3-Oxo-12alpha-hydroxyfriedelane from Maytenus gonoclada: structure elucidation by (1)H and (13)C chemical shift assignments and 2D-NMR spectroscopy

Mauro Lúcio G Oliveira; Lucienir Pains Duarte; Grácia Divina F Silva; Sidney Augusto Vieira Filho; Vagner Fernandes Knupp; Fernando Gomes P Alves

doi:10.1002/mrc.2062

3-Oxo-12alpha-hydroxyfriedelane from Maytenus gonoclada: structure elucidation by (1)H and (13)C chemical shift assignments and 2D-NMR spectroscopy

Magn Reson Chem. 2007 Oct;45(10):895-8. doi: 10.1002/mrc.2062.

Authors

Mauro Lúcio G Oliveira¹, Lucienir Pains Duarte, Grácia Divina F Silva, Sidney Augusto Vieira Filho, Vagner Fernandes Knupp, Fernando Gomes P Alves

Affiliation

¹ NEPLAM - Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Av. Antônio Carlos, 6627, Pampulha, CEP 31270-901, Belo Horizonte, Minas Gerais, Brazil.

PMID: 17729233
DOI: 10.1002/mrc.2062

Abstract

The compounds 3-oxofriedelane (1), 3beta-hydroxyfriedelane (2), 3,11-dioxofriedelane (3), 3,16-dioxofrie delane (4) and 3-oxo-12alpha-hydroxyfriedelane (5) were isolated from the hexane extract of Maytenus gonoclada Mart. (Celastraceae) leaves. Structural formula and the stereochemistry of the new pentacyclic triterpene 3-oxo-12alpha-hydroxyfriedelane (5) were established through (1)H and (13)C NMR and DEPT 135 spectral data including 2D experiments (HMBC, HMQC, COSY, and NOESY) and mass spectrometry (GC-MS).

MeSH terms

Carbohydrate Sequence
Carbon Isotopes
Magnetic Resonance Spectroscopy / methods*
Maytenus / chemistry*
Nitrogen Isotopes
Triterpenes / chemistry*

Substances

3-oxo-12alpha-hydroxyfriedelane
Carbon Isotopes
Nitrogen Isotopes
Triterpenes