dd-diketopiperazines: antibiotics active against Vibrio anguillarum isolated from marine bacteria associated with cultures of Pecten maximus.
Bacterial strains CF-20 (CECT5719) and C-148 (CECT5718), isolated from cultures of larvae of molluscs, are shown to produce substances 1-5 with strong antibiotic activity against Vibrio anguillarum (MIC: 0.03-0.07 mug/mL) and identified as the dd-diketopiperazines cyclo(d)-Pro-(d)-Phe (1), cyclo(d)-Pro-(d)-Leu (2), cyclo(d)-Pro-(d)-Val (3), cyclo(d)-Pro-(d)-Ile (4), and cyclo-trans-4-OH-(d)-Pro-(d)-Phe (5). Comparison with other stereoisomers indicates that inhibition of V. anguillarum is associated with the presence of at least one d-amino acid in the diketopiperazine system. This is the first time a series of dd-diketopiperazines has been isolated from a single natural source and their inhibitory activity against V. anguillarum described.
Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago, 15782 Santiago de Compostela, Spain.
Faouzi
F
Fdhila
Victoriano
V
Vázquez
José Luis
JL
Sánchez
Ricardo
R
Riguera
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001419:Bacteria / Q000737:chemistry*; D008974:Mollusca; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010879:Piperazines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D014733:Vibrio / Q000187:drug effects*
D000900:Anti-Bacterial Agents; D010456:Peptides, Cyclic; D010879:Piperazines