Phenolic glycosides from <i>Sanguisorba officinalis</i> and their anti-inflammatory effects

Abstract

Two new phenolic glycosides 7<i>R</i>,8<i>R</i>-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-<i>O</i>-4'-neolignan-3'-<i>O</i>-(3''-α-L-arabinofuranosyl)-<i>β</i>-D-glucopyranoside. (<b>1</b>), 4-(4'-hydroxyphenyl)-2-butanone-4''-<i>O</i>-(6-<i>β</i>-D-xylosyl)-β-<i>D</i>-glucopyranoside (<b>2</b>), along with two known related analogues 7<i>R</i>,8<i>R</i>-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-<i>O</i>-4'-neolignan-3'-<i>O</i>-β-<i>D</i>-glucopyranoside (<b>3</b>), 4-(4'-hydroxyphenyl)-2-butanone-4'-<i>O</i>-β-<i>D</i>-glucopyranoside (<b>4</b>) were obtained from the roots of <i>Sanguisorba o</i>ffi<i>cinalis</i>. Combined with acid hydrolysis derivatization, the absolute configurations of these new compounds were elucidated by comprehensive analyses of spectroscopic data including nuclear magnetic resonance (NMR), electrospray ionization high resolution mass (HRESIMS) as well as circular dichroism (CD). Compounds <b>1</b>-<b>4</b> exhibited anti-inflammatory properties in vitro by attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6).