title: Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid.
abstract: Bioassay-directed isolation of antifungal compounds from an ethyl acetate extract of Ruta graveolens leaves yielded two furanocoumarins, one quinoline alkaloid, and four quinolone alkaloids, including a novel compound, 1-methyl-2-[6'-(3' ',4' '-methylenedioxyphenyl)hexyl]-4-quinolone. The (1)H and (13)C NMR assignments of the new compound are reported. Antifungal activities of the isolated compounds, together with 7-hydroxycoumarin, 4-hydroxycoumarin, and 7-methoxycoumarin, which are known to occur in Rutaceae species, were evaluated by bioautography and microbioassay. Four of the alkaloids had moderate activity against Colletotrichum species, including a benomyl-resistant C. acutatum. These compounds and the furanocoumarins 5- and 8-methoxypsoralen had moderate activity against Fusarium oxysporum. The novel quinolone alkaloid was highly active against Botrytis cinerea. Phomopsis species were much more sensitive to most of the compounds, with P. viticola being highly sensitive to all of the compounds.
authors.affiliation: Department of Life Science, Second University of Naples, Via Vivaldi 43, 81100 Naples, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Oliva
authors.forename: Kumudini M
authors.initials: KM
authors.lastname: Meepagala
authors.forename: David E
authors.initials: DE
authors.lastname: Wedge
authors.forename: Dewayne
authors.initials: D
authors.lastname: Harries
authors.forename: Amber L
authors.initials: AL
authors.lastname: Hale
authors.forename: Giovanni
authors.initials: G
authors.lastname: Aliotta
authors.forename: Stephen O
authors.initials: SO
authors.lastname: Duke
mesh_terms: D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology; D020171:Botrytis / Q000187:drug effects; D020231:Colletotrichum / Q000187:drug effects; D005659:Fungicides, Industrial / Q000302:isolation & purification* / Q000494:pharmacology; D011564:Furocoumarins / Q000302:isolation & purification / Q000494:pharmacology; D005670:Fusarium / Q000187:drug effects; D018515:Plant Leaves / Q000737:chemistry*; D011804:Quinolines / Q000302:isolation & purification / Q000494:pharmacology; D015363:Quinolones / Q000302:isolation & purification* / Q000494:pharmacology; D032105:Ruta / Q000737:chemistry*
chemical_list: C472248:1-methyl-2-(6'-(3' ',4' '-methylenedioxyphenyl)hexyl)-4-quinolone; D000470:Alkaloids; D005659:Fungicides, Industrial; D011564:Furocoumarins; D011804:Quinolines; D015363:Quinolones