Abstract
Eight novel bioactive metabolites were isolated from submerged cultures of the ascomycete Lachnum papyraceum (Karst.) Karst, when CaBr2 was added to the cultures after the onset of secondary metabolism. Four of these metabolites (16 to 19) are bromo analogues of mycorrhizin A and lachnumon, while (l'Z)-dechloromycorrhizin A (12) and the papyracons A (13), B (14), and C (15) are non-halogenated compounds structurally related to the mycorrhizins. All compounds exhibited antimicrobial, cytotoxic, nematicidal and phytotoxic activities. The brominated mycorrhizins and lachnumons were found to be slightly less active than the chlorine-containing compounds. All mycorrhizin derivatives were mutagenic in the Ames test, suggesting DNA-alkylating properties.
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 / pharmacology*
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Antinematodal Agents / chemistry
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Antinematodal Agents / pharmacology*
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Ascomycota / metabolism*
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Bromine / analysis
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Cattle
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Chromatography, High Pressure Liquid
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Coumarins / chemistry
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Coumarins / isolation & purification
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Coumarins / pharmacology*
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Cyclohexanones / chemistry
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Cyclohexanones / isolation & purification
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Cyclohexanones / pharmacology*
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Epoxy Compounds / chemistry
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Epoxy Compounds / isolation & purification
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Epoxy Compounds / pharmacology*
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Platelet Aggregation / drug effects
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Salmonella typhimurium / genetics
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Spectrophotometry, Ultraviolet
Substances
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Anti-Bacterial Agents
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Antinematodal Agents
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Coumarins
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Cyclohexanones
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Epoxy Compounds
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lachnumon
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mycorrhizin A
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Bromine