Isolation of Coralmycins A and B, Potent Anti-Gram Negative Compounds from the Myxobacteria Corallococcus coralloides M23.
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.
Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.
Yu Jin
YJ
Kim
Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.
Hyun-Ju
HJ
Kim
Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.
Geon-Woo
GW
Kim
Department of Biotechnology, Hoseo University , Asan 336-795, Korea.
Kyungyun
K
Cho
RIKEN Center for Sustainable Resource Science , Hirosawa 2-1, Wako, Saitama 351-0198, Japan.
Shunya
S
Takahashi
RIKEN Center for Sustainable Resource Science , Hirosawa 2-1, Wako, Saitama 351-0198, Japan.
Hiroyuki
H
Koshino
Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology , Yusong, Daejeon 305-806, Korea.
Won-Gon
WG
Kim
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001216:Asparagine / Q000031:analogs & derivatives / Q000737:chemistry; D001224:Aspartic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D056945:Hep G2 Cells; D006801:Humans; D007711:Klebsiella pneumoniae / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D047630:Depsipeptides; D009574:Nitro Compounds; C000620788:coralmycin A; C000620789:coralmycin B; C000600617:cystobactamid 919-2; D001224:Aspartic Acid; D001216:Asparagine