mangostanin

• 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: mangostanin
• 英文别名: 4,8-dihydroxy-2-(2-hydroxypropan-2-yl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrofuro[3,2-b]xanthen-5-one
• 化学式: C₂₄H₂₆O₇
• 分子量: 426.466
• InChiKey: PDCFTPUXIGMZDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  mangostanin 在 吡啶 、 氯化亚砜 作用下， 生成 4-Hydroxy-2-isopropenyl-7,8-dimethoxy-6-(3-methyl-but-2-enyl)-2,3-dihydro-1,10-dioxa-cyclopenta[b]anthracen-5-one
  参考文献：
  名称：

  来自山竹心材的氧杂蒽酮

  摘要：

  从缅甸藤黄心材的己烷提取物中分离出 12 种氧杂蒽酮。它们的结构是使用 1D 和 2D NMR 技术确定的

  DOI：

  10.1016/s0031-9422(02)00142-5
• 作为产物：
  描述：

  α-倒捻子素 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以25%的产率得到mangostanin
  参考文献：
  名称：

  Chemistry of α-mangostin. Studies on the semisynthesis of minor xanthones from Garcinia mangostana

  摘要：

  alpha-Mangostin is the major prenylated xanthone from Garcinia mangostana and it has been used also in recent times as starting material for the semisynthetic preparation of various biologically active derivatives. Its structure is characterised by the presence of few functional groups amenable to chemical manipulations, but present in the molecule in multiple instances (three phenolic hydroxyl groups, two prenyl chains and two unsubstituted aromatic carbons). This study represents a first approach to the systematic investigation of the reactivity of alpha-mangostin and describes the semisynthesis of some minor xanthones isolated from G. mangostana.

  DOI：

  10.1080/14786419.2014.986729

文献信息

• Design, synthesis and structure–activity relationships of mangostin analogs as cytotoxic agents
  作者：Xiao-Qian Chi、Cheng-Ting Zi、Hong-Mei Li、Liu Yang、Yong-Feng Lv、Jin-Yu Li、Bo Hou、Fu-Cai Ren、Jiang-Miao Hu、Jun Zhou

  DOI：10.1039/c8ra08409b

  日期：——

  their cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) using MTT assays. Most of them showed cytotoxicity and most of all, compounds 1a and 2h showed the highest cytotoxic potency by HL-60 cancer cell lines with IC50 values of 5.96 μM and 6.90 μM respectively; compound 3e showed the highest cytotoxic potency against SMMC-7221 cancer cell line with

  为了更好地了解山竹素的构效关系，设计合成了一系列基于α-山竹素的呫吨酮衍生物。使用 MTT 分析评估了所有化合物对一组五种人类癌细胞系（HL-60、SMMC-7721、A-549、MCF-7 和 SW480）的细胞毒性。它们中的大多数显示出细胞毒性，最重要的是，化合物1a和2h对HL-60癌细胞系显示出最高的细胞毒性效力，IC 50值分别为5.96 μM和6.90 μM；化合物3e对SMMC-7221癌细胞系表现出最高的细胞毒效力，IC 50值为3.98 μM；化合物2e和2m分别对 HL-60 和 SMMC-7221 癌细胞系表现出比 α-mangostin 更低的细胞毒性但更高的选择性。构效关系分析表明，异戊烯基团在 C-8 上的维持对细胞毒活性至关重要。
• Chemistry of α-mangostin. Studies on the semisynthesis of minor xanthones from <i>Garcinia mangostana</i>
  作者：Carlo F. Morelli、Marco Biagiotti、Valeria M. Pappalardo、Marco Rabuffetti、Giovanna Speranza

  DOI：10.1080/14786419.2014.986729

  日期：2015.4.18

  alpha-Mangostin is the major prenylated xanthone from Garcinia mangostana and it has been used also in recent times as starting material for the semisynthetic preparation of various biologically active derivatives. Its structure is characterised by the presence of few functional groups amenable to chemical manipulations, but present in the molecule in multiple instances (three phenolic hydroxyl groups, two prenyl chains and two unsubstituted aromatic carbons). This study represents a first approach to the systematic investigation of the reactivity of alpha-mangostin and describes the semisynthesis of some minor xanthones isolated from G. mangostana.
• Xanthones from the heartwood of Garcinia mangostana
  作者：L Nilar

  DOI：10.1016/s0031-9422(02)00142-5

  日期：2002.7

  Twelve xanthones were isolated from the hexane extract of the heartwood of Garcinia mangostana from Myanmar. Their structures were determined using 1D and 2D NMR techniques

  从缅甸藤黄心材的己烷提取物中分离出 12 种氧杂蒽酮。它们的结构是使用 1D 和 2D NMR 技术确定的