Antibacterial Properties of 3 H-Spiro[1-benzofuran-2,1 '-cyclohexane] Derivatives from Heliotropium filifolium

Urzúa, A; Echeverría, J.; Rezende, MC; WILKENS, M

Abstract

A re-examination of cuticular components of Heliotropium filifolium allowed the isolation of four new compounds: 3′-hydroxy-2′,2′, 6′-trimethyl-3H-spiro[1-benzofuran-2,1′-cyclohexane]-5-carboxylic acid (2), methyl 3′-acetyloxy-2′,2′,6′-trimethyl-3H- spiro[1-benzofuran-2,1′-cyclohexane]-5-carboxylate (3), methyl 3′-isopentanoyloxy-2′,2′,6′-trimethyl-3H-spiro[1- benzofuran-2,1′-cyclohexane]-5-carboxylate (4) and methyl 3′-benzoyloxy-2′,2′,6′-trimethyl-3H-spiro[1-benzofuran- 2,1′-cyclohexane]-5-carboxylate (5). Compounds 2-5 were identified by their spectroscopic analogies with filifolinol (1), and their structures confirmed by chemical correlation with 1. The antimicrobial properties of the compounds were tested against Gram positive and Gram negative bacteria. Some of them proved to be active against Gram positive, but inactive against Gram negative bacteria. In searching for structure-activity relationships from the obtained MIC values, lipophilicity was shown to be an important variable. © 2008 by the authors; licensee Molecular Diversity Preservation International.

Más información

Título según WOS: Antibacterial Properties of 3 H-Spiro[1-benzofuran-2,1 '-cyclohexane] Derivatives from Heliotropium filifolium
Título según SCOPUS: Antibacterial properties of 3 H-spiro[1-benzofuran-2,1'-cyclohexane] derivatives from Heliotropium filifolium
Título de la Revista: MOLECULES
Volumen: 13
Número: 10
Editorial: MDPI
Fecha de publicación: 2008
Página de inicio: 2385
Página final: 2393
Idioma: English
URL: http://www.mdpi.com/1420-3049/13/10/2385/
DOI:

10.3390/molecules13102385

Notas: ISI, SCOPUS