Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis

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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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Detalles Bibliográficos
Autor principal: Viturro, C.I
Otros Autores: Maier, M.S, Stortz, C.A, De la Fuente, J.R
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2001
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Viturro, C.I. 
245 1 0 |a Antifungal diastereomeric furanones from Mutisia friesiana: Structural determination and conformational analysis 
260 |c 2001 
270 1 0 |m Maier, M.S.; Departamento de Quimica Organica, Facultad de Cien. Exactas Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: maier@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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504 |a Maier, M.S., González Marimón, D.I., Stortz, C.A., Adler, M.T., (1999) J. Nat. Prod., 62, pp. 1565-1567 
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520 3 |a 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.  |l eng 
536 |a Detalles de la financiación: Universidad Nacional de Asunción 
536 |a Detalles de la financiación: Universidad de Buenos Aires 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: This work was supported by the SeCTER, Universidad Nacional de Jujuy. The authors would like to thank CONICET and the Universidad de Buenos Aires for partial financial support. They are indebted to UMYMFOR (CONICET-FCEN, UBA) for the NMR spectra and LANAIS-EMAR (CONICET-FCEN, UBA) for the mass spectra. They would also like to thank Dr. Jorge Palermo for performing the NMR spectra and are grateful to Ing. Novara of the Facultad de Ciencias Naturales, Universidad de Salta for the taxonomic identification of M. friesiana . M.S.M. and C.A.S. are Research Members of the National Research Council of Argentina (CONICET). 
593 |a Facultad de Ingeniería, Universidad Nacional de Jujuy, Gorriti 237, 4600 S. S. de Jujuy, Jujuy, Argentina 
593 |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Facultad de Ciencias Exactas, Universidad Nacional de Salta, Buenos Aires 177, 4400 Salta, Salta, Argentina 
690 1 0 |a 5 (4' METHYL 3' PENTENYL) 4 HYDROXY 5 METHYLDIHYDROFURAN 2 ONE 
690 1 0 |a FURANONE DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ANTIFUNGAL ACTIVITY 
690 1 0 |a ARTICLE 
690 1 0 |a CLADOSPORIUM CUCUMERINUM 
690 1 0 |a CONFORMATION 
690 1 0 |a DIASTEREOISOMER 
690 1 0 |a MOLECULAR MODEL 
690 1 0 |a MUTISIA FRIESIANA 
690 1 0 |a NUCLEAR OVERHAUSER EFFECT 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a STRUCTURE ANALYSIS 
700 1 |a Maier, M.S. 
700 1 |a Stortz, C.A. 
700 1 |a De la Fuente, J.R. 
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