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

doi:10.3390/molecules13102385

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Molecules 2008, 13(10), 2385-2393; doi:10.3390/molecules13102385

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

Alejandro Urzúa* , Javier Echeverría, Marcos C. Rezende and Marcela Wilkens

Facultad de Química y Biología, Casilla 40, Correo 33, Universidad de Santiago de Chile, Santiago, Chile

* Author to whom correspondence should be addressed.

Received: 3 July 2008; in revised form: 27 August 2008 / Accepted: 16 September 2008 / Published: 1 October 2008

(This article belongs to the Special Issue Spiro Compounds)

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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-benzo-furan-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.

Keywords: 3H-spiro[1-benzofuran-2; 1’-cyclohexane] derivatives; Heliotropium filifolium; antibacterial properties

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MDPI and ACS Style

Urzúa, A.; Echeverría, J.; Rezende, M.C.; Wilkens, M. Antibacterial Properties of 3 H-Spiro[1-benzofuran-2,1’-cyclohexane] Derivatives from Heliotropium filifolium. Molecules 2008, 13, 2385-2393.

AMA Style

Urzúa A, Echeverría J, Rezende MC, Wilkens M. Antibacterial Properties of 3 H-Spiro[1-benzofuran-2,1’-cyclohexane] Derivatives from Heliotropium filifolium. Molecules. 2008; 13(10):2385-2393.

Chicago/Turabian Style

Urzúa, Alejandro; Echeverría, Javier; Rezende, Marcos C.; Wilkens, Marcela. 2008. "Antibacterial Properties of 3 H-Spiro[1-benzofuran-2,1’-cyclohexane] Derivatives from Heliotropium filifolium." Molecules 13, no. 10: 2385-2393.

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