Abstract
Three structurally unique bromopyrrole alkaloids, agelamadins C-E (1-3), were isolated from a marine sponge Agelas sp. Agelamadin C (1) possesses a hybrid structure of oroidin and 3-hydroxykynurenine connected through a dihydro-1,4-oxazine moiety. Agelamadins D (2) and E (3) are a C-9/C-10 diastereomer and a 10-epimer of 1, respectively. The structures of 1-3 were elucidated on the basis of spectroscopic analysis as well as application of a PGME method and a TDDFT ECD calculation. Antimicrobial activity of 1-3 was evaluated.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Agelas / chemistry*
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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-Infective Agents / chemistry
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Anti-Infective Agents / isolation & purification*
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Anti-Infective Agents / pharmacology
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Cryptococcus neoformans / drug effects
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Hydrocarbons, Brominated / chemistry
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Hydrocarbons, Brominated / isolation & purification*
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Hydrocarbons, Brominated / pharmacology
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Kynurenine / analogs & derivatives
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Kynurenine / chemistry
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Microbial Sensitivity Tests
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Pyrroles / chemistry*
Substances
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Alkaloids
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Anti-Infective Agents
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Hydrocarbons, Brominated
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Pyrroles
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agelamadin C
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agelamadin D
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agelamadin E
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3-hydroxykynurenine
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Kynurenine
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oroidin