Monanchocidin: A New Apoptosis-Inducing Polycyclic Guanidine Alkaloid from the Marine Sponge Monanchora pulchra

Monanchocidin (1), a guanidine alkaloid with an unprecedented skeleton system derived from a polyketide precursor, (ω-3)-hydroxy fatty acid, and containing a 2-aminoethyl- and 3-aminopropyl-substituted morpholine hemiketal ring, has been isolated from the sponge Monanhora pulchra. The structure of 1...

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Bibliographic Details
Published in:Organic letters 2010-10, Vol.12 (19), p.4292-4295
Main Authors: Guzii, Alla G, Makarieva, Tatyana N, Denisenko, Vladimir A, Dmitrenok, Pavel S, Kuzmich, Alexandra S, Dyshlovoy, Sergey A, Krasokhin, Vladimir B, Stonik, Valentin A
Format: Article
Language:English
Subjects:
Animals
Apoptosis - drug effects
Cell Line
Guanidine - analogs & derivatives
Guanidine - chemistry
Guanidine - pharmacology
Humans
Mice
Molecular Structure
Oxidation-Reduction
Porifera - chemistry
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Summary:Monanchocidin (1), a guanidine alkaloid with an unprecedented skeleton system derived from a polyketide precursor, (ω-3)-hydroxy fatty acid, and containing a 2-aminoethyl- and 3-aminopropyl-substituted morpholine hemiketal ring, has been isolated from the sponge Monanhora pulchra. The structure of 1 was assigned on the basis of detailed analysis of 1D and 2D NMR spectra, mass spectrometry, and results of chemical transformations. Compound 1 shows pro-apoptotic and cytoxic activities.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101716x