Abstract
Two new polycyclic guanidine alkaloids, crambescidin 826 (1) and dehydrocrambine A (2), and the known compounds crambescidin 800 (3) and fromiamycalin (4) were isolated from the marine sponge Monanchora sp. The structures of 1 and 2 were elucidated by 2D NMR and mass spectrometry, and relative stereochemistry was established by analysis of coupling constants and ROESY spectra. The pentacyclic guanidine alkaloids 1, 3, and 4 inhibit HIV-1 envelope-mediated fusion in vitro with IC(50)'s of 1-3 microM, while compound 2, a tricyclic guanidine alkaloid, showed weaker inhibition, with an IC(50) of approximately 35 microM.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkaloids* / chemistry
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Alkaloids* / isolation & purification
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Alkaloids* / pharmacology
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Animals
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Anti-HIV Agents* / chemistry
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Anti-HIV Agents* / isolation & purification
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Anti-HIV Agents* / pharmacology
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Guanidines* / chemistry
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Guanidines* / isolation & purification
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Guanidines* / pharmacology
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Inhibitory Concentration 50
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Palau
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Porifera / chemistry*
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Spiro Compounds* / chemistry
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Spiro Compounds* / isolation & purification
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Spiro Compounds* / pharmacology
Substances
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Alkaloids
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Anti-HIV Agents
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Guanidines
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Spiro Compounds
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crambescidin 826
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dehydrocrambine A