2-(3,4-dihydroxyphenyl)ethyl cis-5,8,11,14,17-eicosapentaenoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3,4-dihydroxyphenyl)ethyl cis-5,8,11,14,17-eicosapentaenoate
• 英文别名: hydroxytyrosyl eicosapentaenoate；N-eicosapentaenoyl dopamine；EPDA；2-(3,4-dihydroxyphenyl) ethyl eicosapentanoate；2-(3,4-dihydroxyphenyl)ethyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• 化学式: C₂₈H₃₈O₄
• 分子量: 438.607
• InChiKey: SEZXNZWEIWRDMQ-JLNKQSITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  全顺式二十碳五烯酸 、 羟基酪醇 在 immobilized lipase from Candida antarctica B 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 24.0h， 生成 2-(3,4-dihydroxyphenyl)ethyl cis-5,8,11,14,17-eicosapentaenoate
  参考文献：
  名称：

  Lipase-Produced Hydroxytyrosyl Eicosapentaenoate is an Excellent Antioxidant for the Stabilization of Omega-3 Bulk Oils, Emulsions and Microcapsules

  摘要：

  在本研究中，采用来自南极酵母B的固定化脂肪酶酶法制备了几种亲脂性羟基酪醇酯。氧化测试表明，这些结合物在脂质基质中表现出优异的抗氧化性能，其中羟基酪醇二十烯酸酯展现出最高的抗氧化活性。羟基酪醇二十烯酸酯有效稳定了大宗鱼油、鱼油水乳液和微胶囊鱼油。该抗氧化剂的稳定作用可能是因为它与油中的 omega-3 脂肪酸排列在一起，从而保护它们免受氧化，或者是因为这种不稳定的脂肪酸能够优先氧化，从而提供额外的抗氧化保护机制。羟基酪醇二十烯酸酯在 -20 °C 存储时本身稳定性可达一年。

  DOI：

  10.3390/molecules23020275

文献信息

• N-Eicosapentaenoyl Dopamine, A Conjugate of Dopamine and Eicosapentaenoic Acid (EPA), Exerts Anti-inflammatory Properties in Mouse and Human Macrophages
  作者：Giuseppina Augimeri、Pierluigi Plastina、Giulia Gionfriddo、Daniela Rovito、Cinzia Giordano、Alessia Fazio、Ines Barone、Stefania Catalano、Sebastiano Andò、Daniela Bonofiglio、Jocelijn Meijerink、Renger Witkamp

  DOI：10.3390/nu11092247

  日期：——

  A large body of evidence suggests that dietary n-3 polyunsaturated fatty acids (PUFAs), including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), contribute to a reduced inflammatory tone thereby lowering the risk for several chronic and degenerative diseases. Different mechanisms have been proposed to explain these anti-inflammatory effects, including those involving endocannabinoids and endocannabinoid-like molecules. In this context, fatty acid amides (FAAs), conjugates of fatty acids with amines or amino acids, are an emerging class of compounds. Dopamine conjugates of DHA (N-docosahexaenoyl dopamine, DHDA) and EPA (N-eicosapentaenoyl dopamine, EPDA) have previously been shown to induce autophagy, apoptosis, and cell death in different tumor lines. Additionally, DHDA has displayed anti-inflammatory properties in vitro. Here, we tested the immune-modulatory properties of EPDA in mouse RAW 264.7 and human THP-1 macrophages stimulated with lipopolysaccharide (LPS). EPDA suppressed the production of monocyte chemoattractant protein-1 (MCP-1), and interleukin-6 (IL-6) in both cell lines, and nitric oxide (NO), and macrophage-inflammatory protein-3α (MIP3A) in RAW 264.7 macrophages. At a transcriptional level, EPDA attenuated cyclooxygenase-2 (COX-2) expression in both cell lines and that of MCP-1, IL-6, and interleukin-1β (IL-1β) in THP-1 macrophages. Although further research is needed to reveal whether EPDA is an endogenous metabolite, our data suggest that this EPA-derived conjugate possesses interesting immune-modulating properties.

  大量证据表明，膳食中的n-3多不饱和脂肪酸（PUFAs），包括二十碳五烯酸（EPA）和二十二碳六烯酸（DHA），有助于降低炎症水平，从而降低患多种慢性和退行性疾病的风险。已提出了不同的机制来解释这些抗炎作用，包括涉及内源大麻素和类大麻素的机制。在这种背景下，脂肪酸酰胺（FAAs），即脂肪酸与胺或氨基酸结合的共轭物，是一类新兴的化合物。已经显示二十二碳六烯酸（DHA）的多巴胺共轭物（N-二十二碳六烯酰多巴胺，DHDA）和二十碳五烯酸（EPA）的多巴胺共轭物（N-二十碳五烯酰多巴胺，EPDA）能够诱导不同肿瘤细胞系中的自噬、凋亡和细胞死亡。此外，DHDA在体外显示出抗炎特性。在这里，我们测试了EPDA在用脂多糖（LPS）刺激的小鼠RAW 264.7和人类THP-1巨噬细胞中的免疫调节特性。EPDA抑制了这两种细胞系中单核细胞趋化蛋白-1（MCP-1）和白细胞介素-6（IL-6）的产生，以及RAW 264.7巨噬细胞中的一氧化氮（NO）和巨噬细胞炎症蛋白-3α（MIP3A）的产生。在转录水平上，EPDA减弱了这两种细胞系中环氧合酶-2（COX-2）的表达，以及THP-1巨噬细胞中MCP-1、IL-6和白细胞介素-1β（IL-1β）的表达。尽管需要进一步研究来揭示EPDA是否为内源代谢物，但我们的数据表明，这种源自EPA的共轭物具有有趣的免疫调节特性。
• Efficient lipase-catalyzed synthesis of new lipid antioxidants based on a catechol structure
  作者：A. Torres de Pinedo、P. Peñalver、D. Rondón、J.C. Morales

  DOI：10.1016/j.tet.2005.05.100

  日期：2005.8

  Lipid antioxidants phenolic saturated fatty acid esters were synthesized in high yields and short reaction times using the corresponding ethyl fatty acid esters, lipase from Candida Antarctica, vacuum and no solvent. Phenolic esters with mono- and polyunsaturated fatty acids (EPA and DHA) were also prepared. (c) 2005 Elsevier Ltd. All rights reserved.
• HYDROXYTYROSOL AND OLEUROPEIN COMPOSITIONS FOR INDUCTION OF DNA DAMAGE, CELL DEATH AND LSD1 INHIBITION
  申请人：McCord Darlene E.

  公开号：US20150342903A1

  公开（公告）日：2015-12-03

  Compositions comprising hydroxytyrosol-containing formulations and treatment regiments comprising hydroxytyrosol and/or oleuropein and chemotherapeutic agents are disclosed. Compositions and/or regiments may optionally include the administration of vitamins, minerals, and anti-oxidants. Methods for using these compositions and treatment regimens for treating subjects for diseases, such as a malignancy, and for inducing or enhancing angiogenesis, treating or preventing oxidative stress, for treating or preventing high glucose-induced dysfunction, treating or preventing chemotherapy-induced dysfunction, and for improving cell viability are provided. Various methods for use of the hydroxytyrosol compositions for inhibition of lysine specific demethylase 1 (LSD1) in various cancers are also provided.
• US9662302B2
  申请人：——

  公开号：US9662302B2

  公开（公告）日：2017-05-30