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Electronic Journal of Biotechnology
Universidad Católica de Valparaíso
ISSN: 0717-3458
Vol. 12, No. 4, 2009
Bioline Code: ej09043
Full paper language: English
Document type: Research Article
Document available free of charge

Electronic Journal of Biotechnology, Vol. 12, No. 4, 2009

 en Novel antimicrobial secondary metabolites from a Penicillium check for this species in other resources sp. isolated from Brazilian cerrado soil
Petit, P.; Lucas, E.M.F.; Abreu, L.M.; Pfenning, L.H. & Takahashi, J.A.

Abstract

The morphological features of a Penicillium check for this species in other resources , 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).

Keywords
antibacterial activity, cerrado, naphthalenoids, Penicillium, secondary metabolites.

 
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