Abstract
Three new indolediketopiperazine peroxides, namely, 24-hydroxyverruculogen (1), 26-hydroxyverruculogen (2), and 13-O-prenyl-26-hydroxyverruculogen (3), along with four known homologues (4-7), were isolated and identified from the culture extract of the marine sediment-derived fungus Penicillium brefeldianum SD-273. Their structures were determined based on the extensive spectroscopic analysis and compound 1 was confirmed by X-ray crystallographic analysis. The absolute configuration of compounds 1-3 was determined using chiral HPLC analysis of their acidic hydrolysates. Each of the isolated compounds was evaluated for antibacterial and cytotoxic activity as well as brine shrimp (Artemia salina) lethality.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / pharmacology
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology
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Artemia / drug effects
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Cell Line, Tumor
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Chromatography, High Pressure Liquid
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Crystallography, X-Ray
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Diketopiperazines / chemistry
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Diketopiperazines / isolation & purification
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Diketopiperazines / pharmacology*
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Geologic Sediments / microbiology
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Humans
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Indoles / chemistry
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Indoles / isolation & purification
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Indoles / pharmacology*
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Penicillium / metabolism*
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Peroxides / chemistry
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Peroxides / isolation & purification
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Peroxides / pharmacology*
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Prenylation
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Spectrum Analysis
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Toxicity Tests / methods
Substances
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Anti-Bacterial Agents
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Antineoplastic Agents
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Diketopiperazines
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Indoles
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Peroxides