(ω5Z)-etherolenic 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: (ω5Z)-etherolenic acid
• 英文别名: (9Z,11E,1'Z,3'Z)-12-(1',3'-hexadienyloxy)-9,11-dodecadienoic acid；(9Z,11E)-12-[(1Z,3Z)-hexa-1,3-dienoxy]dodeca-9,11-dienoic acid
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: QWRJRLCIDLDGLM-YKZXWFTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-O-(ω5Z)-etherolenoyl-2-O-α-linolenoyl-3-O-(α-galactopyranosyl-1-6-β-D-galactopyranosyl)-sn-glycerol 在 Rhizopus arrhizus lipase 作用下， 生成 (ω5Z)-etherolenic acid
  参考文献：
  名称：

  Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves

  摘要：

  Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linolipins occurred in the injured leaves of meadow buttercup, while intact leaves possessed no linolipins. These oxylipins were isolated from the injured leaves, separated and purified by HPLC. The structural analyses of linolipins by UV, mass-spectroscopy and NMR spectroscopy resulted in the identification of eight molecular species. Three of them were identical to linolipins B-D found earlier in the leaves of flax (Linum usitatissimum L.). Other molecular species were identified as 1-O-(omega 5Z)-etherolenoyl-2-O-dinor-(omega 5Z)-etherolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z,10Z,13Z)-hexadecatrienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z, 10Z)-hexadecadienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-0-(omega 5Z)-etherolenoyl-2-O-alpha-linolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, and 1-O-(omega 5Z)-etherolenoyl-2-O-palmitoyl-3-O-(alpha-galactopyranosyl-1-6-beta-D-galactopyranosyl)-sn-glycerol. The trivial names "linolipins E, F, G, H and I," respectively, have been ascribed to these novel complex oxylipins.

  DOI：

  10.1016/j.phytochem.2018.10.030

文献信息

• The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
  作者：Yana Y. Toporkova、Elena O. Smirnova、Tatiana M. Iljina、Lucia S. Mukhtarova、Svetlana S. Gorina、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2020.112512

  日期：2020.11

  The CYP74 family of cytochromes P450 includes four enzymes of fatty acid hydroperoxide metabolism: allene oxide synthase (AOS), hydroperoxide lyase (HPL), divinyl ether synthase (DES), and epoxyalcohol synthase (EAS). The present work is concerned with catalytic specificities of three recombinant DESs, namely, the 9-DES (LeDES, CYP74D1) of tomato (Solanum lycopersicum), 9-DES (NtDES, CYP74D3) of tobacco

  CYP74 细胞色素 P450 家族包括四种脂肪酸氢过氧化物代谢酶：丙二烯氧化合酶 (AOS)、氢过氧化物裂解酶 (HPL)、二乙烯基醚合酶 (DES) 和环氧醇合酶 (EAS)。目前的工作涉及三种重组 DES 的催化特异性，即番茄 (Solanum lycopersicum) 的 9-DES (LeDES, CYP74D1)、烟草 (Nicotiana tabacum) 的 9-DES (NtDES, CYP74D3) 和 13-DES (LuDES, CYP74B16) 亚麻 (Linum usitatissimum)，以及它们对定点诱变的改变。LeDES 和 NtDES 都将亚油酸和 α-亚麻酸的 9-氢过氧化物转化为二乙烯基醚 colleneic 和 colnelenic 酸（分别），只有少数 HPL 和 EAS 产物。相比之下，LeDES 和 NtDES 对亚油酸 13-过氧化氢
• A lipoxygenase-divinyl ether synthase pathway in flax (Linum usitatissimum L.) leaves
  作者：Ivan R. Chechetkin、Alexander Blufard、Mats Hamberg、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2008.04.012

  日期：2008.7

  Incubation of linoleic acid with an enzyme preparation from leaves of flax (Linum usitatissimum L.) led to the formation of a divinyl ether fatty acid, i.e. (9Z,11E,1'Z)-12-(1'-hexenyloxy)-9,11-dodecadienoic [(omega5Z)-etheroleic] acid, as well as smaller amounts of 13-hydroxy-9(Z),11(E)-octadecadienoic acid. The 13-hydroperoxide of linoleic acid afforded the same set of products, whereas incubations

  亚油酸与来自亚麻 (Linum usitatissimum L.) 叶的酶制剂一起孵育导致形成二乙烯基醚脂肪酸，即 (9Z,11E,1'Z)-12-(1'-己烯氧基)-9 ,11-dodecadienoic [(omega5Z)-etheroleic] 酸，以及少量的 13-hydroxy-9(Z),11(E)-octadecadienoic acid。亚油酸的 13-氢过氧化物提供了相同的产物，而 α-亚麻酸及其 13-氢过氧化物的孵育提供了二乙烯基醚 (9Z,11E,1'Z,3'Z)-12-(1', 3'-己二烯氧基)-9,11-十二碳二烯酸[(omega5Z)-etherolenic]作为主要产物。两种二乙烯基醚的鉴定均由它们的 UV、质量、(1)H NMR 和 COZY 光谱数据证实。除了这些结果证明的 13-脂肪氧化酶和二乙烯基醚合酶活性外，
• Detection and molecular cloning of CYP74Q1 gene: Identification of Ranunculus acris leaf divinyl ether synthase
  作者：Svetlana S. Gorina、Yana Y. Toporkova、Lucia S. Mukhtarova、Ivan R. Chechetkin、Bulat I. Khairutdinov、Yuri V. Gogolev、Alexander N. Grechkin

  DOI：10.1016/j.bbalip.2014.05.005

  日期：2014.9

  Enzymes of the CYP74 family, including the divinyl ether synthase (DES), play important roles in plant cell signalling and defence. The potent DES activities have been detected before in the leaves of the meadow buttercup (Ranunculus acris L.) and few other Ranunculaceae species. The nature of these DESs and their genes remained unrevealed. The PCR with degenerate primers enabled to detect the transcript of unknown P450 gene assigned as CYP74Q1. Besides, two more CYP74Q1 isoforms with minimal sequence variations have been found. The full length recombinant CYP74Q1 protein was expressed in Escherichia coli. The preferred substrates of this enzyme are the 13-hydroperoxides of alpha-linolenic and linoleic acids, which are converted to the divinyl ether oxylipins (omega 5Z)-etherolenic acid, (9Z,11E)-12-[(1'Z,3'Z)-hexadienyloxy]-9,11-dodecadienoic acid, and (omega 5Z)-etheroleic acid, (9Z,11E)-12-[(1'Z)-hexenyloxy]-9,11-dodecadienoic acid, respectively, as revealed by the data of mass spectrometry, NMR and UV spectroscopy. Thus, CYP74Q1 protein was identified as the R. acris DES (RaDES), a novel DES type and the opening member of new CYP74Q subfamily. (C) 2014 Elsevier B.V. All rights reserved.
• Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves
  作者：Ivan R. Chechetkin、Alexander S. Blufard、Andrey Y. Yarin、Evgenia O. Fedina、Bulat I. Khairutdinov、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2018.10.030

  日期：2019.1

  Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linolipins occurred in the injured leaves of meadow buttercup, while intact leaves possessed no linolipins. These oxylipins were isolated from the injured leaves, separated and purified by HPLC. The structural analyses of linolipins by UV, mass-spectroscopy and NMR spectroscopy resulted in the identification of eight molecular species. Three of them were identical to linolipins B-D found earlier in the leaves of flax (Linum usitatissimum L.). Other molecular species were identified as 1-O-(omega 5Z)-etherolenoyl-2-O-dinor-(omega 5Z)-etherolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z,10Z,13Z)-hexadecatrienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z, 10Z)-hexadecadienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-0-(omega 5Z)-etherolenoyl-2-O-alpha-linolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, and 1-O-(omega 5Z)-etherolenoyl-2-O-palmitoyl-3-O-(alpha-galactopyranosyl-1-6-beta-D-galactopyranosyl)-sn-glycerol. The trivial names "linolipins E, F, G, H and I," respectively, have been ascribed to these novel complex oxylipins.