(S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-α-L-arabinofuranosyl-(1->6)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-α-L-arabinofuranosyl-(1->6)-β-D-glucopyranoside
• 英文别名: papyriferoside A；(5S)-5-[(2R,3R,4S,5S,6R)-6-[[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-1,7-bis(4-hydroxyphenyl)heptan-3-one
• 化学式: C₃₀H₄₀O₁₃
• 分子量: 608.64
• InChiKey: UGYZLORFQGTFRN-JQHXOKSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-α-L-arabinofuranosyl-(1->6)-β-D-glucopyranoside 在 盐酸 作用下， 反应 4.0h， 生成 (5S)-1,7-bis(4-hydroxyphenyl)-5-hydroxyheptan-3-one
  参考文献：
  名称：

  Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera

  摘要：

  Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides (1-4), a diarylheptanoid (5), a lignan (6), flavonoids (7-8) and chavicol glycosides (9-10). Among them, the diarylheptanoid glycoside, (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-alpha-L-arabinofuranosyl-(1 -> 6)-beta-D-gluco-pyranoside, papyriferoside A (1), was isolated and its structure was determined on the basis of 1D and 2D NMR, HPLC-MS, as well as high resolution mass spectroscopic data. Platyphylloside (4) exerted the strongest cytotoxic activity of all isolated compounds with IC50 values ranging from 10.3 to 13.8 mu M. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.05.018

文献信息

• Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera
  作者：Vakhtang Mshvildadze、Jean Legault、Serge Lavoie、Charles Gauthier、André Pichette

  DOI：10.1016/j.phytochem.2007.05.018

  日期：2007.10

  Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides (1-4), a diarylheptanoid (5), a lignan (6), flavonoids (7-8) and chavicol glycosides (9-10). Among them, the diarylheptanoid glycoside, (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-alpha-L-arabinofuranosyl-(1 -> 6)-beta-D-gluco-pyranoside, papyriferoside A (1), was isolated and its structure was determined on the basis of 1D and 2D NMR, HPLC-MS, as well as high resolution mass spectroscopic data. Platyphylloside (4) exerted the strongest cytotoxic activity of all isolated compounds with IC50 values ranging from 10.3 to 13.8 mu M. (C) 2007 Elsevier Ltd. All rights reserved.