ABSTRACT
New 2-(2,4-dihalogenophenyl)-1-(1H-imidazol-1-yl)-3-(isoxazol-5-yl)propan-2-ols and 2-(2,4-dihalogenophenyl)-1-(1H-imidazol-1-yl)-3-(4,5-dihydroisoxazol-5-yl)propan-2-ols were synthesized by 1,3-dipolar cycloaddition between homopropargylic or homoallylic alcohols and in-situ generated nitrile oxide. Their antifungal activity was evaluated against Candida albicans, C. glabrata, Aspergillus fumigatus and an azole-resistant petite mutant of C. glabrata. Preliminary SAR results are discussed.
Subject(s)
Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Aspergillus fumigatus/drug effects , Candida albicans/drug effects , Candida glabrata/drug effects , Isoxazoles , Antifungal Agents/chemistry , Candida glabrata/genetics , Isoxazoles/chemical synthesis , Isoxazoles/chemistry , Isoxazoles/pharmacology , Microbial Sensitivity Tests , Molecular Structure , MutationABSTRACT
Plants of the Asteraceae family are known as a source of sesquiterpene lactones with interesting biological activities. The purification of several xanthanolides (xanthathin, 4-epi-xanthanol and 4-epi-isoxanthanol) was realized in one step, directly from the crude chloroformic extract of the leaves of X. macrocarpum by silica gel chromatography and for the first time by liquid/liquid chromatography (counter-current chromatography/centrifugal partition chromatography), using a FCPC 5L (Fast centrifugal partition chromatograph, Kromaton Technologies, Angers, France). Recovery, purity of xanthathin and solvent consumption were improved with the liquid/liquid chromatography compared to solid/liquid chromatography.
Subject(s)
Centrifugation/methods , Chromatography, Gel/methods , Furans/chemistry , Xanthium/chemistry , Furans/analysis , Molecular Structure , Reproducibility of ResultsABSTRACT
There are thirteen endemic species belonging to the genus Garcinia in New Caledonia. Among them, G. virgata is an evergreen tree mainly growing in the rain forests of this island. Fractionation of the cyclohexane extract of the stem bark of this plant produced the known benzophenones guttiferone E and xanthochymol, together with two new guttiferone analogues, namely guttiferones I and J. The structures of these benzophenones were mainly elucidated using 1D and 2D NMR spectroscopy. Compounds and were weakly cytotoxic on the KB cell line with IC50 values of 4.70 and 5.0 microg/mL respectively.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Benzophenones/isolation & purification , Garcinia/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Benzophenones/chemistry , Humans , KB Cells , Magnetic Resonance Spectroscopy , Molecular Conformation , New CaledoniaABSTRACT
Two new xanthones, 6-O-methyl-2-deprenylrheediaxanthone B (1) and vieillardixanthone (2), were isolated from the stem bark of Garcinia vieillardii, as were four known compounds (4-7). The structures of 1 and 2 were determined by means of spectroscopic analysis and chemical derivatization. Each isolate was tested for its antioxidant properties based on a scavenging activity study using the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical.
