chrysin-6-C-glucopyranoside | 28368-57-2

• 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: chrysin-6-C-glucopyranoside
• 英文别名: 6-C-glucosylchrysin；6-(C-β-D-Glucopyranosyl)-chrysin；chrysin 6-C-glucoside；5,7-dihydroxy-2-phenyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• CAS: 28368-57-2
• 化学式: C₂₁H₂₀O₉
• 分子量: 416.384
• InChiKey: KLLCDVSOGLKTDV-VJXVFPJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  chrysin 6-C-(2''-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以3.33 mg的产率得到chrysin-6-C-glucopyranoside
  参考文献：
  名称：

  New flavone C-glycosides from leaves of Sarcotheca griffithii (Hook F) Hallier F

  摘要：

  DOI：

  10.1016/j.phytol.2014.04.005

文献信息

• 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.
• New flavone C-glycosides from leaves of Sarcotheca griffithii (Hook F) Hallier F
  作者：Rini Muharini、Victor Wray、Daowan Lai、Peter Proksch

  DOI：10.1016/j.phytol.2014.04.005

  日期：2014.9