Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy 英文参考文献.docVIP

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Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy 英文参考文献.doc

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Molecules 2009, 14, 598-607; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Stereochemistry of 16α-Hydroxyfriedelin and 3-Oxo-16- methylfriedel-16-ene Established by 2D NMR Spectroscopy Lucienir Pains Duarte 1,*, Roqueline Rodrigues Silva de Miranda 2, Salom?o Bento Vasconcelos Rodrigues 1, Grácia Divina de Fátima Silva 1, Sidney Augusto Vieira Filho 3 and Vagner Fernandes Knupp 4 1 NEPLAM – Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Av. Ant?nio Carlos, 6627, Pampulha, CEP 31270-901, Belo Horizonte, Minas Gerais, Brazil 2 NEProNat - Departamento de Química – FACESA, Universidade Federal dos Vales do Jequitinhonha e Mucuri, Campus II - Rodovia MG 367 – Km 583, no 5000, CEP 39100-000, Diamantina, Minas Gerais, Brazil 3 DEFAR, Escola de Farmácia, Universidade Federal de Ouro Preto, Rua Costa Sena, 171, CEP 35400-000, Ouro Preto, Minas Gerais, Brazil 4 Centro Tecnológico de Minas Gerais, Av. José Candido da Silveira, 2000, CEP 31170-000, Belo Horizonte, Minas Gerais, Brazil * Author to whom correspondence should be addressed; E-mail: lupadu@netuno.lcc.ufmg.br; Fax: +55 31-3409-5700. Received: 20 November 2008; in revised form: 10 January 2009 / Accepted: 21 January 2009 / Published: 4 February 2009 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 an