A full set of 8,4'-oxy-8'-phenylneolignan stereoisomers from Sophora tonkinensis and their absolute configurations by TDDFT.

Phytochemistry

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, China. Electronic address:

Published: May 2022

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 μM, with inhibitory ratios of 48.4-52.9%.

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Source
http://dx.doi.org/10.1016/j.phytochem.2022.113135DOI Listing

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