(2R,3R)-2-(3,5-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one | 206753-49-3

• 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: (2R,3R)-2-(3,5-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one
• 英文别名: 3,5,7,3’,5’-pentahydroxyflavanone；3,5,7,3',5'-pentahydroxydihydroflavonol；3,3',5,5',7-pentahydroxyflavanone；3,3',5,5',7-pentahydroxyflavonone；(2r,3r)-3,5,7,3',5'-Pentahydroxyflavanone；(2R,3R)-2-(3,5-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• CAS: 206753-49-3
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: SRHDEHLQIMAWNV-LSDHHAIUSA-N

物化性质

• 沸点：
  691.4±55.0 °C(Predicted)
• 密度：
  1.702±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 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：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 盐酸 、 双氧水 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 正己烷 、 水 、 丙酮 为溶剂， 反应 7.17h， 生成 (2R,3R)-2-(3,5-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one 、 3,5,7-trihydroxy-2–(3,5-dihydroxyphenyl)chroman-4-one
  参考文献：
  名称：

  Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship

  摘要：

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.042

文献信息

• Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship
  作者：Wen-Jun Jiang、Kan’ichiro Ishiuchi、Megumi Furukawa、Tomoko Takamiya、Susumu Kitanaka、Hiroshi Iijima

  DOI：10.1016/j.bmc.2015.09.042

  日期：2015.11

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.