3',6'-di-O-acetyl-3-O-(E)-p-coumaroylsucrose

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3',6'-di-O-acetyl-3-O-(E)-p-coumaroylsucrose
• 英文别名: mumeose B；[(2S,3S,4R,5R)-2-[(2R,3R,4S,5R,6R)-4-acetyloxy-6-(acetyloxymethyl)-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₂₅H₃₂O₁₅
• 分子量: 572.52
• InChiKey: GRXCWAJNNHEMJK-OWIKANNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  228
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  3',6'-di-O-acetyl-3-O-(E)-p-coumaroylsucrose 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 蔗糖
  参考文献：
  名称：

  Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis

  摘要：

  The methanolic extract from the flower buds of Prunus mume, cultivated in Zhejiang Province, China, showed an inhibitory effect on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the methanolic extract, five acylated sucroses, mumeoses A-E, and three acylated quinic acid analogs, 5-O-(E)-p-coumaroylquinic acid ethyl ester, and mumeic acid-A and its methyl ester, were isolated together with 13 known compounds. The chemical structures of the compounds were elucidated on the basis of chemical and physicochemical evidence. Inhibitory effects of the isolated compounds on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were also investigated. Acylated quinic acid analogs substantially inhibited melanogenesis. In particular, 5-O-(E)-feruloylquinic acid methyl ester exhibited a potent inhibitory effect [inhibition (%): 21.5 +/- 1.0 (P < 0.01) at 0.1 mu M]. Moreover, its biological effect was much stronger than that of the reference compound, arbutin [inhibition (%): 10.6 +/- 0.6 (P < 0.01) at 10 mu M]. Interestingly, the obtained acylated quinic acid analogs displaying melanogenesis inhibitory activity showed no cytotoxicity [cell viability >97% at 10 mu M]. It is concluded that acylated quinic acid analogs are promising therapeutic agents for the treatment of skin disorders. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.04.012

文献信息

• Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis
  作者：Seikou Nakamura、Katsuyoshi Fujimoto、Takahiro Matsumoto、Souichi Nakashima、Tomoe Ohta、Keiko Ogawa、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1016/j.phytochem.2013.04.012

  日期：2013.8

  The methanolic extract from the flower buds of Prunus mume, cultivated in Zhejiang Province, China, showed an inhibitory effect on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the methanolic extract, five acylated sucroses, mumeoses A-E, and three acylated quinic acid analogs, 5-O-(E)-p-coumaroylquinic acid ethyl ester, and mumeic acid-A and its methyl ester, were isolated together with 13 known compounds. The chemical structures of the compounds were elucidated on the basis of chemical and physicochemical evidence. Inhibitory effects of the isolated compounds on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were also investigated. Acylated quinic acid analogs substantially inhibited melanogenesis. In particular, 5-O-(E)-feruloylquinic acid methyl ester exhibited a potent inhibitory effect [inhibition (%): 21.5 +/- 1.0 (P < 0.01) at 0.1 mu M]. Moreover, its biological effect was much stronger than that of the reference compound, arbutin [inhibition (%): 10.6 +/- 0.6 (P < 0.01) at 10 mu M]. Interestingly, the obtained acylated quinic acid analogs displaying melanogenesis inhibitory activity showed no cytotoxicity [cell viability >97% at 10 mu M]. It is concluded that acylated quinic acid analogs are promising therapeutic agents for the treatment of skin disorders. (c) 2013 Elsevier Ltd. All rights reserved.