α-longipinene

• 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: α-longipinene
• 英文别名: α-Longipinen；2,6,6,9-tetramethyl-tricyclo[5.4.0.0^2,8]undec-9-ene；(+)-alpha-Longipinene；2,6,6,9-tetramethyltricyclo[5.4.0.02,8]undec-9-ene
• 化学式: C₁₅H₂₄
• mdl: MFCD24390301
• 分子量: 204.356
• InChiKey: HICYDYJTCDBHMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.866
• 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 α-longipinene 、 pyrophosphoric acid
  参考文献：
  名称：

  9个挪威云杉TPS基因的功能表征以及TPS-d亚科的裸子植物萜烯合酶的进化。

  摘要：

  本构和诱导的类萜是许多植物抵抗潜在草食动物和病原体的重要防御化合物。在挪威的云杉（Picea abies L. Karst）中，用茉莉酸甲酯处理可引起复杂的化学和生化萜类防御反应，这与茎中创伤性树脂导管发育以及针中挥发性萜类化合物释放有关。（+）-3-carene合酶的克隆是在分子遗传学水平上表征该系统的第一步。在这里，我们报告了来自挪威云杉的9种其他萜烯合酶（TPS）cDNA的分离和功能表征。这些cDNA编码四个单萜合酶，月桂烯合酶，（-）-柠檬烯合酶，（-）-α/β-pine烯合酶，和（-）-芳樟醇合酶。三个倍半萜烯合酶，长叶烯合酶，E，E-α-法呢烯合酶，和E-alpha-bisabolene合酶；以及两种二萜合酶，即异欧美拉拉-7,15-二烯合酶和左旋美联radi /枞二烯合酶，​​每种产物都有其独特的特征。据我们所知，以前没有描述过编码异波美拉-7,15-二烯合酶和长叶烯合酶的基

  DOI：

  10.1104/pp.104.042028

文献信息

• Does egg deposition by herbivorous pine sawflies affect transcription of sesquiterpene synthases in pine?
  作者：Diana Köpke、Roland Schröder、Hanna M. Fischer、Jonathan Gershenzon、Monika Hilker、Axel Schmidt

  DOI：10.1007/s00425-008-0747-8

  日期：2008.8

  Scots pine (Pinus sylvestris; Pinaceae, Pinales) is known to defend against egg deposition by herbivorous sawflies by changing its terpenoid volatile blend. The oviposition-induced pine odor attracts egg parasitoids that kill the sawfly eggs. Here, we investigated whether sawfly egg deposition activates genes encoding pine terpene synthases by extracting mRNA from oviposition-induced P. sylvestris. Three new sesquiterpene synthases, PsTPS 1, PsTPS 2, and PsTPS 3, were isolated that were shown on heterologous expression in Escherichia coli to produce (E)-beta-caryophyllene and alpha-humulene (PsTPS 1), 1(10),5-germacradiene-4-ol (PsTPS 2), and longifolene and alpha-longipinene (PsTPS 3) as their principal products. Quantitative RT-PCR analyses revealed that transcript levels of PsTPS 1 and PsTPS 2 were significantly higher in oviposition-induced twigs that were attractive to the parasitoids than in non-attractive, artificially damaged twigs. Thus, our results demonstrate a specific transcription response to egg deposition, distinct from that caused by artificial wounding. Transcripts of PsTPS 3 did not change in response to egg deposition. The transcript levels of PsTPS 1, PsTPS 2, and PsTPS 3 were also determined in relation to time after egg deposition, since pine odor is attractive to the parasitoid only 72 h after egg deposition. Transcription rates of PsTPS 1 and PsTPS 2 were significantly enhanced only 72 h after egg deposition, thus matching the timing of odor attractiveness, while for PsTPS 3, enhanced transcription was not detected at any time period studied after egg deposition. The ecological significance of the oviposition-induced increase of sesquiterpene synthase transcripts is discussed.

表征谱图