Abstract
To investigate the anti-Saprolegnia activities of chalconic compounds, nine dialkoxychalcones 2–10, along with their key building block 2′,4′-dihydroxychalcone 1, were evaluated for their potential oomycide activities against Saprolegnia australis strains. The synthesis afforded a series of O-alkylated derivatives with typical chalcone skeletons. Compounds 4–10 were reported for the first time. Interestingly, analogue 8 with the new scaffold demonstrated remarkable in vitro growth-inhibitory activities against Saprolegnia strains, displaying greater anti-oomycete potency than the standard drugs used in the assay, namely fluconazole and bronopol. In contrast, a dramatic loss of activity was observed for O-alkylated derivatives 2, 3, 6, and 7. These findings have highlighted the therapeutic potential of the natural compound 1 scaffold to be exploitable as a drug lead with specific activity against various Saprolegnia strains.
Highlights
Aquatic oomycetes cause problems and economic losses in fish hatcheries worldwide
All reagents and solvents were purchased from commercial sources
All reactions were monitored by thin layer chromatography (TLC) on TLC precoated silica gel 60 F254 glass-backed plates (Merck KGaA, Darmstadt, Germany)
Summary
Aquatic oomycetes (water molds) cause problems and economic losses in fish hatcheries worldwide. By different species of the genus Saprolegnia [1], can occur as a secondary infection to bacterial or viral infections [2,3]. Infections had relied on therapeutic use of malachite green for many decades, until malachite green was banned in the European Union in 2002 [4]. Several studies seeking replacements for malachite green have been performed [5,6,7], but no single effective, economical, and safe substitute has yet been found. Bronopol treatment [8] is currently the most used method against saprolegniasis in fish farms. There are growing concerns regarding its use within the industry, since it poses acute
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