Bowdichine, a new diaza-adamantane alkaloid from Bowdichia virgilioides

Abstract

A novel alkaloid named bowdichine (1), only the third with a diaza-adamantane skeleton containing an unusual N-acetyl enamine moiety, and the known alkaloids acosmine (2), ormosanine (3) and podopetaline (4) have been isolated from the stem bark of Bowdichia virgilioides. The structures were elucidated on the basis of spectral data, mainly 1D and 2D NMR of the diaza-adamantane alkaloids 1 and 2.

Keywords:

• Bowdichia virgilioides
• Fabaceae
• Alkaloids
• Bowdichine
• Acosmine
• Ormosanine

Acknowledgements

The authors are grateful to CNPq, CAPES and FAPERJ (Brazil) for grants and fellowships (CNPq and CAPES), to Professor Maria de Fátima Agra (Universidade Federal da Paraíba) for botanical identification and to CENAUREMN/UFC for providing the NMR spectra.