Davidones F and G, Two Novel Flavonoids from Sophora davidii (Franch.) Skeels.

Ping Song,Yu Peng,Xinzhou Yang,Ho-Young Choi,Yuanren Ma,Xuecui Li,Tongxi Zhou

doi:10.3390/molecules26144182

Abstract

An unprecedented novel flavanone davidone F (1) with a seven-membered ring side chain, and a novel flavanonol davidone G (2), along with 11 known flavonoids, were isolated from the ethyl acetate fraction of Sophora davidii (Franch.) Skeels. Their planar structures were established by UV, IR, HRESIMS, 1D and 2D NMR data. The relative configurations of 1 and 2 were determined by calculation of NMR chemical shift values, the absolute configuration of 1 and 2 were assigned by comparing their experimental and calculated electronic circular dichroism (ECD) spectra. Moreover, compounds 1–13 were screened for the translocation activity of glucose transporter 4 (GLUT-4), and the fluorescence intensity was increased to the range of 1.56 and 2.79 folds. Compounds 1 and 2 showed moderate GLUT-4 translocation activity with 1.64 and 1.79 folds enhancement, respectively, at a concentration of 20 μg/mL.

Highlights

Sophora davidii (Franch.) Skeels are shrubs or dungarungas, which belong to the familyFabaceae, mainly distributed in Guizhou, Ningxia, Yunnan and Sichuan provinces of China [1]
To enhance our understanding of the chemical and biological diversity of the Sophora species, the chemical investigation of S. davidii led to the isolation of one new prenylated flavanone, davidone F (1), with a novel seven-membered oxygen ring, and one new prenylated flavanonol, davidone G (2), together with one known flavanonol (3), two known chalcones (5–6), four known isoflavones (7–12) and one known flavonol (13) (Figure 1)
The molecular formula was established as C26H30O7 by HRESIMS data (m/z 455.2061 [M + H]+, calculated for 455.2064), indicating 12 indices of hydrogen deficiency

Summary

Introduction

Sophora davidii (Franch.) Skeels are shrubs or dungarungas, which belong to the familyFabaceae, mainly distributed in Guizhou, Ningxia, Yunnan and Sichuan provinces of China [1]. Sophora davidii (Franch.) Skeels are shrubs or dungarungas, which belong to the family. The plant has proven to be a rich source of flavonoids, alkaloids, steroids, lignans and phenolic acids [3,4,5]. Flavonoids, as the main compounds of S. davidii, have a broad spectrum of biological activities. To enhance our understanding of the chemical and biological diversity of the Sophora species, the chemical investigation of S. davidii led to the isolation of one new prenylated flavanone, davidone F (1), with a novel seven-membered oxygen ring, and one new prenylated flavanonol, davidone G (2), together with one known flavanonol (3), two known chalcones (5–6), four known isoflavones (7–12) and one known flavonol (13) (Figure 1). We describe the isolation, structure elucidation and GLUT-4 translocation activities of these isolated compounds

Methods

Results

Conclusion