1-异倒捻子素水合物 | 26063-95-6

• 物质功能分类: 天然产物 - 氧杂蒽酮
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 1-异倒捻子素水合物
• 英文名称: 1-isomangostin hydrate
• 英文别名: 5,9-dihydroxy-11-(3-hydroxy-3-methylbutyl)-10-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-a]xanthen-12-one
• CAS: 26063-95-6
• 化学式: C₂₄H₂₈O₇
• 分子量: 428.482
• InChiKey: QEERGWNVXZILOR-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  261-263°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

制备方法与用途

作用

1-异倒捻子素水合物是从藤黄科藤黄属植物山竹子（Garcinia mangostana L.）果壳中分离出的主要生物活性化合物。迄今为止，已从山竹的果皮、叶、根和心材等部位分离得到60多个氧杂蒽酮，其中α-倒捻子素和1-异倒捻子素水合物在山竹中的含量较为丰富。这些化合物具有不同程度的杀菌消炎、抗痢疾以及治疗溃疡的作用。

制备

步骤 1：将40g 山竹提取物加入1000ml 反应瓶中，依次添加300ml 二氯乙烷、300ml 吡啶和64g 无水三氯化铝，并加入0.1g 碘化钠。加热回流反应3小时后冷却反应液。随后向其中加入6g 浓盐酸中和至弱酸性，减压回收二氯乙烷，放冷得到1-异倒捻子素水合物粗品约30g。

步骤 2：将上述粗品30g 加入600ml 无水乙醇进行重结晶，并加入5g 活性炭脱色。浓缩乙醇至原体积的三分之一后放置结晶，24小时后抽滤得到98%纯度的1-异倒捻子素水合物精品约21g。

反应信息

• 作为产物：
  描述：

  异曼果斯廷 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以75%的产率得到1-异倒捻子素水合物
  参考文献：
  名称：

  修饰的四加氧合氧杂蒽酮类似物作为抗MRSA和铜绿假单胞菌的代理及其与万古霉素的协同作用。

  摘要：

  评价了五个从C. cochinchinense和G. mangostana分离出的氧杂蒽酮，并测试了其抗菌活性。分离的4和5显示出有效的抗MRSA和铜绿假单胞菌活性，但是通过ADMET预测显示出不良的药代动力学性质。它导致我们通过在酸性条件下部分修饰4和5以产生14个类似物来改善4和5的药代动力学特性。发现类似物4b，4d和5b具有适当的药代动力学性质，而只有4b显示出最佳的抗MRSA和铜绿假单胞菌。活动。SEM结果表明，4b可能与MRSA和铜绿假单胞菌相互作用或破坏细胞壁。而且，组合图4b和万古霉素表现出对MRSA和协同效应铜绿假单胞菌4.98的MIC值（MIC = 18.75 μ克/毫升为图4b）和9.52 μ克/毫升（MIC = 75 μ克/毫升为图4b）， 分别。

  DOI：

  10.1016/j.bmcl.2020.127494

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.
• 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).
• XANTHONE-RICH PLANT EXTRACTS OR COMPOUNDS THEREFROM FOR MODULATING DISEASES OF THE CENTRAL NERVOUS SYSTEM AND RELATED DISORDERS
  申请人：DEAKIN UNIVERSITY

  公开号：EP3110414B1

  公开（公告）日：2020-09-30
• [EN] XANTHONE-RICH PLANT EXTRACTS OR COMPOUNDS THEREFROM FOR MODULATING DISEASES OF THE CENTRAL NERVOUS SYSTEM AND RELATED DISORDERS<br/>[FR] EXTRAITS DE PLANTE RICHES EN XANTHONE OU COMPOSÉS DÉRIVÉS DE CEUX-CI POUR LA MODULATION DE MALADIES DU SYSTÈME NERVEUX CENTRAL ET DE TROUBLES ASSOCIÉS
  申请人：UNIV DEAKIN

  公开号：WO2015127512A1

  公开（公告）日：2015-09-03

  The invention relates to a method of treatment and/or prophylaxis of a disease or disorder of the central nervous system comprising administering to a mammal in need thereof an effective amount of a xanthone-rich plant extract, or a compound derived from a xanthone-rich plant extract. The invention also relates to use of a xanthone-rich plant extract, or a compound derived from a xanthone-rich plant extract, in the preparation of a medicament for the treatment and/or prophylaxis of a disease or disorder of the central nervous system and to a xanthone-rich plant extract, or a compound derived from a xanthone-rich plant extract, for use in the treatment and/or prophylaxis of a disease or disorder of the central nervous system.