(+)-thujopsene | 82262-80-4

• 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: (+)-thujopsene
• 英文别名: cis-thujopsene；(1aR,4aR,8aR)-2,4a,8,8-tetramethyl-1,1a,4,5,6,7-hexahydrocyclopropa[j]naphthalene
• CAS: 82262-80-4
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: WXQGPFZDVCRBME-BPLDGKMQSA-N

物化性质

• 沸点：
  256.5±7.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (+)-thujopsene 、 potassium permanganate 生成 (1aS,2S,4aR,8aR)-2,4a,8,8-tetramethyl-1a,5,6,7-tetrahydro-1H-cyclopropa[j]naphthalen-2-ol
  参考文献：
  名称：

  NAGAHAMA, SHIZUO;TAZAKI, MASATO, BULL. CHEM. SOC. JAP., 60,(1987) N 11, 4175-4177

  摘要：

  DOI：
• 作为产物：
  描述：

  (((1aS,2R,4aR,8aR)-2-hydroxy-4a,8,8-trimethyldecahydrocyclopropa[d]naphthalen-2-yl)methyl)(methylimino)(phenyl)-l6-sulfanone 在 对甲苯磺酸 作用下， 反应 1.5h， 生成 (+)-thujopsene
  参考文献：
  名称：

  .beta.-Hydroxysulfoximine-directed Simmons-Smith cyclopropanations. Synthesis of (-)- and (+)-thujopsene

  摘要：

  DOI：

  10.1021/ja00379a060

文献信息

• Ent-sesquiterpenoids and cyclic bis(bibenzyls) from the german liverwort Marchantia Polymorpha
  作者：Yoshinori Asakawa、Motoo Tori、Toru Masuya、Jan-Peter Frahm

  DOI：10.1016/0031-9422(90)80125-z

  日期：1990.1

  Abstract From the methanol extract of the German liverwort Marchantia polymorpha , three new ent -sesquiterpenoids, ent -9-oxo-α-chamigrene, ent -thujopsan-7β-ol and ent -α-cyperone were isolated together with the previously known ent -thujopsenone and (-)-cyclopropane cuparenol. Furthermore, three cyclic bis(bibenzyls), marchantins J-L, were isolated along with the previously known marchantins A-E

  摘要 从德国地草的甲醇提取物中分离出三种新的ent -倍半萜类化合物ent -9-oxo-α-chamigrene、ent -thujopsan-7β-ol 和ent -α-cyperone 以及之前已知的ent - thujopsenone 和 (-)-环丙烷铜烯醇。此外，三个环状双（联苄基），marchantins JL，与先前已知的 marchantins AE 和 G、间和对羟基苯甲醛、木犀草素、月桂酸和月桂酸一起被分离出来。新化合物的结构通过 1 H 和 13 C NMR 光谱和化学转化表征。本种在化学上与日本多形木霉和古木变种接近。双翅目
• Two sesquiterpene synthases are responsible for the complex mixture of sesquiterpenes emitted from Arabidopsis flowers
  作者：Dorothea Tholl、Feng Chen、Jana Petri、Jonathan Gershenzon、Eran Pichersky

  DOI：10.1111/j.1365-313x.2005.02417.x

  日期：2005.4

  Despite the fact that Arabidopsis is largely self‐pollinating, its flowers emit a complex mixture of terpene volatiles consisting predominantly of a large group of over 20 sesquiterpenes. Here we report that only two terpene synthases, encoded by the florally expressed genes At5g23960 and At5g44630, are responsible for the formation of virtually all sesquiterpenes found in the Arabidopsis floral volatile blend. Two independent mutant lines with T‐DNA insertions in the previously identified At5g23960 gene lacked the emission of three sesquiterpenes, including the main sesquiterpene volatile (E)‐β‐caryophyllene, confirming the previous in vitro functional assignment for this gene. Flowers of a mutant line carrying a T‐DNA insertion in gene At5g44630 emitted these three sesquiterpenes, but did not emit any of the remaining sesquiterpene volatiles. An At5g44630 cDNA was expressed in Escherichia coli and the produced protein catalyzed the conversion of farnesyl diphosphate into over 15 sesquiterpenes in similar proportions to those found in the floral volatile blend. At5g23960 and At5g44630 promoter‐β‐glucuronidase (GUS) fusion experiments demonstrated that both genes are expressed in several parts of the Arabidopsis flower, with strong At5g23960 promoter‐GUS activity in the stigma and strong expression of At5g44630 in intrafloral nectaries. Given the previously reported antimicrobial activity of terpenes, their production in stigmas and nectaries may serve to inhibit microbial infection at these vulnerable sites. A survey of 37 Arabidopsis thaliana ecotypes revealed quantitative, but almost no qualitative, variations of floral monoterpene and sesquiterpene emissions suggesting that floral terpene volatiles must play some significant role in the life of the Arabidopsis plant.

  摘要尽管拟南芥在很大程度上是自花授粉的，但它的花却能散发出复杂的萜烯挥发物混合物，主要由 20 多种倍半萜组成。在这里，我们报告了只有两个萜烯合成酶（由花卉表达基因 At5g23960 和 At5g44630 编码）负责拟南芥花卉挥发性混合物中几乎所有倍半萜的形成。在先前确定的 At5g23960 基因中插入 T-DNA 的两个独立突变株缺乏三种倍半萜的释放，其中包括主要的倍半萜挥发物 (E)-β-石竹烯，这证实了先前对该基因的体外功能分配。基因 At5g44630 中携带 T-DNA 插入物的突变品系的花会释放出这三种倍半萜，但不会释放出任何其余的倍半萜挥发物。At5g44630 cDNA 在大肠杆菌中表达，产生的蛋白质催化二磷酸法尼酯转化为超过 15 种倍半萜，其比例与花香挥发混合物中的比例相似。At5g23960 和 At5g44630 启动子-β-葡萄糖醛酸酶（GUS）融合实验表明，这两个基因在拟南芥花的多个部位都有表达，其中 At5g23960 启动子-GUS 在柱头有很强的活性，而 At5g44630 则在花内蜜腺有很强的表达。鉴于之前报道的萜类化合物的抗菌活性，在柱头和蜜腺中产生萜类化合物可能有助于抑制这些脆弱部位的微生物感染。对 37 个拟南芥生态型的调查显示，花单萜烯和倍半萜烯的排放量存在数量上的差异，但几乎没有质量上的差异，这表明花萜烯挥发物在拟南芥植物的生命中一定扮演着重要角色。
• RNA-seq discovery, functional characterization, and comparison of sesquiterpene synthases from Solanum lycopersicum and Solanum habrochaites trichomes
  作者：Petra M. Bleeker、Eleni A. Spyropoulou、Paul J. Diergaarde、Hanne Volpin、Michiel T. J. De Both、Philipp Zerbe、Joerg Bohlmann、Vasiliki Falara、Yuki Matsuba、Eran Pichersky、Michel A. Haring、Robert C. Schuurink

  DOI：10.1007/s11103-011-9813-x

  日期：2011.11

  Solanum lycopersicum and Solanum habrochaites (f. typicum) accession PI127826 emit a variety of sesquiterpenes. To identify terpene synthases involved in the production of these volatile sesquiterpenes, we used massive parallel pyrosequencing (RNA-seq) to obtain the transcriptome of the stem trichomes from these plants. This approach resulted initially in the discovery of six sesquiterpene synthase cDNAs from S. lycopersicum and five from S. habrochaites. Searches of other databases and the S. lycopersicum genome resulted in the discovery of two additional sesquiterpene synthases expressed in trichomes. The sesquiterpene synthases from S. lycopersicum and S. habrochaites have high levels of protein identity. Several of them appeared to encode for non-functional proteins. Functional recombinant proteins produced germacrenes, β-caryophyllene/α-humulene, viridiflorene and valencene from (E,E)-farnesyl diphosphate. However, the activities of these enzymes do not completely explain the differences in sesquiterpene production between the two tomato plants. RT-qPCR confirmed high levels of expression of most of the S. lycopersicum sesquiterpene synthases in stem trichomes. In addition, one sesquiterpene synthase was induced by jasmonic acid, while another appeared to be slightly repressed by the treatment. Our data provide a foundation to study the evolution of terpene synthases in cultivated and wild tomato.

  番茄（Solanum lycopersicum）和哈勃罗切特番茄（Solanum habrochaites）（f. tyPIcum）的PI127826品系会释放多种倍半萜。为了鉴定参与这些挥发性倍半萜合成的萜合成酶，我们使用大规模平行测序（RNA-seq）获得了这些植物茎毛的转录组。这种方法最初发现了番茄（S. lycopersicum）的6个倍半萜合成酶cDNA和哈勃罗切特番茄（S. habrochaites）的5个倍半萜合成酶cDNA。通过对其他数据库和番茄（S. lycopersicum）基因组的搜索，又发现了2个在茎毛中表达的倍半萜合成酶。番茄（S. lycopersicum）和哈勃罗切特番茄（S. habrochaites）的倍半萜合成酶具有高度的蛋白质同源性。其中一些似乎编码无功能的蛋白质。功能性重组蛋白从（E,E）-法呢基二磷酸酯中产生香豆素、β-石竹烯/α-胡莫烯、绿花烯和瓦伦烯。然而，这些酶的活性并不能完全解释两种番茄植物在倍半萜合成方面的差异。RT-qPCR证实了番茄（S. ly
• Surrogate Splicing for Functional Analysis of Sesquiterpene Synthase Genes
  作者：Shuiqin Wu、Mark A. Schoenbeck、Bryan T. Greenhagen、Shunji Takahashi、Sungbeom Lee、Robert M. Coates、Joseph Chappell

  DOI：10.1104/pp.105.059386

  日期：2005.7.1

  A method for the recovery of full-length cDNAs from predicted terpene synthase genes containing introns is described. The approach utilizes Agrobacterium-mediated transient expression coupled with a reverse transcription-polydeoxyribonucleotide chain reaction assay to facilitate expression cloning of processed transcripts. Subsequent expression of intronless cDNAs in a suitable prokaryotic host provides for direct functional testing of the encoded gene product. The method was optimized by examining the expression of an intron-containing β-glucuronidase gene agroinfiltrated into petunia (Petunia hybrida) leaves, and its utility was demonstrated by defining the function of two previously uncharacterized terpene synthases. A tobacco (Nicotiana tabacum) terpene synthase-like gene containing six predicted introns was characterized as having 5-epi-aristolochene synthase activity, while an Arabidopsis (Arabidopsis thaliana) gene previously annotated as a terpene synthase was shown to possess a novel sesquiterpene synthase activity for α-barbatene, thujopsene, and β-chamigrene biosynthesis.

  摘要：本文描述了一种从含有内含子的预测萜类合成酶基因中恢复全长cDNA的方法。该方法利用农杆菌介导的瞬时表达结合反转录-聚脱氧核苷酸链反应检测来促进已处理转录本的表达克隆。随后，在合适的原核宿主中表达无内含子的cDNA可直接进行编码基因产物的功能测试。通过研究农杆菌介导的内含子含有的β-葡萄糖醛酸酶基因在矮牵牛（Petunia hybrida）叶片中的表达来优化该方法，并通过确定两个先前未经表征的萜类合成酶的功能来证明其实用性。一个含有六个预测内含子的烟草（Nicotiana tabacum）萜类合成酶样基因被表征为具有5-epi-aristolochene合成酶活性，而一个先前注释为萜类合成酶的拟南芥（Arabidopsis thaliana）基因则显示出新颖的顺式-α-巴巴特烯、檀香烯和β-香茅烯生物合成的倍半萜合成酶活性。