1-O-(β-D-glucopyranosyl)-(2S,3S,4R)-2N-[(2'R)-2'-hydroxy-tetracosanoyl]-9Z-octadecene-1,3,4-triol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 1-O-(β-D-glucopyranosyl)-(2S,3S,4R)-2N-[(2'R)-2'-hydroxy-tetracosanoyl]-9Z-octadecene-1,3,4-triol
• 英文别名: sumatranoside；(2R)-N-[(Z,2S,3S,4R)-3,4-dihydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-9-en-2-yl]-2-hydroxytetracosanamide
• 化学式: C₄₈H₉₃NO₁₀
• 分子量: 844.267
• InChiKey: AQVPIVKUWUUSPC-JRRYQIPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  59
• 可旋转键数：
  41
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  189
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-O-(β-D-glucopyranosyl)-(2S,3S,4R)-2N-[(2'R)-2'-hydroxy-tetracosanoyl]-9Z-octadecene-1,3,4-triol 在 lithium hydroxide 作用下， 反应 5.0h， 生成 methyl (2R)-2-hydroxytetracosanoate
  参考文献：
  名称：

  Activity-Guided Fractionation of the Leaves of Ormosia sumatrana Using a Proteasome Inhibition Assay

  摘要：

  Activity-guided fractionation of a chloroform-soluble extract of the leaves of Ormosia sumatrana, using a proteasome inhibition assay, led to the isolation of a new A-type proanthocyanidin derivative, 3'-O-cinnamoylprocyanidin A-2 (1), and a new cerebroside, sumatranoside (2). The structures of these two isolates were determined as epicatechin-(2beta-->O-7',4beta-->8')-epicatechin-3'-O-cinnamate (1) and 1-O-(beta-D-glucopyranosyl)-(2S,3S,4R)-2N-[(2'R)-2'-hydroxy-tetracosanoyl]-9Z-octadecene-1,3,4-triol (2), respectively, by spectroscopic and chemical methods. Sumatranoside (2) exhibited proteasome inhibitory activity with an IC50 value of 30 muM.

  DOI：

  10.1021/np040134g

文献信息

• Activity-Guided Fractionation of the Leaves of <i>Ormosia </i><i>s</i><i>umatrana</i> Using a Proteasome Inhibition Assay
  作者：Bao-Ning Su、Bang Yeon Hwang、Heebyung Chai、Esperanza J. Carcache-Blanco、Leonardus B. S. Kardono、Johar J. Afriastini、Soedarsono Riswan、Robert Wild、Naomi Laing、Norman R. Farnsworth、Geoffrey A. Cordell、Steven M. Swanson、A. Douglas Kinghorn

  DOI：10.1021/np040134g

  日期：2004.11.1

  Activity-guided fractionation of a chloroform-soluble extract of the leaves of Ormosia sumatrana, using a proteasome inhibition assay, led to the isolation of a new A-type proanthocyanidin derivative, 3'-O-cinnamoylprocyanidin A-2 (1), and a new cerebroside, sumatranoside (2). The structures of these two isolates were determined as epicatechin-(2beta-->O-7',4beta-->8')-epicatechin-3'-O-cinnamate (1) and 1-O-(beta-D-glucopyranosyl)-(2S,3S,4R)-2N-[(2'R)-2'-hydroxy-tetracosanoyl]-9Z-octadecene-1,3,4-triol (2), respectively, by spectroscopic and chemical methods. Sumatranoside (2) exhibited proteasome inhibitory activity with an IC50 value of 30 muM.