The current study reports the first
comprehensive evaluation of
a class of allelopathic terrestrial natural products as antifoulants
in a marine setting. To investigate the antifouling potential of the
natural dihydrostilbene scaffold, a library of 22 synthetic dihydrostilbenes
with varying substitution patterns, many of which occur naturally
in terrestrial plants, were prepared and assessed for their antifouling
capacity. The compounds were evaluated in an extensive screen against
16 fouling marine organisms. The dihydrostilbene scaffold was shown
to possess powerful general antifouling effects against both marine
microfoulers and macrofoulers with inhibitory activities at low concentrations.
The species of microalgae examined displayed a particular sensitivity
toward the evaluated compounds at low ng/mL concentrations. It was
shown that several of the natural and synthetic compounds exerted
their repelling activities via nontoxic and reversible mechanisms.
The activities of the most active compounds such as 3,5-dimethoxybibenzyl
(5), 3,4-dimethoxybibenzyl (9), and 3-hydroxy-3′,4,5′-trimethoxybibenzyl
(20) were comparable to the commercial antifouling booster
biocide Sea-nine, which was employed as a positive control. The investigation
of terrestrial allelopathic natural products to counter marine fouling
represents a novel strategy for the design of “green”
antifouling technologies, and these compounds offer a potential alternative
to traditional biocidal antifoulants.