austradixanthone

• 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: austradixanthone
• 英文别名: Austradixanthone；5-[3,8-dihydroxy-6-(hydroxymethyl)-1-methyl-9-oxoxanthen-4-yl]oxy-2,3,4,6-tetrahydroxy-1-methoxy-8-methylxanthen-9-one
• 化学式: C₃₀H₂₂O₁₃
• 分子量: 590.497
• InChiKey: BPTCPKOWYXWSTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  austradixanthone 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以65%的产率得到
  参考文献：
  名称：

  Metabolites from the Fungal Endophyte Aspergillus austroafricanus in Axenic Culture and in Fungal–Bacterial Mixed Cultures

  摘要：

  The endophytic fungus Aspergillus austroafricanus isolated from leaves of the aquatic plant Eichhornia crassipes was fermented axenically on solid rice medium as well as in mixed cultures with Bacillus subtilis or with Streptomyces lividans. Chromatographic analysis of EtOAc extract of axenic cultures afforded two new metabolites, namely, the xanthone dimer austradixanthone (1) and the sesquiterpene (+)-austrosene (2), along with five known compounds (3-7). Austradixanthone (1) represents the first highly oxygenated heterodimeric xanthone derivative. When A. austroafricanus was grown in mixed cultures with B. subtilis or with S. lividans, several diphenyl ethers (8-11) including the new austramide (8) were induced up to 29-fold. The structures of new compounds were unambiguously elucidated using 1D- and 2D-NMR spectroscopy, HRESIMS, and chemical derivatization. Compound 7 exhibited weak cytotoxicity against the murine lymphoma L5178Y cell line (EC50 is 12.6 mu M). In addition, compounds 9 and 10, which were enhanced in mixed fungal/bacterial cultures, proved to be active against Staphylococcus aureus (ATCC 700699) with minimal inhibitory concentrations (MICs) of 25 mu M each (6.6 mu g/mL), whereas compound 11 revealed moderate antibacterial activity against B. subtilis 168 trpC2 with an MIC value of 34.8 mu M (8 mu g/mL).

  DOI：

  10.1021/acs.jnatprod.5b00975

文献信息

• Metabolites from the Fungal Endophyte <i>Aspergillus austroafricanus</i> in Axenic Culture and in Fungal–Bacterial Mixed Cultures
  作者：Weaam Ebrahim、Mona El-Neketi、Laura-Isabell Lewald、Raha S. Orfali、Wenhan Lin、Nidja Rehberg、Rainer Kalscheuer、Georgios Daletos、Peter Proksch

  DOI：10.1021/acs.jnatprod.5b00975

  日期：2016.4.22

  The endophytic fungus Aspergillus austroafricanus isolated from leaves of the aquatic plant Eichhornia crassipes was fermented axenically on solid rice medium as well as in mixed cultures with Bacillus subtilis or with Streptomyces lividans. Chromatographic analysis of EtOAc extract of axenic cultures afforded two new metabolites, namely, the xanthone dimer austradixanthone (1) and the sesquiterpene (+)-austrosene (2), along with five known compounds (3-7). Austradixanthone (1) represents the first highly oxygenated heterodimeric xanthone derivative. When A. austroafricanus was grown in mixed cultures with B. subtilis or with S. lividans, several diphenyl ethers (8-11) including the new austramide (8) were induced up to 29-fold. The structures of new compounds were unambiguously elucidated using 1D- and 2D-NMR spectroscopy, HRESIMS, and chemical derivatization. Compound 7 exhibited weak cytotoxicity against the murine lymphoma L5178Y cell line (EC50 is 12.6 mu M). In addition, compounds 9 and 10, which were enhanced in mixed fungal/bacterial cultures, proved to be active against Staphylococcus aureus (ATCC 700699) with minimal inhibitory concentrations (MICs) of 25 mu M each (6.6 mu g/mL), whereas compound 11 revealed moderate antibacterial activity against B. subtilis 168 trpC2 with an MIC value of 34.8 mu M (8 mu g/mL).