beta,epsilon-胡罗卜素 | 432-70-2

• 物质功能分类: 生物 - 生化试剂盒
• 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: beta,epsilon-胡罗卜素
• 中文别名: 3-吡啶甲醇,a-(溴甲基)-,(aS)-
• 英文名称: alpha-carotene
• 英文别名: α-carotene；1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-2-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohexene；all-trans-α-carotene；β,ε-carotene；(all-E)-α-carotene；β-carotene；all-trans-alpha-Carotene
• CAS: 432-70-2
• 化学式: C₄₀H₅₆
• 分子量: 536.885
• InChiKey: ANVAOWXLWRTKGA-JLTXGRSLSA-N

物化性质

• 沸点：
  644.9±35.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）
• 最大波长(λmax)：
  λ: 445-449 nm Amax
• LogP：
  15.138 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  2.0
• 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：

  beta,epsilon-胡罗卜素 生成 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Polgar; Zechmeister, Journal of the American Chemical Society, 1944, vol. 66, p. 189,190

  摘要：

  DOI：
• 作为产物：
  描述：

  15,15'-didehydro-12'-apo-β-caroten-12'-al 生成 beta,epsilon-胡罗卜素
  参考文献：
  名称：

  类胡萝卜素中的合成物。17.米特隆。γ-胡萝卜素sowie d，升-α-UNDβ胡萝卜素AUS脱氢-β-APO-12'-carotinal（C 25）

  摘要：

  γ-胡萝卜素（mp 153°）通过脱氢-β-apo-l2'-胡萝卜素（C 25）（V）与伪亚亚乙基乙基三苯基氯化chloride（IV）的WITTIG反应合成（C 25 + C 15＝ C 40）或β-apo-8′-胡萝卜素（C 30）（VII）与香叶基三苯基溴化phosph（VIII）（C 30 + C 10＝ C 40）。

  DOI：

  10.1002/hlca.19610440414

文献信息

• α-Carotin-mono-epoxyd und Flavochrom
  作者：P. Karrer、E. Jucker

  DOI：10.1002/hlca.660280166

  日期：——

  No abstract is available for this article.

  本文没有摘要。
• Umwandlung von ?-Carotin in ?-Carotin und von Xanthophyll in Zeaxanthin
  作者：P. Karrer、E. Jucker

  DOI：10.1002/hlca.19470300129

  日期：1947.2.1

  No abstract is available for this article.

  本文没有摘要。
• Molecular Cloning and Characterization of Carotenoid Pathway Genes and Carotenoid Content in Ixeris dentata var. albiflora
  作者：Chinreddy Subramanyam Reddy、Sang-Hoon Lee、Jeong Su Yoon、Jae Kwang Kim、Sang Won Lee、Mok Hur、Sung Cheol Koo、Jin Meilan、Woo Moon Lee、Jae Ki Jang、Yoonkang Hur、Sang Un Park、and Yeon Bok Kim

  DOI：10.3390/molecules22091449

  日期：——

  Ixeris dentata var. albiflora is considered as a potential therapeutic agent against mithridatism, calculous, indigestion, pneumonia, hepatitis, and tumors as well as good seasoned vegetable in Far East countries. Phytoene synthase (PSY), phytoene desaturase (PDS) ξ-carotene desaturase (ZDS), lycopene β-cyclase (LCYB), lycopene ε-cyclase (LCYE), ε-ring carotene hydroxylase (CHXB), and zeaxanthin epoxidase (ZDS) are vital enzymes in the carotenoid biosynthesis pathway. We have examined these seven genes from I. dentata that are participated in carotenoid biosynthesis utilizing an Illumina/Solexa HiSeq 2000 platform. In silico analysis of the seven deduced amino acid sequences were revealed its closest homology with other Asteracea plants. Further, we explored transcript levels and carotenoid accumulation in various organs of I. dentata using quantitative real time PCR and high-performance liquid chromatography, respectively. The highest transcript levels were noticed in the leaf for all the genes while minimal levels were noticed in the root. The maximal carotenoid accumulation was also detected in the leaf. We proposed that these genes expressions are associated with the accumulation of carotenoids. Our findings may suggest the fundamental clues to unravel the molecular insights of carotenoid biosynthesis in various organs of I. dentata.

  Ixeris dentata var. albiflora 被认为是远东国家潜在的治疗剂，可用于治疗毒物症、结石、消化不良、肺炎、肝炎和肿瘤，同时也是一种美味的时令蔬菜。植物类胡萝卜素合成途径中的重要酶包括：植物类胡萝卜素合成酶（PSY）、植物类胡萝卜素去饱和酶（PDS）、ξ-类胡萝卜素去饱和酶（ZDS）、番茄红素β-环化酶（LCYB）、番茄红素ε-环化酶（LCYE）、ε-环类胡萝卜素羟化酶（CHXB）和玉米黄质环氧化酶（ZDS）。我们利用Illumina/Solexa HiSeq 2000平台检测了I. dentata中参与类胡萝卜素合成的这七个基因。通过对这七个基因编码的氨基酸序列进行计算机分析，发现其与其他菊科植物最为相似。此外，我们还利用实时荧光定量PCR和高效液相色谱法分别研究了I. dentata各器官的转录水平和类胡萝卜素积累情况。所有基因中叶片的转录水平最高，而根部的转录水平最低。最大的类胡萝卜素积累也在叶片中检测到。我们认为这些基因的表达与类胡萝卜素的积累有关。我们的发现可能为揭示I. dentata各器官类胡萝卜素合成的分子机制提供基础线索。
• The <i>Arabidopsis LUT1</i> locus encodes a member of the cytochrome P450 family that is required for carotenoid ε-ring hydroxylation activity
  作者：Li Tian、Valeria Musetti、Joonyul Kim、Maria Magallanes-Lundback、Dean DellaPenna

  DOI：10.1073/pnas.2237237100

  日期：2004.1.6

  Lutein, a dihydroxy xanthophyll, is the most abundant carotenoid in plant photosynthetic tissues and plays crucial structural and functional roles in the light-harvesting complexes. Carotenoid β-and ε-hydroxylases catalyze the formation of lutein from α-carotene (β,ε-carotene). In contrast to the well studied β-hydroxylases that have been cloned and characterized from many organisms, the ε-hydroxylase has only been genetically defined by the lut1 mutation in Arabidopsis . We have isolated the LUT1 gene by positional cloning and found that, in contrast to all known carotenoid hydroxylases, which are the nonheme diiron monooxygenases, LUT1 encodes a cytochrome P450-type monooxygenase, CYP97C1. Introduction of a null mutant allele of LUT1, lut1 - 3 , into the β-hydroxylase 1/β-hydroxylase 2 ( b1 b2 ) double-mutant background, in which both Arabidopsis β-hydroxylases are disrupted, yielded a genotype ( lut1 - 3 b1 b2 ) in which all three known carotenoid hydroxylase activities are eliminated. Surprisingly, hydroxylated β-rings were still produced in lut1 - 3 b1 b2 , suggesting that a fourth unknown carotenoid β-hydroxylase exists in vivo that is structurally unrelated to β-hydroxylase 1 or 2. A second chloroplast-targeted member of the CYP97 family, CYP97A3, is 49% identical to LUT1 and hypothesized as a likely candidate for this additional β-ring hydroxylation activity. Overall, LUT1 defines a class of carotenoid hydroxylases that has evolved independently from and uses a different mechanism than nonheme diiron β-hydroxylases.

  叶黄素是一种二羟基黄酮类，是植物光合组织中最丰富的类胡萝卜素，并在光收集复合体中发挥关键的结构和功能作用。类胡萝卜素β-和ε-羟化酶催化α-胡萝卜素（β,ε-胡萝卜素）转化为叶黄素。与已从许多生物体中克隆和表征的β-羟化酶相反，ε-羟化酶仅通过在拟南芥中的lut1突变基因进行遗传定义。我们通过位置克隆分离了LUT1基因，并发现，与所有已知的类胡萝卜素羟化酶不同的是，它是一种细胞色素P450型单加氧酶，CYP97C1。将lut1-3的空突变等位基因引入β-羟化酶1 / β-羟化酶2（b1 b2）双突变体背景中，其中两种拟南芥β-羟化酶均被破坏，得到了一个基因型（lut1-3 b1 b2），其中所有已知的三种类胡萝卜素羟化酶活性被消除。令人惊讶的是，lut1-3 b1 b2中仍产生羟基化的β-环，这表明在体内存在第四种不同于β-羟化酶1或2的未知类胡萝卜素β-羟化酶。CYP97家族的第二个叶绿体定位成员CYP97A3与LUT1相似度为49％，被假设为这种额外的β-环羟化活性的可能候选者。总体而言，LUT1定义了一类独立进化且使用不同机制于非血红素二铁β-羟化酶的类胡萝卜素羟化酶。
• The Evolution and Function of Carotenoid Hydroxylases in Arabidopsis
  作者：Joonyul Kim、James J. Smith、Li Tian、Dean DellaPenna

  DOI：10.1093/pcp/pcp005

  日期：2009.3

  To gain insight into the evolution of xanthophyll synthesis in Arabidopsis thaliana, we analyzed two pairs of duplicated carotenoid hydroxylase enzymes in Arabidopsis thaliana: the cytochrome P450 enzymes CYP97A3 and CYP97C1, and non-heme di-iron enzymes, BCH1 and BCH2. Hydroxylated carotenes did not accumulate in a quadruple mutant for these four genes, demonstrating that they encode the full complement of carotenoid hydroxylases in A. thaliana. We were thus able to infer definitively the activity of each enzyme in vivo based on the phenotypes of selected double and triple mutant genotypes. The CYP97 and BCH gene pairs are primarily responsible for hydroxylation of α- and β-carotenes, respectively, but exhibit some overlapping activities, most notably in hydroxylation of the β-ring of α-carotene. Surprisingly, triple mutants containing only CYP97C1 or CYP97A3 activity produced 74 and 6% of the wild-type lutein level, indicating that CYP97C1 can efficiently hydroxylate both the β- and ε-rings of α-carotene and that CYP97A3 also has low activity toward the ε-ring of α-carotene. The modes of functional divergence for the gene pairs appear distinct, with the CYP97 duplicates being strongly co-expressed but encoding enzymes with different in vivo substrates, while the BCH duplicates encode isozymes that show significant expression divergence in reproductive organs. By integrating the evolutionary history and substrate specificities of each extant enzyme with the phenotypic responses of various mutant genotypes to high light stress, we propose two likely scenarios for the evolution of α-xanthophyll biosynthesis in plants from ancestral organisms.

  为了深入了解拟南芥中叶黄素合成的进化过程，我们分析了拟南芥中两对重复的类胡萝卜素羟化酶：细胞色素P450酶CYP97A3和CYP97C1，以及非血红素二铁酶BCH1和BCH2。在四种基因的四重突变体中，羟化类胡萝卜素不会累积，这表明它们编码了拟南芥中类胡萝卜素羟化酶的全部基因。因此，我们能够根据选定的双突变体和三重突变体的表型，明确推断每种酶在体内的活性。CYP97和BCH基因对分别主要负责α-和β-胡萝卜素的羟化作用，但表现出一些重叠活性，最明显的是在α-胡萝卜素的β-环的羟化作用。令人惊讶的是，仅包含CYP97C1或CYP97A3活性的三重突变体产生的叶黄素水平分别为野生型的74%和6%，这表明CYP97C1能够有效地羟化α-胡萝卜素的β-环和ε-环，而CYP97A3对α-胡萝卜素的ε-环也有低活性。基因对的功能分化模式似乎不同，CYP97重复基因强烈共表达，但编码具有不同体内底物的酶，而BCH