sesquisabinene A

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: sesquisabinene A
• 英文别名: sesquisabinene B；(1R,5R)-1-[(2S)-6-methylhept-5-en-2-yl]-4-methylidenebicyclo[3.1.0]hexane
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: DYUSFBWNOCHOFP-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  farnesyl pyrophosphate 生成 pyrophosphoric acid 、 sesquisabinene A
  参考文献：
  名称：

  The Variability of Sesquiterpenes Emitted from Two Zea mays Cultivars Is Controlled by Allelic Variation of Two Terpene Synthase Genes Encoding Stereoselective Multiple Product Enzymes

  摘要：

  玉米成熟叶片和果壳在开花后释放出一种复杂的萜烯挥发物混合物，主要由红没药烷、倍半萜烷和佛手柑烷类倍半萜组成。B73和Delprim这两个品种释放的挥发物成分相同，但比例明显不同。为了研究控制这些品种中萜烯多样性和分布的分子遗传和生化机制，我们从这两个品种中分离出了密切相关的萜烯合成酶基因terpene synthase4（tps4）和tps5。编码的酶TPS4和TPS5分别从前体法呢基二磷酸形成相同的倍半萜混合物，但产物比例不同。这些混合物分别对应于在B73和Delprim品种中观察到的倍半萜混合物。TPS4和TPS5在立体选择性上的差异是由四个氨基酸取代决定的，其中最重要的是在酶催化位点第409位由甘氨酸取代了丙氨酸残基。虽然这两个品种都含有tps4和tps5等位基因，但它们在萜烯组成上的差异是由于B73只有一个tps4的功能等位基因，而没有tps5的功能等位基因，而Delprim只有一个tps5的功能等位基因，而没有tps4的功能等位基因。功能缺失是由于移码突变或氨基酸取代导致其编码蛋白活性大大降低。因此，这两个玉米栽培品种

  DOI：

  10.1105/tpc.019877

文献信息

• Isotope sensitive branching and kinetic isotope effects to analyse multiproduct terpenoid synthases from Zea mays
  作者：Nathalie Gatto、Abith Vattekkatte、Tobias Köllner、Jörg Degenhardt、Jonathan Gershenzon、Wilhelm Boland

  DOI：10.1039/c4cc10395e

  日期：——

  Deuterium surrounded carbocations support branching point analyses of multi product terpenoid synthases.

  氘包围的碳正离子支持多产物萜类合酶的分支点分析。
• The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores
  作者：Christiane Schnee、Tobias G. Köllner、Matthias Held、Ted C. J. Turlings、Jonathan Gershenzon、Jörg Degenhardt

  DOI：10.1073/pnas.0508027103

  日期：2006.1.24

  Plants can defend themselves against herbivores by attracting natural enemies of the herbivores. The cues for attraction are often complex mixtures of herbivore-induced plant volatiles, making it difficult to demonstrate the role of specific compounds. After herbivory by lepidopteran larvae, maize releases a mixture of volatiles that is highly attractive to females of various parasitic wasp species. We identified the terpene synthase TPS10 that forms ( E )-β-farnesene, ( E )-α-bergamotene, and other herbivory-induced sesquiterpene hydrocarbons from the substrate farnesyl diphosphate. The corresponding gene is expressed in response to herbivore attack and is regulated at the transcript level. Overexpression of tps10 in Arabidopsis thaliana resulted in plants emitting high quantities of TPS10 sesquiterpene products identical to those released by maize. Using these transgenic Arabidopsis plants as odor sources in olfactometer assays showed that females of the parasitoid Cotesia marginiventris learn to exploit the TPS10 sesquiterpenes to locate their lepidopteran hosts after prior exposure to these volatiles in association with hosts. This dissection of the herbivore-induced volatile blend demonstrates that a single gene such as tps10 can be sufficient to mediate the indirect defense of maize against herbivore attack.

  植物可以通过吸引草食动物的天敌来自我防御。吸引的信号通常是草食动物诱导的植物挥发物的复杂混合物，这使得证明特定化合物的作用变得困难。玉米在被鳞翅目幼虫食害后，会释放一种混合物，对各种寄生蜂的雌性非常具有吸引力。我们鉴定了萜烯合酶TPS10，该酶可以从底物茉莉酸二磷酸酯中形成（E）-β-茉莉烯、（E）-α-柠檬烯和其他草食动物诱导的倍半萜烃烃化合物。相应的基因会在草食动物攻击时表达，并在转录水平上受到调控。在拟南芥中过表达tps10导致植物释放与玉米相同的高量TPS10倍半萜烯产物。在嗅觉器实验中，使用这些转基因拟南芥植物作为气味源表明，寄生蜂Cotesia marginiventris的雌性学会利用TPS10倍半萜烯来定位其鳞翅目寄主，在先前接触这些挥发物与寄主相关的情况下。这种草食动物诱导挥发物混合物的解剖表明，像tps10这样的单一基因足以介导玉米对草食动物攻击的间接防御。
• The Variability of Sesquiterpenes Emitted from Two <i>Zea mays</i> Cultivars Is Controlled by Allelic Variation of Two Terpene Synthase Genes Encoding Stereoselective Multiple Product Enzymes
  作者：Tobias G. Köllner、Christiane Schnee、Jonathan Gershenzon、Jörg Degenhardt

  DOI：10.1105/tpc.019877

  日期：2004.5

  The mature leaves and husks of Zea mays release a complex blend of terpene volatiles after anthesis consisting predominantly of bisabolane-, sesquithujane-, and bergamotane-type sesquiterpenes. The varieties B73 and Delprim release the same volatile constituents but in significantly different proportions. To study the molecular genetic and biochemical mechanisms controlling terpene diversity and distribution in these varieties, we isolated the closely related terpene synthase genes terpene synthase4 (tps4) and tps5 from both varieties. The encoded enzymes, TPS4 and TPS5, each formed the same complex mixture of sesquiterpenes from the precursor farnesyl diphosphate but with different proportions of products. These mixtures correspond to the sesquiterpene blends observed in the varieties B73 and Delprim, respectively. The differences in the stereoselectivity of TPS4 and TPS5 are determined by four amino acid substitutions with the most important being a Gly instead of an Ala residue at position 409 at the catalytic site of the enzyme. Although both varieties contain tps4 and tps5 alleles, their differences in terpene composition result from the fact that B73 has only a single functional allele of tps4 and no functional alleles of tps5, whereas Delprim has only a functional allele of tps5 and no functional alleles of tps4. Lack of functionality was shown to be attributable to frame-shift mutations or amino acid substitutions that greatly reduce the activity of their encoded proteins. Therefore, the diversity of sesquiterpenes in these two maize cultivars is strongly influenced by single nucleotide changes in the alleles of two terpene synthase genes.

  玉米成熟叶片和果壳在开花后释放出一种复杂的萜烯挥发物混合物，主要由红没药烷、倍半萜烷和佛手柑烷类倍半萜组成。B73和Delprim这两个品种释放的挥发物成分相同，但比例明显不同。为了研究控制这些品种中萜烯多样性和分布的分子遗传和生化机制，我们从这两个品种中分离出了密切相关的萜烯合成酶基因terpene synthase4（tps4）和tps5。编码的酶TPS4和TPS5分别从前体法呢基二磷酸形成相同的倍半萜混合物，但产物比例不同。这些混合物分别对应于在B73和Delprim品种中观察到的倍半萜混合物。TPS4和TPS5在立体选择性上的差异是由四个氨基酸取代决定的，其中最重要的是在酶催化位点第409位由甘氨酸取代了丙氨酸残基。虽然这两个品种都含有tps4和tps5等位基因，但它们在萜烯组成上的差异是由于B73只有一个tps4的功能等位基因，而没有tps5的功能等位基因，而Delprim只有一个tps5的功能等位基因，而没有tps4的功能等位基因。功能缺失是由于移码突变或氨基酸取代导致其编码蛋白活性大大降低。因此，这两个玉米栽培品种
• Molecular and biochemical evolution of maize terpene synthase 10, an enzyme of indirect defense
  作者：Tobias G. Köllner、Jonathan Gershenzon、Jörg Degenhardt

  DOI：10.1016/j.phytochem.2009.06.011

  日期：2009.6

  Maize plants attacked by lepidopteran larvae emit a volatile mixture that consists mostly of the sesquiterpene olefins, (E)-alpha-bergamotene and (E)-beta-farnesene. These volatiles are produced by the herbivore-induced terpene synthase TPS10 and attract natural enemies to the damaged plants. A survey of volatiles in maize lines and species of teosinte showed that the TPS10 products (E)-alpha-bergamotene and (E)-beta-farnesene are consistently induced by herbivory, indicating that release of TPS10 volatiles is a defense trait conserved among maize and its wild relatives. Sequence comparison of TPS10 from maize and its apparent orthologs from four teosinte species demonstrated stabilizing selection on this defense trait. The teosinte volatiles and the enzymatic activity of the apparent TPS10 orthologs were not completely uniform but varied in the ratio of (E)-alpha-bergamotene to (E)-beta-farnesene products formed. We identified a single amino acid in the active center which determines the ratio of (E)-alpha-bergamotene to (E)-beta-farnesene and has changed during the evolution of maize and teosinte species. Feeding experiments with the substrate (Z,E)-farnesyl diphosphate revealed that this amino acid controls the rate of isomerization of the (E,E)-farnesyl carbocation intermediate to the (Z,E)-configuration. (C) 2009 Elsevier Ltd. All rights reserved
• Substrate geometry controls the cyclization cascade in multiproduct terpene synthases from Zea mays
  作者：Abith Vattekkatte、Nathalie Gatto、Tobias G. Köllner、Jörg Degenhardt、Jonathan Gershenzon、Wilhelm Boland

  DOI：10.1039/c5ob00711a

  日期：——

  Multiproduct terpene synthases on incubation with (2Z) substrates showed enhanced enzymatic turnover with distinct preference for cyclic products than corresponding (2E) substrates.

  多产品萜烯合成酶在与（2Z）底物孵育后，表现出增强的酶促转化能力，对环状产物的偏好明显高于相应的（2E）底物。