5-Hydroxymethylfurfural derivatives from wine-processed Corni fructus

Abstract

Four new 5-hydroxymethylfurfural derivatives, named cornusfurans A–D (1–4), together with three known ones (5–7) were isolated from wine-processed Corni fructus. They were a group of special components in Cornus officinalis processed with wine, in which compounds 1–4 were unusually constructed by a 5-hydroxymethylfurfural or 5-hydroxymethylfuroic acid and a small organic acid. Their structures were elucidated by comprehensive analyses of spectroscopic data and the absolute configurations of compounds 1–2 and 4 were solved by comparison of experimental and calculated electronic circular dichroism (ECD) curve. Bioassay results showed compounds 1–2 exhibited the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity, with IC50 values of 29.44 ± 3.79 and 42.30 ± 1.49 µM, respectively, and each isolated compounds had the protective effects against hydrogen peroxide (H2O2)-induced oxidative stress damage in normal rat kidney tubule epithelioid (NRK-52E) cells at 25–100 µM.