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Title:   Author  item
                                            EVIDENTE, ANTONIO - UNIV. DI NAPOLI-ITALYitem
                                            CIMMINO, ALESSIO - UNIV. DI NAPOLI-ITALYitem
                                            ANDOLFI, ANNA - UNIV. DI NAPOLI-ITALYitem
                                            VURRO, MAURIZIO - INST. DI SCIENZE-ITALYitem
                                            ZONNO, MARIA - INST. DI SCIENZE-ITALYitem
                                            Cantrell, Charlesitem
                                            MOTTA, ANDREA - INST. DI CHIMICA BIO-IT.
  Submitted to: Tetrahedron
                                    Publication Type: Peer Reviewed Journal
                                    Publication Acceptance Date: 12/6/2007
                                    Publication  Date: 12/8/2007
                                    Citation: Evidente, A., Cimmino, A., Andolfi, A., Vurro, M., Zonno, M.C., Cantrell, C.L., Motta, A. 2007. Phyllostictines A-D, Oxazatricycloalkenones Produced by Phyllosticta cirsii, A Potential Mycoherbicide for Cirsium arvense Biocontrol. Tetrahedron.  64:1612-1619.Interpretive Summary: Cirsium arvense (L.) Scop. (commonly called Canada thistle) is a persistent perennial weed that grows vigorously, forming dense colonies, and spreading by roots growing horizontally that give rise to aerial shoots. It spreads by seed either by wind or as a contaminant in crop seed. Canada thistle is native to south eastern Europe and the eastern Mediterranean area. It has spread to most temperate parts of the world and is considered an important weed all around the world as it infests many habitats such as cultivated fields, roadsides, pastures and rangeland, railway embankments, and lawns. There is no easy method of control, and all methods require follow-up. Although there are no effective biological control organisms available at this time, search for efficacious biocontrol microorganisms and natural herbicides is receiving a renewed interest. Phyllosticta cirsii, a fungal pathogen isolated from Cirsium arvense and proposed as biocontrol agent of this noxious perennial weed, produces in liquid cultures different phytotoxic metabolites with potential herbicidal activity. Four new oxazatricycloalkenones, named phyllostictines A-D, were isolated and characterized using essentially spectroscopic and chemical methods.
                                Technical Abstract: Phyllosticta cirsii, a fungal pathogen isolated from Cirsium arvense and proposed as biocontrol agent of this noxious perennial weed, produces in liquid cultures different phytotoxic metabolites with potential herbicidal activity. Four new oxazatricycloalkenones, named phyllostictines A-D, were isolated and characterized using essentially spectroscopic and chemical methods. Tested by leaf-puncture assay on the fungal host plant phyllostictine A proved to be highly toxic. The phytotoxicity decreases when both the dimension and the conformational freedom of the macrocyclic ring change, as in phyllostictines B and D, and it is totally lost when also the functionalization of the same ring is modified, as in phyllostictine C. Beside its phytotoxic properties, phyllostictine A has no antifungal activity, an interesting antibiotic activity only against Gram positive bacteria, and a noticeable zootoxic activity when tested at high concentrations. The integrity of the oxazatricycloalkenone system appears to be an important feature to preserve these activities.


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