Antibacterial properties of 3 H-spiro[1-benzofuran-2,1'-cyclohexane] derivatives from Heliotropium filifolium.
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.
Urzúa
Alejandro
A
Facultad de Química y Biología, Casilla 40, Correo 33, Universidad de Santiago de Chile, Santiago, Chile. alejandro.urzua@usach.cl
Echeverría
Javier
J
Rezende
Marcos C
MC
Wilkens
Marcela
M
D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology; D003510:Cyclohexanes; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D028162:Heliotropium / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010936:Plant Extracts; D013141:Spiro Compounds; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D001572:Benzofurans; D003510:Cyclohexanes; D010936:Plant Extracts; D013141:Spiro Compounds; C441666:filifolone; C506365:Cyclohexane; C105430:benzofuran