Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis
Two diastereomeric furanones, (4S,5S)-5-(4′-methhyl-3′-pentenyl)-4-hydroxy-5 -methyldihydrofuran-2-one 1 and (4S,5R)-5-(4′-methyl-3′-pentenyl)-4-hydroxy -5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochimistries 1 and 2 were ascert...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_09574166_v12_n7_p991_Viturro |
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todo:paper_09574166_v12_n7_p991_Viturro2023-10-03T15:52:22Z Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis Viturro, C.I. Maier, M.S. Stortz, C.A. De la Fuente, J.R. 5 (4' methyl 3' pentenyl) 4 hydroxy 5 methyldihydrofuran 2 one furanone derivative unclassified drug antifungal activity article Cladosporium cucumerinum conformation diastereoisomer molecular model mutisia friesiana nuclear Overhauser effect priority journal stereochemistry structure analysis Two diastereomeric furanones, (4S,5S)-5-(4′-methhyl-3′-pentenyl)-4-hydroxy-5 -methyldihydrofuran-2-one 1 and (4S,5R)-5-(4′-methyl-3′-pentenyl)-4-hydroxy -5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochimistries 1 and 2 were ascertained from NOESY NMR data. Comparison between experimental and calculated 1H-1H vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher's method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum. © 2001 Elsevier Science Ltd. Fil:Maier, M.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09574166_v12_n7_p991_Viturro |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
5 (4' methyl 3' pentenyl) 4 hydroxy 5 methyldihydrofuran 2 one furanone derivative unclassified drug antifungal activity article Cladosporium cucumerinum conformation diastereoisomer molecular model mutisia friesiana nuclear Overhauser effect priority journal stereochemistry structure analysis |
| spellingShingle |
5 (4' methyl 3' pentenyl) 4 hydroxy 5 methyldihydrofuran 2 one furanone derivative unclassified drug antifungal activity article Cladosporium cucumerinum conformation diastereoisomer molecular model mutisia friesiana nuclear Overhauser effect priority journal stereochemistry structure analysis Viturro, C.I. Maier, M.S. Stortz, C.A. De la Fuente, J.R. Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis |
| topic_facet |
5 (4' methyl 3' pentenyl) 4 hydroxy 5 methyldihydrofuran 2 one furanone derivative unclassified drug antifungal activity article Cladosporium cucumerinum conformation diastereoisomer molecular model mutisia friesiana nuclear Overhauser effect priority journal stereochemistry structure analysis |
| description |
Two diastereomeric furanones, (4S,5S)-5-(4′-methhyl-3′-pentenyl)-4-hydroxy-5 -methyldihydrofuran-2-one 1 and (4S,5R)-5-(4′-methyl-3′-pentenyl)-4-hydroxy -5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochimistries 1 and 2 were ascertained from NOESY NMR data. Comparison between experimental and calculated 1H-1H vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher's method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum. © 2001 Elsevier Science Ltd. |
| format |
JOUR |
| author |
Viturro, C.I. Maier, M.S. Stortz, C.A. De la Fuente, J.R. |
| author_facet |
Viturro, C.I. Maier, M.S. Stortz, C.A. De la Fuente, J.R. |
| author_sort |
Viturro, C.I. |
| title |
Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis |
| title_short |
Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis |
| title_full |
Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis |
| title_fullStr |
Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis |
| title_full_unstemmed |
Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis |
| title_sort |
antifungal diastereomeric furanones from mutisia friesiana: structural determination and conformational analysis |
| url |
http://hdl.handle.net/20.500.12110/paper_09574166_v12_n7_p991_Viturro |
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