neohesperidin dihydrochalcone

• 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: neohesperidin dihydrochalcone
• 英文别名: 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
• 化学式: C₂₈H₃₆O₁₅
• 分子量: 612.585
• InChiKey: RLZYBHOBTOBLGG-PJOVQGMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  橙皮甙 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 30.0 ℃ 、303.97 kPa 条件下， 反应 0.5h， 以80%的产率得到neohesperidin dihydrochalcone
  参考文献：
  名称：

  Dihydrochalcones:  Evaluation as Novel Radical Scavenging Antioxidants

  摘要：

  Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The H-1 NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2'-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.

  DOI：

  10.1021/jf0341060

文献信息

• Dihydrochalcones:  Evaluation as Novel Radical Scavenging Antioxidants
  作者：Yoshimasa Nakamura、Shigeo Watanabe、Nobuyuki Miyake、Hiroyuki Kohno、Toshihiko Osawa

  DOI：10.1021/jf0341060

  日期：2003.5.1

  Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The H-1 NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2'-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.