1,6-bis(1-hydroxy-4-oxo-2,5-cyclohexadiene-1-acetyl)-2,3-bis(benzeneacetyl)-β-glucopyranoside | 1221252-38-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1,6-bis(1-hydroxy-4-oxo-2,5-cyclohexadiene-1-acetyl)-2,3-bis(benzeneacetyl)-β-glucopyranoside
• 英文别名: jacaglabroside A；[(2S,3R,4S,5R,6R)-5-hydroxy-2-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetyl]oxy-6-[[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetyl]oxymethyl]-3-(2-phenylacetyl)oxyoxan-4-yl] 2-phenylacetate
• CAS: 1221252-38-5
• 化学式: C₃₈H₃₆O₁₄
• 分子量: 716.695
• InChiKey: SPQIICSVRHBKJU-SGJBUNNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  209
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,6-bis(1-hydroxy-4-oxo-2,5-cyclohexadiene-1-acetyl)-2,3-bis(benzeneacetyl)-β-glucopyranoside 在 硫酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 可得然胶
  参考文献：
  名称：

  Jacaranone-Derived Glucosidic Esters from Jacaranda glabra and Their Activity against Plasmodium falciparum

  摘要：

  In a survey of plants from Ecuador with antiprotozoal activity, Jacaranda glabra was found to show promising activity against the Plasmodium falciparum K1 strain. Subsequently, activity-guided isolation of the dichloromethane extract from the leaves of J. glabra afforded four new phenylethanoid glucosides containing jacaranone-type moieties (1-4), named jacaglabrosides A-D. Their chemical structures were identified using NMR spectroscopy and MS techniques. The compounds were found to be active in vitro against the P. falciparum K1 strain (IC(50) 1, 1.02; 2, 0.56; 3, 0.56; and 4, 0.55 mu g/mL) and generally possessed a low cytotoxicity toward L-6 cells, with the exception of compound 1 (IC(50) 1, 8.3; 2, >90; 3, 87; and 4, 85 mu g/mL).

  DOI：

  10.1021/np900528m

文献信息

• Jacaranone-Derived Glucosidic Esters from <i>Jacaranda glabra</i> and Their Activity against <i>Plasmodium falciparum</i>
  作者：M. Salomé Gachet、Olaf Kunert、Marcel Kaiser、Reto Brun、Ricardo A. Muñoz、Rudolf Bauer、Wolfgang Schühly

  DOI：10.1021/np900528m

  日期：2010.4.23

  In a survey of plants from Ecuador with antiprotozoal activity, Jacaranda glabra was found to show promising activity against the Plasmodium falciparum K1 strain. Subsequently, activity-guided isolation of the dichloromethane extract from the leaves of J. glabra afforded four new phenylethanoid glucosides containing jacaranone-type moieties (1-4), named jacaglabrosides A-D. Their chemical structures were identified using NMR spectroscopy and MS techniques. The compounds were found to be active in vitro against the P. falciparum K1 strain (IC(50) 1, 1.02; 2, 0.56; 3, 0.56; and 4, 0.55 mu g/mL) and generally possessed a low cytotoxicity toward L-6 cells, with the exception of compound 1 (IC(50) 1, 8.3; 2, >90; 3, 87; and 4, 85 mu g/mL).