Usnic acid derivatives from Leprocaulon microscopicum |
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Authors: | Marion Millot Mourad Kaouadji Yves Champavier Aurélie Gamond Alain Simon Albert J Chulia |
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Institution: | 1. Laboratoire de Chimie des Substances Naturelles, EA 1069, Institut GEIST, Faculté de Pharmacie, 2, Rue Docteur Marcland, F-87025 Limoges Cedex, France;2. Département de Chimie, Faculté des Sciences et Techniques, 123, Avenue A. Thomas, F-87060 Limoges Cedex, France;3. Service de Résonance Magnétique Nucléaire, Plateforme SCRABL, Faculté de Pharmacie, 2, Rue Docteur Marcland, F-87025 Limoges Cedex, France |
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Abstract: | In addition to known dibenzofuran derivatives such as (?)-usnic acid, (?)-isousnic acid and (?)-placodiolic acid, a Leprocaulon microscopicum acetone extract yielded a new compound, (±)-9-O-methylplacodiolic acid in a keto-enol equilibrium focused on the C-ring. Structures were established using mass spectrometry and combination of 1D and 2D NMR spectral data. 13C assignments of placodiolic acid were revised. Tautomers of the (±)-9-O-methylplacodiolic acid were only separated by GC and a thorough fragmentation study confirmed the structural features. To complete the study, evaluation of antiproliferative effects on HT-29 human colorectal cancer cells showed moderate activity for (?)-usnic acid only. |
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