3,5-di-O-methylcytosporone F | 1004304-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-O-methylcytosporone F
• 英文别名: ethyl 2-[3,5-dimethoxy-2-[(2E,4E)-octa-2,4-dienoyl]phenyl]acetate
• CAS: 1004304-40-8
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: KXBHORLFUBFZHZ-BNFZFUHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-di-O-methylcytosporone F 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以5.3 mg的产率得到3,5-di-O-methylcyclosporone B
  参考文献：
  名称：

  Uncovering Biosynthetic Potential of Plant-Associated Fungi: Effect of Culture Conditions on Metabolite Production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii

  摘要：

  In an attempt to uncover the biosynthetic potential of plant-associated fungi, the effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii was investigated. These studies indicated that the production of the major metabolites by P. quadriseptata differ when the water used to make the media was changed from tap water to distilled water. It resulted in the isolation of six new secondary metabolites, cytosporones F-I (1-4), quadriseptin A (5), and 5'-hydroxymonocillin III (6) together with monocillin III (7), a metabolite new to P. quadriseptata, in addition to monocillin I (8), a previously known metabolite from this organism. Aposphaerin B (9) encountered was suspected to be an artifact originating from cytosporone F (1). Incorporation of heavy metal ions to P. quadriseptata culture medium induced production of monocillin 1 (8) by this fungus. Cultivation of C. chiversii in liquid medium resulted in the isolation of chaetochromin A (12) as the major metabolite instead of radicicol (10), the major constituent of this organism when grown in a solid medium. Compounds 1-7 and 12 were evaluated for their potential to inhibit Hsp90 and antiproliferative activity toward the cancer cell lines NCI-H460, MCF-7, and SF-268. Only compounds 6, 7, and 8 exhibited significant activity in both assays.

  DOI：

  10.1021/np070504b
• 作为产物：
  描述：

  cytosporone F 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以8.6 mg的产率得到3,5-di-O-methylcytosporone F
  参考文献：
  名称：

  Uncovering Biosynthetic Potential of Plant-Associated Fungi: Effect of Culture Conditions on Metabolite Production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii

  摘要：

  In an attempt to uncover the biosynthetic potential of plant-associated fungi, the effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii was investigated. These studies indicated that the production of the major metabolites by P. quadriseptata differ when the water used to make the media was changed from tap water to distilled water. It resulted in the isolation of six new secondary metabolites, cytosporones F-I (1-4), quadriseptin A (5), and 5'-hydroxymonocillin III (6) together with monocillin III (7), a metabolite new to P. quadriseptata, in addition to monocillin I (8), a previously known metabolite from this organism. Aposphaerin B (9) encountered was suspected to be an artifact originating from cytosporone F (1). Incorporation of heavy metal ions to P. quadriseptata culture medium induced production of monocillin 1 (8) by this fungus. Cultivation of C. chiversii in liquid medium resulted in the isolation of chaetochromin A (12) as the major metabolite instead of radicicol (10), the major constituent of this organism when grown in a solid medium. Compounds 1-7 and 12 were evaluated for their potential to inhibit Hsp90 and antiproliferative activity toward the cancer cell lines NCI-H460, MCF-7, and SF-268. Only compounds 6, 7, and 8 exhibited significant activity in both assays.

  DOI：

  10.1021/np070504b

文献信息

• Uncovering Biosynthetic Potential of Plant-Associated Fungi: Effect of Culture Conditions on Metabolite Production by <i>Paraphaeosphaeria quadriseptata</i> and <i>Chaetomium chiversii</i>
  作者：Priyani A. Paranagama、E. M. Kithsiri Wijeratne、A. A. Leslie Gunatilaka

  DOI：10.1021/np070504b

  日期：2007.12.1

  In an attempt to uncover the biosynthetic potential of plant-associated fungi, the effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii was investigated. These studies indicated that the production of the major metabolites by P. quadriseptata differ when the water used to make the media was changed from tap water to distilled water. It resulted in the isolation of six new secondary metabolites, cytosporones F-I (1-4), quadriseptin A (5), and 5'-hydroxymonocillin III (6) together with monocillin III (7), a metabolite new to P. quadriseptata, in addition to monocillin I (8), a previously known metabolite from this organism. Aposphaerin B (9) encountered was suspected to be an artifact originating from cytosporone F (1). Incorporation of heavy metal ions to P. quadriseptata culture medium induced production of monocillin 1 (8) by this fungus. Cultivation of C. chiversii in liquid medium resulted in the isolation of chaetochromin A (12) as the major metabolite instead of radicicol (10), the major constituent of this organism when grown in a solid medium. Compounds 1-7 and 12 were evaluated for their potential to inhibit Hsp90 and antiproliferative activity toward the cancer cell lines NCI-H460, MCF-7, and SF-268. Only compounds 6, 7, and 8 exhibited significant activity in both assays.