1,3-dihydroxy-6-O-benzoyl-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9-xanthone | 1140525-42-3

• 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: 1,3-dihydroxy-6-O-benzoyl-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9-xanthone
• 英文别名: 6-O-benzoyl-α-mangostin；[6,8-Dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-enyl)-9-oxo-xanthen-3-yl] benzoate；[6,8-dihydroxy-2-methoxy-1,7-bis(3-methylbut-2-enyl)-9-oxoxanthen-3-yl] benzoate
• CAS: 1140525-42-3
• 化学式: C₃₁H₃₀O₇
• 分子量: 514.575
• InChiKey: PZHXWXLAJJOECM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-dihydroxy-6-O-benzoyl-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9-xanthone 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以44%的产率得到α-倒捻子素
  参考文献：
  名称：

  高纯度α-倒捻子素的合成工艺

  摘要：

  本发明涉及一种高纯度天然产物α‑倒捻子素的合成工艺方法，包括：①以工艺提取的α‑倒捻子素为起始原料，在碱的溶剂中与不同酰化试剂反应，重结晶，除去部分杂质，得到纯度较高的酚羟基取代α‑倒捻子素;②合成的中间体酚羟基取代α‑倒捻子素，在溶剂中通过与不同反应试剂脱去保护基，酸碱反萃，重结晶，脱色，进一步纯化，得到高纯度α‑倒捻子素。该方法合成方便，且产率较高，能够满足药品对质量的要求。

  公开号：

  CN103880807B
• 作为产物：
  描述：

  α-倒捻子素 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 1,3-dihydroxy-6-O-benzoyl-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9-xanthone
  参考文献：
  名称：

  高纯度α-倒捻子素的合成工艺

  摘要：

  本发明涉及一种高纯度天然产物α‑倒捻子素的合成工艺方法，包括：①以工艺提取的α‑倒捻子素为起始原料，在碱的溶剂中与不同酰化试剂反应，重结晶，除去部分杂质，得到纯度较高的酚羟基取代α‑倒捻子素;②合成的中间体酚羟基取代α‑倒捻子素，在溶剂中通过与不同反应试剂脱去保护基，酸碱反萃，重结晶，脱色，进一步纯化，得到高纯度α‑倒捻子素。该方法合成方便，且产率较高，能够满足药品对质量的要求。

  公开号：

  CN103880807B

文献信息

• Synthesis and Antitumor Activities of α-,γ-mangostin Derivatives
  作者：Kai Cheng、Gui-lin Zhang、Sheng-xiang Qiu、Yan-qing Liu、Yan-fei Wang、Song Liu、Yan Shan、Bo Yu、Yu Lu

  DOI：10.2174/1570180811666131217003216

  日期：2013.12.16

  isolated from Garcinia Mangostana L. as representative Xanthone's natural products of plant origin, revealed high activity of antitumor, antioxidation and other diverse pharmacological activities. A series of α, γ-Mangostin derivatives LT-1~17 has been synthesized, and confirmed by 1H NMR, 13C NMR, MS(supplement file). Compounds LT-2~17, as novel Xanthone, have been reported for the first time. Their antitumor

  α？-Mangostin和？-Mangostin主要从藤黄（Garcinia Mangostana L.）中分离出来，作为代表Xanthone的植物来源天然产物，具有很高的抗肿瘤，抗氧化和其他多种药理活性。合成了一系列α，γ，Mangostin衍生物LT-1〜17，并通过1 H NMR，13 C NMR，MS（补充文件）进行了确认。化合物LT-2〜17作为新型的黄酮，已被首次报道。已经通过MTT方法在细胞系：A549，K562，CNE，KB-3-1，MCF-7和HepG2中研究了它们的抗肿瘤活性。许多化合物显示出有效的抗肿瘤活性，在某些情况下甚至比Mangostins更高（更有效）。具有IC 50的化合物3A549细胞系中的1.73 µM值是两倍，比ADM（阿霉素）和α？，γ？-Mangostin活性更高，并且具有最强的抗肿瘤活性（IC 50 = 2.15 µM）。所有合成衍生物中的MCF
• 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。
• 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).