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

Author:
Zhou, Le, Han, Feng-Ying, Lu, Li-Wei, Yao, Guo-Dong, Zhang, Ying-Ying, Wang, Xiao-Bo, Lin, Bin, Huang, Xiao-Xiao, Song, Shao-Jiang
Source:
Phytochemistry 2019 v.164 pp. 122-129
ISSN:
0031-9422
Subject:
Rubus idaeus, chemical constituents of plants, circular dichroism spectroscopy, enantiomers, fruits, lignans, neuroprotective effect, neurotoxicity, nuclear magnetic resonance spectroscopy, spectral analysis
Abstract:
A 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.
Agid:
6441067