Isolation of enantiomeric furolactones and furofurans from Rubus idaeus L. with neuroprotective activities

Publication date: August 2019Source: Phytochemistry, Volume 164Author(s): Le Zhou, Feng-Ying Han, Li-Wei Lu, Guo-Dong Yao, Ying-Ying Zhang, Xiao-Bo Wang, Bin Lin, Xiao-Xiao Huang, Shao-Jiang SongAbstractA phytochemical study on the fruits of Rubus idaeus L. (Rosaceae) yielded eight pairs of enantiomeric lignans, including one undescribed furolactone named (−)-idaeusinol A and six undescribed furofuran derivatives named (+/−)-idaeusinol B–D. The structures of these isolated compounds were elucidated by spectroscopic analyses and a combination of computational techniques including gauge-independent atomic orbital (GIAO) calculation of 1D NMR data and TD-DFT calculation of electronic circular dichroism (ECD) spectra. Bioactivity screenings suggested that (+)-idaeusinol D exhibited the most significant protective effect against H2O2-induced neurotoxicity at the concentration of 25 μM. In contrast, (−)-idaeusinol D, as the enantiomer of (+)-idaeusinol D, showed no effect against H2O2-induced neurotoxicity at both 25 and 50 μM concentration.Graphical abstractEight pairs of enantiomeric lignans, including one undescribed furolactone and six undescribed furofuran derivatives were isolated from the fruit of Rubus idaeus. (+)-Idaeusinol D showed obvious neuroprotective activity at 25 μM concentration.

Source: Phytochemistry - May 22, 2019 Category: Chemistry Source Type: research