，12 Z-十八碳二烯酸（1）和甲基-6 R，8 R-二羟基-9 Z，12 Z-十八碳二烯酸酯（2），和两种已知的不饱和脂肪酸9 ž，12 ž十八碳二烯酸的类似物（3，4）与已知的倍半萜类（一起5）从红树林根际土壤衍生的真菌分离青霉爪哇HK1-22。来自1的丙酮化物衍生物（1a）也准备好了。通过分析1a的1D和2D NOE光谱确定1的相对构型。的绝对构型1被分配了生物遗传因素的基础上。评价了高产率化合物5对四种农作物病原体菌株的抗真菌活性，并且显示了对所有测试菌株的显着抗真菌活性。

  DOI：

  10.1016/j.bioorg.2019.103331
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 Penicillium oxalicum KCTC 6440 6R,8R-linoleate diol synthase 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 6R,8R-dihydroxy-9,12(Z,Z)-octadecadienoic acid
  参考文献：
  名称：

  Molecular characterization of Penicillium oxalicum 6R,8R-linoleate diol synthase with new regiospecificity

  摘要：

  Diol synthase-derived metabolites are involved in the sexual and asexual life cycles of fungi. A putative diol synthase from Penicillium oxalicum was found to convert palmitoleic acid (16:1n-7), oleic acid (18:1n-9), linoleic acid (18:2n-6), and a-linolenic acid (18:3n-3) to 6S,8R-dihydroxy-9(Z)-hexadecenoic acid, 6R,8R-dihydroxy9(Z)-octadecenoic acid, 6R,8R-dihydroxy-9,12(Z,Z)-octadecadienoic acid, and 6S,8R-dihydroxy-9,12,15(Z,Z,Z)octadecatrienoic acid, respectively, which were identified by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and nuclear magnetic resonance (NMR) spectroscopy analyses. The specific activity and catalytic efficiency of P. oxalicum 6,8-diol synthase were the highest for 18:2n-6, indicating that the enzyme is a 6R,8Rlinoleate diol synthase (6R,8R-LDS) with new regiospecificity. This is the first report of a 6R,8R-LDS. LDS is a fusion protein consisting of a dioxygenase domain at the N-terminus and a cytochrome P450/hydroperoxide isomerase (P450/HPI) domain at the C-terminus. The putative active-site residues in the C-terminal domain of P. oxalicum 6R,8R-LDS were proposed based on a substrate-docking homology model. The results of the site-directed mutagenesis within C-terminal P450 domain suggested that Asn(886), Arg(707), and Arg(934), are catalytic importance and belong to the catalytic groove. Phe(794) and GIn(889) were found to be involved in the regiospecific rearrangement of hydroperoxide, while the F794E and Q889A variants of P. oxalicum 6,8-LDS acted as 7,8- and 8,11-LDSs, respectively. All these mutations critically affected the HPI activity of P. oxalicum 6R,8R-LDS.

  DOI：

  10.1016/j.bbalip.2018.10.006

文献信息

• Molecular characterization of Penicillium oxalicum 6R,8R-linoleate diol synthase with new regiospecificity
  作者：Min-Ju Seo、Woo-Ri Kang、Eun-Joo Yang、Kyung-Chul Shin、Yoon-Joo Ko、Deok-Kun Oh

  DOI：10.1016/j.bbalip.2018.10.006

  日期：2019.4

  Diol synthase-derived metabolites are involved in the sexual and asexual life cycles of fungi. A putative diol synthase from Penicillium oxalicum was found to convert palmitoleic acid (16:1n-7), oleic acid (18:1n-9), linoleic acid (18:2n-6), and a-linolenic acid (18:3n-3) to 6S,8R-dihydroxy-9(Z)-hexadecenoic acid, 6R,8R-dihydroxy9(Z)-octadecenoic acid, 6R,8R-dihydroxy-9,12(Z,Z)-octadecadienoic acid, and 6S,8R-dihydroxy-9,12,15(Z,Z,Z)octadecatrienoic acid, respectively, which were identified by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and nuclear magnetic resonance (NMR) spectroscopy analyses. The specific activity and catalytic efficiency of P. oxalicum 6,8-diol synthase were the highest for 18:2n-6, indicating that the enzyme is a 6R,8Rlinoleate diol synthase (6R,8R-LDS) with new regiospecificity. This is the first report of a 6R,8R-LDS. LDS is a fusion protein consisting of a dioxygenase domain at the N-terminus and a cytochrome P450/hydroperoxide isomerase (P450/HPI) domain at the C-terminus. The putative active-site residues in the C-terminal domain of P. oxalicum 6R,8R-LDS were proposed based on a substrate-docking homology model. The results of the site-directed mutagenesis within C-terminal P450 domain suggested that Asn(886), Arg(707), and Arg(934), are catalytic importance and belong to the catalytic groove. Phe(794) and GIn(889) were found to be involved in the regiospecific rearrangement of hydroperoxide, while the F794E and Q889A variants of P. oxalicum 6,8-LDS acted as 7,8- and 8,11-LDSs, respectively. All these mutations critically affected the HPI activity of P. oxalicum 6R,8R-LDS.
• Two new unsaturated fatty acids from the mangrove rhizosphere soil-derived fungus Penicillium javanicum HK1-22
  作者：Zhao-Yang Liang、Nan-Xing Shen、Yao-Yao Zheng、Jin-Tao Wu、Li Miao、Xiu-Mei Fu、Min Chen、Chang-Yun Wang

  DOI：10.1016/j.bioorg.2019.103331

  日期：2019.12

  Two new unsaturated fatty acids, 6R,8R-dihydroxy-9Z,12Z-octadecadienoic acid (1) and methyl-6R,8R-dihydroxy-9Z,12Z-octadecadienoate (2), and two known 9Z,12Z-octadecadienoic acid analogues (3, 4) together with a known sesquiterpenoid (5) were isolated from the mangrove rhizosphere soil-derived fungus Penicillium javanicum HK1-22. An acetonide derivative (1a) from 1 was also prepared. The relative configuration

  两种新的不饱和脂肪酸，6 R，8 R-二羟基-9 Z，12 Z-十八碳二烯酸（1）和甲基-6 R，8 R-二羟基-9 Z，12 Z-十八碳二烯酸酯（2），和两种已知的不饱和脂肪酸9 ž，12 ž十八碳二烯酸的类似物（3，4）与已知的倍半萜类（一起5）从红树林根际土壤衍生的真菌分离青霉爪哇HK1-22。来自1的丙酮化物衍生物（1a）也准备好了。通过分析1a的1D和2D NOE光谱确定1的相对构型。的绝对构型1被分配了生物遗传因素的基础上。评价了高产率化合物5对四种农作物病原体菌株的抗真菌活性，并且显示了对所有测试菌株的显着抗真菌活性。