3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin | 1420045-11-9

• 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: 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin
• 英文别名: [2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] 3,4,5-tris(methoxymethoxy)benzoate；[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] 3,4,5-tris(methoxymethoxy)benzoate
• CAS: 1420045-11-9
• 化学式: C₂₈H₂₆O₁₄
• 分子量: 586.506
• InChiKey: QRGRAUNVZFYLOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以83%的产率得到2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  A Novel Semisynthetic Flavonoid 7-O-Galloyltaxifolin Upregulates Heme Oxygenase-1 in RAW264.7 Cells via MAPK/Nrf2 Pathway

  摘要：

  Quercetin and gallic acid are natural activators of the transcription factor Nrf2, which regulates the expression of many cytoprotective enzymes including heme oxygenase-1 (HO-1). We developed procedures for the synthesis of monogalloyl esters of quercetin and taxifolin (dihydroquercetin), namely, 3-O-galloylquercetin and 7-O-galloyltaxifolin, and examined their effect on the Nrf2 pathway in RAW264.7 cells. Unlike quercetin and free gallic acid, 3-O-galloylquercetin and natural quercetin derivatives isoquercitrin (quercetin-3-O-beta-D-glucoside) and taxifolin had no effect on the expression of HO-1. In contrast, 7-O-galloyltaxifolin increased both mRNA and protein levels of HO-1 at concentrations of 25 mu M and above. The induction of HO-1 by 7-O-galloyltaxifolin was primarily associated with the production of reactive oxygen species and phosphorylation of mitogen-activated protein kinases (MAPKs), including p38 MAPKs and ERKs, followed by nuclear accumulation of Nrf2 and downregulation of Keap1, a negative regulator of Nrf2. We conclude that 7-O-galloyltaxifolin upregulates HO-1 via activation of the MAPK/Nrf2 signaling pathway.

  DOI：

  10.1021/jm3013344
• 作为产物：
  描述：

  芦丁 在 盐酸 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 caesium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.17h， 生成 3-O-[(3″,4″,5″-tri-O-methoxymethyl)-galloyl]quercetin
  参考文献：
  名称：

  A Novel Semisynthetic Flavonoid 7-O-Galloyltaxifolin Upregulates Heme Oxygenase-1 in RAW264.7 Cells via MAPK/Nrf2 Pathway

  摘要：

  Quercetin and gallic acid are natural activators of the transcription factor Nrf2, which regulates the expression of many cytoprotective enzymes including heme oxygenase-1 (HO-1). We developed procedures for the synthesis of monogalloyl esters of quercetin and taxifolin (dihydroquercetin), namely, 3-O-galloylquercetin and 7-O-galloyltaxifolin, and examined their effect on the Nrf2 pathway in RAW264.7 cells. Unlike quercetin and free gallic acid, 3-O-galloylquercetin and natural quercetin derivatives isoquercitrin (quercetin-3-O-beta-D-glucoside) and taxifolin had no effect on the expression of HO-1. In contrast, 7-O-galloyltaxifolin increased both mRNA and protein levels of HO-1 at concentrations of 25 mu M and above. The induction of HO-1 by 7-O-galloyltaxifolin was primarily associated with the production of reactive oxygen species and phosphorylation of mitogen-activated protein kinases (MAPKs), including p38 MAPKs and ERKs, followed by nuclear accumulation of Nrf2 and downregulation of Keap1, a negative regulator of Nrf2. We conclude that 7-O-galloyltaxifolin upregulates HO-1 via activation of the MAPK/Nrf2 signaling pathway.

  DOI：

  10.1021/jm3013344

文献信息

• A Novel Semisynthetic Flavonoid 7-<i>O</i>-Galloyltaxifolin Upregulates Heme Oxygenase-1 in RAW264.7 Cells via MAPK/Nrf2 Pathway
  作者：Jiří Vrba、Radek Gažák、Marek Kuzma、Barbora Papoušková、Jan Vacek、Martin Weiszenstein、Vladimír Křen、Jitka Ulrichová

  DOI：10.1021/jm3013344

  日期：2013.2.14

  Quercetin and gallic acid are natural activators of the transcription factor Nrf2, which regulates the expression of many cytoprotective enzymes including heme oxygenase-1 (HO-1). We developed procedures for the synthesis of monogalloyl esters of quercetin and taxifolin (dihydroquercetin), namely, 3-O-galloylquercetin and 7-O-galloyltaxifolin, and examined their effect on the Nrf2 pathway in RAW264.7 cells. Unlike quercetin and free gallic acid, 3-O-galloylquercetin and natural quercetin derivatives isoquercitrin (quercetin-3-O-beta-D-glucoside) and taxifolin had no effect on the expression of HO-1. In contrast, 7-O-galloyltaxifolin increased both mRNA and protein levels of HO-1 at concentrations of 25 mu M and above. The induction of HO-1 by 7-O-galloyltaxifolin was primarily associated with the production of reactive oxygen species and phosphorylation of mitogen-activated protein kinases (MAPKs), including p38 MAPKs and ERKs, followed by nuclear accumulation of Nrf2 and downregulation of Keap1, a negative regulator of Nrf2. We conclude that 7-O-galloyltaxifolin upregulates HO-1 via activation of the MAPK/Nrf2 signaling pathway.