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Title: Stereochemistry of 16α-hydroxyfriedelin and 3-oxo-16-methylfriedel-16-ene established by 2D NMR spectroscopy.
Authors: Duarte, Lucienir Pains
Miranda, Roqueline Rodrigues Silva de
Rodrigues, Salomão Bento Vasconcelos
Silva, Grácia Divina de Fátima
Vieira Filho, Sidney Augusto
Knupp, Vagner Fernandes
Keywords: Salacia elliptica
Issue Date: 2009
Citation: DUARTE, L. P. et al. Stereochemistry of 16α-hydroxyfriedelin and 3-oxo-16-methylfriedel-16-ene established by 2D NMR spectroscopy. Molecules, v. 14, p. 598-607, 2009. Disponível em: <>. Acesso em: 20 ago. 2014.
Abstract: Friedelin (1), 3β-friedelinol (2), 28-hydroxyfriedelin (3), 16α-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16α,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl3 solution, 16α-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 CDCl3 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 13C-NMR and 2D NMR spectral data are reported for compounds 4 and 7.
ISSN: 1420-3049
metadata.dc.rights.license: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Fonte: Molecules <>. Acesso em: 08 set. 2014.
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