Phyllostoxin and phyllostin, bioactive metabolites produced by Phyllosticta cirsii, a potential mycoherbicide for Cirsium arvense biocontrol

Journal of Agricultural and Food Chemistry
Antonio EvidenteA Motta

Abstract

Phyllosticta cirsii, a fungal pathogen isolated from diseased Cirsium arvense leaves and evaluated as a biocontrol agent of this noxious perennial weed, produces different phytotoxic metabolites with potential herbicidal activity when grown in liquid cultures. Phyllostictines A-D, four novel oxazatricycloalkenones, were recently isolated from this pathogen and chemically and biologically characterized. Further purification of the same organic extract provided two other metabolites, named phyllostoxin (1) and phyllostin (2), which were characterized by spectroscopic technique (essentially NMR and MS). Phyllostoxin and phyllostin proved to be a new pentasubstituted bicyclo-octatrienyl acetic acid ester and a new pentasubstituted hexahydrobenzodioxine carboxylic acid methyl ester, respectively. When tested on punctured C. arvense leaves, phyllostoxin proved to be highly phytotoxic, causing rapid and large necrosis, whereas phyllostin had no phytotoxicity in this bioassay. This is not surprising, considering the noteworthy structural differences between the two compounds, suggesting the presence of active functional groups in phyllostoxin not present in the other metabolite. These results further support the focused approach of fin...Continue Reading

Citations

Aug 21, 2013·British Poultry Science·C OrhanK Sahin
Aug 31, 2012·FEMS Microbiology Reviews·Ioannis StergiopoulosPierre J G M De Wit
Oct 8, 2015·Natural Product Reports·Alessio CimminoAntonio Evidente
Dec 25, 2019·Brazilian Journal of Microbiology : [publication of the Brazilian Society for Microbiology]·Halison Correa GoliasJoão Alencar Pamphile
Apr 27, 2010·Journal of Natural Products·ElHadj Saidou BaldeAntonio Evidente

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