A series of C7-O-and C20-O-amidated 2, 3-dehydrosilybin (DHS) derivatives ((±)-1a− f and (±)-2), as well as a set of alkenylated DHS analogues ((±)-4a− f), were designed and de novo synthesized. A diesteric derivative of DHS ((±)-3) and two C23 esterified DHS analogues ((±)-5a and (±)-5b) were also prepared for comparison. The cell viability of PC12 cells, Fe2+ chelation, lipid peroxidation (LPO), free radical scavenging, and xanthine ...