Stagonolides G−I and Modiolide A, Nonenolides Produced by Stagonospora cirsii, a Potential Mycoherbicide for Cirsium arvense

Stagonospora cirsii Davis, a fungal pathogen isolated from Cirsium arvense (commonly called Canada thistle) and proposed as a potential mycoherbicide of this perennial noxious weed, produces phytotoxic metabolites in liquid and solid cultures. Stagonolide, the main phytotoxic metabolite, and five ne...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2008-11, Vol.71 (11), p.1897-1901
Main Authors: Evidente, Antonio, Cimmino, Alessio, Berestetskiy, Alexander, Andolfi, Anna, Motta, Andrea
Format: Article
Language:English
Subjects:
Ascomycota - chemistry
bioassays
biological control agents
chemical structure
chicory
Cichorium intybus
Cirsium - drug effects
Cirsium - growth & development
Cirsium arvense
Dose-Response Relationship, Drug
esters
Herbicides - chemistry
Herbicides - isolation & purification
Herbicides - pharmacology
heterocyclic compounds
Heterocyclic Compounds, 1-Ring - chemistry
Heterocyclic Compounds, 1-Ring - isolation & purification
Lactones - chemistry
Lactones - isolation & purification
modiolide
mycoherbicides
nonenolide
noxious weeds
phyllostictines
phyllostoxins
phytotoxicity
plant pathogenic fungi
seedlings
spectral analysis
stagonolide
Stagonospora
Stagonospora cirsii
weed control
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Summary:Stagonospora cirsii Davis, a fungal pathogen isolated from Cirsium arvense (commonly called Canada thistle) and proposed as a potential mycoherbicide of this perennial noxious weed, produces phytotoxic metabolites in liquid and solid cultures. Stagonolide, the main phytotoxic metabolite, and five new related nonenolides, named stagonolides B−F, were isolated from the fungus. When grown on solid culture, nonenolide yields increased. A further four nonenolides were isolated and characterized by spectroscopy. Three were new compounds and named stagonolides G−I, and the fourth was identified as modiolide A, previously isolated from Paraphaeosphaeria sp., a fungus separated from the horse mussel. Leaf disk-puncture assays at 1 mg/mL of stagonolides H−I and modiolide A were phytotoxic to C. arvense. Only stagonolide H inhibited chicory seedling root growth. The most potent toxin, stagonolide H, indicated selectivity when tested on leaves of eight different plants: Canada thistle was most sensitive to the compound.
ISSN:0163-3864
1520-6025
DOI:10.1021/np800415w