Guaianolide sesquiterpenes and benzoate esters from the aerial parts of Siegesbeckia orientalis L. and their xanthine oxidase inhibitory activity

Abstract

Five undescribed (four guaianolide sesquiterpenes and a benzoate ester derivative) and seven known compounds were isolated from the aerial parts of S. orientalis L. Their chemical structures were determined by extensive analysis of HR-ESI-MS and NMR spectroscopic methods. Absolute configurations were elucidated by experimental and TD-DFT calculated ECD spectra. Twelve isolated compounds exhibited potential xanthine oxidase inhibitory activity with IC₅₀ values ranging from 0.76 ± 0.17 μM to 31.80 ± 0.97 μM. Molecular docking studies predicted that the binding energies of all isolated compounds with xanthine oxidase were lower than that of the positive control allopurinol. Benzyl 2-hydroxy-6-O-β-D-glucopyranosylbenzoate and benzyl 2-methoxy-6-O-β-D-glucopyranosylbenzoate displayed not only the best docking score but also the highest in vitro xanthine oxidase inhibitory activity with IC₅₀ values of 0.76 ± 0.17 μM and 0.98 ± 0.26 μM, respectively.

Keywords: Benzoate ester derivative; Compositae; Guaianolide; Molecular docking; Siegesbeckia orientalis; Xanthine oxidase inhibitor.