roseobacticide K | 1363984-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七呋喃
• 英文名称: roseobacticide K
• 英文别名: Roseobacticide K；7-[[3-(4-hydroxyphenyl)-2-oxocyclohepta[b]furan-7-yl]disulfanyl]-3-phenylcyclohepta[b]furan-2-one
• CAS: 1363984-15-9
• 化学式: C₃₀H₁₈O₅S₂
• 分子量: 522.602
• InChiKey: MLXVGOSFOASRIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  roseobacticide K 在 1,4-二巯基-2,3-丁二醇 作用下， 以 甲醇 为溶剂， 生成 3-phenyl-7-sulfanylcyclohepta[b]furan-2-one 、 3-(4-hydroxyphenyl)-7-sulfanylcyclohepta[b]furan-2-one
  参考文献：
  名称：

  Roseobacticides: Small Molecule Modulators of an Algal-Bacterial Symbiosis

  摘要：

  Marine bacteria and microalgae engage in dynamic symbioses mediated by small molecules. A recent study of Phaeobacter gallaeciensis, a member of the large roseobacter clade of alpha-proteobacteria, and Emilionia huxleyi, a prominent member of the microphytoplankton found in large algal blooms, revealed that an algal senescence signal produced by E. huxleyi elicits the production of novel algaecides, the roseobacticides, from the bacterial symbiont. In this report, the generality of these findings are examined by expanding the number of potential elicitors. This expansion led to the identification of nine new members of the roseobacticide family, rare bacterial troponoids, which provide insights into both their biological roles and their biosynthesis. The qualitative and quantitative changes in the levels of roseobacticides induced by the additional elicitors and the elicitors' varied efficiencies support the concept of host-targeted roseobacticide production. Structures of the new family members arise from variable substituents at the C3 and C7 positions of the roseobacticide core as the diversifying elements and suggest that the roseobacticides result from modifications and combinations of aromatic amino acids. Together these studies support a model in which algal senescence converts a mutualistic bacterial symbiont into an opportunistic parasite of its hosts.

  DOI：

  10.1021/ja207172s

文献信息

• ROSEOBACTICIDES AND USES THEREOF
  申请人：Kolter Roberto

  公开号：US20130252815A1

  公开（公告）日：2013-09-26

  Embodiments of the invention relate to compounds and methods for controlling algal growth, for example, in bodies of water or surfaces exposed to algae. Provided are compounds having algicidal activities and methods of use of these compounds as well as formulations and compositions comprising the compound having algicidal activities.

  本发明实施例涉及化合物和方法，用于控制藻类生长，例如在水体或暴露于藻类的表面中。提供了具有藻类杀灭活性的化合物以及使用这些化合物的方法，以及包含具有藻类杀灭活性的化合物的配方和组合物。
• US9131687B2
  申请人：——

  公开号：US9131687B2

  公开（公告）日：2015-09-15
• [EN] ROSEOBACTICIDES AND USES THEREOF<br/>[FR] ROSÉOBACTICIDES ET LEURS UTILISATIONS
  申请人：HARVARD COLLEGE

  公开号：WO2012033631A2

  公开（公告）日：2012-03-15

  Embodiments of the invention relate to compounds and methods for controlling algal growth, for example, in bodies of water or surfaces exposed to algae. Provided are compounds having algicidal activities and methods of use of these compounds as well as formulations and compositions comprising the compound having algicidal activities.
• Roseobacticides: Small Molecule Modulators of an Algal-Bacterial Symbiosis
  作者：Mohammad R. Seyedsayamdost、Gavin Carr、Roberto Kolter、Jon Clardy

  DOI：10.1021/ja207172s

  日期：2011.11.16

  Marine bacteria and microalgae engage in dynamic symbioses mediated by small molecules. A recent study of Phaeobacter gallaeciensis, a member of the large roseobacter clade of alpha-proteobacteria, and Emilionia huxleyi, a prominent member of the microphytoplankton found in large algal blooms, revealed that an algal senescence signal produced by E. huxleyi elicits the production of novel algaecides, the roseobacticides, from the bacterial symbiont. In this report, the generality of these findings are examined by expanding the number of potential elicitors. This expansion led to the identification of nine new members of the roseobacticide family, rare bacterial troponoids, which provide insights into both their biological roles and their biosynthesis. The qualitative and quantitative changes in the levels of roseobacticides induced by the additional elicitors and the elicitors' varied efficiencies support the concept of host-targeted roseobacticide production. Structures of the new family members arise from variable substituents at the C3 and C7 positions of the roseobacticide core as the diversifying elements and suggest that the roseobacticides result from modifications and combinations of aromatic amino acids. Together these studies support a model in which algal senescence converts a mutualistic bacterial symbiont into an opportunistic parasite of its hosts.