title: Drazepinone, a trisubstituted tetrahydronaphthofuroazepinone with herbicidal activity produced by Drechslera siccans.
abstract: When grown in a minimal-defined medium, a strain of Drechslera siccans, a pathogenic fungus isolated from seeds of Lolium perenne, produced phytotoxic metabolites. This strain is one of the best toxin producers among several grass pathogenic fungal strains collected and tested to find phytotoxins to be used as natural herbicides of monocot weeds. From the culture filtrates of D. siccans, we isolated a new phytotoxic trisubstituted naphthofuroazepinone, named drazepinone, and characterised it as a 3,5,12a-trimethyl-2,5,5a,12a-tetrahydro-1H-naphtho[2',3':4,5]furo[2,3-b]azepin-2-one. Assayed at 2 microg microl(-1) solution the novel metabolite proved to have broad-spectrum herbicidal properties, without antibacterial and antifungal activities, and low zootoxic activity. Its original chemical structure and the interesting biological properties make drazepinone a potential natural herbicide.
authors.affiliation: Dipartimento di Scienze del Suolo della Pianta e dell'Ambiente, Università di Napoli Federico II, Via Università 100, I-80055 Portici, Italy. evidente@unina.it
authors.forename: Antonio
authors.initials: A
authors.lastname: Evidente
authors.forename: Anna
authors.initials: A
authors.lastname: Andolfi
authors.forename: Maurizio
authors.initials: M
authors.lastname: Vurro
authors.forename: Mariano
authors.initials: M
authors.lastname: Fracchiolla
authors.forename: Maria Chiara
authors.initials: MC
authors.lastname: Zonno
authors.forename: Andrea
authors.initials: A
authors.lastname: Motta
mesh_terms: D001203:Ascomycota / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006540:Herbicides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018515:Plant Leaves
chemical_list: D001381:Azepines; D006540:Herbicides; D009281:Naphthalenes; C501249:drazepinone