7,7,8,8,11,11,12,12-八氢-psi,psi-胡罗卜素 | 540-04-5

• 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: 7,7,8,8,11,11,12,12-八氢-psi,psi-胡罗卜素
• 中文别名: 反八氢番茄红素(含约30顺式异构体)；反八氢番茄红素 (含约30%顺式异构体)
• 英文名称: phytoene
• 英文别名: (6E,10E,14E,16E,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene；7,8,11,12,7',8'11',12'-octahydro-ψ,ψ-carotene；trans-phytoen；7,8,11,12,7',8',11',12'-octahydro-ψ,ψ-carotene；7,8,11,12,7',8',11',12'-Octahydro-τ,τ-carotin
• CAS: 540-04-5
• 化学式: C₄₀H₆₄
• 分子量: 544.948
• InChiKey: YVLPJIGOMTXXLP-KEKOKYSKSA-N

物化性质

• 沸点：
  620.3±50.0 °C(Predicted)
• 密度：
  0.865±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 物理描述：
  Solid
• 稳定性/保质期：

  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  15.3
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  7,7,8,8,11,11,12,12-八氢-psi,psi-胡罗卜素 生成 β-胡萝卜素
  参考文献：
  名称：

  SANDMANN, G.;BRAMLEY, P. M.;BOEGER, P., J. PESTIC. SCI., 1985, 10, N 1, 19-24

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (E,E,E)-geranylgeranoate 在 1,2-环氧丁烷 、 lithium aluminium tetrahydride 、 silver carbonate 作用下， 以 乙醚 、 苯 为溶剂， 生成 7,7,8,8,11,11,12,12-八氢-psi,psi-胡罗卜素
  参考文献：
  名称：

  Khan,N. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1457 - 1464

  摘要：

  DOI：
• 作为试剂：
  描述：

  geranylgeranyl diphosphate 、 7,7,8,8,11,11,12,12-八氢-psi,psi-胡罗卜素 、 Sodium phosphate, tribasic- 在 7,7,8,8,11,11,12,12-八氢-psi,psi-胡罗卜素 、 甲醇 、 ice 作用下， 反应 0.75h， 生成 phytofluene
  参考文献：
  名称：

  Herbicide-Resistant Plants, And Polynucleotides And Methods For Providing Same

  摘要：

  描述了编码突变植物类胡萝卜素脱饱和酶蛋白的核苷酸序列，这些蛋白对作用于类胡萝卜素脱饱和酶的漂白除草剂具有抗性，以及相关的核酸构建、植物和方法。

  公开号：

  US20110098180A1

文献信息

• Composition and Methods for Treating and Preventing Age-Related Macular Degeneration
  申请人：Sela Yoram

  公开号：US20090035369A1

  公开（公告）日：2009-02-05

  The present invention relates to methods and compositions effective in preventing, attenuating, inhibiting the progression of, and treating eye diseases, e.g., age-related macular degeneration (AMD). The compositions comprise, as an active ingredient, an effective amount of 3,3′-diindolylmethane (DIM) and/or its precursor indole-3-carbinol (I3C). The compositions can further comprise additional agents such as carotenoids and other phytochemicals, which produce a synergistic effect in preventing, attenuating, inhibiting the progression of, and treating AMD and other eye diseases such as glaucoma, cataracts and diabetic retinopathy (DR). The compositions are particularly effective in treating and preventing wet AMD, and in preventing or inhibiting the progression of dry AMD (non-neovascular) to wet AMD (neovascular).

  本发明涉及一种方法和组合物，其能够有效地预防、减轻、抑制进展和治疗眼部疾病，例如年龄相关性黄斑变性（AMD）。该组合物包含作为活性成分的3,3'-二吲哚甲烷（DIM）和/或其前体吲哚-3-甲醇（I3C）的有效量。该组合物还可以包括其他草本化合物，如类胡萝卜素和其他植物化学物质，这些化合物在预防、减轻、抑制进展和治疗AMD和其他眼部疾病，如青光眼、白内障和糖尿病性视网膜病变（DR）方面产生协同效应。该组合物特别适用于治疗和预防湿性AMD，并预防或抑制干性AMD（非新生血管性）向湿性AMD（新生血管性）的进展。
• Expression of a Tomato cDNA Coding for Phytoene Synthase in Escherichia coli, Phytoene Formation In Vivo and In Vitro, and Functional Analysis of the Various Truncated Gene Products1
  作者：Norihiko Misawa、Mark R. Truesdale、Gerhard Sandmann、Paul D. Fraser、Colin Bird、Wolfgang Schuch、Peter M. Bramley

  DOI：10.1093/oxfordjournals.jbchem.a124656

  日期：1994.11

  Full length and truncated cDNA expression constructs of the phytoene synthase (psy) gene from tomato have been ligated into a pUC8 cloning vector. One of the truncated constructs was introduced into Escherichia coli carrying the Erwinia uredovora GGPP synthase gene. This transformant produced 15, 15' -cis-phytoene, which was identified on the basis of its UV and IR spectral data, from geranylgeranyl diphosphate. The function of this gene product was further confirmed by in vitro assay using cell-free extract of E. coli harboring the construct. On transformation with the above constructs together with a plasmid containing the carotenoid gene cluster from E. uredovora devoid of the phytoene synthase (crtB) gene, yellow, carotenoid-containing, E. coli colonies were produced. The amounts of carotenoids synthesized by the transformed cells, related to the steady-state levels of psy mRNA, varied depending upon the psy constructs. The full-length psy clone produced 16-fold less carotenoids per unit amount of RNA than cells containing phytoene synthase without the first 114 N-terminal amino acids. Removal of further amino acids from the N-terminus caused a large decrease in carotenogenesis. A Western blot of ripe fruit stroma with a monoclonal antibody raised against phytoene synthase revealed a single protein band of apparent molecular mass 38 kDa. Based upon this immunological evidence, we conclude that the size of the transit peptide of phytoene synthase from ripe tomato fruit is approximately 9 kDa, corresponding to about 80 amino acid residues. But removal of further N-terminal amino acids up to 114 from the enzyme, to yield a protein of apparent molecular mass 34 kDa, increases its catalytic activity in E. coli.

  番茄植物烯合成酶（psy）基因的全长和截短 cDNA 表达构建体被连接到 pUC8 克隆载体中。其中一个截短的构建体被导入携带 Erwinia uredovora GGPP 合成酶基因的大肠杆菌中。该转化子产生了 15，15' -顺式植物烯，根据其紫外和红外光谱数据，确定其来自于香叶基二磷酸。利用携带该构建体的大肠杆菌的无细胞提取物进行体外检测，进一步证实了该基因产物的功能。将上述构建体与含有来自 E. uredovora 的类胡萝卜素基因簇（没有植物烯合成酶（crtB）基因）的质粒一起转化后，产生了黄色的、含有类胡萝卜素的大肠杆菌菌落。转化细胞合成类胡萝卜素的量与 psy mRNA 的稳态水平有关，因 psy 构建体而异。与含有不含前 114 个 N 端氨基酸的植物烯合成酶的细胞相比，全长 psy 克隆每单位 RNA 量产生的类胡萝卜素少 16 倍。去除 N 端更多的氨基酸会导致类胡萝卜素生成量大幅下降。用针对植物烯合成酶的单克隆抗体对成熟果实基质进行 Western 印迹，发现一条明显分子质量为 38 kDa 的蛋白质条带。根据这一免疫学证据，我们得出结论，成熟番茄果实中植物烯合成酶的转运肽大小约为 9 kDa，相当于约 80 个氨基酸残基。但从酶中去除更多的 N 端氨基酸，直至 114 个氨基酸，得到表观分子质量为 34 kDa 的蛋白质，可提高其在大肠杆菌中的催化活性。
• Polyprenols and hydroxylated lycopersenes from Myriophyllum verticillatum
  作者：Rosa Lanzetta、Pietro Monaco、Lucio Previtera、Antonella Simaldone

  DOI：10.1016/0031-9422(88)84113-x

  日期：1988.1
• Bacterial Phytoene Synthase:  Molecular Cloning, Expression, and Characterization of <i>Erwinia herbicola</i> Phytoene Synthase
  作者：Dirk Iwata-Reuyl、Shivanand K. Math、Shrivallabh B. Desai、C. Dale Poulter

  DOI：10.1021/bi0206614

  日期：2003.3.1

  Phytoene synthase (PSase) catalyzes the condensation of two molecules of geranylgeranyl diphosphate (GGPP) to give prephytoene diphosphate (PPPP) and the subsequent rearrangement of the cyclopropylcarbinyl intermediate to phytoene. These reactions constitute the first pathway specific step in carotenoid biosynthesis. The crtB gene encoding phytoene synthase was isolated from a plasmid containing the carotenoid gene cluster in Erwinia herbicola and cloned into an Escherichia coli expression system. Upon induction, recombinant phytoene synthase constituted 5-10% of total soluble protein. To facilitate purification of the recombinant enzyme, the structural gene for PSase was modified by site-directed mutagenesis to incorporate a C-terminal Glu-Glu-Phe (EEF) tripepetide to allow purification by immunoaffinity chromatography on an immobilized monoclonal anti-alpha-tubulin antibody YL1/2 column. Purified recombinant PSase-EEF gave a band at 34.5 kDa upon SDS-PAGE. Recombinant PSase-EEF was then purified to >90% homogeneity in two steps by ion-exchange and immunoaffinity chromatography. The enzyme required Mn2+ for activity, had a pH optimum of 8.2, and was strongly stimulated by detergent. The concentration of GGPP needed for half-maximal activity was similar to35 muM, and a significant inhibition of activity was seen at GGPP concentrations above 100 muM. The sole product of the reaction was 15,15'-Z-phytoene.
• Stereochemistry of trans-phytoene synthesis. Lycopersene as a carotene precursor and a mechanism for the synthesis of cis- and trans-phytoene
  作者：Donald E. Gregonis、Hans C. Rilling

  DOI：10.1021/bi00704a033

  日期：1974.3.1