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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.

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