2-(3,5-dihydroxyphenyl)-2,5,7-trihydroxy-3H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3,5-dihydroxyphenyl)-2,5,7-trihydroxy-3H-chromen-4-one
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: IFJSEOYXMXPYTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(3,5-dihydroxyphenyl)-2,5,7-trihydroxy-3H-chromen-4-one 、 UDP-glucose 在 recombinant Oryza sativa C-glycosyltransferase 作用下， 以 乙醇 为溶剂， 以47%的产率得到
  参考文献：
  名称：

  Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins

  摘要：

  The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus. (C) 2016 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2016.02.013
• 作为产物：
  描述：

  2-乙酰基-3,5-双(苄氧基)苯酚 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(3,5-dihydroxyphenyl)-2,5,7-trihydroxy-3H-chromen-4-one
  参考文献：
  名称：

  Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins

  摘要：

  The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus. (C) 2016 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.phytochem.2016.02.013

文献信息

• [EN] DIHYDROMYRICETIN FOR THE TREATMENT OF DISEASES AND DISORDERS OF THE GLUTAMATERGIC SYSTEM<br/>[FR] DIHYDROMYRICÉTINE POUR LE TRAITEMENT DE MALADIES ET DE TROUBLES DU SYSTÈME GLUTAMATERGIQUE
  申请人：UNIV CALIFORNIA

  公开号：WO2014007853A1

  公开（公告）日：2014-01-09

  Disclosed herein are methods and compositions for treating a disease or disorder of the glutamatergic system, e.g., Alzheimer's disease, neuron damage and/or loss, and seizures, or a symptom thereof, e.g., decreased cognitive function, in a subject which comprises administering dihydromyricetin (DHM), an analog of DHM, or a metabolite of DHM to the subject.
• Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins
  作者：B. Hao、J.C. Caulfield、M.L. Hamilton、J.A. Pickett、C.A.O. Midega、Z.R. Khan、J. Wang、A.M. Hooper

  DOI：10.1016/j.phytochem.2016.02.013

  日期：2016.5

  The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus. (C) 2016 The Authors. Published by Elsevier Ltd.