Brasiliensic and isobrasiliensic acids: isolation from Calophyllum brasiliense Cambess. and anti-Helicobacter pylori activity

Abstract

The occurrence of chromanone derivatives has been noticed as a distinctive feature of the genus Calophyllum (Calophyllaceae). Previous studies have demonstrated that the extract of the stem bark of Calophyllum brasiliense and its chromanone-rich fractions show anti-ulcer activity in murine gastric ulcer models. In this work, brasiliensic and isobrasiliensic acids, the two main compounds of the n-hexane extract of the stem bark extract of C. brasiliense, were isolated by flash chromatography using silica gel impregnated with silver nitrate and their structures were elucidated by NMR techniques and mass spectrometry. ¹³C NMR data is available for the first time for both compounds. Brasiliensic and isobrasiliensic acids showed good in vitro bacteriostatic activity against Helicobacter pylori, and are responsible, at least in part, for the bacteriostatic anti-H. pylori activity of the n-hexane extract of the stem bark of C. brasiliense.

Keywords:

• Calophyllum brasiliense
• chromanone
• anti-Helicobacter pylori activity

Acknowledgements

The authors wish to acknowledge the technical assistance by Prof. Dr. Alberto José Cavalheiro, Araraquara Chemistry Institute, São Paulo State University (UNESP), Brazil, in the isolation of the compounds.

Disclosure statement

No potential conflict of interest was reported by the authors.

Funding

This work was supported by the Conselho Nacional de Desenvolvimento Científico e Tecnológico – CNPq [grant number 475445/2013-9], [grant number 306652/2010-2]; Fundação de Amparo a Pesquisa de Mato Grosso – FAPEMAT [grant number 015/2012]; FBC acknowledge funding by Fundação de Amparo à Pesquisa de São Paulo – FAPESP [grant number 2008/57149-8].