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

Jinfeng Chen, Lu Tan, Feng Ju, Qi-Xuan Kuang, Tian-Long Yang, Fang Deng, Yu‐Cheng Gu, Li-Shi Jiang, Yun Deng, Da‐Le Guo

2020Natural Product Research20 citationsDOI

Abstract

Two new phenolic glycosides 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-(3''-α-L-arabinofuranosyl)-β-D-glucopyranoside. (1), 4-(4'-hydroxyphenyl)-2-butanone-4''-O-(6-β-D-xylosyl)-β-D-glucopyranoside (2), along with two known related analogues 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-β-D-glucopyranoside (3), 4-(4'-hydroxyphenyl)-2-butanone-4'-O-β-D-glucopyranoside (4) were obtained from the roots of Sanguisorba officinalis. 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 1-4 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).

Topics & Concepts

ChemistryGlycosideDerivatizationStereochemistryCircular dichroismAnti-inflammatoryElectrospray ionizationMass spectrometryChromatographyPharmacologyMedicineNatural product bioactivities and synthesisPhytochemistry and Biological ActivitiesPhytochemistry and Bioactive Compounds