Quorum Sensing Inhibitory and Antifouling Activities of New Bromotyrosine Metabolites from the Polynesian Sponge Pseudoceratina n. sp.

Florent Tintillier,Claire Hellio,Cécile Debitus,Merrick Ekins,Sylvain Petek,Denis Saulnier,John N A Hooper,Céline Moriou,Ali Al-Mourabit,Marilyne Fauchon

doi:10.3390/md18050272

Abstract

Four new brominated tyrosine metabolites, aplyzanzines C–F (1–4), were isolated from the French Polynesian sponge Pseudoceratina n. sp., along with the two known 2-aminoimidazolic derivatives, purealidin A (5) and 6, previously isolated, respectively, from the sponges Psammaplysilla purpurea and Verongula sp. Their structures were assigned based on the interpretation of their NMR and HRMS data. The compounds exhibited quorum sensing inhibition (QSi) and antifouling activities against several strains of bacteria and microalgae. To our knowledge, the QSi activity of this type of bromotyrosine metabolite is described here for the first time.

Highlights

The unique chemotaxonomy, the tremendous molecular diversity, and the wide array of biological activities have made marine sponges of the order Verongiida a well-studied group
As part of our survey of French Polynesian sponges [47,48,49] for new bioactive natural compounds in both health and sustainable aquaculture fields [50,51,52], we studied the marine sponge Pseudoceratina sp. 2081 and isolated four new tetrabromotyrosine derivatives exhibiting antifouling and quorum sensing inhibition (QSi) properties
A preliminary screening of biological activities performed on the ASE CH2 Cl2 /MeOH (1/1) crude extract of Pseudoceratina sp. 2081 sponge, revealed cytotoxic activity against the KB tumor cell lines (100% at 10 μg/mL)

Summary

Introduction

The unique chemotaxonomy, the tremendous molecular diversity, and the wide array of biological activities have made marine sponges of the order Verongiida a well-studied group. A recent study showed that the bacterium Pseudovibrio denitrificans Ab134, isolated from the sponge Arenosclera brasiliensis (order Haplosclerida), has the capacity to produce bromotyrosine derivatives [7]. Setting aside misidentification of organisms and cross-contamination, this reminds us to remain cautious about the use of secondary metabolites for sponge taxonomy [8] These bromotyrosine derivatives have very diverse structures, from the simplest such as subereaphenols [9], with two bromophenolic units such as psammaplysenes [10,11,12], amomoians [10,13,14], and aplyzanzines [14,15], to the most complex polycyclic such as archerines [16] or fistularins [17].

Methods

Results

Conclusion