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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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

id	todo:paper_16121872_v8_n3_p467_Careaga
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spelling	todo:paper_16121872_v8_n3_p467_Careaga2023-10-03T16:28:02Z Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus Careaga, V.P. Muniain, C. Maier, M.S. (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 Cladosporium Dose-Response Relationship, Drug Glycosides Microbial Sensitivity Tests Molecular Conformation Sea Cucumbers Stereoisomerism Structure-Activity Relationship Triterpenes Cladosporium cladosporioides Fungi Holothuroidea Psolus 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. Fil:Careaga, V.P. 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_16121872_v8_n3_p467_Careaga
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	(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 Cladosporium Dose-Response Relationship, Drug Glycosides Microbial Sensitivity Tests Molecular Conformation Sea Cucumbers Stereoisomerism Structure-Activity Relationship Triterpenes Cladosporium cladosporioides Fungi Holothuroidea Psolus
spellingShingle	(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 Cladosporium Dose-Response Relationship, Drug Glycosides Microbial Sensitivity Tests Molecular Conformation Sea Cucumbers Stereoisomerism Structure-Activity Relationship Triterpenes Cladosporium cladosporioides Fungi Holothuroidea Psolus Careaga, V.P. Muniain, C. Maier, M.S. Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus
topic_facet	(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 Cladosporium Dose-Response Relationship, Drug Glycosides Microbial Sensitivity Tests Molecular Conformation Sea Cucumbers Stereoisomerism Structure-Activity Relationship Triterpenes Cladosporium cladosporioides Fungi Holothuroidea Psolus
description	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.
format	JOUR
author	Careaga, V.P. Muniain, C. Maier, M.S.
author_facet	Careaga, V.P. Muniain, C. Maier, M.S.
author_sort	Careaga, V.P.
title	Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus
title_short	Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus
title_full	Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus
title_fullStr	Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus
title_full_unstemmed	Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus
title_sort	patagonicosides b and c, two antifungal sulfated triterpene glycosides from the sea cucumber psolus patagonicus
url	http://hdl.handle.net/20.500.12110/paper_16121872_v8_n3_p467_Careaga
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Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus

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