Bioactive Metabolites from the Sponge Suberea sp

• Published in: Chemistry & biodiversity 2010-12, Vol.7 (12), p.2880-2887
• Main Authors: Shaker, Kamel H., Zinecker, Heidi, Ghani, Mohamed A., Imhoff, Johannes F., Schneider, Bernd
• Format: Article
• Language: English
• Subjects: Acetamides - chemistry; Acetamides - isolation & purification; Acetamides - toxicity; Animals; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - toxicity; Antimicrobial activity; Cyclic Nucleotide Phosphodiesterases, Type 4 - chemistry; Cyclic Nucleotide Phosphodiesterases, Type 4 - metabolism; Cyclohexanones - chemistry; Cyclohexanones - isolation & purification; Cyclohexanones - toxicity; Cytotoxic activity; dibromo; Humans; Hydrocarbons, Brominated - chemistry; Hydrocarbons, Brominated - metabolism; Hydrocarbons, Brominated - toxicity; Inhibitors; Magnetic Resonance Spectroscopy; Metabolites; Microbial Sensitivity Tests; Molecular Conformation; Phenylacetates - chemistry; Phenylacetates - isolation & purification; Phenylacetates - toxicity; Phosphodiesterase 4 Inhibitors - chemistry; Phosphodiesterase 4 Inhibitors - isolation & purification; Phosphodiesterase 4 Inhibitors - toxicity; Porifera - chemistry; Porifera - metabolism; Sponges; Suberea species; Subereaphenols B and K; Tyrosine; Tyrosine, dibromo
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.200900277

Two new brominated compounds, subereaphenol K (2) and 2‐(3,5‐dibromo‐1‐ethoxy‐4‐oxocyclohexa‐2,5‐dien‐1‐yl)acetamide (3), together with subereaphenol B (methyl 2‐(2,4‐dibromo‐3,6‐dihydroxyphenyl)acetate; 1) with a revised structure, and five dibromotyrosine‐derived metabolites, 4–8, were isolated from the sponge Suberea sp. and characterized by 1D‐ and 2D‐NMR spectroscopic and HR‐MS spectrometric data. Compounds 1, 2, 6, and 8 exhibited various weak or moderate bioactivities, including antimicrobial and cytotoxic activities. Furthermore, compounds 1 and 2 inhibited human recombinant phosphodiesterase 4 (PDE4) with IC50 values of 2 μM, whereas compounds 6 and 8 were less active.