spiromastixone F | 1571073-11-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: spiromastixone F
• 英文别名: Spiromastixone F；2,8,10-trichloro-3,9-dihydroxy-1,7-dipropylbenzo[b][1,4]benzodioxepin-6-one
• CAS: 1571073-11-4
• 化学式: C₁₉H₁₇Cl₃O₅
• 分子量: 431.7
• InChiKey: OLDOFECIAGEREX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 spiromastixone F 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Spiromastixones A–O, Antibacterial Chlorodepsidones from a Deep-Sea-Derived Spiromastix sp. Fungus

  摘要：

  Fifteen new depsidone-based analogues named spiromastixones A-O (1-15) were isolated from the fermentation broth of a deep-sea Spiromastix sp. fungus. Their structures were elucidated on the basis of extensive NMR and mass spectroscopic analysis in association with chemical conversion. Spiromastixones A-O are classified into two subtypes based on the orientation of ring C relative to ring A, while the n-propyl substituents on rings A and C are rarely seen in natural products. Most analogues are substituted by various numbers of chlorine atoms. All compounds exhibited significant inhibition against Gram-positive bacteria including Staphylococcus aureus, Bacillus thuringiensis, and Bacillus subtilis with MIC values ranging from 0.125 to 8.0 mu g/mL. In addition, compounds 6-10 displayed potent inhibitory effects against methicillin-resistant bacterial strains of S. aureus (MRSA) and S. epidermidis (MRSE), while 10 also inhibited the growth of the vancomycin-resistant bacteria Enterococcus faecalis and E. faecium (VRE). The structure activity relationships are discussed.

  DOI：

  10.1021/np5000457

文献信息

• Spiromastixones A–O, Antibacterial Chlorodepsidones from a Deep-Sea-Derived <i>Spiromastix</i> sp. Fungus
  作者：Siwen Niu、Dong Liu、Xinxin Hu、Peter Proksch、Zhongzhe Shao、Wenhan Lin

  DOI：10.1021/np5000457

  日期：2014.4.25

  Fifteen new depsidone-based analogues named spiromastixones A-O (1-15) were isolated from the fermentation broth of a deep-sea Spiromastix sp. fungus. Their structures were elucidated on the basis of extensive NMR and mass spectroscopic analysis in association with chemical conversion. Spiromastixones A-O are classified into two subtypes based on the orientation of ring C relative to ring A, while the n-propyl substituents on rings A and C are rarely seen in natural products. Most analogues are substituted by various numbers of chlorine atoms. All compounds exhibited significant inhibition against Gram-positive bacteria including Staphylococcus aureus, Bacillus thuringiensis, and Bacillus subtilis with MIC values ranging from 0.125 to 8.0 mu g/mL. In addition, compounds 6-10 displayed potent inhibitory effects against methicillin-resistant bacterial strains of S. aureus (MRSA) and S. epidermidis (MRSE), while 10 also inhibited the growth of the vancomycin-resistant bacteria Enterococcus faecalis and E. faecium (VRE). The structure activity relationships are discussed.