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:	Petit,Philippe, Lucas,Esther M. F., Abreu,Lucas M, Pfenning,Ludwig H, Takahashi,Jacqueline A
Lenguaje:	English
Publicado:	Pontificia Universidad Católica de Valparaíso 2009
Materias:	antibacterial activity cerrado naphthalenoids Penicillium secondary metabolites
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-34582009000400008
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spelling	oai:scielo:S0717-345820090004000082010-04-19Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soilPetit,PhilippeLucas,Esther M. F.Abreu,Lucas MPfenning,Ludwig HTakahashi,Jacqueline A antibacterial activity cerrado naphthalenoids Penicillium secondary metabolites 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).info:eu-repo/semantics/openAccessPontificia Universidad Católica de ValparaísoElectronic Journal of Biotechnology v.12 n.4 20092009-10-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-34582009000400008en10.4067/S0717-34582009000400008
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	antibacterial activity cerrado naphthalenoids Penicillium secondary metabolites
spellingShingle	antibacterial activity cerrado naphthalenoids Penicillium secondary metabolites Petit,Philippe Lucas,Esther M. F. Abreu,Lucas M Pfenning,Ludwig H Takahashi,Jacqueline A Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil
description	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).
author	Petit,Philippe Lucas,Esther M. F. Abreu,Lucas M Pfenning,Ludwig H Takahashi,Jacqueline A
author_facet	Petit,Philippe Lucas,Esther M. F. Abreu,Lucas M Pfenning,Ludwig H Takahashi,Jacqueline A
author_sort	Petit,Philippe
title	Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil
title_short	Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil
title_full	Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil
title_fullStr	Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil
title_full_unstemmed	Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil
title_sort	novel antimicrobial secondary metabolites from a penicillium sp. isolated from brazilian cerrado soil
publisher	Pontificia Universidad Católica de Valparaíso
publishDate	2009
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-34582009000400008
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Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil

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