Anti-inflammatory and Cytotoxic Lignans from Potentilla anserina

Abstract

Two undescribed lignans (7′R,8′R,8S)-4,4′,5,9,9′-pentahydroxy-3,3′,8-trimethoxy-2,7′-cyclolignan (1) and (8S,7′S,8′S)-4-[(4-hydroxy-3-methoxyphenyl)-methyl]-4-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyltetrahydrofuran (2) were isolated from Potentilla anserina L., Rosaceae, together with three known lignans, (+)-cycloolivil (3), (+)-lyoniresinol (4), and (+)-cycloolivil-6-O-β-D-glucopyranoside (5), which were reported for the first time from Potentilla spp. Their structures were determined on the basis of various spectroscopic methods (1D and 2D NMR, MS) and by comparison with the published NMR data. In addition, the absolute configurations of 1 and 2 were confirmed by comparison of the experimental and calculated electronic circular dichroism data. Furthermore, the anti-inflammatory activities of compounds 1–5 were assayed on lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells, and their cytotoxic activities to lung adenocarcinoma A549 tumor cell line were evaluated. It was found that compounds 2, 3, and 5 showed moderate anti-inflammatory and cytotoxic activities.