9-cis-β-apo-10'-carotenal | 1372138-85-6

• 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: 9-cis-β-apo-10'-carotenal
• 英文别名: 9-cis-10'-Apo-beta-carotenal；(2E,4E,6E,8E,10E,12Z,14E)-4,9,13-trimethyl-15-(2,6,6-trimethylcyclohexen-1-yl)pentadeca-2,4,6,8,10,12,14-heptaenal
• CAS: 1372138-85-6
• 化学式: C₂₇H₃₆O
• 分子量: 376.582
• InChiKey: PJEHRCCPERVGEC-OLTPUEGQSA-N

物化性质

• 沸点：
  534.6±19.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-cis-β-apo-10'-carotenal 在 CCD₈ enzymes 作用下， 生成 carlactone
  参考文献：
  名称：

  Novel strigolactone analogues and their use

  摘要：

  化合物I的新型化合物，其用作寄生性杂草的发芽陷阱，用于分枝、分蘖和根系发育的调控，用于增强木质部生长，用于调控菌根真菌的菌丝生长以及含有化合物I和杀虫剂和/或杀菌剂的组合物。

  公开号：

  EP2518062A1
• 作为产物：
  描述：

  β-胡萝卜素 在 carotenoid cleavage dioxygenase CCD₇ 、 cis–trans isomerase Dwarf27 、 碘 、 氧气 、 iron(II) sulfate 作用下， 以 aq. phosphate buffer 、 正己烷 为溶剂， 反应 0.5h， 生成 9-cis-β-apo-10'-carotenal
  参考文献：
  名称：

  Biochemical characterization and selective inhibition of β-carotenecis-transisomerase D27 and carotenoid cleavage dioxygenase CCD8 on the strigolactone biosynthetic pathway

  摘要：

  The first three enzymatic steps of the strigolactone biosynthetic pathway catalysed by β‐carotene cis–trans isomerase Dwarf27 (D27) from Oryza sativa and carotenoid cleavage dioxygenases CCD7 and CCD8 from Arabidopsis thaliana have been reconstituted in vitro, and kinetic assays have been developed for each enzyme, in order to develop selective enzyme inhibitors. Recombinant OsD27 shows a UV‐visible λmax at 422 nm and is inactivated by silver(I) acetate, consistent with the presence of an iron–sulfur cluster that is used in catalysis. OsD27 and AtCCD7 are not inhibited by hydroxamic acids that cause shoot branching in planta, but OsD27 is partially inhibited by terpene‐like hydroxamic acids. The reaction catalysed by AtCCD8 is shown to be a two‐step kinetic mechanism using pre‐steady‐state kinetic analysis. Kinetic evidence is presented for acid–base catalysis in the CCD8 catalytic cycle and the existence of an essential cysteine residue in the CCD8 active site. AtCCD8 is inhibited in a time‐dependent fashion by hydroxamic acids D2, D4, D5 and D6 (> 95% inhibition at 100 μm) that cause a shoot branching phenotype in A. thaliana, and selective inhibition of CCD8 is observed using hydroxamic acids D13H and D15 (82%, 71% inhibition at 10 μm). The enzyme inhibition data imply that the biochemical basis of the shoot branching phenotype is due to inhibition of CCD8.

  DOI：

  10.1111/febs.13400

文献信息

• The Path from β-Carotene to Carlactone, a Strigolactone-Like Plant Hormone
  作者：Adrian Alder、Muhammad Jamil、Mattia Marzorati、Mark Bruno、Martina Vermathen、Peter Bigler、Sandro Ghisla、Harro Bouwmeester、Peter Beyer、Salim Al-Babili

  DOI：10.1126/science.1218094

  日期：2012.3.16

  compound, carlactone, which shows biological actions similar to those of strigolactone. Elucidation of the biosynthetic pathway of a new plant hormone variant that may be useful in agricultural settings is shown. Strigolactones, phytohormones with diverse signaling activities, have a common structure consisting of two lactones connected by an enol-ether bridge. Strigolactones derive from carotenoids via

  卡拉内酯 寄生巫草的发芽依赖于独脚金内酯，独脚金内酯还可以在菌根共生的背景下调节植物分枝和信号。产生独脚金内酯的生物合成途径是在类胡萝卜素生物合成中发现的，但进一步的步骤尚不清楚。阿尔德等人。 (p. 1348) 现在已经确定了一种生成独脚金内酯样化合物卡拉内酯的生化途径，该化合物显示出与独脚金内酯类似的生物作用。阐明了可能在农业环境中有用的新植物激素变体的生物合成途径。独脚金内酯是具有多种信号活性的植物激素，具有由两个通过烯醇醚桥连接的内酯组成的共同结构。独脚金内酯通过涉及类胡萝卜素裂解双加氧酶 7 和 8（CCD7 和 CCD8）以及铁结合蛋白 D27 的途径衍生自类胡萝卜素。我们证明D27是一种β-胡萝卜素异构酶，可将全反式-β-胡萝卜素转化为9-顺式-β-胡萝卜素，并被CCD7裂解为9-顺式醛。 CCD8将三个氧原子结合成9-cis-β-apo-10'-胡萝卜醛，并进行分子重排，将
• <i>MAX4</i>and<i>RMS1</i>are orthologous dioxygenase-like genes that regulate shoot branching in<i>Arabidopsis</i>and pea
  作者：Karim Sorefan、Jon Booker、Karine Haurogné、Magali Goussot、Katherine Bainbridge、Eloise Foo、Steven Chatfield、Sally Ward、Christine Beveridge、Catherine Rameau、Ottoline Leyser

  DOI：10.1101/gad.256603

  日期：2003.6.15

  Shoot branching is inhibited by auxin transported down the stem from the shoot apex. Auxin does not accumulate in inhibited buds and so must act indirectly. We show that mutations in theMAX4gene ofArabidopsisresult in increased and auxin-resistant bud growth. Increased branching inmax4shoots is restored to wild type by grafting to wild-type rootstocks, suggesting thatMAX4is required to produce a mobile branch-inhibiting signal, acting downstream of auxin. A similar role has been proposed for the pea gene,RMS1. Accordingly,MAX4andRMS1were found to encode orthologous, auxin-inducible members of the polyene dioxygenase family.

  枝梢分支是由从枝梢顶端向下运输的生长素抑制的。生长素不会在被抑制的芽中积累，因此必须间接作用。我们表明，Arabidopsis的MAX4基因突变导致芽的增长增加和对生长素的抵抗力增强。在MAx4枝条中增加的分枝通过嫁接到野生型砧木上恢复到野生型，表明MAX4需要产生一种移动的分支抑制信号，作用于生长素下游。豌豆基因RMS1也被提出了类似的作用。因此，发现MAX4和RMS1编码的是多烯双氧酶家族的同源、生长素诱导成员。
• On the substrate- and stereospecificity of the plant carotenoid cleavage dioxygenase 7
  作者：Mark Bruno、Manuel Hofmann、Martina Vermathen、Adrian Alder、Peter Beyer、Salim Al-Babili

  DOI：10.1016/j.febslet.2014.03.041

  日期：2014.5.2

  Strigolactones are phytohormones synthesized from carotenoids via a stereospecific pathway involving the carotenoid cleavage dioxygenases 7 (CCD7) and 8. CCD7 cleaves 9‐cis‐β‐carotene to form a supposedly 9‐cis‐configured β‐apo‐10′‐carotenal. CCD8 converts this intermediate through a combination of yet undetermined reactions into the strigolactone‐like compound carlactone. Here, we investigated the substrate and stereo‐specificity of the Arabidopsis and pea CCD7 and determined the stereo‐configuration of the β‐apo‐10′‐carotenal intermediate by using Nuclear Magnetic Resonance Spectroscopy. Our data unequivocally demonstrate the 9‐cis‐configuration of the intermediate. Both CCD7s cleave different 9‐cis‐carotenoids, yielding hydroxylated 9‐cis‐apo‐10′‐carotenals that may lead to hydroxylated carlactones, but show highest affinity for 9‐cis‐β‐carotene.
• MAX3/CCD7 Is a Carotenoid Cleavage Dioxygenase Required for the Synthesis of a Novel Plant Signaling Molecule
  作者：Jonathan Booker、Michele Auldridge、Sarah Wills、Donald McCarty、Harry Klee、Ottoline Leyser

  DOI：10.1016/j.cub.2004.06.061

  日期：2004.7

  Background: Plant development is exquisitely environmentally sensitive, with plant hormones acting as long-range signals that integrate developmental, genetic, and environmental inputs to regulate development. A good example of this is in the control of shoot branching, where wide variation in plant form can be generated in a single genotype in response to environmental and developmental cues.Results: Here we present evidence for a novel plant signaling molecule involved in the regulation of shoot branching. We show that the MAX3 gene of Arabidopsis is required for the production of a graft-transmissible, highly active branch inhibitor that is distinct from any of the previously characterized branch-inhibiting hormones. Consistent with its proposed function in the synthesis of a novel signaling molecule, we show that MAX3 encodes a plastidic dioxygenase that can cleave multiple carotenoids.Conclusions: We conclude that MAX3 is required for the synthesis of a novel carotenoid-derived long-range signal that regulates shoot branching.
• The Biochemical Characterization of Two Carotenoid Cleavage Enzymes from Arabidopsis Indicates That a Carotenoid-derived Compound Inhibits Lateral Branching
  作者：Steven H. Schwartz、Xiaoqiong Qin、Michele C. Loewen

  DOI：10.1074/jbc.m409004200

  日期：2004.11

  Enzymes that are able to oxidatively cleave carotenoids at specific positions have been identified in animals and plants. The first such enzyme to be identified was a nine-cis-epoxy carotenoid dioxygenase from maize, which catalyzes the rate-limiting step of abscisic acid biosynthesis. Similar enzymes are necessary for the synthesis of vitamin A in animals and other carotenoid-derived molecules in plants. In the model plant, Arabidopsis, there are nine hypothetical proteins that share some degree of sequence similarity to the nine-cis-epoxy carotenoid dioxygenases. Five of these proteins appear to be involved in abscisic acid biosynthesis. The remaining four proteins are expected to catalyze other carotenoid cleavage reactions and have been named carotenoid cleavage dioxygenases (CCDs). The hypothetical proteins, AtCCD7 and AtCCD8, are the most disparate members of this protein family in Arabidopsis. The max3 and max4 mutants in Arabidopsis result from lesions in AtCCD7 and AtCCD8. Both mutants display a dramatic increase in lateral branching and are believed to be impaired in the synthesis of an unidentified compound that inhibits axillary meristem development. To determine the biochemical function of AtCCD7, the protein was expressed in carotenoid-accumulating strains of Escherichia coli. The activity of AtCCD7 was also tested in vitro with several of the most common plant carotenoids. It was shown that the recombinant AtCCD7 protein catalyzes a specific 9-10 cleavage of beta-carotene to produce the 10'-apo-beta-carotenal (C-27) and beta-ionone (C-13). When AtCCD7 and AtCCD8 were co-expressed in a beta-carotene-producing strain of E. coli, the 13-apo-beta-carotenone (C-18) was produced. The C-18 product appears to result from a secondary cleavage of the AtCCD7-derived C-27 product. The sequential cleavages of beta-carotene by AtCCD7 and AtCCD8 are likely the initial steps in the synthesis of a carotenoid-derived signaling molecule that is necessary for the regulation lateral branching.