(14Z)-hexadecenoyl-CoA(4-)

• 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: (14Z)-hexadecenoyl-CoA(4-)
• 英文别名: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[(3R)-4-[[3-[2-[(Z)-hexadec-14-enoyl]sulfanylethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] phosphate
• 化学式: C37H60N7O17P3S-4
• 分子量: 999.9
• InChiKey: HIHIIKWURVKNRP-CTCHSOFBSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  65
• 可旋转键数：
  32
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  400
• 氢给体数：
  5
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  铁燧石 、 氢(+1)阳离子 、 hexadecanoyl CoA 、 氧气 生成 (14Z)-hexadecenoyl-CoA(4-) 、 铁阳离子 、 水
  参考文献：
  名称：

  Evolution of moth sex pheromones via ancestral genes

  摘要：

  大多数蛾类物种的配偶选择都涉及到雌性释放的性信息素的远距离信号传递。在鳞翅目中使用的信息素结构具有很大的多样性，即使在密切相关的物种中也是如此。难题在于如何发生信号分歧。由于混合物组成和响应偏好具有强烈的标准化选择压力，因此通过小的适应性变化转向不同结构的信息素是不可能的。在这里，我们提供支持假说的数据，即通过激活信息素腺中存在的非功能性脱饱和酶基因转录本，发生了一个主要的信息素转变。我们还证明了存在对新信息素混合物有反应的罕见雄性。他们的存在将允许对新混合物的雄性反应进行非对称跟踪，从而进化出具有结构不同的性信息素成分的 Ostrinia 物种。

  DOI：

  10.1073/pnas.152445399

文献信息

• Novel sex pheromone desaturases in the genomes of corn borers generated through gene duplication and retroposon fusion
  作者：Bingye Xue、Alejandro P. Rooney、Masaki Kajikawa、Norihiro Okada、Wendell L. Roelofs

  DOI：10.1073/pnas.0700422104

  日期：2007.3.13

  The biosynthesis of female moth sex pheromone blends is controlled by a number of different enzymes, many of which are encoded by members of multigene families. One such multigene family, the acyl-CoA desaturases, is composed of certain genes that function as key players in moth sex pheromone biosynthesis. Although much is known regarding the function of some of these genes, very little is known regarding how novel genes have evolved within this family and how this might impact the establishment of new sex pheromone blends within a species. We have discovered that several cryptic Δ11 and Δ14 desaturase genes exist in the genomes of the European and Asian corn borers ( Ostrinia nubilalis and Ostrinia furnacalis , respectively). Furthermore, an entirely novel class of desaturase gene has arisen in the Ostrinia lineage and is derived from duplication of the Δ11 desaturase gene and subsequent fusion with a retroposon. Interestingly, the genes have been maintained over relatively long evolutionary time periods in corn borer genomes, and they have not been recognizably pseudogenized, suggesting that they maintain functional integrity. The existence of cryptic desaturase genes in moth genomes indicates that the evolution of moth sex pheromone desaturases in general is much more complex than previously recognized.

  雌蛾性信息素混合物的生物合成由许多不同的酶控制，其中许多是由多基因家族成员编码的。其中一个这样的多基因家族是酰基辅酶A脱饱和酶，由某些基因组成，这些基因在蛾类性信息素生物合成中发挥关键作用。虽然对其中一些基因的功能已知甚多，但对于如何在这个家族中演化新的基因以及这如何影响物种内新性信息素混合物的建立，知之甚少。我们发现欧洲玉米螟（Ostrinia nubilalis）和亚洲玉米螟（Ostrinia furnacalis）的基因组中存在几个隐蔽的Δ11和Δ14脱饱和酶基因。此外，一种全新的脱饱和酶基因类别已在Ostrinia谱系中出现，并源于Δ11脱饱和酶基因的复制以及随后与逆转座子的融合。有趣的是，这些基因在玉米螟基因组中已经维持了相对较长的演化时间，并且它们没有明显的赝基因化，表明它们保持了功能完整性。蛾基因组中隐蔽的脱饱和酶基因的存在表明，蛾类性信息素脱饱和酶的演化总体上比以前认为的要复杂得多。
• Alternative suppression of transcription from two desaturase genes is the key for species-specific sex pheromone biosynthesis in two Ostrinia moths
  作者：Ryota Sakai、Mai Fukuzawa、Ryo Nakano、Sadahiro Tatsuki、Yukio Ishikawa

  DOI：10.1016/j.ibmb.2008.10.001

  日期：2009.1

  Crossing of two Ostrinia moths that use different positional isomers as sex pheromone components revealed that species-specific pheromone is produced through alternative suppression of two pheromone gland-specific desaturases at the gene transcription level. The sex pheromone of Ostrinia scapulalis (the adzuki bean borer) is a blend of (Z)-11- and (E)-11-tetradecenyl acetates (Z/E11-14:OAc), whereas that of Ostrinia furnacalis (the Asian corn borer) is a blend of (Z)-12- and (E)-12-tetradecenyl acetates (Z/E12-14:OAc). Delta 11-Desaturase is known to be involved in the biosynthesis of Z/E11-14:OAc, and Delta 14-desaturase, in that of Z/E12-14:OAc. The F1 hybrid between O. scapulalis and O. furnacalis produced both parents' sex pheromone components (Z/E11-14:OAc and Z/E12-14:OAc). Although the two species have both Delta 11- and Delta 14-desaturase genes, transcription from the Delta 14-desaturase gene was strongly suppressed in O. scapulalis, as was transcription from the All-desaturase gene in O. furnacalis. Meanwhile, both genes were transcribed into mRNA in F1. The production/non-production of Z/E11-14:OAc and Z/E12-14:OAc in F1, F2, and backcross progenies could be explained by an autosomal locus that suppresses transcription from either the Delta 11-desaturase or Delta 14-desaturase gene. Based on the findings, the evolution of sex pheromone biosynthesis in O. scapulalis and O. fumacalis is discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Evolution of moth sex pheromones via ancestral genes
  作者：Wendell L. Roelofs、Weitian Liu、Guixia Hao、Hongmei Jiao、Alejandro P. Rooney、Charles E. Linn

  DOI：10.1073/pnas.152445399

  日期：2002.10.15

  Mate finding in most moth species involves long-distance signaling via female-emitted sex pheromones. There is a great diversity of pheromone structures used throughout the Lepidoptera, even among closely related species. The conundrum is how signal divergence has occurred. With strong normalizing selection pressure on blend composition and response preferences, it is improbable that shifts to pheromones of diverse structures occur through adaptive changes in small steps. Here, we present data supporting the hypothesis that a major shift in the pheromone of an Ostrinia species occurred by activation of a nonfunctional desaturase gene transcript present in the pheromone gland. We also demonstrate the existence of rare males that respond to the new pheromone blend. Their presence would allow for asymmetric tracking of male response to the new blend and, thus, evolution of an Ostrinia species with structurally different sex pheromone components.

  大多数蛾类物种的配偶选择都涉及到雌性释放的性信息素的远距离信号传递。在鳞翅目中使用的信息素结构具有很大的多样性，即使在密切相关的物种中也是如此。难题在于如何发生信号分歧。由于混合物组成和响应偏好具有强烈的标准化选择压力，因此通过小的适应性变化转向不同结构的信息素是不可能的。在这里，我们提供支持假说的数据，即通过激活信息素腺中存在的非功能性脱饱和酶基因转录本，发生了一个主要的信息素转变。我们还证明了存在对新信息素混合物有反应的罕见雄性。他们的存在将允许对新混合物的雄性反应进行非对称跟踪，从而进化出具有结构不同的性信息素成分的 Ostrinia 物种。