title: Agropyrenol and agropyrenal, phytotoxins from Ascochyta agropyrina var. nana, a fungal pathogen of Elitrigia repens.
abstract: A strain of Ascochyta agropyrina var. nana, a fungal pathogen of the perennial weed Elytrigia repens, produced several toxins in a liquid medium, and its primary toxin, named agropyrenol, was characterized as a substituted salicylaldehyde on the basis of its chemical and spectroscopic properties. Its absolute stereochemistry was determined by Mosher's method. Two other minor metabolites were isolated from the same culture and named agropyrenal and agropyrenone, respectively. They were characterized as a trisubstituted naphthalene carbaldehyde and a pentasubstituted 3H-benzofuranone, respectively, using the same techniques. When assayed on leaves of several weed plants, i.e., Mercurialis annua, Chenopodium album and Setaria viridis, agropyrenol proved to be phytotoxic, causing the appearance of necrotic lesions, agropyrenal was less active, while agropyrenone was inactive. None of the compounds showed antibiotic, fungicidal or zootoxic activity.
authors.affiliation: Dipartimento di Scienze del Suolo, della Pianta, dell'Ambiente e delle Produzioni Animali, Università di Napoli Federico II, 80055 Portici, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Alessio
authors.initials: A
authors.lastname: Cimmino
authors.forename: Maurizio
authors.initials: M
authors.lastname: Vurro
authors.forename: Alexander
authors.initials: A
authors.lastname: Berestetskiy
authors.forename: Ciro
authors.initials: C
authors.lastname: Troise
authors.forename: Maria Chiara
authors.initials: MC
authors.lastname: Zonno
authors.forename: Andrea
authors.initials: A
authors.lastname: Motta
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
mesh_terms: D001203:Ascomycota / Q000737:chemistry* / Q000254:growth & development / Q000378:metabolism / Q000502:physiology*; D001547:Benzaldehydes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D046508:Culture Techniques; D031749:Elymus / Q000187:drug effects* / Q000382:microbiology*; D009281:Naphthalenes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D010572:Pest Control, Biological; D014118:Toxins, Biological / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*
chemical_list: D001547:Benzaldehydes; D009281:Naphthalenes; D014118:Toxins, Biological; C575646:agropyrenal; C575645:agropyrenol