(6E,8E,10Z,12E,14Z,16E,18Z,20E,22E,26E)-2,6,10,14,19,23,27,31-八甲基三十二碳-2,6,8,10,12,14,16,18,20,22,26,30-十二烯 | 502-64-7

• 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: (6E,8E,10Z,12E,14Z,16E,18Z,20E,22E,26E)-2,6,10,14,19,23,27,31-八甲基三十二碳-2,6,8,10,12,14,16,18,20,22,26,30-十二烯
• 中文别名: 链孢红素
• 英文名称: all-trans-neurosporene
• 英文别名: neurosporene；7,8-dihydro-ψ,ψ-carotene；(6E,8E,10E,12E,14E,16E,18E,20E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,26,30-dodecaene
• CAS: 502-64-7
• 化学式: C₄₀H₅₈
• 分子量: 538.901
• InChiKey: ATCICVFRSJQYDV-XILUKMICSA-N

物化性质

• 沸点：
  650.7±40.0 °C(Predicted)
• 密度：
  0.882±0.06 g/cm3(Predicted)
• 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：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (6E,8E,10Z,12E,14Z,16E,18Z,20E,22E,26E)-2,6,10,14,19,23,27,31-八甲基三十二碳-2,6,8,10,12,14,16,18,20,22,26,30-十二烯 生成 7',8'-dihydro-β,ψ-carotene
  参考文献：
  名称：

  The Carotenoid 7, 8-Dihydro-psi end Group can be Cyclized by the Lycopene Cyclases from the Bacterium Erwinia Uredovora and the Higher Plant Capsicum Annuum

  摘要：

  The genes for geranylgeranyl diphosphate synthase (crtE) and phytoene synthase (crtB) from the epiphytic bacterium Erwinia uredovora and the phytoene desaturase gene from the photosynthetic bacterium Rhodobacter capsulatus (Rc‐crtI) were introduced into Escherichia coli, which resulted in the accumulation of the acyclic carotenoid, neurosporene. Further introduction of the lycopene cyclase gene from E. uredovora (crtY) or the higher plant Capsicum annuum (Icy) resulted in the production of a bicyclic carotenoid, 7,8‐dihydro‐β‐carotene, via monocyclic β‐zeacarotene. ζ‐Carotene was also found to be cyclized to bicyclic 7,8,7′,8′‐tetrahydro‐β‐carotene by the Erwinia cyclase. These results indicate that both lycopene cyclases can cyclize a 7,8‐dihydro‐ψ end group to a 7,8‐dihydro‐β end group, in addition to the usual cyclization of the ψ end group to the β end group. Furthermore, β‐carotene hydroxylase from Enwnia (CrtZ) was able to add a hydroxyl group to the 7,8‐dihydro‐β end group and the β end group.

  DOI：

  10.1111/j.1432-1033.1996.0291t.x
• 作为产物：
  描述：

  (2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate 在 N,N-二甲基丙烯基脲 、 氢氧化钾 、 二苯并-18-冠醚-6 、 正丁基锂 、 sodium methylate 、 sodium 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 氨 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 31.03h， 生成 (6E,8E,10Z,12E,14Z,16E,18Z,20E,22E,26E)-2,6,10,14,19,23,27,31-八甲基三十二碳-2,6,8,10,12,14,16,18,20,22,26,30-十二烯
  参考文献：
  名称：

  合成胡萝卜素-端基和（Z）-修饰末端的多巴宾登根

  摘要：

  末端共轭双键具有ψ-端基和（Z）-构型的胡萝卜素的合成

  DOI：

  10.1002/hlca.19850680604

文献信息

• Carotenoids and related compounds. Part XV. The structure and synthesis of phytoene, phytofluene, ζ-carotene, and neurosporene
  作者：J. B. Davis、L. M. Jackman、P. T. Siddons、B. C. L. Weedon

  DOI：10.1039/j39660002154

  日期：——

  Structures have been established for the polyenes, phytoene, phytofluene, ζ-carotene and neurosporene by spectral studies and synthesis. The stereochemistry of these polyenes is discussed.

  通过光谱研究和合成，已经建立了多烯，八氢番茄红素，八氢番茄红素，ζ-胡萝卜素和神经孢子烯的结构。讨论了这些多烯的立体化学。
• Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
  申请人：Cardax Pharmaceuticals, Inc.

  公开号：US07375133B2

  公开（公告）日：2008-05-20

  A method for inhibiting and/or ameliorating the occurrence of diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals in a subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The analog or derivative is administered such that the subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include a pharmaceutical composition including a carotenoid analog or derivative. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ether functionality. In some embodiments, a pharmaceutical composition may include a biologically inactive carrier. The pharmaceutical composition may be adapted to be administered to a human subject.

  一种抑制和/或改善与反应性氧化物种、反应性氮物种、自由基和/或非自由基有关的疾病发生的方法，其中给予受试者类胡萝卜素类似物或衍生物，单独或与另一类胡萝卜素类似物或衍生物或共同抗氧化剂配方结合使用。该类似物或衍生物的给予使得受试者发生与反应性氧化物种、反应性氮物种、自由基和/或非自由基有关的疾病的风险减少。该类似物或类似物组合可用于抑制和/或改善任何涉及反应性氧化物种、反应性氮物种、自由基和/或非自由基产生的疾病。在某些实施例中，该发明可能包括包括类胡萝卜素类似物或衍生物的药物组合物。类胡萝卜素类似物可能包括具有7到14个双键的共轭多烯。共轭多烯可能包括至少一个取代基的环状环。在某些实施例中，类胡萝卜素类似物或衍生物的环状环中可能包括至少一个取代基。该取代基可能通过醚功能与环状环耦合。在某些实施例中，药物组合物可能包括生物学上不活性的载体。该药物组合物可能适用于人类受试者的给予。
• A Single Five-Step Desaturase Is Involved in the Carotenoid Biosynthesis Pathway to β-Carotene and Torulene in Neurospora crassa
  作者：Alexander Hausmann、Gerhard Sandmann

  DOI：10.1006/fgbi.2000.1212

  日期：2000.7

  related bacterial enzymes, the cofactor involved in the dehydrogenation reaction was NAD for Al-1. In situ competition with a neurosporene- and lycopene-converting hydratase and cyclase indicated that these enzymes can divert intermediates of the desaturation sequence. Based on the in vitro and in vivo results, the organization of the phytoene desaturase from N. crassa was proposed as an assembly of identical

  在大肠杆菌中表达了来自神经孢霉的植物烯去饱和酶Al-1，并分离了一种活性酶，该酶催化了多达五个双键逐步引入底物八氢番茄红素中。主要反应产物是3，4-二氢番茄红素和番茄红素。Al-1还接受了几种去饱和中间体，ζ-胡萝卜素，神经孢子烯和番茄红素。与结构相关的细菌酶相反，参与脱氢反应的辅因子是Al-1的NAD。与转化神经孢子和番茄红素的水合酶和环化酶的原位竞争表明，这些酶可以转移去饱和序列的中间体。根据体外和体内结果，从N中组织八氢番茄红素去饱和酶。提出了crassa作为负责多步反应的相同蛋白质单元的组装。但是，空间布置应足够宽松，以允许单个中间体在进出该复合体的两个方向上进行交换。由于Al-1不接受γ-胡萝卜素作为底物，因此，甲苯的形成必须仅通过3,4-二氢番茄红素的环化来进行。
• Novel apocarotenoid intermediates in Neurospora crassa mutants imply a new biosynthetic reaction sequence leading to neurosporaxanthin formation
  作者：Alejandro F. Estrada、Dominic Maier、Daniel Scherzinger、Javier Avalos、Salim Al-Babili

  DOI：10.1016/j.fgb.2008.09.001

  日期：2008.11

  Neurosporaxanthin, beta-apo-4'-carotenoic acid (C35), represents the end-product of the carotenoid pathway in Neurospora crassa. It is supposed to be synthesized in three steps catalyzed by sequential AL-2, CAO-2 and YLO-1 activities: (i) cyclization of 3,4-didehydrolycopene (C40); (ii) cleavage of torulene into beta-apo-4'-carotenal (C35); and finally (iii) oxidation of beta-apo-4'-carotenal. However

  Neurosporaxanthin，β-apo-4'-胡萝卜酸（C35）代表了Neurospora crassa中类胡萝卜素途径的终产物。据推测，它是由连续的AL-2，CAO-2和YLO-1活性催化的三个步骤合成的：（i）3,4-二氢番茄红素（C40）的环化；（ii）将甲苯裂解为β-apo-4'-胡萝卜素（C35）；最后（iii）氧化β-apo-4'-胡萝卜素。但是，对ylo-1突变体的分析揭示了除β-apo-4'-胡萝卜素以外的中间体的积累。在这里，我们生成了一个3,4-二氢番茄红素积聚的大肠杆菌菌株，并表明CAO-2在体内和体外裂解了这种无环胡萝卜素，产生了apo-4'-lycopenal。然后将ylo-1突变体中积累的阿朴类胡萝卜素鉴定为apo-4'-lycopenal和apo-4'-lycopenol，指出前者是YLO-1底物，并表明环化是神经孢黄质生物合成的最后一步。通过分析缺乏
• Biochemical characterization of the carotenoid 1,2-hydratases (CrtC) from Rubrivivax gelatinosus and Thiocapsa roseopersicina
  作者：Aida Hiseni、Isabel W. C. E. Arends、Linda G. Otten

  DOI：10.1007/s00253-011-3324-1

  日期：2011.8

  polyacrylamide gel electrophoresis analysis revealed two protein bands of 44 and 38 kDa for TrCrtC, which indicate protein processing. Both hydratases are also able to convert the unnatural substrate geranylgeraniol (C20 substrate), which functionally resembles the natural substrate lycopene.

  来自光合细菌 Rubrivivax gelatinosus 和 Thiocapsa roseopersicina 的两个类胡萝卜素 1,2-水合酶 (CrtC) 基因被克隆并在大肠杆菌中以活性形式表达，并通过亲和层析进行纯化。研究了重组酶的生化特性及其底物​​特异性。纯化的 CrtCs 独立地催化辅助因子将番茄红素转化为 1-H2O-和 1,1'-( )(2)-番茄红素。水合酶活性的最佳 pH 值和温度分别为 8.0 和 30°C。番茄红素水合获得的表观 K (m) 和 V (max) 值为 24 μM 和 0.31 nmol h(-1) mg(-1)，对于 RgCrtC 和 9.5 μM 和 0.15 nmol h(-1) mg(- 1) 分别为 TrCrtC。十二烷基硫酸钠聚丙烯酰胺凝胶电泳分析显示 TrCrtC 有两条 44 kDa 和 38 kDa 的蛋白质条带，这表明蛋白质加