ABSTRACT
Six new compounds, omaezol, intricatriol, hachijojimallenes A and B, debromoaplysinal, and 11,12-dihydro-3-hydroxyretinol have been isolated from four collections of Laurencia sp. These structures were determined by MS and NMR analyses. Their antifouling activities were evaluated together with eight previously known compounds isolated from the same samples. In particular, omaezol and hachijojimallene A showed potent activities (EC50 = 0.15-0.23 µg/mL) against larvae of the barnacle Amphibalanus amphitrite.
Subject(s)
Biofouling/prevention & control , Diterpenes/pharmacology , Larva/drug effects , Laurencia/chemistry , Omeprazole/isolation & purification , Omeprazole/pharmacology , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Thoracica/drug effects , Animals , Diterpenes/chemistry , Diterpenes/isolation & purification , Japan , Marine Biology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Omeprazole/chemistry , Sesquiterpenes/chemistry , Vitamin A/analogs & derivativesABSTRACT
Natural antifouling products have been the subject of considerable attention. We screened marine algae for antifouling activity and discovered omaezallenes, the new bromoallene-containing natural products isolated from the red alga Laurenciaâ sp. Described is the isolation, structure elucidation, and total syntheses of omaezallenes. The relative and absolute configurations of natural omaezallenes were unambiguously established through total synthesis. The antifouling activities and ecotoxicity of omaezallenes were also evaluated.
