Populations of the sponge Dysidea (Lamellodysidea) herbacea, which host the cyanobacterium Oscillatoria spongeliae, vary in their production of polychlorinated peptides. Peptide natural products previously isolated from D. herbacea are often halogenated and include dysidin, dysidinin, and a series of chlorinated diketopiperazines. Strikingly, the distinctive leucine-derived trichloromethyl signature of these compounds is shared only with metabolites of the marine cyanobacterium Lyngbya majuscula, and includes such compounds as barbamide and nordysidinin. Genetic information available for the barbamide biosynthetic gene cluster was used to successfully polymerase chain reaction (PCR) amplify a barB1 homolog (dysB1) from D. herbacea samples collected in Papua New Guinea. Catalyzed reporter deposition fluorescence in situ hybridization (CARD-FISH) analysis showed that dysB1 oligonucleotide probes hybridized to sequences in the filamentous cyanobacterial symbiont O. spongeliae. Consistent with this finding, a D. herbacea/O. spongeliae collection devoid of the polychlorinated peptides did not contain the barB1 homologs. |
