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.
Documento: | Artículo |
Título: | Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus |
Autor: | Careaga, V.P.; Muniain, C.; Maier, M.S. |
Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina Laboratorio de Ecología Química Y Biodiversidad Acuática, Instituto de Investigación e Ingeniería Ambiental, Universidad Nacional de San Martín, Peatonal Belgrano 3563 1, 1650 San Martín, Buenos Aires, Argentina |
Palabras clave: | (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 |
Año: | 2011 |
Volumen: | 8 |
Número: | 3 |
Página de inicio: | 467 |
Página de fin: | 475 |
DOI: | http://dx.doi.org/10.1002/cbdv.201000044 |
Título revista: | Chemistry and Biodiversity |
Título revista abreviado: | Chem. Biodiversity |
ISSN: | 16121872 |
CAS: | alcohol, 64-17-5; Antifungal Agents; Glycosides; Triterpenes; patagonicoside B; patagonicoside C |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16121872_v8_n3_p467_Careaga |