3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1->3)-(2-O-acetyl-α-L-arabinopyranoside)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1->3)-(2-O-acetyl-α-L-arabinopyranoside)
• 英文别名: 3β,17α-dihydroxy-16β-[[O-(2-O-(3,4-dimethoxybenzoyl)-β-D-xylopyranosyl)-(1→3) -2-O-acetyl-α-L-arabinopyranosyl]oxy]cholest-5-en-22-one；3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-(2-O-acetyl-α-L-arabinopyranoside)；[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 3,4-dimethoxybenzoate
• 化学式: C₄₈H₇₀O₁₆
• 分子量: 903.074
• InChiKey: KQJXNSWVFJLYMH-AQFSOBMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  64
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  226
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1->3)-(2-O-acetyl-α-L-arabinopyranoside) 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以1.0 mg的产率得到藜芦酸
  参考文献：
  名称：

  Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae

  摘要：

  Phytochemical examination of the bulbs of Ornithogalum saundersiae led to the isolation of three new acylated cholestane glycosides. Their structures were elucidated, on the basis of the spectroscopic data and chemical evidences, and by comparing them with those of known compounds, as 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one 16-O-beta-D-xylopyranosyl-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside), 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-Xylopyranosyl)-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside) and 3beta,16beta,17alpha-trihydroxy-cholest-5-en-22-one 16-O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside). Inhibitory activity on cyclic AMP phosphodiesterase of the cholestane glycosides was evaluated.

  DOI：

  10.1016/s0031-9422(00)97565-4

文献信息

• Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae
  作者：Satoshi Kubo、Yoshihiro Mimaki、Miki Terao、Yutaka Sashida、Tamotsu Nikaido、Taichi Ohmoto

  DOI：10.1016/s0031-9422(00)97565-4

  日期：1992.1

  Phytochemical examination of the bulbs of Ornithogalum saundersiae led to the isolation of three new acylated cholestane glycosides. Their structures were elucidated, on the basis of the spectroscopic data and chemical evidences, and by comparing them with those of known compounds, as 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one 16-O-beta-D-xylopyranosyl-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside), 3beta,16beta,17alpha-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-Xylopyranosyl)-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside) and 3beta,16beta,17alpha-trihydroxy-cholest-5-en-22-one 16-O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1-->3)-(2-O-acetyl-alpha-L-arabinopyranoside). Inhibitory activity on cyclic AMP phosphodiesterase of the cholestane glycosides was evaluated.