Aurilides B and C, Cancer Cell Toxins from a Papua New Guinea Collection of the Marine Cyanobacterium Lyngbya majuscula

Cytotoxicity-guided fractionation of a strain of the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea led to the isolation of aurilides B (1) and C (2). The planar structures of 1 and 2 were established by spectroscopic analysis, including HR-FABMS, 1D (1)H and (13)C NMR, and...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-04, Vol.69 (4), p.572-575
Main Authors: HAN, Bingnan, GROSS, Harald, GOEGER, Douglas E., MOOBERRY, Susan L., GERWICK, William H.
Format: Article
Language:English
Subjects:
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Applied microbiology
Biological and medical sciences
Chemotherapic agents
Cyanobacteria
Cyanophyta
Drug Screening Assays, Antitumor
Fundamental and applied biological sciences. Psychology
Lyngbya majuscula
Lyngbya Toxins - chemistry
Lyngbya Toxins - isolation & purification
Lyngbya Toxins - pharmacology
Marine
Marine Toxins - chemistry
Marine Toxins - isolation & purification
Marine Toxins - pharmacology
Microbiology
Molecular Structure
Papua New Guinea
Peptides, Cyclic - chemistry
Peptides, Cyclic - isolation & purification
Peptides, Cyclic - pharmacology
Tumor Cells, Cultured
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Summary:Cytotoxicity-guided fractionation of a strain of the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea led to the isolation of aurilides B (1) and C (2). The planar structures of 1 and 2 were established by spectroscopic analysis, including HR-FABMS, 1D (1)H and (13)C NMR, and 2D COSY, HSQC, HSQC-TOCSY, and HMBC spectra. The absolute configuration was determined by spectroscopic analysis and chiral HPLC analysis of acid hydrolysates of 1 and 2. Both aurilides B and C showed in vitro cytotoxicity toward NCI-H460 human lung tumor and the neuro-2a mouse neuroblastoma cell lines, with LC(50) values between 0.01 and 0.13 microM. Aurilide B (1) was evaluated in the NCI 60 cell line panel and found to exhibit a high level of cytotoxicity (the mean panel GI(50) concentration was less than 10 nM) and to be particularly active against leukemia, renal, and prostate cancer cell lines.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0503911