Isolation of (−)(2S)-5,6,7,3′,5′-pentahydroxyflavanone-7-O-β-D-glucopyranoside, from Lippia graveolens H.B.K. var. berlandieri Schauer, a new anti-inflammatory and cytotoxic flavanone

Abstract

A new flavanone glycoside, (−)(2S)-5,6,7,3′,5′-pentahydroxyflavanone-7-O-β-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 per-acetylated derivative 2, while an acid hydrolysis reaction of 1 afforded a 5,6,7,3′,5′-pentahydroxy flavanone (3). Additionally, the anti-inflammatory and cytotoxic activities of 1, 2 and 3 were determined.

Keywords:

• Lippia graveolens
• flavanone
• anti-inflammatory
• cytotoxic

Acknowledgements

We are grateful to Teresa Ramírez-Apam, Antonio Nieto, Javier Pérez, Luis Velasco, Nieves Zavala, Hector Rios, Isabel Chávez, Rocio Patiño and Beatriz Quiroz for providing technical assistance.