11-O-β-D-glucopyranosyloxy-5-methoxy-6-oxabenzochrysen-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 11-O-β-D-glucopyranosyloxy-5-methoxy-6-oxabenzochrysen-1-one
• 英文别名: haemodoroxychrysenose
• 化学式: C₂₆H₂₂O₉
• 分子量: 478.455
• InChiKey: MQPYGQGPGUGVOU-UUGZZFCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  138.82
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  11-O-β-D-glucopyranosyloxy-5-methoxy-6-oxabenzochrysen-1-one 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 可得然胶 、 beta-D-吡喃木糖 、 β-半乳糖苷酶 、 6-deoxy-β-D-mannopyranose
  参考文献：
  名称：

  Phenylphenalenones and oxabenzochrysenones from the Australian plant Haemodorum simulans

  摘要：

  Chemical investigation of the Australian plant Haemodorum simulans (Haemodoraceae) resulted in the isolation of two new phenylphenalenones, haemoxiphidone and haemodordioxolane from the bulbs together with the first report of an oxabenzochrysenone glycoside, haemodoroxychrysenose from the aerial parts of the plant. Also isolated were two previously described phenylphenalenones 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione and haemodorone and two oxabenzochrysenones 5-hydroxyl-2-methoxy-1H-naphtho[2,1,8-mna]xanthen-1-one and 5-methoxy-1H-naphtho[2,1,8-mna]xanthen-1-one. The X-ray structure of the phenylphenalenone 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione was secured for the first time. All compounds were deduced by detailed spectroscopic analyses. HPLC-NMR chemical profiling of an enriched fraction containing a mixture of haemodordioxolane and 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione facilitated the partial identification of these secondary metabolites. The structure previously assigned as xiphidone in our initial studies of this plant was re-assigned as the new isomer haemoxiphidone. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.07.019

文献信息

• Phenylphenalenones and oxabenzochrysenones from the Australian plant Haemodorum simulans
  作者：Sylvia Urban、Michael A. Timmers、Robert Brkljača、Jonathan M. White

  DOI：10.1016/j.phytochem.2013.07.019

  日期：2013.11

  Chemical investigation of the Australian plant Haemodorum simulans (Haemodoraceae) resulted in the isolation of two new phenylphenalenones, haemoxiphidone and haemodordioxolane from the bulbs together with the first report of an oxabenzochrysenone glycoside, haemodoroxychrysenose from the aerial parts of the plant. Also isolated were two previously described phenylphenalenones 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione and haemodorone and two oxabenzochrysenones 5-hydroxyl-2-methoxy-1H-naphtho[2,1,8-mna]xanthen-1-one and 5-methoxy-1H-naphtho[2,1,8-mna]xanthen-1-one. The X-ray structure of the phenylphenalenone 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione was secured for the first time. All compounds were deduced by detailed spectroscopic analyses. HPLC-NMR chemical profiling of an enriched fraction containing a mixture of haemodordioxolane and 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione facilitated the partial identification of these secondary metabolites. The structure previously assigned as xiphidone in our initial studies of this plant was re-assigned as the new isomer haemoxiphidone. (C) 2013 Elsevier Ltd. All rights reserved.