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Abstract:

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.

Registro:

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

Referencias:

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Citas:

---------- APA ----------
Careaga, V.P., Muniain, C. & Maier, M.S. (2011) . Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus. Chemistry and Biodiversity, 8(3), 467-475.
http://dx.doi.org/10.1002/cbdv.201000044
---------- CHICAGO ----------
Careaga, V.P., Muniain, C., Maier, M.S. "Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus" . Chemistry and Biodiversity 8, no. 3 (2011) : 467-475.
http://dx.doi.org/10.1002/cbdv.201000044
---------- MLA ----------
Careaga, V.P., Muniain, C., Maier, M.S. "Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus" . Chemistry and Biodiversity, vol. 8, no. 3, 2011, pp. 467-475.
http://dx.doi.org/10.1002/cbdv.201000044
---------- VANCOUVER ----------
Careaga, V.P., Muniain, C., Maier, M.S. Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus. Chem. Biodiversity. 2011;8(3):467-475.
http://dx.doi.org/10.1002/cbdv.201000044