异金雀儿黄素 | 4328-19-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 异金雀儿黄素
• 中文别名: 氨甲酸,[(3S,4S)-四氢-5-羟基-4-甲基-3-呋喃基]-,1,1-二甲基乙基酯(9CI)
• 英文名称: isovitexin 4'-methyl ether
• 英文别名: isocytisoside；5,7-dihydroxy-2-(4-methoxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• CAS: 4328-19-2
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: AQHMJUSCGYYXRM-DGHBBABESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  异金雀儿黄素 、 三苯基氯甲烷 在 吡啶 作用下， 反应 288.0h， 生成 6''-O-trityl-6-C-β-D-glucopyranosylacacetin
  参考文献：
  名称：

  全甲基 6-C-糖基黄酮在电子轰击质谱中的裂解模式

  摘要：

  摘要 根据在 2"-、3"-、4"- 或 6"-位置单-O-氘代甲基化的全甲基衍生物的 MS 数据，提出了全甲基 6-C-糖基黄酮的质谱裂解模式。描述了通过 O''-糖基-6-C-葡萄糖基黄酮合成这些化合物。

  DOI：

  10.1016/s0031-9422(00)83808-x
• 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 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 异金雀儿黄素 、 4-甲氧基牡荆素
  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

• New C,O-Glycosylflavones from the Genus Silene
  作者：D. N. Olennikov、N. I. Kashchenko

  DOI：10.1007/s10600-020-03220-x

  日期：2020.11

  Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (sileneside D, 1) from S. jeniseensis Willd., apigenin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-8-C-α-L-arabinopyranoside (sileneside E, 2) and genkwanin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-8-C-α-L-arabinopyranoside (sileneside F, 3) from S. italica (L.) Pers., and apigenin-6-C-(2″-O-β-D-xylopyranosyl)-β-D-glucopyranoside-7-O-(6″″-O-feruloyl)-β-D-glucopyranoside (sileneside G, 4) from S. dioica (L.) Clairv. The structures of 1–4 were studied using UV, IR, and NMR spectroscopy and mass spectrometry.

  对三种 Silene 物种（石竹科）地上部分的提取物进行色谱分离，分离出 26 种黄酮类化合物，包括四种新的 C,O-糖基黄酮 acacetin-6-C-(2″-O-β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖苷-7-O-β-D-吡喃葡萄糖苷（硅烯苷 D，1），来自 S. jeniseensis Willd.，芹菜素-6-C-(2″-O-β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖苷-8 -C-α-L-吡喃葡萄糖苷（硅烯苷 E，2）和 genkwanin-6-C-(2″-O-β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖苷-8-C-α-L-吡喃葡萄糖苷（来自 S. italica (L.) Pers. 的硅烯苷 F, 3) 和芹菜素-6-C-(2″-O-β-D-吡喃木糖基)-β-D-吡喃葡萄糖苷-7-O-(6″″ -O-阿魏酰)-β-D-吡喃葡萄糖苷 (sileneside G, 4)，来自 S. dioica (L.) Clairv。使用紫外、红外、核磁共振光谱和质谱研究了 1-4 的结构。
• 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.
• Fragmentation pattern of permethyl 6-C-glycosylflavones in electron impact mass spectrometry
  作者：M.L. Bouillant、A. Besset、J. Favre-Bonvin、J. Chopin

  DOI：10.1016/s0031-9422(00)83808-x

  日期：——

  Abstract A mass spectral fragmentation pattern of permethyl 6- C -glycosylflavones is proposed from the MS data of permethyl derivatives mono- O -deuteriomethylated in the 2″-, 3″-, 4″- or 6″-positions. The synthesis of these compounds via O″ -glycosyl-6- C -glucosylflavones is described.

  摘要 根据在 2"-、3"-、4"- 或 6"-位置单-O-氘代甲基化的全甲基衍生物的 MS 数据，提出了全甲基 6-C-糖基黄酮的质谱裂解模式。描述了通过 O''-糖基-6-C-葡萄糖基黄酮合成这些化合物。