germacrene C | 34323-15-4

• 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: germacrene C
• 英文别名: (1E,3E,7E)-1,7-dimethyl-4-propan-2-ylcyclodeca-1,3,7-triene
• CAS: 34323-15-4
• 化学式: C₁₅H₂₄
• 分子量: 204.35
• InChiKey: WYGLLWYGQRUNLF-XZCMGSLHSA-N

物化性质

• 沸点：
  287.9±15.0 °C(Predicted)
• 密度：
  0.839±0.06 g/cm3(Predicted)
• LogP：
  6.950 (est)
• 保留指数：
  1493;1493;1493;1482;1493;1528;1502;1482

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  germacrene C 以 正戊烷 为溶剂， 以Comparison of this compound with authentic δ-elemene (FIG. 1) from black pepper oleoresin yielded an identical retention time and mass spectrum的产率得到delta-Elemene
  参考文献：
  名称：

  Germacrene C synthase gene of Lycopersicon esculentum

  摘要：

  番茄中的萜烯合酶基因已被克隆和测序。在植物中转基因表达萜烯合酶可以导致有益和有用的特征，如增加宿主对病原体和食草动物的抵抗力以及改变风味和气味特征。

  公开号：

  US06342380B1
• 作为产物：
  描述：

  farnesyl pyrophosphate 生成 pyrophosphoric acid 、 germacrene C
  参考文献：
  名称：

  RNA-seq discovery, functional characterization, and comparison of sesquiterpene synthases from Solanum lycopersicum and Solanum habrochaites trichomes

  摘要：

  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

  DOI：

  10.1007/s11103-011-9813-x

文献信息

• Sesquiterpene synthases from grand fir (abies grandis), and methods of use
  申请人：Washington State University Research Foundation

  公开号：US20020038001A1

  公开（公告）日：2002-03-28

  cDNAs encoding E-&agr;-bisabolelene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase from Grand Fir ( Abies grandis ) have been isolated and sequenced, and the corresponding amino acid sequences have been determined. Accordingly, isolated DNA sequences (SEQ ID No:12; SEQ ID No:19 and SEQ ID No:23) are provided which code for the expression of E-&agr;-bisabolene synthase (SEQ ID No:13), &dgr;-selinene synthase (SEQ ID No:20) and &ggr;-humulene synthase (SEQ ID No:24), respectively, from Grand Fir ( Abies grandis ). In other aspects, replicable recombinant cloning vehicles are provided which code for E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase, or for a base sequence sufficiently complementary to at least a portion of E-&agr;-bisabolene synthase, &dgr;-selinene synthase or &ggr;-humulene synthase DNA or RNA to enable hybridization therewith. In yet other aspects, modified host cells are provided that have been transformed, transfected, infected and/or injected with a recombinant cloning vehicle and/or DNA sequence encoding E-&agr;-bisabolene synthase, &dgr;-selinene synthase or &ggr;-humulene synthase. Thus, systems and methods are provided for the recombinant expression of the aforementioned recombinant sesquiterpene synthases that may be used to facilitate their production, isolation and purification in significant amounts. Recombinant E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase may be used to obtain expression or enhanced expression of E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase in plants in order to enhance the production of sesquiterpenoids, or may be otherwise employed for the regulation or expression of E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase, or the production of their products.

  从大冷杉（Abies grandis）中分离和测序了编码E-α-双萜烯合酶、δ-塞林烯合酶和γ-蒿莲烯合酶的cDNA，并确定了相应的氨基酸序列。因此，提供了编码大冷杉（Abies grandis）中的E-α-双萜烯合酶（SEQ ID No：13）、δ-塞林烯合酶（SEQ ID No：20）和γ-蒿莲烯合酶（SEQ ID No：24）表达的分离DNA序列（SEQ ID No：12；SEQ ID No：19和SEQ ID No：23）。在其他方面，提供了可复制的重组克隆载体，其编码E-α-双萜烯合酶、δ-塞林烯合酶和γ-蒿莲烯合酶，或编码与E-α-双萜烯合酶、δ-塞林烯合酶或γ-蒿莲烯合酶DNA或RNA的至少一部分足够互补的碱基序列，以使其与之杂交。在其他方面，提供了经改造的宿主细胞，它们已经转化、转染、感染和/或注入了重组克隆载体和/或编码E-α-双萜烯合酶、δ-塞林烯合酶或γ-蒿莲烯合酶的DNA序列。因此，提供了用于重组表达前述重组倍半萜合酶的系统和方法，可用于促进它们的大量生产、分离和纯化。重组E-α-双萜烯合酶、δ-塞林烯合酶和γ-蒿莲烯合酶可用于在植物中获得E-α-双萜烯合酶、δ-塞林烯合酶和γ-蒿莲烯合酶的表达或增强表达，以增强倍半萜类物质的生产，或者可用于调节或表达E-α-双萜烯合酶、δ-塞林烯合酶和γ-蒿莲烯合酶，或其产物的生产。
• Gymnosperm nucleic acid molecules encoding sesquiterpene synthases and methods of use
  申请人：Washington State University Foundation

  公开号：US06265639B1

  公开（公告）日：2001-07-24

  cDNAs encoding E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase from Grand Fir (Abies grandis) have been isolated and sequenced, and the corresponding amino acid sequences have been determined. Accordingly, isolated DNA sequences (SEQ ID No:12 and SEQ ID No:19 and SEQ ID No:23) are provided which code for the expression of E-&agr;-bisabolene synthase (SEQ ID No:13), &dgr;-selinene synthase (SEQ ID No:20) and &ggr;-humulene synthase (SEQ ID No: 24), respectively, from Grand Fir (Abies grandis). In other aspects, replicable recombinant cloning vehicles are provided which code for E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase, or for a base sequence sufficiently complementary to at least a portion of E-&agr;-bisabolene synthase, &dgr;-selinene synthase or &ggr;-humulene synthase DNA or RNA to enable hybridization therewith. In yet other aspects, modified host cells are provided that have been transformed, transfected, infected and/or injected with a recombinant cloning vehicle and/or DNA sequence encoding E-&agr;-bisabolene synthase, &dgr;-selinene synthase or &ggr;-humulene synthase. Thus, systems and methods are provided for the recombinant expression of the aforementioned recombinant sesquiterpene synthases that may be used to facilitate their production, isolation and purification in significant amounts. Recombinant E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase may be used to obtain expression or enhanced expression of E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase in plants, or may be otherwise employed for the regulation or expression of E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase.

  已经分离和测序了来自大冷杉（Abies grandis）的编码E-α-藿烯合酶、δ-塞林烯合酶和γ-葎草烯合酶的cDNA，并确定了相应的氨基酸序列。因此，提供了编码来自大冷杉的E-α-藿烯合酶（SEQ ID No：13）、δ-塞林烯合酶（SEQ ID No：20）和γ-葎草烯合酶（SEQ ID No：24）表达的隔离DNA序列（SEQ ID No：12和SEQ ID No：19和SEQ ID No：23）。在其他方面，提供了可复制的重组克隆载体，其编码E-α-藿烯合酶、δ-塞林烯合酶和γ-葎草烯合酶，或者编码足够互补至少一部分E-α-藿烯合酶、δ-塞林烯合酶或γ-葎草烯合酶DNA或RNA的碱基序列，以使其能够与其杂交。在其他方面，提供了经过改造的宿主细胞，其已转化、转染、感染和/或注入重组克隆载体和/或编码E-α-藿烯合酶、δ-塞林烯合酶或γ-葎草烯合酶的DNA序列。因此，提供了用于重组表达前述重组倍半萜合酶的系统和方法，可用于促进其大量生产、分离和纯化。重组的E-α-藿烯合酶、δ-塞林烯合酶和γ-葎草烯合酶可用于在植物中获得E-α-藿烯合酶、δ-塞林烯合酶和γ-葎草烯合酶的表达或增强表达，或者可用于调节或表达E-α-藿烯合酶、δ-塞林烯合酶和γ-葎草烯合酶。
• Sesquiterpene synthases from grand fir (Abies grandis), and methods of use
  申请人：Washington State University Research Foundation

  公开号：US06451576B1

  公开（公告）日：2002-09-17

  cDNAs encoding, E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase from Grand Fir (Abies grandis) have been isolated and sequenced, and the corresponding amino acid sequences have been determined. Accordingly, isolated DNA sequences (SEQ ID No:12; SEQ ID No:19 and SEQ ID No:23) are provided which code for the expression of E-&agr;-bisabolene synthase (SEQ ID No:13), &dgr;-selinene synthase (SEQ ID No:20) and &ggr;-humulene synthase (SEQ ID No:24), respectively, from Grand Fir (Abies grandis). In other aspects, replicable recombinant cloning vehicles are provided which code for E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase, or for a base sequence sufficiently complementary to at least a portion of E-&agr;-bisabolene synthase, &dgr;-selinene synthase or &ggr;-humulene synthase DNA or RNA to enable hybridization therewith. In yet other aspects, modified host cells are provided that have been transformed, transfected, infected and/or injected with a recombinant cloning vehicle and/or DNA sequence encoding E-&agr;-bisabolene synthase, &dgr;-selinene synthase or ,&ggr;-humulene synthase. Thus, systems and methods are provided for the recombinant expression of the aforementioned recombinant sesquiterpene syntheses that may be used to facilitate their production, isolation and purification in significant amounts. Recombinant E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase may be used to obtain expression or enhanced expression of E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase in plants in order to enhance the production of sesquiterpenoids, or may be otherwise employed for the regulation or expression of E-&agr;-bisabolene synthase, &dgr;-selinene synthase and &ggr;-humulene synthase, or the production of their products.

  从大冷杉（Abies grandis）中分离和测序了编码E-α-芬烯合酶、δ-塞林烯合酶和γ-葎草烯合酶的cDNA，并确定了相应的氨基酸序列。因此，提供了编码大冷杉（Abies grandis）中的E-α-芬烯合酶（SEQ ID No:13）、δ-塞林烯合酶（SEQ ID No:20）和γ-葎草烯合酶（SEQ ID No:24）表达的分离DNA序列（SEQ ID No:12、SEQ ID No:19和SEQ ID No:23）。在其他方面，提供了可复制的重组克隆载体，其编码E-α-芬烯合酶、δ-塞林烯合酶和γ-葎草烯合酶，或编码与E-α-芬烯合酶、δ-塞林烯合酶或γ-葎草烯合酶DNA或RNA的至少一部分足够互补的碱基序列，以使其能够与之杂交。在其他方面，提供了经过改造的宿主细胞，这些细胞已被转化、转染、感染和/或注射了重组克隆载体和/或编码E-α-芬烯合酶、δ-塞林烯合酶或γ-葎草烯合酶的DNA序列。因此，提供了用于重组表达上述重组倍半萜合成物的系统和方法，可用于促进它们的大量生产、分离和纯化。重组E-α-芬烯合酶、δ-塞林烯合酶和γ-葎草烯合酶可用于在植物中获得E-α-芬烯合酶、δ-塞林烯合酶和γ-葎草烯合酶的表达或增强表达，以增强倍半萜类化合物的产生，或者可用于调节或表达E-α-芬烯合酶、δ-塞林烯合酶和γ-葎草烯合酶，或其产物的生产。
• 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
• Germacrene C synthase from <i>Lycopersicon esculentum</i> cv. VFNT Cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase
  作者：Sheila M. Colby、John Crock、Barbara Dowdle-Rizzo、Peggy G. Lemaux、Rodney Croteau

  DOI：10.1073/pnas.95.5.2216

  日期：1998.3.3

  Germacrene C was found by GC-MS and NMR analysis to be the most abundant sesquiterpene in the leaf oil of Lycopersicon esculentum cv. VFNT Cherry, with lesser amounts of germacrene A, guaia-6,9-diene, germacrene B, β-caryophyllene, α-humulene, and germacrene D. Soluble enzyme preparations from leaves catalyzed the divalent metal ion-dependent cyclization of [1- ³ H]farnesyl diphosphate to these same sesquiterpene olefins, as determined by radio-GC. To obtain a germacrene synthase cDNA, a set of degenerate primers was constructed based on conserved amino acid sequences of related terpenoid cyclases. With cDNA prepared from leaf epidermis-enriched mRNA, these primers amplified a 767-bp fragment that was used as a hybridization probe to screen the cDNA library. Thirty-one clones were evaluated for functional expression of terpenoid cyclase activity in Escherichia coli by using labeled geranyl, farnesyl, and geranylgeranyl diphosphates as substrates. Nine cDNA isolates expressed sesquiterpene synthase activity, and GC-MS analysis of the products identified germacrene C with smaller amounts of germacrene A, B, and D. None of the expressed proteins was active with geranylgeranyl diphosphate; however, one truncated protein converted geranyl diphosphate to the monoterpene limonene. The cDNA inserts specify a deduced polypeptide of 548 amino acids ( M _r = 64,114), and sequence comparison with other plant sesquiterpene cyclases indicates that germacrene C synthase most closely resembles cotton δ-cadinene synthase (50% identity).

  通过GC-MS和NMR分析，发现Germacrene C是番茄（Lycopersicon esculentum cv. VFNT Cherry）叶油中最丰富的倍半萜化合物，较少量的Germacrene A、guaia-6,9-diene、Germacrene B、β-caryophyllene、α-humulene和Germacrene D。叶子中的可溶性酶制剂催化了[1-3H]farnesyl二磷酸盐的双价金属离子依赖性环化反应，形成了这些倍半萜烯烃，这是通过放射性气相色谱确定的。为了获得Germacrene合酶cDNA，构建了一组退化引物，基于相关萜类环化酶的保守氨基酸序列。使用叶表皮富集的mRNA制备的cDNA，这些引物扩增了一个767 bp的片段，用作杂交探针筛选cDNA文库。使用标记的geranyl、farnesyl和geranylgeranyl二磷酸盐作为底物，在大肠杆菌中评估了31个cDNA克隆的萜类环化酶活性。9个cDNA分离物表达了倍半萜合酶活性，GC-MS分析产品鉴定出Germacrene C以及少量的Germacrene A、B和D。没有任何表达蛋白对geranylgeranyl二磷酸盐具有活性，但是一个截短的蛋白质将geranyl二磷酸盐转化为单萜烯柠檬烯。cDNA插入物指定了一个由548个氨基酸（Mr=64,114）组成的推导多肽，与其他植物倍半萜环化酶的序列比较表明，Germacrene C合酶最接近棉花δ-cadinene合酶（50%同源性）。