Isolation of Coralmycins A and B, Potent Anti-Gram Negative Compounds from the Myxobacteria Corallococcus coralloides M23.

Yu Jin Kim, Hyun-Ju Kim, Geon-Woo Kim, Kyungyun Cho, Shunya Takahashi, Hiroyuki Koshino, Won-Gon Kim
Author Information
  1. Yu Jin Kim: Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.
  2. Hyun-Ju Kim: Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.
  3. Geon-Woo Kim: Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.
  4. Kyungyun Cho: Department of Biotechnology, Hoseo University , Asan 336-795, Korea.
  5. Shunya Takahashi: RIKEN Center for Sustainable Resource Science , Hirosawa 2-1, Wako, Saitama 351-0198, Japan.
  6. Hiroyuki Koshino: RIKEN Center for Sustainable Resource Science , Hirosawa 2-1, Wako, Saitama 351-0198, Japan.
  7. Won-Gon Kim: Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.

Abstract

Two new potent anti-Gram negative compounds, coralmycins A (1) and B (2), were isolated from cultures of the myxobacteria Corallococcus coralloides M23, together with another derivative (3) that was identified as the very recently reported cystobactamid 919-2. Their structures including the relative stereochemistry were elucidated by interpretation of spectroscopic, optical rotation, and CD data. The relative stereochemistry of 3 was revised to "S*R*" by NMR analysis. The antibacterial activity of 1 was most potent against Gram-negative pathogens, including Escherichia coli, Pseudomonas aeruginosa, Acinetobacter baumanii, and Klebsiella pneumoniae, with MICs of 0.1-4 μg/mL; these MICs were 4-10 and 40-100 times stronger than the antibacterial activities of 3 and 2, respectively. Thus, these data indicated that the β-methoxyasparagine unit and the hydroxy group of the benzoic acid unit were critical for antibacterial activity.

MeSH Term

Anti-Bacterial Agents
Asparagine
Aspartic Acid
Depsipeptides
Escherichia coli
Hep G2 Cells
Humans
Klebsiella pneumoniae
Microbial Sensitivity Tests
Molecular Structure
Myxococcales
Nitro Compounds
Nuclear Magnetic Resonance, Biomolecular
Pseudomonas aeruginosa
Structure-Activity Relationship

Chemicals

Anti-Bacterial Agents
Depsipeptides
Nitro Compounds
coralmycin A
coralmycin B
cystobactamid 919-2
Aspartic Acid
Asparagine

Word Cloud

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