title: Identification, library synthesis and anti-vibriosis activity of 2-benzyl-4-chlorophenol from cultures of the marine bacterium Shewanella halifaxensis.
abstract: Summer Gut Syndrome (SGS) is caused by various Vibrio bacterial species and can have negative effects on aquaculture farms worldwide. In New Zealand, SGS is caused by Vibrio harveyii infecting King Salmon (Oncorhynchus tshawytscha). To find leads for the prevention of SGS, we screened the inhibitory effects of 16 strains of Shewanella upon V. harveyii growth in competitive solid phase cultures. The detailed investigation of Shewanella halifaxensis IRL548 revealed 2-benzyl-4-chlorophenol (1), a known, commercially available antibacterial agent, as the major bioactive component. Synthesis of a small library of congeners to confirm the natural product identity and to provide a structure-activity relationship for the observed activity was also completed. Compound 1 exhibits moderate activity against two pathogenic microorganisms.
authors.affiliation: Center for Biodiscovery, and School of Chemical and Physical Sciences, Victoria University of Wellington, PO BOX 600, Kelburn, Wellington 6140, New Zealand.
authors.forename: Sarah L
authors.initials: SL
authors.lastname: Moore
authors.affiliation: Center for Biodiscovery, and School of Chemical and Physical Sciences, Victoria University of Wellington, PO BOX 600, Kelburn, Wellington 6140, New Zealand.
authors.forename: Lucile
authors.initials: L
authors.lastname: Berthomier
authors.affiliation: Center for Biodiscovery, and School of Chemical and Physical Sciences, Victoria University of Wellington, PO BOX 600, Kelburn, Wellington 6140, New Zealand.
authors.forename: Chriselle D
authors.initials: CD
authors.lastname: Braganza
authors.affiliation: Center for Biodiscovery, and School of Biological Sciences, Victoria University of Wellington, PO BOX 600, Kelburn, Wellington 6140, New Zealand.
authors.forename: Joanna K
authors.initials: JK
authors.lastname: MacKichan
authors.affiliation: Integrated Bioactive Technologies Group, Callaghan Innovation, Gracefield, PO Box 31310, Lower Hutt 5040, New Zealand.
authors.forename: Jason L
authors.initials: JL
authors.lastname: Ryan
authors.affiliation: Chemical and Process Engineering, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Visnovsky
authors.affiliation: Center for Biodiscovery, and School of Chemical and Physical Sciences, Victoria University of Wellington, PO BOX 600, Kelburn, Wellington 6140, New Zealand. Electronic address: rob.keyzers@vuw.ac.nz.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Keyzers
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004003:Dichlorophen / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D020592:Shewanella / Q000737:chemistry* / Q000378:metabolism; D054852:Small Molecule Libraries / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014735:Vibrio Infections / Q000188:drug therapy; D014737:Vibrionaceae / Q000187:drug effects*
chemical_list: D000900:Anti-Bacterial Agents; D054852:Small Molecule Libraries; C004660:clorophene; D004003:Dichlorophen
keywords: Chlorophene; Chlorophenol; New Zealand; Probiotic; Shewanella