ABSTRACT
A novel metabolite, benesudon, possessing antibacterial, antifungal, cytotoxic and phytotoxic activities, was isolated from submerged cultures of the ascomycete Mollisia benesuada. Benesudon contains a reactive alpha-methyleneketone moiety which is believed to be responsible for its antibiotic activities, it reacts with cysteine and the reaction products are devoid of biological activities. Benesudon is the first secondary metabolite described from Mollisia benesuada, and its structure was determined by spectroscopic techniques.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Ascomycota/metabolism , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Ascomycota/classification , Cell Line , Fermentation , Pyrans/isolation & purification , Pyrans/pharmacologyABSTRACT
In the course of our search for new biologically active metabolites, lachnellin A (1), a metabolite with high cytotoxic and antimicrobial activities, the structurally related lachnellins B, C and D (3, 4, 7), and naphthalene-1,3,8-triol (8), an inhibitor of malate synthase (EC 4.1.3.2), were isolated from submerged cultures of the ascomycete Lachnellula sp. A 32-89. The antimicrobial, cytotoxic and phytotoxic activities of lachnellin A depended on its reactivity and could be abolished by the addition of cysteine. The enzyme inhibiting activity of (8) was due to reactive intermediates during melanization and was no longer observed in the presence of serum albumin. In addition, rac-scytalone (9), (+)-trans-3,4-dihydro-3,4,8-trihydroxy-1 (2H)-naphthalenone (10), 2,5-dihydroxytoluene (11), and (R)-(-)-5-methylmellein (12) were obtained from the same source and biologically characterized.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antimetabolites/pharmacology , Ascomycota , Cell Survival/drug effects , Ketones/pharmacology , Malate Synthase/antagonists & inhibitors , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Antimetabolites/chemistry , Antimetabolites/isolation & purification , Avian Myeloblastosis Virus/enzymology , Bacteria/drug effects , Cell Line , Chitin Synthase/antagonists & inhibitors , Fungi/drug effects , HeLa Cells , Humans , Ketones/chemistry , Ketones/isolation & purification , Leukemia L1210 , Leukemia, Basophilic, Acute , Mice , Microbial Sensitivity Tests , Oryza , Rats , Reverse Transcriptase Inhibitors/pharmacology , Seeds/drug effects , Seeds/physiology , Tumor Cells, CulturedABSTRACT
Several chlorinated metabolites with nematicidal, antimicrobial, and cytotoxic activities were isolated from submerged cultures of the ascomycete Lachnum papyraceum. Three compounds were identified as (+)-mycorrhizin A (3), (+)-chloromycorrhizin A (4) and (+)-dechloromycorrhizin A (5). The occurrence of 5 as a natural product is new. Two compounds, lachnumon (1) and lachnumol A (2), were found to be new fungal metabolites with cytotoxic, nematicidal and antimicrobial activities.
