Abstract
By combining the recently reported repelling natural dihydrostilbene scaffold with an oxime moiety found in many marine antifoulants, a library of nine antifouling hybrid compounds was developed and biologically evaluated. The prepared compounds were shown to display a low antifouling effect against marine bacteria but a high potency against the attachment and growth of microalgae down to MIC values of 0.01 μg/mL for the most potent hybrid. The mode of action can be characterized as repelling via a reversible non-toxic biostatic mechanism. Barnacle cyprid larval settlement was also inhibited at low μg/mL concentrations with low levels or no toxicity observed. Several of the prepared compounds performed better than many reported antifouling marine natural products. While several of the prepared compounds are highly active as antifoulants, no apparent synergy is observed by incorporating the oxime functionality into the dihydrostilbene scaffold. This observation is discussed in light of recently reported literature data on related marine natural antifoulants and antifouling hybrids as a potentially general strategy for generation of improved antifoulants.
Highlights
Marine biofouling, the rapid colonization and growth of organisms on marine surfaces, commonly occurs on ships, buoys, cooling systems, and aquaculture equipment
Intrigued whether the allelopathic activity of terrestrially derived natural products can be used to yield effective antifoulants in a marine setting, we recently investigated the AF activity of the allelopathic dihydrostilbene compound batatasin-III (1) (Fig. 1) (Moodie et al 2017a, b)
The initial adsorption of organic molecules to a surface instigates a rapid settlement of microfouling organisms
Summary
In Nature, numerous strategies have been developed by a diverse range of organisms to counteract the risk of being colonized or overgrown. Marine natural products represent a valuable resource in the search for new AF compounds (Qian et al 2015; Fusetani 2011). In addition to producing an arsenal of AF compounds, marine and terrestrial plants use allelopathic phytochemicals to suppress competitive species. These allelochemicals have the ability to prevent the establishment of competitive plant species and represent important defensive chemical agents for many plants and algae (Nilsson and Wardle 2005)
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