Urupocidin A: A New, Inducing iNOS Expression Bicyclic Guanidine Alkaloid from the Marine Sponge Monanchora pulchra

Urupocidin A: A New, Inducing iNOS Expression Bicyclic Guanidine Alkaloid from the Marine Sponge Monanchora pulchra

Urupocidins A and B (1 and 2), bisguanidine alkaloids with an unprecedented skeleton system, derived from polyketide precursors and containing an unusual N-alkyl-N-hydroxyguanidine moiety, have been isolated from the sponge Monanhora pulchra. The structures of 1 and 2, including absolute configurati...

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Veröffentlicht in:Organic letters 2014-08, Vol.16 (16), p.4292-4295
Hauptverfasser: Makarieva, Tatyana N, Ogurtsova, Ekaterina K, Denisenko, Vladimir A, Dmitrenok, Pavel S, Tabakmakher, Ksenya M, Guzii, Alla G, Pislyagin, Evgeny A, Es’kov, Andrey A, Kozhemyako, Valery B, Aminin, Dmitry L, Wang, Yun-Ming, Stonik, Valentin A
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemistry
Alkaloids - pharmacology
Animals
Guanidines - chemistry
Guanidines - pharmacology
Inhibitory Concentration 50
Marine Biology
Mice
Molecular Structure
Nitric Oxide
Nitric Oxide Synthase Type II - drug effects
Nuclear Magnetic Resonance, Biomolecular
Porifera - chemistry
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Zusammenfassung:Urupocidins A and B (1 and 2), bisguanidine alkaloids with an unprecedented skeleton system, derived from polyketide precursors and containing an unusual N-alkyl-N-hydroxyguanidine moiety, have been isolated from the sponge Monanhora pulchra. The structures of 1 and 2, including absolute configuration, were established using the detailed analysis of 1D and 2D NMR, CD, and mass spectra as well as chemical transformations. Compound 1 increases nitric oxide production in murine macrophages via inducing iNOS expression.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502013f