ABSTRACT
Bioassay-guided isolation of bioactive metabolites from the ethyl acetate extract of a marine Bacillus sp. fermentation broth has led to the discovery of three new 24-membered macrolactones, macrolactins 1-3, which contain an oxetane, an epoxide, and a tetrahydropyran ring, respectively. The configurations of 1-3 were assigned by a combination of coupling constants, ROESY data analysis, and application of the modified Mosher's method. Compounds 1-3 showed in vitro antimicrobial activity.
Subject(s)
Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Bacillus/chemistry , Ethers, Cyclic/isolation & purification , Ethers, Cyclic/pharmacology , Anti-Infective Agents/chemistry , Bacillus subtilis/drug effects , Escherichia coli/drug effects , Ethers, Cyclic/chemistry , Marine Biology , Microbial Sensitivity Tests , Molecular Structure , Saccharomyces cerevisiae/drug effectsABSTRACT
Bioassay-guided isolation of the EtOAc extract of a marine Bacillus sp., cultured in modified Bennett's broth medium, yielded four new antimicrobial fatty acids, named ieodomycins A-D. The planar structures of these new compounds were determined by extensive 1D and 2D NMR and HRESIMS spectroscopic data analysis. Their absolute configurations were elucidated by modified Mosher's method and literature data review. All four new compounds demonstrated antimicrobial activities in vitro.
Subject(s)
Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Bacillus/chemistry , Fatty Acids, Unsaturated/isolation & purification , Fatty Acids, Unsaturated/pharmacology , Anti-Infective Agents/chemistry , Bacillus subtilis/drug effects , Escherichia coli/drug effects , Fatty Acids, Unsaturated/chemistry , Humans , Marine Biology , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Saccharomyces cerevisiae/drug effectsABSTRACT
Bioactivity-guided isolation for the new/novel metabolites from the EtOAc extract obtained from the culture broth of a marine Bacillus sp. 09ID194 followed by chromatographic fractionations and subsequently HPLC purifications led to the isolation of two known macrolides, macrolactins A (1) and Q (2), together with a new glycosylated marcrolide, macrolactin W (3). The chemical structures of compounds 1-3 were assigned based on extensive MS and NMR spectral data analysis and literature review. Compound 3 showed potent antibacterial activity against both Gram-positive and Gram-negative pathogenic bacteria.
Subject(s)
Anti-Bacterial Agents/chemistry , Bacillus/chemistry , Glycosides/chemistry , Macrolides/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Glycosides/isolation & purification , Glycosides/pharmacology , Macrolides/isolation & purification , Macrolides/pharmacology , Magnetic Resonance Spectroscopy , Molecular Structure , Republic of KoreaABSTRACT
Three amides, N-salicyloyl-2-aminopropan-1,3-diol (1) and 1-acetyl-N-salicyloyl-2-aminopropan-3-ol (2) including a natural product, N-salicyloyl-2-aminopropan-1-ol (3) were isolated from an ethyl acetate extract of the culture filtrate of Streptomyces hygroscopicus [corrected] The structures of these compounds were unambiguously established by interpretation of their spectral data including, a series of 1D and 2D-NMR and MS analyses. Compounds 1-3 showed significant antibacterial activity against a wide range of Gram positive and Gram negative bacteria.
