Structural Assignment of Poecillastrins B and C, Macrolide Lactams from the Deep-Water Caribbean Sponge Poecillastra Species

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2007-03, Vol.70 (3), p.428-431
• Main Authors: Takada, Kentaro, Choi, Byoung W, Rashid, Mohammad A, Gamble, William R, Cardellina, John H, Van, Que N, Lloyd, John R, McMahon, James B, Gustafson, Kirk R
• Format: Article
• Language: English
• Subjects: Animals; anticarcinogenic activity; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Bahamas; Biological and medical sciences; chemical analysis; chemical structure; chondropsin; cultured cells; cytotoxicity; Drug Screening Assays, Antitumor; General pharmacology; Humans; lactams; Lactams - chemistry; Lactams - isolation & purification; Lactams - pharmacology; macrolides; Macrolides - chemistry; Macrolides - isolation & purification; Macrolides - pharmacology; Medical sciences; Melanoma; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Poecillastra; poecillastrin; Porifera; Porifera - chemistry; spectral analysis; Tumor Cells, Cultured
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0604984

Two new chondropsin-type macrolide lactams, poecillastrins B (1) and C (2), were isolated from aqueous extracts of the marine sponge Poecillastra sp. These trace metabolites were isolated in low yield (400−600 μg), and their structures were determined primarily by analysis of NMR data acquired using a cyrogenically cooled probe. High-quality 1D and 2D NMR data sets allowed complete assignment of the spectroscopic data and defined the new structures as 35-membered ring analogues of poecillastrin A (3). Compounds 1 and 2 showed potent cytotoxic activity against a human melanoma tumor cell line (LOX) with an IC50 value of less than 1 μg/mL.