7-epizingiberene | 158848-19-2

• 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: 7-epizingiberene
• 英文别名: (5R)-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
• CAS: 158848-19-2
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: KKOXKGNSUHTUBV-HUUCEWRRSA-N

物化性质

• 沸点：
  270.7±7.0 °C(Predicted)
• 密度：
  0.854±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  4
• 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：

  7-epizingiberene 在 palladium on activated charcoal 作用下， 以 苯 为溶剂， 反应 8.0h， 以3 mg的产率得到alpha-姜黄烯
  参考文献：
  名称：

  7-Epizingiberene，一种来自野番茄叶片的新型双倍半萜倍半萜

  摘要：

  从2个野生番茄叶（Lycopersicon hirsutum f glabratum PI 199381和Lycopersicon hirsutum PI 365906）的叶片中分离出的AC 15烃已鉴定为7-epizingiberene（2），姜油烯的非对映异构体（1），其存在于姜精油中。用于结构分配2是基于其1 H NMR，13 C NMR，IR，UV和质谱特性。姜丁烯和表姜丁烯的所有光谱数据都相同，除了15 13 C NMR共振中的9个共振，这建立了这些倍半萜的非对映异构关系。4 S，7 - [R epizingiberene的立体化学通过脱氢被证明（7 - [R ）- AR -姜黄烯（4）。姜油烯的相反的7 R和7 S立体化学意味着可能发生常见的（S）-双糖基碳正离子中间体（10A）的相反侧链旋转，从而允许其各自的生物合成中从（E，E）-法呢基进行立体电子学上有利的氢化物移位二磷酸。

  DOI：

  10.1016/s0040-4020(01)89415-1
• 作为产物：
  描述：

  异戊烯醇 在 pyruvate kinase 、 L-1,4-二硫代苏糖醇 、 isopentenyl phosphate kinase from Methanocaldococcus jannaschii 、 (2Z,6Z)-FDP synthase from Solanum habrochaites 、 7-epizingiberene synthase from Solanum habrochaites 、 Escherichia coli hydroxyethylthiazole kinase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 48.0h， 生成 7-epizingiberene
  参考文献：
  名称：

  萜烯及其类似物的模块化化学酶促合成。

  摘要：

  非天然萜类化合物具有作为药物和农用化学品的潜力。然而，它们的化学合成通常是长的，复杂的，并且不易于大规模生产。在这里，我们报告了一种模块化的化学酶法，可以从以定量产量产生的二磷酸化前体中合成萜烯类似物。通过添加异戊二烯基转移酶，法呢基二磷酸（2E，6E）-FDP和（2Z，6Z）-FDP的分离率超过80％。还实现了14,15-二甲基-FDP，12-甲基-FDP，12-羟基-FDP，均-FDP和15-甲基-FDP的合成。这些改性的二磷酸酯与萜烯合酶一起使用，以生产非天然的倍半萜类化学信息素（S）-14,15-二甲基Germacrene D和（S）-12-甲基Germacrene D以及二氢青蒿素醛。

  DOI：

  10.1002/anie.202001744

文献信息

• Total Synthesis and Structural Revision of Biyouyanagin B
  作者：K. C. Nicolaou、Silvano Sanchini、T. Robert Wu、David Sarlah

  DOI：10.1002/chem.201001474

  日期：——

  An intriguing chase of the newly reported biyouyanagin B leads to its total synthesis and structural revision from 1′ to 1.

  对新报道的 biyouyanagin B的有趣追逐导致其从1'到1 的全合成和结构修改。
• [EN] COMPOSITIONS AND METHODS TO ATTRACT THE BROWN MARMORATED STINK BUG (BMSB), HALYOMORPHA HALYS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR ATTIRER LES PUNAISES MARBRÉES BRUNES (BMSB), HALYOMORPHA HALYS
  申请人：US AGRICULTURE

  公开号：WO2013090703A1

  公开（公告）日：2013-06-20

  A composition (useful for attracting Halyomorpha halys) containing (3R,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, and optionally a carrier material or carrier. The composition may also contain (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol where the composition contains a 3:1 ratio of cis-epoxybisabolenols : trans-epoxybisabolenols produced from (R)-citronellal. These compositions were based on the newly discovered aggregation pheromone components: (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol. The composition may also contain methyl (2E,4E,6Z)-decatrieonate. Also a method for attracting Halyomorpha halys to an object or area, involving treating said object or area with a Halyomorpha halys attracting composition containing a Halyomorpha halys attracting effective amount of the composition.

  一种吸引半环纹椿象的组合物，包含（3R,6R,7R,10S）-10,11-环氧-1-双萜-3-醇，（3R,6R,7R,10R）-10,11-环氧-1-双萜-3-醇，（3S,6S,7R,10S）-10,11-环氧-1-双萜-3-醇，（3S,6S,7R,10R）-10,11-环氧-1-双萜-3-醇，以及可选的载体材料或载体。该组合物还可以包含（3R,6S,7R,10S）-10,11-环氧-1-双萜-3-醇，（3R,6S,7R,10R）-10,11-环氧-1-双萜-3-醇，（3S,6R,7R,10S）-10,11-环氧-1-双萜-3-醇，（3S,6R,7R,10R）-10,11-环氧-1-双萜-3-醇，其中该组合物包含从（R）-柠檬醛产生的顺式环氧双萜醇和反式环氧双萜醇的3:1比例。这些组合物基于新发现的聚集信息素成分：（3S,6S,7R,10S）-10,11-环氧-1-双萜-3-醇和（3R,6S,7R,10S）-10,11-环氧-1-双萜-3-醇。该组合物还可以含有甲基（2E,4E,6Z）-癸三烯酸甲酯。还提供了一种吸引半环纹椿象到物体或区域的方法，涉及使用含有半环纹椿象吸引有效量的吸引组合物处理所述物体或区域。
• Improved herbivore resistance in cultivated tomato with the sesquiterpene biosynthetic pathway from a wild relative
  作者：Petra M. Bleeker、Rossana Mirabella、Paul J. Diergaarde、Arjen VanDoorn、Alain Tissier、Merijn R. Kant、Marcel Prins、Martin de Vos、Michel A. Haring、Robert C. Schuurink

  DOI：10.1073/pnas.1208756109

  日期：2012.12.4

  that is produced and stored in glandular trichomes. We identified 7-epizingiberene synthase (ShZIS) that belongs to a new class of sesquiterpene synthases, exclusively using Z-Z-farnesyl-diphosphate (zFPP) in plastids, probably arisen through neo-functionalization of a common ancestor. Expression of the ShZIS and zFPP synthases in the glandular trichomes of cultivated tomato resulted in the production

  番茄育种在提高果实质量和数量方面非常有效，但并未专注于提高食草动物的抵抗力。将在野生番茄中生产 7-epizingiberene 的生物合成途径引入温室栽培品种，目的是获得食草动物的抗性。7-Epizingiberene 是一种特殊的倍半萜，具有毒性和驱虫特性，可在腺毛状体中产生和储存。我们鉴定了 7-epizingiberene 合酶 (ShZIS)，它属于一类新的倍半萜烯合酶，在质体中专门使用 ZZ-法呢基二磷酸 (zFPP)，可能是通过共同祖先的新功能化产生的。ShZIS 和 zFPP 合酶在栽培番茄的腺毛中的表达导致产生 7-epizingiberene。这些番茄对几种番茄害虫的食草动物产生了抵抗力。因此，将这种倍半萜烯生物合成途径引入栽培番茄可提高食草动物的抗性。
• Discovery of the Aggregation Pheromone of the Brown Marmorated Stink Bug (<i>Halyomorpha halys</i>) through the Creation of Stereoisomeric Libraries of 1-Bisabolen-3-ols
  作者：Ashot Khrimian、Aijun Zhang、Donald C. Weber、Hsiao-Yung Ho、Jeffrey R. Aldrich、Karl E. Vermillion、Maxime A. Siegler、Shyam Shirali、Filadelfo Guzman、Tracy C. Leskey

  DOI：10.1021/np5003753

  日期：2014.7.25

  We describe a novel and straightforward route to all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol via the rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones 1 and 2. The detailed stereoisomeric structures of many natural sesquiterpenes with the bisabolane skeleton were previously unknown because of the absence of stereoselective syntheses of individual stereoisomers. Several of the bisabolenols are pheromones of economically important pentatomid bug species. Single-crystal X-ray crystallography of underivatized triol 13 provided unequivocal proof of the relative and absolute configurations. Two of the epoxides, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (3) and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (4), were identified as the main components of a male-produced aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys, using GC analyses on enantioselective columns. Both compounds attracted female, male, and nymphal H. halys in field trials. Moreover, mixtures of stereoisomers containing epoxides 3 and 4 were also attractive to H. halys, signifying that the presence of additional stereoisomers did not hinder attraction of H. halys and relatively inexpensive mixtures can be used in monitoring, as well as control strategies. H. halys is a polyphagous invasive species in the U.S. and Europe that causes severe injury to fruit, vegetables, and field crops and is also a serious nuisance pest.
• Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies
  作者：Petra M. Bleeker、Paul J. Diergaarde、Kai Ament、Stefan Schütz、Bettina Johne、Jan Dijkink、Henk Hiemstra、René de Gelder、Michiel T.J. de Both、Maurice W. Sabelis、Michel A. Haring、Robert C. Schuurink

  DOI：10.1016/j.phytochem.2010.10.014

  日期：2011.1

  How whiteflies (Bemisia tabaci) make the choice for a host plant prior to landing, is not precisely known. Here we investigated whether they respond to specific volatiles of tomato. Zingiberene and curcumene were purified from Solanum habrochaites (PI127826), characterised by NMR and X-ray analysis and identified as 7-epizingiberene and R-curcumene. In contrast, oil from Zingiber officinalis contained the stereoisomers zingiberene and S-curcumene, respectively. Using a combination of free-choice bio-assays and electroantennography, 7-epizingiberene and its dehydrogenated derivative R-curcumene were shown to be active as semiochemicals to B. tabaci adults, whereas the stereoisomers from ginger were not. In addition, R-curcumene elicited the strongest electroantennographic response. Bio-assays showed that a cultivated tomato could be made less attractive to B. tabaci than its neighbouring siblings by the addition of the tomato stereoisomer 7-epizingiberene or its derivative R-curcumene. These sesquiterpenes apparently repel adult whiteflies prior to landing, presumably because it informs them that after landing they, or their offspring, may be exposed to higher and lethal concentrations of the same compounds. (C) 2010 Elsevier Ltd. All rights reserved.