mumeose C | 1446205-86-2

• 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: mumeose C
• 英文别名: [(2S,3S,4R,5R)-2-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-hydroxyoxan-2-yl]oxy-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 1446205-86-2
• 化学式: C₂₇H₃₄O₁₆
• 分子量: 614.557
• InChiKey: RVECJMKUWCVVGH-PZHMIARSSA-N

物化性质

• 沸点：
  799.6±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  234
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  mumeose C 在 硫酸 、 L-半胱氨酸甲酯盐酸盐 、 邻甲苯异硫氰酸酯 作用下， 以 1,4-二氧六环 、 水 、 吡啶 为溶剂， 反应 5.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  Structures of acylated sucroses and an acylated flavonol glycoside and inhibitory effects of constituents on aldose reductase from the flower buds of Prunus mume

  摘要：

  从中国浙江省栽培的梅花蕾中分离出五种新的酰化蔗糖（mumeoses K-O）和一种新的酰化黄酮醇糖苷（mumeflavonoside A）。根据化学和物理化学证据阐明了新化合物的化学结构。还研究了分离的酰化蔗糖和黄酮醇苷对醛糖还原酶的抑制作用。包括 mumeflavonoside A 在内的几种黄酮醇糖苷已被证明可以抑制醛糖还原酶。

  DOI：

  10.1007/s11418-013-0750-7

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.
• Structures of acylated sucroses and an acylated flavonol glycoside and inhibitory effects of constituents on aldose reductase from the flower buds of Prunus mume
  作者：Seikou Nakamura、Katsuyoshi Fujimoto、Takahiro Matsumoto、Tomoe Ohta、Keiko Ogawa、Haruka Tamura、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1007/s11418-013-0750-7

  日期：2013.10

  Five new acylated sucroses, mumeoses K–O, and a new acylated flavonol glycoside, mumeflavonoside A, were isolated from the flower buds of Prunus mume, cultivated in Zhejiang province, China. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated acylated sucroses and flavonol glycosides on aldose reductase were also investigated. Several flavonol glycosides including mumeflavonoside A were shown to inhibit aldose reductase.

  从中国浙江省栽培的梅花蕾中分离出五种新的酰化蔗糖（mumeoses K-O）和一种新的酰化黄酮醇糖苷（mumeflavonoside A）。根据化学和物理化学证据阐明了新化合物的化学结构。还研究了分离的酰化蔗糖和黄酮醇苷对醛糖还原酶的抑制作用。包括 mumeflavonoside A 在内的几种黄酮醇糖苷已被证明可以抑制醛糖还原酶。