A full set of 8,4'-oxy-8'-phenylneolignans with four chiral carbons, named (+)/(-)-leptolepisols D1-D2 and (+)/(-)-sophorols A-F, were isolated from the roots and rhizomes of Sophora tonkinensis Gagnep., including 14 previously undescribed stereoisomers, along with 2 known leptolepisol D diastereomers. Their planar structures and relative configurations were elucidated by detailed spectroscopic analysis (HRESIMS and NMR). Based on a highly accurate conformer filtering protocol at low computational cost, the absolute configurations of full set 8,4'-oxy-8'-phenylneolignans were completely assigned by TDDFT calculations of ECD spectra for the first time. Furthermore, (+)/(-)-sophorol A, (-)-sophorol B, and (-)-sophorol E could moderately suppress the lipopolysaccharide-induced nitric oxide production in murine macrophages at 10 mu m, with inhibitory ratios of 48.4-52.9%.
NSTL
Elsevier