15(R)-HETE

• 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: 15(R)-HETE
• 英文别名: (15R)-hydroxyeicosatetraenoic acid；15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid；(5Z,8Z,11Z,13E,15R)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: JSFATNQSLKRBCI-UDQWCNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  15(R)-HETE 在 5’-三磷酸腺苷 、 calcium chloride 、 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 (5S,15R)-5,15-dihydroxy-eicosa-6,8,11,13-tetraenoic acid
  参考文献：
  名称：

  Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2

  摘要：

  Biosynthesis of the prostaglandin endoperoxide by the cyclooxygenase (COX) enzymes is accompanied by formation of a small amount of 11R-hydroxyeicosatetraenoic acid (HETE), 15R-HETE, and 15S-HETE as by-products. Acetylation of COX-2 by aspirin abrogates prostaglandin synthesis and triggers formation of 15R-HETE as the sole product of oxygenation of arachidonic acid. Here, we investigated the formation of by-products of the transformation of 5S-HETE by native COX-2 and by aspirin-acetylated COX-2 using HPLC-ultraviolet, GC-MS, and LC-MS analysis. 5S,15S- dihydroxy (di)HETE, 5S,15R-diHETE, and 5S,11R-diHETE were identified as by-products of native COX-2, in addition to the previously described di-endoperoxide (5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid) as the major oxygenation product. 5S,15R-diHETE was the only product formed by aspirin-acetylated COX-2. Both 5,15-diHETE and 5,11-diHETE were detected in CT26 mouse colon carcinoma cells as well as in lipopolysaccharide-activated RAW264.7 cells incubated with 5S-HETE, and their formation was attenuated in the presence of the COX-2 specific inhibitor, NS-398. Aspirin-treated CT26 cells gave 5,15-diHETE as the most prominent product formed from 5S-HETE. 5S,15S-diHETE has been described as a product of the cross-over of 5-lipoxygenase (5-LOX) and 15-LOX activities in elicited rat mononuclear cells and human leukocytes, and our studies implicate crossover of the 5-LOX and COX-2 pathways as an additional bio-synthetic route.-Mulugeta, S., T. Suzuki, N. T. Hernandez, M. Griesser, W. E. Boeglin, and C. Schneider. Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2. J. Lipid Res. 2010. 51: 575-585.

  DOI：

  10.1194/jlr.m001719
• 作为产物：
  描述：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 Lindlar's catalyst 、 copper(l) iodide 、 四(三苯基膦)钯 喹啉 、 正丙胺 、 potassium fluoride 、 lithium hydroxide 、 jones reagent 、 氢气 、 氟化氢吡啶 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 2.0h， 生成 15(R)-HETE
  参考文献：
  名称：

  立体控制的（5 Z，8 Z 11 Z，13 E）（15 S）-15-hydroxyeicosa-5,8,11,13-丁烯酸（15 S -HETE）及其类似物的全合成

  摘要：

  描述了一种新颖且立体选择性的15 S -HETE和许多基于Cu I -Pd 0偶联反应的类似物的合成方法。

  DOI：

  10.1039/c39850001580

文献信息

• Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to <i>R</i>,<i>R</i>-dihydroxy fatty acids as lipid mediators using double-oxygenating 15<i>R</i>-lipoxygenase
  作者：Jin Lee、Yoon-Joo Ko、Jin-Byung Park、Deok-Kun Oh

  DOI：10.1039/d4gc00308j

  日期：——

  C20- and C22-dihydroxy fatty acids (DiHFAs) are bioactive lipid mediators (LMs) in humans.

  C20- 和 C22-二羟基脂肪酸（DiHFAs）是人体中具有生物活性的脂质介质（LMs）。
• Oils with anti-inflammatory activity containing natural specialized proresolving mediators and their precursors
  申请人：SOLUTEX NA LLC

  公开号：US10568858B2

  公开（公告）日：2020-02-25

  The present invention encompasses oils that have anti-inflammatory or resolution-stimulating activity that contain or are enriched with Specialized Proresolving Mediators (SPM) or SPM precursors, which originate from an oil obtained from organisms containing long chain omega-3 polyunsaturated fatty acids, such as fish, crustaceae, algae, and mollusks. The invention also encompasses a method for the production of these oils, and the utilization of the oils for nutritional supplements, pharmaceutical formulations, and cosmetic formulations, which can be employed for treating an inflammatory condition.

  本发明包括具有抗炎或刺激溶解活性的油类，这些油类含有或富含特化促溶解介质（SPM）或 SPM 前体，这些特化促溶解介质或 SPM 前体来源于从含有长链欧米加-3 多不饱和脂肪酸的生物（如鱼类、甲壳类、藻类和软体动物）中获得的油类。本发明还包括生产这些油的方法，以及将这些油用于营养补充剂、药物制剂和化妆品制剂的方法，这些制剂可用于治疗炎症。
• Oils with anti-inflammatory activity containing natural Specialized Proresolving Mediators and their precursors
  申请人：Solutex NA LLC

  公开号：US11077083B2

  公开（公告）日：2021-08-03

  The present invention encompasses oils that have anti-inflammatory or resolution-stimulating activity that contain or are enriched with Specialized Proresolving Mediators (SPM) or SPM precursors, which originate from an oil obtained from organisms containing long chain omega-3 polyunsaturated fatty acids, such as fish, crustaceae, algae, and mollusks. The invention also encompasses a method for the production of these oils, and the utilization of the oils for nutritional supplements, pharmaceutical formulations, and cosmetic formulations, which can be employed for treating an inflammatory condition.

  本发明包括具有抗炎或刺激溶解活性的油类，这些油类含有或富含特化促溶解介质（SPM）或 SPM 前体，这些特化促溶解介质或 SPM 前体来源于从含有长链欧米加-3 多不饱和脂肪酸的生物（如鱼类、甲壳类、藻类和软体动物）中获得的油类。本发明还包括生产这些油的方法，以及将这些油用于营养补充剂、药物制剂和化妆品制剂的方法，这些制剂可用于治疗炎症。
• Treatment of vulvar pain
  申请人：University of Rochester

  公开号：US11400057B2

  公开（公告）日：2022-08-02

  The present invention relates to methods of treating female reproductive tract irritation (such as pain and pruritus) or/and inflammation.

  本发明涉及治疗女性生殖道刺激（如疼痛和瘙痒）或/和炎症的方法。
• Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
  作者：Aldwin Anterola、Cornelia Göbel、Ellen Hornung、George Sellhorn、Ivo Feussner、Howard Grimes

  DOI：10.1016/j.phytochem.2008.11.012

  日期：2009.1

  Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 alpha-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering plants. To identify the fatty acid substrates used by moss lipoxygenases, eight lipoxygenase genes from Physcomitrella patens were heterologously expressed in Escherichia coli, and then analyzed for lipoxygenase activity using linoleic, alpha-linolenic and arachidonic acids as substrates. Among the eight moss lipoxygenases, only seven were found to be enzymatically active in vitro, two of which selectively used arachidonic acid as the substrate, while the other five preferred alpha-linolenic acid. Based on enzyme assays using a Clark-type oxygen electrode, all of the active lipoxygenases had an optimum pH at 7.0, except for one with highest activity at pH 5.0. HPLC analyses indicated that the two arachidonic acid lipoxygenases form (12S)-hydroperoxy eicosatetraenoic acid as the main product, while the other five lipoxygenases produce mainly (13S)-hydroperoxy octadecatrienoic acid from alpha-linolenic acid. These results suggest that mosses may have both C20 and C18 based oxylipin pathways. Published by Elsevier Ltd.