Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations

Two new sulfated steroidal hexaglycosides, anasterosides A (2) and B (3), along with the known versicoside A (1) have been isolated from the Patagonian starfish Anasterias minuta. Their structures have been elucidated by spectroscopic analysis (NMR and FABMS) and chemical transformations. Compounds...

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Detalles Bibliográficos
Autores principales: Chludil, H.D., Seldes, A.M., Maier, M.S.
Formato: JOUR
Materias:
anasteroside a
anasteroside b
antifungal agent
glycoside
thornasteroside
unclassified drug
versicoside a
anasterias minuta
antifungal activity
article
Asterias
chemical modification
Cladosporium cucumerinum
correlation analysis
drug isolation
nonhuman
nuclear magnetic resonance spectroscopy
plant fungus interaction
structure activity relation
structure analysis
sulfation and desulfurization
Animals
Antifungal Agents
Argentina
Cholestenones
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Cladosporium
Dose-Response Relationship, Drug
Glycosides
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pregnenes
Starfish
Structure-Activity Relationship
Asteroidea
Fungi
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_01633864_v65_n2_p153_Chludil
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_01633864_v65_n2_p153_Chludil
record_format dspace
spelling todo:paper_01633864_v65_n2_p153_Chludil2023-10-03T15:02:13Z Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations Chludil, H.D. Seldes, A.M. Maier, M.S. anasteroside a anasteroside b antifungal agent glycoside thornasteroside unclassified drug versicoside a anasterias minuta antifungal activity article Asterias chemical modification Cladosporium cucumerinum correlation analysis drug isolation nonhuman nuclear magnetic resonance spectroscopy plant fungus interaction structure activity relation structure analysis sulfation and desulfurization Animals Antifungal Agents Argentina Cholestenones Chromatography, High Pressure Liquid Chromatography, Thin Layer Cladosporium Dose-Response Relationship, Drug Glycosides Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pregnenes Starfish Structure-Activity Relationship Asterias Asteroidea Cladosporium Cladosporium cucumerinum Fungi Two new sulfated steroidal hexaglycosides, anasterosides A (2) and B (3), along with the known versicoside A (1) have been isolated from the Patagonian starfish Anasterias minuta. Their structures have been elucidated by spectroscopic analysis (NMR and FABMS) and chemical transformations. Compounds 1 and 2 and the synthetic pentaglycoside 1b derived from versicoside A showed antifungal activity against the plant pathogenic fungus Cladosporium cucumerinum. Desulfation of hexaglycoside 1 rendered a totally inactive saponin. Fil:Seldes, A.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Maier, M.S. 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_01633864_v65_n2_p153_Chludil
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic anasteroside a
anasteroside b
antifungal agent
glycoside
thornasteroside
unclassified drug
versicoside a
anasterias minuta
antifungal activity
article
Asterias
chemical modification
Cladosporium cucumerinum
correlation analysis
drug isolation
nonhuman
nuclear magnetic resonance spectroscopy
plant fungus interaction
structure activity relation
structure analysis
sulfation and desulfurization
Animals
Antifungal Agents
Argentina
Cholestenones
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Cladosporium
Dose-Response Relationship, Drug
Glycosides
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pregnenes
Starfish
Structure-Activity Relationship
Asterias
Asteroidea
Cladosporium
Cladosporium cucumerinum
Fungi
spellingShingle anasteroside a
anasteroside b
antifungal agent
glycoside
thornasteroside
unclassified drug
versicoside a
anasterias minuta
antifungal activity
article
Asterias
chemical modification
Cladosporium cucumerinum
correlation analysis
drug isolation
nonhuman
nuclear magnetic resonance spectroscopy
plant fungus interaction
structure activity relation
structure analysis
sulfation and desulfurization
Animals
Antifungal Agents
Argentina
Cholestenones
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Cladosporium
Dose-Response Relationship, Drug
Glycosides
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pregnenes
Starfish
Structure-Activity Relationship
Asterias
Asteroidea
Cladosporium
Cladosporium cucumerinum
Fungi
Chludil, H.D.
Seldes, A.M.
Maier, M.S.
Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations
topic_facet anasteroside a
anasteroside b
antifungal agent
glycoside
thornasteroside
unclassified drug
versicoside a
anasterias minuta
antifungal activity
article
Asterias
chemical modification
Cladosporium cucumerinum
correlation analysis
drug isolation
nonhuman
nuclear magnetic resonance spectroscopy
plant fungus interaction
structure activity relation
structure analysis
sulfation and desulfurization
Animals
Antifungal Agents
Argentina
Cholestenones
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Cladosporium
Dose-Response Relationship, Drug
Glycosides
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pregnenes
Starfish
Structure-Activity Relationship
Asterias
Asteroidea
Cladosporium
Cladosporium cucumerinum
Fungi
description Two new sulfated steroidal hexaglycosides, anasterosides A (2) and B (3), along with the known versicoside A (1) have been isolated from the Patagonian starfish Anasterias minuta. Their structures have been elucidated by spectroscopic analysis (NMR and FABMS) and chemical transformations. Compounds 1 and 2 and the synthetic pentaglycoside 1b derived from versicoside A showed antifungal activity against the plant pathogenic fungus Cladosporium cucumerinum. Desulfation of hexaglycoside 1 rendered a totally inactive saponin.
format JOUR
author Chludil, H.D.
Seldes, A.M.
Maier, M.S.
author_facet Chludil, H.D.
Seldes, A.M.
Maier, M.S.
author_sort Chludil, H.D.
title Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations
title_short Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations
title_full Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations
title_fullStr Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations
title_full_unstemmed Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations
title_sort antifungal steroidal glycosides from the patagonian starfish anasterias minuta: structure - activity correlations
url http://hdl.handle.net/20.500.12110/paper_01633864_v65_n2_p153_Chludil
work_keys_str_mv AT chludilhd antifungalsteroidalglycosidesfromthepatagonianstarfishanasteriasminutastructureactivitycorrelations
AT seldesam antifungalsteroidalglycosidesfromthepatagonianstarfishanasteriasminutastructureactivitycorrelations
AT maierms antifungalsteroidalglycosidesfromthepatagonianstarfishanasteriasminutastructureactivitycorrelations
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