Antimicrobial activity of clavines.
The antimicrobial activity of two clavine-type ergot alkaloids (agroclavine, festuclavine), and 16 derivatives against four human pathogenic bacteria and Candida albicans was determined. It is shown that all ergolines tested with one exception exhibit antibacterial properties against one to four bacteria species. The most active compounds are 6-allyl-6-norfestuclavine (minimal inhibitory concentration (MIC) 30 micrograms/ml against Staphylococcus aureus), 1-propyl-6-norfestuclavine (MIC 60 micrograms/ml against Escherichia coli), 6-cyano-6-norfestuclavine (MIC 250 micrograms/ml against Pseudomonas aeruginosa), and 1-methyl-agroclavine (MIC 200 micrograms/ml against Proteus vulgaris). 1-Allyl-6-norfestuclavine and 1-propyl-6-norfestuclavine showed a broad action spectrum: the growth of all four bacteria species and of Candida albicans was inhibited. The most effective antifungal compounds are 1-propyl-6-norfestuclavine and 6-cyano-6-norfestuclavine (MIC 250 micrograms/ml). Three alkaloids of different structure (codeine, emetine, quinine) are inactive up to 500 micrograms/ml against the bacteria species and C. albicans. The acute toxicity (mouse) is remarkably diminished by the modifications of the natural clavines.
D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D004876:Ergot Alkaloids / Q000494:pharmacology* / Q000633:toxicity; D007928:Lethal Dose 50; D051379:Mice; D008826:Microbial Sensitivity Tests
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D004876:Ergot Alkaloids