Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus

Two new triterpene glycosides, patagonicosides B and C (2 and 3, resp.), together with the known patagonicoside A (1), have been isolated from the EtOH extract of the sea cucumber Psolus patagonicus. The structures of the new compounds were established on the basis of extensive NMR spectroscopic ana...

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Detalles Bibliográficos
Autores principales: Careaga, V.P., Muniain, C., Maier, M.S.
Formato: JOUR
Materias:
(3beta,12alpha,17alpha) 12,17 dihydroxy 18 ox -18,20 epoxylanosta 7,25 dien 3 yl 3 o methyl beta dextro glucopyranosyl(1-3) beta dextro xylopyranosyl(1-4) 6 deoxy beta dextro glucopyranosyl(1-2) beta dextro xylopyranoside
(3beta,12alpha,17alpha) 12,17 dihydroxy 18 oxo 18,20 epoxylanosta 7 en 3 yl 3 o methyl beta dextro glucopyranosyl(1-3) beta dextro glucopyranosyl(1-4) 6 deoxy beta dextro glucopyranosyl(1-2) beta dextro xylopyranoside
alcohol
antifungal agent
glycoside
patagonicoside a
patagonicoside b
patagonicoside c
triterpene derivative
unclassified drug
antifungal activity
article
carbon nuclear magnetic resonance
Cladosporium
Cladosporium cladosporoides
controlled study
drug isolation
drug structure
drug transformation
electrospray mass spectrometry
fractionation
heteronuclear multiple bond correlation
heteronuclear single quantum coherence
nonhuman
nuclear magnetic resonance spectroscopy
nuclear Overhauser effect
proton nuclear magnetic resonance
Psolus patagonicus
sea cucumber
solvolysis
sulfation
Animals
Antifungal Agents
Dose-Response Relationship, Drug
Glycosides
Microbial Sensitivity Tests
Molecular Conformation
Sea Cucumbers
Stereoisomerism
Structure-Activity Relationship
Triterpenes
Cladosporium cladosporioides
Fungi
Holothuroidea
Psolus
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_16121872_v8_n3_p467_Careaga
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:Two new triterpene glycosides, patagonicosides B and C (2 and 3, resp.), together with the known patagonicoside A (1), have been isolated from the EtOH extract of the sea cucumber Psolus patagonicus. The structures of the new compounds were established on the basis of extensive NMR spectroscopic analysis ( 1H- and 13C-NMR, 1H, 1H-COSY, HMBC, HSQC, TOCSY, and NOESY), HR-ESI-MS data, and chemical transformations. Compounds 1-3 and their desulfated analogs showed antifungal activities against the phytopathogenic fungus Cladosporium cladosporoides in a dose-dependent fashion. © 2011 Verlag Helvetica Chimica Acta AG.

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