(9Z,12Z,15Z)-N-(2,3-dihydroxypropyl)octadeca-9,12,15-trienamide | 1024589-97-6

• 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: (9Z,12Z,15Z)-N-(2,3-dihydroxypropyl)octadeca-9,12,15-trienamide
• CAS: 1024589-97-6
• 化学式: C₂₁H₃₇NO₃
• 分子量: 351.53
• InChiKey: BHTKFCKCINKOAG-PDBXOOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9Z,12Z,15Z)-N-(2,3-dihydroxypropyl)octadeca-9,12,15-trienamide 在 sodium chloride 、 Physcomitrella patens allene oxide cyclase 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以24%的产率得到N-(2,3-dihydroxypropyl)-8-((1S,5S)-4-oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)octanamide
  参考文献：
  名称：

  验证产生 (+)-cis-12-Oxo-phytodienoic 酸的体外酶促反应的多功能性

  摘要：

  茉莉酸 (JA) 是一种植物激素，参与对昆虫和真菌的防御反应。JA 通过植物中的十八烷酸途径从 α-亚麻酸 (LA) 合成。12-氧代-植物二烯酸 (OPDA) 是该途径中的生物合成中间体之一。所报道的顺式-(+)-OPDA立体选择性全合成不是很有效，因为该反应涉及许多步骤以及使用水敏反应。因此，我们开发了一种使用亚麻籽的丙酮粉末和来自Physcomitrella patens 的丙二烯氧化环化酶 (PpAOC2) 合成 OPDA 的酶促方法。从这种方法，自然顺-(+)-OPDA 可以以大约 40% 的高产率合成。在这项研究中，我们研究了其他 OPDA 类似物的酶促合成的底物特异性，依次提供 OPDA 氨基酸缀合物、dinor-OPDA (dn-OPDA) 和 OPDA 单甘油酯，并表明阿拉伯糖苷的生物合成途径可以通过 MGDG 发生。

  DOI：

  10.1016/j.bmcl.2021.128284
• 作为产物：
  描述：

  3-氨基-1,2-丙二醇 、 Γ-十八碳三烯酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 13.0h， 生成 (9Z,12Z,15Z)-N-(2,3-dihydroxypropyl)octadeca-9,12,15-trienamide
  参考文献：
  名称：

  Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads

  摘要：

  A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1 beta, IL-6, and TNF-alpha) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-gamma-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 similar to 2 mu M). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1 beta, IL-6, and TNF-alpha) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.046

文献信息

• Isolation and Structure Determination of <i>cis</i>-OPDA-α-Monoglyceride from <i>Arabidopsis thaliana</i>
  作者：Shotaro Hirota、Yusuke Ito、Shiro Inoue、Naoki Kitaoka、Tohru Taniguchi、Kenji Monde、Kosaku Takahashi、Hideyuki Matsuura

  DOI：10.1021/acs.jnatprod.3c01237

  日期：——

  cis-12-oxo-Phytodieneoic acid-α-monoglyceride (1) was isolated from Arabidopsis thaliana. The chemical structure of 1 was elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by FDMS and HRFDMS data. The absolute configuration of the cis-OPDA moiety in 1 was determined by comparison of 1H NMR spectra and ECD measurements. With respect to the absolute configuration of

  顺式-12-氧代-植物二烯酸-α-单甘油酯( 1 )是从拟南芥中分离出来的。 1的化学结构是基于详尽的 1D 和 2D NMR 光谱测量并得到 FDMS 和 HRFDMS 数据的支持而阐明的。 1中顺式-OPDA 部分的绝对构型通过比较1 H NMR 谱和 ECD 测量来确定。关于甘油主链β位的绝对构型，通过与( R )-(+)-α-甲氧基-制备酯键衍生物来确定( S )与( R )的2:3比例。 α-三氟甲基苯乙酰氯并比较1 H NMR 谱。创伤应激不会增加1的内源水平，并且表明1对拟南芥发芽后生长具有抑制作用。值得注意的是，完整植物中1的内源量高于(+)-7-异茉莉酸和(+)-顺式-OPDA的量。 1还表现出对革兰氏阳性菌的抗菌活性，但茉莉酸却没有。还发现α-亚麻酸-α-单甘油酯在拟南芥植物中转化为1 ，这表明α-亚麻酸-α-单甘油酯是1的生物合成中间体。
• Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid
  作者：Yusuke Ito、Kento Sasaki、Tsuyoshi Ogihara、Naoki Kitaoka、Kosaku Takahahi、Hideyuki Matsuura

  DOI：10.1016/j.bmcl.2021.128284

  日期：2021.10

  the biosynthetic intermediates in this pathway. The reported stereo selective total synthesis of cis-(+)-OPDA is not very efficient due to the many steps involved in the reaction as well as the use of water sensitive reactions. Therefore, we developed an enzymatic method for the synthesis of OPDA using acetone powder of flax seed and allene oxide cyclase (PpAOC2) from Physcomitrella patens. From this

  茉莉酸 (JA) 是一种植物激素，参与对昆虫和真菌的防御反应。JA 通过植物中的十八烷酸途径从 α-亚麻酸 (LA) 合成。12-氧代-植物二烯酸 (OPDA) 是该途径中的生物合成中间体之一。所报道的顺式-(+)-OPDA立体选择性全合成不是很有效，因为该反应涉及许多步骤以及使用水敏反应。因此，我们开发了一种使用亚麻籽的丙酮粉末和来自Physcomitrella patens 的丙二烯氧化环化酶 (PpAOC2) 合成 OPDA 的酶促方法。从这种方法，自然顺-(+)-OPDA 可以以大约 40% 的高产率合成。在这项研究中，我们研究了其他 OPDA 类似物的酶促合成的底物特异性，依次提供 OPDA 氨基酸缀合物、dinor-OPDA (dn-OPDA) 和 OPDA 单甘油酯，并表明阿拉伯糖苷的生物合成途径可以通过 MGDG 发生。
• Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
  作者：Hung The Dang、Gyeoung Jin Kang、Eun Sook Yoo、Jongki Hong、Jae Sue Choi、Hyung Sik Kim、Hae Young Chung、Jee H. Jung

  DOI：10.1016/j.bmc.2010.12.046

  日期：2011.2

  A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1 beta, IL-6, and TNF-alpha) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-gamma-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 similar to 2 mu M). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1 beta, IL-6, and TNF-alpha) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads. (C) 2010 Elsevier Ltd. All rights reserved.