bisnoryangonin | 13709-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bisnoryangonin
• 英文别名: 4-Hydroxy-6[4-hydroxystyryl]2-pyrone；4-hydroxy-6-[2-(4-hydroxyphenyl)ethenyl]pyran-2-one
• CAS: 13709-27-8
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: ORVQWHLMVLOZPX-UHFFFAOYSA-N

物化性质

• 熔点：
  200-205 °C
• 沸点：
  440.3±45.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-coumaroyl coenzyme A 、 丙二酰辅酶A-钠盐 在 Oryza sativa curcuminoid synthase 作用下， 反应 3.0h， 以8.9%的产率得到(Z,E,E)-5-羟基-1,7-二(4-羟基苯基)-1,4,6-庚三烯-3-酮
  参考文献：
  名称：

  通过来自稻的类姜黄素合酶一锅形成二芳基庚烷支架的结构基础。

  摘要：

  来自水稻的类姜黄素合酶 (CUS) 是一种植物特异性 III 型聚酮化合物合酶 (PKS)，可催化双去甲氧基姜黄素的 C(6)-C(7)-C(6) 二芳基庚烷类支架的显着单锅形成，通过两分子 4-香豆酰辅酶 A 和一分子丙二酰辅酶 A 的缩合。O. sativa CUS 的晶体结构以 2.5-A 的分辨率解析，揭示了一种独特的向下扩展的活性位点结构，以前在已知的 III 型 PKS 中未发现。大的活性位点腔足够长以容纳两个 C(6)-C(3) 香豆酰单元和一个丙二酰单元。此外，晶体结构表明存在推定的亲核水分子，该分子与 Ser351-Asn142-H(2)O-Tyr207-Glu202 形成氢键网络，邻近活性中心的催化 Cys174。这些观察结果表明，CUS 采用独特的催化机制，用于 C(6)-C(7)-C(6) 支架的一锅形成。因此，CUS 利用亲核水在双酮阶段终止初始聚酮链延长。酶结合中间体的硫酯键断裂产生

  DOI：

  10.1073/pnas.1011499107

文献信息

• Cloning and Structure-Function Analyses of Quinolone- and Acridone-producing Novel Type III Polyketide Synthases from Citrus microcarpa
  作者：Takahiro Mori、Yoshihiko Shimokawa、Takashi Matsui、Keishi Kinjo、Ryohei Kato、Hiroshi Noguchi、Shigetoshi Sugio、Hiroyuki Morita、Ikuro Abe

  DOI：10.1074/jbc.m113.493155

  日期：2013.10

  Two novel type III polyketide synthases, quinolone synthase (QNS) and acridone synthase (ACS), were cloned from Citrus microcarpa (Rutaceae). The deduced amino acid sequence of C. microcarpa QNS is unique, and it shared only 56-60% identities with C. microcarpa ACS, Medicago sativa chalcone synthase (CHS), and the previously reported Aegle marmelos QNS. In contrast to the quinolone- and acridone-producing A. marmelos QNS, C. microcarpa QNS produces 4-hydroxy-N-methylquinolone as the single product by the one-step condensation of N-methylanthraniloyl-CoA and malonyl-CoA. However, C. microcarpa ACS shows broad substrate specificities and produces not only acridone and quinolone but also chalcone, benzophenone, and phloroglucinol from 4-coumaroyl-CoA, benzoyl-CoA, and hexanoyl-CoA, respectively. Furthermore, the x-ray crystal structures of C. microcarpa QNS and ACS, solved at 2.47- and 2.35- resolutions, respectively, revealed wide active site entrances in both enzymes. The wide active site entrances thus provide sufficient space to facilitate the binding of the bulky N-methylanthraniloyl-CoA within the catalytic centers. However, the active site cavity volume of C. microcarpa ACS (760 (3)) is almost as large as that of M. sativa CHS (750 (3)), and ACS produces acridone by employing an active site cavity and catalytic machinery similar to those of CHS. In contrast, the cavity of C. microcarpa QNS (290 (3)) is significantly smaller, which makes this enzyme produce the diketide quinolone. These results as well as mutagenesis analyses provided the first structural bases for the anthranilate-derived production of the quinolone and acridone alkaloid by type III polyketide synthases.
• Structural basis for the one-pot formation of the diarylheptanoid scaffold by curcuminoid synthase from <i>Oryza sativa</i>
  作者：Hiroyuki Morita、Kiyofumi Wanibuchi、Hirohiko Nii、Ryohei Kato、Shigetoshi Sugio、Ikuro Abe

  DOI：10.1073/pnas.1011499107

  日期：2010.11.16

  Curcuminoid synthase (CUS) from Oryza sativa is a plant-specific type III polyketide synthase (PKS) that catalyzes the remarkable one-pot formation of the C(6)-C(7)-C(6) diarylheptanoid scaffold of bisdemethoxycurcumin, by the condensation of two molecules of 4-coumaroyl-CoA and one molecule of malonyl-CoA. The crystal structure of O. sativa CUS was solved at 2.5-A resolution, which revealed a unique

  来自水稻的类姜黄素合酶 (CUS) 是一种植物特异性 III 型聚酮化合物合酶 (PKS)，可催化双去甲氧基姜黄素的 C(6)-C(7)-C(6) 二芳基庚烷类支架的显着单锅形成，通过两分子 4-香豆酰辅酶 A 和一分子丙二酰辅酶 A 的缩合。O. sativa CUS 的晶体结构以 2.5-A 的分辨率解析，揭示了一种独特的向下扩展的活性位点结构，以前在已知的 III 型 PKS 中未发现。大的活性位点腔足够长以容纳两个 C(6)-C(3) 香豆酰单元和一个丙二酰单元。此外，晶体结构表明存在推定的亲核水分子，该分子与 Ser351-Asn142-H(2)O-Tyr207-Glu202 形成氢键网络，邻近活性中心的催化 Cys174。这些观察结果表明，CUS 采用独特的催化机制，用于 C(6)-C(7)-C(6) 支架的一锅形成。因此，CUS 利用亲核水在双酮阶段终止初始聚酮链延长。酶结合中间体的硫酯键断裂产生