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Molecules ; 14(2): 598-607, 2009 Feb 04.
Artículo en Inglés | MEDLINE | ID: mdl-19214150

RESUMEN

Friedelin (1), 3beta-friedelinol (2), 28-hydroxyfriedelin (3), 16alpha-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16alpha,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl(3) solution, 16alpha-hydroxyfriedelin (4) reacted turning into 3-oxo-16-methylfriedel-16-ene (7). This is the first report of a dehydration followed by a Nametkin rearrangement of a pentacyclic triterpene in CDCl(3) solution occurring in the NMR tube. These seven pentacyclic triterpenes was identified through NMR spectroscopy and the stereochemistry of compound 4 and 7 was established by 2D NMR (NOESY) spectroscopy and mass spectrometry (GC-MS). It is also the first time that all the (13)C-NMR and 2D NMR spectral data are reported for compounds 4 and 7.


Asunto(s)
Espectroscopía de Resonancia Magnética , Triterpenos/química , Medicamentos Herbarios Chinos/química , Espectroscopía de Resonancia Magnética/métodos , Conformación Molecular , Estructura Molecular , Salacia/química , Estereoisomerismo
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