Inhibition of Biofilm Formation by Modified Oxylipins from the Shipworm Symbiont Teredinibacter turnerae

Abstract

The bioactivity-guided purification of the culture broth of the shipworm endosymbiont Teredinibacter turnerae strain 991H.S.0a.06 yielded a new fatty acid, turneroic acid (1), and two previously described oxylipins (2–3). Turneroic acid (1) is an 18-carbon fatty acid decorated by a hydroxy group and an epoxide ring. Compounds 1–3 inhibited bacterial biofilm formation in Staphylococcus epidermidis, while only 3 showed antimicrobial activity against planktonic S. epidermidis. Comparison of the bioactivity of 1–3 with structurally related compounds indicated the importance of the epoxide moiety for selective and potent biofilm inhibition.

Marine natural products

“…79 A culture of Teredinibacter turnerae yielded turneroic acid 250, an 18-carbon fatty acid decorated with hydroxy and epoxide moieties, that inhibited biolm formation. 80 The genus Verrucosispora was the source of new aminofurans, proximicins F 251 and G 252 and diproximicin A 253 that were obtained via overexpression of PPtase genes, 81 a siderophore named FW0622 254, 82 an abyssomicin polyketide 255, 83 and verrucosamide 256, a cytotoxic 1,4-thiazepane-containing thiodepsipeptide. 84 Genomic-metabolomic proling of Vibrio spartinae identied this proteobacteria as a producer of isoheptylprodigiosin 257, a new branched sidechain prodigiosin, 85 while chemical investigations of a Vibrio sp.…”

“…A culture of Teredinibacter turnerae yielded turneroic acid 250 , an 18-carbon fatty acid decorated with hydroxy and epoxide moieties, that inhibited biofilm formation. 80…”

Modified oxylipins as inhibitors of biofilm formation in Staphylococcus epidermidis

“…Several marine-derived compounds were characterized to produce anti-biofilm properties with varying target domains, such as quorum sensing (QS)-inhibitor psammaplin A ( Oluwabusola et al, 2022 ), EPS-disruptor cyclic dipeptide ( L -Leucyl- L -propyl) ( Gowrishankar et al, 2014 ), pre-formed biofilm suppressor butenolide ( Yin et al, 2019 ), and bacterial aggregation downregulator rodriguesine A ( Lima et al, 2014 ). Three modified fatty acids were previously purified from the shipworm endosymbiont Teredinibacter turnerae 991H.S.0a.06 ( Lacerna et al, 2020 ). Turneroic acid, a new modified oxylipin characterized by an epoxide moiety and a hydroxy group, inhibited biofilm formation in S. epidermidis RP26A ( Lacerna et al, 2020 ).…”

“…Three modified fatty acids were previously purified from the shipworm endosymbiont Teredinibacter turnerae 991H.S.0a.06 ( Lacerna et al, 2020 ). Turneroic acid, a new modified oxylipin characterized by an epoxide moiety and a hydroxy group, inhibited biofilm formation in S. epidermidis RP26A ( Lacerna et al, 2020 ). Preliminary structure-activity relationship (SAR) showed that trans -12,13-epoxyoctadecanoic acid ( 1 ) has a high selectivity index for anti-biofilm activity against S. epidermidis with no antiproliferative effects against MDCK NBL-2 cell line ( Lacerna et al, 2020 ).…”

“…Turneroic acid, a new modified oxylipin characterized by an epoxide moiety and a hydroxy group, inhibited biofilm formation in S. epidermidis RP26A ( Lacerna et al, 2020 ). Preliminary structure-activity relationship (SAR) showed that trans -12,13-epoxyoctadecanoic acid ( 1 ) has a high selectivity index for anti-biofilm activity against S. epidermidis with no antiproliferative effects against MDCK NBL-2 cell line ( Lacerna et al, 2020 ). SAR showed the importance of the epoxide moiety in selective biofilm inhibition against Staphylococci ( Lacerna et al, 2020 ).…”