Sponge-Inspired Dibromohemibastadin Prevents and Disrupts Bacterial Biofilms without Toxicity

Abstract

Since the banning of several families of compounds in antifouling (AF) coatings, the search for environmentally friendly AF compounds has intensified. Natural sources of AF compounds have been identified in marine organisms and can be used to create analogues in laboratory. In a previous study, we identified that dibromohemibastadin-1 (DBHB) is a promising AF molecule, leading to the inhibition of the activity of phenoloxidase, an enzyme involved in the attachment of mussels to surfaces. This paper describes the activity of the DBHB on biofilm formation and its detachment and on bacterial adhesion and communication: quorum sensing. DBHB has an anti-biofilm activity without affecting adhesion of marine and terrestrial bacteria at a dose of 10 µM. Moreover, DBHB activity on quorum sensing (QS) is demonstrated at doses of 8 and 16 µM. The activity of DBHB on QS is compared to kojic acid, a quorum sensing inhibitor already described. This compound is a promising environmentally friendly molecule potentially useful for the inhibition of microfouling.

Design and Biological Evaluation of Antifouling Dihydrostilbene Oxime Hybrids

“…A considerable number of effective natural marine antifoulants, for example, ianthelline ( 3 ), psammaplin A, and debromohemibastadin-1 ( 4 ), contain the oxime functionality (Hanssen et al 2014 ; Ortlepp et al 2007 ; Le Norcy et al 2017a , b ) in a homobenzylic position. The planar oxime provides structural rigidity to the molecules, decreasing rotational freedom, and studies by Proksch and coworkers have established the crucial role of the oxime for the AF activity of the bastadin family of compounds (Bayer et al 2011 ; Ortlepp et al 2007 ).…”

Marine Organisms from the Yucatan Peninsula (Mexico) as a Potential Natural Source of Antibacterial Compounds

“…Sponges of the order Haplosclerida, to which Amphimedon compressa belongs, constitute well-known sources of alkylpyridine and alkylpiperidine alkaloids [ 40 , 56 ]. More specifically, halitoxins and amphitoxins are cyclic alkylpyridine oligomers of challenging separation and structural characterization due to their polycharged structures and high molecular weights [ 51 , 52 , 53 ].…”

“…Recently, dibromohemibastadin-1, which showed a potent inhibition of biofilm formation of Paracoccus sp. 4M6 and P. aeruginosa PAO1 (at 10 µM) and quorum sensing inhibition of E. coli pSB401 (at 8-16 µM), was isolated from the same species [40]. (-)-Aeroplysinin-1 and ianthelline were reported from I. ardis, both displaying antibacterial activity, the latter active against S. aureus [41,42].…”

“…Subfraction R4H2 displayed higher antibacterial activity than fraction R4, yielding a MIC value of 2-4 mg/L for different strains of A. baumannii, K. pneumoniae, and P. aeruginosa and a MIC value of 1 mg/L for both strains of S. aureus (Tables 2 and 3). Sponges of the order Haplosclerida, to which Amphimedon compressa belongs, constitute well-known sources of alkylpyridine and alkylpiperidine alkaloids [40,56]. More specifically, halitoxins and amphitoxins are cyclic alkylpyridine oligomers of challenging separation and structural characterization due to their polycharged structures and high molecular weights [51][52][53].…”

Naturally Drug-Loaded Chitin: Isolation and Applications

“…Currently, our strategy regarding the ianthellid sponges is focused on development of methods for simultaneous extraction of both naturally pre-designed chitin (as “ready-to-use” scaffolds) and biologically active bromotyrosines which are recognized as potential antibiotic, antitumor (for a review, see References [18,19]), and marine antifouling [20,21] substances. The pharmacological potential of these marine demosponges as producers of bromotyrosine-related bastadins was very positively approved [22,23,24,25,26,27].…”