5,4'-dihydroxy-3'-methoxyflavone-7-O-β-galacturonide | 29741-07-9

• 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: 5,4'-dihydroxy-3'-methoxyflavone-7-O-β-galacturonide
• 英文别名: isorhamnetin 7-O-β-D-glucopyranuronide；crysoeriol 7-O-β-D-glucopyranuronide；chrysoeriol-7-O-β-D-glucuronide；chrysoriol 7-O-β-D-glucuronide；chrysoeriol-7-O-β-glucuronide；chrysoeriol 7-O-glucuronide；Chrysoeriol glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid
• CAS: 29741-07-9
• 化学式: C₂₂H₂₀O₁₂
• 分子量: 476.394
• InChiKey: VLYLVFHVHHGXHX-SXFAUFNYSA-N

物化性质

• 熔点：
  272-274 °C
• 沸点：
  851.5±65.0 °C(Predicted)
• 密度：
  1.695±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  金圣草(黄)素 、 6-[[[5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-3,4,5-三羟基四氢吡喃-2-羧酸 在 Veronica persica UDP-dependent glycosyl transferase 88D₈ 作用下， 以 potassium phosphate buffer 为溶剂， 生成 5,4'-dihydroxy-3'-methoxyflavone-7-O-β-galacturonide
  参考文献：
  名称：

  Co-pigmentation and flavonoid glycosyltransferases in blue Veronica persica flowers

  摘要：

  Glycosylation is one of the key modification steps for plants to produce a broad spectrum of flavonoids with various structures and colors. A survey of flavonoids in the blue flowers of Veronica persica Poiret (Lamiales, Scrophulariaceae), which is native of Eurasia and now widespread worldwide, led to the identification of highly glycosylated flavonoids, namely delphinidin 3-O-(2-O-(6-O-p-coumaroyl-glucosyl)-6-O-p-coumaroyl-glucoside)-5-O-glucoside (1) and apigenin 7-O-(2-O-glucuronosyl)-glucuronide (2), as two of its main flavonoids. Interestingly, the latter flavone glucuronide (2) caused a bathochromic shift on the anthocyanin (1) toward a blue hue in a dose-dependent manner, showing an intermolecular co-pigment effect. In order to understand the molecular basis for the biosynthesis of this glucuronide, we isolated a cDNA encoding a UDP-dependent glycosyltransferase (UGT88D8), based on the structural similarity to flavonoid 7-O-glucuronosyltransferases (F7GAT) from Lamiales plants. Enzyme assays showed that the recombinant UGT88D8 protein catalyzes the 7-O-glucuronosylation of apigenin and its related flavonoids with preference to UDP-glucuronic acid as a sugar donor. Furthermore, we identified and functionally characterized a cDNA encoding another UGT, UGT94F1, as the anthocyanin 3-O-glucoside2 ''-O-glucosyltransferase (A3Glc2 '' GlcT), according to the structural similarity to sugar-sugar glycosyl-transferases classified to the cluster IV of flavonoid UGTs. Preferential expression of UGT88D8 and UGT94F1 genes in the petals supports the idea that these UGTs play an important role in the biosynthesis of key flavonoids responsible for the development of the blue color of V. persica flowers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.02.008

文献信息

• Co-pigmentation and flavonoid glycosyltransferases in blue Veronica persica flowers
  作者：Eiichiro Ono、Miho Ruike、Takashi Iwashita、Kyosuke Nomoto、Yuko Fukui

  DOI：10.1016/j.phytochem.2010.02.008

  日期：2010.5

  Glycosylation is one of the key modification steps for plants to produce a broad spectrum of flavonoids with various structures and colors. A survey of flavonoids in the blue flowers of Veronica persica Poiret (Lamiales, Scrophulariaceae), which is native of Eurasia and now widespread worldwide, led to the identification of highly glycosylated flavonoids, namely delphinidin 3-O-(2-O-(6-O-p-coumaroyl-glucosyl)-6-O-p-coumaroyl-glucoside)-5-O-glucoside (1) and apigenin 7-O-(2-O-glucuronosyl)-glucuronide (2), as two of its main flavonoids. Interestingly, the latter flavone glucuronide (2) caused a bathochromic shift on the anthocyanin (1) toward a blue hue in a dose-dependent manner, showing an intermolecular co-pigment effect. In order to understand the molecular basis for the biosynthesis of this glucuronide, we isolated a cDNA encoding a UDP-dependent glycosyltransferase (UGT88D8), based on the structural similarity to flavonoid 7-O-glucuronosyltransferases (F7GAT) from Lamiales plants. Enzyme assays showed that the recombinant UGT88D8 protein catalyzes the 7-O-glucuronosylation of apigenin and its related flavonoids with preference to UDP-glucuronic acid as a sugar donor. Furthermore, we identified and functionally characterized a cDNA encoding another UGT, UGT94F1, as the anthocyanin 3-O-glucoside2 ''-O-glucosyltransferase (A3Glc2 '' GlcT), according to the structural similarity to sugar-sugar glycosyl-transferases classified to the cluster IV of flavonoid UGTs. Preferential expression of UGT88D8 and UGT94F1 genes in the petals supports the idea that these UGTs play an important role in the biosynthesis of key flavonoids responsible for the development of the blue color of V. persica flowers. (C) 2010 Elsevier Ltd. All rights reserved.