ABSTRACT
Two new pyrroloiminoquinone alkaloids of the discorhabdin class, along with 12 compounds including one previously described synthetic derivative of the same and related skeletal classes, were isolated from the sponge Sceptrella sp., collected from Gageodo, Korea. The structures of these new compounds, designated as (-)-3-dihydrodiscorhabdin D (11) and (-)-discorhabdin Z (12), were determined by combined spectroscopic analyses. Compound 12 possesses an unusual hemiaminal group among the discorhabdin alkaloids. These compounds exhibited moderate to significant cytotoxicity, antibacterial activity, and inhibitory activity against sortase A.
Subject(s)
Alkaloids/isolation & purification , Alkaloids/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Heterocyclic Compounds, 4 or More Rings/isolation & purification , Heterocyclic Compounds, 4 or More Rings/pharmacology , Porifera/chemistry , Quinones/isolation & purification , Quinones/pharmacology , Alkaloids/chemistry , Aminoacyltransferases/antagonists & inhibitors , Animals , Anti-Bacterial Agents/chemistry , Antineoplastic Agents/chemistry , Bacillus subtilis/drug effects , Bacterial Proteins/antagonists & inhibitors , Cysteine Endopeptidases , Drug Screening Assays, Antitumor , Escherichia coli/drug effects , Heterocyclic Compounds, 4 or More Rings/chemistry , Humans , K562 Cells , Marine Biology , Micrococcus luteus/drug effects , Nuclear Magnetic Resonance, Biomolecular , Proteus vulgaris/drug effects , Quinones/chemistry , Salmonella typhimurium/drug effects , Staphylococcus aureus/drug effects , StereoisomerismABSTRACT
Eleven new meroditerpenoids (7-11, 14-17, 19, 20) and nine known compounds (1-6, 12, 13, 18) were isolated from the brown alga Sargassum siliquastrum. Combined chemical and spectroscopic analyses revealed a common tetraprenyl hydroquinone structure; these compounds belonged to the nahocol, isonahocol, and sargahydroquinoic acid classes. The dihydroquinone moiety of 20 was unique and unprecedented in a brown alga. Stereochemical assignments were made for several of the known compounds based on their chemical reactivity. These compounds exhibited moderate to significant radical-scavenging activity as well as weak inhibitory activities against sortase A and isocitrate lyase.