2,5,6-trihydroxy-9-phenylphenalen-1-one | 1393689-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,5,6-trihydroxy-9-phenylphenalen-1-one
• 英文别名: 2,5,6-trihydroxy-7-phenylphenalen-1-one；lachnanthoside aglycone；2,5,6-Trihydroxy-7-phenylphenalen-1-one
• CAS: 1393689-38-7
• 化学式: C₁₉H₁₂O₄
• 分子量: 304.302
• InChiKey: YBLMKRYXGPABSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5,6-trihydroxy-9-phenylphenalen-1-one 、 [¹³C]dioazomethane 以 乙醚 为溶剂， 生成 [2,5,6-tri-O¹³CH₃]2,5,6-trimethoxy-7-phenylphenalen-1-one
  参考文献：
  名称：

  Biosynthesis of tetraoxygenated phenylphenalenones in Wachendorfia thyrsiflora

  摘要：

  The biosynthetic origin of 1,2,5,6-tetraoxygenated phenylphenalenones and the sequence according to which their oxygen functionalities are introduced during the biosynthesis in Wachendorfia thyrsiflora were studied using two approaches. (1) Oxygenated phenylpropanoids were probed as substrates of recombinant W thyrsiflora polyketide synthase I (WtPKS1), which is involved in the diarylheptanoid and phenylphenalenone biosynthetic pathways, (2) Root cultures of W thyrsiflora were incubated with C-13-labelled precursors in an O-18(2) atmosphere to observe incorporation of the two isotopes at defined biosynthetic steps. NMR- and HRESIMS-based analyses were used to unravel the isotopologue composition of the biosynthetic products, lachnanthoside aglycone and its allophanyl glucoside. Current results suggest that the oxygen atoms decorating the phenalenone tricycle are introduced at different biosynthetic stages in the sequence O-1 -> O-2 -> O-5. In addition, the incubation of W. thyrsiflora root cultures with C-13-labelled lachnanthocarpone established a direct biosynthetic precursor-product relationship with I,2,5,6-tetraoxygenated phenylphenalenones. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.02.020

文献信息

• Biosynthesis of tetraoxygenated phenylphenalenones in Wachendorfia thyrsiflora
  作者：Tobias Munde、Silke Brand、William Hidalgo、Ravi K. Maddula、Aleš Svatoš、Bernd Schneider

  DOI：10.1016/j.phytochem.2012.02.020

  日期：2013.7

  The biosynthetic origin of 1,2,5,6-tetraoxygenated phenylphenalenones and the sequence according to which their oxygen functionalities are introduced during the biosynthesis in Wachendorfia thyrsiflora were studied using two approaches. (1) Oxygenated phenylpropanoids were probed as substrates of recombinant W thyrsiflora polyketide synthase I (WtPKS1), which is involved in the diarylheptanoid and phenylphenalenone biosynthetic pathways, (2) Root cultures of W thyrsiflora were incubated with C-13-labelled precursors in an O-18(2) atmosphere to observe incorporation of the two isotopes at defined biosynthetic steps. NMR- and HRESIMS-based analyses were used to unravel the isotopologue composition of the biosynthetic products, lachnanthoside aglycone and its allophanyl glucoside. Current results suggest that the oxygen atoms decorating the phenalenone tricycle are introduced at different biosynthetic stages in the sequence O-1 -> O-2 -> O-5. In addition, the incubation of W. thyrsiflora root cultures with C-13-labelled lachnanthocarpone established a direct biosynthetic precursor-product relationship with I,2,5,6-tetraoxygenated phenylphenalenones. (C) 2012 Elsevier Ltd. All rights reserved.