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Journal of the Mexican Chemical Society
versão impressa ISSN 1870-249X
Resumo
JANKOWSKI, Christopher K. et al. Unusual Isomerisation of Cubebene. J. Mex. Chem. Soc [online]. 2006, vol.50, n.3, pp.90-95. ISSN 1870-249X.
Some sesquiterpenes extracted from Solidago canadensis L. in methanol underwent apparent isomerisation and the addition of water or methanol when the Soxhlet extraction was replaced by a microwave heating method in polar solvents. The quantity of α-cubebene, one of these sesquiterpenes, during microwave extraction, was dramatically increased. In this study, we present the detailed comparison of two cubebenes subjected to this isomerisation, 6-epi-α-cubebene and α-cubebene, as well as their solvent microwave induced addition products obtained under microwave irradiation in polar solvents. The analysis is supported by high resolution bidimensional NMR (1H, 13C), mass spectroscopy and selected isotopic labelling experiments.
Palavras-chave : Microwave; soxhlet extraction; isomerisation of sesquiter-pene; cubebenes; Solidago canadensis; NMR; tricyclic terpenes.