6a-羟基高丽槐素 | 61218-44-8

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 6a-羟基高丽槐素
• 中文别名: 6A-羟基高丽槐素
• 英文名称: 6a-hydroxymaackiain
• 英文别名: (1S,12S)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol
• CAS: 61218-44-8
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: GLMPLZUBQDAZEN-JKSUJKDBSA-N

物化性质

• 沸点：
  518.7±50.0 °C(Predicted)
• 密度：
  1.634±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  高丽槐素 在 Colletotrichum gloeosporioides 作用下， 以 乙醇 为溶剂， 生成 6a-羟基高丽槐素 、
  参考文献：
  名称：

  Oxidation of the phytoalexin maackiain to 6,6a-dihydroxy-maackiain by Colletotrichum gloeosporioides

  摘要：

  Phytoalexins are low molecular weight antibiotic compounds produced by plants in response to infection by microbes. These antimicrobial compounds are thought to provide resistance to microbial invasion and colonization. (-)Maackiain and its pterocarpan relatives can be oxidized at a number of sites, including at the 6a carbon. A previously unknown metabolite was produced from (-)maackiain by the broad host-range pathogen Colletotrichum gloeosporioides (Glomerella cingulata). This unknown was identified by LCMS-MS and NMR spectroscopy to be 6,6a-di-OH-maackiain (3,6,6a-trihydroxy-8,9-methylenedioxy-pterocarpan). It is produced by isolates that represent all four races and pathotypes of C. gloeosporioides isolated from the tropical forage legume Stylosanthes spp. We present evidence that the primary metabolite (-)6a-OH-maackiain is subsequently hydroxylated at carbon 6, a step resulting in a compound that is increased in polarity and decreased in toxicity relative to the parent compound and (-)6a-OH-maackiain. This further oxidation may be required for efficient excretion or carbon source scavenging. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(97)00082-4

文献信息

• Oxidation of the phytoalexin maackiain to 6,6a-dihydroxy-maackiain by Colletotrichum gloeosporioides
  作者：Scott Soby、Robert Bates、Hans Van Etten

  DOI：10.1016/s0031-9422(97)00082-4

  日期：1997.7

  Phytoalexins are low molecular weight antibiotic compounds produced by plants in response to infection by microbes. These antimicrobial compounds are thought to provide resistance to microbial invasion and colonization. (-)Maackiain and its pterocarpan relatives can be oxidized at a number of sites, including at the 6a carbon. A previously unknown metabolite was produced from (-)maackiain by the broad host-range pathogen Colletotrichum gloeosporioides (Glomerella cingulata). This unknown was identified by LCMS-MS and NMR spectroscopy to be 6,6a-di-OH-maackiain (3,6,6a-trihydroxy-8,9-methylenedioxy-pterocarpan). It is produced by isolates that represent all four races and pathotypes of C. gloeosporioides isolated from the tropical forage legume Stylosanthes spp. We present evidence that the primary metabolite (-)6a-OH-maackiain is subsequently hydroxylated at carbon 6, a step resulting in a compound that is increased in polarity and decreased in toxicity relative to the parent compound and (-)6a-OH-maackiain. This further oxidation may be required for efficient excretion or carbon source scavenging. (C) 1997 Elsevier Science Ltd. All rights reserved.