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Synthesis and Antifouling Activity Evaluation of Analogs of Bromosphaerol, a Brominated Diterpene Isolated from the Red Alga Sphaerococcus coronopifolius

Authors :
Kyriakos C. Prousis
Stefanos Kikionis
Efstathia Ioannou
Silvia Morgana
Marco Faimali
Veronica Piazza
Theodora Calogeropoulou
Vassilios Roussis
Source :
Marine Drugs, Marine Drugs, Vol 20, Iss 7, p 7 (2022), Marine Drugs; Volume 20; Issue 1; Pages: 7
Publication Year :
2021
Publisher :
MDPI, 2021.

Abstract

Marine biofouling is an epibiotic biological process that affects almost any kind of submerged surface, causing globally significant economic problems mainly for the shipping industry and aquaculture companies, and its prevention so far has been associated with adverse environmental effects for non-target organisms. Previously, we have identified bromosphaerol (1), a brominated diterpene isolated from the red alga Sphaerococcus coronopifolius, as a promising agent with significant antifouling activity, exerting strong anti-settlement activity against larvae of Amphibalanus (Balanus) amphitrite and very low toxicity. The significant antifouling activity and low toxicity of bromosphaerol (1) motivated us to explore its chemistry, aiming to optimize its antifouling potential through the preparation of a number of analogs. Following different synthetic routes, we successfully synthesized 15 structural analogs (2–16) of bromosphaerol (1), decorated with different functional groups. The anti-settlement activity (EC50) and the degree of toxicity (LC50) of the bromosphaerol derivatives were evaluated using cyprids and nauplii of the cirriped crustacean A. amphitrite as a model organism. Derivatives 2, 4, and 6–16 showed diverse levels of antifouling activity. Among them, compounds 9 and 13 can be considered as well-performing antifoulants, exerting their activity through a non-toxic mechanism.

Details

Language :
English
ISSN :
16603397
Volume :
20
Issue :
1
Database :
OpenAIRE
Journal :
Marine Drugs
Accession number :
edsair.doi.dedup.....456d8cbf244eef06c1c81db71b2182ed