Isoprenoid compounds from Euphorbia portlandica. X-ray structure of lupeportlandol, a new lupane triterpene

• Autor(a) principal: Madureira,Ana M.
• Data de Publicação: 2004
• Outros Autores: Duarte,Maria Teresa, Piedade,Maria Fátima M., Ascenso,José R., Ferreira,Maria-José U.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000500021
• topic: Euphorbia portlandica; triterpenes; steroids; lupane; X-ray diffraction

Phytochemical survey of the Me2CO extracts of the whole dried plant Euphorbia portlandica led to the isolation of a new pentacyclic triterpene alcohol, with the lupane skeleton, named lupeportlandol. Its structure was established as 3alpha-hydroxy-19alphaH-lup-20(29)-ene. The known pentacyclic triterpene glutinol and the steroid b-sitostenone were also isolated. The characterization of the new compound and its acetylated derivative was based on spectroscopic methods and an X-ray diffraction analysis. Lupeportlandol acetate was inactive in cytotoxicity assays in vitro against three human tumor cell lines: MCF-7 (breast cancer), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer).