Neolignans from Red Raspberry ( Rubus idaeus L.) Exhibit Enantioselective Neuroprotective Effects against H2O2-Induced Oxidative Injury in SH-SY5Y Cells.

Red raspberry has been well-known for its nutritional purpose. Although this fruit has been reported for its potent antioxidant activity and health-promoting properties, systematic studies responsible for the bioactive constituents were still insufficient. In the current study, three pairs of dihydrobenzofuran-type enantiomeric neolignans (1a/1b-3a/3b), including two new compounds (1b and 2a), were isolated from the fruit of Rubus idaeus. The structures of these enantiomers were determined through spectroscopic methods and quantum mechanical calculations. Biologically, enantiomers 2a and 2b exhibited significant enantioselective protective effects against H2O2-induced neurotoxicity at 50 μM (2a, 86.72 ± 1.17%; 2b, 69.70 ± 1.59%). The underlying mechanism study demonstrated that enantiomer 2a is able to attenuate H2O2-induced apoptosis, reactive oxygen species (ROS) generation, and mitochondrial dysfunction in SH-SY5Y cells. Overall, these findings provide a valuable foundation for the understanding of neuroprotective activities of red raspberry and further investigation on its potential application values.