Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil
The morphological features of a Penicillium, isolated from Brazilian cerrado soil, were characterized and showed to be distinctly different from all well-defined Penicillium species. Chemical and biological investigation on the ethyl acetate extract of this Penicillium isolate resulted in the isolat...
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| Autores principales: | , , , , |
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| Lenguaje: | English |
| Publicado: |
Pontificia Universidad Católica de Valparaíso
2009
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| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-34582009000400008 |
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| Sumario: | The morphological features of a Penicillium, isolated from Brazilian cerrado soil, were characterized and showed to be distinctly different from all well-defined Penicillium species. Chemical and biological investigation on the ethyl acetate extract of this Penicillium isolate resulted in the isolation of three new naphthalenoids: a major metabolite, methyl 6-acetyl-4-methoxy-5,7,8-trihydroxynaphthalene-2-carboxylate and two minor ones, methyl 6-acetyl-4-methoxy-7,8-dihydroxynaphthalene-2-carboxylate and methyl 6-acetyl-4-methoxy-5,8-dihydroxynaphthalene-2-carboxylate. Their structures were determined based on their mono and bidimensional nuclear magnetic resonance data. Acetyl, allyl and methoxyl derivatives of the major metabolite were prepared in order to establish structure-activity relation. Antimicrobial activity of the major natural product and its semi-synthetic derivatives was screened by macro dilution methodology and the corresponding minimum inhibitory concentrations were determined. Natural secondary metabolite methyl 6-acetyl-4-methoxy-5,7,8-trihydroxynaphthalene-2-carboxylate, isolated in a very high yield (0.3175 mg.L-1) showed to be the most active compound, possessing expressive activity against Candida albicans (minimum inhibitory concentration (MIC) 32 µg/mL), Listeria monocitogenes and Bacillus cereus (MIC 64 µg/mL for both). |
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