Antifouling Activity of Bromotyrosine-Derived Sponge Metabolites and Synthetic Analogues

Ortlepp, Sofia; Sjögren, Martin; Dahlström, Mia; Weber, Hendrik; Ebel, Rainer; Edrada, Ru Angelie; Thoms, Carsten; Schupp, Peter J.; Bohlin, Lars; Proksch, Peter

doi:10.1007/s10126-007-9029-x

Cited by 76 publications

(99 citation statements)

References 50 publications

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“…In the latter study, found 2 exceptions to the general rule: the Red Sea sponge Axinella carteri and a Caribbean Stylissa species, both belonging to the family Axinellidae. These 2 species are known to contain bromopyrrole compounds including feeding-deterrent ones (Fedoreyev et al 1986, Assmann et al 2001b, Assmann & Köck 2002, Ortlepp et al 2007, and thus might rely on chemical anti-predator defense alone. Ferguson & Davis (2008) indicated the possibility that spicules of a size smaller than 100 µm deter the generalist sea urchin Centrostephanus rodgersii.…”

Section: Discussionmentioning

confidence: 99%

Chemical defense against predators and bacterial fouling in the Mediterranean sponges Axinella polypoides and A. verrucosa

Haber¹,

Carbone²,

Mollo³

et al. 2011

Mar. Ecol. Prog. Ser.

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The diverse natural products found within sponges mediate many of their ecological interactions, including predator feeding deterrence and defense against fouling. Pyrrole-imidazole compounds, often involved in such ecological interactions, are exclusively found in marine sponges, mainly from the genera Axinella and Agelas. Employing field and laboratory assays, we studied the chemical defense of 2 co-occurring Mediterranean sponges, Axinella polypoides and A. verrucosa, collected from the Gulf of Naples, Italy, against microbial fouling, as well as their feeding deterrence against the generalist shrimp Palaemon elegans. These assays revealed no activity in the extracts of A. polypoides, while the n-butanol part of the A. verrucosa extract showed activity in all assays at natural concentrations. This fraction of the extract contains the bromopyrrole hymenidin, and our assays revealed antibacterial and feeding deterrence activity for this pure compound. 1 H nuclear magnetic resonance quantification confirmed the presence of hymenidin and debromo-carteramine A, another previously isolated antibacterial compound, at ecologically relevant concentrations in the n-butanol part of the A. verrucosa extract. Our results indicate different antimicrobial and feeding deterrence defense strategies in the 2 examined sympatric sponge species, and multiple defensive roles of hymenidin in the defense of A. verrucosa, similar to those of other bromopyrroles isolated from taxonomically related Caribbean sponges. KEY WORDS: Bromopyrroles · Antifouling · Feeding deterrence · Chemical ecology · PoriferaResale or republication not permitted without written consent of the publisher

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Section: Discussionmentioning

confidence: 99%

Chemical defense against predators and bacterial fouling in the Mediterranean sponges Axinella polypoides and A. verrucosa

Haber¹,

Carbone²,

Mollo³

et al. 2011

Mar. Ecol. Prog. Ser.

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“…This finding implies that within a compound library, different mode of actions may be operating. 48 bastadin-9 (IC50 = 1.0 µM) 49 and synoxazolidinone C (IC50 = 2 µM). 29 The compounds also share similar structural features and antifouling activities with the natural antifouling phenyl ethers recently reported by Wang and co-workers.…”

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confidence: 99%

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

Moodie¹,

Trépos

Cervin

et al. 2017

J. Nat. Prod.

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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.

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“…Bromotyrosine derivatives, polybrominated diphenyl ethers, subergorgic acid and so on were all isolated from sponges, which were promising sources of antifoulants. [33][34][35] Li et al [36] reported that 49 secondary metabolites, including diterpenoids, steroids and polyketides, were isolated from soft corals, gorgonians, brown algae and fungi. Twenty of the compounds were found to inhibit significantly the settlement of barnacle larvae at a concentration of 25 mg/L.…”

Section: Discussionmentioning

confidence: 99%

Comparative effects of indole derivatives as antifouling agents on the growth of two marine diatom species

Yang

Sun

Liu

et al. 2015

Chemistry and Ecology

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Antifouling agents, used to prevent biofouling, need to be assessed for their impacts on marine organisms and environment before the application. Diatoms are one of the main components of fouling biofilms, which play important roles in the formation of biofouling. Particularly, diatoms are also the important ingredients of primary production and present interest as ecotoxicological models in marine environment. In this study, two benthic diatoms Nitzschia closterium f. minutissima and Navicula climacospheniae, widely distributed in fouling biofilm, were used as models for screening the activities of potential antifoulants. Nine indole derivatives were tested and CuSO 4 was used as a reference. Indole derivatives showed significant anti-algal activities and the EC 50 values of most indole derivatives were lower than that of CuSO 4 . Halogen substituent enhanced the anti-algal activities of compounds, and the most efficient compounds for N. closterium f. minutissima were gramine and 7-chloroindole with the EC 50 values of 1.94 and 2.1 mg/L, while for N. climacospheniae, 7-chloroindole and 6-bromoindole were the most efficient and the EC 50 values were 3.91 and 4.25 mg/L, respectively. In conclusion, indole derivatives would be one of the promising candidates as antifoulants and our results strengthened the need to perform antifouling activity assays and environment-friendly evaluations.

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Antifouling Activity of Bromotyrosine-Derived Sponge Metabolites and Synthetic Analogues

Cited by 76 publications

References 50 publications

Chemical defense against predators and bacterial fouling in the Mediterranean sponges Axinella polypoides and A. verrucosa

Chemical defense against predators and bacterial fouling in the Mediterranean sponges Axinella polypoides and A. verrucosa

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

Comparative effects of indole derivatives as antifouling agents on the growth of two marine diatom species

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