α-zingiberene | 1443410-84-1

• 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-zingiberene
• 英文别名: 2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
• CAS: 1443410-84-1
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: KKOXKGNSUHTUBV-GICMACPYSA-N

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：

  α-zingiberene 在 氢气 作用下， 以 正己烷 为溶剂， 90.0~120.0 ℃ 、2.63 MPa 条件下， 反应 6.0h， 以65%的产率得到
  参考文献：
  名称：

  Chemical Composition and Cytotoxicity Evaluation of Essential Oil from Leaves of Casearia Sylvestris, Its Main Compound α-Zingiberene and Derivatives

  摘要：

  茜草（水杨梅科），俗称 "guaçatonga"，是一种在民间医学中被广泛用于治疗包括癌症在内的各种疾病的植物。本研究涉及其精油、主要成分和衍生物的化学成分以及细胞毒性评估。因此，使用 Clevenger 型仪器从西洋芹叶中提取了粗精油，并通过 GC/MS 进行了分析。分析鉴定出 23 种物质，其中 13 种占精油总成分的 98.73%，倍半萜 a-zingiberene 占精油的 50%。精油对几种肿瘤细胞株的细胞毒性活性进行了评估，得出的 IC50 值从 12 毫克/毫升到 153 毫克/毫升不等。从精油中分离出的纯a-zingiberene也对肿瘤细胞系进行了评估，显示出对HeLa、U-87、Siha和HL60细胞系的活性，但其IC50值高于粗精油的IC50值。为了评估a-zingiberene双键对细胞毒性活性的影响，我们得到了部分氢化的a-zingiberene（PHZ）和完全氢化的a-zingiberene（THZ）衍生物。部分氢化的衍生物只对 B16F10-Nex2 细胞系具有细胞毒性活性（IC50 值为 65 毫克/毫升），而完全氢化的衍生物几乎对所有细胞系都具有细胞毒性活性，但 B16F10-Nex2 和 MCF-7 细胞系除外，IC50 值从 34 毫克/毫升到 65 毫克/毫升不等。这些结果表明，细胞毒性活性与化合物的氧化状态有关。

  DOI：

  10.3390/molecules18089477
• 作为产物：
  描述：

  4-[(1R)-1,5-dimethylhex-4-enyl]cyclohex-2-en-1-one 在 吡啶 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 22.5h， 生成 α-zingiberene 、 1,3(15),10-bisabolatriene
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS TO ATTRACT THE BROWN MARMORATED STINK BUG (BMSB), HALYOMORPHA HALYS
  [FR] COMPOSITIONS ET PROCÉDÉS POUR ATTIRER LES PUNAISES MARBRÉES BRUNES (BMSB), HALYOMORPHA HALYS

  摘要：

  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。

  公开号：

  WO2013090703A1

文献信息

• 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.
• [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。
• Chemical Composition and Cytotoxicity Evaluation of Essential Oil from Leaves of Casearia Sylvestris, Its Main Compound α-Zingiberene and Derivatives
  作者：Diego Bou、João Lago、Carlos Figueiredo、Alisson Matsuo、Rafael Guadagnin、Marisi Soares、Patricia Sartorelli

  DOI：10.3390/molecules18089477

  日期：——

  Casearia sylvestris (Salicaceae), popularly known as “guaçatonga”, is a plant widely used in folk medicine to treat various diseases, including cancer. The present work deals with the chemical composition as well as the cytotoxic evaluation of its essential oil, its main constituent and derivatives. Thus, the crude essential oil from leaves of C. sylvestris was obtained using a Clevenger type apparatus and analyzed by GC/MS. This analysis afforded the identification of 23 substances, 13 of which corresponded to 98.73% of the total oil composition, with sesquiterpene a-zingiberene accounting for 50% of the oil. The essential oil was evaluated for cytotoxic activity against several tumor cell lines, giving IC50 values ranging from 12 to 153 mg/mL. Pure a-zingiberene, isolated from essential oil, was also evaluated against the tumor cell lines showing activity for HeLa, U-87, Siha and HL60 cell lines, but with IC50 values higher than those determined for the crude essential oil. Aiming to evaluate the effect of the double bonds of a-zingiberene on the cytotoxic activity, partially hydrogenated a-zingiberene (PHZ) and fully hydrogenated a-zingiberene (THZ) derivatives were obtained. For the partially hydrogenated derivative only cytotoxic activity to the B16F10-Nex2 cell line (IC50 65mg/mL) was detected, while totally hydrogenated derivative showed cytotoxic activity for almost all cell lines, with B16F10-Nex2 and MCF-7 as exceptions and with IC50 values ranging from 34 to 65 mg/mL. These results indicate that cytotoxic activity is related with the state of oxidation of compound.

  茜草（水杨梅科），俗称 "guaçatonga"，是一种在民间医学中被广泛用于治疗包括癌症在内的各种疾病的植物。本研究涉及其精油、主要成分和衍生物的化学成分以及细胞毒性评估。因此，使用 Clevenger 型仪器从西洋芹叶中提取了粗精油，并通过 GC/MS 进行了分析。分析鉴定出 23 种物质，其中 13 种占精油总成分的 98.73%，倍半萜 a-zingiberene 占精油的 50%。精油对几种肿瘤细胞株的细胞毒性活性进行了评估，得出的 IC50 值从 12 毫克/毫升到 153 毫克/毫升不等。从精油中分离出的纯a-zingiberene也对肿瘤细胞系进行了评估，显示出对HeLa、U-87、Siha和HL60细胞系的活性，但其IC50值高于粗精油的IC50值。为了评估a-zingiberene双键对细胞毒性活性的影响，我们得到了部分氢化的a-zingiberene（PHZ）和完全氢化的a-zingiberene（THZ）衍生物。部分氢化的衍生物只对 B16F10-Nex2 细胞系具有细胞毒性活性（IC50 值为 65 毫克/毫升），而完全氢化的衍生物几乎对所有细胞系都具有细胞毒性活性，但 B16F10-Nex2 和 MCF-7 细胞系除外，IC50 值从 34 毫克/毫升到 65 毫克/毫升不等。这些结果表明，细胞毒性活性与化合物的氧化状态有关。