Isolation of (-)(2S)-5,6,7,3',5'-pentahydroxyflavanone-7-O-β-D Dglucopyranoside, new anti-inflammatory and cytotoxic flavanone

Abstract

A new flavanone glycoside, ( )(2S)-5,6,7,30,50-pentahydroxyflavanone- 7-O- -D-glucopyranoside (1), was isolated from the stems of Lippia graveolens H.B.K. (Verbenaceae). The structure of 1 was elucidated based on spectral analysis and chemical transformations. The treatment of 1 with acetic anhydride and pyridine afforded the corresponding peracetylated derivative 2, while an acid hydrolysis reaction of 1 afforded a 5,6,7,30,50-pentahydroxy flavanone (3). Additionally, the anti-inflammatory and cytotoxic activities of 1, 2 and 3 were determined.