Natural Fungicides from Ruta graveolens L. Leaves, Including a New Quinolone Alkaloid

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 1H and 13C...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2003-02, Vol.51 (4), p.890-896
Main Authors: Oliva, Anna, Meepagala, Kumudini M, Wedge, David E, Harries, Dewayne, Hale, Amber L, Aliotta, Giovanni, Duke, Stephen O
Format: Article
Language:English
Subjects:
Alkaloids - isolation & purification
Alkaloids - pharmacology
Biological and medical sciences
Botrytis - drug effects
Botrytis cinerea
Chemical control
Colletotrichum - drug effects
Control
Fundamental and applied biological sciences. Psychology
Fungal plant pathogens
Fungicides, Industrial - isolation & purification
Fungicides, Industrial - pharmacology
Furocoumarins - isolation & purification
Furocoumarins - pharmacology
Fusarium - drug effects
Fusarium oxysporum
Phytopathology. Animal pests. Plant and forest protection
Plant Leaves - chemistry
Quinolines - isolation & purification
Quinolines - pharmacology
Quinolones - isolation & purification
Quinolones - pharmacology
Ruta - chemistry
Ruta graveolens
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Summary: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 1H and 13C 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. Keywords: Botrytis cinerea; Colletotrichum acutatum; C. fragariae; C. gloeosporioides; fungicide; furanocoumarin; Fusarium oxysporum; Phomopsis viticola; P. obscurans; psoralen; quinoline alkaloid; quinolone alkaloid; rue; Ruta graveolens
ISSN:0021-8561
1520-5118
DOI:10.1021/jf0259361