Antibacterial benzaldehydes produced by seaweed-derived Streptomyces atrovirens PK288-21

Abstract

Marine-derived actinomycetes (87 strains isolated from seaweed and 98 strains isolated from marine sediment) were screened for antimicrobial activity against bacterial fish pathogens. The most potent active strain (PK288-21) isolated from the rhizosphere of the marine seaweed Undaria pinnatifida was identified as Streptomyces atrovirens by 16S rDNA sequence analysis. Two active compounds were isolated from a culture extract of strain PK288-21 by silica-gel flash chromatography and high-performance liquid chromatography. The structures of the two compounds were identified as 2-hydroxy-5-(3-methylbut-2-enyl)benzaldehyde (B1) and 2-hepta-1,5-dienyl-3,6-dihydroxy-5-(3-methylbut-2-enyl) benzaldehyde (B2) by nuclear magnetic resonance and high-resolution fast atomic bombardment mass spectroscopy. The antimicrobial activities of the two compounds were tested against bacterial fish pathogens and expressed in terms of the minimum inhibitory concentration (MIC). Metabolite production was found to be optimized in A1BFe medium following the screening of eight different media. The two compounds killed Edwardsiella tarda after 12 h and Streptococcus iniae after 16 h at the MIC. Compound B1, 2-hydroxy-5-(3-methylbut-2-enyl)benzaldehyde, is a new benzaldehyde derivative, and this is the first time that either of these compounds have been reported in the genus Streptomyces.