11-hydroxy-12,13-epoxy-9-octadecenoic 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: 11-hydroxy-12,13-epoxy-9-octadecenoic acid
• 英文别名: (9Z)-11-hydroxy-12,13-epoxy-9-octadecenoic acid；(Z)-11-hydroxy-11-(3-pentyloxiran-2-yl)undec-9-enoic acid
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: UZCLYICSWADYGM-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  13(S)--过氧羟基-9,11-十八碳二烯酸 在 recombinant Ectocarpus siliculosus CYP₅₁₆₄B₁ enzyme 作用下， 以 aq. acetate buffer 为溶剂， 反应 0.25h， 生成 11-hydroxy-12,13-epoxy-9-octadecenoic acid
  参考文献：
  名称：

  Epoxyalcohol synthase of Ectocarpus siliculosus . First CYP74-related enzyme of oxylipin biosynthesis in brown algae

  摘要：

  Enzymes of CYP74 family play the central role in the biosynthesis of physiologically important oxylipins in land plants. Although a broad diversity of oxylipins is known in the algae, no CYP74s or related enzymes have been detected in brown algae yet. Cloning of the first CYP74-related gene CYP5164B1 of brown alga Ectocarpus siliculosus is reported in present work. The recombinant protein was incubated with several fatty acid hydroperoxides. Linoleic acid 9-hydroperoxide (9-HPOD) was the preferred substrate, while linoleate 13-hydroperoxide (13-HPOD) was less efficient. a.-Linolenic acid 9- and 13-hydroperoxides, as well as eicosapentaenoic acid 15-hydroperoxide were inefficient substrates. Both 9-HPOD and 13-HPOD were converted into epoxyalcohols. For instance, 9-HPOD was turned primarily into (9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid. Both epoxide and hydroxyl oxygen atoms of the epoxyalcohol were incorporated mostly from [O-18(2)]9-HPOD. Thus, the enzyme exhibits the activity of epoxyalcohol synthase (EsEAS). The results show that the EsEAS isomerizes the hydroperoxides into epoxyalcohols via epoxyallylic radical, a common intermediate of different CYP74s and related enzymes. EsEAS can be considered as an archaic prototype of CYP74 family enzymes. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbalip.2016.11.007

文献信息

• [EN] FATTY ACID DERIVATIVES AND THEIR USE<br/>[FR] DÉRIVÉS D'ACIDES GRAS ET UTILISATION ASSOCIÉE
  申请人：US HEALTH

  公开号：WO2019010414A1

  公开（公告）日：2019-01-10

  This disclosure concerns fatty acid derivatives, pharmaceutical compositions comprising the fatty acid derivatives, and methods of using the fatty acid derivatives, for example, to treat inflammation, chronic itch, chronic pain, an autoimmune disorder, atherosclerosis, a skin disorder, arthritis, a neurodegenerative disorder, or a psychiatric disorder in a subject. In some embodiments, the fatty acid derivative is a compound, or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, having a structure according to: (I) wherein X is from 1-16 carbons in length, Z is aliphatic from 1-16 carbons in length, or is not present, Y is selected from: (II) R1, R2, and R3 are independently hydrogen or lower alkyl, R4 is lower alkyl, hydroxyl, carboxyl, or amine, R5 is hydrogen, lower alkyl, or halide, R6 is hydroxyl or substituted thiol, and each R7 is independently hydrogen or fluoride or is not present and the adjacent carbons form alkyne.

  这份披露涉及脂肪酸衍生物，包括含有脂肪酸衍生物的药物组合物，以及使用脂肪酸衍生物的方法，例如用于治疗炎症、慢性瘙痒、慢性疼痛、自身免疫性疾病、动脉粥样硬化、皮肤疾病、关节炎、神经退行性疾病或精神疾病的主体。在某些实施例中，脂肪酸衍生物是一种化合物，或其立体异构体、互变异构体或药用可接受的盐，其结构如下：(I)其中X的长度为1-16个碳，Z是1-16个碳的脂肪族，或者不存在，Y选自：(II)R1、R2和R3独立地是氢或较低的烷基，R4是较低的烷基、羟基、羧基或胺基，R5是氢、较低的烷基或卤素，R6是羟基或取代硫醇，每个R7独立地是氢或氟或不存在，相邻的碳形成炔烃。
• Allene Oxide Synthase Pathway in Cereal Roots: Detection of Novel Oxylipin Graminoxins
  作者：Alexander N. Grechkin、Anna V. Ogorodnikova、Alevtina M. Egorova、Fakhima K. Mukhitova、Tatiana M. Ilyina、Bulat I. Khairutdinov

  DOI：10.1002/open.201800045

  日期：2018.5

  (9‐HPOD), and (9S,10E,12Z,15Z)‐9‐hydroperoxy‐10,12,15‐octadecatrienoic acid, respectively, via the corresponding allene oxides and cyclopropanones. The data indicate that conversion of the allene oxide into the cyclopropanone is controlled by soluble cyclase. The short‐lived cyclopropanones are hydrolyzed to products 1–3. The collective name “graminoxins” has been ascribed to oxylipins 1–3.

  小麦，大麦和高粱的年轻根以及茉莉酸甲酯预处理的水稻幼苗，经历了针对以前未知的磷脂1到3的空前的氧化烯合酶途径。这些Favorskii类制品，（4 Ž）-2-戊基-4-十三烯-1,13-二酸（1），（2' Ž）-2-（2'-辛烯基） -癸烷1,10-二酸（2），和（2' ž，5' ž）-2-（2'，5'-辛二烯） -癸烷-1,10-二酸（3），具有在侧链羧基功能，由他们的MS和NMR光谱数据揭示。化合物1 - 3是检测到的主要磷脂，以及相关的α-酮醇。产品13从（9生物合成Ž，11 ê，13小号）-13-氢过氧基9,11-十八碳二烯酸，（9小号，10 ê，12 Ž）-9-氧化氢-10,12-十八碳二烯酸（9‐HPOD）和（9 S，10 E，12 Z，15 Z）‐9‐氢过氧‐10,12,15‐十八碳三烯酸，分别通过相应的丙二烯氧化物和环丙烷酮。数据表明氧化烯到环氧丙烷的转化是由可溶性环化酶控制的。寿命短的环丙烷酮水解成产物1
• FATTY ACID DERIVATIVES AND THEIR USE
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary, Department of Health and Human servic

  公开号：US20210139440A1

  公开（公告）日：2021-05-13

  This disclosure concerns fatty acid derivatives, pharmaceutical compositions comprising the fatty acid derivatives, and methods of using the fatty acid derivatives, for example, to treat inflammation, chronic itch, chronic pain, an autoimmune disorder, atherosclerosis, a skin disorder, arthritis, a neurodegenerative disorder, or a psychiatric disorder in a subject. In some embodiments, the fatty acid derivative is a compound, or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, having a structure according to: wherein X is from 1-16 carbons in length, Z is aliphatic from 1-16 carbons in length, or is not present, Y is selected from: R 1 , R 2 , and R 3 are independently hydrogen or lower alkyl, R 4 is lower alkyl, hydroxyl, carboxyl, or amine, R 5 is hydrogen, lower alkyl, or halide, R 6 is hydroxyl or substituted thiol, and each R 7 is independently hydrogen or fluoride or is not present and the adjacent carbons form alkyne.
• Epoxyalcohol synthase of Ectocarpus siliculosus . First CYP74-related enzyme of oxylipin biosynthesis in brown algae
  作者：Yana Y. Toporkova、Valeria S. Fatykhova、Yuri V. Gogolev、Bulat I. Khairutdinov、Lucia S. Mukhtarova、Alexander N. Grechkin

  DOI：10.1016/j.bbalip.2016.11.007

  日期：2017.2

  Enzymes of CYP74 family play the central role in the biosynthesis of physiologically important oxylipins in land plants. Although a broad diversity of oxylipins is known in the algae, no CYP74s or related enzymes have been detected in brown algae yet. Cloning of the first CYP74-related gene CYP5164B1 of brown alga Ectocarpus siliculosus is reported in present work. The recombinant protein was incubated with several fatty acid hydroperoxides. Linoleic acid 9-hydroperoxide (9-HPOD) was the preferred substrate, while linoleate 13-hydroperoxide (13-HPOD) was less efficient. a.-Linolenic acid 9- and 13-hydroperoxides, as well as eicosapentaenoic acid 15-hydroperoxide were inefficient substrates. Both 9-HPOD and 13-HPOD were converted into epoxyalcohols. For instance, 9-HPOD was turned primarily into (9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid. Both epoxide and hydroxyl oxygen atoms of the epoxyalcohol were incorporated mostly from [O-18(2)]9-HPOD. Thus, the enzyme exhibits the activity of epoxyalcohol synthase (EsEAS). The results show that the EsEAS isomerizes the hydroperoxides into epoxyalcohols via epoxyallylic radical, a common intermediate of different CYP74s and related enzymes. EsEAS can be considered as an archaic prototype of CYP74 family enzymes. (C) 2016 Elsevier B.V. All rights reserved.