2-([1-O-(phenylmethanyl)-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranosyl]-(2->2)-[O-α-L-rhamnopyranosyl-(1->6)]-β-D-glucopyranosyl)cinnanic alcohol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-([1-O-(phenylmethanyl)-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranosyl]-(2->2)-[O-α-L-rhamnopyranosyl-(1->6)]-β-D-glucopyranosyl)cinnanic alcohol
• 英文别名: cinnacassinol；(2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-5-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-4,5-dihydroxy-2-phenylmethoxyoxan-3-yl]oxy-3,4-dihydroxy-6-[2-(3-hydroxyprop-1-enyl)phenoxy]oxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• 化学式: C₃₉H₅₄O₂₀
• 分子量: 842.846
• InChiKey: MQBGJIQDVYJCON-SALLFLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  306
• 氢给体数：
  11
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  2-([1-O-(phenylmethanyl)-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranosyl]-(2->2)-[O-α-L-rhamnopyranosyl-(1->6)]-β-D-glucopyranosyl)cinnanic alcohol 在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 D-apiose 、 L-鼠李糖 、 葡萄糖
  参考文献：
  名称：

  Tyrosinase-Inhibitory Constituents from the Twigs of Cinnamomum cassia

  摘要：

  A methanol extract of the twigs of Cinnamomum cassia was found to possess inhibitory activity against tyrosinase. Purification of the MeOH extract afforded four new phenolics, cassiferaidehyde (6), icariside DC (9), cinnacassinol (10), and dihydrocinnacasside (13), together with 10 known compounds (1-5, 7-12, and 14). The structures of the new compounds were determined by spectroscopic data interpretation. Compounds 1-6 and 8-13 showed strong inhibitory activity against tyrosinase, with IC50 values ranging from 0.24 to 0.94 mM.

  DOI：

  10.1021/np900031q