18-O-formyl-3-isomangostin hydrate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 18-O-formyl-3-isomangostin hydrate
• 英文别名: [4-(5,9-Dihydroxy-8-methoxy-2,2-dimethyl-6-oxo-3,4-dihydrochromeno[7,6-b]chromen-7-yl)-2-methylbutan-2-yl] formate
• 化学式: C₂₅H₂₈O₈
• 分子量: 456.493
• InChiKey: FKNCBEGGZXHDGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲酸 、 α-倒捻子素 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以25%的产率得到18-O-formyl-3-isomangostin hydrate
  参考文献：
  名称：

  Prenylated Xanthones as Potential Antiplasmodial Substances

  摘要：

  山竹素是山竹（Garcinia mangostana）的主要黄酮类化合物，研究了其及一系列合成衍生物对恶性疟原虫（Plasmodium falciparum）的体外抗疟活性。山竹素本身表现出中等活性，但含有烷基氨基官能团的烯丙基黄酮类化合物显示出相当强的抗疟活性。提出了一些结构-活性关系。

  DOI：

  10.1055/s-2006-947190

文献信息

• Cytotoxic and NF-κB Inhibitory Constituents of the Stems of <i>Cratoxylum cochinchinense</i> and Their Semisynthetic Analogues
  作者：Yulin Ren、Susan Matthew、Daniel D. Lantvit、Tran Ngoc Ninh、Heebyung Chai、James R. Fuchs、Djaja D. Soejarto、Esperanza J. Carcache de Blanco、Steven M. Swanson、A. Douglas Kinghorn

  DOI：10.1021/np200051j

  日期：2011.5.27

  A new caged xanthone (1), a new prenylxanthone (2), seven known xanthones, and a known sterol glucoside were isolated from the stems of Cratoxylum cochinchinense, collected in Vietnam. Compounds 1 and 2 were determined structurally by analysis of their spectroscopic data. In addition, five new (10 and 16-19) and eight known prenylated xanthone derivatives were synthesized from the known compounds a-mangostin (3) and cochinchinone A (6). Several of these substances were found to be cytotoxic toward HT-29 human colon cancer cells, with the most potent being 3,6-di-O-acetyl-alpha-mangostin (8, ED50, 1.01 mu M), which was tested further in an in vivo hollow fiber assay, but found to be inactive at the highest dose used (20 mg/kg; ip). Of the substances evaluated in a NF-kappa B p65 inhibition assay, 1,3,7-trihydroxy-2,4-diisoprenylxanthone (5) exhibited the most potent activity (IC50, 2.9 mu M). In a mitochondrial transmembrane potential assay, two new compounds, 1 (IC50, 3.3 mu M) and 10 (IC50, 1.4 mu M), and two known compounds, 3 (alpha-mangostin, IC50, 0.2 mu M) and 11 (3,6-di-O-methyl-alpha-mangostin, IC50, 0.9 mu M), were active. A preliminary analogue development study showed that 3,6-diacetylation and 6-benzoylation both slightly increased the cytotoxicity of a.-mangostin (3), whereas methylation reduced such activity. In contrast, neither acetylation, benzoylation, nor methylation enhanced the cytotoxicity of cochinchinone A (6).