Discorhabdins from the Korean Marine Sponge Sceptrella sp

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2010-02, Vol.73 (2), p.258-262
• Main Authors: Jeon, Ju-eun, Na, Zeyei, Jung, Misong, Lee, Hyi-Seung, Sim, Chung J, Nahm, Keepyung, Oh, Ki-Bong, Shin, Jongheon
• Format: Article
• Language: English
• Subjects: Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Aminoacyltransferases - antagonists & inhibitors; Animals; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Bacillus subtilis - drug effects; Bacterial Proteins - antagonists & inhibitors; Biological and medical sciences; Cysteine Endopeptidases; Drug Screening Assays, Antitumor; Escherichia coli - drug effects; General pharmacology; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - isolation & purification; Heterocyclic Compounds, 4 or More Rings - pharmacology; Humans; K562 Cells; Marine; Marine Biology; Medical sciences; Micrococcus luteus - drug effects; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Porifera - chemistry; Proteus vulgaris - drug effects; Quinones - chemistry; Quinones - isolation & purification; Quinones - pharmacology; Salmonella typhimurium - drug effects; Staphylococcus aureus - drug effects; Stereoisomerism
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np9005629

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.