(Z)-7-十四碳烯-2-酮 | 72746-33-9

• 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
• 中文名称: (Z)-7-十四碳烯-2-酮
• 中文别名: (9-顺式,9'-顺式)-7,7',8,8'-四氢-psi,psi-胡罗卜素
• 英文名称: 9,9'-Di-cis-zeta-carotene
• 英文别名: (6E,10Z,12E,14E,16E,18E,20E,22Z,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,20,22,26,30-undecaene
• CAS: 72746-33-9
• 化学式: C₄₀H₆₀
• 分子量: 540.9
• InChiKey: BIWLELKAFXRPDE-ZURBLSRNSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  40
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (Z)-7-十四碳烯-2-酮 、 a quinone 生成 prolycopene 、 a quinol
  参考文献：
  名称：

  ?-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene

  摘要：

  The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and zeta-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9'-tricis-zeta-carotene with 15,9'-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by zeta-carotene desaturase, the 15-cis double bond of 9,15,9'-tricis-zeta-carotene has to be ( photo) isomerized to all-trans. Then, the resulting 9,9'-dicis-zeta-carotene is utilized by zeta-carotene desaturase via 7,9,9'-tricis-neurosporene to 7,9,7', 9'-tetracislycopene. Other zeta-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-zeta-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to beta-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-beta-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.

  DOI：

  10.1007/s00425-004-1395-2
• 作为产物：
  描述：

  9,15,9'-Tri-cis-zeta-carotene 生成 (Z)-7-十四碳烯-2-酮
  参考文献：
  名称：

  玉米Y9编码15-顺-ζ-胡萝卜素异构化必不可少的产物。

  摘要：

  类胡萝卜素是在植物，真菌和细菌中发现的多种色素。它们在植物中发挥重要作用，并为人类和动物带来健康益处。在植物中，人们认为将C40类胡萝卜素主链15-顺式-番茄红素转化为全反式番茄红素（下游酶所需的几何异构体）需要两种去饱和酶（并入番茄红素去饱和酶和ζ-胡萝卜素去饱和酶[ZDS]）。除光介导的15-顺-双键的光异构化外，还加上胡萝卜素异构酶（CRTISO）；细菌仅使用一种酶CRTI。玉米（Zea mays）浅黄色9（y9）基因座的特征揭示了植物类胡萝卜素生物合成所需的一种新的异构酶。我们报告说，玉米Y9编码CRTISO上游异构酶活性所需的因子，我们称之为Z-ISO，催化九氢番茄红素去饱和酶产物9,15,9'-tri-cis-zeta-胡萝卜素中15-顺式键顺式-反式转化的活性，形成9,9'-di-cis -Zeta-胡萝卜素，ZDS的底物。我们显示隐性y9等位基因条件在黑暗的组织（例如根和黄化叶）中积累9

  DOI：

  10.1104/pp.107.098996

文献信息

• Maize <i>Y9</i> Encodes a Product Essential for 15-cis-<i>ζ</i>-Carotene Isomerization
  作者：Faqiang Li、Christina Murillo、Eleanore T. Wurtzel

  DOI：10.1104/pp.107.098996

  日期：2007.6.7

  Carotenoids are a diverse group of pigments found in plants, fungi, and bacteria. They serve essential functions in plants and provide health benefits for humans and animals. In plants, it was thought that conversion of the C40 carotenoid backbone, 15-cis-phytoene, to all-trans-lycopene, the geometrical isomer required by downstream enzymes, required two desaturases (phytoene desaturase and zeta-carotene

  类胡萝卜素是在植物，真菌和细菌中发现的多种色素。它们在植物中发挥重要作用，并为人类和动物带来健康益处。在植物中，人们认为将C40类胡萝卜素主链15-顺式-番茄红素转化为全反式番茄红素（下游酶所需的几何异构体）需要两种去饱和酶（并入番茄红素去饱和酶和ζ-胡萝卜素去饱和酶[ZDS]）。除光介导的15-顺-双键的光异构化外，还加上胡萝卜素异构酶（CRTISO）；细菌仅使用一种酶CRTI。玉米（Zea mays）浅黄色9（y9）基因座的特征揭示了植物类胡萝卜素生物合成所需的一种新的异构酶。我们报告说，玉米Y9编码CRTISO上游异构酶活性所需的因子，我们称之为Z-ISO，催化九氢番茄红素去饱和酶产物9,15,9'-tri-cis-zeta-胡萝卜素中15-顺式键顺式-反式转化的活性，形成9,9'-di-cis -Zeta-胡萝卜素，ZDS的底物。我们显示隐性y9等位基因条件在黑暗的组织（例如根和黄化叶）中积累9
• Biochemical Characterization of Purified zeta-Carotene Desaturase from Anabaena PCC 7120 after Expression in Escherichia coli
  作者：Manuela Albrecht、Hartmut Linden、Gerhard Sandmann

  DOI：10.1111/j.1432-1033.1996.00115.x

  日期：1996.2.15

  A novel enzyme, ζ‐carotene desaturase from the cyanobacterium Anabaena, which catalyzes the last two steps in a series of desaturations, was overexpressed in Escherichia coli. For the first time, this allowed the purification of this enzyme and subsequent enzyme kinetic studies. The enzyme was solubilized from the E. coli membranes by Chaps and purified to homogeneity by ammonium sulfate precipitation, ion‐exchange and hydrophobic interaction chromatography. The correct translational start was confirmed by N‐terminal protein sequencing. Substrates for ζ‐carotene desaturase apart from ζ‐carotene are those carotenes which partially resemble the latter, like neurosporene and β‐zeacarotene yielding lycopene and γ‐carotene, respectively as reaction products. Also cis isomers like pro‐ζ‐carotene were converted to the correspondiong products. Km values of 10 μM were determined for both substrates ζ‐carotene and neurosporene. The enzyme was inhibited to some extent by the experimental herbicides J852 and LS80707 and also by diphenylamine which is a well‐known inhibitor of the bacterial‐type phytoene desaturase.
• ?-Carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene
  作者：J�rgen Breitenbach、Gerhard Sandmann

  DOI：10.1007/s00425-004-1395-2

  日期：2005.3

  The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and zeta-carotene desaturase revealed that 15-cis-phytoene is converted to 9,15,9'-tricis-zeta-carotene with 15,9'-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by zeta-carotene desaturase, the 15-cis double bond of 9,15,9'-tricis-zeta-carotene has to be ( photo) isomerized to all-trans. Then, the resulting 9,9'-dicis-zeta-carotene is utilized by zeta-carotene desaturase via 7,9,9'-tricis-neurosporene to 7,9,7', 9'-tetracislycopene. Other zeta-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-zeta-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to beta-carotene. The 5-cis-lycopene and the 9-cis-and 13-cis-beta-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.
• Isolation and Characterization of the <i>Z-ISO</i> Gene Encoding a Missing Component of Carotenoid Biosynthesis in Plants      
  作者：Yu Chen、Faqiang Li、Eleanore T. Wurtzel

  DOI：10.1104/pp.110.153916

  日期：2010.5.3

  Metabolic engineering of plant carotenoids in food crops has been a recent focus for improving human health. Pathway manipulation is predicated on comprehensive knowledge of this biosynthetic pathway, which has been extensively studied. However, there existed the possibility of an additional biosynthetic step thought to be dispensable because it could be compensated for by light. This step, mediated by a putative Z-ISO, was predicted to occur in the sequence of redox reactions that are coupled to an electron transport chain and convert the colorless 15-cis-phytoene to the red-colored all-trans-lycopene. The enigma of carotenogenesis in the absence of light (e.g. in endosperm, a target for improving nutritional content) argued for Z-ISO as a pathway requirement. Therefore, understanding of plant carotenoid biosynthesis was obviously incomplete. To prove the existence of Z-ISO, maize (Zea mays) and Arabidopsis (Arabidopsis thaliana) mutants were isolated and the gene identified. Functional testing of the gene product in Escherichia coli showed isomerization of the 15-cis double bond in 9,15,9′-tri-cis-ζ-carotene, proving that Z-ISO encoded the missing step. Z-ISO was found to be important for both light-exposed and “dark” tissues. Comparative genomics illuminated the origin of Z-ISO found throughout higher and lower plants, algae, diatoms, and cyanobacteria. Z-ISO evolved from an ancestor related to the NnrU (for nitrite and nitric oxide reductase U) gene required for bacterial denitrification, a pathway that produces nitrogen oxides as alternate electron acceptors for anaerobic growth. Therefore, plant carotenogenesis evolved by recruitment of genes from noncarotenogenic bacteria.

  在食品作物中代谢工程改良植物类胡萝卜素是近年来提高人类健康的重点。通路调控基于对这个生物合成通路的全面了解，这个通路已经被广泛研究。然而，存在一种被认为是可以通过光线补偿的附加生物合成步骤，因此被认为是可以省略的。这个步骤由一个假定的Z-ISO介导，预测在与电子传递链相耦合的氧化还原反应序列中发生，并将无色的15-顺-类胡萝卜烯转化为红色的全反-番茄红素。在没有光的情况下的类胡萝卜素合成之谜（例如在胚乳中，这是提高营养含量的目标）表明Z-ISO是通路所必需的。因此，对植物类胡萝卜素生物合成的理解显然是不完整的。为了证明Z-ISO的存在，分离了玉米（Zea mays）和拟南芥（Arabidopsis thaliana）突变体，并鉴定了该基因。在大肠杆菌中对基因产物进行功能测试，证明Z-ISO编码了缺失的步骤，即在9,15,9'-三顺-ζ-胡萝卜烯中异构化15-顺双键。Z-ISO对光照和“暗”组织都很重要。比较基因组揭示了Z-ISO在高等植物、低等植物、藻类、硅藻和蓝藻中的起源。Z-ISO起源于与细菌反硝化所需的NnrU（用于亚硝酸盐和一氧化氮还原酶U）基因相关的祖先，该通路产生氮氧化物作为无氧生长的替代电子受体。因此，植物类胡萝卜素合成通过从非类胡萝卜素合成细菌中招募基因而进化。