圆酵母素 | 547-23-9

• 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: 圆酵母素
• 中文别名: 红酵母烯
• 英文名称: torulene
• 英文别名: 2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E,21E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,21,23-dodecaenyl]-1,3,3-trimethylcyclohexene
• CAS: 547-23-9
• 化学式: C₄₀H₅₄
• 分子量: 534.869
• InChiKey: AIBOHNYYKWYQMM-MXBSLTGDSA-N

物化性质

• 熔点：
  183-184 °C
• 沸点：
  669.6±22.0 °C(Predicted)
• 密度：
  0.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  圆酵母素 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 Dehydrotorulen
  参考文献：
  名称：

  Hertzberg; Liaaen Jensen, Acta Chemica Scandinavica (1947), 1967, vol. 21, # 1, p. 15 - 41

  摘要：

  DOI：
• 作为产物：
  描述：

  (3'Z,5'Z)-torulene 在 碘 作用下， 生成 圆酵母素
  参考文献：
  名称：

  Sterically hindered carotenoids with 3Z, 5Z configuration from the seeds of oriental bitter sweet, Celastrus orbiculatus

  摘要：

  Sterically hindered cis-carotenoids 1 and 2 were isolated from seeds of the oriental bitter sweet, Celastrus orbiculatus. Their structures were determined to be (3'Z, 5'Z)-celaxanthin and (3'Z, 5'Z)-torulene, respectively, on the basis of spectroscopic data and iodine-catalyzed stereomutation. This is the first report on carotenoids with a 3Z, 5Z configuration. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.04.018

文献信息

• 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
• Identification and biochemical characterization of a novel carotenoid oxygenase: elucidation of the cleavage step in the Fusarium carotenoid pathway
  作者：Alfonso Prado-Cabrero、Alejandro F. Estrada、Salim Al-Babili、Javier Avalos

  DOI：10.1111/j.1365-2958.2007.05665.x

  日期：——

  SummaryThe synthesis of the acidic apo‐carotenoid neurosporaxanthin by the fungus Fusarium fujikuroi depends on four enzyme activities: phytoene synthase and carotene cyclase, encoded by the bifunctional gene carRA, a carotene desaturase, encoded by carB, and a postulated cleaving enzyme converting torulene (C40) into neurosporaxanthin (C35). Based on sequence homology to carotenoid oxygenases, we identified the novel fungal enzyme CarT. Sequencing of the carT allele in a torulene‐accumulating mutant of F. fujikuroi revealed a mutation affecting a highly conserved amino acid, and introduction of a heterologous carT gene in this mutant restored the ability to produce neurosporaxanthin, pointing to CarT as the enzyme responsible for torulene cleavage. Expression of carT in lycopene‐accumulating E. coli cells resulted in the formation of minor amounts of apo‐carotenoids, but no enzymatic activity was observed in β‐carotene‐accumulating cells, indicating a preference for acyclic or monocyclic carotenes. The purified CarT enzyme efficiently cleaved torulene in vitro to produce β‐apo‐4′‐carotenal, the aldehyde corresponding to the acidic neurosporaxanthin, and was also active on other monocyclic synthetic substrates. In agreement with its role in carotenoid biosynthesis, the carT transcript levels are induced by light and upregulated in carotenoid‐overproducing mutants, as already found for other car genes.
• Identification of the gene responsible for torulene cleavage in the Neurospora carotenoid pathway
  作者：Lorena Saelices、Loubna Youssar、Iris Holdermann、Salim Al-Babili、Javier Avalos

  DOI：10.1007/s00438-007-0269-2

  日期：2007.11

  Torulene, a C-40 carotene, is the precursor of the end product of the Neurospora carotenoid pathway, the C-35 xanthophyll neurosporaxanthin. Torulene is synthesized by the enzymes AL-2 and AL-1 from the precursor geranylgeranyl diphosphate and then cleaved by an unknown enzyme into the C-35 apocarotenoid. In general, carotenoid cleavage reactions are catalyzed by carotenoid oxygenases. Using protein data bases, we identified two putative carotenoid oxygenases in Neurospora, named here CAO-1 and CAO-2. A search for novel mutants of the carotenoid pathway in this fungus allowed the identification of two torulene-accumulating strains, lacking neurosporaxanthin. Sequencing of the cao-2 gene in these strains revealed severe mutations, pointing to a role of CAO-2 in torulene cleavage. This was further supported by the identical phenotype found upon targeted disruption of cao-2. The biological function was confirmed by in vitro assays using the purified enzyme, which cleaved torulene to produce ss-apo-4'-carotenal, the corresponding aldehyde of neurosporaxanthin. The specificity of CAO-2 was shown by the lack of gamma-carotene-cleaving activity in vitro. As predicted for a structural gene of the carotenoid pathway, cao-2 mRNA was induced by light in a WC-1 and WC-2 dependent manner. Our data demonstrate that CAO-2 is the enzyme responsible for the oxidative cleavage of torulene in the neurosporaxanthin biosynthetic pathway.
• Hertzberg; Liaaen Jensen, Acta Chemica Scandinavica (1947), 1967, vol. 21, # 1, p. 15 - 41
  作者：Hertzberg、Liaaen Jensen

  DOI：——

  日期：——
• Sterically hindered carotenoids with 3Z, 5Z configuration from the seeds of oriental bitter sweet, Celastrus orbiculatus
  作者：Takashi Maoka

  DOI：10.1016/j.phytochem.2009.04.018

  日期：2009.5

  Sterically hindered cis-carotenoids 1 and 2 were isolated from seeds of the oriental bitter sweet, Celastrus orbiculatus. Their structures were determined to be (3'Z, 5'Z)-celaxanthin and (3'Z, 5'Z)-torulene, respectively, on the basis of spectroscopic data and iodine-catalyzed stereomutation. This is the first report on carotenoids with a 3Z, 5Z configuration. (C) 2009 Elsevier Ltd. All rights reserved.