2-hydroxypinocembrin | 40489-17-6

• 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-hydroxypinocembrin
• 英文别名: 2,5,7-Trihydroxyflavanon；2,5,7-Trihydroxyflavanone；2,5,7-trihydroxy-2-phenyl-3H-chromen-4-one
• CAS: 40489-17-6
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: KRSTWHCNVMDXQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  UDP-glucose 、 2-hydroxypinocembrin 在 recombinant Oryza sativa C-glycosyltransferase 作用下， 以 乙醇 为溶剂， 以47%的产率得到chrysin-6-C-glucopyranoside
  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-benzoyloxy-4,6-dibenzyloxyacetophenone 在 palladium 10% on activated carbon 、 氢气 、 potassium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 1.0h， 生成 2-hydroxypinocembrin
  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

• 7-carboxy-flavone derivatives preparation method and therapeutic use
  申请人：——

  公开号：US20040059136A1

  公开（公告）日：2004-03-25

  The invention concerns novel flavone and isoflavone derivatives of formulae (Ia) and (Ib) wherein: X represents a group of formula —COOR, or —PO(OR) 2 ; R represents a hydrogen atom or an alkaline or alkaline-earth metal, or a lower alkyl group; R 1 represents a hydroxy group, a lower alkoxy group or an acyloxy group; R 2 and R 3 , identical or different, represent a hydrogen or halogen atom, or a trifluoromethyl group, a trichloromethyl group, a hydroxy group, an alkoxy group or an acyloxy group comprising 1 to 5 carbon atoms, or R 2 and R 3 can combine to form an alkylene dioxy group. The invention is useful for rheumatic diseases. 1

  该发明涉及具有以下式(Ia)和(Ib)的新型黄酮和异黄酮衍生物：其中：X代表式—COOR或—PO(OR)2的基团；R代表氢原子或碱金属或碱土金属，或低碳基；R1代表羟基、低碳氧基或酰氧基；R2和R3，相同或不同，代表氢原子或卤素原子，或三氟甲基基团、三氯甲基基团、羟基、烷氧基或含有1至5个碳原子的酰氧基，或R2和R3可以结合形成烷二氧基基团。该发明对风湿病有用。
• DERIVES DE 7-CARBOXY-FLAVONES, PROCEDE DE PREPARATION ET APPLICATION EN THERAPEUTIQUE
  申请人：Negma-Lerads

  公开号：EP1212313B1

  公开（公告）日：2003-05-28
• US6965039B2
  申请人：——

  公开号：US6965039B2

  公开（公告）日：2005-11-15
• [EN] 7-CARBOXY-FLAVONE DERIVATIVES, PREPARATION METHOD AND THERAPEUTIC USE<br/>[FR] DÉRIVÉS DE 7-CARBOXY-FLAVONES, PROCÉDÉ DE PRÉPARATION ET APPLICATION EN THÉRAPEUTIQUE
  申请人：NEGMA LERADS

  公开号：WO2002028851A1

  公开（公告）日：2002-04-11

  L'invention concerne de nouveaux dérivés de flavones et d isoflavones (voir formules)dans lesquelles X représente un groupe de formule -COOR, ou -PO(OR)2, R représente un atome d'hydrogène ou de métal alcalin ou alcalino-terreux, ou un groupe alkyle inférieur, R1 représente un groupe hydroxy, un groupe alkoxy inférieur ou un groupe acyloxy, R2 et R3, identiques ou différents, représentent un atome d'hydrogène ou d'halogène, ou un groupe trifluoro-méthyle, un groupe trichlorométhyle,un groupe hydroxy, un groupe alkoxy ou un groupe acyloxy comportant 1 à 5 atomes de carbone, ou R2 et R3 peuvent s'associer pour former un groupe alkylène dioxy. Application au traitement des maladies rhumatismales.
• 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.