xanthepinone | 1190592-33-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: xanthepinone
• 英文别名: methyl (5R)-5,7-dihydroxy-3-methyl-4,6-dioxooxepino[2,3-b]chromene-5-carboxylate
• CAS: 1190592-33-6
• 化学式: C₁₆H₁₂O₈
• 分子量: 332.266
• InChiKey: FGWWWUNZNJEQQX-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲醇 、 xanthepinone 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 16.0h， 以1 mg的产率得到(R)-5-hydroxy-2-methoxy-3-(2,3-dihydro-2-methoxycarbonyl-4-methyl-3-oxofuran-2-yl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Chromone derivatives from the wood-decay fungus Rhizina sp. BCC 12292

  摘要：

  A new chromone derivative (1), together with the known oxepino[2,3-b] chromones, microsphaeropsones A (2) and B (3), and xanthopinone (4), was isolated from the wood-decay fungus Rhizina sp. BCC 12292. The structure of 1 was elucidated on the basis of NMR spectroscopic and mass spectrometry data. Transformation of 4 into 1 occurred when a solution of 4 in MeOH was treated with p-TsOH or silica gel, which strongly suggested that 1 may be an artifact formed during the processing of the extract. Compound 1 exhibited antimalarial activity with an IC(50) of 5.1 mu g/ml and cytotoxic activities against NCI-H187 and Vero cell lines with respective IC(50) of 6.4 and 1.6 mu g/ml. (C) 2010 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2010.06.001
• 作为产物：
  描述：

  (1R,2R)-microsphaeropsone A 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 48.0h， 以74%的产率得到xanthepinone
  参考文献：
  名称：

  三种内生真菌的Xanthones和Oxepino [2，3-b]色酮

  摘要：

  三个新的代谢物，microsphaeropsones A-C（1 - 3）具有独特的多塞平〔2,3- b ]苯并吡喃-6-酮（环放大呫吨酮）骨架，从该内生真菌分离Microsphaeropsis种，同现他们推定的生物遗传蒽醌前体citreorosein（4）和大黄素（5）。从另一个Microsphaeropsis物种，大量fusidienol A（的8），较少量大黄素（的5）中，已知的芳族氧杂蒽酮9和9b中，新的3,4- dihydrofusidienol A（图8b），和新的芳族黄酮9 c被隔离了。内生菌毛孢霉菌种产生了一种新的芳族x吨酮，seimatoxanthoneA（10）和3,4-dihydroglobosuxanthone A（12），与Microdiplodia sp。的α-diversolonic酯（13）密切相关。其结构主要由广泛的1D决定。和2D NMR实验，并得到1和

  DOI：

  10.1002/chem.200900749

文献信息

• Xanthones and Oxepino[2, 3-<i>b</i>]chromones from Three Endophytic Fungi
  作者：Karsten Krohn、Simeon F. Kouam、Guy M. Kuigoua、Hidayat Hussain、Stephan Cludius-Brandt、Ulrich Flörke、Tibor Kurtán、Gennaro Pescitelli、Lorenzo Di Bari、Siegfried Draeger、Barbara Schulz

  DOI：10.1002/chem.200900749

  日期：2009.11.9

  related to α‐diversolonic ester (13) from Microdiplodia sp.. The structures were determined mainly by extensive 1D and 2D NMR experiments and supported by X‐ray single‐crystal analysis of 1 and the oxidation product 7. The absolute configurations of the microsphaeropsones A–C (1–3) were established by comparison of the electronic and vibrational circular dichroism (ECD and VCD) spectra of 1 with time‐dependent

  三个新的代谢物，microsphaeropsones A-C（1 - 3）具有独特的多塞平〔2,3- b ]苯并吡喃-6-酮（环放大呫吨酮）骨架，从该内生真菌分离Microsphaeropsis种，同现他们推定的生物遗传蒽醌前体citreorosein（4）和大黄素（5）。从另一个Microsphaeropsis物种，大量fusidienol A（的8），较少量大黄素（的5）中，已知的芳族氧杂蒽酮9和9b中，新的3,4- dihydrofusidienol A（图8b），和新的芳族黄酮9 c被隔离了。内生菌毛孢霉菌种产生了一种新的芳族x吨酮，seimatoxanthoneA（10）和3,4-dihydroglobosuxanthone A（12），与Microdiplodia sp。的α-diversolonic酯（13）密切相关。其结构主要由广泛的1D决定。和2D NMR实验，并得到1和
• Chromone derivatives from the wood-decay fungus Rhizina sp. BCC 12292
  作者：Masahiko Isaka、Malipan Sappan、Patchanee Auncharoen、Prasert Srikitikulchai

  DOI：10.1016/j.phytol.2010.06.001

  日期：2010.9

  A new chromone derivative (1), together with the known oxepino[2,3-b] chromones, microsphaeropsones A (2) and B (3), and xanthopinone (4), was isolated from the wood-decay fungus Rhizina sp. BCC 12292. The structure of 1 was elucidated on the basis of NMR spectroscopic and mass spectrometry data. Transformation of 4 into 1 occurred when a solution of 4 in MeOH was treated with p-TsOH or silica gel, which strongly suggested that 1 may be an artifact formed during the processing of the extract. Compound 1 exhibited antimalarial activity with an IC(50) of 5.1 mu g/ml and cytotoxic activities against NCI-H187 and Vero cell lines with respective IC(50) of 6.4 and 1.6 mu g/ml. (C) 2010 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.