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The plant antifungal isoflavone genistein is metabolized by Armillaria mellea Vahl to give non-fungitoxic products

2006; Taylor & Francis; Volume: 140; Issue: 2 Linguagem: Inglês

10.1080/11263500600756363

1724-5575

P. Curir, M. Dolci, Gabriella Corea, Francesco Galeotti, Virginia Lanzotti,

Microbial Natural Products and Biosynthesis

Abstract Armillaria mellea, the causal agent of root rot, is a fungal pathogen which proved able to convert the leguminous plant antifungal compound 4′,5,7-trihydroxyisoflavone (genistein) into intermediate metabolites. After suitable periods of incubation, the metabolites were extracted and concentrated from liquid culture media, containing both the isoflavone and the fungus. After purification by column chromatography, the molecular structure of the metabolites was determined by means of mass spectrometry and nuclear magnetic resonance analyses. Five different compounds were identified: 1,3,5-trihydroxybenzene, 4-hydroxyphenylacetic acid, 2,5-dihydroxyphenylacetic acid (homogentisic acid), its lactone 5-hydroxy-2(3H)-benzofuranone, and 1,4-benzoquinone. In vitro experiments showed that while the starting compound, i.e. genistein, has some activity in inhibiting the growth of the fungal pathogen, the degradation products are devoid of any appreciable fungitoxic activity. Moreover, results show that the isoflavone metabolites can be, at least partially, utilized by A. mellea as a carbon source.