6-deoxotyphasterol | 164034-47-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6-deoxotyphasterol
• 英文别名: (2S,3R,4R,5S)-2-[(3R,5S,8R,9S,10S,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5,6-dimethylheptane-3,4-diol
• CAS: 164034-47-3
• 化学式: C₂₈H₅₀O₃
• 分子量: 434.703
• InChiKey: WPHVOXMMNSLJSF-DAWJDVIISA-N

物化性质

• 沸点：
  551.4±20.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-deoxotyphasterol 在 <2H6>6-deoxosterone 、 cultured cells (V₂₀₈) of Catharanthus roseus 作用下， 反应 24.0h， 生成 6-deoxo-castasteron
  参考文献：
  名称：

  An alternative brassinolide biosynthetic pathway via late C-6 oxidation

  摘要：

  DOI：

  10.1016/s0031-9422(96)00572-9
• 作为产物：
  描述：

  6-deoxoteasterone 在 palladium on activated charcoal 吡啶 、 二环己烷并-18-冠醚-6 、 potassium superoxide 、 氢氧化钾 、 氢气 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 6-deoxotyphasterol
  参考文献：
  名称：

  Takatsuto, Suguru; Watanabe, Tsuyoshi; Fujioka, Shozo, Journal of Chemical Research, Miniprint, 1997, # 4, p. 901 - 924

  摘要：

  DOI：

文献信息

• C-23 Hydroxylation by<i>Arabidopsis</i>CYP90C1 and CYP90D1 Reveals a Novel Shortcut in Brassinosteroid Biosynthesis
  作者：Toshiyuki Ohnishi、Anna-Maria Szatmari、Bunta Watanabe、Satomi Fujita、Simona Bancos、Csaba Koncz、Marcel Lafos、Kyomi Shibata、Takao Yokota、Kanzo Sakata、Miklos Szekeres、Masaharu Mizutani

  DOI：10.1105/tpc.106.045443

  日期：2006.12.14

  Brassinosteroids (BRs) are biosynthesized from campesterol via several cytochrome P450 (P450)–catalyzed oxidative reactions. We report the functional characterization of two BR-biosynthetic P450s from Arabidopsis thaliana: CYP90C1/ROTUNDIFOLIA3 and CYP90D1. The cyp90c1 cyp90d1 double mutant exhibits the characteristic BR-deficient dwarf phenotype, although the individual mutants do not display this phenotype. These data suggest redundant roles for these P450s. In vitro biochemical assays using insect cell-expressed proteins revealed that both CYP90C1 and CYP90D1 catalyze C-23 hydroxylation of various 22-hydroxylated BRs with markedly different catalytic efficiencies. Both enzymes preferentially convert 3-epi-6-deoxocathasterone, (22S,24R)-22-hydroxy-5α-ergostan-3-one, and (22S,24R)-22-hydroxyergost-4-en-3-one to 23-hydroxylated products, whereas they are less active on 6-deoxocathasterone. Likewise, cyp90c1 cyp90d1 plants were deficient in 23-hydroxylated BRs, and in feeding experiments using exogenously supplied intermediates, only 23-hydroxylated BRs rescued the growth deficiency of the cyp90c1 cyp90d1 mutant. Thus, CYP90C1 and CYP90D1 are redundant BR C-23 hydroxylases. Moreover, their preferential substrates are present in the endogenous Arabidopsis BR pool. Based on these results, we propose C-23 hydroxylation shortcuts that bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5α-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol.

  植物雄甾体（BRs）是通过几个细胞色素P450（P450）催化的氧化反应从肉豆蔻甾醇合成的。我们报道了来自拟南芥的两个BR生物合成P450的功能特征：CYP90C1 / ROTUNDIFOLIA3和CYP90D1。cyp90c1 cyp90d1双突变体表现出特征性的BR缺陷侏儒表型，尽管单个突变体不显示此表型。这些数据表明这些P450具有冗余作用。使用昆虫细胞表达的蛋白质进行体外生化分析表明，CYP90C1和CYP90D1均催化各种22-羟基BR的C-23羟化，具有明显不同的催化效率。两种酶优先将3-epi-6-deoxocathasterone，（22S，24R）-22-羟基-5α-ergostan-3-one和（22S，24R）-22-羟基ergost-4-en-3-one转化为23-羟基产物，而它们对6-deoxocathasterone的活性较低。同样，cyp90c1 cyp90d1植物缺乏23-羟基BR，在使用外源中间体进行喂养实验时，只有23-羟基BR才能挽救cyp90c1 cyp90d1突变体的生长缺陷。因此，CYP90C1和CYP90D1是冗余的BR C-23羟化酶。此外，它们的优先底物存在于内源的拟南芥BR池中。基于这些结果，我们提出C-23羟化捷径，可以绕过肉豆蔻醇，6-deoxocathasterone和6-deoxoteasterone，直接从（22S，24R）-22-羟基-5α-ergostan-3-one和3-epi-6-deoxocathasterone到3-dehydro-6-deoxoteasterone和6-deoxotyphasterol。

• Cytochrome P450 hydroxylase, an important enzyme in brassinosteroid biosynthesis of plants
  申请人：Korea Kumho Petrochemical Co. Ltd.

  公开号：EP1209227A2

  公开（公告）日：2002-05-29

  The present invention provides a nucleic acid molecule encoding a dark-inducible cytochrome P450 hydroxylase that catalyzes the brassinosteroid biosynthesis through C-2 hydroxylations in plants. The invention also describes the methods and processes for generating expression cassettes and plasmids and for the use of these expression cassettes and plasmids to synthesize the cytochrome P450 hydroxylase or biologically active fragments of such an enzyme. The invention can be utilized to improve or decrease the stem growth of transgenic plants containing the nucleic acid molecule so that they exhibit improved growth rate and resistance to environmental stress and to identify other proteins involved in the brassinosteroid biosynthesis and in the plant growth regulation.

  本发明提供了一种编码暗诱导细胞色素P450羟化酶的核酸分子，该酶通过C-2羟化作用催化植物中铜绿素的生物合成。本发明还描述了生成表达盒和质粒以及使用这些表达盒和质粒合成细胞色素 P450 羟化酶或这种酶的生物活性片段的方法和过程。本发明可用于改善或降低含有核酸分子的转基因植物的茎部生长，使其表现出更好的生长速度和对环境胁迫的抵抗力，还可用于鉴定参与铜绿素生物合成和植物生长调节的其他蛋白质。
• GENE CONCERNING BRASSINOSTEROID-SENSITIVITY OF PLANTS AND UTILIZATION THEREOF
  申请人：National Institute of Agrobiological Sciences

  公开号：EP1275719A1

  公开（公告）日：2003-01-15

  The present inventors successfully produced rice dwarf mutant d61 and also isolated the OsBRI1 gene which corresponds to a region in the d61 locus. OsBRI1 is found to increase plant brassinosteroid sensitivity. Moreover, the present inventors showed that OsBRI1 functions in growth and development process of- rice, such as, internode elongation by inducing internode cell elongation and the inclination of the lamina joint. By introducing antisense nucleotides or dominant negative of OsBRI1, the present inventors produced transgenic rice plants whose phenotype was modified.

  本发明人成功培育出水稻矮秆突变体 d61，并分离出与 d61 基因座中一个区域相对应的 OsBRI1 基因。研究发现，OsBRI1 能提高植物对黄铜类固醇的敏感性。此外，本发明人还发现 OsBRI1 在水稻的生长发育过程中起作用，如通过诱导节间细胞伸长和叶片关节倾斜来实现节间伸长。通过引入 OsBRI1 的反义核苷酸或显性阴性，本发明人培育出了表型发生改变的转基因水稻植株。
• Screening method for identifying genes involved in plant cell cycle
  申请人：VIB VZM

  公开号：EP2527451A1

  公开（公告）日：2012-11-28

  The present invention relates to a novel method for screening proteins related to and/or involved in plant cell cycle. It further relates to proteins isolated with the method, and the use of those proteins, and/or the genes encoding those proteins for modulating plant yield and plant growth.

  本发明涉及一种筛选与植物细胞周期有关和/或参与植物细胞周期的蛋白质的新方法。本发明还涉及用该方法分离的蛋白质，以及使用这些蛋白质和/或编码这些蛋白质的基因来调节植物产量和植物生长。
• DAS5, a P450 protein involved in the brassinosteroid biosynthesis pathway in plants
  申请人：——

  公开号：US20030150025A1

  公开（公告）日：2003-08-07

  The present invention provides a cytochrome P450-encoding gene, DAS5, as well as an altered gene, das5-D, which are involved in the synthesis of the plant steroid hormone brassinolide. The das5-D mutant has an insertion of a T-DNA containing transcriptional enhancers into its promoter region. Overexpression of the mutant thus produces large amounts of DAS5 transcript. The expression of this das5-D mutation or overexpression of the DAS5 gene in transgenic plants causes such plants to become significantly larger and more robust than their wild-type counterparts, thus increasing plant yields.

  本发明提供了一种细胞色素 P450 编码基因 DAS5 以及一种改变基因 das5-D，它们参与植物甾体激素黄铜内酯的合成。das5-D 突变体的启动子区域插入了一个含有转录增强子的 T-DNA 。因此，过量表达该突变体会产生大量的 DAS5 转录本。在转基因植物中表达这种 das5-D 突变体或过量表达 DAS5 基因，会使这些植物比野生型植物明显更大、更健壮，从而提高植物产量。