Stagonolides B−F, Nonenolides Produced by Stagonospora cirsii, a Potential Mycoherbicide of Cirsium arvense

Stagonospora cirsii, a fungal pathogen isolated from Cirsium arvense and proposed as a potential mycoherbicide of this perennial noxious weed, produces phytotoxic metabolites in liquid and solid cultures. Recently, the main metabolite, stagonolide (1), with interesting phytotoxic properties, was iso...

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Bibliographic Details
Published in:	Journal of natural products (Washington, D.C.) D.C.), 2008-01, Vol.71 (1), p.31-34
Main Authors:	Evidente, Antonio, Cimmino, Alessio, Berestetskiy, Alexander, Mitina, Galina, Andolfi, Anna, Motta, Andrea
Format:	Article
Language:	eng
Subjects:	Arvenses Ascomycota - chemistry chemical structure Cirsium - drug effects Cirsium arvense Colpoda steinii Herbicides - chemistry Herbicides - isolation & purification Herbicides - pharmacology heterocyclic compounds Heterocyclic Compounds, 1-Ring - chemistry Heterocyclic Compounds, 1-Ring - isolation & purification Heterocyclic Compounds, 1-Ring - pharmacology lactones Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Molecular Structure mycoherbicides nonenolide noxious weeds Nuclear Magnetic Resonance, Biomolecular phytotoxicity Plant Leaves - chemistry plant pathogenic fungi Sonchus arvensis spectral analysis stagonolide Stagonospora Stagonospora cirsii Structure-Activity Relationship structure-activity relationships weed control
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Summary:	Stagonospora cirsii, a fungal pathogen isolated from Cirsium arvense and proposed as a potential mycoherbicide of this perennial noxious weed, produces phytotoxic metabolites in liquid and solid cultures. Recently, the main metabolite, stagonolide (1), with interesting phytotoxic properties, was isolated from a liquid culture and characterized as a new nonenolide. In the present work this same fungus, grown in solid culture, exhibited an increased capacity to produce nonenolides. Five new nonenolides, named stagonolides B−F (2–6), were isolated and characterized using spectroscopic methods. When tested by a leaf disk puncture assay at a concentration of 1 mg/mL, these compounds showed no toxicity to C. arvense and Sonchus arvensis, whereas stagonolide (1) was highly toxic. Stagonolide (1) and stagonolide C (3) were weakly toxic to Colpoda steinii, a protozoan, when tested at 0.05 mg/mL, with the other stagonolides nontoxic. A number of structure–activity relationship observations were made.
ISSN:	0163-3864 1520-6025