Tausalarin C: A New Bioactive Marine Sponge-Derived Nitrogenous Bismacrolide

A novel nitrogenous bismacrolide, designated tausalarin C (1), was isolated from the Madagascar sponge Fascaplysinopsis sp. The structure of the compound was elucidated by interpretation of MS and 1D and 2D NMR spectra. It is suggested that tausalarin C is assembled from salarin A (2) and pretaumyci...

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Bibliographic Details
Published in:Organic letters 2009-08, Vol.11 (16), p.3538-3541
Main Authors: Bishara, Ashgan, Rudi, Amira, Goldberg, Israel, Aknin, Maurice, Neumann, Drorit, Ben-Califa, Nathalie, Kashman, Yoel
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Chemical Sciences
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Humans
K562 Cells
Macrolides - chemistry
Macrolides - isolation & purification
Macrolides - metabolism
Macrolides - pharmacology
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Porifera - chemistry
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Summary:A novel nitrogenous bismacrolide, designated tausalarin C (1), was isolated from the Madagascar sponge Fascaplysinopsis sp. The structure of the compound was elucidated by interpretation of MS and 1D and 2D NMR spectra. It is suggested that tausalarin C is assembled from salarin A (2) and pretaumycin A. The relative configuration of the chiral centers of salarin A was determined by X-ray diffraction. Tausalarin C was found to inhibit proliferation of K562 leukemia cells. A possible biogenesis is discussed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9011019