(1R,7S,10S)-4-Methylidene-7-(1-methylethyl)-10-methylbicyclo[4.4.0]dec-5-ene

• 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: (1R,7S,10S)-4-Methylidene-7-(1-methylethyl)-10-methylbicyclo[4.4.0]dec-5-ene
• 英文别名: (+)-cis-muurola-4(14),5-diene；cis-muurola-4(14),5-diene；cis-muurola-4(15)5-diene；Muurola-4(15),5-diene；(1S,4S,4aR)-4-methyl-7-methylidene-1-propan-2-yl-2,3,4,4a,5,6-hexahydro-1H-naphthalene
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: RNDFUOKDULDZPR-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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 在 甘油 、 magnesium chloride 作用下， 以 phosphate buffer 为溶剂， 以45%的产率得到(1R,7S,10S)-7-(1-Methylethyl)-4,10-dimethylbicyclo[4.4.0]deca-3,5-diene
  参考文献：
  名称：

  Cloning and functional characterisation of a cis-muuroladiene synthase from black peppermint (Mentha×piperita) and direct evidence for a chemotype unable to synthesise farnesene

  摘要：

  Using oligonucleotide primers designed to the known gene sequence of an (E)-beta-farnesene (E beta F) synthase, two cDNA sequences (MxpSS1 and MxpSS2) were cloned from a black peppermint (Mentha x piperita) plant. MxpSS1 encoded a protein with 96% overall amino acid sequence identity with the E beta F synthase. Recombinant MxpSS1 produced in Escherichia coli, after removal of an N-terminal thioredoxin fusion, had a K-m for FPP of 1.91 +/- 0.1 mu M and k(cat), of 0-18 s(-1) and converted farnesyl diphosphate (FPP) into four products, the major two being cis-muurola-3,5-diene (45%) and cis-muurola-4(14),5-diene (43%). This is the first cis-muuroladiene synthase, to be characterised. MxpSS2 encoded a protein with only two amino acids differing from E beta F synthase. Recombinant MxpSS2 protein showed no activity towards FPP. One of the two mutations, at position 531 (leucine in MxpSS2 and serine in E beta F synthase) was shown, by structural modelling to occur in the J-K loop, an element of the structure of sesquiterpene synthases known to be important in the reaction mechanism. Reintroduction of the serine at position 531 into MxpSS2 by site-directed mutagenesis restored E beta F synthase activity (K. for FPP 0.98 +/- 0.12 pM, k(cat) 0-1 s(-1)), demonstrating the crucial role of this residue in the enzyme activity. Analysis, by GC-MS, of the sesquiterpene profile of the plant used for the cloning, revealed that E beta F was not present, confirming that this particular mint chemotype had lost E beta F synthase activity due to the observed mutations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2005.06.012

文献信息

• The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements
  作者：Nils Bülow、Wilfried A König

  DOI：10.1016/s0031-9422(00)00266-1

  日期：2000.9

  Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixtures of sesquiterpenes of the cadinane, eudesmane (selinane), oppositane, axane, isodaucane

  Germacrene D 被认为是许多倍半萜烃的前体。我们研究了从几种一枝黄花物种中分离出的锗烯 D 的酸催化以及光化学和热诱导的重排过程，其中含有锗烯 D 的两种对映异构体。 cadinane、eudesmane (selinane)、opp​​ositane、axane、异十二烷和波旁烷组以及异热菌烯 D 被确定为主要产品，并可作为参考化合物用于植物成分的结构研究和立体化学分配。重排产物之一的 Delta-amorphene 首次被确定为天然产物。γ-阿吗啡的绝对构型通过与锗烯 D 的绝对构型的相关性进行了修正。
• Synthesis of sesquiterpene allylic alcohols and sesquiterpene dienes from Cupressus bakeri and Chamaecyparis obtusa
  作者：Koon-Sin Ngo、Geoffrey D. Brown

  DOI：10.1039/a907752i

  日期：——

  Five muurolane (1–5), one nor-seco-muurolane (6) and one nor-muurolane (7) sesquiterpene natural products recently reported from Cupressus bakeri have been obtained by chemical synthesis together with the unnatural 7-epimeric amorphane analogues of four of these sesquiterpenes (15, 16, 18 and 19). The conversion of sesquiterpene allylic tertiary alcohols 1, 2, 15 and 16 into regioisomeric sesquiterpene

  5片穆罗拉尼（1-5），1片正癸二酸-穆罗拉尼（6）和1片正-穆罗拉尼（7）倍半萜最近通过化学合成获得了来自柏木（Cupressus bakeri）的天然产物，以及其中四个的非天然7-表异构体a啶烷类似物。倍半萜（15，16，18和19）。倍半萜烯丙基的转化叔醇 1，2，15和16为区域异构体倍半萜二烯3-5和17-20进行了研究在体外通过核磁共振 以及这种脱水的机制及其与血脂来源的相关性 倍半萜讨论了已报告为天然产物的二烯（例如3-5）。
• Cloning and functional characterisation of a cis-muuroladiene synthase from black peppermint (Mentha×piperita) and direct evidence for a chemotype unable to synthesise farnesene
  作者：Ian M. Prosser、Racheal J. Adams、Michael H. Beale、Nathan D. Hawkins、Andrew L. Phillips、John A. Pickett、Linda M. Field

  DOI：10.1016/j.phytochem.2005.06.012

  日期：2006.8

  Using oligonucleotide primers designed to the known gene sequence of an (E)-beta-farnesene (E beta F) synthase, two cDNA sequences (MxpSS1 and MxpSS2) were cloned from a black peppermint (Mentha x piperita) plant. MxpSS1 encoded a protein with 96% overall amino acid sequence identity with the E beta F synthase. Recombinant MxpSS1 produced in Escherichia coli, after removal of an N-terminal thioredoxin fusion, had a K-m for FPP of 1.91 +/- 0.1 mu M and k(cat), of 0-18 s(-1) and converted farnesyl diphosphate (FPP) into four products, the major two being cis-muurola-3,5-diene (45%) and cis-muurola-4(14),5-diene (43%). This is the first cis-muuroladiene synthase, to be characterised. MxpSS2 encoded a protein with only two amino acids differing from E beta F synthase. Recombinant MxpSS2 protein showed no activity towards FPP. One of the two mutations, at position 531 (leucine in MxpSS2 and serine in E beta F synthase) was shown, by structural modelling to occur in the J-K loop, an element of the structure of sesquiterpene synthases known to be important in the reaction mechanism. Reintroduction of the serine at position 531 into MxpSS2 by site-directed mutagenesis restored E beta F synthase activity (K. for FPP 0.98 +/- 0.12 pM, k(cat) 0-1 s(-1)), demonstrating the crucial role of this residue in the enzyme activity. Analysis, by GC-MS, of the sesquiterpene profile of the plant used for the cloning, revealed that E beta F was not present, confirming that this particular mint chemotype had lost E beta F synthase activity due to the observed mutations. (c) 2005 Elsevier Ltd. All rights reserved.