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High-speed counter-current chromatography was used to separate and purify galloyl, caffeoyl, and hexahydroxydiphenoyl esters of glucoses from the aerial parts of the parasitic plant Balanophora simaoensis for the first time using n -hexane-ethyl acetate-methanol-water (1:2:1:2, v / v ) as the optimum solvent system. Accordingly, 1- O -( E )-caffeoyl-3- O -galloyl- β -d-glucopyranose ( I , 12.5 mg), 1- O -( E )-caffeoyl-3- O -galloyl-4,6-( S )-hexahydroxydiphenoyl- β -d-glucopyranose ( II , 27.2 mg), and 1- O -( E )-caffeoyl-4,6-( S )-hexahydroxydiphenoyl- β -d-glucopyranose ( III , 52.8 mg) with 98.0%, 98.5%, and 98.7% purities, respectively, were purified from 210 mg crude extract of B. simaoensis in a one-step separation. The structures of the glucose esters were identified by electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance spectra (NMR). Their antioxidant activities were evaluated by measuring their inhibition activity on liver microsomal lipid peroxidation induced by the Fe 2+ -Cys system in vitro. Compounds I ⁻ III showed significant antioxidant activities with IC 50 values ranging from 2.51 to 6.68 μm, respectively.

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Isolation and Purification of Galloyl, Caffeoyl, and Hexahydroxydiphenoyl Esters of Glucoses from Balanophora simaoensis by High-Speed Countercurrent Chromatography and Their Antioxidant Activities In Vitro