cowaxanthone B

• 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: cowaxanthone B
• 英文别名: 6-O-methyl-α-mangostin；1,3-dihydroxy-6,7-dimethoxy-2,8-diprenylxanthone；1,3-dihydroxy-6,7-dimethoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: BLZDSTHKFQEOIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  α-倒捻子素 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以37%的产率得到cowaxanthone B
  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

• Potent Activity against Multidrug-Resistant <i>Mycobacterium tuberculosis</i> of α-Mangostin Analogs
  作者：Pichit Sudta、Payung Jiarawapi、Apichart Suksamrarn、Poonpilas Hongmanee、Sunit Suksamrarn

  DOI：10.1248/cpb.c12-00874

  日期：——

  A new series of mangostin analogs of natural α-mangostin from mangosteen was prepared and their antimycobacterial activity was evaluated in vitro against Mycobacterium tuberculosis H37Ra. The results showed that the monoalkyl tetrahydro α-mangostin analogs displayed increased antimycobacterial activity as compared with the lead natural xanthone, α-mangostin. Among the tested compounds, 6-methoxytetrahydro α-mangostin (16) exhibited the most potent antimycobacterial activity with minimum inhibitory concentration (MIC) of 0.78 µg/mL. The activity of the monoalkylated and monoacylated tetrahydro α-mangostins decreases as the length of carbon chain increases. The methyl ether analog was also active against the multidrug-resistant (MDR) strains with pronounced MICs of 0.78–1.56 µg/mL.

  研究人员从山竹中提取了天然α-山竹甙，制备了一系列新的山竹甙类似物，并在体外评估了它们对结核分枝杆菌 H37Ra 的抗霉菌活性。结果表明，单烷基四氢 α-山竹酮类似物的抗霉菌活性高于主要天然氧杂蒽酮 α-山竹酮。在测试的化合物中，6-甲氧基四氢 α-曼戈斯汀（16）的抗霉菌活性最强，最低抑菌浓度（MIC）为 0.78 µg/mL。单烷基化和单酰化四氢 α-曼戈斯汀的活性随着碳链长度的增加而降低。甲醚类似物对耐多药（MDR）菌株也有活性，其显著的 MIC 值为 0.78-1.56 µg/mL。
• A PROCESS FOR PRODUCING GAMMA MANGOSTIN
  申请人：Gokaraju Ganga Raju

  公开号：US20100292490A1

  公开（公告）日：2010-11-18

  A process for the production of γ-mangostin comprising the steps of preparing O-methyl γ-mangostin preferably from plants, subjecting the pure or partially pure O-methylated γ-mangostin to demethylation reaction procedure followed by purification of the said demethylated product to obtain pure γ-mangostin.

  一种制备γ-芒果皮素的工艺，包括以下步骤：从植物中制备O-甲基γ-芒果皮素，然后将纯或部分纯的O-甲基化的γ-芒果皮素经过脱甲基反应程序，并对所述脱甲基产物进行纯化以获得纯的γ-芒果皮素。
• 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.
• US8461360B2
  申请人：——

  公开号：US8461360B2

  公开（公告）日：2013-06-11
• [EN] A PROCESS FOR PRODUCING ?-MANGOSTIN<br/>[FR] PROCÉDÉ POUR PRODUIRE DE LA ?-MANGOSTINE
  申请人：GOKARAJU GANGA RAJU

  公开号：WO2009093259A2

  公开（公告）日：2009-07-30

  A process for the production of γ-mangostin comprising the steps of preparing O-methyl γ-mangostin preferably from plants, subjecting the pure or partially pure O-methylated γ- mangostin to demethylation reaction procedure followed by purification of the said demethylated product to obtain pure γ-mangostin.